Phytochemicals
These are a few of the pharmacologically significant phytochemical and mycochemical compounds which may be present in our local species. The aim of these chemical profiles is to quickly identify substances and look for ways to utilize or denature these chemical compounds. Saponins are a great example of a culturally adapted biochemical, useful as a soap or a fish poison. Some compounds are ubiquitous, such as tannins, compounds that have been used to tan animal hides and which can be anti-nutritional in excess. Some compounds, such as veratridine, are incredibly poisonous and may be useful as a hunting poison or as an insecticide.
"While many of the thousands of chemicals in plants can be poisonous, their concentrations are for the most part too low to be of concern. Generally one would have to consume prodigious amounts of a given plant species to suffer ill effects. A famous example was provided by Basil Brown, an English health food enthusiast who in 10 days in 1974 drank about 45 L (10 imperial gallons) of carrot juice, thereby consuming about 10 000 times the recommended requirement of vitamin A. At the end of the 10 days his skin was bright yellow, and he was dead of severe liver damage (McGee 1984)." [Small CH] It should be noted that a Feb 17, 1974 article in the New York Times states that Brown also consumed 70 million units of vitamin A during the 10 days in which he consumed the carrot juice. [Personal observation]
This page is a work in-progress and far from comprehensive. I hope to organize and provide a summary of the most recognized biochemicals found in all biota, with a majority of the focus placed on plant and fungi derived metabolites. Those with potential for dietary and therapeutic influence will be rigorously explored. [Personal Note]
Contents (Sorted Alphabetically) |
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Plant/Fungi Primary Metabolities |
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Carbohydrates cholesterol Enzymes Lipids |
Neurotransmitters Proteins triglycerides Vitamins |
Plant/Fungi Secondary Metabolities |
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Alkaloids Alkamides Amines Fatty acids Glycosides Glucosinolates Hormones Lectins lignins NPAAs (Non-proteinogenic Amino Acids) Other Compounds |
Peptides Phenols/Phenylpropanoids/coumarins/lignans Polyacetylenes Polyketids Polyphenols Steroids Saponins Terpenes Tetraterpenoids waxes Essential oils Pigments (chlorophyll, astaxanthin, zeaxanthin, indigoidine, rhodopsin) Antibiotics Flavonoids (Apigenin, Luteolin, Hesperetin, Genistein) |
Index |
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Alkaloids |
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"Their definition is problematic, as they do not represent a homogeneous group of compounds from any standpoint, whether chemical, biological, or physiological. Except for the fact that they are all nitrogen-containing compounds, no general definition fits all alkaloids." [MHC Hoffman] "Despite the difficulty in defining them, most alkaloid share physical and chemical properties. They are usually insoluble or sparingly soluble in water, most are alkaline, and many possess physiological activity. "Alkaloids are nitrogen heterocyclic substances, found in over 13 000 species. Most plant alkaloids come from amines or amino acids and only some come from isoprenoid precursors in which nitrogen is incorporated into a late stage of the biosynthetic cycle. This is the case with solanine (glycoalkaloid) from Solanum tuberosum and tomatine and its aglycone, tomatidine from Lycopersicon esculentum. Alkaloids have been identified in vacuoles, chloroplasts, and extraplasmatic space. Enzymes involved in the synthesis of these substances have been identified in endoplasmic reticulum membranes, plasmalemma, and tonoplast." [Singh APB] |
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Alkamides |
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"In alkamides, amines are combined with unsaturated fatty acids by amide linkages, forming unbranched chains with one or more double and/or triple bonds." [Pengelly TCMP] "The alkamides, also known as alkylamides, are fatty acid amides which vary in structure and function. Alkamides are found in nature in over 100 plant species, where they are thought to act as a defense against herbivory [1]. Alkamides contain a fatty acid tail, which can vary in the number of carbons and unsaturations, an amide group, and a variable headgroup." [Johnstone&Laster,2021] "Alkamides are responsible for the sharp, burning or tingling taste associated with herbs and spices such as prickly ash bark (Zanthoxylum spp.), black pepper (Piper nigrum), Echinacea angustifolia, E. purpurea and cayenne (Capsicum spp.). Capsicum oleoresin contains several phenolic amides including capsaicin." [Pengelly TCMP] "Alkamides are a large group of natural products occurring in at least 33 plant families. They possess a broad range of biological activities including analgesic, cannabimimetic, and immunomodulatory properties. Interestingly, two recent extensive reviews on alkamides did not list Ranunculaceae as an alkamide-producing family [108,109]." [Jetter FSAP] As of this 2010 publication, it's reported that approximately 150 nitrogen-containing alkamides have been identified in higher plants. [Wink BBPSM] |
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Compound |
Sources |
| Pellitorine | Piper longum [Johnstone&Laster,2021] |
| pipercyclobutanamide A | Piper nigrum - long pepper [Root] [Huu, Duc Minh Nguyen, et al., 2021] |
| Piperlongumine | Piper longum - long pepper [Root] [Tripathi&Biswal,2020] |
| Sanshool | Zanthoxylum clava-herculis (α-sanshool) [Johnstone&Laster,2021] |
| Spilanthol | Spilanthes sp., Spilanthes acmella [Johnstone&Laster,2021] |
| undeca-2Z,4E-diene-8,10-diynic acid isobutylamide | Echinacea [Johnstone&Laster,2021] |
| dodeca-2E,4E,8Z,10E/Z-tetraenoic acid isobutylamide | Echinacea [Johnstone&Laster,2021][Tracy HPTCP] |
| dodeca-2E,4E-dienoic acid isobutylamide | Echinacea [Johnstone&Laster,2021][Tracy HPTCP] |
| undeca-2E-ene-8,10-diynoic acid isobutylamide | Echinacea [Johnstone&Laster,2021] |
| Undeca-2D/Z-ene-8,10-diynoic acid isobutylamides | Echinacea [Tracy HPTCP] |
| Dodeca-2D,4Z-diene-8,10-diynoic acid isobutylamide | Echinacea [Tracy HPTCP] |
| Dodeca-2E-ene-8,10-diynoic acid isobutylamide | Echinacea [Tracy HPTCP] |
| Dodeca-2E,4E,8Z-trienoic acid isobutylamide | Echinacea [Tracy HPTCP] |
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Pellitorine: "pellitorine has also been shown to be an effective insecticidal agent against the housefly and Aedes aegypti mosquito [20, 21]." [Johnstone&Laster,2021] pipercyclobutanamide A: "From the EtOH-soluble extract of the roots of Piper nigrum, one new dimeric alkamide, pipercyclobutanamide D (1) was isolated.... Compound 1 showed α-glucosidase inhibitory activity with an IC50 value of 158.5 µM. In addition, compound 1 exhibited cytotoxicity against the MCF-7 and HepG2 cell lines with the IC50 values of 45.6 and 63.9 µM, respectively. [Huu, Duc Minh Nguyen, et al., 2021] Piperlongumine: "Piperlongumine (piplartine) is a well-known biologically
active alkaloid/amide found in the roots of the plant Piper longum (long pepper) [7]." [Tripathi&Biswal,2020] Spilanthol: "Spilanthol is the predominant alkamide found in Spilanthes sp. with several other alkamides reported in lesser quantities [29]. Commercial preparations of spilanthol are as available for use as oral analgesics and to provide a long-lasting mint flavor in toothpastes [2].... Spilanthol displays structural similarities to capsaicin, the ligand for the nociceptor channel TRPV1, which may account for its analgesic properties [23]. Isolated spilanthol also displays immunomodulatory properties in vitro causing dose dependent reduction in macrophage activation and nitric oxide (NO) production, as well as inhibition of cytokine production and NF-κB activation [31]." [Johnstone&Laster,2021] Cinnamides"Cinnamides can be considered a subclass of alkamides in which the acid portion is derived from hydroxycinnamic acids such as caffeic, ferulic, or isoferulic acid, and the amine part is derived from amino acids or biogenic amines. The iden- tification of black cohosh cinnamides, many of which are new natural products, was accomplished by a simple strategy that will be described here using the unique black cohosh cinnamides caffeoyl (46) and feruloyl/isoferuloyl arginine (47,48) as exemplary compounds." [Jetter FSAP] Isobutylamides"Isobutylamides are a subclass of alkamides based on the amine group 2-methylpropyl. They first aroused the interest of researchers for their insecticidal activities, being toxic to numerous classes of insects including the ubiquitous housefly and mosquito. Upon further investigation, it was obvious the most active insecticidal compounds were the ones that produced the most potent sialagogue (stimulating saliva flow) effects in humans (Brinker 1991/92). Isobutylamides so far investigated are derived from four plant families—Asteracea, Rutaceae, Piperaceae and Aristolochiaceae...." [Pengelly TCMP] Capsaicinoids"These compounds are responsible for the hotness in chillis (hot
peppers), the degree of pungency being related to the length of the
acid side chain. Total capsaicinoid content is around 1% of the dried
fruit, the majority of which is usually capsaicin. Structurally, capsaicinoids are vanillyl-acyl amide analogues (Tucker and Debaggio
