Bioactive benzofuran-chalcanes as potential NQO1 inducers from Millettia pulchra (Benth) kurzvar-laxior (Dunn) Z.Wei.

Five chalcanes (( α ′ R )-2, α ′-dimethoxy-furano-[4″, 5′′: 3′, 4′] chalcane, ( α ′ R , βR )-2′, α ′, β -trimethoxy-furano-[4″, 5′′: 3′, 4′] chalcane, ( α ′ S , βR )-2′, α ′, β -trimethoxy-furano-[4″, 5′′: 3′, 4′] chalcane, ( α ′ R , βR )-2′, β -dimethoxy- α ′-hydroxyethoxy-furano-[4″, 5′′: 3′, 4′] chalcane, ( α ′ S , βR )-2′, β -dimethoxy- α ′-hydroxyethoxy-furano-[4″, 5′′: 3′, 4′] chalcane) and a flavonoid glycoside (3′, 7-dihydroxy-6-methoxy-4′, 5′-methylenedioxyisoflavone 6-O- β -D- glucopyranoside), together with 15 known components, were isolated from the leaves of Millettia pulchra (Benth) Kurzvar-laxior (Dunn) Z. Wei, a traditional Zhuang medicine. Their chemical structures were established by extensive analysis of NMR, mass spectrometry and ECD spectra. Furthermore compounds ( α ′ R , βR )-2′, β -dimethoxy- α ′-hydroxyethoxy-furano-[4″, 5′′: 3′, 4′] chalcane, ( α ′ S , βR )-2′, β -dimethoxy- α ′-hydroxyethoxy-furano-[4″, 5′′: 3′, 4′] chalcane, quercetin, methyl 2-O- β -D-glucopyranosylbenzoate, 6,7-dimethoxy-3′,4′-methylenedioxyisoflavone and lyoniresinol were suggested to be potential chemopreventive agents because of their significant activity in inducing NQO1 ([NAD(P)H quinine oxidoreductase 1], a phase II metabolism enzyme). [ABSTRACT FROM AUTHOR]