Corticatic Acids A-C, Antifungal Acetylenic Acids from the Marine Sponge, Petrosia corticata

Li, Hong Yu; Matsunaga, Shigeki; Fusetani, Nobuhiro

doi:10.1021/np50112a022

Cited by 44 publications

(58 citation statements)

References 8 publications

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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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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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“…The acetylenic acid that we isolated from Fontinalis as well as other acetylenic fatty acids are common to aquatic and terrestrial mosses (Anderson et al 1975, Jamieson and Reid 1976, Kohn et al 1987, Zinsmeister et al 1991 but are uncommon in vascular plants (Seigler 1998). Some acetylenic fatty acids have antimicrobial and antifungal properties (Borel et al 1993, Li et al 1994, suggesting other potential defensive roles for this compound. Additionally, acetylenic compounds are inherently unstable when exposed to light, heat, and oxygen (Seigler 1998), perhaps explaining why our isolated yield was only 0.0036% of dry mass (by contrast, the same compound was found at 0.29% in another aquatic moss, F. antipyretica (Jamieson and Reid 1976).…”

Section: Discussionmentioning

confidence: 89%

Stream mosses as chemically-defended refugia for freshwater macroinvertebrates

Parker¹,

Burkepile²,

Collins³

et al. 2007

Oikos

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Marine and terrestrial studies show that small, sedentary herbivores that utilize plants as both food and habitat can gain enemy-free space by living on hosts that are chemically defended from larger, generalist consumers. Although large herbivores are increasingly recognized as important consumers of macrophytes in freshwater communities, the potential indirect effects of herbivory on plant-associated macroinvertebrates have rarely been studied. Here, we show that the large, generalist consumers in a riverine system, Canada geese, Branta canadensis , and crayfish, Procambarus spiculifer , both selectively consumed riverweed, Podostemum ceratophyllum , over an aquatic moss, Fontinalis novae-angliae, even though moss comprised 89% of the total plant biomass on riverine rocky shoals. Moss supported twice as many plant-associated macroinvertebrates as riverweed, suggesting that it might provide a spatial refuge from consumption by these larger consumers. Bioassay-guided fractionation of moss extracts led to the isolation of a C 18 acetylenic acid, octadeca-9,12-dien-6-ynoic acid, that deterred crayfish feeding. In contrast to results with Canada geese and crayfish, both the amphipod Crangonyx gracilis and the isopod Asellus aquaticus consumed significant amounts of moss but rejected riverweed in laboratory feeding assays. Moreover, neither amphipod nor isopod feeding was deterred by the crude organic extract of Fontinalis , suggesting that these mesograzers tolerate or circumvent the chemical defenses that deterred larger consumers. Thus, herbivory by large, generalist herbivores may drive freshwater plant community structure towards chemically defended plants and favor the ecological specialization of smaller, less mobile herbivores on unpalatable hosts that represent enemy-free space.

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“…sponge [345] and osirisynes A-F (31K-P) from Haliclona osiris have been reported [346]. The α-acetylenic carboxylic acid functionality, only seen previously in the corticaric acids [339], indicates a distinctive biogenetic route.…”

Section: Marine Fatty Acids Andmentioning

confidence: 89%

“…Corticatic acids A-C (31A-C) were reported in 1994 from Petrosia corticata (Fig. 35) [339]. 31A and the related acids D and E (31D-E) have potential as selective antifungal agents as they were found to inhibit yeast geranylgeranyltransferase type 1, which has only 30% sequence homology to the human enzyme [340].…”

Section: Marine Fatty Acids Andmentioning

confidence: 99%

Biosynthesis and function of polyacetylenes and allied natural products

Minto

Blacklock

2008

Progress in Lipid Research

286

218

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Polyacetylenic natural products are a substantial class of often unstable compounds containing a unique carbon-carbon triple bond functionality, that are intriguing for their wide variety of biochemical and ecological functions, economic potential, and surprising mode of biosynthesis. Isotopic tracer experiments between 1960 and 1990 demonstrated that the majority of these compounds are derived from fatty acid and polyketide precursors. During the past decade, research into the metabolism of polyacetylenes has swiftly advanced, driven by the cloning of the first genes responsible for polyacetylene biosynthesis in plants, moss, fungi, and actinomycetes, and the initial characterization of the gene products.The current state of knowledge of the biochemistry and molecular genetics of polyacetylenic secondary metabolic pathways will be presented together with an up-to-date survey of new terrestrial and marine natural products, their known biological activities, and a discussion of their likely metabolic origins.

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Corticatic Acids A-C, Antifungal Acetylenic Acids from the Marine Sponge, Petrosia corticata

Abstract: Three new acetylenic acids, corticatic acids A-C [1-3] have been isolated from the marine sponge, Petrosia corticata. Their structures were determined by spectroscopic methods, and 1-3 exhibited antifungal activity against Mortieralla ramanniana.

Cited by 44 publications

References 8 publications

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

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

Stream mosses as chemically-defended refugia for freshwater macroinvertebrates

Biosynthesis and function of polyacetylenes and allied natural products

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