Two new pyrrolosesquiterpenes produced by a Streptomyces species.

Two new pyrrolosesquiterpenes, 1 and 2, were isolated from cultures of the soil actinomycete Streptomyces sp. Hd7-21. The structures of these compounds were established as (2Z,4E,9E)-6,7,11-trihydroxy-3,7,11-trimethyl-1-(1H-pyrrol-2-yl)dodeca-2,4,9-trien-1-one (1) and (2Z,4E)-5-{3-[(2E)-4-hydroxy-4-methylpent-2-en-1-yl]-3-methyloxiran-2-yl}-3-methyl-1-(1H-pyrrol-2-yl)penta-2,4-dien-1-one (2) by extensive spectroscopic analyses including MS, and 1D- and 2D-NMR data. Their cytotoxic activities against a panel of human cancer cell lines were evaluated.

Induced production of new diterpenoids in the fungus Penicillium funiculosum.

The supplementation of a DNA methyltransferase inhibitor, 5-azacytidine (5-AZ), to the culture medium of Penicillium funiculosum, dramatically altered its metabolic profiles. Analysis of the culture broth extract led to the isolation of two new prenyleudesmane diterpenoids (1-2). The isolated compounds were further evaluated for their cytotoxic and antibacterial activities. Our findings confirmed that the use of chemical epigenetic modifiers is an effective technique for promoting the expression of silent biosynthetic pathways to produce unique secondary metabolites.

New triterpenoids from the fruiting bodies of Ganoderma lucidum and their bioactivities.

Phytochemical investigation of the AcOEt extract of G. Lucidum has led to the isolation of two new triterpenoids, 1 and 2, together with five known ones, 3-7. The structures of the new compounds were identified as 12ß-acetoxy-3ß,7ß-dihydroxy-11,15,23-trioxolanost-8-en-26-oic acid butyl ester (1) and 12ß-acetoxy-3,7,11,15,23-pentaoxolanost-8-en-26-oic acid butyl ester (2) on the basis of detailed spectroscopic analysis (mass spectrometry, and 1D- and 2D-NMR experiments). The antimicrobial activities of 1 and 2 were also evaluated.

Epigenetic modifier-induced biosynthesis of novel acetylenic sterols from Cladosporium colocasiae.

The addition of an HDAC inhibitor, suberoylanilide hydroxamic acid (SBHA), to the culture medium of Cladosporium colocasiae, dramatically altered its metabolic profiles. Analysis of the culture broth extract led to the isolation of two new acetylenic sterols (1-2). The isolated compounds were further evaluated for their cytotoxic and antibacterial activities. Compound 1 showed activity against Bacillus subtilis, affording a zone of inhibition of 12mm at 100µg/disk. However, none of them showed noticeable growth inhibitory effects.

Two new alkaloids from the edible macrofungus Ramaria madagascariensis.

Phytochemical investigation of the ethyl acetate extract of the edible macrofungus, Ramaria madagascariensis, has led to the isolation of two new alkaloids (1 and 2). Their structures were elucidated by HR-ESI-MS, IR, and 1D- and 2D-NMR experiments. The antimicrobial activity of 1 and 2 was also tested and evaluated.

A new ergostane triterpenoid from a solid culture of the basidiomycete Inocybe lilacina.

A new and rare ergostane triterpenoid, 4alpha-methyl-3alpha,4beta-dihydroxy-ergost-8,24(28)-dien-7,11-dion-25-al (1), was isolated from cultures of the basidiomycete Inocybe lilacina, and its structure established on the basis of spectral methods (MS, IR, 1D and 2D NMR).

A new ergostane triterpenoid from cultures of the basidiomycete Inocybe lilacina.

A new ergostane triterpenoid (4 alpha-methylergost-8,24(28)-dien-3,7,1 1-trione, 1) together with four known compounds (2-5) were isolated from cultures of the spectroscopic and M Sexperiments. basidiomycete Inocybe lilacina. The structure of the new compound was established on the basis of IR, 1D and 2D NMR

A review of ergostane and cucurbitane triterpenoids of mushroom origin.

Ergostane and cucurbitane triterpenoids are relatively rare in mushroom metabolites, and a total of 55 compounds are reported up to May 2013. Many of them exhibited diverse biological properties such as anti-inflammatory, cytotoxic and antioxidative activities. The paper reviewed systematically the isolation, structure elucidation and biological activities of ergostane- and cucurbitane-type triterpenoids from mushroom for the first time.

A new pyrrolosesquiterpene isolated from cultures of Streptomyces sp.

One new pyrrolosesquiterpene 1 was isolated from the cultures of the soil actinomycete Streptomyces sp. Hd7-21. Its structure was elucidated by extensive spectroscopic analyses including MS and one-dimensional and two-dimensional NMR data. Compound 1 showed moderate cytotoxic activity against a panel of human cancer cell lines.

Structural elucidation and NMR assignments of two new pyrrolosesquiterpenes from Streptomyces sp. Hd7-21.

Two new pyrrolosesquiterpenes were isolated from cultures of the soil actinomycete Streptomyces sp. Hd7-21. The structures of these compounds were elucidated by extensive spectroscopic analyses including MS and 1D and 2D NMR data. Their cytotoxic activity against a panel of human cancer cell lines were biologically evaluated.

Two new chamigrane metabolites from fermentation broth of Steccherinum ochraceum.

Two new chamigrane-type metabolites named steperoxides C (1) and D (2) were isolated from the basidiomycetes Steccherinum ochraceum. The structures of 1 and 2 were established on the basis of spectral methods (MS, IR, ID and 2D NMR experiments). Compounds 2 showed significant antimicrobial activity against Staphylococcus aureus at 10 and 5 µg/disk.

Sesquiterpenes from cultures of the basidiomycete Conocybe siliginea.

Six new tremulane sesquiterpenes, conocenol A-D (2-5), conocenolide A (6), and conocenolide B (7), have been isolated from cultures of the basidiomycete Conocybe siliginea. The structures of 2-7 were elucidated by the analysis of spectroscopic data, including heteronuclear multiple-bond correlation, heteronuclear single-quantum coherence, and (1)H,(1)H correlation spectroscopy, and a comparison with known analogues.

A new cadinane sesquiterpene with significant anti-HIV-1 activity from the cultures of the basidiomycete Tyromyces chioneus.

A new cadinane sesquiterpene (4beta,14-dihydroxy-6alpha,7betaH-1(10)-cadinene, 1) was isolated from the cultures of the basidiomycete, Tyromyces chioneus. Its structure was established on the basis of spectral measurements (MS, IR, 1D and 2D NMR experiments). 1 showed significant anti-HIV-1 activity with EC50=3.0 microg/ml (SI=25.4).

Vibralactone: a lipase inhibitor with an unusual fused beta-lactone produced by cultures of the basidiomycete Boreostereum vibrans.

The structure and absolute configuration of vibralactone (1) from the cultures of the Basidiomycete Boreostereum vibrans were established by spectroscopic methods and computational methods. Vibralactone, an unusual fused beta-lactone-type metabolite, was found to inhibit pancreatic lipase with an IC50 of 0.4 microg/mL. [structure: see text]