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Structure determination of inonotsuoxides A and B and in vivo anti-tumor promoting activity of inotodiol from the sclerotia of Inonotus obliquus.

Abstract
Two new lanostane-type triterpenoids, inonotsuoxides A (1) and B (2) along with three known lanostane-type triterpenoids, inotodiol (3), trametenolic acid (4), and lanosterol (5), were isolated from the sclerotia of Inonotus obliquus (Pers.: Fr.) (Japanese name: Kabanoanakake) (Russian name: Chaga). Their structures were determined to be 22R,25-epoxylanost-8-ene-3beta,24S-diol (1) and 22S,25-epoxylanost-8-ene-3beta,24S-diol (2) on the basis of spectral data including single crystal X-ray analysis. These compounds except for 2 were tested for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA), as a test for potential cancer chemopreventive agents. The most abundant triterpene, inotodiol (3), was investigated for the inhibitory effect in a two-stage carcinogenesis test on mouse skin using 7,12-dimethylbenz[a]anthracene (DMBA) as an initiator and TPA as a promoter. Compound 3 was found to exhibit the potent anti-tumor promoting activity in the in vivo carcinogenesis test.
AuthorsTomoko Nakata, Takeshi Yamada, Sayaka Taji, Hirofumi Ohishi, Shun-Ichi Wada, Harukuni Tokuda, Kazuo Sakuma, Reiko Tanaka
JournalBioorganic & medicinal chemistry (Bioorg Med Chem) Vol. 15 Issue 1 Pg. 257-64 (Jan 1 2007) ISSN: 0968-0896 [Print] England
PMID17049251 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • Antigens, Viral
  • Antineoplastic Agents
  • Epstein-Barr virus early antigen
  • Plant Extracts
  • Triterpenes
  • inonotsuoxide A
  • inonotsuoxide B
  • inotodiol
  • Lanosterol
  • 9,10-Dimethyl-1,2-benzanthracene
  • Tetradecanoylphorbol Acetate
Topics
  • 9,10-Dimethyl-1,2-benzanthracene (chemistry)
  • Adenocarcinoma (drug therapy)
  • Animals
  • Antigens, Viral (drug effects, metabolism)
  • Antineoplastic Agents (chemistry, isolation & purification, pharmacology)
  • Basidiomycota (chemistry)
  • Cell Line, Tumor
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • Female
  • Lanosterol (analogs & derivatives, chemistry, pharmacology)
  • Magnetic Resonance Spectroscopy (methods, standards)
  • Mice
  • Mice, Inbred ICR
  • Models, Molecular
  • Molecular Conformation
  • Plant Extracts (chemistry, isolation & purification, pharmacology)
  • Reference Standards
  • Stereoisomerism
  • Structure-Activity Relationship
  • Tetradecanoylphorbol Acetate (chemistry, pharmacology)
  • Triterpenes (chemistry, isolation & purification, pharmacology)
  • Xenograft Model Antitumor Assays

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