2000). Pharmacology"Alkamides can be readily detected by organoleptic means, by placing a very small quantity on the tongue. The initial sharp sensation and saliva production is followed by a local anaesthetic or numbing effect. Not surprisingly many are associated with management of toothache—Spilanthes and Zanthoxylum spp. are both known in their respective regions as ‘toothache plant’. The most significant actions of alkamides are analgesic, antiinflammatory, counter-irritant, sialagogue, vermifuge, digestive and circulatory stimulation. Other likely effects are spasmolytic, carminative and immune stimulation." [Pengelly TCMP] "Similar to alkaloids, some alkamides from Piper spp. are reported to exert in vitro schistosomicidal activity. Piplartine (compound 12, Fig. 8-4), an amide found in several Piper spp., such as Piper tuberculatum, showed in vitro activity against adult S. mansoni worms. It was reported that treatment with 15.8 mM piplartine reduced motor activity and egg production, as well as killing all adult worms. Piplartine also induced morphologic changes in the tegument, causing extensive tegumental destruction and damage to the parasite tubercles. This damage was dose dependent in the range of 15.8-630.2 uM. More schistosomicidal and phytochemical studies should be conducted with Piper spp. since most have shown to be active against schistosomes [91]." [Rai FMDR] Stability"Alkamides are known to be subject to degradation over time. Studies on Echinacea purpurea alkamides showed that, while drying had no effect, most of the compounds were lost after the dried roots had been stored for a little over a year (Perry and van Klink 2000). Loss of alkamides was rather less when the roots were stored at subzero temperatures. Preservation in ethanolic tincture form is an effective method of retaining these compounds. Chopping the root produces only minimal losses." [Pengelly TCMP] "A recent study has analyzed the effect of some processing variables on the content of solvent-soluble constituents. Chopping altered the level of some alkamides slightly in E. purpurea roots but drying had no significant effect on the amounts detected. Levels of all alkamides fell by over 80% on storage at room temperature for 16 months and also fell significantly even when the plant material was stored at 18oC (82)." [Packer HTM] Echinacea"Other constituents found in Echinacea include 15 lypophilic alkamides, most of which contain one or two acetylenic bonds." [Shahidi PIF] Echinacea (Echinacea purpurea, Echinacea angustifolia, or Echinacea pallida) "The alkamides comprise a complex mixture of unsaturated fatty acids as amides with 2-methylpropanamine (isobutylamine) or 2-methylbutanamine, amines which are probably decarboxylation products from valine and isoleucine respectively. The acid portions are predominantly C11 and C12 diene-diynes or tetraenes (Figure 3.13). These compounds are found throughout the plant, though relative proportions of individual components vary considerably. The root of Echinacea purpurea contains at least 12 alkamides (about 0.6%), of which C12 diene-diynes predominate; levels of these compounds fall significantly during drying and storage." [MNP Dewick] "More than 20 alkamides, mostly isobutylamides of C11–C16 straight-chain fatty acids with olefinic or acetylenic bonds, or both, are found in the roots; the highest concentration is in E. angustifolia, followed by E. purpurea, and the lowest is in E. pallida. The main alkamide is a mixture of isomeric dodeca-2,4,8,10-tetraenoic acid isobutylamides." [WHO SMPV.1] "Hinz et al. (2007) showed that alkamides derived from E. angustifolia roots may contribute to the pharmacological action by inhibiting COX-2-dependent PGE2 formation at sites of inflammation (Hinz et al., 2007)." [Seeram HM] "Several alkamides from E. purpurea showed ca. 48% and 30% inhibition of COX-1 and -2, respectively, at 100 mg/mL.20" [Leung ECNI] "Polyunsaturated alkamides isolated from Echinacea angustifolia inhibit cyclooxygenase and 5-lipoxygenase in vitro (Mullr-Jakic et al., 1994)." [TCPH] "Preclinical studies indicate that Echinacea constituents modulate immune mechanisms and there is an increasing evidence that lipophilic Echinacea preparations containing alkamides can suppress stress-related cellular immune responses.... Chicca et al. reported that a synergism between Echinacea lipids (mixtures of alkamides) from radix and herba tinctures are likely to mediate superior anti-inflammatory and immuno-pharmacological effects over single compounds." [Seeram HM] Antiviral: "Recently, as an alternative approach to the common anti-viral therapy (vaccines and a few anti-viral drugs), a commercial standardized extract of Echinacea (Echinaforce®, an ethanolic extract of herb and roots of E. purpurea) has been studied in order to elucidate the nature of its anti-influenza virus activity. Human H1N1-type IV, highly pathogenic avian IV (HPAIV) of the H5- and H7-types, as well as swine origin IV (S-OIV, H1N1), were all inactivated in cell culture assays by the E. purpurea preparation at concentrations ranging from the recommended dose for oral consumption to several orders of magnitude lower (MIC100 values increased from 0.32 µg/mL Echinaforce® for 102 PFU/mL virus, up to 7.5 µg/mL Echinaforce® for 105 PFU/mL). Hemagglutination assays showed that the extract inhibited the receptor binding activity of the virus, suggesting that the Echinacea extract interferes with the viral entry into cells. Furthermore, a Tamiflu®-resistant virus was just as susceptible to E. purpurea preparation as the wild-type virus (Pleschka et al., 2009). Another approach for an anti-viral action has been investigated with herpes simplex virus type-1 (HSV-1), which often causes recurrent ocular disease during the latency period. An Echinacea polysaccharide fraction (isolated from E. purpurea aerial parts at a concentration of 20 mg/mL; Zardband Pharmaceutical Company) led to a reduced latency rate and exerted an anti-viral action on the development of recurrent HSV-1 disease when supplied prior to infection (Ghaemi et al., 2009)." [Seeram HM] "Recently, Echinacea alkamides have been reported to be a new class of cannabinomimetics modulating tumor necrosis factor α gene expression via the cannabinoid type 2 receptor" [Seeram HM] "Overall, the studies have shown that most of the alkamides present in Echinacea preparations are bioavailable from an oral dose of different Echinacea formulations...." [Seeram HM] "So far, the therapeutic activity of Echinacea cannot be unambiguously attributed to any particular constituent. However, recent pharmacological data suggest that within the active principle of Echinacea, the alkamides showed the most abundant proper- ties with marked immunomodulatory, anti-inflammatory, anti-viral, and bactericidal effects.... According to these results and the CB receptor binding activities, and since bioavailability has been demonstrated, alkamides seem to be clinically highly relevant constituents of Echinacea (Woelkart and Bauer, 2007)." [Seeram HM] Insecticide: "Different alkamides of E. purpurea produced 100% mortality in Aedes aegyptii mosquito larvae when tested in vitro at 100 mg/mL.20" [Leung ECNI] Misc AlkamidesArtemisia dracunculus; "The aerial parts contain the alkamides, pellitorine, and neopellitorine A and B. The latter two were isolated as new compounds from A. dracunculus.3" [Leung ECNI] Piper nigrum; "Aqueous and organic extracts and many alkamides of black pepper exhibited antibacterial activity against both Gram-positive and Gram-negative bacteria.14,30 Larvicidal and insecticidal activities have also been reported.7,9,10,13,31,32" [Leung ECNI] "As detailed above, many alkamides are present in E. angustifolia roots where they are particularly abundant in quantity. Their structures are derived from undeca- and dodecanoic acid and differ from one another in the degree of unsaturation and the configuration of the double bonds (66). In E. purpurea roots there are characteristic differences in that most of the 11 alkamides possess a 2,4-diene moiety. This makes a convenient marker for distinguishing the source of the material (4,75). The aerial parts contain similar constituents (67,68). The concentration of most of these compounds is significantly less than 1% (0.001–0.151%). Alkamide levels in various parts of E. purpurea differ sufficiently to suggest that measurements of their distribution could be used to determine the origin of extracts (79). The photochemical instability of such compounds would require considerable caution in sample preparation and handling (80)." [Packer HTM] Phyllanthus niruri; "Two alkamides, E,E-2,4-octadienamide and E,Z-2,4-decadienamide have also been isolated from the plant with anti- plasmodial activities. The anti-plasmodial activity has been attributed to the presence of α, β, γ, δ-unsaturated conjugated amide (Sittie et al. 1998)." [Rai FMDR] |
References
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Amines |
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"Amines are derivatives of ammonia in which one or more of the hydrogen atoms have been replaced by an alkyl or aryl group, so like ammonia they are basic compounds." [X Ge et al.,2011] "Amines are emitted by a wide range of sources and are ubiquitous atmospheric organic bases. Approximately 150 amines and about 30 amino acids have been identified in the atmosphere." [X Ge et al.,2011] "Biologically active amines are normal constituents of many foods and have been found in cheese; sauerkraut; wine; and putrid, aged, or fermented meats. These low molecular weight organic bases do not represent any hazard to individuals unless large quantities are ingested or natural mechanisms for their catabolism are inhibited or genetically deficient." [Rice et al., 1976] "Biogenic amines are conveniently divided into aliphatic monoamines, aliphatic di- and polyamines and aromatic amines. These compounds are shown to fulfill an array of roles in cellular metabolism. Thus, amines are needed for growth and development and their metabolism appears to be coordinated with the cell cycle." [Bouchereau et al., 2000] "Biogenic amines (BA) are organic compounds commonly found in food, plants and animals, as well as microorganisms that are attributed with the production of BAs. They are formed as an effect of a chemical process: the decarboxylation of amino acids. Factors determining the formation of BAs include the availability of free amino acids and the presence of microorganisms that show activity with respect to carrying out the decarboxylation process. On the one hand, BAs are compounds that are crucial for maintaining cell viability, as well as the proper course of the organism's metabolic processes, such as protein synthesis, hormone synthesis and DNA replication. On the other hand, despite their positive effects on the functioning of the organism, an excessive content of BAs proves to be toxic (diarrhea, food poisoning, vomiting, sweating or tachycardia). Moreover, they