Alkaloids

Classification
  • Amino alkaloids
  • Aporphine alkaloids
  • Diazocin alkaloids
  • Diterpene alkaloids
  • Imidazole alkaloids
  • Indole alkaloids
  • Isoquinoline alkaloids
  • Piperidine alkaloids
  • Purine alkaloids
  • Pyrrolidine alkaloids
  • Pyrrolizidine alkaloids
  • Quinoline alkaloids
  • Quinolizidine alkaloids
  • Steroidal alkaloids
  • Tropane alkaloids

Amino alkaloids
Compound Local Source Compound Local Source
- - - -
Aporphine alkaloids
Compound Local Source Compound Local Source
- - - -
Diazocin alkaloids
Compound Local Source Compound Local Source
- - - -
Diterpene alkaloids
Compound Local Source Compound Local Source
- - - -
Imidazole alkaloids
Compound Local Source Compound Local Source
- - - -
Indole alkaloids
Compound Local Source Compound Local Source
Vincamine - - -
Isoquinoline alkaloids
Compound Local Source Compound Local Source
Berberine Mahonia Sp. - -
Piperidine alkaloids
Compound Local Source Compound Local Source
- - - -
Purine alkaloids
Compound Local Source Compound Local Source
- - - -
Pyrrolidine alkaloids
Compound Local Source Compound Local Source
- - - -
Pyrrolizidine alkaloids
Compound Local Source Compound Local Source
- - - -
Quinoline alkaloids
Compound Local Source Compound Local Source
- - - -
- - - -
Quinolizidine alkaloids
Compound Local Source Compound Local Source
Anagyrine
camoensin
Cytisine
Lupanine 		Lupinus Sp.
Laburnum Sp.; Cytisus Sp.
Lupinus Sp. 		Lupinine
Matrine
Sparteine 		-
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]

Biochemistry

"Two similar though separate enzymes of these glucosyltransferases were found to be present in almost all organs of S. melongena, eggplant/aubergine. One enzyme catalyzed the transfer of activated glucose to diosgenin, the other one to its N-containing congener solasodine (Paczkowski et al. 1998). Recently, a first glucosyltransferase involved in steroidal saponin biosynthesis, obtained from S. aculeatissimum, could be cloned. This enzyme, SaGT4A, did not show a strict substrate specificity; it catalyzed the 3-O-glucosylation of diosgenin, nuatigenin, and tigogenin as well as of steroidal alkaloids like solanidine, solasodine, and tomatidine. Anyhow, it turned out to be involved in plant defence system, since it was accumulated intensively as a wounding response (Kohara et al. 2005)." [Eckart_Eich]

Potatoes

"Outbreaks of poisoning from potatoes have been associated with higher than normal concentrations of glycoalkaoids(a-solanine and a-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]

Glycoalkaloids found in Potato include;
  • a-Solanine [Nigg PRMA]
  • ß-Solanine [Nigg PRMA]
  • y-Solanine [Nigg PRMA]
  • a-Chaconine [Nigg PRMA]
  • ß-Chaconine [Nigg PRMA]
  • y-Chaconine [Nigg PRMA]
  • Solanidine [Nigg PRMA]
  • Demissine [Nigg PRMA]
  • Commersonine [Nigg PRMA]
  • Demissidine [Nigg PRMA]
  • 5ß-Solanidan-3a-ol [Nigg PRMA]
  • Leptidine [Nigg PRMA]
  • Leptine I [Nigg PRMA]
  • Leptine II [Nigg PRMA]
  • O(23)-Acetylleptinidine [Nigg PRMA]
  • Leptinine I [Nigg PRMA]
  • Leptinine II [Nigg PRMA]
  • Leptinidine [Nigg PRMA]
  • a-Solamarine [Nigg PRMA]
  • ß-Solamarine [Nigg PRMA]
  • Tomatidenol [Nigg PRMA]

"Under certain weather conditions, potato tubers may synthesize considerable amounts of a-solanine. Exposure to light in the field or in the marketplace can increase the a-solanine content to dangerous levels (Griebel, 1924). The glycoalkaloid content can also increase during potato growth as weIl as after harvest (Sinden and Webb, 1972). The amounts of a-solanine and a-chaconine increase with light- or wound-induction (Wu and Salunkhe, 1978). Several outbreaks of illness have been traced to the use of potatoes with a-solanine contents ranging from 100 to 400 ug/g (Alfa and Heyl, 1923). Acute illnesses induced by glycoalkaloid poisoning probably are more prevalent than is indicated by the few recorded medical cases (Wood and Young, 1974)." [Nigg PRMA]

