Mass spectral characterization of C-glycosidic flavonoids isolated from a medicinal plant (Passiflora incarnata)

Li, Qimin; Heuvel, H. van den; Delorenzo, O.; Corthout, J.; Pieters, Luc; Vlietinck, A. J.; Claeys, Magda

doi:10.1016/0378-4347(91)80597-6

Cited by 71 publications

(15 citation statements)

References 11 publications

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“…The abundance of the M-H-90 ion in the MS 2 spectrum showed that the C-bound sugar was attached to the C-6position, indicating an isovitexin structure. The data are in agreement with literature (Qimin et al, 1991) for 6-C-glucosyl-O-glycosylapigenin (glucosyl-isovitexin). Peak C represented Isoorientin: MS: 447 (M-H); MS 2 : 357 (M-H-90), 327 (M-H-120).…”

Section: Resultssupporting

confidence: 92%

Partial Leaf Chemical Profiles of a Desert Watermelon Species (Citrullus colocynthis) and Heirloom Watermelon Cultivars (Citrullus lanatus var. lanatus)

Ogbuji¹,

McCutcheon²,

Simmons³

et al. 2012

horts

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Whiteflies [Bemisia tabaci (Gennadius)] and aphids [Aphis gossypii Glover and Myzus persicae (Sulzer)] are serious threats to watermelon by direct feeding and by transmitting viruses of important virus diseases. The desert watermelon Citrullus colocynthis (L.) has been shown to exhibit resistance to these insect pests and could be a useful source for breeding resistance into watermelon [Citrullus lanatus var. lanatus (Thunbs) Matsum & Nakai]. Using high-performance liquid chromatography (HPLC), we found differences among the chemical profiles of two U.S. PIs of C. colocynthis, one PI of C. lanatus var. citroides, and two heirloom watermelon (C. lanatus var. lanatus) cultivars (‘Charleston Gray’ and ‘Mickey Lee’). Flavonoid and caffeic acid derivatives were identified in the leaf extracts by a combination of ultraviolet (UV) and mass spectrometry (MS) spectral analyses. Four phenolic derivatives of caffeic and/or ferulic acid were found to be essentially unique to C. colocynthis. Total flavonoid content was found to be approximately four to 18 times higher in C. colocynthis accessions and seven to nine times higher in C. lanatus var. citroides as compared with watermelon cultivars. Caffeoyl-glucose was also identified in the leaves of watermelon cultivars for the first time. Leaf sugar concentrations (198 to 211 mg·dL−1), read from a glucometer, were statistically the same among the various germplasm entries. These results will help in the development of pest-resistant watermelon.

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Section: Resultssupporting

confidence: 92%

Partial Leaf Chemical Profiles of a Desert Watermelon Species (Citrullus colocynthis) and Heirloom Watermelon Cultivars (Citrullus lanatus var. lanatus)

Ogbuji¹,

McCutcheon²,

Simmons³

et al. 2012

horts

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“…According to these considerations, [M ± HH 2 O] ± and [M ± H − 2H 2 O] ± ions were not considered in the evaluation, since the masses of these fragments are depending on the mass of the original precursor. Based on literature data, in this study, we focused on evaluating the most commonly appearing 0, 1 X, 0, 2 X, 0, 2 XH 2 O, 0, 3 X, 0, 4 X‐2H 2 O and 5, 1 X ions 23, 33, 36, 37. Similar to the previously described experiments with O‐glycosides, a systematic optimization was undertaken with the studied C‐glycosides in both positive and negative ion modes in the fragmentor voltage range of 170–330 V.…”

Section: Resultsmentioning

confidence: 99%

In‐source fragmentation and accurate mass analysis of multiclass flavonoid conjugates by electrospray ionization time‐of‐flight mass spectrometry