can accelerate carcinogenesis. " [Wójcik et al., 2020] "Polyamines are found in foods of both animal and plant origin, either in a free or conjugated form. Conjugated polyamines are found in plant-derived foods mainly linked to phenolic compounds (4, 24). In foods, spermidine and spermine are primarily naturally present, coming from raw plant and animal tissues, whereas putrescine may also be formed by the activity of fermentative or contaminating microorganisms (12, 53). It has also been described that spermidine and spermine may partly have a bacterial origin, especially in fermented products (12, 54, 55). Therefore, processing and storage conditions can influence the total content of polyamines." [Muñoz-Esparza, Nelly C., et al.,2019] "The polyamines spermine, spermidine, and putrescine are involved in various biological processes, notably in cell proliferation and differentiation, and also have antioxidant properties. Dietary polyamines have important implications in human health, mainly in the intestinal maturation and in the differentiation and development of immune system. The antioxidant and anti-inflammatory effect of polyamine can also play an important role in the prevention of chronic diseases such as cardiovascular diseases. In addition to endogenous synthesis, food is an important source of polyamines. Although there are no recommendations for polyamine daily intake, it is known that in stages of rapid cell growth (i.e., in the neonatal period), polyamine requirements are high. Additionally, de novo synthesis of polyamines tends to decrease with age, which is why their dietary sources acquire a greater importance in an aging population." [Muñoz-Esparza, Nelly C., et al.,2019] "Effects of Culinary Treatment
tyramine IndolaminesMelatonin: "Melatonin is an amphipathic indolamine molecule ubiquitously present in all organisms ranging from cyanobacteria to humans. The pineal gland is the site of melatonin synthesis and secretion under the influence of the retinohypothalamic tract. Some extrapineal tissues (skin, lens, gastrointestinal tract, testis, ovary, lymphocytes, and astrocytes) also enable to produce melatonin. Physiologically, melatonin regulates various functions like circadian rhythm, sleep–wake cycle, gonadal activity, redox homeostasis, neuroprotection, immune-modulation, and anticancer effects in the body. Inappropriate melatonin secretion advances the aging process, tumorigenesis, visceral adiposity, etc." [Samanta, Saptadip.,2020] "Using the described method of extraction and after correction of the values for the recovery rate (about 40%), the calculated concentrations of melatonin in walnuts was 3.5 +- 1.0 ng/g." [Reiter et al.,2005] Serotonin: methylamines |
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Compound |
Sources |
| Melatonin (Indolamine) | "Melatonin has been reported in edible fruits (grape, banana, strawberries, apple, pineapple, Kiwi fruit, tart cherries, etc.), vegetables (tomato, pepper, mushroom, cabbage, cauliflower, cucumber, carrot, beetroot, etc.), nuts and raw seeds (walnuts, sunflower, green cardamom, fenugreek, white and black mustard, etc.), juices and beverages (wines, green and roasted coffee beans, decoction brew)." [Ramakrishna et al.,2021] |
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References
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[Muñoz-Esparza, Nelly C., et al.,2019]
[Muñoz-Esparza, Nelly C., et al.,2019]Carbohydrates <-Separate profiles page |
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Sucrose, maltose, fructose, glucose, maltodextrin, dextrose, sugar alcohols = maltitol, erythritol, and hydrogenated starch hydrolysate |
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Compound |
Sources |
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Seaweed Sourced Plant Sourced |
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Alginate |
Ascophyllum nodosum [McHugh, Dennis J.,1987] Durvillaea antarctica, D. lessonia, D. potatorum [McHugh, Dennis J.,1987] Ecklonia cava [McHugh, Dennis J.,1987] Laminaria digitata, L. hyperborea [McHugh, Dennis J.,1987] Lessonia [McHugh, Dennis J.,1987] Macrocystis [McHugh, Dennis J.,1987] Padina tetrastromatica - Brown algae [Sharma&Baskaran.,2021] Sargassum [McHugh, Dennis J.,1987] Turbinaria [McHugh, Dennis J.,1987] |
Agar |
family Gracilariaceae, Gelidiaceae, Pterocladiaceae and Gelidiellaceae [Lee, Wei-Kang, et al.,2017] |
Carrageenans |
Numerous species of red seaweeds (Rhodophyta) [Stanley,Norman.,1987] Chondrus crispus, C. ocellatus [Stanley,Norman.,1987] Eucheuma Sp. (Eucheuma cottonii, E. spinosum, E. gelatinae) [Stanley,Norman.,1987] Furcellaria fastigiata [Stanley,Norman.,1987] Gigartina stellata, G. acicularis, G. pistillata, G. canaliculata, G. chamissoi, G. skottsbergii [Stanley,Norman.,1987] Gigartina radula (also identified in the literature as Iridea species) [Stanley,Norman.,1987] Gymnogongrus furcellatus [Stanley,Norman.,1987] Hypnea musciformis and H. spicifera [Stanley,Norman.,1987] |
Floridean starch |
Rhodophyta [Dominguez FIAFN] |
Fucoidans |
Ascophyllum nodosum [Rioux et al.,2010] Laminaria brasiliensis [Rioux et al.,2010] Laminaria religiosa [Koo et al.,1995] Padina tetrastromatica - Brown algae[Sharma&Baskaran.,2021] Saccharina longicruris [Rioux et al.,2010] Undaria pinnatifida [Koo et al.,1995] |
| galactofucan | Laminaria brasiliensis [Rioux et al.,2010] |
Laminaran |
Cystoseira barbata [Sellimi, Sabrine, et al.,2018] Dictyota dichotoma [Malyarenkob et al.,2019] Ecklonia maxima [laminarin = 9.57% dry matter (dm)] [Rocher et al.,2021] Laminaria Sp. [Sanjeewa et al.,2017][Zargarzadeh et al.,2020] Saccharina Sp. [Sanjeewa et al.,2017][Zargarzadeh et al.,2020] Saccharina longicruris, formerly named Laminaria longicruris [Rioux et al.,2010] Sargassum crassifolium [Chamidah et al.,2017] |
| Mannitol | [] |
| Porphyran | [] |
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Pyrus aucuparia (Berries)[Merck] Sorbus aucuparia (Berries)[Merck] |
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Ulvans |
Ulva pertusa [Kim, Ji Hye, et al.,2018] |
References
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EnzymesFour plant enzyme groups exist: [FEMI]
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"Few bacteria are able to use complex carbohydrates such as disaccharides (sucrose) or polysaccharides (starch). Disaccharides and polysaccharides are simple sugars that are linked by glycosidic bonds; bacteria must produce enzymes to cleave these bonds and produce simple sugars that can be transported into the cell. If bacteria are not able to produce these enzymes, then the complex carbohydrates are not used. For example, starch is a large polysaccharide consisting of long chains of monomeric glucose (α-amylose and amylopectin) linked by glycosidic bonds. Bacteria that use starch must first produce several types of enzymes called amylases (α-amylases, glucoamylases, β-amylases, and others such as exo-α1,4-gluconases) that break glycosidic bonds and thus free monomeric glucose is produced and used directly by the microorganisms (Nigan and Singh 1995; Chen 2002). [????] "Starch-degrading enzymes include: a-amylases, which are endoamylases acting on 1,4 bonds and bypassing the 1,6 bonds; b-amylases, which are exoamylases producing the disaccharide maltose by splitting alternate 1,4 bonds until they reach a 1,6 branch point (which they cannot bypass); amyloglucosidases (or glucoamylases), which can act on both 1,4 and 1,6 bonds, seem to occur almost exclusively in fungi; debranching enzymes (e.g. pullulanase) which sever 1,6 bonds; a-glucosidases which hydrolyse 1,4 glycosidic linkages in disaccharides and oligosaccharides, producing glucose as the end-product of starch breakdown." [Moore 21stFungi] Digestive Enzymes"Sucrase, a membrane-bound enzyme of the small intestine, catalyzes the hydrolysis of sucrose, yielding one molecule each of glucose and fructose." [NB Brody] "Lactase, a membrane-bound enzyme of the small intestine, catalyzes the hydrolysis of lactose to glucose and galactose. (Lactose should not be confused with the 3-carbon carbohydrate lactic acid.) The monosaccharide galactose generally is not found in the diet. However, this sugar may be liberated from lactose by the bacterial enzyme [β-galactosidase, present in yogurt because it is produced during culturing of the product. Hydrolysis of lactose to glucose and galactose probably occurs not in the yogurt itself, but in the human gut after yogurt consumption. This hydrolysis may account for the lower incidence of lactose intolerance with the consumption of yogurt (derived from milk) than with milk itself. Lactose is not present in significant amounts in plants." [NB Brody] "Some beans contain significant quantities of the sugars raffinose and stachyose .... These sugars are not digestible by enzymes produced by humans, although they can be used by the gut microflora, producing gaseous waste products. The increase in microbial metabolism provoked when undigested sugars reach the large intestine results in an increase in the rate of production of various gases in the gut lumen. Carbon dioxide is the gas produced in the greatest amount." [NB Brody] "Saliva and pancreatic juice both contain 0~-amylase. The activity of this enzyme in saliva is not significant compared with that in the pancreatic juice released into the gut. Release of amylase from the pancreas is controlled by a mechanism similar or identical to the one that stimulates the release of trypsinogen, namely by the influence of CCK on the exocrine pancreas. Amylase catalyzes the hydrolysis of starch at interior positions rather than at the ends of the polymer. This activity yields products such as maltose and longer-chain-length oligomers of glucose. Also, amylase does not catalyze the hydrolysis of starches at branching points. Therefore, small branched-chain structures called dextrins are formed that are not hydrolyzed by the enzyme." [NB Brody] "Dextrins are hydrolyzed by a membrane-bound enzyme, isomaltase, which occurs in the same polypeptide chain as sucrase, the enzyme that hydrolyzes sucrose. Two active sites (catalytic sites) reside on one polypeptide chain. The entire protein is called sucrase-isomaltase. Enzymes containing more than one active site on one polypeptide chain are called multifunctional." [NB Brody] "Lactase, which catalyzes the hydrolysis of lactose, is also a bifunctional enzyme. Lactase resides on the same polypeptide chain as phlorizin hydrolase. The entire protein is called lactase-phlorizin hydrolase." [NB Brody] |
