Practical ecological knowledge for the temperate reader.


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.




Fatty Alcohols
Cicutoxin Falcarinol Oenanthotoxin
Sugar Alcohols


"Beside amatoxins, cicutoxin is the most lethal plant toxin in North America. Cicuta toxicity is one of the best described serious plant poisonings in the American literature. Between 1900 and 1975, Starrevekl and Hope identified 83 cases of Cicuta poisoning with an overall mortality rate of 30%.5" [Barceloux MTNS]






"Within fifteen to thirty minutes of ingesting Cicuta root, the victim experiences sharp stomach pains, vomiting, rapid pulse, dilated pupils, dizziness, diarrhea, and finally convulsions so powerful that he or she often bites off the tongue and shatters teeth. Death comes from respiratory failure after complete paralysis. Thirty to 50 percent of Cicuta poisoning leads to death." [David E. Jones]

"Symptoms of poisoning, following the initial stupor and nausea, include severe tonic-clonic spasms, unconsciousness, canosis and extremely widened pupils. Death occurs through asphyxiation at the peak of a convulsive attack or through heart failure." [PDR] "Patients with Cicuta intoxication may develop seizures suddenly; therefore, intravenous access should be established and all patients should be monitored for cardiac dysrhythmias, hypotension, and hypoxia." [Barceloux MTNS]

"Early muscarinic effects are localized to the gastrointestinal tract.44,46 Systemic muscarinic effects (bronchial secretions) leading to respiratory distress may occur. However, pathognomonic of severe cicutoxin poisoning are violent multiple major motor seizures.42-46 The symptoms may begin within 30 minutes after ingestion.46" [PTH]

"Forced diuresis, hemodialysis and hemoperfusion are initiated as treatment for poisonings. Gastric lavage should only be carried out under anesthetic because of the danger of convulsion. Benzodiazepine or barbiturates are used to lessen the effects of the spasms." [PDR]

"The presence of vomiting limits the efficacy of decontamination measures. Additionally, the potential for rapid onset of changes in consciousness and seizures during serious water hemlock intoxication increases the risk of using decontamination measures. Consequently, most of these ingestions require no decontamination measures." [Barceloux MTNS]

"Gastrointestinal decontamination with activated charcoal may be beneficial in patients with recent ingestions. Otherwise, the cornerstone of therapy is aggressive supportive care....Provide symptomatic and supportive therapy; manage seizures with diazepam or lorazepam; recurring seizures may need barbiturate or phenytoin treatment, general anesthesia may be required for seizure control; sodium bicarbonate can be given for acidosis.... Hemodialysis was useful in one case report" [PTH]

Dermal Absorption

"Although most cases involve ingestion, a case report suggests the possibility that dermal absorption of the toxin occurs following direct contact with the juice from plant parts. In 1911, Egdahl reported two deaths from the use of Cicuta extracts as a topical antipruritic agent.9 However, the report lacked descriptive and laboratory data, and there are no other clinical or experimental data to determine the extent of dermal absorption of toxins in water hemlock." [Barceloux MTNS]

Effect on Animals and Livestock

"Due to the acute nature of the poisoning, animals are often found dead not far from the habitat of the plant, where the plant’s roots may have become exposed following a previous drop in the water level [27]. There are no characteristic pathological findings postmortem. Incidents, mainly involving cattle, occur sporadically in the Nordic countries [27]." [Kuete TSAMP]



(polyacetylene alcohol) [Polya BTPBC]


"Falcarinol (sometimes called panaxynol) and the structurally related panaxytriol are also characteristic polyacetylene components of ginseng (Panax ginseng; Araliaceae; see page 245)." [MNP Dewick]

"Poliacetylenic compounds are frequently found in Umbelliferae [29]. Several genera among the Araliaceae and Apiaceae families (which include many common plants and species from Hedera, Schefflera, Panax, Apium, Falcaria, Daucus, Oenanthe, and others) have been shown to contain falcarinol [30], isolated from Falcaria vulgaris by Bohlmann. A polyacetylene compound, panaxynol, was isolated by Takahashi from Panax ginseng roots [31]. The chemical structure of the compound was identical to that of falcarinol and also to that of carotatoxin, isolated from Daucus carota [32]" [Rahman SINPC]

"The domestic carrot (Daucus carota), for example, contains four polyacetylenes, the major one being falcarinol (Lund and White, 1990), which is a mild neurotoxin found only to be present in 2 mg·kg–1 (dry weight) of carrot roots." [T&F NPP]


Hedera helix L.: "The contact with leaves and extracts can induce dermatitis due to the presence of falcarinol and its derivatives.10,24 These reactions can arise either as simple irritations, i.e., without an involvement of the immune system, or in the form of contact allergies, entailing an activation of the immune system.11,14,25,30 However, these problems normally do not arise at the doses used in products for skin care." [Burlando HPC] "The frequent use of ivy-based products can cause allergic reactions and nausea. Side effects are due mainly to to falcarinol." [Capasso PQR]


"New research is looking at the effects of another phytonutrient in carrots, called falcarinol, and its ability to reduce the risk of colon cancer." [Torkos CENM]

"Aliphatic C(17)-polyacetylenes of the falcarinol type, which occur in common food plants of the Apiaceae family such as carrot, celeriac, parsnip, and parsley, have demonstrated interesting bioactivities, including antibacterial, antimycobacterial, and antifungal activities as well as anti-inflammatory, antiplatelet aggregatory, neuritogenic, and serotonergic effects. In addition, the cytotoxicity of falcarinol-type poly-acetylenes toward human cancer cells, bioavailability, and their potential anticancer effect in vivo indicate that these compounds may contribute to the health effects of certain vegetables and hence could be important nutraceuticals (Christensen, 2011; Christensen and Brandt, 2006)." [Verotta CIWWS]

"Studies have indicated the beneficial impact of eating vegetables and fruits on human health in preventing chronic diseases including cancer, which is one of the major causes of death around the world [1]. Polyacetylenes (PAs) are a class of chemicals defined by the presence of two or more carbon–carbon triple bonds in the carbonic skeleton [2]. Falcarinol-type PAs are biologically active compounds that are widely found in plants in the Apiaceae family, such as carrots, celery and parsley, and the Araliaceae family, such as ginseng. Carrot is the main dietary source of polyacetylenic oxylipins, including falcarinol (FaOH), falcarindiol (FaDOH) and falcarindiol 3-acetate (FaDOH3Ac)..., with FaOH serving as the intermediate metabolite of PA, from which the other forms are generated [3,4,5]." [Alfurayhi et al.,2023]

"Natural PAs from diverse food and medicinal plants and their derivatives exert multiple bioactivities, including anti-inflammatory properties [41]. PAs can impact inflammation through known and unknown pathways. Evidence supports that PA compounds improve human health by stimulating anti-cancer and anti-inflammatory mechanisms [3]. These PAs contain triple bonds that functionality convert them into highly alkylating compounds that are reactive to proteins and other biomolecules. This unique molecular structure might be the key to understanding the beneficial effects of PAs such as their anti-inflammatory and cytoprotective function [41]. Recent research has suggested that the anti-cancer role of certain foods might be attributed to their anti-inflammatory function. Root vegetables, and particularly carrots, are promising natural sources in this respect thanks to their rich content of PAs [3,41,42,43]." [Alfurayhi et al.,2023]