"a-Solanine and a-chaconine contents of potatoes are not affected by baking, boiling, or microwaving and are only slightly reduced by frying (Bushway and Ponnampalam, 1981). During cooking, glycoalkaloids move into the cortex region; whereas, phenols migrate from the peel into both the cortex and internal tissues. When potatoes were peeled before cooking, their phenolic contents were decreased, but the TGA [total glycoalkaloid] contents in the internal tissues were unchanged (Mondy and Gosselin, 1988). Symptoms of TGA poisoning can be easily mistaken for gastroenteritis." [Nigg PRMA]

"The TGA content of potato tissues is given in Table 17 (Wood and Young, 1974). Bruising can dramatically increase the TGA content at various temperatures (Jadhav et al., 1981), significantly enhance the phenolics, and decrease ascorbic acid levels. In fresh Katahdin potatoes, the greatest increase of phenols from about 210 ug/g to 1,720 uu/g occurred at 5"C, and an increase in TGA content from about 50 ug/g to 220 ug/g occurred at 20oC (Mondy et al., 1987). At 10 days after wounding, Juliver variety tubers held in the dark had a-chaconine and a-solanine concentrations of 685.4 ug/g and 499.6 ug/g, respectively; unwounded control tubers contained 371.7 ug/g and 271.6 ug/g, respectively. Final concentrations of glycoalkaloids in wounded potatoes were usually higher in the light. Potato chips produced from unwounded tubers had a-chaconine and a-solanine concentrations of 107.1 ug/g and 69.2 ug/g, respectively, and those from wounded tubers had 245.7 ug/g and 197.6 ug/g, respectively (Ahmed and Müller, 1978). Potatoes that contain more than 200 ug/g TGA per tuber are considered unfit for consumption (Smith, 1977; Wood and Young, 1974)." [Nigg PRMA]

Hazards

"The toxicity of steroidal alkaloid glycosides is of some concern, in that several plant species that can accumulate them are major food crops." [MNP Dewick]

"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). Steroidal alkaloids bearing a basic nitrogen atom in ring F, shared or unshared with ring E, with bonding capabilities in (X-position to the steroid plane may be teratogenic (Gaffield and Keeler 1984)." [Bajaj MAPS 4]

"Beside the pharmacological effects listed, 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). The membrane-disrupting properties of solasonine and solamargine were studied thoroughly in artificially prepared phosphatidylcholine/cholesterol liposomes (Roddick et al. 1990)." [Bajaj MAPS 4]

"In animals, adverse physiological effects of glycoalkaloids are mani fested in a number of ways (reduced respiratory activity or blood pressure, bradykardia, haemolysis, etc.) which are thought to stem mainly from membrane disruption, inhibition of acetyicholinesterase or interference with sterol/steroid metabolism, or from combinations of these. As a-solanine and a-tomatine are serum cholinesterase inhibitors (Jadhav etal 1981) and a-solanine and a-chaconine have been shown to significantly inhibit bovine and human acetylcholin esterase at a concentration of 100 uM (Roddick, 1989), at least part of their toxic effects are probably thus accounted for. Solamargine has little anticholinesterase activity but binds readily to cholesterol in vitro and has significant membrane-disrupting properties (Roddick etal 1990)." [Hostettmann Saponins]

"Occasionally, even relatively small doses of solanaceous alkaloids that are well below the threshold of taste can be dangerous. For example it was recently reported that some glycoalkaloids from supposedly safe, freshly purchased potatoes (i.e. non-green) might be implicated in inflammatory bowel disease. Given our current preoccupation with food safety, it is quite likely that, were potatoes or tomatoes to be introduced as new foods today, they would be banned by most national regulatory agencies due to the risk of accidental alkaloid poisoning. This is not just a theoretical risk. During the 1980s, a potato variety called Lenape was withdrawn from sale because of its potential toxicity due to high levels of alkaloids such as solanine.597" [Murphy PPG]

"Supplementation with ascorbic acid has been shown to protect against toxicity from these alkaloids (Renwick 1986)." [Pengelly TCMP]

