title: Antiallergic phenanthrenes and stilbenes from the tubers of Gymnadenia conopsea.
abstract: The methanolic extract from the tubers of Gymnadenia conopsea showed an antiallergic effect on ear passive cutaneous anaphylaxis reactions in mice. From the methanolic extract, three new dihydrophenanthrenes, gymconopins A ( 1), B ( 2), and C ( 3), and a new dihydrostilbene, gymconopin D ( 4), were isolated together with 10 known phenanthrene and stilbene constituents. The structures of the new compounds were determined on the basis of physicochemical evidence. Next, the inhibitory effects of the principal constituents on the release of beta-hexosaminidase, as a marker of degranulation, in RBL-2H3 cells were examined and five phenanthrenes, gymconopin B ( 2), 4-methoxy-9,10-dihydrophenanthrene-2,7-diol ( 6), 1-(4-hydroxybenzyl)-4-methoxyphenanthrene-2,7-diol ( 7), 1-(4-hydroxybenzyl)-4-methoxy-9,10-dihydrophenanthrene-2,7-diol ( 8), and blestriarene A ( 9), and six dihydrostilbenes, gymconopin D ( 4), batatacin III ( 10), 3'- O-methylbatatacin III ( 11), 3,3'-dihydroxy-2-(4-hydroxybenzyl)-5-methoxybibenzyl ( 12), 3',5-dihydroxy-2-(4-hydroxybenzyl)-3-methoxybibenzyl ( 13), and 3,3'-dihydroxy-2,6-bis(4-hydroxybenzyl)-5-methoxybibenzyl ( 14) were found to inhibit the antigen-induced degranulation by 65.5 to 99.4 % at 100 microM in RBL-2H3 cells.
authors.affiliation: Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan.
authors.forename: Hisashi
authors.initials: H
authors.lastname: Matsuda
authors.forename: Toshio
authors.initials: T
authors.lastname: Morikawa
authors.forename: Haihui
authors.initials: H
authors.lastname: Xie
authors.forename: Masayuki
authors.initials: M
authors.lastname: Yoshikawa
mesh_terms: D000818:Animals; D018926:Anti-Allergic Agents / Q000008:administration & dosage / Q000494:pharmacology* / Q000627:therapeutic use; D004305:Dose-Response Relationship, Drug; D008297:Male; D051379:Mice; D008815:Mice, Inbred Strains; D029595:Orchidaceae; D010323:Passive Cutaneous Anaphylaxis; D010616:Phenanthrenes / Q000008:administration & dosage / Q000494:pharmacology / Q000627:therapeutic use; D008517:Phytotherapy; D010936:Plant Extracts / Q000008:administration & dosage / Q000494:pharmacology* / Q000627:therapeutic use; D013267:Stilbenes / Q000008:administration & dosage / Q000494:pharmacology / Q000627:therapeutic use; D001619:beta-N-Acetylhexosaminidases / Q000037:antagonists & inhibitors / Q000187:drug effects
chemical_list: D018926:Anti-Allergic Agents; D010616:Phenanthrenes; D010936:Plant Extracts; D013267:Stilbenes; D001619:beta-N-Acetylhexosaminidases