Phytochemicals

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Phytochemicals

These are a few of the pharmacologically significant phytochemical and mycochemical compounds which may be present in our local species. The aim of the chemical profile 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.

Sections

Alcohols

Cicutoxin
Falcarinol

Name:

Distribution:

Cicutoxin

  • Cicuta maculata
  • Activities
  • Properties:

References

Name:

Distribution:

Falcarinol

  • Falcaria vulgaris (Umbelliferae/Apiaceae)
  • Oenanthe crocata
  • Hedera helix (Araliaceae)
  • Activities
  • Properties:

References


Alkaloids

"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]

Name:

Distribution:

Berberine

  • Berberine is from the protoberberine group of isoquinoline alkaloids [Ramawat NP]
  • "Pharmacological data also suggest that combining berberine-containing herbs with other botanical synergists might prove even more effective." (CBMed)
  • Berberine salts have been used in ophthalmic products, usually in eye drops and eyewashes. [Leung ENCI]
  • Interactions:
    • Ciclosporin: "Berberine appears to increase the bioavailability and trough blood levels of ciclosporin.... Although the increase in ciclosporin levels is not sufficiently severe to suggest that the concurrent use of berberine should be avoided, it may make ciclosporin levels less stable." [HMI Stockey]
    • Paclitaxel: An in vitro study found that pre-treatment with berberine blocked the anticancer effects of paclitaxel in six cancer cell line cultures (oral cancer, gastric cancer and colon cancer).1 [HMI Stockey]
  • Berberis spp. (barberry) (roots and stem bark)(CBMed)[Ramawat NP]
    • B. aristata (tree turmeric) [Barceloux MTNS][Ramawat NP]
    • B. vulgaris (barberry) [Barceloux MTNS]
  • Coptis spp. (goldthread) (roots and stem bark)(CBMed)
    • Coptis chinensis (coptis or Chinese goldthread) [Barceloux MTNS][Ramawat NP]
  • Corydalis speciosa [Ramawat NP]
  • Corydalis yanhusuo [Ramawat NP]
  • Hydrastis canadensis (goldenseal) (roots and stem bark)(CBMed)[Ramawat NP]
  • Mahonia Sp.
    • M. aquifolium 0.03 % to 0.97 % [PWMP](CBMed)[Ramawat NP]
    • M. nervosa 0.03 % to 0.97 % [PWMP]
    • M. repens [Elsevier ASOL]
  • Phellodendron amurense [Ramawat NP]
  • Tinospora cordifolia [Ramawat NP]
  • Argemone mexicana L. (prickly Poppy) (found to a lesser extent) [Ramawat NP]
  • Eschscholzia californica - California poppy (found to a lesser extent)[Ramawat NP]
  • Activities
    • Active against the mutagen 'Acridine orange' <[ModPhyt]
    • berberine has a mild mutagenic effect (PDR)
    • amoebicidal [Pengelly TCMP][HMI Stockey]
    • antibacterial [Pengelly TCMP] bactericidal [HMI Stockey]
    • antifungal [Pengelly TCMP] fungicidal [HMI Stockey]
    • antiarrhythmic [Pengelly TCMP]
    • antiinflammatory [Pengelly TCMP]
    • antitumor [Pengelly TCMP]
    • antiviral [Pengelly TCMP]
    • cholagogue [Pengelly TCMP]
    • elastase inhibitor [Pengelly TCMP]
    • hepatoprotective-tyramine inhibitor [Pengelly TCMP]
    • Berberine is also said to possess some antiepileptic, uterine stimulant and hypotensive effects, and is slightly sedative.[HMI Stockey]
    • "Berberine has antifibrillatory activity, elevating the ventricular fibrillation threshold to electrical stimulation in anesthetized cats.9 Berberine also has anticonvulsant, sedative, uterine stimulant, and numerous other activities". [Leung ENCI]
  • Properties:
    • "Berberine, universally present in rhizomes of Mahonia species, has marked antibacterial effects[218] and is used as a bitter tonic[213]. Since it is not appreciably absorbed by the body, it is used orally in the treatment of various enteric infections, especially bacterial dysentery [218]. It should not be used with Glycyrrhiza species (Liquorice) because this nullifies the effects of the berberine[218]. Berberine has also shown antitumour activity[218]." (PFAF)
    • "...can be regarded as potent allelochemicals that are toxic to bacteria and fungi, as well as other plants, insects and animals (Schmeller et al. 1997)." [Pengelly TCMP]

