Bioactive marine metabolites XX. Petrosynol and petrosynone, antimicrobial C30 polyacetylenes from the marine sponge sp.: Determination of the absolute configuration

Fusetani, Nobuhiro; Shiragaki, T.; Matsunaga, Shigeru; Hashimoto, Kayoko

doi:10.1016/s0040-4039(00)96494-3

Cited by 62 publications

(56 citation statements)

References 5 publications

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“…Thus by synthesizing both geometric isomers of duryne (62) and the subsequent enzymatic resolution, we conclude that the natural (þ)-duryne (62) reported by Wright et al has a central double bond geometry of (Z) and absolute configuration of (S,S) as shown in structure 62. This conclusion not only is consistent with all experimental data reported in this study, but also consistent with several known C 2 symmetric acetylenic alcohols isolated from marine sources [7,8,70,89].…”

Section: Durynesupporting

confidence: 93%

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Total synthesis of polyyne natural products

Gung

2008

Comptes Rendus. Chimie

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Section: Durynesupporting

confidence: 93%

“…The assignment of the absolute configurations is based on Burgess active site model for the lipases from Pseudomonas sp. [75] and was corroborated by a comparison to several known C 2 symmetric acetylenic alcohols isolated from marine sources [7,8,70,89].…”

Section: Dideoxypetrosynol a (63)mentioning

confidence: 58%

Total synthesis of polyyne natural products

Gung

2008

Comptes Rendus. Chimie

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“…Sponge genera known to feature polyacetylenic lipids include Petrosia (1)(2)(3)(4)(5)(6)(7)(8), Cribrochalina (9)(10)(11)(12), Tetrosia (13), Xestospongia (14,15), Siphonochalina (16), Reniera (17), Haliclona (18), and Callyspongia (19). This latter observation together with our recent experience in isolating novel lipids from a southern Australian Callyspongia sp.…”

mentioning

confidence: 61%

Callyspongynes A and B: New polyacetylenic lipids from a southern australian marine sponge, Callyspongia sp

Rooney

Capon

1998

Lipids

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A Callyspongia sp. collected by SCUBA off Barwon Heads, Australia, has afforded two new polyacetylenic lipids, callyspongynes A and B, the structures of which were assigned by spectroscopic analysis and chemical derivatization. Lipids 33, 639-642 (1998).Polyacetylenic lipids represent a class of natural product common to marine sponges, with many examples reported in recent years of this structure class varying in chain length, degrees of unsaturation, and biological activity (antimicrobial, antitumor, antifungal, and antiviral). Sponge genera known to feature polyacetylenic lipids include Petrosia (1-8), Cribrochalina (9-12), Tetrosia (13), Xestospongia (14,15), Siphonochalina (16), Reniera (17), Haliclona (18), and Callyspongia (19). This latter observation together with our recent experience in isolating novel lipids from a southern Australian Callyspongia sp. (20) prompted an investigation of the lipid content of another Callyspongia sp. in our collection. This report describes the results of a chemical analysis of a Callyspongia sp. collected by SCUBA at ~30 m depth off Barwon Heads (Victoria, Australia). EXPERIMENTAL PROCEDURESAll solvents were redistilled before use. Rapid silica filtrations were carried out using Kieselgel 60 silica gel loaded into a sintered glass funnel and eluted under low vacuum. Solid phase extraction was carried out using Alltech Maxiclean silica 900 mg cartridges (Alltech Corp., Deerfield, IL) attached to luer lock syringes. High-performance liquid chromatography (HPLC) was performed on an ISCO 2350 solvent delivery system (ISCO Corp., Lincoln, NE) equipped with a rheodyne injector, Waters 401 differential refractometer and Spectra Physics 200 programmable UV/VIS wavelength detector, and recorded on either Chart V3.2 data collection package using an AD Instruments Mac Lab/2E operating on an Apple Macintosh LC; or a Data Acquisition Plotting and Analysis (DAPA) package operating on an Ipex 286PC unit under DOS 5.0. Thin-layer chromatography was carried out on Machery-Nagel Duren Alugram Sil G/UV 254 plates and visualized by both short (254 nm)-and long (365 nm)-wavelength ultraviolet light, as well as spraying with 5% vanillin in H 2 SO 4 /H 2 O (50% wt/vol) and heating at 100°C for 2-5 min. Chiroptical measurements [α] D were obtained on a Jasco DIP-1000 digital polarimeter in a 100 mm × 2 mm cell. Infrared (IR) spectra were acquired on a Perkin-Elmer 1600 Fourier transform IR spectrophotometer. Nuclear magnetic resonance (NMR) experiments were performed on either a Varian Inova 400, Varian Unity 300, or a Varian Unity plus 400 spectrometer in the solvents indicated, with 1 H NMR referenced to residual solvent resonances and 13 C NMR to carbon resonances.Electrospray ionization (ESI) (1:1 acetonitrile/water matrix) mass spectra were acquired on a Micromass Quattro II mass spectrometer at the cone voltages indicated. Electron impact ionization (EI) (70 eV) mass spectra were acquired on a JEOL ax-505H mass spectrometer. High-resolution ESI (1:1 acetonitrile/water matrix) mass measure...

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“…inhibited reverse transcriptase of HIV virus (307,308). The sponge Strongylophora durissima yielded two new acetylenic derivatives, durissimols A and B (213), and duryne (214) (309-311).…”

Section: Marine and Freshwater Sponges (Porifera)mentioning

confidence: 99%

Anticancer activity of natural and synthetic acetylenic lipids

Dembitsky¹

2006

Lipids

129

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This review is a comprehensive survey of acetylenic lipids and their derivatives, obtained from living organisms, that have anticancer activity. Acetylenic metabolites belong to a class of molecules containing triple bond(s). They are found in plants, fungi, microorganisms, and marine invertebrates. Although acetylenes are common as components of terrestrial plants, fungi, and bacteria, it is only within the last 30 years that biologically active polyacetylenes having unusual structural features have been reported from plants, cyanobacteria, algae, invertebrates, and other sources. Naturally occurring aquatic acetylenes are of particular interest since many of them display important biological activities and possess antitumor, antibacterial, antimicrobial, antifouling, antifungal, pesticidal, phototoxic, HIV-inhibitory, and immunosuppressive properties. There is no doubt that they are of great interest, especially for the medicinal and/or pharmaceutical industries. This review presents structures and describes cytotoxic and anticancer activities only for more than 300 acetylenic lipids and their derivatives isolated from living organisms.

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Bioactive marine metabolites XX. Petrosynol and petrosynone, antimicrobial C30 polyacetylenes from the marine sponge sp.: Determination of the absolute configuration

Cited by 62 publications

References 5 publications

Total synthesis of polyyne natural products

Total synthesis of polyyne natural products

Callyspongynes A and B: New polyacetylenic lipids from a southern australian marine sponge, Callyspongia sp

Anticancer activity of natural and synthetic acetylenic lipids

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