Vibralactone: A Lipase Inhibitor with an Unusual Fused β‐Lactone Produced by Cultures of the Basidiomycete Boreostereum vibrans.

Liu, Dong‐Ze; Wang, Fei; Liao, Tou‐Gen; Tang, Jie; Steglich, Wölfgang; Zhu, Hua‐Jie; Liu, Ji‐Kai

doi:10.1002/chin.200716214

Cited by 25 publications

(32 citation statements)

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“…[13][14][15] This value is very close to the observed value of À17.51, which strongly suggests that the eight stereogenic centers in 1 were 1R, 2S, 3R, 4R, 5S, 6R, 14R and 15R.…”

Section: Resultssupporting

confidence: 71%

Velleratretraol, an unusual highly functionalized lactarane sesquiterpene from Lactarius vellereus

et al. 2009

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An unusual highly functionalized lactarane sesquiterpene, named velleratretraol (1), was isolated from the ethanol extract of the fruiting body of the mushroom Lactarius vellereus. Its structure was determined through spectroscopic analysis and singlecrystal X-ray diffraction studies. The proposed assignment of the absolute configuration is based on computational results. It showed weak activity against HIV-1 cells with an effective concentration of 68.0 mg ml À1 and a selectivity index of 2.0. The Journal of Antibiotics (2009) 62, 129-132; doi:10.1038/ja.2008; published online 23 January 2009Keywords: lactarane sesquiterpene; Lactarius vellereus; velleratretraol; X-ray INTRODUCTIONThe Russulaceae family is one of the largest in the subdivision Basidiomycotina in Whittaker's Kingdom of Fungi and comprises hundreds of species. 1 Sesquiterpenes play an important biological role in a majority of the Lactarius species. They are responsible for the pungent and bitter taste of the milky juice, the color change in the latex upon air exposure, 2 and they constitute a chemical defense system against intruders such as bacteria, fungi, animals and insects. 3 The fungal subdivision Basidiomycotina produces many toxic sesquiterpenes derived from the protoilludane skeleton. This skeleton is transformed and rearranged into a multitude of compounds. Fungal sesquiterpenes formed via the humulane-protoilludane biosynthetic pathway are characteristic for the subdivision Basidiomycotina. The largest group of sesquiterpenes, belonging to the classes of lactaranes, secolactaranes, marasmanes, isolactaranes, norlactaranes and caryophyllanes, are believed to be biosynthesized from humulane. 4 Fungi of the genus Lactarius have been shown to be a good source of bioactive secondary metabolites. [5][6][7] China is extraordinarily rich in higher fungi, with over 6000 species reported to belong to about 1200 genera. In our on-going research to explore the biologically active natural products of the higher fungi of China, [8][9][10][11][12] the chemical constituents of the fruiting bodies of Lactarius vellereus were investigated. This report describes the isolation and structure elucidation of an unusual highly functionalized lactarane sesquiterpene, named velleratretraol (1), and its anti-HIV activity. (d, 35.9) by analysis of the DEPT spectra. An analysis of the 1 H-NMR spectrum indicated the presence of three methyl groups at d¼1.03 (s), 1.12 (s) and 1.27 (s). The first two resonances were ascribed to geminal methyl groups, and the third one was ascribed to the methyl group on the carbon atom bearing the tetramethylene oxide carbocycle group. In particular, a doublet occurring at d¼3.73 (d, 11.8) was attributed to the C-4 bearing a secondary OH group, and two resonances at d¼5.55 (s) and 5.35 (s) were assigned at C-14 and C-15, respectively. Its formula indicated a sesquiterpene skeleton containing 4 degrees of unsaturation. The structure was suggested to be a tetracyclic sesquiterpene. RESULTS AND DISCUSSIONThe key connectivity of the pr...

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“…[13][14][15] This value is very close to the observed value of À17.51, which strongly suggests that the eight stereogenic centers in 1 were 1R, 2S, 3R, 4R, 5S, 6R, 14R and 15R.…”

Section: Resultssupporting

confidence: 71%

Velleratretraol, an unusual highly functionalized lactarane sesquiterpene from Lactarius vellereus

et al. 2009

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“…Microbial compounds like Vibralactone 22 and Percyquinin 23 have exhibited better IC 50 values as compared to their crude extracts.…”

Section: Discussionmentioning

confidence: 99%

Potential pancreatic lipase inhibitory activity of an endophyticPenicilliumspecies

Gupta

Saxena

Goyal

2014

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…In vitro it inhibits pancreatic lipase with an IC 50 of 0.4 μg/mL. 133 Studies in animal models are required to test vibralactone's effectiveness and possible undesirable effects.…”

Section: Ebelactonesmentioning

confidence: 99%

The role of lipid and carbohydrate digestive enzyme inhibitors in the management of obesity: a review of current and emerging therapeutic agents

Tucci¹

2010

DMSO

117

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Vibralactone: A Lipase Inhibitor with an Unusual Fused β‐Lactone Produced by Cultures of the Basidiomycete Boreostereum vibrans.

Abstract: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Cited by 25 publications

References 1 publication

Velleratretraol, an unusual highly functionalized lactarane sesquiterpene from Lactarius vellereus

Velleratretraol, an unusual highly functionalized lactarane sesquiterpene from Lactarius vellereus

Potential pancreatic lipase inhibitory activity of an endophyticPenicilliumspecies

The role of lipid and carbohydrate digestive enzyme inhibitors in the management of obesity: a review of current and emerging therapeutic agents

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