References

  • [PWMP] The Potential for Mahonia nervosa as a Wildcrafted Medicinal Product in the Pacific Northwest, Amy T. Grotta, Oregon State University Extension Service, 505 N. Columbia River Hwy., St. Helens, OR 97051, USA, Published Online Feb 23, 2013, Economic Botany.
  • (PFAF)http://www.pfaf.org/user/Plant.aspx?LatinName=Mahonia+nervosa, Accessed Dec 30, 2014

Name:

Distribution:

Cytisine

(Quinolizidine Alkaloid)

  • Laburnum Sp. [MNP Dewick]
  • Cytisus scoparius
  • Mescal bean - Sophora secundiflora [Prance CHP]
  • The pyridone-type alkaloids, i.e., anagyrine, cytisine, etc., are derived from lupanine. [Bajaj MAPS 6]
  • Laburnum anayyroides(laburnum) [seed], Lupinus alba, Baptisia, Cytisus, Genista, Sophora, Therrnopsis, Spartium, Ulex spp. (Fabaceae) [Polya BTPBC]
  • The entire Baptisia plant contains numerous alkaloids, but especially cytisine (Lampe and McCann 1985). Since Baptisia is used in modern herbal preparations in Europe, that is where most recent poisonings have taken place (Foster and Caras 1994). [Daniel F. Austin]

Hazards

  • Teratogenic - cytisine has teratogenic activity in rabbits. [SEHM] α-Pyridone QAs (e.g., anagyrine, cytisine) are not only more toxic than the corresponding saturated QAs, but have also been implicated as teratogens in higher animals. [Rosenthal HerbV1]

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]

  • (+)-Cytisine (30), from Cytisus scoparius L., has been found to be a selective and specific probe for the nicotinic-type acetylcholine receptor (nAChR) as a partial agonist and has served as the lead compound for varenicline (31), a drug recently approved by the FDA for smoking cessation.94 [IKAN STCNP]
  • cytisine - amoebicidal [Nagata MAPS 12]
  • Anti-inflammatory; molluscicide; psychoactive; LDso 101 (oral, mus). [Nigg PRMA]
  • Insecticide: The quinolizidine alkaloid cytisine, which has nicotine-like activity, has also been used in the U.S.S.R. as an insecticide.[Bajaj MAPS 1]
  • cytisine is an agonist of the nicotinic AChR [Seeram HM]
  • Thermopsis alterniflora - Fabaceae - Toshkent province of Uzbekistan, in the Western Tien Shan; Osh and Jalal-Abad provinces of Kyrgyzstan.
    • The alkaloid cytisine is used to prepare a 0.15 % solution, called cytion, which is used to increase respiration in cases of respiratory standstill, such as during operations and traumas, from infectious diseases, shocks, various intoxication (such as poisoning by carbon oxide, prussic acid, and narcotics), asphyxia of newborns, and others. [Eisenman MPCA]

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<s>/2 mm., [a]"o -</s> 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]

  • Quinolizidine alkaloids strongly inhibit germination of lettuce seeds. Alkaloid esters, for example, 13-tigloyloxylupanine, inhibited gennination completely at a concentration of 6 tuM (Wink, 1983b). Sparteine and cytisine inhibit radicle growth in Lepidium (Wink, 1993b). [Seiger PSM]
  • cytisine of respiratory stimulant effect (Laburnum species) [Ramawat NP]
  • The LD50 i.p. for cytisine in mouse is 9.3 mg/kg [Seiger PSM]

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]

Name:

Distribution:

Slaframine

(indolizidine alkaloidal)
(mycotoxin)

"Trifolium pratense (red clover) may become infected with the fungus Rhizoctonia leguminocola(black patch disease), especially in wet, cool years.... Slaframine is an indolizidine alkaloid recognized as the toxic principle, and it is stable in dried hay and probably in silage. Horses are highly sensitive to slaframine, but clinical cases occur in cattle as well.... Morbidity can be high, but death is not expected, and removal of contaminated hay allows recovery and return of appetite within 24–48 hr." [Merck]

"A related alkaloid, swainsonine, produced by R leguminicola, has caused a lysosomal storage disease from prolonged exposure, but its importance in the salivary syndrome is not confirmed. Diagnosis is tentatively based on recognition of the characteristic clinical signs and the presence of “black patch” on the forages. Chemical detection of slaframine or swainsonine in forages helps to confirm the diagnosis. There is no specific antidote to slaframine toxicosis, although atropine may control at least some of the prominent salivary and GI signs."[Merck]

"Slaframine is an indolizidine alkaloidal mycotoxin that generally causes salivation (slobbers) in most animals. It is usually produced by the fungus Rhizoctonia leguminicola. It is a common fungal pathogen of red clover (Trifolium pratense) that causes black patch disease in the plant... wet and humid weather are the favorable environmental condition for the growth of the fungus and production of slaframine. Legume hays contaminated with slaframine causes slobber syndrome and the various animals are sensitive to its effects.[3]" (Wiki)