Activities

"a-Solanine (Fig. 22) is a weak to moderate inhibitor of both specific and non-specific cholinesterases (Patil et al., 1972), and a-chaconine (Fig. 22) is a potent inhibitor of the cholinesterase isoenzymes (Alozie et al., 1979). When extracts of potato were used to inhibit human plasma cholinesterase, extracts from peel were 10 to 40 times more active than those from the innermost flesh, showing the accumulation of alkaloids in the peel (Orgell et al., 1958a,b). The potato glycoalkaloids, leptine I (Fig. 23) and demissidine (Table 16), were among the most inhibitory natural products to human plasma cholinesterase (Orgell, 1963). Cholinesterase inhibition was used to categorize 24 potato varieties (Orgell and Hibbs, 1963). No carcinogenicity data exist for the cholinesterase inhibitors found in potato (Ames et al., 1987)." [Nigg PRMA]

"Steroidal alkaloids. such as solanine and tomatine which are present in many mem- bers of the Solanaceae, can form complexes with the cholesterol present in biomembranes. Important for this interaction is the presence of a lipophilic portion of the molecule (given by the steroidal moiety) and a hydrophilic portion (provided by the sugar side chain). Whereas the lipophilic moiety "dives" into the lipophilic interior of the membrane and interacts with the structurally similar cholesterol, the hydrophilic side chain remains outside and binds to external sugar receptors. As phospholipids are in continuous motion, a tension easily builds up which leads to membrane disruption, i.e., transient "holes" occur in the biomembrane rendering the cell leaky. A similar mechanism has been postulated for saponins, a widely distributed group of natural products, to which the steroidal alkaloids may be assigned (Fig. 1). Steroidal alkaloids can also interact with other targets, such as receptors." [Roberts Alk]

Treatment of Skin Disorders

"Attention should be paid to the fact that the external application of herbal medicines containing steroidal alkaloids against skin disorders is common throughout all cultures. A patent application by Spencer et al. (1982) shows that this application proves true in modem medical therapy. Steroidal alkaloids are considered to be the active compounds in the drug." [Bajaj MAPS 4]

Fungitoxicity

"With all fungi tested, a-chaconine was more fungitoxic than a-solanine (Allen and Kuc, 1968; McKee, 1959). An interesting aspect of the fungitoxicity of the steroid glycoalkaloids is that the protonated forms (approximately pH 5.5 or lower) are less active than the free bases (Allen and Kuc, 1968; McKee, 1959). The difference is greater than 100-fold between pH 5.5 and 7.4." [Nigg PRMA]

"Conner (1937) found that solanine in Solanum tuberosum is toxic to conidiospores of the fungus Cladosporiumfulvum Link., although Manske (1950) was unable to attribute the high resistance of Solanum racemigerum L. (nightshade) to attack by Phytophthora species to its relatively high solanine content." [Roberts Alk]
Compound Local Source Compound Local Source
Solanidine
Solanine
Imperialin 		- Jervine
Veratridine 		-
Tropane alkaloids
Compound Local Source Compound Local Source
- - - -

Berberine

Distribution

Activities

Properties:

References

Cytisine

(Quinolizidine Alkaloid)

Distribution

Hazards

Pharmacology

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]

Properties

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]

Insecticide

"...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]

Imperialin

(Steroidal Alkaloid) [Hostettmann HCBPAM]

Jervine

(Steroidal Alkaloid) [Hostettmann HCBPAM]

Muscarine

(Alkaloid)

"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]

Distribution

References

Solanidine & Solanine

(Steroidal Alkaloid)

"α-Solanine (17), α-tomatine (18), dehydrotoma- tine (19), and verazine (20) (Figure 7) are some selected examples of steroidal alkaloids having an unmodified C27 steroidal skeleton." [Hostettmann HCBPAM]

a-Solanine; Mp: 285–286oC (EtOH) "Acetylcholinesterase inhibitor [5, 6]; antifeedant, fungicide, and pesticide activities [7]" [Azimova Alkaloids]

y-Solanine; Mp: 237–239oC [Azimova Alkaloids]

