Crotalaria species

CO2H 0 Isolated from Pisum and Crotalaria species Isowlllardine - no known bloactivlty 13... 

A phytochemical study of Crotalaria species has revealed the presence of 1-methylenepyrrolizidine (68) in four new species, namely C. grandistipulata Harms, C. lachnophora A. Rich, C. natalitia Meissner, and C. stolzii (Baker fil.) Milne-Redh. ex Polhill.38 The necine (69) is probably present in C. cylindrocarpa DC and C. podocarpa DC.38... 

Two outbreaks of human liver disease in India have been attributed to the consumption of plants containing pyrrolizidine alkaloids. In the first instance, the disease was caused by eating cereals contaminated with seeds of a Crotalaria species.56 Haemodynamic studies were carried out on eight patients suffering from the characteristic veno-occlusive disease. In the second study, two cases of sudden liver failure that are believed to be due to the ingestion of herbal concoctions made from seeds and plants of Heliotropium species are reviewed.57... 

Crotalaria species are used as preplant cover crops, intercrops, or soil amendments. When used as cover crops, Crotalaria spp. reduces plant-parasitic nematode populations by i) acting as a nonhost or a poor host, ii) producing allelochemicals that are toxic or inhibitory, iii) providing a niche for antagonistic flora and fauna, and iv) trapping the nematode. 

The presence of pyrrolizidine alkaloids in arctiid moths that had been reared on Senecio and Crotalaria species has been established by Rothschild et al.4S These alkaloids are stored in the moths, and serve as a deterrent to vertebrate predators and as precursors for insect sex pheromones. A pyrrolizidine alkaloid metabolite from the Cinnabar moth (Tyria jacobaea L.), named callimorphine, has been shown to have the structure (49) on the basis of mass-spectral and degradative evidence.46 The structure (49) was confirmed by synthesis of callimorphine and a diastereo-isomer by treatment of 9-chlororetronecine with the sodium salt of ( )-2-acetoxy-2-methylbutanoic acid. 

Crotalaria species (rattlebox) Cyamopsis tetragonoloba (cluster bean)... 

Rattlebox Crotalaria species Van Rompay M, Kessler RC. Trends in alternative medi- ... 

The occurrence of the free bases in the plants of the Crotalaria species, reported by Culvenor and his collaborators, is of interest and is fully reported. The alkaloids which do not fall within this general category but contain the pyrrolizidine ring are only briefly referred to here. 

Several useful reviews and compilations of data on pyrrolizidine alkaloids have been published. These include a review of all aspects of pyrrolizidine alkaloid chemistry and biochemistry this is comprehensive, but rather idiosyncratic in its balance (sixteen pages are devoted to the synthesis of necines and necic acids whereas physical and spectroscopic properties of the alkaloids are discussed in barely two.) Nevertheless, this up-to-date work will certainly be of great interest and usefulness to workers in the field. Klasek has surveyed the investigations on pyrrolizidine alkaloids carried out at Olomouc, and Atal and Sawhney have produced a useful compilation of data on alkaloids from Indian Crotalaria species. Pyrrolizidine alkaloids from the Orchidaceae have been surveyed by Luning" and by Brandange. Pyrrolizidine alkaloids are included in a comprehensive compilation of data on alkaloids isolated from plants occurring in the U.S.S.R. ... 

Crotalaria sagittalis-. The roots of this fabaceous plant were considered to be avery strong narcotic by the Delaware-Okl Indians (lantaquic eon 1942). Dangerous hepatotoxic pyrrolizidine alkaloids are known from Crotalaria species, and their ingestion should thus be avoided assiduously (Turner Szczawinski 1991). 

The identity of crotalaburnine, from Crotalaria laburnifolia, with anacrotine, from the same and several other Crotalaria species, has been apparent for some time, but it has only recently been formally established by direct comparison. ... 

Johnson, A.E., R.J. Molyneux, and G.B. Merrill. 1985. Chemistry of toxic range plants. Variation in pyrrolizidine alkaloid content of Senecio, Amsinckia, and Crotalaria species. /. Agric. Food Chem. 33 (l) 50-55. 

CigHjjNOs, Mr 351.40, mp. 217°C (207-208°C), [alg -62.4° (CHCI3), [a]o -17.6° (CjHjOH). R. is a pyrrolizidine alkaloid from Asteraceae (Senecio, Erechtites) and some Crotalaria species (Fabaceae). It exists in the plants as the A(-oxide and is highly toxic, causing liver and kidney cancer (see pyrrolizidine alkaloids). 

Human health problems have been attributed to the accidental consumption of plant materials that contain pyrrolizidine alkaloids (Beier and Nigg, 1992). The consumption of wheat containing seeds of Heliotropium popovii has caused a large outbreak of veno-occlusive disease in Afghanistan. The main alkaloid present was heliotrine (15). In India, similar problems have occurred with Crotalaria species. 

A variety of pyrrolizidine alkaloids and their N-oxides have antitumor activity (Wink, 1993b). Herbal material of Senecio vulgaris (Asteraceae) has been used for hundreds of years as a treatment for cancer. The active compounds have been shown to be senecionine (5) and senecionine N-oxide. Indicine N-oxide (16) from Heliotropium indicum (Boraginaceae) has pronounced antitumor activity. Mono-crotaline (8), from several Crotalaria species (Fabaceae), has similar activity (Blasko and Cordell, 1988 Suffness and Cordell, 1985). Alkylation seems to be involved in the antitumor activity. As the A -oxides cannot serve as enamines and hence cannot be directly involved in alkylation, these compounds should only be active to the extent they are converted to the free bases. At least in the case of indicine iV-oxide (16), this does not appear to be the case (Suffness and Cordell, 1985). 

With dicarboxyclic acids, the double esterification leads to macrocyclic diesters which can occur as 11-13-nienibered ring systems. A typical example for an 11-membered PA is monocrotaline, the main PA occurring in crotalaria species, or crispatme. Most of the PAs show a 12-membered ring system this can be found, for example, in senecionine or senkirkine, both contained in many senecio species. A typical 13-member ring is demonstrated in the PAs doronenine (also isolated from senecio) and in madurensine (from crotalaria). Very rare is the 14-member macrocycle It is found in the PA parsonsine (from parson ja-species) this structure is possible on account of a further ester group within the necic add chain. It is interesting to mention that until now in all cases of macrocyclic diester PAs only the 7-B-OH isomer (mainly retronecine) is described and not the a-isomer (heliotridine) (Fig. 13.3). 

Robins et al. (246) demonstrated that L-threonine and L-isoleucine are specific precursors for monocrotalic acid (46), the C -necic acid component of monocrotaline (44), present in several Crotalaria species. Degradation of the monocrotalic acid produced gave results which were consistent with the incorporation of isoleucine into C-1, C-2, C-3, C-6, and C-7 of monocrotalic acid (Scheme 25). The remaining three carbon atoms may be derived from propionate. 

PiLBEAM, D. J., R. M. PoLHiLL, and E. A. Bell Free Amino Acids and Alkaloids of South American, Asian and Australian Crotalaria species. Bot. J. Linn. Soc. 79, 259 (1979). 

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