 

"The fungus is ubiquitous in soil and parasitizes red clover (Trifolium pratense), white clover (Trifolium repens), alsike clover (Trifolium hybridum), and many other legumes." [Gupta SDPME] "Rarely, other legumes (white clover, alsike, alfalfa) may be infected." [Merck]

"Spring and fall are ideal for the growth of R. leguminicola." [Gupta SDPME]

 

Metabolism

"Liver is the major site of slaframine metabolism where it has been suggested that slaframine is metabolized in the liver by a microsomal flavoprotein oxidase to the ketoimine metabolite consisting of quaternary nitrogen separated from an acetate ester by two carbon atoms."(Wiki)

 

Toxicity

"In horses, excessive salivation is usually the first sign of slaframine exposure. Signs typically develop within hours of exposure. The Slaframine poisoning or slobbers likely occur in a cooler and wetter spring or fall because these seasons are ideal for the growth of the fungus Rhizoctonia leguminicola. The other clinical signs associated with the "slobbers syndrome" include salivation, lacrimation, feed refusal, bloating, stiff joints, diarrhea, and weight loss.
The clinical signs of slaframine toxicity are similar in all species. When animals are fed with slaframine contaminated forage then they salivate profusely. The experiment shows that a single dose of slaframine produces salivation for 6–10 hours. However, clinically affected animals can slobber for several days because they are fed with continued slaframine contaminated forages. Various other animals like sheep, swine, and guinea pigs were also found to suffer from Cyanosis and open-mouth breathing under experimental conditions in sheep, swine, and guinea pigs. Pigs were also observed to vomit, became dyspneic, and collapse with stiffened pelvic limbs.[2]"(Wiki) "... signs also include mild lacrimation, diarrhea, mild bloat, and frequent urination."[Merck]

"Interestingly, the compound does decrease in red clover hay while in storage. One study sites a decrease in 10 months of storage from 50-100 ppm to 7 ppm." [Perdue.edu]

 

Diagnosis & Treatment

"Generally, diagnosis of slaframine toxicity is done by observation of clinical signs (salivation) in animals consuming legume forage, particularly red clover hay. Further tests such as isolating in cultures can be done to identify the fungus Rhizoctonia leguminicola in the hay.... Slowly, the slobber symptoms recover when the contaminated hay is removed, however clinical signs may persist for 1–2 days following removal of the toxic forage. In severe cases, atropine may be of benefit that helps in reversing the parasympathomimetic effects of slaframine, however it is unlikely to be completely resolving clinical signs.[2]"(Wiki)

"Clinical signs in cattle, in addition to salivation, are lacrimation, bloating, frequent urination, and watery diarrhea. other clinical signs may include anorexia as well as irregularities in the gastrointestinal, cardiac, and respiratory systems. Weight loss, decreased milk production, uterine hemorrhage, and abortions have also been associated with slaframine toxicosis. fatalities with slaframine toxicosis are not common. However, death may occur due to suffocation from pulmonary edema and/or emphysema." [Gupta SDPME]

References

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]

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]

Potatoes

"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]

Name:

Distribution:

Solanine

(Steroidal Alkaloid)

  • Solanum
  • Activities
  • Properties:

References

Name:

Distribution:

Sparteine

  • Activities
  • Properties:

References

Name:

Distribution:

Veratridine

(Steroid-derived alkaloid)

  • Schoenocaulon officinale - Seed (2500.0-15000.0) [DukePhyt]
  • Veratrum viride - Root [DukePhyt]
  • Veratrum album - Plant [DukePhyt]
  • Activities
  • Properties:

References

Name:

Distribution:

Vincamine

Indole alkaloid (distinctively a tryptamine) [Arora MPB]

  • Vinca minor (major constituent of aerial parts) [Arora MPB]
  • Vinca major [Arora MPB]
  • Catharanthus roseus [Arora MPB]
  • Crioceras longiflorus [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]

  • Activities
    • hypotensive [Arora MPB](PDR)
    • negatively chronotrophic [Arora MPB](PDR)
    • spasmolytic [Arora MPB](PDR)
    • hypoglycaemic [Arora MPB](PDR)
    • sympatholytic [Arora MPB](PDR)
    • vasodilator (peripheral vasodilator) [Arora MPB]
  • Properties:
    • Melting Point: 232-233 deg C [Pubchem]
    • Solubility: In water, 62 mg/L @ 25 deg C /Estimated/ [Pubchem]
  • "observed effects of vincamine include cardiovascular effects (e.g. hypotension, proarrhythmogenic effect) and effects on central nervous system (sedation)." [Pubchem]
  • Cyanide Antidote: “Vincamine and it analogs were found ot be effective for treating cyanide intoxication, and it was concluded that this is a characteristic property of vincamine.” [TheAlkaloidschemandpharm]

References

Amino Acids

Lathyrogens

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]

"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)."