References
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Fatty acids |
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Essential Fatty Acids"Essential fatty acids, or EFAs, are fatty acids that humans and other animals must ingest because the body requires them for good health but cannot synthesize them.[1]... Only two fatty acids are known to be essential for humans: alpha-linolenic acid (an omega-3 fatty acid) and linoleic acid (an omega-6 fatty acid).[2] Some other fatty acids are sometimes classified as "conditionally essential," meaning that they can become essential under some developmental or disease conditions.... Almost all the polyunsaturated fats in the human diet are EFAs. Essential fatty acids play an important role in the life and death of cardiac cells.[22][23][24][25]...Essential fatty acid deficiency results in a dermatitis similar to that seen in zinc or biotin deficiency.[26]:485" (Wiki) |
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References
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Linoleic acid(Essential Fatty Acid) Distribution
Linoleic acid (LA) is a polyunsaturated omega-6 fatty acid.(3)Linoleic acid belongs to one of the two families of essential fatty acids, which means that the human body cannot synthesize it from other food components.(4)(Wiki) Linoleic acid has become increasingly popular in the beauty products industry because of its beneficial properties on the skin. Research points to linoleic acid's anti-inflammatory, acne reductive, and moisture retentive properties when applied topically on the skin.(15)(16)(17) (Wiki) Properties:
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Glycosides |
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"Glycosides are organic compounds of vegetative origin, composed of a sugar component (glycoside, glycone) and a non-sugar component (aglycone, genin). The aglycone forms the main physiologically active part." [Eisenman MPCA] "When ingested, glycosides are readily broken down by enzymes or acids into sugar and aglycone units. The poisonous qualities of glycosides are determined by their aglycones, and the properties of the latter are of ten used to classify glycoside compounds.[CPPlantMush] Although their chemical names can be quite complex, they can be recognized from their trivial names which are formed from the source plant name and the suffix ‘-in’(Mills HMPL) "Specific plant glycosyltransferases (GTs) using nucleotide-sugars as donors can attach specific sugar moieties to an acceptor molecule (Henrissat and Davies, 2000; Jones and Vogt, 2001). Glycosyl hydrolases, so-called glycosidases, remove specific sugar moieties. Most of these enzymes are retaining exo-glycosidases (Coutinho et al., 2003). Some of these glycosidases are also able to synthetically transglycosylate in the presence of high concentrations of an acceptor molecule, a reaction implying the transfer of a sugar moiety from a substrate to an acceptor molecule (Morant et al., 2008)." [Kytidou et al.,2020]
Function"Glycosylation of metabolites in plants serves multiple purposes. Upon glycosylation, hydrophobic metabolites become more water-soluble which improves their bio-distribution and metabolism (Kren and Martinkova, 2001; Pandey et al., 2014). Increased solubility and amphiphilicity of glycosylated metabolites may assist their transport across cell membranes (Vetter, 2000). The attachment of sugars to small metabolites raises their molecular weight and melting point. This allows synthesis and storage of precursors of volatile compounds that can be released on demand after hydrolysis (Ohgami et al., 2015). The stability of glycosylated metabolites may depend on the position where the sugar moiety is attached, for example the 6-O-glucosides of ascorbic acid are chemically less stable than the 2-O-glucoside form or non-glycosylated ascorbic acid (Jones and Vogt, 2001)." [Kytidou et al.,2020]
"The chemical structure of plant glycosides determines their biological action(s) and bioavailability (uptake). In this respect, attention is first paid to glycosylated flavonoids." [Kytidou et al.,2020]
"Many plant flavonoids (see Figure 1 for general structures) are glycosylated (Day et al., 1998; Tohge et al., 2017). Glycosides are linked to the phenolic hydroxyls, via α- or β-D-glycosidic linkages (Murota and Terao, 2003). This type of modification may involve a single oligosaccharide or in some cases a polysaccharide moiety (Xiao et al., 2014). Commonly reported benefits of flavonoid glycosides " [Kytidou et al.,2020] are anti-oxidants and anti-inflammatory activities which find application in prevention and disease management (Lin and Harnly, 2007; Xiao et al., 2014)." [Kytidou et al.,2020]
"Plant-derived cardiac glucosides are secondary metabolites consisting of a steroid backbone functionalized with a lactone ring at the 17-β position and a sugar moiety at the 3-β position ...." [Kytidou et al.,2020] Depending on their chemical nature and structure, glycosides are divided into;
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References
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Hormones
Strigolactones
- Found in; Orobanche, Alectra and Striga genera [Roy PP]
"Strigolactones are signaling compounds made by plants. They have two main functions: first, as endogenous hormones to control plant development, and second as components of root exudates to promote symbiotic interactions between plants and soil microbes. Some plants that are parasitic on other plants have established a third function, which is to stimulate germination of their seeds when in close proximity to the roots of a suitable host plant. It is this third function that led to the original discovery and naming of strigolactones." [Smith, S.M.,2014]
"Strigolactones are made from carotenoids, which in turn are made from building blocks called terpenes or isoprenes. Carotenoids and hence strigolactones can therefore be described as terpenoids or isoprenoids. .... Carotenoids are also precursors of abscisic acid, a hormone that controls the response of plants to environmental stress. The biosynthetic pathway to strigolactones has recently been shown to involve three chloroplast enzymes that convert beta-carotene to a lactone, given the name carlactone [11] .... This is then oxidized in the cytosol of the cell to produce strigolactones. More recently an ATP-dependent transporter protein has been discovered that transports strigolactones out of the cell, either for long distance translocation within the plant or for exudation from roots [12]." [Smith, S.M.,2014]
"Recently, it was shown that strigolactones or derivatives thereof are identical with the postulated shoot multiplication signal (SMS) which regulates apical dominance in vascular plants (Gomez-Roldan et al., 2008; Umehara et al., 2008; Dun et al., 2009)."[Roy PP]
"Lateral bud growth is inhibited by auxins transported down from the shoot apex and by strigolactones transported upwards from the root. However, cytokinins, also transported from root to shoot, can promote bud outgrowth [22]. These different signals are modulated in response to different environmental factors, such as light and nutrients, and are integrated through crosstalk between biosynthesis and signaling pathways...." [Smith, S.M.,2014]
References
- [Smith, S.M.,2014] Smith, S.M. Q&A: What are strigolactones and why are they important to plants and soil microbes?. BMC Biol 12, 19 (2014). https://doi.org/10.1186/1741-7007-12-19
Phenols"Phenolic compounds or polyphenols are the important groups of compounds occurring in plants, where they are widely distributed, and comprising at least 8,000 different known structures (Bravo 1998)." [Charles APSH] |
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"Curcuminoids are ferulic acid derivatives and include three main chemical compounds: curcumin, demethoxycurcumin, and bisdemethoxycurcumin. Curcumin and other phenolic agents similar in structure to curcumin have been shown to stimulate the HO-1 pathway and this most likely accounts for the powerful antioxidant/anti-inflammatory properties of these compounds (Martin et al. 2004; Goel et al. 2008; Surh et al. 2008). Curcuminoids possess unique antioxidant, anti-inflammatory, anticarcinogenic/antimutagenic, antithrombotic, hepatoprotective, antifibrosis, antimicrobial, antiviral, and antiparasitic properties and play important roles in cancer chemotherapy and act by different actions (Huang et al. 1991; Zhang et al. 1999; Rao 2007)." [Charles APSH] "Quinones, especially hydroxyanthraquinones, are natural phenolic antioxidants. Among the hydroxyanthraquinones, purpurin, pseudopurpurin, and alizarin were found to be most effective, while others like emodin, chrysazine, rhein, chrysophanol, and Aloe-emodin, without the ortho-dihydroxy structure, were far less effective (Cai et al. 2006). Natural quinones fall into four categories, that is, anthraquinones, phenanthraquinones, naphthoquinones, and benzoquinones (Cai et al.2004)." [Charles APSH] "Stilbenes are phenolic compounds displaying two aromatic rings linked by an ethane bridge, and exist in the form of oligomers and in monomeric form (resveratrol, oxyresveratrol) and as dimeric, trimeric, and polymeric stilbenes or as glycosides. Resveratrol is a stilbene-type aromatic phytoalexin and is predominantly found in grapes, peanuts, berries, turmeric, and other food products. Resveratrol is a potent antioxidant." [Charles APSH] "Ubiquinone or coenzyme Q is a phenolic conjugated to an isoprenoid chain and is found mainly in the mitochondria (Zubay 1983). Coenzyme Q10, also known as coenzyme Q, ubidecarenone, and ubiquinone, is found in all human cells, with the highest concentrations in the heart, liver, kidney, and pancreas (Wyman et al. 2010). It is a lipophilic molecule present in all tissues and cells that is located mainly in the inner mitochondrial membrane." [Charles APSH] |
