Acetylenic Strongylodiols from a Petrosia (Strongylophora) Okinawan Marine Sponge

Abstract

Seven new long-chain acetylenic alcohols, strongylodiols D-J, were isolated from an Okinawan marine sponge of the genus Petrosia (Strongylophora). The structures of these compounds were elucidated on the basis of the results of spectroscopic analysis and chemical reaction. Analysis of the MNA esters of the acetylenic alcohols disclosed that these compounds were each an enantiomeric mixture in a different ratio.

Biosynthesis and function of polyacetylenes and allied natural products

“…Hydroxylation at the 6-position in a compound related to 34A may yield the strongylodiols A-J (34C-L), which were isolated from an Okinawan Petrosia (Strongylophora) sp. as enantiomeric (6R:6S) mixtures ranging from 97:3 to 69:31 for 34L and 34G, respectively [361,362]. It is uncommon to isolate natural products as enantiomeric mixtures; in this case, it is not yet known whether the mixture is an isolation artifact or reflective of the enzymatic activities.…”

Identification of Novel Acetylenic Alcohols and a New Dihydrothiopyranone from the Tropical Sponge Reniochalina sp.

“…Acetylenic alcohols, a group of sponge metabolites, exhibit great structural variations in chain length and functional groups [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18]. Most of these compounds have shown various interesting bioactivities such as brine shrimp lethality [1], cytotoxicity [2][3][4][5][6][9][10][11][12][13][14], a-glucosidase inhibition [15] and HIV-1 integrase inhibition [16].…”

“…This extract displayed moderate growth inhibition against several human tumor cell lines. Guided by the results of 1 H-NMR analysis, fractions of the crude extracts were obtained by solvent partitioning followed by the isolation and purification of compounds using different chromatographic methods including reversed-phase vacuum flash chromatography and C 18 HPLC. This resulted in the isolation of two pure acetylenic alcohols (1, 2) and a dihydrothiopyranone (3) (Fig.…”

Toxic Alcohols: Aliphatic Unsaturated Alcohols

“…They include callyspongines A and B (Rooney and Capon, 1998) Strongylodiols are long-chain di-and tri-acetylenic di-alcohols with a chain of 26 up to 31 carbon atoms. Strongylodiols A, B and C were isolated from a Petrosia Okinawan marine sponge of the genus Strongylophora (Watanabe et al, 2000), later other strongylodiols -strongylodiols D−J -were isolated and described (Watanabe et al, 2005). Strongylodiols exhibit cytotoxic activity (Kirkham et al, 2004).…”