"The expression of the inducible nitric oxide synthase (iNOS) is one of the direct consequences of an inflammatory process. Early studies have focused on the potential toxicity of the ensuing high-output NO-synthesis serving as a means to eliminate pathogens or tumor cells but also contributing to local tissue destruction during chronic inflammation. More recently, however, data are accumulating on a protective effect of high-output NO synthesis and - equally important - on a gene-regulatory function that helps to mount a protective stress response and simultaneously aids in down-regulating the proinflammatory response. These findings appear to contrast to the often observed sustained iNOS-expression during chronic inflammatory diseases, as for instance in Psoriasis vulgaris and other conditions with a chronic Th1-like reactivity." [Suschek et al.,2004]

Enzyme/process inhibited or activated (other targets) / in vivo effects/ : "[Reduces] iNOS expression (5-LOX) [blocks LPS-induced macrophage iNOS expression, dermatitic]" [Polya BTPBC]

Larval Attractant: Psila rosae - Larval attraction - Jones and Coaker (1979), Maki et al. (1989); Stàdler (1971/1972) [Rosenthal HerbV2]

Misc Studies

"In the following experiments carrot roots were exposed to various sources of ultraviolet light in the laboratory and set aside to allow time for enzyme synthesis. ... falcarinol and falcarindiol concentration changes did not appear to be related to the ultraviolet light used in this study." [Waller Allelochemicals]

"Falcarinol and falcarindiol concentration changes are small com­ pared to those in myristicin and 6-MM content, and do not appear re­ lated to radiation (Table II). These polyacetylenes are present in fresh carrots. Immediately upon wounding, they are translocated to the surface through oil ducts (3), and, therefore, their function as phytoalexins apparently does not depend upon de novo synthesis." [Waller Allelochemicals]

"A four-year study of field-grown commercial carrot roots revealed that recently harvested, unprocessed carrot roots contained 24 ppm falcarinol and 65 ppm falcarindiol (8)." [Waller Allelochemicals]

Related Compounds

Dendropanax arboreus: "The major compound responsible for the in vitro cytotoxicity was falcarinol. Several other known compounds were isolated and found to be cytotoxic, including dehydrofalcarinol, a diyenne, falcarindiol and dehydrofalcarindiol." [PTFC]

Dehydrofalcarinone and dehydrofalcarinol were identified in the essential oil of Artemisia capillaris [Tang CDPO]
"The distribution of volatile components in different parts of the plant was also described. Thus, the main volatile components (% of total) in fine stem and leaves were capillene (26%), capillarin (14%), dehydrofalcarinol (9%), and p-caryophyllene (7%); the main volatile components in stem were dehydrofalcarinol (43%), dehydrofalcarinone (14%), and capillene (8%); the main volatile components in roots were dehydrofalcarinol (67%)..." [Tang CDPO]



Sources: Hemlock Water Dropwort - Oenanthe crocata [T3DB]

"belongs to the class of organic compounds known as long-chain fatty alcohols. These are fatty alcohols that have an aliphatic tail of 13 to 21 carbon atoms." [T3DB]

"The main toxic constitutent of hemlock water drop-wort is oenanthotoxin - an unsaturated higher alcohol (C17H2202) which was purified by Clarke.2 It resembles cicutoxin which is the toxic principle in water hemlock. Oenanthotoxin concentration in the plant roots is highest in winter and spring, and ingestion of very small amounts may prove fatal." [Ball et al.,1987]


"Cicutoxin from the water hemlock (Cicuta virosa; Umbelliferae/Apiaceae) and oenanthotoxin from the hemlock water dropwort (Oenanthe crocata; Umbelliferae/Apiaceae) are extremely toxic to mammals, causing persistent vomiting and convulsions, leading to respiratory paralysis. Ingestion of the roots of these plants may frequently lead to fatal poisoning." [MNP Dewick]

"... oenanthotoxin is a poison that gives epilepsy-like convulsions." [Sandberg NR]

"It appears that the fatal quantity of oenanthotoxin may be as low as 10 to 20 mg, which is contained in about 20 grams of the 0. crocata root." [Ball et al.,1987]

Treatment of Poisonings

"In rabbits pentobarbitone reduces the convulsive effects.3 Barbiturates have been used in patients poisoned by cicutoxin4 and successful treatment with large doses of thiopentone has been described.5 Ten grams of thiopentone was administered in 24 hours to our patient with oenanthotoxin poisoning and this successfully depressed cerebral electrical activity." [Ball et al.,1987]



First found in the ripe berries of the mountain ash Pyrus aucuparia Ehrh. (L.) (Sorbus aucuparia L.), Rosaceae. Occurs also in many other berries (except grapes) and in cherries, plums, pears, apples, seaweed and algae. Has been detected in blackstrap molasses. Isoln from berries: Embden, Griesbach, Z. Physiol. Chem. 91, 268 (1914). Prepd industrially from glucose by high pressure hydrogenation or by electrolytic reduction. [Merck]

Properties: Sweet taste, ~60% as sweet as sugar (w/w). In the healthy human organism 1.0 g of sorbitol yields 3.994 calories which is comparable to 3.940 calories from 1.0 g of cane sugar. Seventy percent of orally ingested sorbitol is converted to CO2 without appearing as glucose in the blood.
Freely sol in water (up to 83%). High % sorbitol solns are much more viscous than corresp glycerol solns. Quite sol in hot alcohol, sparingly sol in cold alcohol. Also sol in methanol, isopropanol, butanol, cyclohexanol, phenol, acetone, acetic acid, DMF, pyridine, acetamide solns. Practically insol in most other organic solvents. Not attacked in the cold when mixed with dil acids, alkalies or mild oxidizing substances. [Merck]

Most bacteria are unable to use sorbitol for energy, but it can be slowly fermented in the mouth by streptococcus mutans, a species of bacteria that cause tooth decay unlike many other sugar alcohols such as isomalt and xylitol, which are considered to be non-acidogenic.[9][10] [Wiki]

Hazards: "Ingesting large amounts of sorbitol can lead to abdominal pain, flatulence, and mild to severe diarrhea. Habitual sorbitol consumption of over 20 grams (0.7 oz) per day as sugar-free gum has led to severe diarrhea, causing unintended weight loss or even requiring hospitalization.[33] In early studies, a dose of 25g of sorbitol, eaten through the day, produced a laxative effect in only 5% of individuals.[34] As a result of the large molecular weight of sorbitol, when large amounts of sorbitol are ingested, only a small amount of sorbitol is absorbed in the small intestine, and most of the sorbitol enters the colon, with consequent gastrointestinal effects.[30]" [Wiki]

