Barceloneic Acid A, a New Farnesyl-Protein Transferase Inhibitor from a Phoma Species

Abstract

Three new diphenyl ethers, barceloneic acids A, B, and barceloneic lactone [1, 2, and 3, respectively] were isolated from a fermentation extract of a fungus of the genus Phoma. The structures of compounds 1-3 were determined by a combination of spectroscopic and single-crystal X-ray diffraction methods. The effect of these compounds on the inhibition of farnesyl-protein transferase (FPTase) was evaluated and results are presented. Barceloneic acid A [1] is a novel and modest inhibitor of FPTase with an IC50 value of 40 microM.

Antioxidative Polyketones from the Mangrove-Derived Fungus Ascomycota sp. SK2YWS-L

“…The EtOAc extract of the fermentation broth was fractionated by repeated silica gel chromatography, Sephadex LH-20 column chromatography and reversed-phase C 18 semipreparative High Performance Liquid Chromatography (HPLC) to afford the five new compounds ( 1 − 5 ) together with the three known compounds methyl 2-(2,6-dihydroxy-4-methylbenzoyl)-3-hydroxy-5-methoxybenzoate ( 6 ), 2-(2-carboxy-3-hydroxy-5-methylphenoxy)-3-hydroxy-5-methoxybenzoic acid ( 7 )12, 2-hydroxy-6-(2-hydroxy-6-(hydroxymethyl)-4-methoxyphenoxy)-4-methylbenzoic acid ( 8 ) and emodin ( 9 )13. The structures of the new compounds were deduced by spectroscopic data as well as X-ray crystallographic analysis and the identifications of the known compounds were based on the comparison of their spectroscopic data with those previously reported (Fig.…”

Diphenyl Ether Glycoside from the Stems of Ilex litseaefolia Hu et Tang

“…The first brominated diphenyl ether was isolated from sponge (Carté and Faulkner 1981). This kind of compound possesses various bioactivities such as antibacterial (Oh et al 1999), antitumor (Jayasuriya et al 1995;Fuente et al 2003;Liu et al 2004), anti-inflammatory (Wiemer et al 1991), antiviral (Rich et al 1992) and herbicidal (Hargreaves et al 2002) effects. However, ilexfoliaoside (compound 1) may not contribute any bioactivity for I. litseaefolia in view of the isolated yield.…”

Neoplaether, a new cytotoxic and antifungal endophyte metabolite fromNeoplaconema napellumIFB-E016

“…Previously, diphenyl ether derivatives sharing a framework with neoplaether have been reported as secondary metabolites of fungi belong to the genera Pestalotiopsis (Shimada et al , 2001), Xylaria (Adeboya et al , 1996), Phoma (Jayasuriya et al , 1995) and Oospora (Natori & Nishikawa, 1962). Some diphenyl ether analogs were reported to inhibit farnesyl‐protein transferase (Jayasuriya et al , 1995), endothelin binding (Ohashi et al , 1992), and vascular endothelial growth factor (VEGF)‐induced tube formation of human umbilical vein endothelial cells (HUVECs) (Jung et al , 2002). To add a new member to the existing bioactive diphenyl ether, we have reported herewith the structure of neoplaether along with its cytotoxicity against the human nasopharynyeal epidermoid tumor KB cell line, with its IC 50 value (13.0 μg mL −1 ) comparable to that (2.5 μg mL −1 ) of 5‐fluorouracil co‐assayed as a reference material.…”