Chemical constituents from the leaves of Hydrangea macrophylla var. thunbergii (III): Absolute stereostructures of hydramacrosides A and B, secoiridoid glucoside complexes with inhibitory activity on histamine release.
Following the characterization of dihydroisocoumarin constituents, two secoiridoid glucoside complexes, called hydramacrosides A and B, were isolated from the leaves of Hydrangea macrophylla Seringe var. thunbergii Makino. The absolute stereostructures of hydramacrosides A and B were elucidated on the basis of chemical and physicochemical evidence, which included the application of the 13C-NMR glycosylation shift rule of 1,1'-disaccharides and the modified Mosher's method. Hydramacrosides A and B exhibited an inhibitory effect on histamine release from rat mast cells induced by an antigen-antibody reaction.
Matsuda
H
H
Kyoto Pharmaceutical University, Japan.
Shimoda
H
H
Uemura
T
T
Ueda
T
T
Yamahara
J
J
Yoshikawa
M
M
D000107:Acetylation; D000818:Animals; D000937:Antigen-Antibody Reactions / Q000187:drug effects; D005122:Exudates and Transudates / Q000166:cytology / Q000187:drug effects / Q000378:metabolism; D005960:Glucosides / Q000737:chemistry / Q000494:pharmacology*; D006633:Histamine Antagonists / Q000737:chemistry / Q000494:pharmacology*; D006868:Hydrolysis; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D008407:Mast Cells / Q000187:drug effects / Q000378:metabolism; D008968:Molecular Conformation; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry / Q000494:pharmacology*; D051381:Rats
D005960:Glucosides; D006633:Histamine Antagonists; D011714:Pyrans; C407016:hydramacroside A; C407017:hydramacroside B