Aflaquinolones A-G: secondary metabolites from marine and fungicolous isolates of Aspergillus spp

Scott A Neff; Sang Un Lee; Yukihiro Asami; Jong Seog Ahn; Hyuncheol Oh; Jonas Baltrusaitis; James B Gloer; Donald T Wicklow

doi:10.1021/np200958r

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Aflaquinolones A-G: secondary metabolites from marine and fungicolous isolates of Aspergillus spp

Journal article

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Aflaquinolones A-G: secondary metabolites from marine and fungicolous isolates of Aspergillus spp

Scott A Neff, Sang Un Lee, Yukihiro Asami, Jong Seog Ahn, Hyuncheol Oh, Jonas Baltrusaitis, James B Gloer and Donald T Wicklow

Journal of natural products (Washington, D.C.), Vol.75(3), pp.464-472

03/23/2012

DOI: 10.1021/np200958r

PMCID: PMC3311757

PMID: 22295903

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Abstract

Seven new compounds (aflaquinolones A-G; 1-7) containing dihydroquinolin-2-one and terpenoid units have been isolated from two different fungal sources. Two of these metabolites (1 and 2) were obtained from a Hawaiian fungicolous isolate of Aspergillus sp. (section Flavipedes; MYC-2048 = NRRL 58570), while the others were obtained from a marine Aspergillus isolate (SF-5044) collected in Korea. The structures of these compounds were determined mainly by analysis of NMR and MS data. Relative and absolute configurations were assigned on the basis of NOESY data and (1)H NMR J-values, comparison of calculated and experimental ECD spectra, and analysis of a Mosher's ester derivative of 2. Several known compounds, including alantrypinone, aspochalasins I and J, methyl 3,4,5-trimethoxy-2((2-((3-pyridinylcarbonyl)amino)benzoyl)amino)benzoate, and trans-dehydrocurvularin were also encountered in the extract of the Hawaiian isolate.

Hawaii

Marine Biology

Quinolones - isolation & purification

Stereoisomerism

Humans

Aspergillus - chemistry

Microbial Sensitivity Tests

Democratic People's Republic of Korea

Quinolones - chemistry

HL-60 Cells

Nuclear Magnetic Resonance, Biomolecular

Molecular Structure

Staphylococcus aureus

Details

Title: Subtitle: Aflaquinolones A-G: secondary metabolites from marine and fungicolous isolates of Aspergillus spp
Creators: Scott A Neff - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, United States
Sang Un Lee
Yukihiro Asami
Jong Seog Ahn
Hyuncheol Oh
Jonas Baltrusaitis
James B Gloer
Donald T Wicklow
Resource Type: Journal article
Publication Details: Journal of natural products (Washington, D.C.), Vol.75(3), pp.464-472
DOI: 10.1021/np200958r
PMID: 22295903
PMCID: PMC3311757
NLM abbreviation: J Nat Prod
ISSN: 0163-3864
eISSN: 1520-6025
Publisher: United States
Grant note: S10 RR023384-01 / NCRR NIH HHS S10 RR025500-01 / NCRR NIH HHS S10 RR023384 / NCRR NIH HHS S10 RR025500 / NCRR NIH HHS
Language: English
Date published: 03/23/2012
Academic Unit: Chemistry
Record Identifier: 9983985869502771

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