Cypellocarpins A-C, phenol glycosides esterified with oleuropeic acid, from Eucalyptus cypellocarpa.
Three new phenol glycosides acylated with (+)-oleuropeic acid, cypellocarpins A (1), B (2), and C (3), along with seven known compounds, were isolated from the dried leaves of Eucalyptus cypellocarpa. Structures of the new compounds were determined on the basis of spectroscopic methods, including 2D NMR experiments and chemical degradation. These new compounds and a known related glucoside (7) showed potent in vitro antitumor-promoting activity in a short-term bioassay evaluating the inhibitory effect on Epstein-Barr virus early antigen activation induced by 12-O-tetradecanoyl phorbol 13-acetate (TPA). These compounds also suppressed an in vivo two-stage carcinogenesis induced with nitric oxide and TPA on mouse skin.
Ito
H
H
Faculty of Pharmaceutical Sciences, Okayama University, Tsushima, Okayama 700-8530, Japan.
Koreishi
M
M
Tokuda
H
H
Nishino
H
H
Yoshida
T
T
D000818:Animals; D016588:Anticarcinogenic Agents / Q000737:chemistry / Q000302:isolation & purification*; D002460:Cell Line; D003509:Cyclohexanecarboxylic Acids / Q000737:chemistry*; D004951:Esterification; D005052:Eucalyptus / Q000737:chemistry*; D005260:Female; D005960:Glucosides / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification*; D004854:Herpesvirus 4, Human / Q000187:drug effects; D006801:Humans; D051379:Mice; D010212:Papilloma / Q000139:chemically induced / Q000517:prevention & control; D010946:Plants, Medicinal; D012878:Skin Neoplasms / Q000139:chemically induced / Q000517:prevention & control; D013057:Spectrum Analysis; D014775:Virus Activation / Q000187:drug effects
D016588:Anticarcinogenic Agents; D003509:Cyclohexanecarboxylic Acids; D005960:Glucosides; D006027:Glycosides; C417927:cypellocarpin A; C417928:cypellocarpin B; C417929:cypellocarpin C; C417926:oleuropeic acid