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).
School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, PR China; Key Laboratory of Structure Based Drug Design and Discovery (Shenyang Pharmaceutical University), Ministry of Education, Wenhua Road 103, Shenyang 110016, PR China.
Wenli
W
Wang
School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, PR China; Key Laboratory of Structure Based Drug Design and Discovery (Shenyang Pharmaceutical University), Ministry of Education, Wenhua Road 103, Shenyang 110016, PR China. Electronic address: liningsypharm@163.com.
Ning
N
Li
Key Laboratory of Structure Based Drug Design and Discovery (Shenyang Pharmaceutical University), Ministry of Education, Wenhua Road 103, Shenyang 110016, PR China; School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, PR China.
Jian
J
Wang
School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, PR China; Key Laboratory of Structure Based Drug Design and Discovery (Shenyang Pharmaceutical University), Ministry of Education, Wenhua Road 103, Shenyang 110016, PR China.
Gang
G
Chen
Pharmaceutical College, Guangxi Medical University, Nanning, Guangxi 530021, PR China.
Renbin
R
Huang
School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, PR China; Key Laboratory of Structure Based Drug Design and Discovery (Shenyang Pharmaceutical University), Ministry of Education, Wenhua Road 103, Shenyang 110016, PR China.
Weihong
W
Zhao
School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, PR China; Key Laboratory of Structure Based Drug Design and Discovery (Shenyang Pharmaceutical University), Ministry of Education, Wenhua Road 103, Shenyang 110016, PR China.
Jiayuan
J
Li
School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, PR China; Key Laboratory of Structure Based Drug Design and Discovery (Shenyang Pharmaceutical University), Ministry of Education, Wenhua Road 103, Shenyang 110016, PR China.
Yingying
Y
Si
D016588:Anticarcinogenic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001572:Benzofurans / Q000032:analysis / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D047188:Chalcones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006027:Glycosides / Q000032:analysis; D006801:Humans; D008519:Medicine, Traditional; D033641:Millettia / Q000737:chemistry*; D015394:Molecular Structure; D016660:NAD(P)H Dehydrogenase (Quinone) / Q000037:antagonists & inhibitors*; D018515:Plant Leaves / Q000737:chemistry; D018517:Plant Roots / Q000737:chemistry
D016588:Anticarcinogenic Agents; D001572:Benzofurans; D047188:Chalcones; D006027:Glycosides; D016660:NAD(P)H Dehydrogenase (Quinone); C447479:NQO1 protein, human
Chalcanes; Chemopreventive agents; Leguminosae; Millettia pulchra (Benth) kurz var-laxior (Dunn) Z.Wei; NQO1 inducing activity