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1992 Fiscal Year Final Research Report Summary

Pharmacochemical Investigation of Marine Sponge Products

Research Project

Project/Area Number 03671000
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionOsaka University

Principal Investigator

KOBAYASHI Motomasa  Osaka University, 薬学部, 助教授 (40116033)

Co-Investigator(Kenkyū-buntansha) KITAGAWA Isao  Osaka University, 薬学部, 教授 (20028830)
Project Period (FY) 1991 – 1992
Keywordsmarine sponge / coral life / bioactive compound / marine organism / marine microorganism / antibiotic activity / cytotoxicity
Research Abstract

Due to their unusual living environment as compared with terrestrial organisms, marine organisms, such as marine sponge and octocoral, metabolite and produce a variety of substances which often have various unprecedented chemical structures and exhibit significant biological activities. In search of new pharmaceutically valuable substances from marine organisms, we have investigated the chemical constituents of marine sponges mostly inhabiting the Okinawan coral reefs.
We collected marine sponges at Kerama and Yaeyama Islands, Okinawa prefecture, in July 1991 and 1992. The lipid-soluble and water-soluble portions of these marine sponges were subjected to bioassay-guided separation, such as brine-shrimp toxicity, antifungal and cytotoxic activities. So far, we have elucidated the chemical constituents of following marine sponges.
1. Two new 3-keto-4-methylene steroids named theonellasterone and conicasterone were isolated from the marine sponge Theonella swinhoei and elucidated their absolute stereostructures. We also isolated a new dimeric steroid named bistheonellasterone together with two known 4- methylene sterols. Bistheonellasterone is a dimeric steroid biosynthesized regio- and stereospecifically by presumable intermolecular Diels-Alder cycloaddition of theonellasterone.
2. The examinations of cytotoxicity against L1210 and KB cells led to the isolation of five sesterterpenes, heteronemin, manoalide, secomanoalide, (E)-neomanoalide, and (Z) -neomanoalide, as active principles produced by the marine sponge Hyrtios erecta. Manoalide was obtained as a (ca. 1:1) mixture of 25-epimers. We have examined to reconfirm the 4R absolute configuration of these manoalide family.
3. Two new antibiotic polyacetylenes were isolated from an marine sponge Adocia sp. and their absolute stereostructures were elucidated on the basis of chemical and physicochemical evidence.

  • Research Products

    (14 results)

All Other

All Publications (14 results)

  • [Publications] I.KITAGAWA: "Biologically active tridecapeptide lactones from the Okinawan marine sponge Theonella swinhoei (Theonellidae).Structure of theonellapeptolide Id." Tetrahedron. 47. 2169-2180 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.KOBAYASHI: "Biologically active tridecapeptide lactones from the Okinawa narine sponge Theonella swinhoei (Thonellidae).Structure of theonellapeptolides Ia,Ib,Ic,and Ie." Chem.Pharm.Bull.,. 39. 1177-1184 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.DOI: "Molecular conformation of swinholide A, a potent cyto-toxic dimeric macrolide from the Okinawan marine sponge Theonella swinhoei:X-ray crystal structure of its diketone derivative." J.Org.Chem.,. 56. 3629-3632 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.KOBAYASHI: "Distribution of lanostane-type oligoglycosides in ten kinds of Okinawa sea cucumbers" Chem.Pharm.Bull.,. 39. 2282-2287 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.KOBAYASHI: "The structures of sarasinosides A1,A2,A3,B1,B2,B3,C1,C2,and C3,nine new norlanostane-triterpenoidal oligoglycosides from the Palauan marine sponge Asteropus sarasinosum." Chem.Pharm.Bull.,. 39. 2867-2877 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.IKEGAMI: "Selective inhibition of membrane fusion events in echinoderm gametes and embryos by halenaquinol sulfate." FEBS Lett.,. 302. 284-286 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.KOBAYASHI: "Two new 3-Keto-4-methylene steroids,theonellasterone and conicasterone,and a Diels-Alder type dimeric Steroid bistheonellasterone,from the Okinawan marine sponge Theonella swinhoei" Chem.Pharm.Bull.,. 40. 1773-1778 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Isao Kitagawa: "Biologically active tridecapeptide lactones from the Okinawan marine sponge Theonella swinhoei (Theonellidae). Strucutre of theonellapeptolide Id" Tetrahedron. 47. 2169-2180 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Motomasa Kobayashi: "Biologically active tridecapeptide lactones from the Okinawan marine sponge Theonella swinhoei (Theonellidae). Strucutre of theonellapeptolide Ia, Ib, Ic, and Ie" Chem. Pharm. Bull. 39. 1177-1184 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Mitsunobu Doi: "Molecular conformation of swinholide A, a potent cytotoxic dimeric macrolide from the Okinawan marine sponge Theonella swinhoei: X-ray crystal structure of its diketone derivative" J. Org. Chem. 56. 3629-3632 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Motomasa Kobayashi: "Distribution of lanostane-type oligoglycosides in ten kinds of Okinawan sea cucumbers" Chem. Pharm. Bull. 39. 2282-2287 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Motomasa Kobayashi: "The strucutres of sarasinosides A1, A2, A3, B1, B2, B3, C1, C2, and C3, nine new norlanostanetriterpenoidal oligoglycosides from the Palauan marine sponge Asteropus sarasinosum" Chem. Pharm. Bull. 39. 2867-2877 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Susumu Ikegami: "Selective inhibition of membrane fusion events in echinoderm gametes and embryos by halenaquinol sulfate" FEBS Lett. 302. 284-286 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Motomasa Kobayashi: "Two new 3-keto-4-methylene steroids, theonellasterone and conicasterone, and a Diels-Alder type dimeric steroid bistheonellasterone, from the Okinawan marine sponge Theonella swinhoei" Chem. Pharm. Bull. 40. 1773-1778 (1992)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1994-03-24  

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