title: Conjugates of 3α-methoxyserrat-14-en-21β-ol (PJ-1) and 3β-methoxyserrat-14-en-21β-ol (PJ-2) as cancer chemopreventive agents.
abstract: 3α-Methoxyserrat-14-en-21β-ol (PJ-1) and 3β-methoxyserrat-14-en-21β-ol (PJ-2) were conjugated with well-known phenolic compounds, narigenin, hesperetin, genistein, and daidzein (1-8). Other conjugates of PJ-2-3,5-dihydroxy-4-methoxybenzoic acid (9), PJ-2-pyrogallol (10), and derivatives of PJ-1, PJ-2-3,3-dimethyl-succinates (11, 12), PJ-1, PJ-2-succinates (13, 14), PJ-2-glycine (15), PJ-2-piperidine acetic acid (16), and PJ-1 epoxy-3,3-dimethyl-succinate (17) 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 effects of 11 (IC(50) = 251), 12 (IC(50) = 248), and 17 (IC(50) = 230 mol ratio/32 pmol/TPA), were 2-fold stronger than those of the other compounds such as oleanolic acid (IC(50) = 449). Compounds 10, 11, and 17 inhibited mouse skin tumor promotion in an in vivo two-stage carcinogenesis model. The in vivo two-stage mouse-skin carcinogenesis test employed 7,12-dimethylbenz[a]anthracene (DMBA) as an initiator and TPA as a promoter.
authors.affiliation: Laboratory of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. tanakar@gly.oups.ac.jp
authors.forename: Reiko
authors.initials: R
authors.lastname: Tanaka
authors.forename: Hiroko
authors.initials: H
authors.lastname: Tsujii
authors.forename: Takeshi
authors.initials: T
authors.lastname: Yamada
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Kajimoto
authors.forename: Harukuni
authors.initials: H
authors.lastname: Tokuda
authors.forename: Takanari
authors.initials: T
authors.lastname: Arai
authors.forename: Nobutaka
authors.initials: N
authors.lastname: Suzuki
authors.forename: Junya
authors.initials: J
authors.lastname: Hasegawa
authors.forename: Yoshio
authors.initials: Y
authors.lastname: Hamashima
authors.forename: Manabu
authors.initials: M
authors.lastname: Node
mesh_terms: D015127:9,10-Dimethyl-1,2-benzanthracene / Q000009:adverse effects; D000818:Animals; D016588:Anticarcinogenic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000956:Antigens, Viral / Q000096:biosynthesis*; D015197:Carcinogenicity Tests; D002471:Cell Transformation, Neoplastic / Q000187:drug effects*; D020031:Epstein-Barr Virus Infections / Q000821:virology*; D044950:Flavanones / Q000737:chemistry; D019833:Genistein / Q000737:chemistry; D004854:Herpesvirus 4, Human / Q000187:drug effects* / Q000502:physiology; D006569:Hesperidin / Q000737:chemistry; D007529:Isoflavones / Q000737:chemistry; D051379:Mice; D009828:Oleanolic Acid / Q000494:pharmacology; D012878:Skin Neoplasms / Q000139:chemically induced / Q000517:prevention & control*; D013755:Tetradecanoylphorbol Acetate / Q000009:adverse effects; D014315:Triterpenes / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: C492953:3beta-methoxyserrat-14-en-21beta-ol; D016588:Anticarcinogenic Agents; D000956:Antigens, Viral; C033305:Epstein-Barr virus early antigen; D044950:Flavanones; D007529:Isoflavones; D014315:Triterpenes; D015127:9,10-Dimethyl-1,2-benzanthracene; C004742:daidzein; D009828:Oleanolic Acid; D019833:Genistein; D006569:Hesperidin; C005273:naringenin; D013755:Tetradecanoylphorbol Acetate; C013015:hesperetin