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Volumn 63, Issue 23, 1998, Pages 8346-8354

Neomangicols: Structures and absolute stereochemistries of unprecedented halogenated sesterterpenes from a marine fungus of the genus Fusarium

Author keywords

[No Author keywords available]

Indexed keywords

GENTAMICIN; NEOMANGICOL A; NEOMANGICOL B; NEOMANGICOL C; SESTERTERPENE; UNCLASSIFIED DRUG;

EID: 0032514839     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981226b     Document Type: Article
Times cited : (70)

References (38)
  • 13
    • 14444276592 scopus 로고    scopus 로고
    • note
    • This fungus was identified as a strain of Fusarium heterosporum by David Porter (U. Georgia) based on morphological characteristics and as Fusarium sp. by FAME analysis (Microbial I.D., Inc., Newark, DE) with a similarity index of 0.965.
  • 14
    • 14444267410 scopus 로고    scopus 로고
    • note
    • Fractions were bioassayed against HCT-116, a human colon cancer cell line.
  • 16
    • 14444283708 scopus 로고    scopus 로고
    • note
    • 1H NMR chemical shifts for these protons were δ 5.28, 4.70, 4.63, 4.53, and 3.89.
  • 17
    • 14444283466 scopus 로고    scopus 로고
    • note
    • 1H NMR chemical shifts for these protons were δ 6.19, 5.43, 4.90, 4.56, and 4.20.
  • 18
    • 14444283961 scopus 로고    scopus 로고
    • note
    • The Chem3D structures shown in this and following figures are low-energy conformers identified by a Monte Carlo conformation search performed in Macromodel 6.0 using the MM2 force field. No competing low energy conformers within the range of 2 kcal/mol were defined. Some hydrogens have been hidden for clarity. For this conformation search, the side chain was simulated as a methyl group.
  • 20
    • 14444269975 scopus 로고    scopus 로고
    • note
    • Stereochemical descriptors for C-17, C-18, and C-19 were based on an arbitrary assignment of C-14 as S. For ease of reading, we have abbreviated 17R, 18R, 19R as RRR (etc.) in the discussion of the side chain stereochemistry.
  • 24
    • 14444276360 scopus 로고    scopus 로고
    • note
    • These conformation searches were performed on the entire molecules described. Much of the polycyclic ring structure, as well as some hydrogens, is hidden for clarity.
  • 25
    • 14444269544 scopus 로고    scopus 로고
    • note
    • We had observed this color change during purification of the initial fermentations. As the change in TLC behavior between 1 and 3 is almost imperceptible, we originally attributed the color change to decomposition of a minor component.
  • 34
    • 0025605643 scopus 로고
    • Three halogenated norsesterterpenes have been reported from Ircinia sponges. (a) De Giulio, A.; De Rosa, S.; Di Vincenzo, G.; Strazzullo, G.; Zavodnik, N. J. Nat. Prod. 1990, 53, 1503. (b) N'Diaye, I.; Guella, G.; Mancini, I.; Kornprobst, J.-M.; Pietra, F. J. Chem. Soc, Chem. Commun. 1991, 97.
    • (1990) J. Nat. Prod. , vol.53 , pp. 1503
    • De Giulio, A.1    De Rosa, S.2    Di Vincenzo, G.3    Strazzullo, G.4    Zavodnik, N.5
  • 38
    • 14444272849 scopus 로고    scopus 로고
    • note
    • Antibacterial activity was determined using the standard discdiffusion assay. Neomangicol B (50 μg) caused a 10 mm zone of inhibition during a 24-h incubation period, compared to the standard gentamycin (10μg), which also resulted in a 10 mm zone of inhibition.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.