References

  • 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.com. Merriam-Webster, n.d. Web. 3 Sept. 2016.

Enzymes

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]

References

Name:

Distribution:

Thiaminase

  • Equisetum arvense [Cornell]
  • Pteridum aquilinum - Bracken [Cornell]
  • Marsilea drummondii - Nardoo [Cornell]
  • Raw flesh and viscera of certain fish and shellfish [Cornell]
  • Ferns & Some bacteria [Cornell]

References

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)

References

  • (Wiki) Essential Fatty Acid, https://en.wikipedia.org/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.

Name:

Distribution:

Linoleic acid

(Essential Fatty Acid)

  • Achillea millefolium (Leaf) [DukePhyt]
  • Aesculus hippocastanum (Leaf) [DukePhyt]
  • Aesculus hippocastanum (Seed) Up to 6415.0 ppm [DukePhyt]
  • Alliaria petiolata(Seed) Up to 48400.0 ppm [DukePhyt]
  • Allium schoenoprasum (Leaf) 2220.0 - 27750.0 ppm [DukePhyt]

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)

  • Activities
  • Properties:
    • Melting point: −5 oC (23 oF)[2], −12 oC (10 oF)[1](Wiki)
    • Boiling point: 230 oC (446 oF) at 21 mbar[2], 230 oC (446 oF) at 16 mmHg[1](Wiki)
    • Solubility in water: 0.139 mg/L[2](Wiki)

References

  • [DukePhyt] LINOLEIC-ACID, https://phytochem.nal.usda.gov/phytochem/, Accessed Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press. Sept 3, 2016
  • (Wiki) Linoleic Acid, https://en.wikipedia.org/wiki/Linoleic_acid, Accessed Sept 3, 2016
    • [1] The Merck Index, 11th Edition, 5382
    • [2] Record of CAS RN 60-33-3 in the GESTIS Substance Database of the IFA
    • [3] Anneken, David J.; Both, Sabine; Christoph, Ralf; Fieg, Georg; Steinberner, Udo; Westfechtel, Alfred (2006). "Ullmann's Encyclopedia of Industrial Chemistry, Chapter: Fatty Acids". doi:10.1002/14356007.a10_245.pub2. ISBN 3527306730.
    • [4] Burr, G.O., Burr, M.M. and Miller, E. (1930). "On the nature and role of the fatty acids essential in nutrition" (PDF). J. Biol. Chem. 86 (587): 1–9.
    • [15] Diezel, W.E.; Schulz, E.; Skanks, M.; Heise, H. (1993). "Plant oils: Topical application and anti-inflammatory effects (croton oil test)". Dermatologische Monatsschrift. 179: 173.
    • [16]Letawe, C; Boone, M; Pierard, GE (March 1998). "Digital image analysis of the effect of topically applied linoleic acid on acne microcomedones". Clinical & Experimental Dermatology. 23 (2): 56–58. doi:10.1046/j.1365-2230.1998.00315.x. PMID 9692305.
    • [17]Darmstadt, GL; Mao-Qiang, M; Chi, E; Saha, SK; Ziboh, VA; Black, RE; Santosham, M; Elias, PM (2002). "Impact of topical oils on the skin barrier: possible implications for neonatal health in developing countries". Acta Paediatrica. 91 (5): 546–554. doi:10.1080/080352502753711678. PMID 12113324.

Flavonoids

"In the chloroplasts, flavonoids act as primary antioxidants to protect the delicate lightharvesting compounds from ultraviolet and free radical damage. In the human body, these same compounds act as antioxidants, anticarcinogens, and anti-inflammatories by virtue of their radical quenching activities." [BMWH]


Glycosides

"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]

References

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

Name:

Distribution:

Arbutin

  • C12H16O7
  • Other names; hydroquinone-b-D-glucopyranoside; hydroquinone glucose; arbutoside; ursin

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

References

  • [Merck] The Merck Index, 13th Ed. 2001 Merck & Co, New Jersey, U.S.A

Name:

Distribution:

Digitoxin

(Cardiac Glycosides)

  • Digitalis purpurea
  • Activities
  • Properties:

References

Name:

Distribution:

