Isolation and identification of Cicer isoflavonoids

doi:10.1016/0305-1978(81)90030-2

Biochemical Systematics and Ecology

Volume 9, Issues 2–3, 10 November 1981, Pages 125-128

https://doi.org/10.1016/0305-1978(81)90030-2 Get rights and content

Abstract

Medicarpin and maackiain have been obtained as phytoalexins from the fungus-inoculated stems of 15 Cicer species. These compounds co-occur with the constitutive isoflavones, formononetin and biochanin A. In the stem tissues of C. cuneatum, formononetin and biochanin A are accompanied by small quantities of a third constitutive isoflavone identified as 7-hydroxy-2′-methoxy-4′,5′-methylenedioxyisoflavone (cuneatin) by comparison with synthetic material. The taxonomic relationships between Cicer and genera of the tribes Trifolieae and Vicieae are briefly discussed.

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The chemistry of the genus Cicer L.
2006, Studies in Natural Products Chemistry
The genus Cicer L. consists of 43 species of annual and perennial herbs in the monogeneric tribe Cicereae (Leguminosae). The genus affords considerable interest because C. arietinum, the most well studied and most vulnerable species to disease and pests, is the chickpea, an important crop and food for resource-poor farmers, especially in Asia. More than 200 natural products have been identified from the genus. This chapter describes the chemistry of Cicer and the function of those compounds with known biological activities especially in the context of micro-organisms and insects that are natural pests and diseases of the cultivated crop. Some compounds occur constitutively in healthy chickpea plants that present inbuilt defence to infection by a range of pathogens and insects. For example, although the pterocarpans, maackiain and medicarpin occur constitutively they also increase in concentration when the plant is attacked by a fungus, nematode or bacterium. These induced compounds (phytoalexins) are either biosynthesised de novo or as recent work suggests are accessible from glycosides stored in vacuoles. While these phytoalexins occur in all species of Cicer a few produce a wide array of isoflavonoids including recently discovered compounds from the rare isoflav-3-ene and arylbenzofuran classes all of which show varying degrees of biological activity against pathogens of chickpea and all are inducible. The chemical ecology of the plant especially with relevance to agricultural applications is discussed. We also describe their distinct occurrence among Cicer species and indicate how knowledge about their biosynthesis can inform the taxonomy of the genus. The recent synthesis of the arylbenzofuran cicerfuran from novel stilbenes precursors has been achieved along with several analogues. Their importance beyond the defensive value to the plant has become apparent through biological activity testing against different micro-organisms and shows that these compounds may provide valuable novel activity against bacteria, fungi and protozoans. The chapter will also discuss some aspects of chemical synthesis of flavonoids of structural relevance to Cicer L.
Efficient production and capture of 8-prenylnaringenin and leachianone G - Biosynthetic intermediates of sophoraflavanone G - By the addition of cork tissue to cell suspension cultures of Sophora flavescens
2003, Phytochemistry
It has previously been demonstrated that the addition of cork tissue to cell suspension cultures of Sophora flavescens stimulates the production of sophoraflavanone G, most of which has been recovered from the added cork tissue. In the present study, it was found that two precursors of sophoraflavanone G, 8-prenylnaringenin (sophoraflavanone B) and leachianone G, both of which have never been detected either in cultured cells or in the original plants, also accumulated in the added cork tissue. Thirteen minor flavonoids including three prenylated flavonoids, in addition to 8-prenylnaringenin and leachianone G, were isolated from the cork tissue co-incubated with S. flavescens cells. The new compounds flavescenones A, B and C, were determined to be (3R)-5, 7, 2′-trihydroxy-6-γ, γ-dimethylallyl-4′, 5′-methylenedioxyisoflavanone; 5, 7, 2′-trihydroxy-6-γ, γ-dimethylallyl-4′, 5′-methylenedioxyisoflavone and 2-[2′,4′-dihydroxy-3′-(γ-hydroxymethyl-γ-methylallyl)phenyl]-5,6-methylenedioxybenzofuran, respectively, by means of spectroscopic analyses that included 2D-NMR techniques.
The distribution of isoflavonoids in Cicer
1998, Phytochemistry
Fifteen annual and perennial species of Cicer have been analysed for the presence of isoflavonoids. The pterocarpans medicarpin and maackiain and the isoflavonoids biochanin A and formononetin were present in the roots of all species and also occurred widely as glucosides or malonylated glucosides. Five recently identified isoflav-3-enes and a 2-arylbenzofuran were detected exclusively in three species, C. bijugum, C. judaicum and C. pinnatifidum, and their occurrence was restricted to the roots. Conversely, 9-O-methylcoumestrol was recorded in all species except for C. bijugum, C. judaicum and C. pinnatifidum. These species have been placed previously in series Cicer, a taxonomic grouping of 6 species within section Cicer of subgenus Cicer. The present results indicate that they should be considered as taxonomically distinct from other species in this series, a proposal supported by a number of other recent studies.
Isoflavenes from the roots of Cicer judaicum
1996, Phytochemistry
Three new isoflav-3-enes, 7-hydroxy-2′-methoxy-4′,5′-methylenedioxyisoflav-3-ene (judaicin), judaicin 7-O-glucoside and judaicin 7-O-(6″-O-malonylglucoside), have been isolated from the roots of Cicer judaicum together with the known pterocarpans, maackiain 3-O-glucoside and maackiain 3-O-(6′-O-malonylglucoside). Their structures were determined using 1D and 2D NMR techniques in conjunction with other physical methods of analysis. The malonylglucoside derivatives were found to decarboxylate in solution to give the corresponding acetylglucosides.
The flavonoids of the genus Lathyrus and a comparison of flavonoid patterns within the tribe vicieae
1993, Biochemical Systematics and Ecology
A leaf survey of Lathyrus showed that the flavonols kaempferol and quercetin were present in 36 of 38 species representing nine sections of the genus. Six glycosides of each flavonol were characterised. Kaempferol 3-sophoroside-7-glucoside, previously reported in L. vernus, was found in four further species. Other distinctive glycosidic patterns in the genus include the 3-robinobioside, the 3-sophoroside and the 3-lathyroside-7-rhamnoside. The two species surveyed in section Pratensis were different from all the others, in having flavones as well as flavonols and, additionally, in having proanthocyanidins. These differences in leaf flavonoid patterns also extended to the flowers, pods and seeds. Isoflavone accumulation was confirmed in L. montanus but otherwise the genus was depauperate in isoflavones. A comparison of patterns found in Lathyrus with those of Cicer, Lens, Pisum and Vicia indicate that each genus has a distinctive flavonoid profile.
Cytogenetics and Related Aspects in Some Pulse Crops
1991, Developments in Plant Genetics and Breeding

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Isolation and identification of Cicer isoflavonoids

Abstract

Phytochemistry

Phytochemistry

Phytochemistry

Phytochemistry

Biochem. Syst. Ecol.

Biochem. Syst. Ecol.

Phytochemistry

Phytochemistry

Phytochemistry

J. Chromatogr.

Phytochemistry

Ph.D. thesis