Wickerols A and B: novel anti-influenza virus diterpenes produced by Trichoderma atroviride FKI-3849

• Published in: Tetrahedron Vol. 68; no. 45; pp. 9267 - 9271
• Main Authors: Yamamoto, Tsuyoshi, Izumi, Naoyuki, Ui, Hideaki, Sueki, Akito, Masuma, Rokuro, Nonaka, Kenichi, Hirose, Tomoyasu, Sunazuka, Toshiaki, Nagai, Takayuki, Yamada, Haruki, Ōmura, Satoshi, Shiomi, Kazuro
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 11.11.2012; Elsevier
• Subjects: Alicyclic compounds, terpenoids, prostaglandins, steroids; Anti-influenza virus; Chemistry; Chemistry, Organic; Diterpene; Exact sciences and technology; Kinetics and mechanisms; Organic chemistry; Physical Sciences; Preparations and properties; Reactivity and mechanisms; Science & Technology; Terpenoids; Trichoderma atroviride; Wickerol; Diterpene; Wickerol; Trichoderma atroviride; Anti-influenza virus; RLFWGQVIKYIGGM-VBXVDEENSA-N; PROTON CHANNEL; Terpenoid; Trichoderma; Prediction; Carbon Isotopes; Orthomyxoviridae; Acetate; Influenzavirus; Fungi; Virus; Influenzavirus A; Cyclization; Influenza A virus; Reaction mechanism; Cations; Fungi Imperfecti; Carbon 13; Labelled compound
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2012.08.066

Wickerols A and B were produced by a fungus, Trichoderma atroviride FKI-3849. Wickerol A showed potent anti-influenza virus activity against strain A/PR/8/34 (H1N1), whereas wickerol B exhibited weaker impact. The anti-influenza virus spectrum between wickerols A and B was different. The cyclization mechanism of the wickerol carbon-skeleton was investigated by incorporation of 13C-labeled acetate. A pathway through the verticillyl cation was predicted. [Display omitted]