Ptaquilosides

  • 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]
  • Activities
    • Carcinogen
  • Properties:

References

  • [Potter CEP] Carcinogenic effects of ptaquiloside in bracken fern and related compounds,DM Potter and MS Baird, British Journal of Cancer(2000) 83(7), 914–920

Salicin

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

Distribution:

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]

References


Name:

Distribution:

Ibotenic acid

(ISOXAZOLE ALKALOIDS)

  • Amanita muscaria [ACB57]
  • Amanita pantherina [ACB57]
  • Amanita strobilis [ACB57]
  • "ibotenic acid and muscimol were found in clearly detectable concentrations in A. cothurnata, all specimens examined of A. muscaria, all specimens of A. pantherina, and in lower concentrationin A. gemmata(71)." [ACB57] "

"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]

  • Activities
    • Toxic: "Ibotenic acid is also responsible for a high percentage of poisonings of dogs, sometimes with fatal results. [Trudell MPNW]
    • "The effects of ibotenic acid often are described as inebriation, although quite differ ent from those produced by alcohol consumption. Effects usually begin between 30 minutes and 2 hours after the meal, but can take up to 6 hours in some cases. They peak about 2 to 5 hours later, and may last 8 to 24 hours. Nausea is usually the first symptom, sometimes accompanied by vomiting, especially in children. Other effects are incoordination, confusion, dizziness, difficulty in walking, and abrupt waxing and waning of activity, sometimes involving rather vigorous and excited outbursts. Muscle twitching, tremors, cramps, and spasms are common, and generalized seizures occasionally occur. Although true hallucinations seem not to occur, perception is altered such that objects often seem larger than they are or take on different colors. The final stage usually involves a deep coma-like sleep from which it is difficult to arouse the victim. usually there are no aftereffects, although sometimes a hangover headache occurs. In many cases, especially those involving children found grazing on a mushroom, the effects of treatment probably are more harmful than those of the mushroom. [Trudell MPNW]
  • Properties:
    • Hallucinogenic [albequerque 2015]
    • "Natural ibotenic acid is racemic." [ACB57]

References

  • ACB57 - The Alkaloids, Chemistry and Biology - Volume 57

Name:

Distribution:

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]

  • Amanita pantherina... contains minute amounts of muscarine (21)." [ACP23]
  • Clitocybe dealbata (Sow. ex Fr.) Kiimmer - 0.15% (dry wt of fruit) [ACP23]
  • Clitocybe rivulosa (Pers. ex Fr.) Kiimmer - 0.0 - 0.13 (dry wt of mycelium) [ACP23]
  • "Other mushrooms, particularly those of the genus Inocybe, contain varying amounts of muscarine, some in amounts larger than in the fly agaric". [ACP23] "...most, if not all, inocybes and several clitocybes.... Still others, from several different genera, either contain, or are suspected of containing, sufficient muscarine to cause poisoning, including Mycena pura and certain species of Boletus and Omphalotus." [Trudell MPNW]
  • "All stereoisomeric muscarines occur in nature. (-)-Allomuscarhe has been isolated from Amanita muscaria (36)and (+)-epimuscarinehas been found in Inocybe geophylla (27)." [ACP23]
  • Activities
  • Properties:

References

  • ACP23 - The Alkaloids, Chemistry and Pharmacology - Volume 23
  • ACP40 - The Alkaloids, Chemistry and Pharmacology - Volume 40

Name:

Distribution:

Muscimol

  • Amanita muscaria (fly agaric)[IKAN STCNP]
  • Activities
    • Hallucinogenic [albequerque 2015]
    • "Muscimol (57), a centrally acting principle of the mushroom Amanita muscaria (fly agaric), is known to be a potent GABAA receptor agonist and led to the development of a bicyclic analogue, gaboxadol, a drug currently in phase III clinical trials for the treatment of sleep disorders." [IKAN STCNP]
  • Properties:

References


Index


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Caution
The information presented on this site is provided for educational purposes. Self diagnosis and treatment, without due diligence, could be harmful and is not encouraged. Some information & images may be copyright. Every effort has been made to present the information in the spirit with which it was originally presented. Some data has been omitted for legal and/or practical consideration. There is some data not covered in the scope of this project, including, but not limited to, cell culture and large-dose animal studies. I have made comparisons and links between related species which may later prove erroneous. I have not verified the information for accuracy and I accept no responsibility for its authenticity. Many of the plants presented are poisonous, have poisonous properties, or could cause illness through misuse, allergic reaction, drug interactions and environmental contaminants. Please use caution and mindfulness when harvesting plants for any use.

Page last modified on 24-06-2017