Taurospongin A, a novel acetylenic fatty acid derivative inhibiting DNA polymerase beta and HIV reverse transcriptase from sponge Hippospongia sp.

被引:67
作者
Ishiyama, H
Ishibashi, M
Ogawa, A
Yoshida, S
Kobayashi, J
机构
[1] HOKKAIDO UNIV,FAC PHARMACEUT SCI,SAPPORO,HOKKAIDO 060,JAPAN
[2] NAGOYA UNIV,SCH MED,CANC CELL BIOL LAB,DIS MECHANISM & CONTROL RES INST,NAGOYA,AICHI 466,JAPAN
关键词
D O I
10.1021/jo970206r
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Taurospongin A (1), a novel acetylene-containing natural product consisting of a taurine and two fatty acid residues, has been isolated from the Okinawan marine sponge Hippospongia sp. and its structure elucidated by spectral data and chemical means. Taurospongin A (1) exhibited potent inhibitory activity against DNA polymerase beta and HIV reverse transcriptase. The absolute configurations of taurospongin A (1) were established to be 3R, 7S, and 9R by synthesis of the MTPA ester of a degradation product of 1.
引用
收藏
页码:3831 / 3836
页数:6
相关论文
共 21 条
  • [1] CARDUUSYNES (A-E) - ACETYLENIC ACIDS FROM A GREAT-AUSTRALIAN-BIGHT MARINE SPONGE PHAKELLIA-CARDUUS
    BARROW, RA
    CAPON, RJ
    [J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1994, 47 (10) : 1901 - 1918
  • [2] A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS
    CARLSEN, PHJ
    KATSUKI, T
    MARTIN, VS
    SHARPLESS, KB
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) : 3936 - 3938
  • [3] Pinnaic acid and tauropinnaic acid: Two novel fatty acids composing a 6-Azaspiro[4.5]decane unit from the Okinawan bivalve Pinna muricata
    Chou, T
    Kuramoto, M
    Otani, Y
    Shikano, M
    Yazawa, K
    Uemura, D
    [J]. TETRAHEDRON LETTERS, 1996, 37 (22) : 3871 - 3874
  • [4] Costantino V, 1995, LIEBIGS ANN-RECL, P2133
  • [5] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES
    DALE, JA
    DULL, DL
    MOSHER, HS
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) : 2543 - &
  • [6] DECOUPLED HMBC (D-HMBC), AN IMPROVED TECHNIQUE OF HMBC
    FURIHATA, K
    SETO, H
    [J]. TETRAHEDRON LETTERS, 1995, 36 (16) : 2817 - 2820
  • [7] ANTIFUNGAL BROMINATED C-18 ACETYLENIC ACIDS FROM THE MARINE SPONGE, PETROSIA-VOLCANO HOSHINO
    FUSETANI, N
    LI, HY
    TAMURA, K
    MATSUNAGA, S
    [J]. TETRAHEDRON, 1993, 49 (06) : 1203 - 1210
  • [8] FATTY-ACIDS PART 50 - C-13-NUCLEAR MAGNETIC-RESONANCE STUDIES OFOLEFINIC FATTY-ACIDS AND ESTERS
    GUNSTONE, FD
    POLLARD, MR
    SCRIMGEOUR, CM
    VEDANAYAGAM, HS
    [J]. CHEMISTRY AND PHYSICS OF LIPIDS, 1977, 18 (01) : 115 - 129
  • [9] METACHROMIN-A AND METACHROMIN-B, NOVEL ANTINEOPLASTIC SESQUITERPENOIDS FROM THE OKINAWAN SPONGE HIPPOSPONGIA CF METACHROMIA
    ISHIBASHI, M
    OHIZUMI, Y
    CHENG, J
    NAKAMURA, H
    HIRATA, Y
    SASAKI, T
    KOBAYASHI, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (12) : 2855 - 2858
  • [10] Ishibashi M, 1997, HETEROCYCLES, V44, P543