Highly oxidized cuparene-type sesquiterpenes from a mycelial culture of Flammulina velutipes

Ishikawa, Noemia Kazue; Yamaji, Keiko; Tahara, Satoshi; Fukushi, Yukiharu; Takahashi, K.

doi:10.1016/s0031-9422(00)00189-8

Cited by 64 publications

(50 citation statements)

References 13 publications

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“…-The fungus Flammulina velutipes (Curtis) Singer, belonging to the family Tricolomataceae (Hymenomycetes, Basidiomycota), is an edible mushroom often consumed in China and Japan. Previous chemical investigations of the fruiting body and mycelial culture of this fungus have revealed bioactive compounds with various chemical structures and interesting medicinal properties, including polysaccharides with immunomodulatory activity [1], proteins with antiviral and immunomodulatory activity [2], lectins with antitumor activity [3], sterols [4], monoterpenetriols [5], and sesquiterpenes with antimicrobial activity [6] [7]. To further exploit the potential of F. velutipes in producing bioactive natural products, the solid culture of F. velutipes was chemically investigated.…”

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confidence: 99%

Four New Cuparene‐Type Sesquiterpenes from Flammulina velutipes

Wang

Yang

et al. 2012

Helvetica Chimica Acta

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Flamvelutpenoids A -D (1 -4), four new cuparene-type sesquiterpenes, were isolated from the solid culture of Flammulina velutipes. Their structures were elucidated by NMR experiments. The absolute configurations of 1 and 2 were assigned via the circular dichroism data of the [Rh 2 (OCOCF 3 ) 4 ] complex, whereas that of C(3) of 3 was determined by applying the octant rule for the a,b-unsaturated ketone moiety. Compounds 1 -4 showed weak antibacterial activity against Escherichia coli, Bacillus subtilis, and methicillin-resistant Staphylococcus aureus with MIC values larger than 100 mm.Introduction. . To further exploit the potential of F. velutipes in producing bioactive natural products, the solid culture of F. velutipes was chemically investigated. Herein, we report the isolation and characterization of the four new cuparene-type sesquiterpenes 1 -4 from F. velutipes (Fig. 1). Their antibacterial activity against Escherichia coli, Bacillus subtilis, and methicillinresistant Staphylococcus aureus was also evaluated.

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confidence: 99%

Four New Cuparene‐Type Sesquiterpenes from Flammulina velutipes

Wang

Yang

et al. 2012

Helvetica Chimica Acta

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“…We reported previously that enokipodins A and C were autoxidized to enokipodins B and D on silica gel thin-layer plates, via the keto-type tautomers illustrated as 5 and 6, respectively, which has not yet been detected (see Fig. 1) (Ishikawa et al 2000. A small part of enokipodin A was oxidized to yield enokipodin B (0.0026 mg/ml culture filtrate on day 55).…”

Section: Time-course Of Enokipodins A-d Productionmentioning

confidence: 87%

“…We have isolated the sesquiterpenoids, enokipodins A-D ( Fig. 1), from the 30-45 days culture filtrates as the major antimicrobial metabolites and elucidated their structures (Ishikawa 2001;Ishikawa et al 2000Ishikawa et al , 2001. Here we report the production time-course, minimum inhibitory doses (MIDs), and antimicrobial spectra of enokipodins A-D and the variability in production of those compounds among ten isolates of F. velutipes tested.…”

Section: Introductionmentioning

confidence: 91%

Production of enokipodins A, B, C, and D: a new group of antimicrobial metabolites from mycelial culture of Flammulina velutipes

et al. 2005

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Antimicrobial compounds enokipodins A, B, C, and D were originally isolated from the culture filtrates of Flammulina velutipes mycelial culture. Analysis of antibacterial activity by the paper disk method and quantification of enokipodins A-D by high performance liquid chromatography (HPLC) showed that F. velutipes mycelia produced enokipodins A-D in their late growing phase. Great genetic variability in production of these compounds was observed among ten strains of F. velutipes in analyses of antimicrobial activity by the hole-plate diffusion method and quantification by HPLC. Enokipodins A-D demonstrated antimicrobial activity mainly against the grampositive bacteria Bacillus subtilis and Staphylococcus aureus. Evaluation of minimum inhibitory doses (MIDs) showed that MIDs of enokipodins A and C for B. subtilis were as low as that of the penicillin G antibiotic.

