Showing papers by "Thomas Simmet published in 2003"
TL;DR: It is demonstrated that differentiation of human monocytes is associated with differential expression of functionally active PARs that mediate distinct regulatory functions in inflammation and atherogenesis.
221 citations
TL;DR: This is the first report identifying a novel pentacyclic triterpene, lupeolic acid, as a constituent of frankincense gum resins, as well as in related phytopharmaceuticals.
102 citations
TL;DR: The overall average extraction yield of 12 different pentacyclic triterpenic acids was approximately 66% and the calibration graphs were linear with coefficients of correlation for all compounds greater than 0.999.
95 citations
TL;DR: In this paper, 3α-acetyl-β-boswellic acid methyl ester was synthesized for experiments with a shift reagent, Eu(fod)3, that enhanced the resolution considerably.
Abstract: 3α-Acetyl-β-boswellic acid (1), 3α-acetyl-α-boswellic acid (2), 3α-acetyl-9,11-dehydro-β-boswellic acid (3), 3α-acetyl-9,11-dehydro-α-boswellic acid (4) and 3α-acetyl-11-keto-β-boswellic acid (5) were isolated from the gum resin of Boswellia serrata. 1D and 2D NMR (COSY45, HMQC, HMBC, ROESY) spectra at 500 MHz were used for shift assignments and structure verification. All boswellic acids investigated share the cis conformation at ring D/E and the 3α orientation of the acetyl ester group. Owing to high-order spectra, NMR could not determine the exact conformation of H-20/H-30 of the β-boswellic acids. 3α-Acetyl-β-boswellic acid methyl ester (1′) was synthesized for experiments with a shift reagent, Eu(fod)3, that enhanced the resolution considerably. The oxygen atoms of the 3α-acetyl group form the apparent complex binding site for the shift reagent. Copyright © 2003 John Wiley & Sons, Ltd.
47 citations
TL;DR: In this paper, 3α-Acetyl-20(29)-lupene-24-oic acid was isolated from the gum resin of Boswellia serrata.
Abstract: 3α-Acetyl-20(29)-lupene-24-oic acid (1) was isolated from the gum resin of Boswellia serrata. Its presence evidently suggests, that the oxidosqualene triterpene pathway of Boswellia serrata closely resembles the biosynthetic route already found in other plants. Complete 1H and 13C spectral assignments were derived from 1D and 2D NMR spectra. This is the first compound with the lupene backbone combining a 3α-hydroxy or 3α-acetyl group with the 24-carboxyl group, a configuration which is typical of the classical boswellic acids. Copyright © 2003 John Wiley & Sons, Ltd.
12 citations