Use: In manuf of sorbose, ascorbic acid, propylene glycol, synthetic plasticizers and resins; as humectant (moisture conditioner) on printing rolls, in leather, tobacco. In writing inks to insure a smooth flow and to prevent crusting on the point of the pen. In antifreeze mixtures with glycerol or glycols. In candy manuf to increase shelf life by retarding the solidification of sugar; as humectant and softener in shredded coconut and peanut butter; as texturizer in foods; as sequestrant in soft drinks and wines. Used to reduce the undesirable aftertaste of saccharin in foodstuffs; as sugar substitute for diabetics. Pharmaceutic aid (flavor; tablet excipient); to increase absorption of vitamins and other nutrients in pharmaceutical preparations [Merck]

Melting point: mp 110-112° [Merck] 94-96°C [1-Wiki] 97-112°C [ChemSpider]
Boiling point: 494.9oC [ChemSpider]
Solubility: Water 36mg/ml (MedChem Express) [ChemSpider]

Therap-Cat: Laxative.[Merck]

Therap-Cat-Vet: In ruminant ketosis, osmotic diuretic, laxative. [Merck]



"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.
In general, annual plants contain larger amounts of alkaloids than do perennials. Trees tend to have small amounts of alkaloids, usually of simpler structure." [MHC Hoffman]







(Quinolizidine Alkaloid)




Cystisine is rapidly absorbed and excreted and consequently clinical signs of poisoning occur rapidly after a toxic dose of the seeds are consumed. Equally, the signs are relatively short – lived due to rapid excretion of the alkaloid. Cytisine binds strongly to nicotinic receptors, causing initially stimulation and at higher doses blockade of the ganglionic receptors similar to the effects of curare.[DP2]


Husemann and Marme isolated in 1864 an alkaloid, cytisine, a white, crystalline solid,of a bitter, somewhat caustic taste, soluble in water and alcohol, but scarcely at allsoluble in ether, chloroform, benzene, or carbon disulphide. The same alkaloid hasbeen isolated from the seeds of several plants of the Papilionaceous group. A second alkaloid,laburnine, was also announced by them. (Chem. News, July 16, 1869, 36.)Partheil (A. Pharm., 1892, 448) has since studied cytisine, and gives it the formula C11H14ON2, which has been adopted by other authorities. Ferric chloride colorscytisine and its salts blood-red, which color, however, disappears on diluting withwater or on addition of hydrogen dioxide. If after the addition of this latter reagent themixture is heated gently in the water bath an intense blue color is developed. When cytisine is distilled with soda lime, pyrrol is obtained, besides a base, C9H13N, which ispossibly a hydroquinoline. A. Kannerda purified crude cytisine, obtained from theseeds of Cytisus Laburnum L., by the well known shaking out process withchloroform, by distilling it in a partial vacuum. Under a pressure of 2 mm. and a temperature of 228o C. (442.4o F.), the alkaloid distils over as a colorless liquid andcongeals in the receiver in the form of fine crystalline needles. It separates fromabsolute alcohol in the form of small transparent rhombic crystals, which have thesp. gr. 1.0046. (Ap. Ztg., July, 1900, 486.) [Remington USD20]

"Cytisine (Ulexine, Baptitoxine, Sophorine), The preparation of the alkaloid has been described by Ing.1 It forms rhombic crystals, m.p. 153o, b.p. 218o/2 mm., [a]"o - 119-6o (H20), is soluble in water, alcohol or chloroform, but nearly insoluble in ether or benzene. It is a strongly alkaline base and forms well-crystallised, deliquescent salts..." [TPA Henry]


"...Luo et al. (1997, 1999) found that the LC50 values against L. erysimi for the three alkaloids, cytosine, anabasine, and nicotine (the latter two as controls), were 432.59, 648.70, and 1090.65 mg/ml, respectively, 48 h after treatment using the cage-dip method, and the results again indicate that cytisine is the most toxic alkaloid against the aphid. Luo et al. (1997) also tested the efficacies of the eight alkaloids from the two extracts of S. alopecuroids on apterous L. erysimi. Results indicated that cytisine was the most effective alkaloid with 96.7 and 100% mortality at 1000 and 2000 P(A)(mg/ml) 48 h after treatment, and the second most effective alkaloid is aloperine which gave much lower mortality, 43.3 and 45.0% at the two concentrations, respectively. All others had little activity on the aphids with 5.0–36.7% mortality. [Rai NOBC]

"Luo and Zhang (2003) studied the effects of the seven alkaloids from S. alopecuroids on metabolic esterases of the larvae of P. xylostella. Their results indicate that cytisine and aloperine could inhibit carboxylesterase activity through noncompetitive inhibition. Sophoramine, sophoradine, matrine, oxymatrine, and cytisine could inhibit the activity of acid phosphoresterase, and cytisine could also weakly inhibit the activity of alkaline phosphoresterase. In addition, three alkaloids, cytisine, sophoramine, and sophocarpine could inhibit the activity of glutathione-Stransferase [glutathione transferase] in P. xylostella larvae." [Rai NOBC]

Ritual Use

"Cytisine, an alkaloid that formed the basis for the former hallucinogenic use amongst some North American Plains Indians of seeds of the leguminous Sophora secundiflora (53), has been isolated from leaves and beans of Genista canariensis." [Ethsearchpharm]

"Sophora secundiflora was employed in northern Mexico until recently in certain ceremonies, but, as in the southwestern United States its use as an intoxicant has disappeared. According to the Stephen Long expedition of 1820, the Arapaho and Iowa tribes were using the large red beans as medicine and a narcotic. A well-developed mescal bean cult existed amongst at least 12 tribes of the United States. There are so many parallels between the peyote cult and the former Red Bean Dance that the origin of the ceremony must have had a southern or Mexican origin." [Helaine_Selin]

"The active principal of S. secundiflora is cytisine which is common in the legume family. This alkaloid belongs to the same group as nicotine; it is a strong poison, attacking the phrenic nerve controlling the diaphragm. Death can occur from asphyxiation. It may possibly be because of the great danger in cases of overdosing with the red bean that its ceremonial use has disappeared. It is of interest, however, that the “roadman” or leader of the peyote ceremony today always wears a necklace of the red beans during the peyote ceremony, undoubtedly as a reminder of a once sacred plant." [Helaine_Selin]

"All parts of Canary Island broom contain cytisine, the poisonous alkaloid also found in the mescal bean, Sophora secundiflora, of which I will write more in Book Two. Richard Evans Schultes (Schultes and Hofmann 1980) says that hallucinogenic activity for cytisine has not been demonstrated. But the use of the mescal bean as an entheogen is well documented, dating back at least 8,000 years. It is also quite possible (and I think likely) that the reported effects of Cytisus canariensis are not due to cytisine, but to some other substance, such as a terpene. All of the brooms deserve more study. Christian Ratsch (1992) states thatYaqui magicians also use the seed capsule to prepare a divinatory drink used for time travel (effects that are likely to be from cytisine and the other alkaloids). He also writes that the blossoms are mixed with marijuana for an aphrodisiacal smoke used in sexual magic circles." [Pendell PPPHC]