Distribution of Solanine

Distribution of Solanidine

Biochemistry

"Solanidine is found in potatoes (Solanum tuberosum) typically as the glycosides α-solanine and α-chaconine (Figure 6.133). This condensed ring system appears to be produced by a branch from the main pathway to the solasodine/tomatidine structures. Thus, a substitution process will allow generation of the new ring system (Figure 6.135).
Enzymic data relating to the formation of the steroidal alkaloid aglycones are not available, but both enzymic and genetic studies have clarified sequences for elaboration of various glycoside side-chains. Thus, in potato, solanidine is converted into α-solanine by way of γ- and β-solanine. Alternatively, a different sequence of glycosylation reactions leads to α-chaconine (Figure 6.136). Toxicity appears to increase as the glycoside chain is extended." [MNP Dewick]

"Since the production of medicinal steroids from steroidal saponins (see page 281) requires preliminary degradation to remove the ring systems containing the original cholesterol side-chain, it is immaterial whether these rings contain oxygen or nitrogen. Thus, plants rich in solasodine or tomatidine could also be employed for commercial steroid production. Similarly, other Solanum alkaloids, such as solanidine, with nitrogen in a condensed ring system might also be exploited [Box 6.24]." [MNP Dewick]

"Crude solanine, extracted from the potato plant, is purified by dissolving in boiling methanol, filtering, and concentrating until the alkaloid crystallizes out (23)." [Sarker NP]

"Alkaloids of the solanidine group have been found in plants of the genera Solanum, Fritillaria, Rhinopetalum, Veratrum, and Korolkowia; and of the solasodine group, mainly in plants of the genus Sola- num. Alkaloids of the solanidine, solasodine, and verazine groups are based on the solanidanine, tomatanine, and 22,26-epiiminocholestane heterocy- clic skeletons, respectively." [Azimova Alkaloids]

Hazards

"A few situations have resulted in illness or death due to solanine. Symptoms include increasing gastric pain followed by nausea and vomiting, respiratory difficulties, weakness, and prostration. In experiments using human volunteers, 0.3 mg/100 g of solanine caused drowsiness, itchiness and hyperesthesia, and labored breathing. Higher doses result in symptoms of organophosphate poisoning." [Omaye FNT]

"However, it was shown that poisoning by Solanaceae is relatively rare, possibly due to a combination of unpalatability of the unripe fruits and the fact that solanine (29) is rapidly hydrolyzed to the less toxic aglycone in the gastrointestinal tract. Besides, 29 is also poorly absorbed from the gastrointestinal tract [24,28]." [Kuete TSAMP]

"The toxicity of this alkaloid is much greater when injected than when given orally. Ingested solanine is poorly absorbed and in the digestive tract most of it is metabolized to a less-toxic component, solanidine, and rapidly excreted." [Majak SPPWC]

[Solanine] poisoning is primarily displayed by gastrointestinal and neurological disorders. Symptoms include nausea, diarrhea, vomiting, stomach cramps, burning of the throat, cardiac dysrhythmia, nightmare, headache, and dizziness [79] as well as hallucinations, loss of sensation, paralysis, fever, jaundice, dilated pupils, hypothermia, and death in more severe cases. It was suggested that doses of 2-5 mg/kg of body weight can cause toxic symptoms, and doses of 3-6 mg/kg of body weight can be fatal [79]. It was reported that Solanum glycoalkaloids can inhibit cholinesterase, disrupt cell membranes, and can be teratogenic [80]." [Kuete TSAMP]

Activities

"Can cause haemolysis in other species (cattle and pigs) if large leaves or stems are fed or small quantities over a long period". [Brown TRM]

"Glycoalkaloids are long known to be inhibitors of acetylcholin-esterase (Roddick 1989). In this investigation, (X-chaconine and (X-solanine were the strongest inhibitors, tomatine was already less active, and solasonine and- solamargine only showed a weak inhibitory activity. The aglycones were basically inactive. " [Bajaj MAPS 4]

"Tomatine (240) and solanine (241), the steroidal alkaloid glycosides from Solanum tuberosum and Lycopersicon esculentum and their aglycones tomatidine and solanidine exhibit antifeedant properties (Dahlman and Hibbs 1967). These compounds are attracting renewed interest because of their arthropod resistance and interesting insecticidal and nematicidal action." [Koul PB]

"Anti-inflammatory activity: solanine A (steroidal alkaloid) obtained from methanolic extract of fruit of S. nigrum showed potent anti-inflammatory activity in LPS/IFNγ-activated macrophage and inhibition of NF-KB, ERK 1/ ERK 2, AKT and STAT1 signalling pathways in inflammation induced mice (Zhao et al. 2018a)." [Kunwar EH]