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Polyphenols |
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Flavonoids"In the chloroplasts, flavonoids act as primary antioxidants to protect the delicate lightharvesting compounds from ultraviolet and free radical damage. In the human body, these same compounds act as antioxidants, anticarcinogens, and anti-inflammatories by virtue of their radical quenching activities." [BMWH] Flavonols"Flavonols are characterized by a phenolic substitution at position 2 of its 3-hydroxyflavone backbone." [Kytidou et al.,2020]
Quercetin flavones"Whereas flavonols have an OH group at C-3, the flavones bear a hydrogen in that position ...." [Kytidou et al.,2020]
Apigenin Isoflavones"Isoflavones bear a phenolic moiety at position 3 instead of 2 ...." [Kytidou et al.,2020]
Genistein Flavanones"Flavanones are characterized by a saturated C2–C3 bond in the C ring and normally occur as a racemic mixture ...." [Kytidou et al.,2020]
Hesperitin Flavanols (catechins)"Flavanols (a.k.a. catechins)have a 2-phenyl-3,4-dihydro-2H-chromen-3-ol skeleton and are mainly found in tea." [Kytidou et al.,2020]
(+)-Cathechin (C) Anthocyanidins"Anthocyanidins possess a 2-phenylchromenylium ion backbone and are the deglycosylated version of anthocyanins ...." [Kytidou et al.,2020]
Digitoxin | |
Tannins"Tannins are another group of polyphenols with antioxidant and anti-inflammatory effects in human cancer cells (Liu 2004; Aggarwal and Shishodia 2006). Tannins are powerful antioxidant agents because they have many hydroxyl groups, especially many ortho-dihydroxyl or galloyl groups. They are classified into two classes: hydrolysable tannins (gallo- and ellagi-tannins) and condensed tannins (proantho-cyanidins). Proanthocyanidins are dimers, oligomers, and polymers of catechins that are bound together by links between C4 and C8 (or C6). Tyrosol and hydroxy-tyrosol are monophenolic compounds found in olive oil, other edible oils, and wine with antioxidant and pro-apoptotic effects in various human cancer cells. Oleuropein found in olive oil is also important as an antioxidant (Liu 2004; Aggarwal and Shishodia 2006: Colomer and Menendez 2006)." [Charles APSH] Ellagitannins |
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Phenylpropanoids"Phenylpropanoids (PPs) belong to the largest group of secondary metabolites produced by plants, mainly, in response to biotic or abiotic stresses such as infections, wounding, UV irradiation, exposure to ozone, pollutants, and other hostile environmental conditions. It is thought that the molecular basis for the protective action of phenylpropanoids in plants is their antioxidant and free radical scavenging properties. These numerous phenolic compounds are major biologically active components of human diet, spices, aromas, wines, beer, essential oils, propolis, and traditional medicine. Last few years, much interest has been attracted to natural and synthetic phenylpropanoids for medicinal use as antioxidant, UV screens, anticancer, anti-virus, anti-inflammatory, wound healing, and antibacterial agents. They are of great interest for cosmetic and perfume industries as active natural ingredients." [Korkina, L. (2007)] |
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Hydroxycinnamic acidsCinnamic acid |
Cinnamic aldehydesCinnamaldehyde monolignolscoumaryl alcohol PhenylpropenesAnethole
eugenol |
Coumarins"Coumarins are lactones obtained by cyclization of cis-ortho-hydroxycinnamic acid, belonging to the phenolics with the basic skeleton of C6 + C3 (Cai et al. 2004). Coumarins occur in fruits, olive oil, vegetables, wine, and beverages like tea and coffee, and have been shown to have antioxidant and anticancer effects in cells and animal models (Fylaktakidou et al. 2004). The major coumarin constituents are simple hydroxycoumarins (aesculin, esculetin, scopoletin, and escopoletin), furocoumarins and isofurocoumarin (psoralen and isopsoralen), pyranocoumarins (xanthyletin, xanthoxyletin, seselin, khellactone, praeuptorin A), bicoumarins, dihydro-isocoumarins (bergenin), and others (wedelolactone) (Cai et al. 2006). The two adjacent phenolic hydroxyl groups at the C-6 and C-7 positions in the coumarin skeleton were shown to be necessary for the potent antiproliferative and antioxidant effect of esculetin and eight other coumarin derivatives." [Charles APSH]
herniarine FurocoumarinsPsoralen EsculetinAnti-tumor"Many in vivo and in vitro experiments have shown that esculetin has significant anti-tumor pharmacological activities against a variety of tumors, such as colorectal cancer,[43] gastric cancer,[44] hepatocellular carcinoma,[45] oral squamous cell carcinoma,[46] leukemia,[47] endometrial cancer,[48] lung cancer,[49] pancreatic cancer,[50] prostate cancer,[51] laryngeal cancer,[52] malignant melanoma,[53] breast cancer,[54] cervical cancer,[55] osteosarcoma,[56] etc. The anti-tumor mechanism of esculetin mainly included inhibiting tumor cell proliferation by regulating the tumor cell cycle, inducing apoptosis through the mitochondrial pathway, and inhibiting tumor cell migration." [Ting&Kai.,2023] Anti-inflammatory"The anti-inflammatory effects of esculetin have been widely reported in vitro and in vivo." [Ting&Kai.,2023] Immunomodulatory"Studies have shown that esculetin may act on both humoral and cellular mediated immunity. Jeong et al[82]" [Ting&Kai.,2023] Aesculin (6,7-dihydroxycoumarin-6-glucoside)"Most simple coumarins are substituted with OH or OCH3 at positions C-6 and C-7. They often occur in glycosidic form, for example aesculin is the glycoside of aesculetin." [Pengelly TCMP]
Found in: "Pharmacological studies have shown that the anti-inflammatory and anti-oxidative stress effects of esculin are outstanding. This indicates that esculin is promising to be used to treat a variety of diseases closely related to inflammation and oxidative damage. Esculin has anti-diabetic effect, which is closely related to improving pancreas damage, promoting insulin release, and enhancing glucose homeostasis. In addition, esculin has anti-cancer, antibiosis, anti-virus, neuroprotection, anti-thrombosis and treating eye diseases properties. Pharmacokinetic studies show that esculin can be quickly and evenly distributed in the body. However, the first pass effect of esculin is serious. In short, esculin is promising to treat many diseases, but further high quality studies are needed to firmly establish the clinical efficacy of esculin." [Li, Chun‐xiao, et al.,2022] "Aescin, the major active principle from Aesculus hippocastanum (Hippocastanaceae) the horse chestnut tree, has shown satisfactory evidence for a clinically significant activity in chronic venous insufficiency (CVI), haemorrhoids and post-operative oedema. In one controlled trial aescin was shown to be as effective as compression therapy as an alternative to medical treatment for CVI. The therapeutic benefit is well supported by a number of experimental investigations in different animal models, indicative of clearcut anti-oedematous, anti-inflammatory and venotonic properties, mainly related to the molecular mechanism of the agent, allowing improved entry of ions into channels, thus raising venous tension in both in vitro and in vivo conditions. Other mechanisms, i.e. release of PGF2from veins, antagonism to 5-HT and histamine, reduced catabolism of tissue mucopolysaccharides, further underline the wide ranging mechanisms of the therapeutic activity of aescin. The excellent tolerability of aescin in the clinic indicates this treatment is of definite clinical benefit in patients with clinical conditions resulting in CVI, haemorrhoids or peripheral oedema formation." [Sirtori, Cesare R.,2001] ActivitiesAnti-inflammatory"Studies have shown that esculin inhibits the inflammatory response in ulcerative colitis,[11] arthritis,[12] acute lung injury,[13] acute kidney injury,[14] and other diseases." [Ting&Kai.,2023] Anti-tumor"Esculin has been reported to have inhibitory effects on some tumors in vitro, such as lung cancer,[16] breast cancer,[17] and glioblastoma,[18] through regulation of cell cycle, inhibition of tumor cell proliferation, induction of mitochondrial apoptosis, etc." [Ting&Kai.,2023] Antioxidant"...esculin has also demonstrated its antioxidant activity in studies related to acute lung injury,[32] diabetic nephropathy,[33] bioallethrin-induced toxicity,[34] etc. In short, the antioxidant effects of esculin have been widely reported. Its mechanism of action may be due to its direct antioxidant capacity and modulation of oxidative stress-related enzyme activities." [Ting&Kai.,2023] Species examplesHorse chestnut (Aesculus hippocastanum L.)"The coumarin glycoside aesculin was originally implicated as the toxic principle because its hydrolysis product resembled coumarin (see Sweet clover). More recently the toxic effects have been attributed to a group of 30 or more saponins (17)." [Majak SPPWC] melilotsidFound in; |
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"Chromones (and xanthones) are related compounds to coumarines. Sometimes they are present with coumarines in the same plants like in Ammi visnaga." [Mathe MAPW] |
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Glucosinolates |
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"Glucosinolates are sulfur-rich, anionic natural products that upon hydrolysis by endogenous thioglucosidases called myrosinases produce several different products (e.g., isothiocyanates, thiocyanates, and nitriles). The hydrolysis products have many different biological activities, e.g., as defense compounds and attractants. For humans these compounds function as cancer-preventing agents, biopesticides, and flavor compounds." [Halkier et al.,2006] "Plant growth and development are affected by a variety of biotic and abiotic stresses. A multitude of responses are elicited during the adaptation of plants, which include activation of a defense system and a consequent enhanced production of secondary metabolites such as amino acids, sugars, indoles, phenolics, and glucosinolates. Glucosinolates are one of the major metabolites of family Brassicaceae biosynthesized from amino acids and responsible for the flavor and odor of Brassica vegetables. These compounds are induced after wounding and pathogen/insect attack as well as under abiotic stresses such as salt stress, UV radiation, and by plant signaling molecules. Following tissue damage, glucosinolates are hydrolyzed in vivo by endogenous enzymes, myrosinase, to unstable aglycones that further rearrange to a variety of products including isothiocyanates, thiocyanates, and nitriles. Glucosinolate levels and structure are also known to influence host plant suitability for the generalist and specialist herbivore. Levels of these compounds are affected under abiotic stresses including temperature and heavy metal stress." [Bischoff,2021] |
