LC/MS/NMR analysis of isomeric divanilloylquinic acids from the root bark of Fagara zanthoxyloides Lam.
ABSTRACT Gradient HPLC coupled to DAD/UV, MS/MS and NMR has been applied to the rapid structure determination of three new isomeric divanilloylquinic acids from Fagara zanthoxyloides collected in Burkina Faso: 3,4-O-divanilloylquinic acid, 3,5-O-divanilloylquinic acid and 4,5-O-divanilloylquinic acid. Furthermore these new compounds named burkinabins A-C could play a useful role in sickle cell disease, as the active agents of Fagara zanthoxyloïdes are said to be unidentified aromatic compounds with carboxylic acid grouping (Adesanya, S.A., Sofowora, A., 1983. Biological standardisation of Zanthoxylum roots for antisickling activity. Planta Med. 48, 27-33).
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ABSTRACT: An original analytical protocol for the quantification of labdanolic acid (LA) present in the crude oil of Cistus ladaniferus plant was successfully developed during this investigation. The application of the new method, based on the HPLC technique with UV detection at 240 nm, involves prior derivatization of LA with benzyl bromide to the corresponding benzyl ester. By using the implemented analytical method, a seasonal and regional distribution of LA during a broad period of time was completed. Extracts of C. ladaniferus from three different locations in Portugal, harvested during the same season and also during different seasons within the same harvest location were analysed. From this study, it was shown that regional influences are more important for the production of LA by the plant than seasonal variations. Lastly, a series of molecular imprinted polymers (MIPs) and their corresponding non-imprinted polymers (NIPs) were synthesised using supercritical carbon dioxide and applied on the LA purification from the acidic crude oil of C. ladaniferus. From all the tested polymers, the 2-(dimethylamino)ethyl methacrylate non-imprinted polymer (DMAEMA-NIP) revealed the most preeminent result on the LA purification. After passing twice the acidic crude containing 15% of LA in the DMAEMA-NIP, 34% of LA was recovered due to the selective retention of non-desired compounds by the polymer.Industrial Crops and Products 09/2014; 60:226–232. DOI:10.1016/j.indcrop.2014.06.012 · 2.84 Impact Factor
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ABSTRACT: Two oligosaccharides (1,2) and a stereoisomer of di-p-coumaroylquinic acid (3) were isolated from the aerial parts of Tribulus terrestris along with five known compounds (4-8). The structures of the compounds were established as O-β-d-fructofuranosyl-(2→6)-α-d-glucopyranosyl-(1→6)-β-d-fructofuranosyl-(2→6)-β-d-fructofuranosyl-(2→1)-α-d-glucopyranosyl-(6→2)-β-d-fructofuranoside (1), O-α-d-glucopyranosyl-(1→4)-α-d-glucopyranosyl-(1→4)-α-d-glucopyranosyl-(1→2)-β-d-fructofuranoside (2), 4,5-di-p-cis-coumaroylquinic acid (3) by different spectroscopic methods including 1D NMR ((1)H, (13)C and DEPT) and 2D NMR (COSY, TOCSY, HMQC and HMBC) experiments as well as ESI-MS analysis. This is the first report for the complete NMR spectral data of the known 4,5-di-p-trans-coumaroylquinic acid (4). The antioxidant activity represented as DPPH free radical scavenging activity was investigated revealing that the di-p-coumaroylquinic acid derivatives possess potent antioxidant activity so considered the major constituents contributing to the antioxidant effect of the plant.Phytochemistry 05/2013; DOI:10.1016/j.phytochem.2013.04.005 · 3.35 Impact Factor
Conference Paper: Phytochemical and Antioxidant Investigation of Tribulus terrestris[Show abstract] [Hide abstract]
ABSTRACT: Tribulus terrestris L. is a well known and widely distributed species of the genus Tribulus . The phytochemical investigation of the aerial parts of T. terrestris led to the isolation of two new oligosaccharides (1, 2) and a new stereoisomer of di-p-coumaroylquinic acid (3) along with five known compounds. The structures of the compounds were established as O-β-D-fructofuranosyl-(2 – 6)-α-D-glucopyranosyl-(1 – 6)-β-D-fructofuranosyl-(2 – 6)-β-D-fructo-furanosyl-(2 – 1)-α-D-glucopyranosyl-(6 – 2)-β-D-fructofuranoside (1), O-α-D-glucopyranosyl-(1 – 4)-α-D-glucopyranosyl-(1 – 4)-α-D-glucopyranosyl-(1 – 2)-β-D-fructofuranoside (2), 4,5-di-p-cis-coumaro-ylquinic acid (3), 5-p-cis-coumaroyl-quinic acid, 4,5-di-p-trans-coumaroylquinic acid (3), 5-p-trans-coumaroylquinic acid, diosgenin-3-O-α-L-rhamno-pyranosyl-(1 – 4)-β-D-gluco-pyranoside and dioscin by different spectroscopic methods including 1D- (1 H, 13C and DEPT) and 2D-NMR (COSY, HMQC and HMBC) experiments as well as HR-ESI-MS analysis. All the isolated compounds, except dioscin, are reported for the first time from the family Zygophyllaceae. In addition, this is the first report for the complete NMR spectral data of the known 4,5-di-p-trans-coumaroylquinic acid. The antioxidant activity represented as DPPH free radical scavenging activity was investigated revealing that the di-p-coumaroylquinic acid derivatives possess potent antioxidant activity and so could be considered to be the major constituents contributing to the antioxidant effect of the plant.12th Annual Oxford International Conference on the Science of Botanicals (ICSB), University of Mississippi, University, MS, USA; 04/2013