CYLINDRICINE-A AND CYLINDRICINE-B, NOVEL ALKALOIDS FROM THE ASCIDIAN CLAVELINA-CYLINDRICA

被引:132
作者
BLACKMAN, AJ [1 ]
LI, CP [1 ]
HOCKLESS, DCR [1 ]
SKELTON, BW [1 ]
WHITE, AH [1 ]
机构
[1] UNIV WESTERN AUSTRALIA,DEPT CHEM,NEDLANDS,WA 6009,AUSTRALIA
关键词
D O I
10.1016/S0040-4020(01)96270-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The ascidian Clavelina cylindrica, which was collected in Tasmania, has yielded two novel alkaloids, cylindricine A, rel-(3R,4R,5S,7aR,11aR)-3-chloromethyl-5-hexyl-perhydro-pyrrolo-[2,1-j]quinolin-7-one, (12), and cylindricine B. rel-(3S,5R,6S,8aR,12aR)-3-chloro-6-hexyl-perhydropyrido[2,1-j]quinoline-8-one, (13). Cylindricine B is the first example of the new pyrido-[2,1-j]-quinoline ring system while cylindricine A is the first pyrrolo[2,1-j]quinoline known from nature. Single crystal X-ray studies support the assignment of the two alkaloids.
引用
收藏
页码:8645 / 8656
页数:12
相关论文
共 9 条
  • [1] WAKAYIN - A NOVEL CYTOTOXIC PYRROLOIMINOQUINONE ALKALOID FROM THE ASCIDIAN CLAVELINA SPECIES
    COPP, BR
    IRELAND, CM
    BARROWS, LR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (15) : 4596 - 4597
  • [2] EICHER T, 1986, SYNTHESIS-STUTTGART, P908
  • [3] FAULKNER DJ, 1991, NAT PROD REP, V8, P927
  • [4] HALL SR, 1990, XTAL 3 REFERENCE MAN
  • [5] PICTAMINE, A QUINOLIZIDINE ALKALOID FROM THE TUNICATE CLAVELINA-PICTA
    KONG, FH
    FAULKNER, DJ
    [J]. TETRAHEDRON LETTERS, 1991, 32 (30) : 3667 - 3668
  • [6] BRINE SHRIMP - A CONVENIENT GENERAL BIOASSAY FOR ACTIVE-PLANT CONSTITUENTS
    MEYER, BN
    FERRIGNI, NR
    PUTNAM, JE
    JACOBSEN, LB
    NICHOLS, DE
    MCLAUGHLIN, JL
    [J]. PLANTA MEDICA, 1982, 45 (01) : 31 - 34
  • [7] CLAVEPICTINE-A AND CLAVEPICTINE-B - CYTOTOXIC QUINOLIZIDINES FROM THE TUNICATE CLAVELINA-PICTA
    RAUB, MF
    CARDELLINA, JH
    CHOUDHARY, MI
    NI, CZ
    CLARDY, J
    ALLEY, MC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (08) : 3178 - 3180
  • [8] THE PICLAVINES, ANTIMICROBIAL INDOLIZIDINES FROM THE TUNICATE CLAVELINA-PICTA
    RAUB, MF
    CARDELLINA, JH
    SPANDE, TF
    [J]. TETRAHEDRON LETTERS, 1992, 33 (17) : 2257 - 2260
  • [9] LEPADIN-A, A DECAHYDROQUINOLINE ALKALOID FROM THE TUNICATE CLAVELINA-LEPADIFORMIS
    STEFFAN, B
    [J]. TETRAHEDRON, 1991, 47 (41) : 8729 - 8732