2011

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In-source collision-induced dissociation (CID) fragmentation features of multiclass flavonoid glycoconjugates were examined using liquid chromatography electrospray time-of-flight mass spectrometry. Systematic experiments were performed to search for optimal conditions for in-source fragmentation in both positive and negative ion modes. The objective of the study was to attain uniformly appropriate conditions for a wide range of analytes independently of the aglycone, the attached sugar part and the type of bond between the aglycone and the glycan moieties (O- or C-glycosides). Studied substances included representatives of flavonols, flavones, flavanones and anthocyanins and, regarding their glycan parts, mono-, di- and triglycosides with varying distribution of carbohydrate moieties (di-O-glycosides, O-diglycosides, O,C-diglycosides). The breakdown properties of the analytes along with the abundances of the characteristic diagnostic ions required for structural elucidation of complex flavonoid derivatives were evaluated. An optimized value was found for the instrument parameter (fragmentor voltage) affecting the in-source CID fragmentation of the analytes [230 V (ESI+) and 330 V (ESI-)]. Thus, appropriate performance in terms of both highly sensitive full-scan acquisition and fragmentation information was obtained for all the investigated flavonoids. In addition, singularities in the abundance of selected diagnostic ions (e.g. Y(0), Y(1) and Y*) due to variations in the interglycosidic linkage (rutinoside-neohesperidoside) in the glycan part were found and are also evaluated and discussed in detail. The combination of in-source CID fragmentation with high mass accuracy MS detection establishes a working basis for the development of versatile and useful LC-MS methods for wide-scope screening, non-targeted detection and tentative identification of flavonoid derivatives.

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“…1. Apigenin 7-0-neohesperidoside (l), kaempferol 3-0-rutinoside (2), isovitexin 2"-0-glucoside (7), isoorientin 2-0-glucoside (8), schaftoside (9), isoschaftoside (lo), 6,8-C-diglucosyl apigenin (12) and 6,8-C-diglucosyl luteolin (13) were isolated from various plant sources including P a s s i j k a incarnata.6 Rutin (90% purity), naringin (90% purity), hesperidin (90% purity) and vitexin 2"-0-rhamnoside (CHR quality) (compounds 3-6) were purchased from Roth (Karlsruhe, Germany). 6-C-Rhamnosyl-8-C-glucosy1 chrysin (1 1) was synthesized from 6-C-rhamnosyl chrysin.…”

Section: Experimental Samplesmentioning

confidence: 99%

Characterization and differentiation of diglycosyl flavonoids by positive ion fast atom bombardment and tandem mass spectrometry

Claeys

1994

Biol. Mass Spectrom.

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This study shows that fast atom bombardment (FAB) in combination with collisional activation and tandem mass spectrometric techniques is useful for the characterization of, and the differentiation between, O-diglycosyl, O-C-diglycosyl and di-C-glycosyl flavonoids. A quick differentiation between the three types of glycosyl flavonoids is possible by simply examining FAB mass spectra. Low-energy product ion spectra of [M+H]+ ions have been used for determining the carbohydrate sequence in O-diglycosyl flavonoids and characterizing the terminal monosaccharide in O-C-diglycosyl flavonoids. The data obtained for per-O-deuterated precursor ion species of O-diglycosyl flavonoids indicate that O-linked hydrogen atoms are involved in the formation of Yn+ ions. High-energy product ion spectra of [M+H]+ ions enable further characterization and differentiation of isomeric di-6,8-C-glycosides.

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Mass spectral characterization of C-glycosidic flavonoids isolated from a medicinal plant (Passiflora incarnata)

Cited by 71 publications

References 11 publications

Partial Leaf Chemical Profiles of a Desert Watermelon Species (Citrullus colocynthis) and Heirloom Watermelon Cultivars (Citrullus lanatus var. lanatus)

Partial Leaf Chemical Profiles of a Desert Watermelon Species (Citrullus colocynthis) and Heirloom Watermelon Cultivars (Citrullus lanatus var. lanatus)

In‐source fragmentation and accurate mass analysis of multiclass flavonoid conjugates by electrospray ionization time‐of‐flight mass spectrometry

Characterization and differentiation of diglycosyl flavonoids by positive ion fast atom bombardment and tandem mass spectrometry

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