2. Academic Validation
  3. Conjugates of 3α-methoxyserrat-14-en-21β-ol (PJ-1) and 3β-methoxyserrat-14-en-21β-ol (PJ-2) as cancer chemopreventive agents

Conjugates of 3α-methoxyserrat-14-en-21β-ol (PJ-1) and 3β-methoxyserrat-14-en-21β-ol (PJ-2) as cancer chemopreventive agents

  • Eur J Med Chem. 2011 Aug;46(8):3368-75. doi: 10.1016/j.ejmech.2011.04.062.
Reiko Tanaka 1,  Hiroko Tsujii,  Takeshi Yamada,  Tetsuya Kajimoto,  Harukuni Tokuda,  Takanari Arai,  Nobutaka Suzuki,  Junya Hasegawa,  Yoshio Hamashima,  Manabu Node
Affiliations

Affiliation

  • 1 Laboratory of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. tanakar@gly.oups.ac.jp
PMID: 21620532 DOI: 10.1016/j.ejmech.2011.04.062
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.

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