Complex C-glycosyl flavonoid phytoalexins from Cucumis sativus.
Extraction of cucumber leaf tissue expressing induced resistance against powdery mildew fungi revealed the presence of two new major C-glycosyl flavonoid products: vitexin-6-(4-hydroxy-1-ethylbenzene) (cucumerin A, 1) and isovitexin-8-(4-hydroxy-1-ethylbenzene) (cucumerin B, 2). In addition, the known C-glycosyl flavonoids apigenin-8-C-beta-D-glucopyranoside (vitexin, 3), apigenin-6-C-beta-D-glucopyranoside (isovitexin, 4), luteolin-8-C-beta-D-glucopyranoside (orientin, 5), and luteolin-6-C-beta-D-glucopyranoside (isoorientin, 6), as well as 4-hydroxycinnamic acid (p-coumaric acid, 7) and its methyl ester (p-came, 8), were found in higher quantities within resistant plants. The structures of 1-8 were elucidated using spectroscopic methods and unambiguously confirmed for 3-8 using co-chromatography experiments with authentic standards. On the basis of the results of this study and the reported biological activities of C-glycosyl flavonoids, these compounds would play a vital role in the defense strategy of this species by acting as phytoalexins.
D018553:Cucumis sativus / Q000737:chemistry*; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005658:Fungi / Q000187:drug effects; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008350:Manitoba; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D012717:Sesquiterpenes; D013237:Stereoisomerism; D013729:Terpenes; D000094162:Phytoalexins
D005419:Flavonoids; D006027:Glycosides; D010936:Plant Extracts; D012717:Sesquiterpenes; D013729:Terpenes; D000094162:Phytoalexins