Absolute stereochemistry of pentacecilides, new inhibitors of lipid droplet formation in mouse macrophages, produced by Penicillium cecidicola FKI-3765-1

Abstract

The structure of a new pentacecilide congener, pentacecilide D, produced by Penicillium cecidicola FKI-3765-1 was elucidated by various NMR experiments. The absolute stereochemistry of pentacecilides was elucidated by using the modified Mosher method for pentacecilide C. The inhibitory activity of all pentacecilides against lipid droplet formation and acyl-CoA:cholesterol acyltransferase isozymes was compared.

A New Meroterpenoid, Chrodrimanin C, from YO-2 ofTalaromycessp.

“…Apart from chrodrimanins, kampanols, 10) thailandolides, 11) and pentacecilides 12,13) have been reported as merodrimanes. Kampanols isolated from a fungal culture of Stachybotrys kampalensis have inhibited Ras farnesyl-protein transferase.…”

“…IR spectra were recorded with a Jasco FT/IR-460 spectrophotometer, mass spectra were recorded with a Jeol JMS-700 instrument, and 1 H-and 13 C-NMR spectra were obtained with a Jeol JNM AL-400 spectrometer. Chemical shifts are referenced to residual CHCl 3 at 7.26 ppm for the 1 H spectra, to CDCl 3 at 77.0 ppm for the 13 C spectra, to DMSO at 2.50 ppm for the 1 H spectra, and to DMSO-d 6 at 39.5 ppm for the 13 C spectra, each being reported relative to TMS. Column chromatography was performed with Wakogel C-200 (Wako Pure Chemical Industries) and Inertsil ODS-3 (GL Sciences).…”

Frontier studies on highly selective bio-regulators useful for environmentally benign agricultural production

“…22) Chrodrimanins are considered to be meroterpenoids consisting of sesquiterpenoid and pentaketide moieties, and only the pentacecilide family has been reported to have the same carbon skeleton as chrodrimanins with a different stereochemistry. 23) 1.2. Convulsive compounds 1.2.1.…”

Isoform-Specific Inhibitors of Acats: Recent Advances and Promising Developments

“…In contrast, some compounds (e.g., beauveriolides, spylidone and pentacecilides) were identified from cell-based assays using lipid droplet synthesis in macrophages [80][81][82][83][84][85][86]. The mechanism of action of these compounds revealed that they inhibited ACAT activity.…”

“…However, knowledge of the two isoforms is important for determining the selectivity of inhibitors toward the two isoforms for development of novel anti-atherosclerotic agents. Only a few studies have reported the selectivity of ACAT inhibitors [86,[94][95][96][97][98][99][100]. Two sophisticated cell lines in which ACAT1 and ACAT2 genes from the African Green Monkey were transfected into the ACAT-deficient Chinese Hamster Ovary (CHO) cell line AC29 [101] were used to measure ACAT1 and ACAT2 activity [94].…”