Cholinesterase Inhibitor (antienzyme): "Those common foods which are known to contain substances which inhibit the in vitro activity of cholinesterase are listed in Table I. It will be noted from this table that these inhibitors are found in various parts of the plant. The fact that different solvents are required for the extraction of the active substance from various plants would indicate that the active principles are not chemically identical. Little is actually known about the chemistry of these natural inhibitors of cholinesterase. In fact the only cholinesterase inhibitor which has been identified is the glycoside, solanine...." [Liener TCPF]

"The fruit of a number of solanaceous plants, including tomato (Lycopersicon esculentum), potato (Solanum tuberosum) and eggplant (Solanum melongena esculentum), have cholinesterase-inhibiting effects (Krasowski et al. 1997). They contain solanaceous glycoalkaloids α-solanine and α-chaconine, which are triglycosides of solanidine, a steroidal alkaloid derived from cholesterol. They are the only plant chemicals known to inhibit both acetlycholinesterase and butyrylcholinesterase, both in vitro and in vivo." [Marcello TPHM]

"The toxicity of glycoalkaloids is mainly due to their lytic effects on biological membranes. The disruption of the membrane appears to result from the ability of the steroidal alkaloids to complex with free sterols of the membranes (Roddick et al. 1992). With regard to the solasodine-based glycoalkaloids, solamargine is the more disruptive compound compared to solasonine, but together the two compounds showed a marked synergistic effect (Roddick et al. 1990). In addition, steroidal glycoalkaloids can inhibit the acetylcholinesterase, a key postsynaptic enzyme in the transmission of the nerve impulse (Roddick 1989). However, solasonine and solamargine were much less inhibitory than a-solanine and a-chaconine (Roddick 1989)." [Nagata MAPS 12]

solanine - anti-asthmatic effects [MPUC Trivedi]

"The Solanum alkaloid solanine inhibits RNA reverse transcriptase, protein synthesis and causes hemolysis of membranes (Wink et al. 1999)." [Reigosa Alleleopathy]

"a-Solanine and a-chaconine have been studied for their membrane disrupting properties (Roddick et al., 1988; Roddick and Rijnenberg, 1986, 1987). o-Chaconine disrupts phosphatidyl/cholesterolliposomes, whereas a-solanine had very little activity; however, a mixture of these alkaloids had a clearly stronger effect." [Roberts Alk]

Solanum americanum

"The most important chemical contained is the glycosidal alkaloid solanine. The antibiotic activity of the plant is attributed to this substance." [Roth SAMP]

"Unripe fruits are toxic, but as the fruit ripens, the alkaloid content decreases, similarly as in the leaf; adult leaves are used as a vegetable." [Roth SAMP]

Solanum dulcamara - Bittersweet

"Bittersweet woods nightshade is common in Europe and is characterized by its steroidal alkaloids and glycosides such as solanine and soladulcidine (58). Whereas they are abundant in green tissue, they are almost absent from red, ripe fruits." [Roberts Alk]

"Symptoms caused by the glycoalkaloid solanine and its aglycone, solanidine, follow the eating of 4–5 berries. The first symptom is a harsh feeling in the mouth and throat. Then comes vomiting and diarrhoea, spasms and fever. After more severe intoxication, which is very rare, there will be blood in the faeces and urine, paralysis and unconsciousness and respiratory paralysis." [Sandberg NR]

Solanum nigrum - Black Nightshade

"Parts of this plant can be highly toxic to livestock and humans. All parts of the plant except the ripe fruit contain the toxic glycoalkaloid solanine [11] and consumption of unripe fruits can result in toxicity with solanine-like poising symptoms (see Chapter 21). It has been stipulated that the cooked ripe fruit of black Solanum nigrum is safe to eat; however, it was found that detoxification cannot be attributed to normal cooking temperatures because the decomposition temperature of solanine is much higher at about 243oC [86]. Solanum nigrum leaves are recommended to be boiled as a vegetable with the cooking water being discarded and replaced several times to remove toxins...." [Kuete TSAMP]

