Six New Polyacetylenic Alcohols from the Marine Sponges Petrosia sp. and Halichondria sp.

Adeyemi Francis Gabriel, Zhen Li, Ryouhei Kusuda, Chiaki Tanaka, Tomofumi Miyamoto

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Six new polyacetylenic alcohols, termed strongylotriols A and B; pellynols J, K, and L; and isopellynol A, together with three known polyacetylenic alcohols, pellynols A, B, and C were isolated from the marine sponges Petrosia sp., and Halichondria sp. collected in Okinawa, Japan. Their planer structures were determined based on 2D-NMR and mass spectrometric analysis of the degraded products by RuCl3 oxidation. The absolute stereochemistry of isolates was examined by their Mosher's esters. The strongylotriols were found to be optically pure compounds, whereas the pellynols are diastereomeric mixtures at the C-6 position. Proliferation experiments using the HeLa and K562 cell lines suggested that the essential structural units for activity are the "hexa-2,4-diyn-1,6-diol" and "pent-1-en-4-yn-3-ol" on the termini.

Original languageEnglish
Pages (from-to)469-475
Number of pages7
JournalChemical and Pharmaceutical Bulletin
Volume63
Issue number6
DOIs
Publication statusPublished - Jun 1 2015

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Petrosia
Porifera
Alcohols
Stereochemistry
K562 Cells
HeLa Cells
Japan
Esters
Cells
Nuclear magnetic resonance
Cell Line
Oxidation
Experiments

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Drug Discovery

Cite this

Six New Polyacetylenic Alcohols from the Marine Sponges Petrosia sp. and Halichondria sp. / Gabriel, Adeyemi Francis; Li, Zhen; Kusuda, Ryouhei; Tanaka, Chiaki; Miyamoto, Tomofumi.

In: Chemical and Pharmaceutical Bulletin, Vol. 63, No. 6, 01.06.2015, p. 469-475.

Research output: Contribution to journalArticle

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