"Mescal beans are the psychotropic seeds of Sophora secundiflora and are not associated with the peyote cactus that is also sometimes known as mescal... This small tree or evergreen shrub is native to Texas, New Mexico, and Mexico. The pods contain up to eight seeds, which are maroon or orange-red in color. The principal alkaloids contained in the seeds are cytisine, N-methylcytisine, and sparteine.
Despite the use of mescal beans in Native American vision quests, none of these alkaloids are known to have hallucinogenic properties. Depending on the amount consumed and the method of preparation, mescal beans can cause a range of effects, from vomiting, headaches, and nausea to intoxication, stupor, and even death. Mescal beans are usually consumed in a decoction. Some 30 Native American peoples have made use of mescal beans, almost all of them using the beans for their decorative value; less than half of them have used mescal for its psychoactive effects. Mescal beans have been found at archaeological sites dating back to 7,000 14C years ago, in Texas, New Mexico, and Mexico, where they may have been used for ornamental purposes." [Prance CHP]



"Muscarine, the best-known alkaloid of Amanita muscaria, has a very important place in pharmacology because it was the first drug known to have a selective action on organs innervated by the autonomic nervous system." [ACP23]

"Early attempts to isolate the active toxic principle of fly agaric and of other fungi were unsuccessful. The first preparations were heavily contaminated with choline and acetylcholine." [ACP23] "Although the search for the toxic principles of A . muscaria started at the beginning of the 18OOs, attempts to obtain pure muscarine were not successful until 1957." [ACP40]

"The first pure crystalline muscarine chloride was obtained by Eugster and Waser (2). Muscarine and other bases were precipitated from the alcoholic extract of Arnam'ta rnuscaria with Reinecke acid. The salts obtained were decomposed to the chlorides by the Kapfhammer method, and the chlorides were chromatographedon cellulose columns with different elution systems. The homogeneity of the fractions were tested by controlled toxicity tests and colorimetric methods. From 124 kg of mushrooms, 260 mg of pure muscarine chloride was isolated." [ACP23]

"The binding affinity of muscarine with the acetylcholine receptor is so high that the compound is routinely used to study cholinergic pharmacology.". [ACP40]

"Muscarine acts by binding to acetylcho-line receptors associated with the autonomic nervous system, which controls involuntary muscle actions and glandular secretions such as tears. When acetylcho-line binds at a receptor site, it triggers an action and then is rapidly degraded, which removes the stimulatory effect. When muscarine binds to a site, it too acts as a trigger but is not degraded quickly, so its effects continue much longer than those of acetylcholine. Atropine, which is an effective antidote, acts by displacing the muscarine without triggering the receptors." [Trudell MPNW]

"The symptoms of muscarine poisoning begin about 5 to 30 minutes after the mushrooms are eaten. Profuse sweating is the most frequent symptom, often accompanied by salivation and lacrimation (production of tears); an alternate name for this type of poisoning is PSL syndrome (for perspiration-salivation-lacrimation). The victim may experience blurred vision and feel nauseated, and abdominal pain, vomiting, and diarrhea often occur. Less often, victims show constriction of the muscular region at the back of the mouth, a painful urge to urinate, difficulty in breathing due to constriction of the bronchial region or blockage of airways by mucus, and decreased heart rate and blood pressure. The alkaloid atropine quickly blocks the effects of muscarine and recovery often occurs within 30 minutes. Without treatment, the symptoms can persist for many hours before disappearing." [Trudell MPNW]



Steroidal Alkaloids

"...steroidal alkaloids possess a number of additional biological activities such as antifungal, moluscicidal, and insecticidal properties. All these effects are most likely based on the saponin-like structure, in particular of the glycoalkaloids which will allow strong interactions with membranes, thus inflicting membrane damage (Roddick 1987)." [Bajaj MAP4]

"In general, the steroidal alkaloids represent an important class of alkaloids that essentially afford a close structural relationship to sterols i.e., they contain a perhydro-1, 2-cyclopentanophenanthrene nucleus. Interestingly, these group of alkaloids invariably occur in the plant kingdom as glycosidal combination with carbohydrate moieties. The steroidal alkaloids may be broadly classified into two major groups, namely: (a) Solanum Alkaloids, and (b) Veratrum Alkaloids." [PCPB]

Tomatine, solasonine and solamargine have all demonstrated insecticidal properties.16 Powdered, whole Tomato plants have excellent insecticidal properties and were used for this purpose in China. In particular, tomatine was shown to be very effective against red flour beetle larvae and tobacco hornworm. In Indonesia, an infusion of tomato leaf has been successfully deployed as a spray against cabbage caterpillars (Weissenberg 1998). Tomatine is lethal to snails (Lymnaea cubensis and Biomphlaria glabratus) that are the vectors responsible for diverse protozoal infections, including schistosomiasis – suggesting a possible molluscicidal role for this compound (Freidman 2002). [Cheryll_Williams]

The presence of glycoalkaloids in the diet may not be all bad news. Their anticancer potential has been an interesting subject for investigation. A range of vegetable-derived glycoalkaloids have demonstrated an inhibitory effect on tumour cells (colon and liver cancer) (Friedman 2006; Lee 2004): [Cheryll_Williams]

It should be noted, however, that the glycoalkaloid component of the true Tomato (Lycopersicon esculentum) is quite different to that of Australian ‘bush tomatoes’, which belong to the genus Solanum. The latter tend to contain the toxic glycoalkaloid solasodine in the unripe berries – although as they ripen they often (but not always) become edible. This is because glycoalkaloids are synthesised, sequestered and degraded at different stages of plant growth. [Cheryll_Williams]

...glycoalkaloids are poorly absorbed from the gastrointestinal tract and undergo detoxification during the digestive process. The safe glycoalkaloid content in potatoes is considered to be 20–100 mg per kg (Frohne & Pfander 1984; Friedman 2006). [Cheryll_Williams]

Toxic effects of steroidal alkaloids on livestock and man were repeatedly reported and experimentally confirmed. A teratogenic activity was assigned to these compounds (Keeler 1975). In laboratory experiments, a single dose of solasodine (1.2 g/kg) given to pregnant hamsters produced spina bifida, exencephaly, and cranial bleb. Tomatidine and diosgenin were not teratogenic (Keeler et al. 1976). [Bajaj MAP4]


"Outbreaks of poisoning from potatoes have been associated with higher than normal concentrations of glycoalkaoids (?-solanine and ?-chaconine) in the tubers and sprouts. While such incidents have generally involved green-skinned tubers, certain varieties can habitually contain high levels of toxic alkaloids." [Cheryll_Williams]

"Unfortunately glycoalkaloids are heat stable, which means they can survive cooking under high temperatures. Losses in cooking are minimal: boiling (4.7% loss), microwaving (15% loss) and deep-frying (nil loss), although during frying longer cooking times at temperatures around 210o C will reduce glycoalkaloid levels. However, the cooking oil itself retains the glycoalkaloids, which can easily migrate back into the potato - accounting for a wide variability of exposure depending of whether cooking oils are regularly changed. Unpeeled potatoes will retain their toxicity no matter what type of cooking process is used because the highest alkaloid levels are located within the 1 mm from the outside surface, the content decreasing toward the centre of the tuber." [Cheryll_Williams]


