Polyketide-peroxides from a Species of Jamaican Plakortis (Porifera: Demospongiae)

Rabab Mohammed; Jiangnan Peng; Michelle Kelly; Muhammad Yousaf; Eustace Winn; Srinivas Odde; Zhi Bie; Aihua Xie; Robert J. Doerksen; Mark T. Hamann

doi:10.1071/CH09665

RESEARCH FRONT

Polyketide-peroxides from a Species of Jamaican Plakortis (Porifera: Demospongiae)

Rabab Mohammed ^A ^F , Jiangnan Peng ^A , Michelle Kelly ^B , Muhammad Yousaf ^A , Eustace Winn ^A , Srinivas Odde ^C ^G , Zhi Bie ^C , Aihua Xie ^C , Robert J. Doerksen ^C ^D and Mark T. Hamann ^A ^D ^E ^H

+ Author Affiliations

- Author Affiliations

^A Department of Pharmacognosy, The University of Mississippi, Oxford, MS 38677, USA.

^B National Institute of Water and Atmospheric Research Ltd, Auckland, New Zealand.

^C Department of Medicinal Chemistry, The University of Mississippi, Oxford, MS 38677, USA.

^D National Center for Natural Products Research, The University of Mississippi, Oxford, MS 38677, USA.

^E Departments of Pharmacology, Chemistry and Biochemistry, The University of Mississippi, Oxford, MS 38677, USA.

^F Current address: Department of Pharmacognosy, School of Pharmacy, Beni Suef University, Egypt.

^G Current address: Department of Pharmacology and Pharmaceutical Sciences, School of Pharmacy, University of Southern California, Los Angeles, CA 90089, USA.

^H Corresponding author. Email: mthamann@olemiss.edu

Australian Journal of Chemistry 63(6) 877-885 https://doi.org/10.1071/CH09665
Submitted: 19 December 2009 Accepted: 16 February 2010 Published: 11 June 2010

Abstract

A new cyclic peroxide plakortisinic acid (1), and a new ketone derivative (2), in addition to six known compounds, an α,β-unsaturated ester (3), plakortide N (4), plakortide F (5) and its free acid (6), plakortone D (7), and a furan-containing molecule (8), were isolated from a species of Plakortis from Jamaica. The structures were elucidated by interpretation of 1D and 2D NMR spectra, and mass spectrometry data and by comparison with data from the literature. Comparison between experimental and calculated optical rotations allowed the assignment of absolute configuration of 1 and 2. The isolated compounds have been evaluated for their antimicrobial, antimalarial, anticancer, anti-Mtb, and anti HIV-1 activity.

Acknowledgement

We thank Dr Melissa Jacob for testing the antimicrobial activities. We also thank John M. Trott and Mahitha Orugnati for antimalarial and antileishmanial assay. We are grateful to NIH grant number 1RO1AI36596 (M.T.H.); to the National Center for Zoonotic, Vector-borne, and Enteric Diseases (CK) of the Centers for Disease Control and Prevention (U01/CI000211) (M.T.H. and R.J.D.); to the University of Mississippi and for MCSR computing facilities (R.J.D.). This investigation was conducted in part in a facility constructed with support from research facilities improvement program C06 RR-14503–01 from the NIH National Center for Research Resources. The work was supported in part by the Egyptian Government (predoctoral fellowship for R. Mohammed). The Discovery Bay Marine Laboratory in Discovery Bay, Jamaica, is gratefully acknowledged for their help with collection of samples, Raymond Schinazi's group with Emory for evaluation in HIV-1 assays and Scott Franzblau's group at UIC for Mtb.

References

Polyketide-peroxides from a Species of Jamaican Plakortis (Porifera: Demospongiae)

Abstract

Acknowledgement

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