Ergoline alkaloid

Serotonin acts as neurotransmitter in the brain of animals (E 3.2). It is, however, also of importance as a hormone for the maintenance of normal gut mobility in the gastro-intestinal tract (E 3.1). Serotonin accumulates in the trichomal fluid of the stinging nettle (Urtica dioica) which is injected into the body of animals breaking the hairs during predation of even touching. In addition to the other constituents of the nettle toxin, e.g., acetylcholine and histamine, it provides protection against predation (E 5.5.3). 5-Hydroxy-L-tryptophan and serotonin accumulate in the seeds and fruits of several plant species, e.g., bananas, pineapples, tomatoes and walnuts. At least in walnut seeds serotonin serves in the detoxication of ammonia during maturation and abscission of the fruits (E 2.2). 

5-Methoxytryptamine, found in the brain of animals, has neurophysiological activity (E 3.2). Melatonin, formed in the pineal gland, appears to effect the female gonads and may well be responsible for seasonal and diurnal rhythms (E 3.1). Psilocine and psilocybine are the active principles of hallucinogenic mushrooms used by Mexican indians (F 3). iV,iV-Dimethyltryptamine, bufotenine and 5-methoxy-iV,iV-dimethyltryptamine are constituents of hallucinogens used in South American (F 3). 

Groger, D. Alkaloids derived from tryptophan and anthranilic acid. In Encyclopedia of Plant Physiology, New Series, Vol. 8, Secondary Plant Products (E. A. Bell, B. V. Charlwood, eds.), pp. 128-159. Springer, Berlin-Heidelberg-New York 1980 Groger, D. Alkaloids derived from tryptophan. In Biochemistry of Alkaloids (K. Mothes, H. R. 

Schiitte, M. Luckner, eds.) Deutscher Verlag der Wissenschaften, Berlin 1985 Grofie, W. Function of serotonin in seeds of walnuts. Phytochemistry 2J, 819-822 (1982) 

Tryptamine and related compounds in plants. Phytochemistry J6, 171-175 (1977) 

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Chemoselective C-alkylation of the highly acidic and enolic triacetic acid lactone 104 (pAl, = 4.94) and tetronic acid (pA, = 3.76) is possible by use of DBU[68]. No 0-alkylation takes place. The same compound 105 is obtained by the regioslective allylation of copper-protected methyl 3,5-dioxohexano-ate[69]. It is known that base-catalyzed alkylation of nitro compounds affords 0-alkylation products, and the smooth Pd-catalyzed C-allylation of nitroalkanes[38.39], nitroacetate[70], and phenylstilfonylnitromethane[71] is possible. Chemoselective C-allylation of nitroethane (106) or the nitroacetate 107 has been applied to the synthesis of the skeleton of the ergoline alkaloid 108[70]. 

Ergine, molecular formula C16H17N3O, is the amide of D-lysergic acid, and commonly known as LSA or LA-111. It is an ergoline alkaloid that occurs in various species of the Convolvulaceae, and in some species of fungus. Rivea corymbosa (ololiuqui), Argyreia nervosa (Hawaiian baby woodrose) and Ipomoea violacea (tlitliltzin) are three major sources of this alkaloid. 

Chao, J. and Der Marderosian, A.H. (1973) Identification of ergoline alkaloids in the genus Argyreia and related genera and their chemotaxonomic implications in the Convolvulaceae. Phytochemistry, 12, 2435-2440. 

The Philippine ascidian Perophora namei has yielded the polycydic alkaloid perophoramidine (30), which is the first reported metabolite from the genus Perophora [35]. A Far Eastern Eudistoma ascidian was found to contain two bromi-nated ergoline alkaloids pibocins A (31) [36] and B (32) [37]. 

Ahimsa-Miiller MA, Markert A, Hellwig S, Knoop V, Steiner U, Drewke C, Leistner E (2007) Clavicipitaceous Fungi Associated with Ergoline Alkaloid-Containing Convolvula-ceae. J Nat Prod 70 1955-1960... 

Maier, W., Schumann, B. and Groger, D. (1988) Microsomal oxygenases involved in ergoline alkaloid biosynthesis of various Claviceps strains. /. Basic Microbiol, 28, 83-93. 

Marker , A., Steffan, N., Floss, K., Hellwig, S., Steiner, U. Drewke, C., Li, S.-M., Boland, W. and Leistner, E. (2008) Biosynthesis and accumulation of ergoline alkaloids in a mutualistic association between Ipomoea asarifolia (Gonvolvulaceae) and a Clavicip-italean fungus. Plant Physiol, 147,296-305. 

Ahimsa-Miiller, M.A., Markert, A., Hellwig, S., Knoop, V., Steiner, U., Drewke, C. and Leistner E. (2007) Clavicipitaceous fungi associated with ergoline alkaloid-containing Convolvulaceae. /. Nat. Prod., 70, 1955-60. 

The Negishi reaction of oxazol-l-ylzinc chloride with 6-iodo partial ergoline alkaloid was also documented to synthesize potent S-HT. agonists [76]. 

Chao, J. and Der Maderosian, A.H. Ergoline Alkaloidal Constituents of Hawaiian Baby Wood Rose, Argyreia nervosa (Burm. f.) Bojer Journal of Pharmaceutical Sciences, (1973) 62 (4) 588-591... 

Hydrazine Hydrate University of Illinois Bulletin-, Oct. 9,1921 Hylin, J.W., Watson, D.P. Ergoline Alkaloids in Tropical Wood Roses Science (1965) 148 499-500... 

Morris, L.J. Hall, S.W. Fatty Acid Composition of Sphacelial and Sclerotial Growth Forms of Claviceps purpurea in Relation to the Production of Ergoline Alkaloids in Culture Trans. Br Mycol. Soc. (1969) 53 (3) 441-447. 

Intramolecular reactions generally give excellent results. Allylation of the nitroalkane portion of the indole 251 closes the six-membered ring of the ergoline alkaloids such as chanoclavine 253. Genet s study of various ligands revealed that BINAP provided the best results.58... 

The sclerotia contain ergoline alkaloids, mainly dihydroergosine, but also festuclavine, dihydroelymoclavine, and chanoclavine (total alkaloid 0.2-0.5%) (Frederickson et al., 1991). In cross-inoculation studies, Futrell and Webster (1966) demonstrated that conidia of C. africana from sorghum could infect Zea mays L. and Pennisetum glaucum (L.) R. Br. ( = P. typhoides (Burm.) Stapf and C. E. Hubb.), and suggested that P. glaucum could represent a source of inoculum for Sorghum. 

The reduction of ergoline alkaloid 5 can be performed in the presence of aniline as the proton source. Addition of lithium amide deprotonates the urea side chain. Under these reaction conditions, cleavage of the urea side chain is suppressed and the reduction product 6 is formed in a trims cis ratio of >95 59. 

Although Ipomoea crassicaulis has not yet been shown chemically to contain psychotropic ergoline alkaloids, extracts of leaves of this species were recendy reported to be used as an... 

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