(Steroidal Alkaloid)






(Steroid-derived alkaloid)




See also: Vinca Alkaloids page [page created]

Indole alkaloid (distinctively a tryptamine) [Arora MPB]


Vincamine is a monoterpenoid indole alkaloid found in the leaves of Vinca minor, comprising about 25-65% of the indole alkaloids found in Vinca minor by weight. [Wiki-1] V. minor & V. major; It contains the alkaloid 'vincamine', which is used by the pharmaceutical industry as a cerebral stimulant and vasodilator[238].(PFAF) Various Erowid user reports from taking store-bought capsules mention subtle mental stimulation and clarity of thought.[2] [Erowid]

"...finds general use as an aid in activities requiring highly focused attention and concentration such as technical writing or computer operation. Vincamine has also been indicated in the treatment of tinnitus or ringing in the ears and for the treatment of poor memory. Vincamine is also commonly used as a nootropic agent to combat the effects of ageing, or in conjunction with other nootropics for a variety of purposes (Cook and James, 1981)." [Arora MPB]




Amino Acids



  • Lathyrus sativus [Rosenthal HerbV1]
  • Lathyrus sylvestris [Rosenthal HerbV1]
  • Lathyrus cicera [Rosenthal HerbV1]
  • Lathyrus latifolius [Rosenthal HerbV1]
  • Lathyrus clymenum [Rosenthal HerbV1]

Lathyrogens, amino acids found mainly in the seeds of sweetpea (Lathyrus odoratus) and its relatives (Lathyrus spp., Vicia spp.), are responsible for lathyrism, a chronic disease. [CPPlantMush] They are "any of a group of nucleophilic compounds (as B-aminopropionitrile) that tend to cause lathyrism and inhibit the formation of links between chains of collagen". [merriam-webster]

"The extensive literature existing on "lathyrogens" mostly refer to a group of synthetic compounds inducing skeletal deformities and changes in the mesenchymal tissues in experimental animals. Human lathyrism bears no resemblance to these defects and is actually characterized by spastic paralysis of the legs as a result of neurological lesions of the spinal cord degeneration." [Liener TCPF]

"While osteolathyrism as such is not a public health problem, neurolathyrism is, especially in central parts of India. A 1958 epidemiological survey (Dwivedi and Prasad, 1964) indicates that in a single District (Rewa, Madhya Pradesh) there are as many as 25,000 cases of neurolathyrism in a total population of 634,000. The L. sativus is a hardy crop and survives adverse agricultural conditions, thus forming a major portion of the diet especially under famine conditions. The Indian farmers continue to grow it despite their awareness of its poisonous nature." [Liener TCPF]

"Human lathyrism is an ancient disease, manifested as a result of the consumption of the seeds of certain Lathyrus species, mainly those of L. sativus (chickling vetch or chick pea), L. cicera (flat-podded vetch), and L. clymenum (Spanish vetchling). It is habitually eaten by large populations in India and Algeria and less commonly in France, Italy, Spain, and other countries. The disease has been reported from a number of countries in Europe, Africa, and Asia. It is prevalent among horses and cattle as well." [Liener TCPF]

"Lathyrogen toxin is one of the natural toxins found in the seeds of lathyrus, commonly known as khesari or teora, which is known to cause lathyrism." [Amit et al, 2009]

"If consumed in excess quantity for long time, it causes paralysis in the legs in susceptible individuals and is believed to be caused by a toxic amino acid known as N-Oxalyl amino alanine (BOAA). The BOAA content of seed of lathyrus varies from 0.05 to 0.4% (Srivastava et al., (2000). Less than 0.2% BOAA is considered safer from health point of view (Siddiqu, 1995)." [Amit et al, 2009]

"The concentration of BOAA is maximum in the germ portion of the seed of lathyrus; therefore the degerming of the seed cotyledons greatly reduces the neurotoxin content of lathyrus seed (Prakash et al., 1977). Processing techniques like soaking, parboiling, roasting and degerming eliminates neurotoxin to a large extent. Pre-cooking soaking of pulse removes 30-40% of toxin (Srivastava and Srivastava, 2002). Roasting of seeds for about 15-20 min at 140 0C removes most of the toxin of lathyrus (Rao et al., 1969). Preboiling of lathyrus seeds removes more than 80% of the toxin and produces minimum change in nutritive value (Nagrajan et al., 1965)." [Amit et al, 2009]

"Lathyrus sativus L. (Vetch) is a resilient subtropical/tropical legume crop which is also known as grass or Indian pea. Beans of this so-called ‘famine crop’ are a chief source of nutrition among poor people in Africa and Asia. Its seed contains the neurotoxin β-N-oxalyl-L-α-β-diamino-propionic acid (BOAA) which causes a disease known as lathyrism, a paralysis of lower limbs in both men and animals. It is widespread among adults in Central India who consume it in large quantities (above 33% in the diet) for 3–6 months. However, in extreme cases it may cause death. When consumed as a supplement to an otherwise adequate diet, it does not produce the toxic effects (Enneking, 2011)."


"Certain members of the Lathyrus and Vicia genera contain compounds called osteolathyrogens which are teratogenic, causing congenital skeletal defects in offspring. The malformations are characterized as contracture or flexure of the pastern and carpal joints, lateral rotation of the forelimbs, scoliosis, kyphosis, torticollis, and front limb abductions. The extent to which these two genera contribute to congenital malformations in livestock grazing on native ranges in the USA is unknown but believed to be minimal. The malformations have been reproduced by experimental feeding of the synthetic osteolathyrogen aminoacetonitrile for as few as 10 days anytime during gestation days 20-129 in sheep (Keeler and James 1971). The natural lathyrogen believed to be the teratogen is B-aminopropionitrile." [Riet-Correa PPMRT]

"Another malady distinct clinically from neurolathyrism is osteo- lathyrism; the latter involves bone and mesenchymal tissue aberrations (Selye, 1957). Animals eating Lathyrus odoratus seeds exhibit osteolathy- ritic effects. A disorder of the vascular system, termed angiolathyrism, accompanies osteolathyrism. Lathyrus species such as L. hirsutus and L. pusillus give rise to both neurolathyritic and osteolathyritic effects (Selye, 1957), but L. odoratus induces only osteolathyrism." [Rosenthal HerbV1]

Methods of Detection

"Since the lathyrogens occurring in nature happen to be amino acids or their derivatives, ninhydrin reagent can be used for their detection and estimation. ß-Aminopropionitrile gives a characteristic green color with ninhydrin, a reaction which Garbutt and Strong (1957) developed into a quantitative assay for the osteolathyrogen. In the case of the neurotoxic amino acids, ß-cyanoalanine also gives a green color with ninhydrin. The extremely good resolution of acidic and basic constituents achieved by high-voltage electrophoresis makes this a very useful method for scanning plant or seed extracts for the presence of unusual nitrogenous constituents." [Liener TCPF]


  • Amit et al, 2009 - Antinutritional Factors and their detoxification in pulses - A review, Amit Kumar Jain, Sudhir Kumar, J.D.S. Panwar, Department of Microbiology and Botany, Janta Vedic College, Barut (Baghat) U.P., Agric. Rev., 30, 2009
  • merriam-webster - "Lathyrogen." Merriam-Webster, n.d. Web. 3 Sept. 2016.


