Issue 8, 2010
From the journal:

Organic & Biomolecular Chemistry

Pestalactams A–C: novel caprolactams from the endophytic fungus Pestalotiopsis sp.†

Rohan A. Davis,*a   Anthony R. Carroll,a   Katherine T. Andrews,ab   Glen M. Boyle,b   Truc Linh Tran,b   Peter C. Healy,a   John A. Kalaitzisc  and  Roger G. Shivasd  

* Corresponding authors

a Eskitis Institute, Griffith University, Brisbane, QLD 4111, Australia
E-mail: r.davis@griffith.edu.au
Fax: +61-7-3735-6001
Tel: +61-7-3735-6043

b Queensland Institute for Medical Research, Herston, Queensland, Australia, 4006; Griffith Medical Research College, a joint program of Griffith University and QIMR, Herston, Queensland, Australia

c School of Biotechnology and Biomolecular Sciences, The University of New South Wales, Sydney, NSW 2052, Australia

d Queensland Primary Industries and Fisheries, Indooroopilly, QLD 4068, Australia

Abstract

Chemical investigations of a fermentation culture from the endophytic fungus Pestalotiopsis sp. yielded three novel caprolactams, pestalactams A–C (1–3). The structures of 1–3 were determined by analysis of 1D and 2D-NMR, UV, IR, and MS data. The structure of pestalactam A was confirmed following single crystal X-ray diffraction analysis. Pestalactams A–C are the first C-7 alkylated caprolactam natural products to be reported. Pestalactams A (1) and B (2) were tested against two different strains of the malaria parasite Plasmodium falciparum (3D7 and Dd2), and the mammalian cell lines, MCF-7 and NFF, and showed modest in vitro activity in all assays.

Graphical abstract: Pestalactams A–C: novel caprolactams from the endophytic fungus Pestalotiopsis sp.

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Article information

DOI
https://doi.org/10.1039/B924169H
Article type
Paper
Submitted
19 Nov 2009
Accepted
22 Jan 2010
First published
10 Feb 2010

Org. Biomol. Chem., 2010,8, 1785-1790

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Pestalactams A–C: novel caprolactams from the endophytic fungus Pestalotiopsis sp.

R. A. Davis, A. R. Carroll, K. T. Andrews, G. M. Boyle, T. L. Tran, P. C. Healy, J. A. Kalaitzis and R. G. Shivas, Org. Biomol. Chem., 2010, 8, 1785 DOI: 10.1039/B924169H

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