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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
Project Status Completed (Fiscal Year 1992)
Budget Amount *help
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1992: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 1991: ¥1,300,000 (Direct Cost: ¥1,300,000)
Keywordsmarine sponge / coral life / bioactive compound / marine organism / marine microorganism / antibiotic activity / cytotoxicity / サンゴ礁生物 / 生物活性物質 / ポリアセチレン / ポリケチド / Theonella swinhoei / ステロイドニ量体 / テオネラステロン / ビステオネラステロン
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.

Report

(3 results)
  • 1992 Annual Research Report   Final Research Report Summary
  • 1991 Annual Research Report
  • Research Products

    (25 results)

All Other

All Publications (25 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
    • Related Report
      1992 Final Research Report Summary
  • [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
    • Related Report
      1992 Final Research Report Summary
  • [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
    • Related Report
      1992 Final Research Report Summary
  • [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
    • Related Report
      1992 Final Research Report Summary
  • [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
    • Related Report
      1992 Final Research Report Summary
  • [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
    • Related Report
      1992 Final Research Report Summary
  • [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
    • Related Report
      1992 Final Research Report Summary
  • [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
    • Related Report
      1992 Final Research Report Summary
  • [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
    • Related Report
      1992 Final Research Report Summary
  • [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
    • Related Report
      1992 Final Research Report Summary
  • [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
    • Related Report
      1992 Final Research Report Summary
  • [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
    • Related Report
      1992 Final Research Report Summary
  • [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
    • Related Report
      1992 Final Research Report Summary
  • [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
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M.Kobayashi: "Heterosigma-glycolipids I,II,III,and IV,four diacyl-glyceroglycolipids possessing w3-polyunsaturated fatty acid residues,from the raphidophycean dinoflagellate Heterosiqma akashiwo" Chem.Pharm.Bull.,. 40. 1404-1410 (1992)

    • Related Report
      1992 Annual Research Report
  • [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)

    • Related Report
      1992 Annual Research Report
  • [Publications] M.Kobayashi: "サンゴ礁生物由来の抗腫瘍活性物質" BIOmedica. 7. 37-42 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Isao Kitagawa: "Marine Natural Products XXV.Biologically Active Tridecapeptide Lactones from the Okinawan Marine sponge Theonella Swinhoei(Theonellidae).Structure of Theonellapeptolide Id" Tetrahedron. 47. 2169-2180 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Motomasa Kobayashi: "Marine Natural Products XXVI.Biologically Active Tridecapeptide Lactones from the Okinawan Marine Sponge Theonella swinhoei(Theonellidae).Structures of Theonellapeptolides Ia,Ib,Ic,and Ie" Chem.Pharm.Bull.,. 39. 1177-1184 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Mitsunobu Doi: "Molecular Conformation of Swinholide A,a Potent Cytotoxic Dimeric Macrolide from the OKinawan Marine Sponge Theonella swinhoei:Xーray Crystal Structure of Its Diketone Derivative" J.Org.Chem.,. 56. 3629-3632 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Motomasa Kobayashi: "Marine Natural Products XXVII.Distribution of LanostaneーType Oligoglycosides in Ten Kinds of OKinawan Sea Cucumbers" Chem.Pharm.Bull.,. 39. 2282-2287 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Motomasa Kobayashi: "Marine Natural Products XXVIII.The Structures of Sarasinosides A_1,A_2,A_3,B_1,B_2,B_3,C_1,C_2,and C_3,Nine New NorlanostaneーTriterpenoidal Oligoglycosides from the Palauan Marine Sponge Asteropus sarasinosum" Chem.Pharm.Bull.,. 39. 2867-2877 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Motomasa Kobayashi: "Marine Natural Products XXIX.Heterosigmaーglycolipids I,II,III,and IV,Four Diacylglyceroglycolipids Possessing ω3ーPolyunsaturated Fatty Acid Residues,from the Raphidoーphycean Dinoflagellate Heterosigma akashiwo" Chem.Pharm.Bull.,. 40. (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] Motomasa Kobayashi: "Marine Natural Productx XXX.Two New 3ーKetoー4ーmethylene Steroids,Theonellasterone and Conicasterone,and a DielsーAlder Type Dimeric Steroid Bistheonellasterone,from the Okinawan Marine Sponge The one lla Swinhoei" Chem.Pharm.Bull. 40. (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] 北川 勲: "海洋生物を起源とする制癌剤の探索" 有機合成化学協会誌, 9 (1991)

    • Related Report
      1991 Annual Research Report

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Published: 1991-04-01   Modified: 2016-04-21  

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