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References
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Peptides |
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"Plants produce antimicrobial peptides (AMPs) to defend themselves against pathogens." [López-García et al.,2012]"As part of their defensive arsenal, they use antimicrobial peptides such as thionins, defensins, lipid transfer proteins, hevein-like peptides, knottins, cyclotides, ß-barrelins, and others." [Villa AC] The repertoire of AMPs synthesized by plants is extremely large, with hundreds of different AMPs in some plant species. In spite of their molecular diversity most plant AMPs share common features: they are basic, amphypatic and cysteine-rich peptides with a stabilized structure by disulfide bonds. Plant AMPs antimicrobial activity is not only against plant pathogens and predatory insects, but also against human viruses, bacteria, fungi, protozoa parasites and neoplastic cells." [López-García et al.,2012] "Antimicrobial peptides (AMPs) are ubiquitous and found as host defenses against pathogens and pests in diverse organisms ranging from microbes to animals [5]. AMPs exist in different molecular forms, although the majority of them are linear peptides from insects, animals, and plants. Nevertheless, bacteria produce polycyclic peptides such as lantibiotics, and all major forms of life produce circular peptides which include bacteriocins from bacteria, cyclotides from plants and theta-defensins from animals [6,7,8,9]. In plants, the majority of AMPs are Cys-rich [10], a feature that enables the formation of multiple disulfide bonds (usually two to six) that contribute to a compact structure and resistance to chemical and proteolytic degradation." [Tam et al.,2015] See also; Thionins"Thionins have been identified from monocots and dicots and are expressed in different tissues, such as seeds, leaves, and roots [35,36,37]. The expression of thionins can be induced by infection with various microbes [38,39] and has been shown to be related to the release of the hormone methyl jasmonate upon plant wounding or microorganism invasion [38,40,41]. Thionins are ribosomally derived and expressed as preproproteins, wherein the prothionin domain is flanked by two conserved sequences, the N-terminal signaling peptide and C-terminal acidic domain [35,38,42]. Mature thionin sequences display more variation than the conserved terminal domains in the preproprotein due to evolutionary pressure [43]. The three-domain precursor of plant AMPs in CRP families is typical and found in other CRP families, including defensins, hevein-like peptides, and knottin-type peptides." [Tam et al.,2015] KnottinsFound in; "Knottins can be found in plants, animal, and fungi and they have toxic, inhibitory, and regulatory functions." [Villa AC] "Knottin is a generic term for small proteins with a particular type of cysteine knot motif known as inhibitor cysteine knot (Isaacs 1995). Cysteine knots require two disulfide bridges that form a circular structure with the protein backbone. The knot is formed when a third disulfide bridge crosses this circular structure. In the case of inhibitor cysteine knots, this third bridge is the one formed by cysteines III and VI". [Villa AC] ß-barrelinsFound in; "The ß-barrelin or MiAMP1 family is present in gymnosperms, angiosperms, and spikemosses, although they seem to be missing in several species with sequenced genomes (Manners 2009)." [Villa AC] "The ß-barrelin precursor proteins have a signal peptide and in gymnosperms expression is induced by fungal attack, supporting an in vivo defensive role (Manners 2009; Sooriyaarachchi et al. 2011)." [Villa AC] "The family has been named ß-barrelins due to the three-dimensional structure of MiAMP1 [a peptide purified from macadamia nuts]. This protein, which is 76 amino acids long, forms a barrel of eight ß-strands that includes three disulfide bonds (McManus et al. 1999). Sequence conservation is high in the family and basic amino acids are abundant." [Villa AC] "The mechanism of action of these peptides against fungi appears to involve binding specifically to ß-(1,3)-glucans in fungal cell walls through conserved polar and aromatic residues (Sooriyaarachchi et al. 2011). The three-dimensional structure of ß-barrelins is very similar to that of the fungal killer toxin HM-1, which interacts with ß-(1,3)-glucans and blocks their synthesis (Kasahara et al. 1994; McManus et al. 1999)." [Villa AC] |
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Polypeptides"Polypeptides refer to the compounds formed by connecting α-amino acids through peptide bonds, generally composed of less than 100 amino acids, and are divided into natural polypeptides and proteolytic polypeptides." [Wang, Wenqi, et al., 2022] "Plant polypeptides are small molecule polypeptides formed by hydrolysis of plant proteins under specific conditions. Common plant polypeptides include oligopeptides, cyclic peptides, cyclic peptide alkaloids, glycopeptides, etc. [1]." [Wang, Wenqi, et al., 2022] "Polypeptide signaling is an emerging field in plant biology, particularly in areas of defense, fertilization, growth, and development. Until 1991, polypeptide hormones and pheromones were thought to be only found in animals and yeast, and it was thought that plants had evolved signaling systems that did not include polypeptide signals. Following the initial discovery in 1991 of the 18-amino acid polypeptide defense hormone systemin and its precursor prosystemin in tomato leaves (6, 9), several plant polypeptide signals have been isolated and characterized or else identified by gene tagging (3, 5, 13, 15)." [Clarence&Pearce,2001] "Because of the low abundance of polypeptide hormones in tissues and organs of animals and plants, their isolations have been typically time consuming and difficult." [Clarence&Pearce,2001] "Bioactive peptides can be endogenous or exogenous. Exogenous bioactive peptides are sequences of amino acids 2–30 in length that are inactive within the parent protein source but are released through the action of proteolytic enzymes during fermentation, hydrolysis, and food processing. These exogenous bioactive peptides have health benefits that go above and beyond basic, human nutrition and they exert “hormone-like beneficial activities” in the consumer if taken in relevant quantities and if they survive breakdown by proteolytic enzymes present in the gastrointestinal tract. Plant-derived bioactive peptides are thought to be a source of health-enhancing compounds and are consumed as part of a healthy, balanced diet. In plants, endogenous biologically active or bioactive peptides have been shown to inhibit insect feeding and act as part of the defense response as well as in cell division control and reproductive mechanisms." [Hayes&Bleakley.,2018]
Found in; Aloe Sp."Results of the separation electrophoresis analysis of extracts prepared from fresh whole leaves and leaf gel of mature Aloe barbadensis Miller plants revealed 23 identifiable different polypeptides. Molecular weights of these polypeptides, calculated from sets of molecular weight reference standards, ranged from 70 000 for the largest to 3000 for the smallest. Electrophoresis profiles of commercially processed and freshly processed Aloe barbadensis Miller and Aloe saponaria Haw leaf gel extracts revealed similar patterns for major peptides. Treatment of mature whole Aloe leaf extracts with acidic and alkaline conditions revealed distinct changes in pH stability of ten peptides. Comparisons of separation electrophoresis profiles of fresh extracts of Aloe whole leaves and of leaf gel portions revealed marked differences in both molecular weights and concentrations of peptides found in extracts from mature, young or immature plants. This report is the first to describe the nature and types of polypeptides detected in extracts of whole leaf, leaf gel, stalk and root portions of immature, young and mature Aloe plants." [Winters et al.,1995] Systemins"The initial polypeptide signal that was identified in plants, systemin, was found in our laboratory during a search for the chemical agent that was responsible for the systemic induction of proteinase inhibitors in tomato leaves. We had found that fractions from crude extracts obtained from tomato leaves activated proteinase inhibitor genes when supplied to young excised tomato plants through their cut stems. We identified the active components as oligogalacturonide fragments derived from plant cell walls." It was "found that oligogalacturonides could activate the synthesis of phytoalexins, which are defense chemicals in soybeans and castor beans. Further research revealed that the oligogalacturonides were not mobile in tomato plants and were therefore not likely candidates for systemic signaling, but are localized signals to help defend against pest and pathogen attacks." [Clarence&Pearce,2001] "Systemin is the only polypeptide ligand in plants for which a receptor has been identified and isolated, for which the elements of a signal transduction pathway are known, and for which several genes regulated by the polypeptide have been identified." [Clarence&Pearce,2001] "Genes coding for systemins have been identified in potato, pepper, and nightshade, but not in tobacco, a more distantly related solanaceous species (2). Tobacco plants also did not respond to tomato systemin, although wounding caused a systemic activation of the synthesis of proteinase inhibitors in tobacco leaves. This wound response utilizes the octadecanoid pathway, similar to wound signaling in tomato plants, with methyl jasmonate being a potent inducer of the defense