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Polyacetylene diols with antiproliferative and driving Th1 polarization effects from the marine sponge Callyspongia sp.

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Abstract

A screening of 30 crude extracts of marine sponges against human promyelocytic leukemia cells (HL-60) yielded an EtOAc extract of the sponge Callyspongia sp. (Callyspongiidae) with significant activity. Further bioassay-guided fractionation of the EtOAc extract led to the isolation of three polyacetylene metabolites: a new polyacetylene diol, callyspongidiol (1), along with two known compounds, siphonodiol (2) and 14,15-dihydrosiphonodiol (3). Their structures were determined by a combination of spectroscopic analyses. Compounds 1–3 exhibited antiproliferative activity against HL-60 with IC50 values of 6.5, 2.8, and 6.5 µg/ml, respectively. These metabolites induce apoptosis in HL-60 cells. Dendritic cells (DC) differentiated with 1–3 enhance the differentiation of naïve T cells towards the Th1 type.

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Acknowledgments

We are grateful to Professor P. R. Bergquist of Auckland University for her kind identification and the taxonomic description of the sponge. We thank Mr. K. Murakami and Mr. K. Iwasaki for help with collections. We are indebted to Dr. M. Tanaka for measurements of the 600 MHz NMR spectra and Ms. I. Okamoto, Faculty of Pharmaceutical Sciences of this University, for measurements of mass spectra.

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Authors and Affiliations

  1. Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Tokushima, Japan

    Akemi Umeyama, Nanae Matsuoka, Rieko Mine, Akemi Nakata, Eri Arimoto, Miwa Matsui, Noboru Shoji, Shigenobu Arihara & Toshihiro Hashimoto

  2. Research Center for Cancer Immunotherapy, Chonnam National University Hwasun Hospital, Jeonnam, South Korea

    Masao Takei

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  1. Akemi Umeyama
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  2. Nanae Matsuoka
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  10. Toshihiro Hashimoto
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Correspondence to Akemi Umeyama.

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Umeyama, A., Matsuoka, N., Mine, R. et al. Polyacetylene diols with antiproliferative and driving Th1 polarization effects from the marine sponge Callyspongia sp.. J Nat Med 64, 93–97 (2010). https://doi.org/10.1007/s11418-009-0363-3

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  • DOI: https://doi.org/10.1007/s11418-009-0363-3

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