Caffeic Acid Oligomers with Hyaluronidase Inhibitory Activity from Clinopodium gracile

• Published in: Chemical & pharmaceutical bulletin Vol. 60; no. 4; pp. 499 - 507
• Main Authors: Aoshima, Hiroaki, Miyase, Toshio, Warashina, Tsutomu
• Format: Journal Article
• Language: English
• Published: TOKYO The Pharmaceutical Society of Japan 01.04.2012; Pharmaceutical Soc Japan; Japan Science and Technology Agency
• Subjects: caffeic acid oligomer; Caffeic Acids - chemistry; Caffeic Acids - isolation & purification; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; clinopodic acid; Clinopodium gracile; Enzyme Inhibitors - chemistry; Enzyme Inhibitors - isolation & purification; hyaluronidase inhibitor; Hyaluronoglucosaminidase - antagonists & inhibitors; Hyaluronoglucosaminidase - metabolism; Lamiaceae - chemistry; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Molecular Conformation; Pharmacology & Pharmacy; Physical Sciences; Science & Technology; Clinopodium gracile; caffeic acid oligomer; hyaluronidase inhibitor; FLAVONOID GLYCOSIDES; NEOLIGNAN; clinopodic acid; OLEANANE-TRITERPENE SAPONINS; LIVER; PARVIFLORUM; C-13 NMR; EXTRACTS; DERIVATIVES
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.60.499

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, IC50 (19 µM) among the 22 compounds isolated from this plant.