Absolute stereostructures of three new sesquiterpenes from the fruit of Alpinia oxyphylla with inhibitory effects on nitric oxide production and degranulation in RBL-2H3 cells.
The 80% aqueous acetone extract and the ethyl acetate-soluble portion from the dried fruit of Alpinia oxyphylla MIQUEL were found to show inhibitory effects on nitric oxide production in lipopolysaccharide-activated macrophages and antigen-induced degranulation in RBL-2H3 cells. A new eudesmane-type sesquiterpene, oxyphyllol A, and two eremophilane-type sesquiterpenes, oxyphyllols B and C, were isolated from the ethyl acetate-soluble portion, together with 16 known constituents. The absolute stereostructures of oxyphyllols A, B, and C were determined on the basis of chemical and physicochemical evidence. The effects of isolated components on nitric oxide production were examined, and nine constituents including oxyphyllol A and nootkatone were found to show inhibitory activity. On the other hand, five constituents inhibited the release of beta-hexosaminidase from RBL-2H3 cells.
Morikawa
Toshio
T
Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan.
Matsuda
Hisashi
H
Toguchida
Iwao
I
Ueda
Kazuho
K
Yoshikawa
Masayuki
M
D032429:Alpinia / Q000737:chemistry*; D000818:Animals; D015550:Cell Degranulation / Q000187:drug effects*; D002460:Cell Line; D008297:Male; D051379:Mice; D009569:Nitric Oxide / Q000096:biosynthesis*; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D013057:Spectrum Analysis; D013237:Stereoisomerism; D001619:beta-N-Acetylhexosaminidases / Q000378:metabolism
D012717:Sesquiterpenes; D009569:Nitric Oxide; D001619:beta-N-Acetylhexosaminidases