Two novel stilbene-2-carboxylic acid phytoalexins from Cajanus cajan

Cooksey, Christopher J.; Dahiya, Jagroop S.; Garratt, Peter J.; Strange, Richard

doi:10.1016/0031-9422(80)85072-2

Cited by 69 publications

(43 citation statements)

References 17 publications

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“…Quercetin-3-methyl ether (3) has a more restricted distribution and occurs mainly in the leaves, leaf resin, and flowers of the Compositae, Cistaceae, Cyperaceae, and Cactaceae (Harborne et al, 1999). The stilbene (4) has previously been reported only from the leaf surfaces of Cajanus cajan that had been challenged with the fungus, Botrytis cinerea (Cooksey et al, 1982). However, we found that the pod surfaces produced this compound in the apparent absence of fungal infection.…”

Section: Discussioncontrasting

confidence: 47%

“…Their relative locations were determined from long-range 1 H-13 C correlations in HMBC data (Table 1) − , consistent with the loss of CO 2 . UV, NMR, and MS data allowed the structure of 4 to be confirmed as 3-hydroxy-4-prenyl-5-methoxystilbene-2-carboxylic acid (C 21 H 22 O 4 ), a phytoalexin reported previously from leaves of Cajanus cajan challenged with Botrytis cinerea (Cooksey et al, 1982).…”

Section: Identification Of Compounds From Pod Surface Of Pigeonpea (Imentioning

confidence: 59%

“…Overall, data showed that the absolute amounts of stilbene (4) and its concentration relative to other phenolic compounds, especially quercetin-3-methyl ether (3), in pigeonpea genotypes could influence predation by larvae of H. armigera. Thus, there is a potential for using cultivars that produce high proportions of stilbene, relative to the other phenolics, in selective breeding programs for developing pigeonpea genotypes that are both less susceptible to fungal infection (Cooksey et al, 1982) and more resistant to pod-borers.…”

Section: Discussionmentioning

confidence: 99%

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Stevenson

Simmonds

et al. 2003

Journal of Chemical Ecology

102

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Abstract-A methanol extract of the pod surfaces of Cajanus cajan, a feeding stimulant for fifth-instar Helicoverpa armigera, was shown to contain four main phenolic compounds. Three of these were identified as isoquercitrin, quercetin, and quercetin-3-methyl ether, by comparing UV spectra and HPLC retention times with authentic standards. The fourth compound was isolated by semipreparative HPLC and determined to be 3-hydroxy-4-prenyl-5-methoxystilbene-2-carboxylic acid (stilbene) by NMR spectroscopy and mass spectrometry. Quercetin, isoquercitrin, and quercetin-3-methyl did not affect the selection-behavior of fifth-instar H. armigera. However, larvae were deterred from feeding on glass-fiber disks impregnated with the stilbene. Furthermore, larvae exposed to quercetin-3-methyl ether consumed significant amounts of both disks. In a binary-choice bioassay, a combination of quercetin-3-methyl ether and the stilbene on one disk and pure quercetin-3-methyl ether on the other disk resulted in increased consumption of both glass-fiber disks by larvae. In contrast, consumption was reduced if the combination was presented to larvae on one disk with purified stilbene on the other disk. Cajanus cajan cultivars that varied in their susceptibility to H. armigera were surveyed for the presence of the four phenolic compounds. An absence of quercetin and higher concentrations of isoquercitrin than the cultivated variety characterized pod surface extracts of pod-borer-resistant cultivars. In addition, the ratio of the stilbene to quercetin-3-methyl ether was greater in the pod-borer-resistant cultivars. These findings * To whom correspondence should be addressed. E-mail. p.stevenson@kew.org

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Section: Discussioncontrasting

confidence: 47%

Section: Identification Of Compounds From Pod Surface Of Pigeonpea (Imentioning

confidence: 59%

Section: Discussionmentioning

confidence: 99%

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Green

Stevenson

Simmonds

et al. 2003

Journal of Chemical Ecology

102

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“…(Bhanumati et al, 1979;Cooksey et al, 1982;Duker-Eshun et al, 2004). The defined active ingredients in the WECML and the mechanism of the effects of them on the osteogenic and adipogenic differentiation of BMSCs and the adipogenic trans-differentiation of OBs remains to be further studied.…”

Section: Discussionmentioning

confidence: 99%

Effects of water extract ofCajanus cajanleaves on the osteogenic and adipogenic differentiation of mouse primary bone marrow stromal cells and the adipocytic trans-differentiation of mouse primary osteoblasts

Zhang¹,

Liu²,

Sun³

et al. 2009

Pharmaceutical Biology

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“…], which belongs to the Cajanus genus, one of the most valuable perennial or annual leguminous food crops in Asia, Africa and some parts of tropical and subtropical areas of the world, has been reported to contain stilbenoids, flavonoids, coumarin, and other kinds of constituents [2 -7], yet the number of reported compounds is quite small. Our interest in the bioactivities of stilbenoids and the attempt to enrich the chemical constituents in pigeon pea led to the isolation of two new stilbenoids, cajanotone (1) and cajanamide A (2), six known ones (3)(4)(5)(6)(7)(8) and four known dihydroflavones (9)(10)(11)(12) (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Two New Stilbenoids from Cajanus cajan

Zhang

Zhu

Huang

et al. 2012

Zeitschrift Für Naturforschung B

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Two new stilbenoids cajanotone and cajanamide A (1-2), together with another six known ones (3-8) and four known dihydroflavones (9-12), have been isolated from the leaves of Cajanus cajan. Their structures were elucidated based on spectroscopic studies. A possible pathway to the new compounds 1 and 2 has been proposed. In vitro cytotoxicities of selected compounds against cancer cell lines HepG2, MCF-7 and A549 have been evaluated. Compounds 7 and 8 show strong cytotoxity against all the tested cell lines (with IC 50 values in the range of 3.5 -6.0 µ M), and compounds 1 and 3 showed strong to moderate activity against the three cell lines.

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Two novel stilbene-2-carboxylic acid phytoalexins from Cajanus cajan

Cited by 69 publications

References 17 publications

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Effects of water extract ofCajanus cajanleaves on the osteogenic and adipogenic differentiation of mouse primary bone marrow stromal cells and the adipocytic trans-differentiation of mouse primary osteoblasts

Two New Stilbenoids from Cajanus cajan

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