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.

• Authors: Tomoko Nakata, Takeshi Yamada, Sayaka Taji, Hirofumi Ohishi, Shun-Ichi Wada, Harukuni Tokuda, Kazuo Sakuma, Reiko Tanaka
• Journal: Bioorganic & medicinal chemistry (Bioorg Med Chem) Vol. 15 Issue 1 Pg. 257-64 (Jan 01 2007) ISSN: 0968-0896 [Print] England
• PMID: 17049251 (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