Diarylheptanoids from the Rhizomes of Curcuma kwangsiensis.
Twelve new diarylheptanoids and six known compounds were isolated from rhizomes of Curcuma kwangsiensis. Structures of the new compounds were elucidated by spectroscopic and chemical methods as (3S)- and (3R)-1,7-bis(4-hydroxyphenyl)-(6E)-6-hepten-3-ol (1a and 1b), (3S)- and (3R)-1-(3,4-dihydroxyphenyl)-7-(4-hydroxyphenyl)-(6E)-6-hepten-3-ol (2a and 2b), (3S)- and (3R)-1-(3,4-dihydroxyphenyl)-7-(4-hydroxyphenyl)heptan-3-ol (3a and 3b), (3R)-1-(3,4-dihydroxyphenyl)-7-phenyl-(6E)-6-hepten-3-ol (4b), (3S)- and (3R)-3-acetoxy-1-(3,4-dihydroxyphenyl)-7-(4-hydroxyphenyl)-(6E)-6-heptene (5a and 5b), (3S)- and (3R)-3-acetoxy-1-(3,4-dihydroxyphenyl)-7-(4-hydroxyphenyl)heptanes (6a and 6b), and (E)-1,7-bis(4-hydroxyphenyl)-6-hepten-3-one (7). The absolute configurations were determined using the modified Mosher's method. Separation of the enantiomeric mixtures (1a and 1b, 2a and 2b, 3a and 3b, 4a and 4b, 5a and 5b, 6a and 6b) was achieved on a chiral column using acetonitrile-water mixtures as eluents. The S enantiomers exhibited negative specific optical rotations in MeOH, and the R enantiomers were positive. Inhibitory effects of the compounds on nitric oxide production in lipopolysaccaride-activated macrophages were evaluated.
Li
Jun
J
Department of Natural Products Chemistry, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China.
Zhao
Feng
F
Li
Ming Zhi
MZ
Chen
Li Xia
LX
Qiu
Feng
F
D000818:Animals; D030024:Curcuma / Q000737:chemistry*; D036381:Diarylheptanoids / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D004365:Drugs, Chinese Herbal / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D008070:Lipopolysaccharides / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects; D051379:Mice; D015394:Molecular Structure; D009569:Nitric Oxide / Q000096:biosynthesis; D019906:Nuclear Magnetic Resonance, Biomolecular; D027343:Rhizome / Q000737:chemistry; D013237:Stereoisomerism
D036381:Diarylheptanoids; D004365:Drugs, Chinese Herbal; D008070:Lipopolysaccharides; D009569:Nitric Oxide