Leguminosae, alkaloids

It has become customary to call the principal members of this group the lupin alkaloids, but in view of their wide distribution in the Papilionaceae, a better title is that suggested above, since they appear to be the characteristic alkaloids of this leguminous sub-family. This is not the only type of alkaloid found in the Leguminosae other types occur, e.g., in Acacia (p. 631), Crotalaria (p. 601), Erythrina (p. 386), Mimosa (p. 4) and Pentaclethra (p. 776). 

We knew Utetheisa to feed on poisonous plants as a larva (Figure 1B). The plants, of the genus Crotalaria (family Leguminosae), were known to contain pyrrolizidine alkaloids (henceforth abbreviated as PAs), intensely bitter compounds potently hepatotoxic to mammals (7). Other species of Utetheisa were known to sequester PAs (8). We found this to be true for U. ornatrix as well. Adult Utetheisa raised on Crotalaria spectabilis, one of the principal foodplants available to the moth in the United States, contain on average about 700 p,g of monocrotaline (1), the principal PA in that plant (9, 10). 

Kinghom, A.D. and Balandrin, M.F. (1984). Quinolizidine alkaloids of the Leguminosae Structural types, analysis, chemotaxonomy and biological activities, in Pelletier, S.W., Ed., Alkaloids chemical and biological perspectives, John Wiley and Sons, New York, pp. 105-148. 

Lobeline (3), extracted from Lobelia inflate, interacts with the nicotinic receptor and could also be exploited to influence cholinergic function in AD. Other alkaloids such as sophoramine (4) and cytisine (5), found in members of the Leguminosae, also have nicotinic agonistic properties. ... 

Quinolizidine alkaloids (QA) are thought to be typical natural products of many Leguminosae (1-3) but a few isolated occurrences have been reported also in unrelated families, e.g. Chenopodiaceae ( 1 ), Berberidaceae ( ), Papaveraceae ( ), Scrophulariaceae ( ), Santalaceae ( ), Solanaceae ( ), and Ranunculaceae (J ). These observations could indicate that the genes for QA biosynthesis are probably not restricted to the Leguminosae but are widely distributed in the plant kingdom however, they are only rarely expressed in the other families. We could support this belief by recent experiments using plant cell suspension cultures. A short-term and transientQA formation could be detected after induction even in "QA-free" species, such as Daucus, Spinacia, Conium, and Symphytum (6). 

Szentesi, A. and Wink, M. 1991. Fate of quinolizidine alkaloids through three trophic levels Laburnum anagyroides (Leguminosae) and associated organisms. Journal of Chemical Ecology, 17 1557-1573. 

Quinolizidine alkaloids (lupine alkaloids) occur in the family Leguminosae, especially the subfamily Papilionaceae. They are also found in some species of other families such as Chenopodiaceae, Berberidaceae, Papaveraceae, Nymphaeaceae, Ranunculaceae, Scrophulariaceae, Solanaceae, Compositae, Rubiaceae, Monimiaceae, Ericaceae, and Adociidae. 

Pyrrolizidine (1) and its derivatives have attracted the attention of chemists during the last two or three decades because this bicyclic system occurs in a number of alkaloids from various families of Compositae, Boraginaceae, Leguminosae, etc. Structural analysis of these substances, study of their reactions, and attempted syntheses have afforded considerable information concerning the chemistry of this class of compounds. Although the field has been covered by a... 

Erythrina alkaloids, possessing curare-like activity, are a large class of natural products found in Erythrina plants (Leguminosae). In a study towards construction of the erythrina skeleton, disfavored 5-endo-trig cyclizations were achieved by Ikeda et al. by BusSnH-mediated radical cyclization of an //-vinylic a-chloroacetamide to give five-membered lactams... 

Pyrrolizidine alkaloids have a wide distribution, but are characteristic of certain genera of the Boraginaceae (e.g. Heliotropium, Cynoglossum, and Symphytum), the Compositae/Asteraceae (e.g. Senecio) and the Leguminosae/Fabaceae (e.g. Crotalaria). The pyrrolizidine bases rarely occur in the free form, but are generally found as esters with rare mono- or di-basic acids, the necic acids. Thus, senecionine (Figure 6.18) from Senecio species is a diester of retronecine with senecic acid. Inspection of the ten-carbon skeleton... 

Quinolizidine alkaloids are mainly found in plants of the Leguminosae/Fabaceae family. They deter or repel feeding of herbivores, and are toxic to them by a variety of mechanisms. A number of plants (Laburnum, Cytisus, Lupinus) containing significant quantities of these alkaloids must be regarded as potentially toxic to humans, and are known to be responsible for human poisoning. 

There are now over 60 Erythrina alkaloids of known structure 1-61 (see Figs. 2-4) and several more, the structures of which are yet to be assigned (12). The alkaloids occur in species of Erythrina (Leguminosae), a genus of wide distribution in tropical parts of the world, and in species of Cocculus... 

Demonstrating unambiguously that alkaloids are solely responsible for the deterrency of plants to an herbivore has been difficult to establish except in selected instances. This has been possible by examining several species of Lupinus (Leguminosae) that synthesize quinolizidine alkaloids (QAs) which may be... 

Wink, M. 1984. Chemical defence of Leguminosae. Are quinolizidine alkaloids part of the antimicrobial defence system of lupins Z. Naturforsch. 39c, 548-552... 

Other isolation studies are summarized in Table l 2-7 five new alkaloids have been obtained this year. Cell suspension cultures of Baptisia australis, Lupinus polyphyllus, and Sarothamnus scoparius produce lower yields of alkaloids than the differentiated plants, with lupanine as the main component8 (cj Vol. 11, p. 63). Examination of the leaf alkaloids of B. australis by g.l.c. and by g.l.c.-m.s. resulted in the identification of eleven constituents, including two new alkaloids.2 The structures and the distribution of some quinolizidine alkaloids that may be used as systematic markers in the Leguminosae have now been supplemented by more recent data.9... 

Lupines are known as rich leguminosae in lipids and proteins. This makes them very interesting if they were produced in a large industrial scale. However the presence of bitter and poisonous quinolizidine alkaloids is the main obstacle to overcome for a broader utilisation. 

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