Elsevier

Phytochemistry

Volume 52, Issue 3, October 1999, Pages 453-457
Phytochemistry

Bioactive naphthoquinones from Cordyceps unilateralis

https://doi.org/10.1016/S0031-9422(99)00272-1Get rights and content

Abstract

Six bioactive naphthoquinone derivatives, erythrostominone, deoxyerythrostominone, 4-O-methyl erythrostominone, epierythrostominol, deoxyerythrostominol and 3,5,8-trihydroxy-6-methoxy-2-(5-oxohexa-1,3-dienyl)-1,4-naphthoquinone, were isolated from the insect pathogenic fungus Cordyceps unilateralis BCC1869. While the latter is synthetically known, both it and 4-O-methyl erythrostominone are products of fungus strain C. unilateralis BCC1869.

Introduction

As part of the ongoing multidisciplinary research activity at the National Center for Genetic Engineering and Biotechnology (BIOTEC), insect pathogenic fungi have been routinely collected from various parts of Thailand. Fungi in our collection were grown under laboratory conditions and many strains were found in screening systems to produce secondary metabolites exhibiting various biological activities ranging from activity against malaria parasites, fungi, virus, mycobacteria and tumor cell lines. The strain of Cordyceps unilateralis BCC1869 is one of the fungi in our laboratory producing bioactive substances; hence activity-guided isolation and identification of its bioactive substances were undertaken and results are presented in this paper.

Section snippets

Results and discussion

EtOAc extract of a culture broth of C. unilateralis BCC1869 yielded compounds 16 after purification with a gel filtration column chromatography and a MPLC using a C18 reversed phase column. The previously known red compounds 1, 2, 4 and 5 were identified, based upon their spectroscopic data, as erythrostominone, deoxyerythrostominone, epierythrostominol and deoxyerythrostominol, respectively. These compounds were previously reported to be antibacterial constituents in the fungus Gnomonia

Experimental

1H, 13C, DEPT (Doddrell, Pegg & Bendall, 1982), 1H–1H COSY (Derome & Williamson, 1990), HMQC (Bax, Griffey & Hawkins, 1983) (optimized for 1JHC=145 Hz) and HMBC (Bax & Summers, 1986) (optimized for nJHC=8.0 Hz) spectra were recorded on a Bruker DRX 400, operating at 400.1 MHz for proton and 100.6 MHz for carbon. EIMS (70 eV) spectra were obtained from a Micromass Platform II mass spectrometer.

Acknowledgements

We are grateful to the Biodiversity Research and Training Program and the BIOTEC/NSTDA, for financial support. One of us (Y.T.) thanks the National Science and Technology Development Agency (NSTDA) for the Senior Research Fellowship Award. We thank the BIOTEC fermentation technology laboratory and bioassay research facility for mass cultivation of the fungus and bioactivity test, respectively. We thank Dr. Ryohei Yamaoka, Kyoto Institute of Technology, Japan, for HR-EIMS data.

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