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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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9,10-Dimethyl-1,2-benzanthracene / chemistry
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Adenocarcinoma / drug therapy*
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Animals
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Antigens, Viral / drug effects
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Antigens, Viral / metabolism
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Antineoplastic Agents / chemistry*
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Antineoplastic Agents / isolation & purification
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Antineoplastic Agents / pharmacology
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Basidiomycota / chemistry*
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Cell Line, Tumor
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Crystallography, X-Ray
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Drug Screening Assays, Antitumor
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Female
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Lanosterol / analogs & derivatives*
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Lanosterol / chemistry
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Lanosterol / pharmacology
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Magnetic Resonance Spectroscopy / methods
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Magnetic Resonance Spectroscopy / standards
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Mice
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Mice, Inbred ICR
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Models, Molecular
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Molecular Conformation
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Plant Extracts / chemistry
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Plant Extracts / isolation & purification
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Plant Extracts / pharmacology
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Reference Standards
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Stereoisomerism
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Structure-Activity Relationship
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Tetradecanoylphorbol Acetate / chemistry
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Tetradecanoylphorbol Acetate / pharmacology
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Triterpenes / chemistry*
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Triterpenes / isolation & purification
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Triterpenes / pharmacology
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Xenograft Model Antitumor Assays
Substances
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Antigens, Viral
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Antineoplastic Agents
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Epstein-Barr virus early antigen
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Plant Extracts
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Triterpenes
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inonotsuoxide A
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inonotsuoxide B
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inotodiol
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Lanosterol
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9,10-Dimethyl-1,2-benzanthracene
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Tetradecanoylphorbol Acetate