"...different parts of S. nigrum cause a mild to a severe toxicity, which is mainly associated with the glycoalkaloids and nitrates. Solanine is a common alkaloid causing the toxic effects. The solanine toxicity is due to its interaction with mitochondrial membrane that decreases membrane potential and increases concentration of k+ in cytoplasm, which results apoptosis and cell damage. Nitrates present in S. nigrum tissues cause N-NO toxicity and interact with –N-H groups. Some symptoms of toxicity are diarrhoea, nausea, headache, burning of throat inflammation, joint pain, thyroid problem, jaundice and loss of sensation and potentially cause paralysis and death. Alpha-solanine causes neurological and gastrointestinal disorders at a dose more than 200 mg/kg of fresh berries. Toxic symptoms start to appear at a dose of 2–5 mg/kg and high dose up to 3–6 mg/kg is considered fatal (Jagtap et al. 2013). Green unripe berries are generally more toxic than ripe berries. By boiling the plant, toxic compound can be destroyed (Jain et al. 2011)." [Kunwar EH]

"The level of solanine is reduced if forage is made into silage (71) presumably by formation of the less-toxic solanidine." [Majak SPPWC]

"Nicholson et al. (60) used laboratory silos to evaluate potato top silage, adding about 2/3 other feed to absorb water, and found the product palatable to sheep and much lower in solanine than predicted from the content of the fresh plant." [Majak SPPWC]

"The whole plant is toxic due to the occurrence of the alkaloid solanine, giving the same symptoms as Bittersweet." [Sandberg NR]

Solanum tuberosum - Potatoes

"In unripe potatoes (Solanum tuberosum) the glycoalkaloids a-solanine and a-chaconine are derived from the widely occurring aglycone solanidine." [Pengelly TCMP]

"Potatoes contain a toxic glycoalkaloid, solanine, existing as α-, β- and γ-forms, the concentration of which is higher in the skin (8 mg/100 g) and much lower in the interior of the tuberculum (FDA 2014a). Still according to the US Food and Drug Administration (FDA), the toxic dose (to an average adult) is 20–25 mg, which is rarely reached. Increased amounts of solanine in potatoes have been associated with unusual features, such as a pink colour developing on the cut surface, or a brownish line near the surface, or when sprouting. Exposure of potatoes to light favours the production of solanine, in opposition to ordinary storage in the dark, at room temperature and low moisture. (FDA 2014a)." [Delgado CMD]

"Kuhn and co-workers (1955a,b) subsequently showed solanine to be composed of two glycosides of solanidine, a-chaconine (1177) and a-solanine (1174). These two alkaloids represent up to 95% of the total alkaloids in leaves of S. tuberosum and S. chacoense. In addition, B- and y-forms of solanine and chaconine possessing a shortened chain are present, together with a-solamarine, 0-solamarine and dernissidine. More than 95% of the total glycoalkaloid content of commercially available potato tubers consists of a-solanine and a-chaconine (Morgan et al. 1985)." [Hostettmann Saponins]

"The substance that sometimes appears as a greenish cast under the skin and in the eyes of the potato is the alkaloid solanine, the natural pesticide that protects the plant as it grows. All potatoes contain trace amounts (1–5 mg). Its appearance on store-bought potatoes means they have been “light-struck,” exposed either to natural or artificial light. According to Federal Food and Drug Administration guidelines, levels higher than 20 mg per 100 g of potato make the vegetable unfit to eat. Consequences of solanine toxicity range from minor upset stomach to serious illness. To avoid this, proper storage and cutting away all traces of green on the potato are necessary." [Katz EFC]

"The compound solanine is found in the eyes and peel of potato and if sunburned (green under the skin) or blighted, solanine levels can increase sevenfold, sufficient to harm a small child. Cooked potatoes with high concentrations of solanine have a bitter taste and can cause a burning sensation in the throat. Solanine has been shown to exhibit teratogenic effects in animals." [Omaye FNT]

"Conventional plant breeding may also cause rearrangements of the genome and result in production of previously unknown toxins, antinutrients, or allergens. Examples, though uncommon, include insect-resistant celery, which accumulates psoralen in response to light and thereby causes skin burns (Ames and Gold, 1999), and the Magnum Bonum potato, which accumulates toxic levels of solanine in cool weather (Van Gelder, Vinke, and Scheffer, 1988)." [Sharma BAPM]

Detoxification

"Ingestion of green potatoes or potato sprouts can cause various symptoms which can be severe in some cases." [Kuete TSAMP]

"Poisoning from cultivated pota- toes occurs very rarely however, as the toxic compounds in the potato plant are, in general, concentrated in the green portions of the plant and in the fruits and culti- vated potato varieties contain lower toxin levels [89]. Furthermore, it was found that at high temperatures (over 170oC) or during cooking, the toxin is partly destroyed". [Kuete TSAMP]

