Bioactive constituents of Chinese natural medicines. VII. Inhibitors of degranulation in RBL-2H3 cells and absolute stereostructures of three new diarylheptanoid glycosides from the bark of Myrica rubra.
Three new diarylheptanoid glycosides, named (+)-S-myricanol 5-0-beta-D-glucopyranoside, myricanene A 5-O-alpha-L-arabinofuranosyl(1-->6)-beta-D-glucopyranoside, and myricanene B 5-0-alpha-L-arabinofuranosyl(1-->6)-beta-D-glucopyranoside, were isolated from the bark of Chinese Myrica rubra, together with twenty known compounds. The absolute stereostructures of the new diarylheptanoid glycosides were elucidated on the basis of chemical and physicochemical evidence, including the application of the modified Mosher's method. The inhibitory effects of isolated constituents on the release of beta-hexosaminidase from RBL-2H3 cells were examined, and several diarylheptanoids, myricanol, (+)-S-myricanol, myricanone, and myricanenes A and B, and a flavonol, myricetin, were found to show the inhibitory activity.
Matsuda
Hisashi
H
Kyoto Pharmaceutical University, Japan.
Morikawa
Toshio
T
Tao
Jing
J
Ueda
Kazuho
K
Yoshikawa
Masayuki
M
D000818:Animals; D015550:Cell Degranulation / Q000187:drug effects*; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000494:pharmacology; D006027:Glycosides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D015471:Leukemia, Basophilic, Acute / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D051381:Rats; D014407:Tumor Cells, Cultured; D001619:beta-N-Acetylhexosaminidases / Q000037:antagonists & inhibitors*
D004791:Enzyme Inhibitors; D006027:Glycosides; D001619:beta-N-Acetylhexosaminidases