title: Diarylheptanoids and a monoterpenoid from the rhizomes of Zingiber officinale: antioxidant and cytoprotective properties.
abstract: Three new diarylheptanoids and one new monoterpenoid were isolated from the rhizomes of Zingiber officinale together with four known diarylheptanoids, 5-8. Their structures were elucidated mainly by spectroscopic methods, and they were deduced as 5-[4-hydroxy-6-(4-hydroxyphenethyl)tetrahydro-2 H-pyran-2-yl]-3-methoxybenzene-1,2-diol (1), sodium (E)-7-hydroxy-1,7-bis(4-hydroxyphenyl)hept-5-ene-3 S-sulfonate (2), sodium (E)-7-hydroxy-1,7-bis(4-hydroxyphenyl)hept-5-ene-3 R-sulfonate (3), and hydroxycineole-10-O-beta-D-glucopyranoside (4), respectively. Among the isolated compounds, compounds 1, 5, and 8 exhibited strong superoxide anion radical scavenging activities in a phenazine methosulfate-NADH system. In a more biological system, these compounds were demonstrated to exhibit potent protection against lipid peroxidation in mouse liver microsomes exposed to oxidative conditions. These compounds were subsequently tested on primary cultures of rat hepatocytes exposed to oxidative damage, and definitive cytoprotective actions were found.
authors.affiliation: Department of Traditional Chinese Medicine and Natural Drug Research, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, People's Republic of China.
authors.forename: Qiao Feng
authors.initials: QF
authors.lastname: Tao
authors.forename: Yan
authors.initials: Y
authors.lastname: Xu
authors.forename: Rosanna Y Y
authors.initials: RY
authors.lastname: Lam
authors.forename: Bernd
authors.initials: B
authors.lastname: Schneider
authors.forename: Hui
authors.initials: H
authors.lastname: Dou
authors.forename: Po Sing
authors.initials: PS
authors.lastname: Leung
authors.forename: Shu Yun
authors.initials: SY
authors.lastname: Shi
authors.forename: Chang Xin
authors.initials: CX
authors.lastname: Zhou
authors.forename: Lei Xiang
authors.initials: LX
authors.lastname: Yang
authors.forename: Rong Ping
authors.initials: RP
authors.lastname: Zhang
authors.forename: Ye Cheng
authors.initials: YC
authors.lastname: Xiao
authors.forename: Xiumei
authors.initials: X
authors.lastname: Wu
authors.forename: Joachim
authors.initials: J
authors.lastname: Stöckigt
authors.forename: Su
authors.initials: S
authors.lastname: Zeng
authors.forename: Christopher H K
authors.initials: CH
authors.lastname: Cheng
authors.forename: Yu
authors.initials: Y
authors.lastname: Zhao
mesh_terms: D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D036381:Diarylheptanoids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D016166:Free Radical Scavengers / Q000494:pharmacology; D020939:Zingiber officinale / Q000737:chemistry*; D022781:Hepatocytes / Q000187:drug effects; D007770:L-Lactate Dehydrogenase / Q000378:metabolism; D008297:Male; D051379:Mice; D008862:Microsomes, Liver / Q000187:drug effects; D015394:Molecular Structure; D039821:Monoterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D019906:Nuclear Magnetic Resonance, Biomolecular; D051381:Rats; D017207:Rats, Sprague-Dawley; D027343:Rhizome / Q000737:chemistry
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D000975:Antioxidants; D036381:Diarylheptanoids; D016166:Free Radical Scavengers; D039821:Monoterpenes; D007770:L-Lactate Dehydrogenase