"Traditionally in the Mediterranean countries, potatoes are peeled and very often boiled in water, strongly decreasing the already small risk of food poisoning. Solanine is soluble in water and diffused by boiling but not eliminated when potatoes are baked in their skin (FDA 2014a)." [Delgado CMD]

"Solanine content in potatoes exposed to sunlight was increased as high as eight times that found in potatoes stored in the dark. The concentration of solanine obtained with varieties grown in the desert and exposed to sunlight during harvest reached levels of 150 and 90 mg/100 g, far above what has been found in other markets. Levels of solanine above 20 mg/100 g of fresh tuber are considered toxic." [Lichtfouse SAR 15]

"It is also significant to note that solanine is not destroyed by cooking (Baker et al., 1955), and the poisoning of livestock has sometimes been observed even with cooked potatoes (Kingsbury, 1964)." [Liener TCPF]

Pest Defence

"[Solanine] has fungicidal and pesticidal properties, and it is one of the plant’s [Solanum melongena] natural defenses." [Kuete TSAMP]

"Potatoes produce the steroidal alkaloid solanine, which seems to protect the tubers and foliage from some predators and insects. Still, potatoes are vulnerable to such pests as the Colorado potato beetle, red slugs, and blister beetles, and are still attacked by blight. Since 1990, fungicide-resistant strains of blight have struck fields in various parts of North America." [Katz EFC]

"Potato fruits look like green cherry tomatoes but are full of solanine, a poison that is part of the plant’s defense system—it prevents pests from eating the seeds. As a rule modern farmers ignore the seed, instead cutting up tubers and planting the pieces." [Mann 1493]

"In potato, concentrations of the glycoalkaloids, solanine and chaconine are associated with resistance to E. fabae (Sanford et al., 1992)." [Sharma BAPM]

"Tomatine and solanine, the steroidal alkaloid glycosides from Solanum tuberosum and Lycopersicon esculentum, and their aglycone tomatidine and solanidine exhibit antifeedant properties (Dahlman and Hibbs 1967). These compounds are attracting renewed interest because of their arthropod resistance and interesting insecticidal and nematicidal action." [Singh APB]

Antifungal

"In solamargine and chaconine the sugar is chacotriose, whereas in solasonine and solanine it is solatriose. The synergism of a-solanine and o-chaconine has also been proven for the antifungal activity of these alkaloids (Fewell and Roddick, 1993). The synergistic effect is over a wide range of ratios (10-20% of either compound) and is much less affected by a decrease in pH than are each of the individual compounds." [Roberts Alk]

Commercial Exploitation

"The major alkaloidal component in many Solanum species is solasodine (Figure 6.133). It is present as glycosides in the leaves, and especially in the unripe fruits. Solasodine may be converted into progesterone by means of the Marker degradation shown in Figure 5.118 (see page 281). Trial cultivations of a number of Solanum species, including Solanum laciniatum and Solanum aviculare (indigenous to New Zealand), Solanum khasianum (from India), and Solanum marginatum (from Ecuador), have been conducted in various countries. Alkaloid levels of 1–2% have been obtained. These plants are especially suitable for long-term cultivation if the fruits provide suitable quantities, being significantly easier to cultivate than disogenin-producing Dioscorea species." [MNP Dewick]

Lore

"Solanine, contained in the tubers and common to all plants in the nightshade family, is indeed a poison. Unlike modern potatoes, which contain only a nonharmful trace amount, tubers of the sixteenth and seventeenth centuries had much higher levels, not enough to cause death, but sometimes a rash appeared. That led to its association with the deadliest disease of the time, leprosy. So great was the fear that, when Frederick the Great of Prussia ordered his people to plant potatoes in 1744, they pulled them up. Frederick was forced to post soldiers to guard the crops. Ten years later, in 1754, the king of Sweden also ordered his subjects to grow potatoes. Yet, when famine struck Kolberg in 1774, wagonloads of potatoes sent by Frederick were rejected." [Katz EFC]

Sparteine

 

Veratridine

(Steroid-derived alkaloid)

Distribution

References

Vincamine

See also: Vinca Alkaloids page [page created]

Indole alkaloid (distinctively a tryptamine) [Arora MPB]

Distribution

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]

Activities

Properties:

References