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

Phytochemistry. 2016 Nov:131:107-114. doi: 10.1016/j.phytochem.2016.09.005. Epub 2016 Sep 20.

Abstract

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).

Keywords: Chalcanes; Chemopreventive agents; Leguminosae; Millettia pulchra (Benth) kurz var-laxior (Dunn) Z.Wei; NQO1 inducing activity.

MeSH terms

  • Anticarcinogenic Agents / chemistry
  • Anticarcinogenic Agents / isolation & purification*
  • Anticarcinogenic Agents / pharmacology*
  • Benzofurans / analysis
  • Benzofurans / chemistry
  • Benzofurans / isolation & purification*
  • Benzofurans / pharmacology*
  • Chalcones / chemistry
  • Chalcones / isolation & purification*
  • Chalcones / pharmacology*
  • Glycosides / analysis
  • Humans
  • Medicine, Traditional
  • Millettia / chemistry*
  • Molecular Structure
  • NAD(P)H Dehydrogenase (Quinone) / antagonists & inhibitors*
  • Plant Leaves / chemistry
  • Plant Roots / chemistry

Substances

  • Anticarcinogenic Agents
  • Benzofurans
  • Chalcones
  • Glycosides
  • NAD(P)H Dehydrogenase (Quinone)
  • NQO1 protein, human