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

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

doi:10.1248/cpb.c15-00203

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 journal › Article › peer-review

7 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 language	English
Pages (from-to)	469-475
Number of pages	7
Journal	Chemical and Pharmaceutical Bulletin
Volume	63
Issue number	6
DOIs	https://doi.org/10.1248/cpb.c15-00203
Publication status	Published - Jun 1 2015

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Chemistry(all)
Drug Discovery

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title = "Six New Polyacetylenic Alcohols from the Marine Sponges Petrosia sp. and Halichondria sp.",

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.",

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T1 - Six New Polyacetylenic Alcohols from the Marine Sponges Petrosia sp. and Halichondria sp.

AU - Gabriel, Adeyemi Francis

AU - Li, Zhen

AU - Kusuda, Ryouhei

AU - Tanaka, Chiaki

AU - Miyamoto, Tomofumi

PY - 2015/6/1

Y1 - 2015/6/1

N2 - 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.

AB - 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.

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

Abstract

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