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Two new indole alkaloids, 2-(3,3-dimethylprop-1-ene)-costaclavine and 2-(3,3-dimethylprop-1-ene)-epicostaclavine, from the marine-derived fungus Aspergillus fumigatus

Abstract

Two new indole alkaloids, 2-(3,3-dimethylprop-1-ene)-costaclavine (1) and 2-(3,3-dimethylprop-1-ene)-epicostaclavine (2), together with the known compounds costaclavine (3), fumgaclavine A (4) and C (5), were isolated from the marine-derived fungus Aspergillus fumigatus. The planar structures of the two new compounds were elucidated on the basis of chemical and physicochemical evidence including MS, UV, IR and NMR spectra. Their stereochemistry was studied by NOESY, 1H–1H coupling constant and CD spectra. The compounds 1, 2, 3 and 5 showed weak cytotoxicity against a mouse leukemia cell line (P388).

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Acknowledgment

This work was financed by the Global COE Program for Chemistry Innovation, the University of Tokyo.

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Correspondence to Dahai Zhang or Kazuo Tachibana.

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Zhang, D., Satake, M., Fukuzawa, S. et al. Two new indole alkaloids, 2-(3,3-dimethylprop-1-ene)-costaclavine and 2-(3,3-dimethylprop-1-ene)-epicostaclavine, from the marine-derived fungus Aspergillus fumigatus . J Nat Med 66, 222–226 (2012). https://doi.org/10.1007/s11418-011-0565-3

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Keywords

  • Aspergillus fumigatus
  • Indole alkaloids
  • 2-(3,3-Dimethylprop-1-ene)-costaclavine
  • 2-(3,3-Dimethylprop-1-ene)-epicostaclavine
  • Stereochemistry