"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]


  • Wiki - Oligopeptide,, This page was last edited on 18 December 2019, at 02:04 (UTC)., Accessed March 4, 2020
    • [2], George E. Chlipala, Shunyan Mo, and Jimmy Orjala (2011). "Chemodiversity in Freshwater and Terrestrial Cyanobacteria – a Source for Drug Discovery". Curr Drug Targets. 12 (11): 1654–73. doi:10.2174/138945011798109455. PMC 3244969. PMID 21561419
    • [4], Argos, Patrick. "An Investigation of Oligopeptides Linking Domains in Protein Tertiary Structures and Possible Candidates for General Gene Fusion" (PDF). European Molecular Biology Laboratory. Archived from the original (PDF) on 28 July 2014. Retrieved 28 July 2014.


Four plant enzyme groups exist: [FEMI]

  • Proteases - break long protein chains into smaller amino acid chains and eventually into single amino acids [FEMI]
  • Amylases - reduce polysaccharides to disaccharides: lactose, maltose, and sucrose [FEMI]
  • Lipases - break triglycerides into individual fatty acids and glycerol [FEMI]
  • Cellulases - digest specific carbohydrate bonds found in fiber [FEMI]


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)


  • (Wiki) Essential Fatty Acid,, Accessed Sept 3, 2016
    • [1]Robert S. Goodhart; Maurice E. Shils (1980). Modern Nutrition in Health and Disease (6th ed.). Philadelphia: Lea and Febinger. pp. 134–138. ISBN 0-8121-0645-8.
    • [2]Whitney Ellie; Rolfes SR (2008). Understanding Nutrition (11th ed.). California: Thomson Wadsworth. p. 154.
    • [22]Honoré E, Barhanin J, Attali B, Lesage F, Lazdunski M (March 1994). "External blockade of the major cardiac delayed-rectifier K+ channel (Kv1.5) by polyunsaturated fatty acids". Proceedings of the National Academy of Sciences of the United States of America. 91 (5): 1937–41. doi:10.1073/pnas.91.5.1937. PMC 43279free to read. PMID 8127910.
    • [23]Reiffel JA, McDonald A (August 2006). "Antiarrhythmic effects of omega-3 fatty acids". The American Journal of Cardiology. 98 (4A): 50i–60i. doi:10.1016/j.amjcard.2005.12.027. PMID 16919517.
    • [24]Landmark K, Alm CS (November 2006). "[Alpha-linolenic acid, cardiovascular disease and sudden death]". Tidsskrift for Den Norske Lægeforening (in Norwegian). 126 (21): 2792–4. PMID 17086218.
    • [25]Herbaut C (September 2006). "[Omega-3 and health]". Revue médicale de Bruxelles (in French). 27 (4): S355–60. PMID 17091903.
    • [26]James, William; Berger, Timothy; Elston, Dirk (2005). Andrews' Diseases of the Skin: Clinical Dermatology. (10th ed.). Saunders. ISBN 0-7216-2921-0.

Linoleic acid

(Essential Fatty Acid)


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)




"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]


"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)

Depending on their chemical nature and structure, glycosides are divided into;

  • Cyanogenic glycosides (aglycones contain prussic acid),
  • cardiac glycosides (aglycones are cardinolides and bufadienolides),
  • Saponins (aglycones are triterpene and steroid compounds) - Saponins are glycosides that make suds when shaken in water. The name comes from the Latin word “Sapo” meaning soap.... Saponins cause hemolysis after intravenous introduction. Because of this, they are only introduced orally." [Eisenman MPCA]
  • anthraglycosides (aglycones are derivatives of anthracene),
  • phenolics (aglycones are coumarins, flavonoids, and others) [Eisenman MPCA]
  • Phenylpropanoid glycosides [Pengelly TCMP]
  • glycoalkaloids (aglycones are nitrogen-containing steroid compounds). [Eisenman MPCA]

Cardiac Glycosides

"This category includes those glycosides which have a direct action on the heart. Many of these glycosides can, and are used in medicine in carefully-controlled form and amount to tone the heart and to improve cardiac function ... thus slowing a rapid, thready heartbeat. Toxic doses, however, can kill by causing cardiac arrest."
"Over 400 different cardenolides have been identified in the plant kingdom. Plants commonly encountered by foragers which contain cardenolides include crown vetch (Coronilla spp.), dogbane, and milkweed. Domesticated plants include foxglove, oleander, and lily-of- the-valley."[WildFoodsForum]
"Symptoms of poisoning include nausea/severe digestive upset, vomiting, diarrhea, and blurred and disturbed color vision. Interestingly, though, the body seems to have a built-in defense mechanism against cardenolides in the form of spontaneous vomiting. However, this has not worked with 100% efficiency in all cases, and hence a number of deaths have occurred from cardenolide poisoning." [WildFoodsForum]
"Cardiac glycosides, also known as cardioactive and cardiotonic glycosides, are a group characterized for their direct action on the heart. Over 400 have been isolated, the best known being the digitalis glycosides present in purple foxglove (Digitalis purpurea). Besides their effect on the heart muscle, cardiac glycosides can produce severe digestive upset with nausea vomiting, abdominal pain, diarrhea, blurred and disturbed color vision, and other symptoms relating to decreased heart function."[CPPlantMush]


  1. [WildFoodsForum]Vol. 9, No.1, January - February 1998

Other Glycosides


Distribution: Naturally occurring glycoside of hydroquinone, q.v., found in the bark and leaves of various plants, usually occurring together with methylarbutin. Principal antibacterial constituent of the traditional medicine, uva ursi, q.v. Isoln from bearberry leaves (Arctostaphylos uva-ursi Spreng., Ericaceae): from leaves of blueberry (Vaccinium), cranberry (Oxycoccus), and pear (Pyrus communis L., Rosaceae):

Properties: Occurs as the monohydrate. Colorless elongated prisms from moist ethyl acetate, mp 199o after sintering at 163-164o (Robertson, Waters). Also reported as unstable form, mp 165o; stable form, mp 199.5-200o (Lindpaintner). [a]D20 -60.3o (in water). Sol in water and in alc.
Melting point: mp 199o after sintering at 163-164o (Robertson, Waters); unstable form, mp 165o; stable form, mp 199.5-200o (Lindpaintner)

