Planta Med 2016; 82 - PC31
DOI: 10.1055/s-0036-1578733

New C-33 Polyacetylenic Acid From The Marine Sponge Halichondria Sp.

AF Gabriel 1, C Tanaka 2, T Miyamoto 2
  • 1Chemistry Department, Faculty of Science, University of Abuja, PMB 117 Abuja, Nigeria
  • 2Department of Natural Products Chemistry, Graduate School of Pharmaceutical Sciences, Kyushu University, Maidaishi 3 – 1-1 Higashiku Fukuoka, 812 – 8582, Japan

Polyacetelynic compounds have been shown to possess diverse pharmacological activities which include antitumor, antiviral, antimicrobial and anti-inflammatory activities [1, 2]. Literature has revealed the isolation of pellynic acid from triangulata (Truk) [3]. Pellynic acid has been reported to inhibit IMPDH (Inosine Monophosphate Dehydrogenase) [3].

This work is a report on the isolation and structure elucidation of novel polyacetylenic acid from the marine sponge Halichondria sp. collected in Iriomote Island, Okinawa, Japan. The specimen was extracted with ethanol and the crude extract was further partitioned to give ether, n-butanol and water extracts. The ether extract was fractionated by column chromatography and the fraction therefrom was further purified by C30 reversed phase HPLC to yield compounds 1 – 4 which are long chain polyacetylenic acids. The structure elucidation was carried out using 2D-NMR and mass spectrometric analysis of the products derived from the RuCl3 oxidation. The absolute stereochemistry of 1 was determined to be R at C-31.

Fig. 1

References:

[1] Gabriel A.F. et al. (2015) Bulletins of the Pharmaceutical Society of Japan, 63, 2015.06;

[2] Allen, E.H. et al. (1971) Phytochemistry 10: 1579 – 1582

[3] X. Fu, (1997) Tetrahedron, 53, 799 – 814.