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Isolation of Hennaminal and Isolation and Total Synthesis of Hennamide, Pyrrolinone Compounds from the Marine Cyanobacterium Rivularia sp.
Takahashi, Hiroki; Iwasaki, Arihiro; Ebihara, Akira; Taguchi, Raimu; Jeelani, Ghulam; Nozaki, Tomoyoshi; Suenaga, Kiyotake.
Affiliation
  • Takahashi H; Department of Chemistry, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan.
  • Iwasaki A; Department of Chemistry, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan.
  • Ebihara A; Department of Chemistry, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan.
  • Taguchi R; Department of Chemistry, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan.
  • Jeelani G; Department of Biomedical Chemistry, Graduate School of Medicine, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
  • Nozaki T; Department of Biomedical Chemistry, Graduate School of Medicine, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
  • Suenaga K; Department of Chemistry, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan.
Org Lett ; 25(14): 2400-2404, 2023 04 14.
Article in En | MEDLINE | ID: mdl-37011050
Two new natural products were isolated from the marine cyanobacterium Rivularia sp. collected in Japan. Hennaminal possesses a very rare functional group, ß,ß-diamino unsaturated ketone, which has only been found in bohemamine-type natural products so far. Hennamide possesses a reactive N-acyl pyrrolinone moiety, which induces self-dimerization. The isolation and structure determination supported by computational chemistry and total synthesis, as well as the antitrypanosomal activities of hennaminal and hennamide are described.
Subject(s)

Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Biological Products / Cyanobacteria Language: En Journal: Org Lett Journal subject: BIOQUIMICA Year: 2023 Document type: Article Affiliation country: Japan Country of publication: United States

Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Biological Products / Cyanobacteria Language: En Journal: Org Lett Journal subject: BIOQUIMICA Year: 2023 Document type: Article Affiliation country: Japan Country of publication: United States