Derivative Type: Methylarbutin C13H18O7
Properties: Crystallizes from water as the monohydrate, mp 158-160o; solidifies and melts again at 175o (Mannich). Also reported as unstable form, mp 160.5o; stable form, mp 176o (Lindpaintner). [a]D20 -60.66o (in water). Sol in hot water or alcohol; slightly sol in ether.
Melting point: mp 158-160o; solidifies and melts again at 175o (Mannich); unstable form, mp 160.5o; stable form, mp 176o (Lindpaintner)

Use: In cosmetics as a skin lightening Agent



(Cardiac Glycosides)




Conversion into Primary Carcinogen: Hydrolysis of ptaquilosides leads to pterosins; under milder conditions a dienone which is believed to be the primary carcinogen is obtained. Under weakly alkaline conditions both ptaquiloside and its aglycone ptaquilosin are converted, with D-(+) glucose liberation in the former case, into the unstable dienone, which is the activated form regarded as the ultimate carcinogen (Kigoshi et al, 1993). [Potter CEP]




Distribution: Salicin is found in Salix (willow) (Mills HMPL)

Properties: "Salicin is an alcohol glycoside found in willow bark that yields salicyl alcohol when hydrolyzed. Salicin has anti-inflammatory properties probably due to its oxidation into salicylic acid." (Mills HMPL)

Unsorted Compounds

Hydrocyanic acid

Properties: "Since prussic acid (HCN) inhibits cytochrome oxidase, which is the final step of the respiratory chain, it is a very potent poison (section 5.5). Ten percent of all plants are estimated to use this poison as a defense against being eaten by animals. The consumption of peach kernels, for instance, or bitter almonds can have fatal results for humans. As also plants possess a mitochondrial respiratory chain and, in order not to poison themselves, they contain prussic acid in the bound form as cyanogenic glycoside.... The cyanogenic glycosides are stored as stable compounds in the vacuole. The glycosidase catalyzing the hydrolysis of the glycoside is present in another compartment. If the cell is wounded by feeding animals, the compartmentation is disrupted and the glycosidase comes into contact with the cyanogenic glycoside. After the hydrolysis of the glucose residue, the remaining cyanhydrin is very unstable and decomposes spontaneously to prussic acid and an aldehyde. A hydroxynitrile lyase enzyme accelerates this reaction. The aldehydes formed from cyanogenic glycosides are often very toxic. For a feeding animal, the detoxification of these aldehydes can be even more difficult than that of prussic acid. The formation of two different toxic substances makes the cyanogenic glycosides a very effective defense system." [Heldt PB]

"Our bodies are able to neutralise cyanides by converting them to thiocyanates, which are eliminated in the urine (Bruneton 1995), however, this capacity can be overloaded if doses of cyanide are sufficiently high." [Pengelly TCMP]

"A lethal dose of cyanide is between 0.5 and 3.5 mg/kg body weight. Cyanide binds to ferric ions of mitochondrial cytochrome oxidase and halts cellular respiration. The symptoms of acute cyanide intoxication are mental confusion, muscular paralysis, and respiratory failure." [Omaye FNT]

"There is hope that cyanogenesis may provide a means of destroying cancer cells. By targeting cancer cells with linamarase via a retrovirus and then supplying linamarin, it has been possible to selectively generate toxic HCN in cancer cells." [MNP Dewick]

Ibotenic acid



"All the species confirmed to be involved in ibotenic acid toxicity are closely related amanitas-Amanita pantherina, A. muscaria in its many forms, A. gemmata, A. aprica (probably), and others that are not known to occur in the western U.S. Toxin levels are highly variable for reasons that are unclear. In general, A. pantherina contains higher concentrations than A. muscaria (such that pantherine is another name applied to this type of poisoning). One study of a color-series of dark brown through paler brown A. pantherina to brownish yellow and finally yellow A. gemmata, showed that toxin levels were positively correlated with darkness of color. In another study, specimens of amanitas collected in summer had ten times the toxin levels as specimens collected in fall." [Trudell MPNW]






Amanita muscaria (fly agaric)[IKAN STCNP]


Usnic Acid

"Usnic acid was identified in many genera of lichens including Usnea, Cladonia, Hypotrachyna, Lecanora, Ramalina, Evernia, Parmelia and Alectoria. Although it is generally believed that usnic acid is exclusively restricted to lichens, in a few unconfirmed isolated cases the compound was found in kombucha tea and non-lichenized ascomycetes.[4][5]" [Wiki]

"Usnic acid is a secondary metabolite in lichens whose role has not been completely elucidated. It is believed that usnic acid protects the lichen from adverse effects of sunlight exposure and deters grazing animals with its bitter taste" [Wiki]


Vulpinic Acid

Class of Compound: Pulvinic acid derivative [Rankovic LSM]


Basic Properties

"Pulvinic acid found in several lichen species, as well as some non-lichenized fungi.[2]" [Wiki]

"Based on the chemical structures, most lichen substances are phenolic compounds (orcinol and β-orcinol derivatives), dibenzofu- rans (e.g. usnic acid), depsides (e.g. barbatic acid), depsidones (e.g. salazinic acid), depsones (e.g. picrolichenic acid), lactones (e.g. protolich- esterinic acid, nephrosterinic acid), quinones (e.g. parietin) and pulvinic acid derivatives (e.g. vulpinic acid) (Shukla et al. 2010)." [Shukla LBE]

"Only two terphenylquinones, polyporic acid and thelephoric acid, are known, while pulvinic acid derivates are more numerous (calycin, epanorin, leprapinic acid, leprapinic acid methyl ether, pinastric acid, pulvinic acid, pulvinic dilactone, rhizocarpic acid, stictaurin, vulpinic acid)." [Rankovic LSM]


"This multitude of compounds made the study of their chemistry attractive from the early times of organic chemistry. Bebert (1831) isolated vulpinic acid in 1831.... The lichen substances first known in their structure were vulpinic acid (Spiegel 1883) and lecanoric acid (Hesse 1900), which was synthesized by E. and H. Fischer in 1913. The structure of most lichen substances remained unknown till the beginning of the outstanding work of the famous Japanese chemists Y. Asahina (born 1880 in Tokyo, died 1975 in Tokyo; Fig. 2) and S. Shibata (born 1915 in Tokyo; Fig. 3) in 1921." [Siegfried ILS]


"Vulpinic acid is relatively toxic." [Wiki]

"The vulpinic acid occurring in Letharia vulpina, used as a fox poison, has been repeatedly studied toxicologically. Kobert (1892) and Neuberg (1893) gave the lethal dose for mammals as 20-30 mg per kilogram of body weight; the same figure applies to the closely related pinastric acid. The toxicity of vulpinic acid was later found to be lower; Santesson (1939) obtained 78.8 mg per kilogram of body weight as the lethal dose for a cat, the most noticeable symptom of poisoning being acute dyspnea. Brodersen and Kjaer(1946) reported the lethal dose for a mouse as 75.0 mg per kilogram of body weight." [Ahmadjian Lichens]

