Abstract

Six new cyclic peroxides (1–6) were isolated from the Korean sponge Plakortis simplex, along with two new alkylpyridinium alkaloids (7 and 8). The structures of these compounds were completely determined by a combination of NMR analysis and chemical reactions. Compounds 1–6 exhibited cytotoxic/antifungal activities against RAW264.7 cells and Candida albicans.

Highlights

  • Sponges of the family Plakinidae have provided structurally noble and biologically active metabolites including alkaloids, glycolipids, lactones and polyketides [1,2,3,4,5]

  • As part of our search for new metabolites from the extracts of the Korean sponges, we isolated six cyclic peroxides (1–6) from fractions of Plakortis simplex which showed toxicity against C. albicans in a disk agar diffusion method

  • Compound 1 was determined to have a molecular formula of C18H32O5 on the basis of high-resolution fast-atom bombardment mass spectrometry (HRFABMS) and the 13C NMR spectrum, which was consistent with three degrees of unsaturation

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Summary

Introduction

Sponges of the family Plakinidae have provided structurally noble and biologically active metabolites including alkaloids, glycolipids, lactones and polyketides [1,2,3,4,5]. Numerous polyketides containing a five- or six-membered peroxide group have been isolated from Plakinidae since the identification of plakortin in 1978 [6,7,8,9,10]. These compounds exhibited several biological activities, such as cytotoxic, antifungal, and antimalarial properties, making them potentially useful in the development of drugs or as research tools [11,12,13]. We describe the isolation, stereostructural characterization of all of the isolated compounds, together with activities for six peroxide compounds

Results and Discussion
General Experimental Procedures
Material
Extraction and Isolation
MTPA Reaction of Reduced Compounds 1 and 4
Biological Activities
Conclusions
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