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“…Many studies have long reported the characteristics, nutritional components and biological activities of F. velutipes. [1][2][3][4][5][6][7][8][9] F. velutipes is rich in macromolecules such as proteins, polysaccharides, and glycoproteins with its associated medicinal qualities such as its antivirus, antitumor, and immunomodulatory activity. 4,10 In recent times even though some simple biological molecules including sterols, fatty acids, flavonoids, nucleosides, and polyol have been found in F. velutipes, 11 the antitumor activities of these substances have been scarcely reported.…”

Section: Introductionmentioning

confidence: 99%

Enhanced oral bioavailability of a sterol-loaded microemulsion formulation of Flammulina velutipes, a potential antitumor drug

Yi¹,

Zhong²,

Tong³

et al. 2012

IJN

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Purpose:To investigate the growth inhibition activity of Flammulina velutipes sterol (FVS) against certain human cancer cell lines (gastric SGC and colon LoVo) and to evaluate the optimum microemulsion prescription, as well as the pharmacokinetics of encapsulated FVS. Methods: Molecules present in the FVS isolate were identified by gas chromatography/mass spectrometry analysis. The cell viability of FVS was assessed with methyl thiazolyl tetrazolium (MTT) bioassay. Based on the solubility study, phase diagram and stability tests, the optimum prescription of F. velutipes sterol microemulsions (FVSMs) were determined, followed by FVSMs characterization, and its in vivo pharmacokinetic study in rats. ). The optimal FVSMs prescription consisted of 3.0% medium chain triglycerides, 5.0% ethanol, 21.0% Cremophor EL and 71.0% water (w/w) with associated solubility of FVS being 0.680 mg ⋅ mL −1 as compared to free FVS (0.67 µg ⋅ mL −1 ). The relative oral bioavailability (area-under-the-curve values of ergosterol and 22,23-dihydroergosterol showed a 2.56-fold and 4.50-fold increase, respectively) of FVSMs (mean diameter ∼ 22.9 nm) as against free FVS were greatly enhanced. Our laboratory has been able to screen out lipid soluble sterols with an antitumor effect from F. velutipes by lipidraft chromatography, which was found to be linked to the tyrosine kinase receptor (data not published). In this study, our laboratory was interested in performing a preliminary investigation of the anticancer potential and bioavailability of F. velutipes sterol (FVS) as an in-depth contribution to the research of F. velutipes. FVS is a white powder, which can easily dissolve in ether, chloroform, hot ethanol, and other organic solvents, but barely dissolves in water. As a result, it is necessary to find a method to improve the solubility and oral bioavailability of this sterol. Dovepress 5067 O R I G I N A L R E S E A R C HMicroemulsions are thermodynamically stable nanometer systems with characteristics of easy preparation, small droplet size, low viscosity, and strong solubilization effect. 12It is formed spontaneously by water, oil, surfactant and cosurfactant. 13,14 According to the structure of a microemulsion, it can be divided into water-in-oil (w/o), oil-in-water (o/w) and bicontinuous microemulsion. 15 As a drug carrier, a microemulsion can increase the solubility and oral bioavailability of poorly soluble drugs, ameliorate the localization, improve systemic delivery of the drug, and possess the ability of targeting drug release. [16][17][18] The absolute bioavailability of a poorly soluble drug cyclosporin A which was loaded into a microemulsion system was increased to about 3.3-and 1.25-fold compared with free Sandimmun and Sandimmun Neoral (Novartis, Basel, Switzerland), which were used as commercial cyclosporin A. 19 In addition, it has been confirmed that the microemulsion system containing the poorly soluble drug docetaxel could improve the solubilization property and oral bioavailability of the drug. 20 Presently, there a...

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Highly oxidized cuparene-type sesquiterpenes from a mycelial culture of Flammulina velutipes

Cited by 64 publications

References 13 publications

Four New Cuparene‐Type Sesquiterpenes from Flammulina velutipes

Four New Cuparene‐Type Sesquiterpenes from Flammulina velutipes

Production of enokipodins A, B, C, and D: a new group of antimicrobial metabolites from mycelial culture of Flammulina velutipes

Enhanced oral bioavailability of a sterol-loaded microemulsion formulation of Flammulina velutipes, a potential antitumor drug

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