genes. In searching for the systemic signal in tobacco leaves two 18-amino acid tobacco systemins were recently isolated... that exhibit no homology to tomato systemin." [Clarence&Pearce,2001] "Despite structural differences among the polypeptide defense signals, we propose that plant-derived polypeptides that signal defense genes, locally or systemically, be called systemins. The data so far indicate that systemins and their receptors may be a common feature of plants, but that structurally different systemin polypeptides may serve the same functions in different plant species. Systemins homologous to tomato or tobacco systemins have not been found in species outside the Solanaceae family, but searches for their presence in other species continue." [Clarence&Pearce,2001] Cyclopolypeptides"Cyclopolypeptides are among the most predominant biomolecules in nature, especially those derived from plant seeds. This category of compounds has gained extraordinary attention due to remarkable variety of structures and valuable biofunctions. These congeners display enormous variation in terms of both structure and function and are the most significant biomolecules due to their widespread bioproperties. The estrogenic activity, immunosuppressive activity, cytotoxicity, vasorelaxant activity, and other properties possessed by cyclic peptides from seeds of plants make these congeners attractive leads for the drug discovery process." [Dahiya, Rajiv, et al.,2021] Oligopeptides"An oligopeptide, often just called peptide (oligo-, "a few"), consists of two to twenty amino acids and can include dipeptides, tripeptides, tetrapeptides, and pentapeptides." [1-Wiki] "Amanitins - Cyclic peptides taken from carpophores of several different mushroom species. They are potent inhibitors of RNA polymerases in most eukaryotic species, the prevent the production of mRNA and protein synthesis. These peptides are important in the study of transcription. Alpha-amanitin is the main toxin from the species Amanita phalloides, poisonous if ingested by humans or animals." [4-Wiki] "Phalloidin - A very toxic polypeptide isolated mainly from Amanita phalloides (Agaricaceae) or death cap; causes fatal liver, kidney and CNS damage in mushroom poisoning; used in the study of liver damage." [4-Wiki] Antipain References
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Lectins |
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Lectins"Lectins are carbohydrate-recognizing proteins that bind to cells promoting hemagglutination and antimicrobial effect. Plant lectins have been isolated from bark, cladodes, flowers, leaves, rhizomes, roots and seeds." [Paiva, Patrícia MG, et al.,2010] "The onset of the scientific discipline called “lectinology” dates back to the observation by Stillmark in 1888 that the toxicity of castor bean extracts is linked to the presence of a proteinaceous hemagglutinating factor called “ricin.” Soon after, similar toxins were also reported in other plants." [Damme et al.,2008] "Since the early discovery of lectins, scientists tried to answer the question why (some) plants accumulate blood clumping proteins. Because of the obvious toxicity of the first lectins isolated (e.g., ricin, abrin, Robinia lectin), it was believed that plant lectins are toxins. Though there is no doubt that some lectins are potent toxins, indeed, toxicity is the exception rather than the rule." [Damme et al.,2008] Activity"Cytotoxic effects of lectins may be revealed by antitumoral and antiviral activities and also by deleterious effect on microorganisms (Table 3); lectins of different carbohydrate specificities are able to promote growth inhibition or death of fungi and bacteria." [Paiva, Patrícia MG, et al.,2010] "The inhibition of fungi growth can occur through lectin binding to hyphas resulting in poor absorption of nutrients as well as by interference on spore germination process [58]. The polysaccharide chitin is constituent of fungi cell wall and chitin-binding lectins showed antifungal activity; impairment of synthesis and/or deposition of chitin in cell wall may be the reasons of antifungal action [69]. Probably the carbohydrate-binding property of lectin is involved in the antifungal mechanisms and lectins of different specificities can promote distinct effects. Plant agglutinins are believed to play a role in plant defense mechanism against microorganism phytopathogens [70]." [Paiva, Patrícia MG, et al.,2010] References
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lignin"Lignin is one of the major components of dietary fibre. It is a heterogeneous natural product composed of phenylpropane units and is usually associated with hemicellulose in its native state. Different researchers have demonstrated potential health benefits of this compound. Among them, there is the high activity in binding sodium salt of cholic acid. Antitumour, antiviral and immunopotentiating activities have been attributed to natural and synthetic lignin-related materials, as well as antibacterial and antiparasitic activity. Different experimental results suggest a mechanism whereby the free radical-scavenging activity of lignin in dietary fibre may be involved in the fibre-colon cancer interaction. The ability of dietary fibre to protect against colon cancer has been suggested to be determined by the amount of lignin in dietary fibre as well as the free scavenging ability of lignin." [Mitjans, 2005] lignans"Lignans are widely occurring plant compounds and are closely related to lignin, which forms the woody component of trees and other plants. The lignans are characterized by their dimeric composition from cinnamic acids and which are related biochemically to phenylalanine metabolism. There is a potential use of these compounds as antiviral and antitumour agents. Lignans are being studied for possible use in cancer prevention, particularly breast cancer. Very early evidence suggests that lignans may also be antioxidants, although the strength of their antioxidant activity is not yet clear. Besides their potential use in cancer, preliminary research suggests that lignans may have a role lowering cholesterol. In addition, weak evidence suggests a possible role in preventing atherosclerosis, treating menopausal symptoms, and treating chronic kidney disease." [Mitjans, 2005] "Lignans are formed of 2 phenylpropane units and are mainly present in plants in the free form and as glycosides (Fresco et al. 2006). Main lignan constituents are lignanolides (arctigenin, arctiin, secoisolariciresinol, and matairesinol), cyclolignanolides (chinensin), bisepoxylignans (forsythigenol and forsythin), neolignans (magnolol), and others (schizandrins, schizatherins, and wulignan; pinoresinol and furofuran lignans) (Cai et al. 2004; Surveswaran et al. 2007)....Lignans have been shown to have antioxidant activities and other properties like anti-inflammatory, antibacterial, antiviral, antiallodynic, antiangiogenesis, and antimutagenic." [Charles APSH] podopyllotoxin: "Podophyllum peltatum (podopyllotoxin) (Berberidaceae) is of potent anti- cancer effect. Its derivatives are used in clinical practice." [Mathe MAPW] silybin (flavanolignans): "St’Mary thistle: Sylibum marianum (Asteraceae) has flavanolignans (among them silybin) bearing hepatoprotective effect and used in cases of liver damages." [Mathe MAPW] "Lignanes are present in many plants like in Mistletoe: Vixcum album (Loranthaceae), Siberian ginseng: Eleutherococcus senticosus (Araliaceae) which has adaptogenic effect." [Mathe MAPW] arylnaphthalene lignan lactones"Approximately 59 natural arylnaphthalene lignan lactones and their glycosylated congeners have been isolated from various dietary and medicinal plants and structurally elucidated. The broad spectrum of their pharmacological benefits has also been reported such as antiproliferative, antiplatelet aggregation, antiviral, antifungal, neuroprotective, and anti-inflammatory activities." [Park et al.,2021]
chinensin Aryltetralin lignansPodophyllotoxin: "Podophyllin, an ethanolic extract of Podophyllum peltatum L. or P. emodi Wall (syn. P. hexandnum Royle), is a good source of the aryltetralin-type lignan, podophyllotoxin. The latter compound, as well as its congeners and derivatives exhibit pronounced biological activity mainly as strong antiviral agents and as antineoplastic drugs." [Canel et al.,2000] dibenzylbutaneSecoisolariciresinol dibenzocyclooctadieneSteganacin dibenzylbutyrolactoldibenzylbutyrolactoneMatairesinol furanBelischmins furofuranPinoresinol UnsortedLariciresinol "Chromones (and xanthones) are related compounds to coumarines. Sometimes they are present with coumarines in the same plants like in Ammi visnaga." [Mathe MAPW] |
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References
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Polyacetylenes |
