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Eudesmane‐Type Sesquiterpenes from Curcuma phaeocaulis and Their Inhibitory Activities on Nitric Oxide Production in RAW 264.7 Cells
Author(s) -
Liu Yue,
Ma Jianghao,
Wang Ying,
Donkor Paul Owusu,
Li Qin,
Gao Suyu,
Hou Yaguang,
Xu Yang,
Cui Jianing,
Ding Liqin,
Zhao Feng,
Kang Ning,
Chen Lixia,
Qiu Feng
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402465
Subject(s) - sesquiterpene , chemistry , rhizome , zingiberaceae , stereochemistry , two dimensional nuclear magnetic resonance spectroscopy , terpene , nitric oxide , curcuma , inhibitory postsynaptic potential , terpenoid , organic chemistry , botany , biology , neuroscience
Eight eudesmane‐type sesquiterpenes – phaeusmanes A–H ( 1 – 8 ) – isolated for the first time in this work, and four others ( 9 – 12 ) isolated for the first time from plants in this work, together with fourteen known eudesmane derivatives, were isolated from the rhizomes of Curcuma phaeocaulis . Their structures were elucidated by 1D and 2D NMR and CD spectroscopy and HRMS. Compound 8 is the first example of a nitrogen‐containing eudesmane‐type sesquiterpene isolated from the genus Curcuma . Furthermore, inhibitory effects of the isolated compounds on NO production in lipopolysaccharide‐activated macrophages were evaluated. Compounds 1 , 6 , 10 , 19 , 22 , and 24 showed strong inhibitory activities on NO production with IC 50 values of 3.2, 4.8, 1.2, 0.8, 3.8, and 0.8 μ M , respectively. Preliminary structure–activity relationships for these compounds are proposed. A possible biogenetic pathway for nitrogen‐containing eudesmane‐type sesquiterpene 8 is postulated.