Polyacetylenes

Cicutoxin

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

Distribution

Activities

Properties

Notes:

Toxicology

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

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

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

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

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

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

Dermal Absorption

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

Effect on Animals and Livestock

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

References

Falcarinol

(polyacetylene alcohol) [Polya BTPBC]

Distribution

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

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

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

Hazards

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

Activities

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

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

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

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

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

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

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

Misc Studies

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

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

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

Related Compounds

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

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

References

Oenanthotoxin

Sources: Hemlock Water Dropwort - Oenanthe crocata [T3DB]

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

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

Hazards

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

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

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

Treatment of Poisonings

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

References