Psymberin, a potent sponge-derived cytotoxin from Psammocinia distantly related to the pederin family

被引:155
作者
Cichewicz, RH [1 ]
Valeriote, FA
Crews, P
机构
[1] Univ Calif Santa Cruz, Dept Chem & Biochem, Santa Cruz, CA 95064 USA
[2] Univ Calif Santa Cruz, Inst Marine Sci, Santa Cruz, CA 95064 USA
[3] Josephine Ford Canc Ctr, Div Hematol & Oncol, Detroit, MI 48202 USA
关键词
D O I
10.1021/ol049503q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Bioassay-guided fractionation of the sponge Psammocinia sp. afforded psymberin (1) possessing 5S,8S,9S,11R,13R,15S,16R,17R stereochemistry. Psymberin exhibits structural similarities to the pederin family metabolites. The potent cytotoxicty and unique structural features of 1 make it a promising lead for therapeutic development.
引用
收藏
页码:1951 / 1954
页数:4
相关论文
共 25 条
  • [1] A new brominated diphenyl ether from the marine sponge Dysidea herbacea
    Bowden, BF
    Towerzey, L
    Junk, PC
    [J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 2000, 53 (04) : 299 - 301
  • [2] BURRES NS, 1989, CANCER RES, V49, P2935
  • [3] Cyclocinamide A. An unusual cytotoxic halogenated hexapeptide from the marine sponge Psammocinia
    Clark, WD
    Corbett, T
    Valeriote, F
    Crews, P
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (39) : 9285 - 9286
  • [4] FAULKNER D J, 1973, Tetrahedron Letters, V39, P3821
  • [5] FURUSAKI A, 1968, Tetrahedron Letters, V60, P6301
  • [6] BIOACTIVE MARINE METABOLITES SERIES .41. THEOPEDERINS-A-E, POTENT ANTITUMOR METABOLITES FROM A MARINE SPONGE, THEONELLA SP
    FUSETANI, N
    SUGAWARA, T
    MATSUNAGA, S
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (14) : 3828 - 3832
  • [7] Studies belated to the absolute configuration of cyclocinamide A:: Total synthesis of 4(R),11(R)-cyclocinamide A
    Grieco, PA
    Reilly, M
    [J]. TETRAHEDRON LETTERS, 1998, 39 (49) : 8925 - 8928
  • [8] HASHIMOTO N, 1981, CHEM PHARM BULL, V29, P1475
  • [9] Induction of apoptosis by the marine sponge (Mycale) metabolites, mycalamide A and pateamine
    Hood, KA
    West, LM
    Northcote, PT
    Berridge, MV
    Miller, JH
    [J]. APOPTOSIS, 2001, 6 (03) : 207 - 219
  • [10] 3 NEW ONNAMIDE CONGENERS FROM THE OKINAWAN MARINE SPONGE THEONELLA SP
    KOBAYASHI, J
    ITAGAKI, F
    SHIGEMORI, H
    SASAKI, T
    [J]. JOURNAL OF NATURAL PRODUCTS, 1993, 56 (06): : 976 - 981