4.7 Article

Aflaquinolones A-G: Secondary Metabolites from Marine and Fungicolous Isolates of Aspergillus spp.

Journal

JOURNAL OF NATURAL PRODUCTS
Volume 75, Issue 3, Pages 464-472

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/np200958r

Keywords

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Funding

  1. National Science Foundation [CHE-0718315, CHE-11011847, AGS 0927944]
  2. National Institutes of Health [S10 RR023384, S10 RR02.5500]
  3. Global RD Center (GRDC)
  4. Korean Ministry of Education, Science & Technology (MEST)
  5. Marine Biotechnology Program
  6. Ministry of Land, Transport, and Maritime Affairs of the Korean Government
  7. Division Of Chemistry
  8. Direct For Mathematical & Physical Scien [1011847] Funding Source: National Science Foundation

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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 H-1 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.

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