Azaphilone Derivatives Research Articles

ChemInform Abstract: New Brominated and Halogen-Less Derivatives and Structure-Activity Relationship of Azaphilones Inhibiting gp120-CD4 Binding.

Novel brominated and halogen-less azaphilone (oxoisochromane) derivatives, 5-bromoochrephilone and dechloroisochromophilone IV, and known derivatives, dechloroisochromophilone III and isorotiorin, were isolated from the culture broth of a producing organism of isochromophilones I and II (azaphilones inhibiting gp120-CD4 binding), Penicillium multicolor FO-2338, fermented in a medium containing potassium bromide. Nineteen azaphilone-related compounds isolated from the above strain and from other fungi were tested for the inhibition of gp120-CD4 binding and the structure-activity relationship is discussed. Consequently, 5-bromoochrephilone is the strongest inhibitor (IC50, 2.5 microM). A halogen atom at C-5, a proton at C-8 and a diene structure in C-3 side chain of 6-oxoisochromane ring are necessary for gp120-CD4 binding.

Azaphilone and Isocoumarin Derivatives from the Endophytic Fungus Penicillium sclerotiorum PSU-A13

Two new azaphilone derivatives, penicilazaphilones A (1) and B (2), and one new isocoumarin, penicilisorin (3), together with six known compounds were isolated from the endophytic fungus Penicillium sclerotiorum PSU-A13. Their structures were identified by analysis of spectroscopic data. The antimicrobial activity against Staphylococcus aureus, Candida albicans and Cryptococcus neoformans as well as the inhibitory effect on human immunodeficiency virus (HIV)-1 integrase and protease were examined.

Antifungal Metabolites from the Plant Endophytic Fungus Pestalotiopsis foedan

Pestafolide A ( 1), a new reduced spiro azaphilone derivative, and pestaphthalides A ( 2) and B ( 3), two new isobenzofuranones, have been isolated form solid cultures of an isolate of Pestalotiopsis foedan. The structures of these compounds were determined mainly by analysis of their NMR spectroscopic data. The relative configuration of 1- 3 was assigned by analysis of (1)H NMR J-values and NOESY data, and the absolute configuration was determined by application of the CD excitation chirality and modified Mosher method. Compounds 1- 3 showed modest antifungal activity.

New azaphilones from the inedible mushroom Hypoxylon rubiginosum.

Fractionation of the methanol extract of the fruit bodies of the xylariaceus ascomycete Hypoxylon rubiginosum resulted in the isolation of three new azaphilone derivatives named rubiginosins A-C (1-3) and a new fatty acid named rubiginosic acid (4), together with three known compounds, entonaemin A (5), daldinin C (6), and orsellinic acid. Their structures were elucidated by 2D NMR, MS, IR, and UV spectra and chemical reaction. The absolute configuration of compound 3 was established by CD spectroscopy. The structure of 4 was confirmed by X-ray crystallographic analysis.

Cyclic Azaphilones Daldinins E and F from the Ascomycete Fungus Hypoxylon fuscum (Xylariaceae)

AbstractFor Abstract see ChemInform Abstract in Full Text.

Cyclic azaphilones daldinins E and F from the ascomycete fungus Hypoxylon fuscum (Xylariaceae)

Phytochemical examination of the methanolic extract of fruit bodies of the Xylariaceous ascomycete fungus Hypoxylon fuscum led to the isolation of two azaphilone derivatives named daldinins E and F together with two known compounds daldinin C and 4,5,4′,5′-tetrahydroxy-1:1′-binaphthyl using a combination of reversed phase HPLC and high performance gel permeation chromatography. Their structures were determined by 2D NMR, MS, IR, UV, and CD spectroscopy. Their antioxidative activities were also estimated by an indication of a 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging effect. The chemosystematics of Hypoxylon is discussed.

A novel alkaloid serantrypinone and the spiro azaphilone daldinin D from Penicillium thymicola.

The novel quinazoline metabolite serantrypinone (1) has been isolated from an isolate of the microfungus Penicillium thymicola together with daldinin D (2), a new peracetylated spiro azaphilone derivative. The structures of 1 and 2 were elucidated by analysis of spectroscopic data, including 2D NMR, and comparison with literature data.

