LSA The Psychoactive Ergot Alkaloids and their occurrence in the Microfungi. M. P. Bock and D. G. Parbery Abstract There are 80 or more ergot alkaloids, many of which have been proved to have, or are suspected of having a psychoactive effect. In the fungi these alkaloids are found in the microfungi and at least two species have been used as entheogens while a few species have also caused accidental poisoning in humans. The presence of the Clavicipitaceae in Australia and New Zealand is also discussed. Introduction Microfungi containing the ergot alkaloids have been used by mankind for many reasons throughout history. Mostly the fungi were used as medicines for assisting childbirth, inducing abortions and to relieve headaches and sprains (Ott, 1993). However, Claviceps purpurea and Balansia cyperi have been used as entheogens (shamanic intoxicants and vision inducing substances) by the Greeks (Wasson et al., 1978) and Peruvian natives (Plowman, 1990) respectively. Other cultures have used plants which contain ergot alkaloids for both their medicinal and psychoactive effects. Seeds of various vines of the Convolvulaceae were used by the Aztec priests of central America (Schultes & Hofmann, 1979) and roots of Tchunfki (Securidaca longipedunculata in the Polygalaceae) which are used by the Balanta people of Guinea Bissau for their `psychotropic' effect (Filippini & Allegri in Costa et al., 1992). The common feature in the use of ergot alkaloids as entheogens is that they are not eaten, but rather the alkaloid containing material, plant or fungus, is ground to a powder which is soaked in water, which is then filtered. The solid residue is discarded and the water is drunk (Ott, 1993). The Psychoactive Ergot Alkaloids This group contains five compounds known to be psychoactive in humans, these are ergine, isoergine, ergonovine, elymoclavine and lysergol. Ergine (LA 111) produces a entheogenic effect with sedative side-effects (Hoffman, 1963). Ergonovine also produces a entheogenic effect (Bigwood et al., 1979). Elymoclavine is the probable entheogenic alkaloid of Tchunfki (Costa et al., 1992). Lysergol has also been found to be weakly entheogenic in experiments on humans (Heimann, 1965). Isoergine produces sedative effects and `a feeling of mental emptiness and of the unreality and complete meaningless of the outside world' (Hoffman, 1971). Animal experiments have shown that elymoclavine, lysergol, LSD and several other ergot alkaloids such as agroclavine, triseclavine, penniclavine, lysergine and lysergene have excitory effects on the central nervous system (Yui & Takeo, 1958a) as well as lysergic acid hydroxyethylamide which also excites the central nervous system in animals (Glasser, 1961). The effects of agroclavine are similar to those of elymoclavine and LSD on rabbits (Yui & Takeo, 1958b), indicating that the effect of agroclavine may well be psychoactive in humans as well. It also seems likely that agroclavine, triseclavine, penniclavine, lysergine and lysergene and lysergic acid hydroxyethylamide will be psychoactive in humans. Even ergot alkaloids such as chanoclavine and ergonovine which do not produce psychoactive effects when administered in low doses (Hoffman, 1963) cannot be ruled out as not being psychoactive in humans in high doses, which is what happens with ergonovine at high doses (Bigwood et al., 1979). The Fungi Clavicipitaceae Acremonium coenophialum Morgan-Jones et Gams Acremonium sp. Balansia claviceps Speg. (Black Crust) Balansia epichloë (Weese) Diehl Balansia henningsiana (Möller) Diehl Claviceps africana Frederickson, Mantle et de Milliano Claviceps cynodontis Langdon (Bermuda Grass Ergot) Claviceps fusiformis Loveless (Pennisetum Ergot) Claviceps gigantea Futentes, de Lourdes, Ullstrup et Rodrigues (Maize Ergot) Claviceps imperatae Tanda et Kawatani (Blade Grass Ergot) Claviceps litoralis Kawatani (Hama-garlic Ergot) Claviceps microspora Tanda Claviceps miscanthi Sawada Claviceps paspali Stevens et Hall (Paspalum Ergot) Claviceps purpurea (Fr.) Tul. (Rye Ergot) Claviceps purpurea var. sasae Tanda (Bamboo Ergot) Epichloë typhina (Pers. ex Fr.) Tul. (Choke) Hypocreaceae Hypomyces aurantius Fckl. (Golden