(3R,4S)-isostreptenol III from Penicillium purpurogenum MM

Abstract

In continuation of the search for new compounds from the terrestrial fungus Penicillium purpurogenum MM, (3R,4S)-isostreptenol III (1), a further new natural compound is reported. The chemical structure of 1 was confirmed by extensive 1D and 2D NMR and ESI HR mass measurements, and by comparison with literature data. The absolute configuration was determined by ab initio calculations of ECD, ORD, and NMR data. The antimicrobial and cytotoxic activities of the crude extract and 1 were reported using a set of microorganisms and by the brine shrimp assay, respectively.

Graphical Abstract

Keywords:

• Penicillium purpurogenum
• (3R,4S)-isostreptenol III
• structure elucidation
• biological activity

Acknowledgements

The author is greatly thankful to Prof. H. Laatsch for lab facilities and unlimited support during this research work. Dr. H. Frauendorf and Mr. R. Machinek for the spectral measurements, F. Lissy for biological activity testing, and special thankful to Dr. Warren Hehre (Wavefunction, Inc., Irvine, CA, USA) for his help to make better use of SPARTAN and contributed most of the NMR calculations.

Disclosure statement

No potential conflict of interest was reported by the authors.

Figure 1. Chemical structure of (3R,4S)-isostreptenol III (1).

Additional information

Funding

This research project was financed by the PPP Egypt 09 program (German Egyptian Scientific Projects of the German Academic Exchange Service).