Diarylheptanoids and a monoterpenoid from the rhizomes of Zingiber officinale: antioxidant and cytoprotective properties.
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.
Tao
Qiao Feng
QF
Department of Traditional Chinese Medicine and Natural Drug Research, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, People's Republic of China.
Xu
Yan
Y
Lam
Rosanna Y Y
RY
Schneider
Bernd
B
Dou
Hui
H
Leung
Po Sing
PS
Shi
Shu Yun
SY
Zhou
Chang Xin
CX
Yang
Lei Xiang
LX
Zhang
Rong Ping
RP
Xiao
Ye Cheng
YC
Wu
Xiumei
X
Stöckigt
Joachim
J
Zeng
Su
S
Cheng
Christopher H K
CH
Zhao
Yu
Y
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
D000972:Antineoplastic Agents, Phytogenic; D000975:Antioxidants; D036381:Diarylheptanoids; D016166:Free Radical Scavengers; D039821:Monoterpenes; D007770:L-Lactate Dehydrogenase