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"Naturally occurring polyacetylenes include all compounds containing two or more conjugated carbon–carbon triple bonds. The term “polyacetylenes” is also often used interchangeably to describe natural products containing a single acetylenic bond if they are formed from polyacetylene precursors. Polyacetylenes are widely distributed, occurring in plants, fungi, lichens, moss, marine algae, and invertebrates. Polyacetylenes are examples of bioactive secondary metabolites that have been considered undesirable in plant foods due to their toxic properties. Some polyacetylenes are known to be potent skin sensitizers, and to be neurotoxic in high concentrations, but are also highly bioactive compounds with potential health-promoting properties. The beneficial effects of most bioactive polyacetylenes from higher plants occur at non-toxic concentrations." [Christensen,2010] "Polyacetylenic compounds have been isolated from a wide variety of organism, comprising plants, both edible and poisonous, from a broad range of families, fungi, marine organisms, as algae, corals, sponges and nudibranchs, and animals, like insects and, in little amounts, humans." [Negri,2015] "In the last 15 years the isolation of polyacetylenic compounds from plants inserted a lot of new entries in the “library” of these metabolites. As previously reported, polyynes have been isolated from a wide range of plant family. During this last period the plant families which gave new polyacetylenes are the Asteraceae, Apiaceae, Annonaceae, Araliaceae, Meliaceae, Campanulaceae, Santalaceae, Torricelliaceae, Olacaceae and Zingiberaceae." [Negri,2015] Bidens Sp."A special feature which separates the Hawaiian group from its realatives is the consistent presence of a phenylthiophene derivative. This is significant in that it supports the biosystematic evidence indicating that all Hawaiian Bidens eveolved from a single ancesteral species." [Marchant, Yu Yoke.,1985] " Leaves and roots of 19 species and six subspecies of Hawaiian Bidens were examined for polyacetylenes. Eleven C₁₃ hydrocarbons, aromatic and thiophenyl derivatives, one C₁₄ tetrahydropyran and three C₁₇ hydrocarbons were isolated and identified. All can be derived from oleic acid. Polyacetylenes were not detected in the leaves of 13 taxa although they are found in the roots of all species. The occurrence of 2-(2-phenylethyne-1-yl)-5 acetoxymethyl thiophene in Bidens has not been previously reported. Most taxa could be distinguished by their complement of leaf and root acetylenes and no variation was found within taxa except in B. torta. There appears to be no taxonomically significant pattern to the distribution of polyacetylenes above the species level in this group." [Marchant, Yu Yoke.,1985] "Phenylheptatriyne (PHT) was detected in two day old seedlings of B. alba, suggesting that polyacetylene biosynthesis begins during germination or soon thereafter. Quantities in the leaves continue to increase up to and beyond 24 days while amounts in the hypocotyls peak at seven days. Relative PHT values in the roots are 100 times higher than those in the aerial tissues for the first 24 days, but there is also a gradual decline in these levels beginning at two weeks and continuing beyond the experimental period. Phenylheptatriyne is absent from the roots of mature B. alba." [Marchant, Yu Yoke.,1985] Solidago altissima"Dehydromatricaria ester (I) was isolated from Solidago altissima L. as a plantgrowth inhibitory substance (7) and regarded as one of the factors for the great propagating power of this plant.(5)" [Ichihara et al.,1978] "Table II shows that dehydromatricarialactone (III) inhibits the growth of the seedlings of barnyard millet as effectively as dehydro-matricaria ester (I) does. However, the season when III appeared in the subterranean stems of S. altissima was confined to the fall of the year and it was scarcely detected in the other seasons, while the amounts of I varied with the months in the range of 0.27 to 0.46 ,Umol/g fresh wt. (Fig. 4). As III can be metabolized into some thioether compounds,13 the decrease of this polyacetylene in the winter may indicate its conversion into other polyacetylenes." [Ichihara et al.,1978] "Solidago virgaurea L., which is nearly related to S. altissima, also contains several polyacetylenes.14 The major polyacetylenes of the former are matricaria ester* and matricaria lactone** which are the dihydro-derivatives of I and ill, respectively. In spite of structural resemblances (between I and matricaria ester and between III and matricarialactone) and a near relationship between both the plant species, the seasonal variation curves of I and ill in S. altissima differed from those of matricaria ester and matricaria lactone in S. virgaurea,14 respectively. Both the species, however, contained the polyacetylenes only in their subterranean parts. It can therefore be presumed that these parts of the genus Solidago are the main sites for polyacetylene synthesis and metabolism." [Ichihara et al.,1978] References
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5-(3-buten-1-ynyl)-2,2'-bithienyl - Tagetes patula [Marchant, Yu Yoke.,1985] a-terthienyl - Tagetes patula [Marchant, Yu Yoke.,1985] C13-ene-tetrayne-ene - Heliantheae: Coreopsidinae [Marchant, Yu Yoke.,1985] Capillin - Artemesia capillaris [Marchant, Yu Yoke.,1985] Carlina oxide - Carlina acaulis [Marchant, Yu Yoke.,1985] Cicutoxin - Cicuta virosa [Marchant, Yu Yoke.,1985] Dehydrofalcarinone - Heliantheae: Galinsoginae [Marchant, Yu Yoke.,1985] Dehydromatricaria ester - Solidago altissima [Ichihara et al.,1978] Ichthyothereol - Ichthyothere terminalis [Marchant, Yu Yoke.,1985] Lachnophyllum ester - Lachnophyllum gossypinum [Marchant, Yu Yoke.,1985] Mycomycin - Nocardia acidophilus [Marchant, Yu Yoke.,1985] Oenanthotoxin Phenylheptatriyne - Bidens alba [Marchant, Yu Yoke.,1985] Tariric acid - Picramnia tariri [Marchant, Yu Yoke.,1985] |
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Polyynes |
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| Polyketids | |
| Steroids | |
Physalinsreferences
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| Saponins | |
aescina blend of saponins [Bajaj MAPS 7] |
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| Terpenes | |
Aucubin"Aucubin is found in common verbena. Aucubin is a monoterpenoid based compound. Aucubin, like all iridoids, has a cyclopentan-[C]-pyran skeleton. Aucubin is found in the leaves of Aucuba japonica (Cornaceae), Eucommia ulmoides (Eucommiaceae), and Plantago asiatic (Plantaginaceae), etc, plants used in traditional Chinese and folk medicine. Aucubin was found to protect against liver damage induced by carbon tetrachloride or alpha-amanitin in mice and rats when 80 mg/kg was dosed intraperitoneally. Aucubin has been shown to exhibit anti-proliferative and apoptotic functions. Aucubin has shown effectiveness as antifungal and suggests its promising potential use as solution for C. albicans biofilm-related infections. Aucubin has a range of biological activities, including anti-inflammatory, anti-microbial, anti-algesic as well as anti-tumor activities." References
Betulin"Betulin, belonging to lupane class, is the most abundant triterpenoid in the nature, which is the precursor of betulinic acid found in plant species of the Betulaceae family. For instance, the bark of hazel (Corylus avellana), hornbeam (C. betulus) and a number of Alnus species are the main source of the compound." [Saeidnia, NANAD] "The compound is used in cosmetic products and its derivatives are applied in production of plastic materials. Betulinic acid exerted cytotoxic activity toward neuroblastoma cells, glioblastoma and melanoma cell lines." [Saeidnia, NANAD] Cucurbitacins "Cucurbitacins are extremely bitter and toxic tetracyclic terpenoids (lanostane derivatives) associated primarily with Cucurbitaceae family. These are also reported from plants belonging to other families like Brassicaceae, Begnoniaceae, Datiscaceae, Euphorbiaceae, Rosaceae and Labiaceae. At least sixteen species of the genus Ibris are known to produce this class of compounds, 12 of these contain cucurbitacin E and I reported as antifeedant against flea beetle, Phyllotreta nemorum (Linnaeus). Iberis amara, like most other crucifers, contains sulphur-containing glucosinolates, which act as oviposition and feeding stimulants. However, the plant is rejected by insects due to occurrence of specific cucurbitacins-I and II (158, 159) (Sachdev-Gupta et al. 1993)" [Koul PB] Antifeedant: "The Diabroticite phagostimulant and arrestant cucurbitacins (Metcalf et al. 1980), antifeedant to most other insects (Tallamy et al. 1997a), are present in cucurbit anthers and other flower parts (Anderson and Metcalf 1987) but absent from pollen.... The usefulness of Diabroticites as model pest insects for taste receptor research derives from their i) diverse host plant associations, ii) extreme larval-to-adult host species shifts, iii) global agricultural pest status, iv) high and uniform sensitivities to the most potent animal phago-stimulants and -deterrents (e.g. cucurbitacins and azadirachtin), and v) their ease of behavioural and electrophysiological testing relative to gustation (Mullin et al. 1994). These chemoreception studies benefited from simultaneous comparison of structure-activity relationships for both feeding stimulants and deterrents using complete dose-response ranges, since stimulants can become antifeedants at high doses.... The strong phagostimulatory action of cucurbitacins on adult Diabroticite beetles has led to their use in baits laced with small amounts of carbaryl (Metcalf and Metcalf 1992) that are now marketed (e.g. Slam® and Adios® from BASF Corp. formerly MicroFlo Co.; Compel® from Ecogen, now Monsanto Co.). These baits have sufficient efficacy to manage vectoring of bacterial wilt by Diabroticites (Fleischer and Kirk 1994).... Cucurbitacin baits based on dried buffalo gourd, Cucurbita foetidissima HBK, powder greatly reduce insecticide inputs for rootworm control, and, as a chemical mixture in contrast to a single component, may retard the development of gustatory habituation and insensitivity, and are antifeedant for many non-target species (Tallamy et al. 1997a). Baits incorporating cucurbitacin phagostimulants specific for adult Diabroticites are effective alternatives to soil insecticides used for larval control." [Koul PB] Herbivore Adaptations to curcurbitans: " An interesting behavioural aspect relates to the canalicular defenses wherein plant secretion stored within canal systems interferes with foraging by nonadapted caterpillars. Adapted species overcome this by cutting trenches. Petiole constriction and trenching behaviour are well evident in the danaine caterpillars, which feed not only on closely related Apocyanace and Asclepidaceae, but also on the Moraceae; all the three groups producing alkaloids, pyridines and cardenolides. Similarly, beetles of the genus Epilachna have shown the trenching behaviour cucurbitaceous hosts to prevent an influx of bitter cucurbitacins at the feeding site (Doussurd 1993)." [Koul PB]
Local Species Anagallis arvensis - Scarlet Pimpernel; "Cucurbitacins: including cucurbitacins E, B, D, I and L" Hazards "Large doses or long-term administration could lead to gastroenteritis and nephritis, due to the cucurbitacins content of the drug." [PDR] Distribution
"Cucurbitacin C is found only in C. sativus (Enslin and Rehm 1958)." [EMNMPV.2] Activities
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waxes |
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Index |
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