Hydrogenated azaphilones from Emericella falconensis and E. fruticulosa

Six new hydrogenated azaphilones designated falconensins IN, and a new azaphilone, monomethyldihydromitorubrin, were isolated as minor components from mycelia of Emericella falconensis and/or E. fruticulosa along with nine azaphilone derivatives, falconensins AH and monomethylmitorubrin, and three hopane-type triterpenes. The structures of falconensins IN and monomethylmihydromitorubrin were confirmed by spectroscopic investigation and chemical correlation.

Hydrogenated azaphilones from emericella falconensis and E. Fruticulosa

Six new hydrogenated azaphilones designated falconensins IN, and a new azaphilone, monomethyldihydromitorubrin, were isolated as minor components from mycelia of Emericella falconensis and/or E. fruticulosa along with nine azaphilone derivatives, falconensins AH and monomethylmitorubrin, and three hopane-type triterpenes. The structures of falconensins IN and monomethylmihydromitorubrin were confirmed by spectroscopic investigation and chemical correlation.

Structures of a new type of yellow pigments, falconensones A and B, from Emericella falconensis

N. Ogasawara, R. Mizuno and K. Kawai, J. Chem. Soc., Perkin Trans. 1, 1997, 2527 DOI: 10.1039/A701277B

Isolation and Structures of New Azaphilone Derivatives, Falconensins E-G, from Emericella falconensis and Absolute Configurations of Falconensins A-G.

Three new azaphilone derivatives designated falconensins E5 (5), F (6), and G (7) were isolated from the mycelium o Emericella falconensis, along with falconensins A (1), B (2), C (3), D (4), and H (8), and three hopane-type triterpenes, zeorin (9), hepane-7β, 22-diol (10), and hopane-6α, 7β, 22-triol (11). The structures of 5-7 were confirmed by spectroscopic investigation and chemical correlations. The absolute stereochemistry of falconensins A (1) to G(7) was also established.

An azaphilone from Talaromyces tardifaciens

A new azaphilone derivative, monomethyl-(+)-mitorubrin, was isolated from the ascomata of Talaromyces tardifaciens. The structure was determined on the basis of spectroscopic investigations.

Structures of Daldinins A-C, Three Novel Azaphilone Derivatives from Ascomycetous Fungus Daldinia concentrica.

Three novel azaphilone derivatives, daldinins A∼C, have been isolated from the fungus (Ascomycetes) Daldinia concentrica. Their structures including the absolute configuration have been established by a combination of high resolution NMR and CD spectra, X-ray crystallographic analysis, and chemical degradation.

Azaphilones inhibit tumor promotion by 12-O-tetradecanoylphorbol-13-acetate in two-stage carcinogenesis in mice.

Monascorubrin (an azaphilone derivative) was isolated from Monascus anka, 'Monascus pigment', a natural pigment of food additivies, was extracted from Monasucs spp., and chaetoviridin A, one of the azaphilones, was isolated from Chaetomium globosum var. flavo-viridae. Application of 1 microgram of 12-O-tetradecanoylphorbol-13-acetate (TPA), a tumor promoting agent, to the mouse ear resulted in induction of inflammation. Among monascorubrin and related compounds assayed, monascorubrin, chaetoviridin A and its related compounds inhibited the inflammatory activity of TPA in mice. The 50% inhibitory dose of these compounds for TPA-induced inflammation was 0.4-1.5 mumol. Furthermore, monascorubrin (2 mumol), chaetoviridin A (2 mumol) and Monascus pigment (1 mg) markedly suppressed the promoting effect of TPA (1 microgram) on skin tumor formation in mice initiated with 7,12-dimethylbenz[a]anthracene (50 micrograms). It is assumed that the inhibition of tumor promotion by monascorubrin, chaetoviridin A and Monascus pigment is due to anti-inflammatory activity.

A New Azaphilone, Falconensin H, from Emericella falconensis.

A new azaphilone derivative, falconensin H (6), was isolated from mycelia of Emericella falconensis, together with previously reported falconensins A-D (1-4) and 3, 3'-dihydroxy-5, 5'-dimethyldiphenyl ether (5). The structure of 6 was elucidated by spectroscopic investigation and chemical correlations. Among the compounds isolated, only 5 showed antibacterial activity.