DEFENSE ALLOMONES OF THE NUDIBRANCH PHYLLIDIA-VARICOSA LAMARCK 1801

被引:108
作者
HAGADONE, MR
BURRESON, BJ
SCHEUER, PJ
FINER, JS
CLARDY, J
机构
[1] IOWA STATE UNIV SCI & TECHNOL, AMES LAB, USERDA, AMES, IA 50011 USA
[2] IOWA STATE UNIV SCI & TECHNOL, AMES LAB, DEPT CHEM, AMES, IA 50011 USA
关键词
D O I
10.1002/hlca.19790620742
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The defensive secretion of the nudibranch Phyllidia varicosa consists of two isocyanosesquiterpenes: the previously described 9‐isocyanopupukeanane (1), and its 2‐isomer (4), for which we report the structure and properties. The mixture originates with a sponge, Hymeniacidon sp., where it is produced in varying proportions. CD. measurements and X‐ray diffraction data establish the absolute configuration of the two metabolites. Copyright © 1979 Verlag GmbH & Co. KGaA, Weinheim
引用
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页码:2484 / 2494
页数:11
相关论文
共 25 条
  • [1] NEW DIISOCYANIDE OF NOVEL RING STRUCTURE FROM A SPONGE
    BAKER, JT
    WELLS, RJ
    OBERHANSLI, WE
    HAWES, GB
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (13) : 4010 - 4012
  • [2] DIE REAKTION VON ISONITRILEN UND NITRILEN MIT ALKALI- UND ERDALKALIMETALLEN
    BUCHNER, W
    DUFAUX, R
    [J]. HELVETICA CHIMICA ACTA, 1966, 49 (03) : 1145 - &
  • [3] CO-OCCURRENCE OF 2 TERPENOID ISOCYANIDE-FORMAMIDE PAIRS IN A MARINE SPONGE (HALICHONDRIA-SP)
    BURRESON, BJ
    CHRISTOPHERSEN, C
    SCHEUER, PJ
    [J]. TETRAHEDRON, 1975, 31 (17) : 2015 - 2018
  • [4] 9-ISOCYANOPUPUKEANANE, A MARINE INVERTEBRATE ALLOMONE WITH A NEW SESQUITERPENE SKELETON
    BURRESON, BJ
    SCHEUER, PJ
    FINER, J
    CLARDY, J
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (16) : 4763 - 4764
  • [5] BURRESON BJ, 1974, CHEM COMMUN, P1035
  • [6] BUSING WR, 1965, ORNLTM305 USAEC REP
  • [7] ISOLATION AND STRUCTURE OF AXISONITRILE-1 AND AXISOTHIOCYANATE-1 2 UNUSUAL SESQUITERPENOIDS FROM MARINE SPONGE AXINELLA-CANNABINA
    CAFIERI, F
    FATTORUSSO, E
    MAGNO, S
    SANTACROCE, C
    SICA, D
    [J]. TETRAHEDRON, 1973, 29 (24) : 4259 - 4262
  • [8] TOTAL SYNTHESIS OF THE RACEMATE OF THE SESQUITERPENOID MARINE ALLOMONE 9-ISOCYANOPUPUKEANANE
    COREY, EJ
    BEHFOROUZ, M
    ISHIGURO, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (06) : 1608 - 1609
  • [9] AXISONITRILE-3, AXISOTHIOCYANATE-3 AND AXAMIDE-3 - SESQUITERPENES WITH A NOVEL SPIRO[4,5]DECANE SKELETON FROM SPONGE AXINELLA-CANNABINA
    DIBLASIO, B
    FATTORUSSO, E
    MAGNO, S
    MAYOL, L
    PEDONE, C
    SANTACROCE, C
    SICA, D
    [J]. TETRAHEDRON, 1976, 32 (04) : 473 - 478
  • [10] ISOLATION AND STRUCTURE OF AXISONITRILE-2 - NEW SESQUITERPENOID IISONITRILE FROM SPONGE AXINELLA-CANNABINA
    FATTORUSSO, E
    MAGNO, S
    MAYOL, L
    SANTACROCE, C
    SICA, D
    [J]. TETRAHEDRON, 1974, 30 (21) : 3911 - 3913