7a-O-Methyldeguelol

Abstract

The title compound, (6,7‐dimeth­oxy‐3,4‐dihydro‐2H‐chromen‐4‐yl)(5‐meth­oxy‐2,2‐dimeth­yl‐2H‐chromen‐6‐yl)­meth­an­one, C24H25O6, is a modified rotenoid. In the crystal structure, the chromene ring is disordered, together with its attached methyl and methoxy groups. The mol­ecules are packed as layers parallel to the ac plane. These layers are inter­connected through C—H⋯O inter­actions to form a three‐dimensional network.

Isoflavonoids of the Leguminosae

“…128 Acetone extracts of the roots of Derris trifoliata gave 7a-O-methyldeguelol (78) as a minor component, 129 for which the crystal structure was later obtained. 130 Although characterised by an open C-ring structure, 78 is probably derived from deguelin, which also occurs in this species. 127,129 Yenesew et al have proposed the name 'rotenoloid' to describe this subclass of modified rotenoids, 129 a further example of which, 7a-O-methylelliptonol (79), was isolated from stem extracts of Derris trifoliata.…”

“…154 The A-ring structure of these coumaronochromone derivatives is identical, while that of the B-rings indicates a possible biogenetic sequence from triquetrumone A (128) to C (130). Triquetrumone C (130) was also active in an estrogen receptor binding assay. Triquetrumone C (130) was also active in an estrogen receptor binding assay.…”

“…73 Xiang et al isolated triquetrumones A-C (128-130) from an ethanolic extract of the whole plant of Tadehagi triquetrum. 154 The A-ring structure of these coumaronochromone derivatives is identical, while that of the B-rings indicates a possible biogenetic sequence from triquetrumone A (128) to C (130). Both the original extract and triquetrumones A-C (128-130) possess moderate anthelmintic activity.…”

“…This uncommon group of isoflavonoids is represented by five new examples (127)(128)(129)(130)(131) from the 2005-2007 period. Bioassayguided fractionation of 95% EtOH extracts of the aerial parts of Flemingia macrophylla using an amyloid b-protein-induced neurotoxicity blocking assay gave flemingichromone (127) and the isoflavone fleminginin (21).…”

“…If confirmed, the presence of coumestans in Cylicodiscus gabunensis is of taxonomic interest, since this species belongs to subfamily Mimosoideae of the Leguminosae, in which isoflavonoids are almost unknown. 4 This uncommon group of isoflavonoids is represented by five new examples (127)(128)(129)(130)(131) from the 2005-2007 period. Bioassayguided fractionation of 95% EtOH extracts of the aerial parts of Flemingia macrophylla using an amyloid b-protein-induced neurotoxicity blocking assay gave flemingichromone (127) and the isoflavone fleminginin (21).…”