Hypomyces) Trichocomaceae Aspergillus fumigatus Penicillium aurantio-virens Biourge Acremonium coenophialum contains ergine as well as ergovaline (Porter, 1995) also with various clavine alkaloids such as chanoclavine, agroclavine and penniclavine (Lyons et al., 1986). An Acremonium sp. is known to induce an effect on horses eating Sleeypygrass, Stipa robusta, and this Acremonium sp. has been found to contain ergine, isoergine, ergonovine as well as 8-hydroxylsergic acid amide and chanoclavine (Petroski et al., 1992). The only described species of Acremonium which is known to infect the genus Stipa is A. chisosum which infects S. eminens. Balansia claviceps contains ergonovine as well as chanoclavine (Porter et al., 1979). Balansia epichloe contains the psychoactive alkaloids ergonovine and elymoclavine, along with other alkaloids such as agroclavine, chanoclavine and penniclavine (Porter et al., 1979). Balansia henningsiana contains ergonovine (Bacon et al., 1981) Claviceps africana contains traces of the alkaloids elymoclavine and agroclavine as well as several other clavine alkaloids (Mantle, 1968). An ergot species, Claviceps strain 178 growing on Cynodon dactylon was found to contain ergonovine and penniclavine (Porter et al., 1974). Claviceps cynodontis is the only ergot species known to infect the Cynodon genera. C. fusiformis contains elymoclavine, lysergol as well as agroclavine, penniclavine, lysergene and many other alkaloids (Agurell & Ramstad, 1962). It is also the only ergot species known to contain alkaloids in its honeydew (Kumar & Arya, 1978). C. gigantea contains elymoclavine, agroclavine and other ergot alkaloids (Agurell et al., 1963). C. imperatae contains agroclavine, ergonovine and other ergot alkaloids (Tanda & Kawatani, 1976). C. litoralis, the ergot of Elymus mollis, is the richest source of ergot alkaloids known in review by Tanda & Kawatani (1980) which also mentions a paper which records ergonovine. Other alkaloids of C. litoralis include elymoclavine and agroclavine which were detected by Abe et al., (1955a), penniclavine and triseclavine in Abe et al., (1955c), and lysergol as well as lysergene in Abe et al., (1961). However it possible that confusion can arise with C. purpurea as both species parasitise E. mollis. C. microspora contains elymoclavine agroclavine and several water-insoluble ergot alkaloids (Abe et al., 1955b). C. miscanthi contains elymoclavine, ergonovine, agroclavine and several water-insoluble ergot alkaloids (Tanda, 1991). C. paspali submerged cultures have ergine, isoergine and lysergic acid N-1-hydroxyethylamide (Arcamone et al., 1960) while sclerotia from Australia contain up to 0.005% alkaloids composed of ergine and ergonovine along with chanoclavine and two unidentified ergoline alkaloids (Groger et al., 1961). Elymoclavine (Kobel et al., 1964) and agroclavine (Brar et al., 1968) have also been recorded. C. purpurea is the most extensively studied of the ergots and has been shown to produce a wide range of ergot alkaloids. Many reviews of its chemistry/pharmacology exist including Willaman & Hui-Lin (1970) and Parbery (in prep.). Lysergine is recorded by Abe et al. (1961). C. purpurea var. sasae, is different enough in morphology and host range from C. purpurea to be considered a separate species in the genus Claviceps. It contains elymoclavine, ergonovine and agroclavine (Tanda, 1973a). C. sorghi Kulkarni et al. is known to contain traces of the suspected psychoactive alkaloid agroclavine in cultured media (Frederickson et al., 1991). Epichloe typhina has been found to contain the psychoactive ergoline alkaloid elymoclavine along with penniclavine, agroclavine, festuclavine, ergovaline and ergovalinine (Porter et al., 1981). Hypomyces aurantius is known to contain the psychoactive alkaloid elymoclavine with two other clavine-type ergot alkaloids agroclavine and chanoclavine and two peptide-type ergot alkaloids (Yamatodani & Yamamoto, 1983). Aspergillus fumigatus in the Fungi Imperfecti contains elymoclavine and agroclavine along with alkaloids of unknown activity such as chanoclavine (Yamano et al., 1962) and festuclavine (Spilsbury & Wilkinson, 1961). Penicillium aurantio-virens