title: Potential anti-tumor-promoting activity of 3alpha-hydroxy-D:A-friedooleanan-2-one from the stem bark of Mallotus philippensis.
abstract: Four known friedelane-type triterpenoids, friedelin ( 1), 3-hydroxy-D:A-friedoolean-3-en-2-one ( 2), 2beta-hydroxy-D:A-friedooleanan-3-one ( 3), and 3alpha-hydroxy-D:A-friedooleanan-2-one ( 4), and two known lupane-type triterpenoids, lupeol ( 5) and betulin ( 6), were isolated from the stem bark of Mallotus philippensis. Isolates 1 - 4 and their synthetic analogues, 3-acetoxy-D:A-friedoolean-3-en-2-one ( 2A) and 3alpha-acetoxy-D:A-friedooleanan-2-one ( 4A), were tested for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by 12- O-tetradecanoylphorbol 13-acetate (TPA). The inhibitory effect of compounds 2 (IC (50) = 292 mol ratio/32 pmol/TPA) and 4 (IC (50) = 288) was stronger than those of the other compounds tested and the positive control, curcumin (IC (50) = 343). Compound 4 strongly inhibited mouse skin tumor promotion in an IN VIVO two-stage carcinogenesis model. Studies have been conducted to identify the biologically active compounds extracted from the leaves, bark, and cones of trees that currently have no specific commercial use and are therefore treated as waste in the forestry industry.
authors.affiliation: Department of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, Takatsuki, Osaka, Japan. tanakar@gly.oups.ac.jp
authors.forename: Reiko
authors.initials: R
authors.lastname: Tanaka
authors.forename: Tomoko
authors.initials: T
authors.lastname: Nakata
authors.forename: Chiharu
authors.initials: C
authors.lastname: Yamaguchi
authors.forename: Shun-Ichi
authors.initials: S
authors.lastname: Wada
authors.forename: Takeshi
authors.initials: T
authors.lastname: Yamada
authors.forename: Harukuni
authors.initials: H
authors.lastname: Tokuda
mesh_terms: D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000494:pharmacology*; D002460:Cell Line; D005260:Female; D004854:Herpesvirus 4, Human; D006801:Humans; D036461:Mallotus Plant / Q000737:chemistry*; D051379:Mice; D008813:Mice, Inbred ICR; D015394:Molecular Structure; D009374:Neoplasms, Experimental / Q000188:drug therapy; D024301:Plant Bark / Q000737:chemistry*; D018547:Plant Stems; D013047:Specific Pathogen-Free Organisms; D014315:Triterpenes / Q000737:chemistry* / Q000494:pharmacology*; D014775:Virus Activation / Q000187:drug effects
chemical_list: C532561:3alpha-hydroxy-D-A-friedooleanan-2-one; D000972:Antineoplastic Agents, Phytogenic; D014315:Triterpenes