Mass spectrometry of 3,5- and 4,5-dicaffeoylquinic acids and selected derivatives

Miketová, Petra; Schram, Karl H.; Whitney, Jeffery; Kearns, Edward H.; Timmermann, Barbara N.

doi:10.1002/(sici)1096-9888(199912)34:12<1240::aid-jms896>3.3.co;2-2

Cited by 9 publications

(18 citation statements)

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“…Miketova, Schram, Whitney, Kearns, and Timmermann (1999) reported structure-activity relationships for CQA isomers towards HIV. Thus, it seems important not only to detect and identify the different CQA isomers present in a plant extract matrix but also to quantify them, a task not always easy even with access to modern techniques, due to problems of great similarity of spectra and to the common co-elution of these compounds.…”

Section: Introductionmentioning

confidence: 99%

Validation of a HPLC-DAD–ESI/MSn method for caffeoylquinic acids separation, quantification and identification in medicinal Helichrysum species from Macaronesia

Gouveia¹,

Castilho²

2012

Food Research International

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The caffeoylquinic acids (CQA) found in Helichrysum species from Madeira Archipelago were identified and quantified. The HPLC-DAD-ESI/MS n method applied was developed and validated showing a good repeatability with recovery values ≥96%. The use of a RP-C 18 with a small internal diameter (Ø 3.0 mm) and an acidic mobile phase (acetonitrile and water with 0.1% (v/v) of formic acid) enabled the separation of all compounds within a 30 min analysis. A good resolution between 1,5-O-diCQA and 3,5-O-diCQA isomers, usually hard to separate, was also accomplished. Dicaffeoylquinic acids isomers were the major components among the quantified hydroxycinnamic acids. 1,5-O-diCQA, 3,5-O-diCQA and 5-O-CQA were the compounds found in higher amounts for the different species. The distinct uses of these plants described in the local folk medicine can be related to the phenolic composition.

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Section: Introductionmentioning

confidence: 99%

Validation of a HPLC-DAD–ESI/MSn method for caffeoylquinic acids separation, quantification and identification in medicinal Helichrysum species from Macaronesia

Gouveia¹,

Castilho²

2012

Food Research International

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“…However, a facile method for the preparation of large quantities of 1 from 1,5‐DCQA ( 2 ) has recently been reported 8. In addition, the substitution pattern of the ester functions on the quinic acid moiety are known to affect the anti‐HIV activity of DCQAs and the hexaacetate derivatives of some DCQAs show considerably greater anti‐HIV activity than their underivatized counterparts,9 possibly because of the greater lipophilicity of the acetates.…”

Section: Introductionmentioning

confidence: 99%

“…Sensitive methods are needed for the detection and structure elucidation of the DCQAs and their derivatives, because of the sometimes small amount of material isolated from natural sources. Mass spectrometry has been used in the structure elucidation of some of the DCQAs 10 and methods for differentiating some isomers of DCQAs are possible by mass spectrometry 9. For example, the mass spectra of 3,5‐DCQA ( 3 ) and of its hexaacetate derivative show a selective the loss of water which serves to distinguish this isomer from the 4,5‐DCQA ( 4 ) analog 9.…”

Section: Introductionmentioning

confidence: 99%

Mass spectrometry of 1,3‐ and 1,5‐dicaffeoylquinic acids

et al. 2004

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Samples of 1,3- (1) and 1,5-dicaffeoylquinic acid (2) and their hexaacetate derivatives were examined using positive and negative electrospray ionization mass spectrometry and tandem mass spectrometry. Differences in the various spectra allow the discrimination of each of the isomers. Specific losses in the spectra of 2 also permit the identification of the site of substitution of one of the caffeic acid moieties as being at the 5-position. The spectra of 3,5- (3) and 4,5-dicaffeoylquinic (4) acids and their hexaacetate derivatives were compared with those of 1 and 2 and their derivatives, and differences in ion abundances or the presence/absence of specific ions can be used to identify uniquely each of the compounds.

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“…Fractions 12, 13 and 16 were submitted to 1 H-NMR and 13 C-NMR (300 MHz and 75 MHz, respectively) and ESI-MS. The data obtained were compared with literature values (Merfort, 1992;Pauli et al, 1998;Miketova et al, 1999), and the compounds were identified as quinic acid esters: fraction 12 (compound 1, 64.0 mg, 3,5-di-O-[E]-caffeoylquinic acid) and fraction 13 (compound 2, 58.8 mg, 4,5-di-O-[E]-caffeoylquinic acid) and fraction 16 (compound 3, 12.5 mg, 3,4,5-tri-O-[E]-caffeoylquinic acid) (Fig. 1).…”

Section: Preparation Of the Extract And Fractionsmentioning

confidence: 99%

Analgesic activity of di-caffeoylquinic acids from roots of Lychnophora ericoides (Arnica da serra)

Santos

Gobbo‐Neto

Albarella

et al. 2005

Journal of Ethnopharmacology

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Mass spectrometry of 3,5- and 4,5-dicaffeoylquinic acids and selected derivatives

Cited by 9 publications

References 0 publications

Validation of a HPLC-DAD–ESI/MSn method for caffeoylquinic acids separation, quantification and identification in medicinal Helichrysum species from Macaronesia

Validation of a HPLC-DAD–ESI/MSn method for caffeoylquinic acids separation, quantification and identification in medicinal Helichrysum species from Macaronesia

Mass spectrometry of 1,3‐ and 1,5‐dicaffeoylquinic acids

Analgesic activity of di-caffeoylquinic acids from roots of Lychnophora ericoides (Arnica da serra)

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