contains penniclavine and agroclavine (Solov'eva et al., 1995). Possibly active other Microfungi Of the untested or not completely tested microfungi besides Balansia cyperi, other fungi in the Clavicipitaceae are used in rituals such as a species of Cordyceps, C. capitata an insect infecting fungus which may be psychoactive and it is known to contains alkaloids (Ott, 1993). Also C. ophioglossoides is also known to be alkaloid positive (Spilsbury & Wilkinson, 1961). Poisonings in Humans Only two species of ergot have been recorded as causing outbreaks of poisoning in humans when eaten in contaminated grains during times of food shortages. These are Claviceps fusiformis which causes acute nausea, vomiting and mild transient neurotoxicity when pearl millet (Pennisetum typhoides) in India is consumed (Krishnamachari & Bhat, 1976), also agalactia (failure to produce milk) is found in sows which eat C. fusiformis (Shone et al, 1959). The other species is C. purpurea which has caused many effects in humans when eaten in contaminated rye as has happened throughout European history. These effects include abortion, agalactia, convulsions, gangrene and limb loss, hallucinations, hyperthermia, muscular spasms, respiratory difficulty and death (Bove, 1970). Occurrence of Ergots in Australia and New Zealand Ergots Host Genera Claviceps *africana Sorghum spp. annulata Eulalia fulva *cynodontis Cynodon spp. glabra Digitaria spp. hirtella Barchiaria and Eriochloa spp. inconsipicua Hyparrhenia filipiendula nigricans Eleocharis spp. *paspali Paspalum spp. phararidis1 Dactylis, Danthonia, Lolium, Phalaris and Vulpia spp. platytricha Ischaeumum australe purpurea Many species in at least 80 pooid genera including Agropyron, Agrostis, Ammophila, Avena, Austrofestuca, Bromus, Dactylis, Danthonia, Dichelachne, Distichlis Echinopogon, Elymus, Eragrostis, Festuca, Holcus, Hordium, Lolium, Microlaena, Phalaris, Phleum, Phragmites, Poa, Polypogon, Secale, Triticum, Vulpia plus panicoid species in Pennisetum pusilla Bothriochloa, Capilliedium, Chrysopogon, Cymbopogon, Dichanthium, Heeteropogon, Hyparrhenia, Sorghum, Themeda, Vetiveria queenslandicum Paspalum orbiculare sulcata Barchiaria spp. Bold species have been tested for alkaloids. 1, this species exhibits several balansoid features in addition to clavicepitoid features. Apart from the three introduced species, there are two other species that may have been introduced, C. purpurea which is transported by man along with pasture grasses or grains. In Australia it occurs in three species of native grass, Microlaena stipoides (Langlon, 1960), Agropyron scabrum (Langlon, 1952) and also Austrofestuca littoralis (Warcup & Talbot, 1981). So it may be an introduced species which crossed to the native species, or it may be a native species. The other species, C. pusilla was originally recorded in Italy in 1851 on a Bothriochloa species, B. ischaemi. While in Australia and in South Africa it has been found on numerous andropogonoid hosts (Langdon, 1941 and Loveless, 1964). So it is possible that it was transported to Europe by returning expatriates or to the European colonies by settlers and has then spread to other hosts. In Australia there are endemic balansoid fungi associated with native tropical grasses in Queensland (Ryley, 1986) and also Balansia epichloe, which grows on an introduced Adropogon species. Agronomists in northern Queensland have been aware for many years, that cattle on native pastures in some seasons either develop peculiar signs of intoxication or become unthrifty for no apparent reason. It is possible that at least some of these problems are associated with balansoid endophytes of grasses, or ergots, but no studies have been conducted. While in New Zealand there are known to be two species of introduced fungi with active alkaloids that infect grasses, these are Acremonium coenophialum which grows on Festuca arundinaceae and Epichloe typhina which grows on F. rubra (Latch et al., 1984). References Abe, M., Yamano, T., Kozu, Y. & Kusumoto, M. 1955a. Production of alkaloids by ergot from Elymus mollis. J. Agric. Chem. Soc. Japan 29, 364-369. 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