Aldehyde Dehydrogenase Inhibitors from the Mushroom Clitocybe clavipes

Kawagishi, Hirokazu; Miyazawa, Toshiyuki; Kume, Hiroko; Arimoto, Yasushi; Inakuma, Takahiro

doi:10.1021/np020200j

Cited by 33 publications

(29 citation statements)

References 13 publications

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“…In a search in different data bases, i. e. AntiBase [34], the Dictionary of Natural Products (DNP) [39] and Chemical Abstract, only 8-oxo-9-octadecenoic acid (1c) was revealed. However, comparison of the spectroscopic data with the literature [25] showed clear differences.…”

Section: (E)-11-oxo-octadeca-12-enoic Acid (1a)mentioning

confidence: 65%

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Three New Unsaturated Fatty Acids from the Marine Green Alga Ulva fasciata Delile

Abou-El-Wafa¹,

Shaaban²,

Shaaban³

et al. 2009

Zeitschrift Für Naturforschung B

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From the dichloromethane extract of the marine green alga Ulva fasciata Delile, collected from the Mediterranean coast of Egypt, three new fatty acids, namely, (E)-11-oxo-octadeca-12-enoic acid (1a), (E)-11-hydroxy-octadeca-12-enoic acid (2a) and 6-hydroxy-oct-7-enoic acid (3a) together with cholesterol were isolated. Analysis of the unpolar part of the extract using GC-MS detected the existence of further ten compounds, namely, dimethylsulfoxide, dimethylsulfone, phenylacetamide, 6,10,14-trimethyl-pentadecan-2-one, 8-heptadecene, dodecane, tridecane, 4-oxo-pentanoic acid, hexadecanoic acid, and the naturally new 1,1 -bicyclohexyl. Structures of the isolated compounds 1a -3a were confirmed by spectroscopic analyses including mass spectra (EI-MS, HR/ESI-MS), 1D and 2D NMR experiments, and by the synthetic conversion into their corresponding methyl esters 1b -3b. The algal extract and its components were comparatively examined against several pathogenic microorganisms, and brine shrimps for cytotoxicity.

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Section: (E)-11-oxo-octadeca-12-enoic Acid (1a)mentioning

confidence: 65%

“…Both the fatty acid 1a and the ester 1b are reported here for the first time. α,β -Enones are highly cytotoxic and play vital roles as aldehyde dehydrogenase inhibitors [25].…”

Section: (E)-11-oxo-octadeca-12-enoic Acid (1a)mentioning

confidence: 99%

Three New Unsaturated Fatty Acids from the Marine Green Alga Ulva fasciata Delile

Abou-El-Wafa¹,

Shaaban²,

Shaaban³

et al. 2009

Zeitschrift Für Naturforschung B

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“…Kawagishi et al,9) showed that some conjugated ketonic fatty acid analogues have relatively potent inhibitory activity against aldehyde dehydrogenase in cell-free conditions. We therefore tried to assess the cytotoxic activity of compound 1 in both cultured human myeloma THP-1 cells and murine melanoma B16F1 cells.…”

