Caffeoyl Derivatives and Flavonoids from Three Compositae Species

Four flavones; chrysoeriol (1), apigenin (3), luteolin (6), orientin (11), and three flavanones; naringenin (2), eriodictyol (4) and 3',4',5,5',7-pentahydroxy flavanone (5), five flavonols; rhamnetin (13), hyperoside (15), rhamnetin-3-O-β-D-glucoside (17), mearnsitin-3-O-β-D-glucoside (19) and isoquercitrin (20), an aurone; 3',4',5',6-tetrahydroxyaurone-4-O-glucoside (bractein] (7), six caffeoyl derivatives of quinic acid; 3,4-dicaffeoylquinic acid-methyl ester (8), 3,5-dicaffeoylquinic acid-methyl ester (9), 3,5-dicaffeoylquinic acid (10), neochlorogenic acid (12), 1,4,5-tricaffeoylquinic acid (14) and 1,5-dicaffeoylquinic acid (16) and caffeic acid (18) were isolated from the flowers and the remaining aerial parts of Helichrysum bracteatum (Vent.) Andrews, Gazania nivea DC. and Dimorphotheca ecklonis DC. Compounds 8 and 9 were isolated for the first time from genus Helichrysum, compounds 10 and 12 from H. bracteatum, compounds 12-17 from genus Gazania, compounds 10, 12, 18 and 20 from genus Dimorphotheca and compound 19 from genus Dimorphotheca and family Compositae. The anti-inflammatory, analgesic and antipyretic effects of the flowers and the remaining aerial parts of the three studied plants as well as the major isolated compounds of the most potent extract were studied. Bractein (7) was the most potent anti-inflammatory and antipyretic, while 3,5-dicaffeoylquinic acid (10) was the most potent analgesic. The flowers of the three plants showed a significant hepatoprotective effect.