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Volumn 73, Issue 10, 2010, Pages 1694-1700

Bioactive cycloperoxides isolated from the Puerto Rican sponge Plakortis halichondrioides

Author keywords

[No Author keywords available]

Indexed keywords

EPIPLAKINIC ACID F METHYL ESTER; EPIPLAKINIDIOIC ACID; PLAKORTOLIDE F; PLAKORTOLIDE J; POLYKETIDE; UNCLASSIFIED DRUG; ANTIMALARIAL AGENT; FUSED HETEROCYCLIC RINGS; PEROXIDE; TUBERCULOSTATIC AGENT;

EID: 77958548626     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np100461t     Document Type: Article
Times cited : (43)

References (41)
  • 23
    • 77958543190 scopus 로고    scopus 로고
    • The trivial name plakortolide F was claimed simultaneously by Hamann (ref 5d) and Wright (ref 4d) for two peroxide-lactones isolated from distinct Plakinastrella sponge species. The compound herein referred to as plakortolide F (i. e., 5) was identical to the material reported by the Wright group
    • The trivial name plakortolide F was claimed simultaneously by Hamann (ref 5d) and Wright (ref 4d) for two peroxide-lactones isolated from distinct Plakinastrella sponge species. The compound herein referred to as plakortolide F (i. e., 5) was identical to the material reported by the Wright group.
  • 24
    • 77958572061 scopus 로고    scopus 로고
    • 37Rv at concentrations ≥ 64 μg/mL
    • 37Rv at concentrations ≥ 64 μg/mL.
  • 27
    • 77958605015 scopus 로고    scopus 로고
    • For related peroxide-lactones having trans methyl substituents at the C-4 and C-6 positions, see refs 5b and 5d
    • For related peroxide-lactones having trans methyl substituents at the C-4 and C-6 positions, see refs 5b and 5d.
  • 30
    • 77958583115 scopus 로고    scopus 로고
    • The lowest value for ΔΔδ in the article by Kishi and coworkers (ref 9a) is -0.029
    • The lowest value for ΔΔδ in the article by Kishi and coworkers (ref 9a) is -0.029.
  • 31
    • 77958606041 scopus 로고    scopus 로고
    • The conjugated polyene chain of compounds 1, 2, and 4 is a reactive, electron-rich system that is likely susceptible to attack by electrophilic reagents such as hydroxy and peroxy radicals and thus is responsible for the instability of these compounds toward oxidation
    • The conjugated polyene chain of compounds 1, 2, and 4 is a reactive, electron-rich system that is likely susceptible to attack by electrophilic reagents such as hydroxy and peroxy radicals and thus is responsible for the instability of these compounds toward oxidation.
  • 32
    • 77958580962 scopus 로고    scopus 로고
    • Given their extreme chemical instability, we speculate that Nature uses unsaturated conjugated polyenes such as 1, 2, and 4 as biogenetic precursors to the phenyl polyketide peroxide series of Plakortis / Plakinastrella metabolites (i.e., the plakortolides) via a cascade of efficient E / Z -isomerizations, electrocyclizations, and further dehydrogenations to account for aromatic ring formation. For articles suggesting that some of these conversions are chemically viable, see
    • Given their extreme chemical instability, we speculate that Nature uses unsaturated conjugated polyenes such as 1, 2, and 4 as biogenetic precursors to the phenyl polyketide peroxide series of Plakortis / Plakinastrella metabolites (i.e., the plakortolides) via a cascade of efficient E / Z -isomerizations, electrocyclizations, and further dehydrogenations to account for aromatic ring formation. For articles suggesting that some of these conversions are chemically viable, see
  • 35
    • 77958564088 scopus 로고    scopus 로고
    • Wright and co-workers reported that free acid 4 showed moderate antifungal activity against Candida albicans, whereas 5 was inactive against both C. albicans and Aspergillus fumigatus; see ref 4d
    • Wright and co-workers reported that free acid 4 showed moderate antifungal activity against Candida albicans, whereas 5 was inactive against both C. albicans and Aspergillus fumigatus; see ref 4d.
  • 36
    • 77958611941 scopus 로고    scopus 로고
    • In order to obtain reliable results, it is essential that both R - and S -enantiomers of the shift reagent be of similar quality (purity and moisture content) and that NMR data with both the R - and S -shift reagent be collected on the same instrument
    • In order to obtain reliable results, it is essential that both R-and S -enantiomers of the shift reagent be of similar quality (purity and moisture content) and that NMR data with both the R-and S -shift reagent be collected on the same instrument.
  • 37
    • 77958587720 scopus 로고    scopus 로고
    • 13C NMR chemical shifts assigned to the carbonyl carbons of 3 are not very accurate, as these signals were weak and broad. The assignments shown can be interchanged
    • 13C NMR chemical shifts assigned to the carbonyl carbons of 3 are not very accurate, as these signals were weak and broad. The assignments shown can be interchanged.
  • 38
    • 77958517182 scopus 로고    scopus 로고
    • It has been noted that Δδ are always greater with chiral Pr-based shift reagents than with the corresponding Eu-based shift reagents. Thus, the former lanthanide shift reagents have a superior capacity for enantiotopic discrimination of carbons within a molecule; see ref 9a
    • It has been noted that Δδ are always greater with chiral Pr-based shift reagents than with the corresponding Eu-based shift reagents. Thus, the former lanthanide shift reagents have a superior capacity for enantiotopic discrimination of carbons within a molecule; see ref 9a.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.