title: Caffeic acid oligomers with hyaluronidase inhibitory activity from Clinopodium gracile.
abstract: Eight new caffeic acid oligomers, clinopodic acids J-Q (1-8), were isolated from whole plants of Clinopodium gracile, together with nine known caffeic acid oligomers. The caffeic acid oligomers with two to four dihydrobenzofuran rings were isolated as natural products for the first time. Clinopodic acid M (4) showed the strongest hyaluronidase inhibitory activity, IC(50) (19 µM) among the 22 compounds isolated from this plant.
authors.affiliation: School of Pharmaceutical Sciences, University of Shizuoka, 52–1 Yada, Suruga-ku, Shizuoka, Japan.
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Aoshima
authors.forename: Toshio
authors.initials: T
authors.lastname: Miyase
authors.forename: Tsutomu
authors.initials: T
authors.lastname: Warashina
mesh_terms: D002109:Caffeic Acids / Q000737:chemistry* / Q000302:isolation & purification; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000302:isolation & purification; D006821:Hyaluronoglucosaminidase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D019686:Lamiaceae / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation
chemical_list: D002109:Caffeic Acids; D004791:Enzyme Inhibitors; D006821:Hyaluronoglucosaminidase; C040048:caffeic acid