Structure and stereochemistry of a new cytotoxic polychlorinated sulfolipid from Adriatic shellfish

被引:58
作者
Ciminiello, P
Dell'Aversano, C
Fattorusso, E
Forino, M
Magno, S
Di Rosa, M
Ianaro, A
Poletti, R
机构
[1] Univ Naples Federico 2, Dipartimento Chim Sostanze Nat, I-80131 Naples, Italy
[2] Univ Naples Federico 2, Dipartimento Farmacol Sperimentale, I-80131 Naples, Italy
[3] Ctr Ric Marine, I-47042 Cesenatico, FC, Italy
关键词
D O I
10.1021/ja0207347
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A detailed analysis of the causative toxins contained in the hepatopancreas of toxic mussels from the northern Adriatic sea has been carried out. Along with some DSP (diarrhetic shellfish poisoning) type toxins, such as okadaic acid, yessotoxin, and their derivatives, which are involved in a number of human intoxications throughout the world, we have now isolated a new cytotoxin, a polychlorinated sulfolipid 1, whose gross structure has been elucidated by spectral analysis, including various 2D NMR techniques. The relative stereochemistry of 1 was elucidated by successful application of the J-based configuration analysis developed for acyclic compounds using carbon-proton spin-coupling constants ((2,3)J(C,H)) and proton-proton spin-coupling constants ((3)J(H,H)); its absolute stereochemistry was established by the Mosher method. Compound 1 possesses in vitro cytotoxicity against WEHI 164 and RAW 264.7 cells.
引用
收藏
页码:13114 / 13120
页数:7
相关论文
共 30 条
  • [1] [Anonymous], MARINE COASTAL EUTRO
  • [2] SENSITIVITY-ENHANCED TWO-DIMENSIONAL HETERONUCLEAR SHIFT CORRELATION NMR-SPECTROSCOPY
    BAX, A
    SUBRAMANIAN, S
    [J]. JOURNAL OF MAGNETIC RESONANCE, 1986, 67 (03) : 565 - 569
  • [3] BONI L, 1993, DEV MAR BIO, V3, P475
  • [4] Structure determination of carboxyhomoyessotoxin, a new yessotoxin analogue isolated from adriatic mussels
    Ciminiello, P
    Fattorusso, E
    Forino, M
    Poletti, R
    Viviani, R
    [J]. CHEMICAL RESEARCH IN TOXICOLOGY, 2000, 13 (08) : 770 - 774
  • [5] Structural elucidation of a new cytotoxin isolated from mussels of the Adriatic sea
    Ciminiello, P
    Fattorusso, E
    Forino, M
    Di Rosa, M
    Ianaro, A
    Poletti, R
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (02) : 578 - 582
  • [6] Isolation of adriatoxin, a new analogue of yessotoxin from mussels of the Adriatic sea
    Ciminiello, P
    Fattorusso, E
    Forino, M
    Magno, S
    Poletti, R
    Viviani, R
    [J]. TETRAHEDRON LETTERS, 1998, 39 (48) : 8897 - 8900
  • [7] Isolation of 45-hydroxyyessotoxin from mussels of the Adriatic Sea
    Ciminiello, P
    Fattorusso, E
    Forino, M
    Magno, S
    Poletti, R
    Viviani, R
    [J]. TOXICON, 1999, 37 (04) : 689 - 693
  • [8] Yessotoxin in mussels of the northern Adriatic Sea
    Ciminiello, P
    Fattorusso, E
    Forino, M
    Magno, S
    Poletti, R
    Satake, M
    Viviani, R
    Yasumoto, T
    [J]. TOXICON, 1997, 35 (02) : 177 - 183
  • [9] Ciminiello P, 2000, EUR J ORG CHEM, V2000, P291
  • [10] Draisci R., 1996, Rivista di Scienza dell'Alimentazione, V25, P7