Section: Resultsmentioning

confidence: 99%

Cytotoxic Fatty Acid from Pleurocybella porrigens

Hasegawa

Ishibashi

Takata

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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The fungus Pleurocybella porrigens (called 'sugihiratake' in Japanese), which is a basidiomycete of the Trichoromataceae family, is a lignicolous agaric mushroom that produces pure white, relatively small pleurotoid fruiting bodies on rotting conifers, often in abundance.1) This edible mushroom grows during the late summer and autumn and is native to all districts of Japan, including the Tohoku and Hokuriku areas. P. porrigens was suspected to cause acute encephalopathy including coma and spasm in the Tohoku and Hokuriku areas in 2004.2-4) We have recently reported that an intraperitoneal administration of a hot water extract of P. porrigens caused acute toxic death with hemorrhagic anemia in mice within 24 h, and the toxicant was in part a thermolabile high molecule contained in this mushroom. 5) However, the toxic constituents responsible for patients with critical encephalopathy and nephrosis have not yet been clarified. In this study, we therefore isolated the toxic constituents from P. porrigens, and report here the isolation and structural elucidation of a new ketonic fatty acid conjugated with porrigenic acid (1) and its cytotoxic activity. Results and DiscussionThe MeOH extract of P. porrigens (2.5 kg fresh weight) was partitioned between EtOAc and H 2 O, and the EtOAc layer was subjected to bioassay-guided fractionation with repeated flash column chromatography on silica gel and ODS and further purified by HPLC equipped with an ODS column to afford new compound 1.Compound 1 was obtained as a colorless solid, and its molecular formula, C 18 H 30 O 4 , was established from HR-FAB-MS, which gave a pseudomolecular ion peak at m/z 311.2214 [MϩH] ϩ . The 13 C-NMR, DEPT, and HMQC spectra (Table 1) of 1 showed signals of one methyl, 10 methylenes, five methines, and two quaternary carbons including a carboxylic acid (d 177.9, C-1) and a ketone (d 203.7, C-9), respectively. The presence of two conjugated E,E-form enone systems was revealed by the 1 H-NMR spectrum ( . Furthermore, the UV spectrum of 1 displayed a l max at 273 nm.6) The 1 H-NMR spectrum (Table 1) showed signals at 0.92 (3H), 1.33 (10H), and 1.59 (6H) ppm, which can be attributed to the terminal methyl to methylene groups of aliphatic chains. HMBC correlations were observed at H-2/C-1, C-3, C-4; H-8/C-6, C-7, C-9, C-10; H-10/C-9; H-11/C-9; H-17/C-15, C-16, C-18; and H-18/C-16, C-17. Further analysis of EI-MS data indicated that notable fragment ion peaks were observed at m/z 57, 87, 139, and 167. The locations of a carbonyl carbon (d 203.7) at C-9 and an oxygenated methine carbon (d 72.6) at C-14 were identified from the HMBC spectrum and EI-MS analysis (Fig. 2). Based on the above data, compound 1 was determined to be (10E,12E)-14-hydroxy-9-oxo-10,12-octadecadienoic acid. A racemic mixture of 1 was isolated from the same mushroom by Amakura et al. The new conjugated ketonic fatty acid, porrigenic acid (1), was isolated as a cytotoxic constituent of Pleurocybella porrigens. The structure of 1 was elucidated using spectroscopic methods including...

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“…Among clitocyboid taxa, A. clavipes (Pers.) Redhead, Lutzoni, Moncalvo & Vilgalys is uniquely characterized by the formation of coprine-like compounds (fatty acid relatives acting as in vitro aldehyde dehydrogenase inhibitors and inducing an antabuse-like syndrome, Kawagishi et al 2002) and, ultrastructurally, by the minutely roughened basidiospores (in contrast to the smooth-spored Clitocybe or echinate-spored Lepista). A. clavipes also produces a new class of tyrosine kinase (Cassinelli et al 2000); (2) Cantharocybe H.E.…”

Section: Discussionmentioning

confidence: 99%

Trichocybe, a new genus for Clitocybe puberula (Agaricomycetes, Agaricales)

2010

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Trichocybe, a new genus of Agaricales, is described to accommodate the rare species Clitocybe puberula characterized by an isolated phylogenetic position. Trichocybe is distinguished from its allied clitocyboid genera by a unique combination of macro-and micromorphological characters, including a Gymnopus-like habitus, a pubescent pileus with squamulose flocci, an eccentric stipe growing on wood debris, a putrescent non-reviviscent context, a strongly farinaceous odour, rare but clearlydifferentiated cheilocystidia, an unusual, strongly differentiated pileipellis, a subpellis with vesiculose-physaloid elements, a stipitipellis with diverticulate hyphae, and smooth, acyanophilous, inamyloid basidiospores. Trichocybe is so far known only from northwestern Europe. Based on a LSU-and 5.8S-rDNA Bayesian phylogenetic analysis, Trichocybe clusters within the Tricholomatoid clade, where it occupies an isolate position. Furthermore, according to the present analysis, also Clitocybe phaeophthalma seems to represent an independent evolutive line in the clitocyboid fungi, which suggests adopting the genus Singerocybe Harmaja for this taxon as well as similar ones.

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Aldehyde Dehydrogenase Inhibitors from the Mushroom Clitocybe clavipes

Abstract: Five fatty acid derivatives including three novel compounds were isolated from the mushroom Clitocybe clavipe. Their structures were elucidated by spectral analyses. These compounds inhibited aldehyde dehydrogenase in vitro.

Cited by 33 publications

References 13 publications

Three New Unsaturated Fatty Acids from the Marine Green Alga Ulva fasciata Delile

Three New Unsaturated Fatty Acids from the Marine Green Alga Ulva fasciata Delile

Cytotoxic Fatty Acid from Pleurocybella porrigens

Trichocybe, a new genus for Clitocybe puberula (Agaricomycetes, Agaricales)

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