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Volumn 67, Issue 8, 2004, Pages 1374-1382

Isolation and structure assignments of rostratins A-D, cytotoxic disulfides produced by the marine-derived fungus Exserohilum rostratum

Author keywords

[No Author keywords available]

Indexed keywords

DISULFIDE; ROSTRATIN A; ROSTRATIN B; ROSTRATIN C; ROSTRATIN D; UNCLASSIFIED DRUG;

EID: 4344716608     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np049920b     Document Type: Article
Times cited : (132)

References (29)
  • 1
    • 0037238780 scopus 로고    scopus 로고
    • and related references therein
    • Nygren, P.; Larsson, R. J. Internal Med. 2003, 253, 46-75, and related references therein.
    • (2003) J. Internal Med. , vol.253 , pp. 46-75
    • Nygren, P.1    Larsson, R.2
  • 24
    • 4344710993 scopus 로고    scopus 로고
    • note
    • The difference in the rates of acylation of the hydroxyl groups on C-5(5′) and C-8(8′) in 1 is likely due to the ability of the latter to form a hydrogen bond to the carbonyl on C-1(1′). Inspeetion of molecular models suggests these two functional groups are quite close.
  • 26
    • 4344692808 scopus 로고    scopus 로고
    • note
    • It should be noted that 3 is assigned a C-8(8′) = R configuration, while 1 and 2 possess C-8(8′) configurations despite the fact that the hydroxyl groups are alpha in all three metabolites. The replacement of one of the hydrogens at C-8(8′) in 1 and 2 with a methoxyl functionality in 3 reverses the Cahn-Ingold-Prelog priorities. The same phenomenon is seen with rostratin D (4).
  • 27
    • 4344653170 scopus 로고    scopus 로고
    • note
    • The regioselective acylation of 4 is most likely due to the greater nucleophilicity of the alcohol as compared to the thiol.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.