Article

LC/MS/NMR analysis of isomeric divanilloylquinic acids from the root bark of Fagara zanthoxyloides Lam

Vrije Universiteit Brussel, Bruxelles, Brussels Capital, Belgium
Phytochemistry (Impact Factor: 2.55). 05/2004; 65(8):1145-51. DOI: 10.1016/j.phytochem.2004.02.025
Source: PubMed

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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    • "Because of the complexity of the crude extracts, various on-line hyphenated techniques have been developed for the analysis of these mixtures (Dai et al., 2009). These techniques include liquid chromatography (LC) tandem mass spectrometry (MS/MS) (Cui et al., 2004; Li et al., 2005, 2006; Geng et al., 2007; Huang et al., 2007; Dong et al., 2007), LC–nuclear magnetic resonance (NMR) spectrometry (Watanabe and Niki, 1978; Prakash et al., 2007; Wolfender et al., 2005) and LC–NMR–MS (Gil et al., 2003; Duarte et al., 2003; Ouattara et al., 2004). They facilitate the structure determination of unknown constituents in crude extracts. "
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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.
    Full-text · Article · Sep 2014 · Industrial Crops and Products
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    • "The full assignment of all proton and carbon signals of both compounds was achieved by thorough investigation of 2D NMR spectra (COSY, HMQC and HMBC). The location of the p-coumaroyl substitutions on the quinic acid moiety was deduced from the comparative analyses of 1 H and 13 C NMR data with those reported for free quinic acid and its derivatives (Hyun et al., 2010; Ouattara et al., 2004). For 3 and 4, the downfield shift of H-4 (d H 5.00 for 3 and 4.99 for 4) and H-5 (d H 5.45 for 3 and 5.50 for 4) suggested quinic acid derivatives esterified at positions 4 and 5 by the two p-coumaroyl moieties. "
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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.
    Full-text · Article · May 2013 · Phytochemistry
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    • "The full assignment of all proton and carbon signals of both compounds was achieved by thorough investigation of 2D NMR spectra (COSY, HMQC and HMBC). The location of the p-coumaroyl substitutions on the quinic acid moiety was deduced from the comparative analyses of 1 H and 13 C NMR data with those reported for free quinic acid and its derivatives (Hyun et al., 2010; Ouattara et al., 2004). For 3 and 4, the downfield shift of H-4 (d H 5.00 for 3 and 4.99 for 4) and H-5 (d H 5.45 for 3 and 5.50 for 4) suggested quinic acid derivatives esterified at positions 4 and 5 by the two p-coumaroyl moieties. "
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    ABSTRACT: Tribulus terrestris L. is a well known and widely distributed species of the genus Tribulus [1]. 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.
    Full-text · Conference Paper · Apr 2013
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