"In northern Europe the lichen Letharia vulpina was used traditionally as a poison for foxes and wolves. The toxic principle is the pulvinic acid derivative vulpinic acid, which is not only poisonous to all meat eaters but also to insects and mollusks. Surprisingly this compound is ineffective against rabbits and mice. The secalonic acid derivatives are also highly poisonous. These substances are mycotoxins and, like vulpinic acid, may have evolved to serve a twofold ecological role. Thus, in addition to screening incoming light, they are highly poisonous to grazing herbivores." [LichBio2]

Other Uses

Dye: "In North America, the most significant lichen dye is Letharia vulpina, from which indigenous people extract yellow dye based on vulpinic acid." [Upreti RAL]

Repellant: "The slug-repelling activity of vulpinic acid is being investigated as a seed treatment for protecting higher plants. Likewise, the insect Spodoptera littoralis was strongly deterred by usnic acid and vulpinic acid (Dayan and Romagni 2001)." [Rankovic LSM]


"Vulpinic acids and evernic acids of certain lichen compounds are antagonistic to Graphis scripta and Caloplaca citrine." [Peter BUHC]

"Secondary metabolites of different species of lichen were tested for their activities against a variety of microbial species. While Gram-negative rods and fungi were not inhibited by these compounds, Staphylococcus aureus, Enterococcus faecalis, Enterococcus faecium, and some anaerobic species (Bacteroides and Clostridium species) were susceptible at the concentrations tested. Vulpinic acid was generally less active than usnic acid, regardless of its stereochemistry. The susceptibility to usnic acid was not impaired in clinical isolates of S. aureus resistant to methicillin and/or mupirocin (Lauterwein et al. 1995)." [Rai MPBD]

"Whiton and Lawrey (1982) reported that ascospore germination of Sordaria fimicola was significantly inhibited by evernic and vulpinic acids. Usnic acid, evernic acid, and vulpinic acid inhibited the growth of the Gram-positive bacteria Staphylococcus aureus, Bacillus subtilis, and Bacillus megaterium, but had no effect on the Gram-negative bacteria Escherichia coli or Pseudomonas aeruginosa (Lawrey 1986)." [Rankovic LSM]

"...anti-Gram-positive activities have been reported for evernic acid, vulpinic acid, and hirtusneanoside (Renzaka and Sigler 2007)." [Rankovic LSM]

"Antibiotic activity has been shown especially for usnic, evernic and vulpinic acids, as well as for derivates of diploicin with antitubercolous activity (Muggia et al. 2009)." [Upreti RAL]

Other Properties

"Light screen compounds of certain lichen protect the light sensitive photobiont against high intensity of ultra violet exposture. ... The compounds that regulate solar radiation are parietin, usnic acid, and vulpinic acid." [Peter BUHC]

"Pulvinic acid and its derivatives, such as calycin, epanorin, pulvinic acid lactone as well as leprapinic, pinastric, rhizocarpic and vulpinic acids, form a group of mostly yellow pigments (Huneck and Yoshimura 1996)." [Shukla LBE]

"Desiccating lichens shrink without wilting and change their consistency and often their colour; the latter applies for those species which derive their colouration from the photoautotrophic partner, not from secondary fungal metabolites in the peripheral cortical layer.... Hardly any colour changes during desiccation are seen in innumerable grey to dark brown or black Parmeliaceae, Physciaceae, Umbilicariaceae, or in intensely yellow representatives of Teloschistaceae (Xanthoria, many Caloplaca and Teloschistes species) with golden-yellow anthraquinones in their peripheral cortex, or in the sulfur-yellow Letharia vulpina (wolf lichen) and related species with vulpinic acid at their thallus periphery." [Esser PR]


"Kanokmedhakul et al [2003], isolated from the mushroom Scleroderma citrinum the compound 4,4'-dimethoxyvulpinic acid and two of its derivatives, the dibromo derivative 5 and acetate derivative 6; all of them exhibited inhibitory activity towards M. tuberculosis." [Varela MP]


Journals of Interest

Terpene & Terpenoids


"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."



"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 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]

Adverse Health Effects

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]


"Cucurbitacin C is found only in C. sativus (Enslin and Rehm 1958)." [EMNMPV.2]



"Carotenoids, which occur in all plants, bacteria, and fungi, are probably the most widely distributed of all natural pigments; they are involved in many fundamental processes such as photosynthesis and mammalian vision. These highly unsaturated lipids also serve as vegetative, floral, and fruit pigments in plants and as pigments in the feathers of birds, outer parts of insects, as well as the skins of fish and other animals (Britton, 1976, 1983; Buchecker, 1982; Kayser, 1982)." [Seiger PSM]

"The properties and stroctures of tetraterpenes differ markedly from those of the lower terpenes (Ramage, 1972). Carotenoids (the major representatives of this class) are mostly linear polyene systems. The high degree of unsaturation renders them both heat and light sensitive. These compounds are an experimentally demanding group of compounds with which to work (Britton, 1983; Ramage, 1972) .. Methods for purification of carotenoids are similar to those for other terpenoids, but, because of the highly unsaturated nature of the compounds, special care must be taken (Britton, 1991). Care to avoid oxidation is most important; extracts that contain chlorophyll must be handled with special care." [Seiger PSM]

"Most carotenoids are colored and absorb light in the visible range of the spectrum. The specific wavelength of absorption is a function of the structure, in particular, the number and arrangement of double bonds and oxygenated substituents, but also the solvent and other factors (Britton, 1983). Most carotenoids are yellow to orange (sometimes red) when isolated." [Seiger PSM]

"As mentioned above, the leaves of all green plants contain the same major carotenoids: B-carotene (1), lutein (2), violaxanthin (3), and neoxanthin (4). Smaller amounts of other compounds are often present." [Seiger PSM]

"Animals require vitamin A (retinol) (19) or a carotenoid precursor for normal growth and vision (Liu, 1982). An early symptom of vitamin deficiency is a decreased ability to see in dim light." [Seiger PSM]

"Many of the colors used for aposematic labeling by animals (bright reds, oranges, and yellows) are produced by carotenoid pigments (Rothschild, 1975, 1978). These compounds ultimately arise from plants (or from symbiotic bacteria?), as animals cannot synthesize carotenoids." [Seiger PSM]

"Carotenoids, especially J3-carotene (I), often have heen used for coloring food products. This is especially common in such fatry foods as margarine. Bixa orellana, achiote or annatto, has been used as a food colorant and flavoring in Latin America for generations, a practice now common in most tropical areas of the world. The seeds of this plant contain bixin (31), the methyl ester of 6,6'·diapocarotenoic acid. In the Iberian peninsula, the use of Crocus sativus (saffron, Iridaceae) as a food coloring material is widespread. Some of the yellow pigments of this plant, such as crocein (29), also are carotenoids (Rothschild, 1975). Many carotenoids (e.g., J3-carotene) are antioxidants. This property has led to the suggestion that they are important in the diet and can afford protection against some forms of cancer and other diseases (Britton, 1991)." [Seiger PSM]


"Another group of important carotenoid-derived compounds are the strigolactones, a group of tricyclic lactones conjugated with a C5-butyrolactone (Butler, 1995; Hum- phrey and Beale, 2006)."[Roy PP]

"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]


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