Mass spectrometry of iridoids

Попов, Симеон; Handjieva, Nedjalka

doi:10.1002/mas.1280020404

Cited by 14 publications

(6 citation statements)

References 61 publications

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“…In 6 , water loss occurs from the carboxyl group. The presence of the C‐4 carboxyl group is further characterised by the elimination of CO 2 4…”

Section: Resultsmentioning

confidence: 99%

“…Structural characterization of naturally occurring and synthetically modified iridoids relies on modern spectroscopic methods. Until the advent of soft ionization techniques, the use of mass spectrometry has been limited owing to the unstable nature of these compounds 4. Chemical ionization (CI), field desorption (FD) and direct chemical ionization (DCI) have been successfully used for obtaining structural and molecular mass information.…”

Section: Introductionmentioning

confidence: 99%

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Characterization of iridoids by fast atom bombardment mass spectrometry followed by collision-induced dissociation of [M + Li]+ ions

et al. 2000

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Fast atom bombardment mass spectra of a series of naturally occurring and synthetically modified iridoid glycosides were studied using lithium cationization and collision‐induced dissociation of the resulting [M + Li]+ ions. Lithium cationization leads to the unambiguous determination of the molecular masses of these compounds. Collision‐induced dissociation of the lithiated molecular ions give valuable structural information regarding the nature of the substituent on both the aglycone and the sugar moieties. The characteristic fragmentation pathways identified are (1) elimination of neutral molecules comprising the substituents on either the aglycone or sugar moieties, (2) formation of lithiated aglycone and their fragment ions, (3) formation of lithiated sugar and their fragment ions, (4) fragmentation corresponding to the cleavage of the aglycone or sugar ring and (5) fragmentation characteristic of the substituents present in either the aglycone or sugar parts of the molecule. Elimination of two acyloxy radicals from the lithiated molecular ion is a characteristic fragmentation in the case of acyloxy derivatives. Copyright © 2000 John Wiley & Sons, Ltd.

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“…In 6 , water loss occurs from the carboxyl group. The presence of the C‐4 carboxyl group is further characterised by the elimination of CO 2 4…”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Characterization of iridoids by fast atom bombardment mass spectrometry followed by collision-induced dissociation of [M + Li]+ ions

et al. 2000

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“…Our proposals were based on the main iridoid aglycones found in the genera Genipa and Hymenaea: genipin and gardoside derivatives. Popov and Handjieva 63 64 with the electrospray ionization mass spectrometry (ESI-MS n ) technique, the same used in this study. Furthermore, on the basis of the structural rearrangements of the iridoid fragmentation pathways, we propose for the ion at m/z 349 the structure called 1,7dihydroxy-5-(4′-methoxybenzoate) 4a,5,6,7a-tetrahydro-1Hcyclopenta[c]pyran-4-carboxylic acid (detected in Genipa americana fruits, locality A and C).…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Brazilian Biodiversity Fruits: Discovering Bioactive Compounds from Underexplored Sources

Biazotto

Mesquita

Neves

et al. 2019

J. Agric. Food Chem.

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Large segments of the Brazilian population still suffer from malnutrition and diet-related illnesses. In contrast, many native fruits have biodiversity and are underexploited sources of bioactive compounds and unknown to consumers. The phytochemical composition of nine underexplored Brazilian fruits was determined. Carotenoids and anthocyanins were identified and quantified by high performance liquid chromatography-photodiode array-tandem mass spectrometry (HPLC-PDA-MS/MS), and phenolic compounds and iridoids were identified by flow injection analysis-electrospray-ion trap-tandem mass spectrometry (FIA-ESI-IT-MS/MS); in total, 84 compounds were identified. In addition, the chemical structure and pathway mass fragmentation of new iridoids from jenipapo (Genipa americana) and jatoba (Hymenae coubaril) are proposed. The highest level of carotenoids was registered in pequi (Caryocar brasiliense; 10156.21 μg/100 g edible fraction), while the major total phenolic content was found in cambuci (Campomanesia coubaril; 221.70 mg GAE/100 g). Anthocyanins were quantified in jabuticaba (Plinia cauliflora; 45.5 mg/100 g) and pitanga (Eugenia uniflora; 81.0 mg/100 g). Our study illustrates the chemical biodiversity of underexplored fruits from Brazil, supporting the identification of new compounds and encouraging the study of more food matrixes not yet investigated.

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“…As for other glycosides, it appears that ammonia is most suitable where determination of the molecular weight is the overriding consideration. On the other hand, methane and isobutane promote more fragmentation and consequently are often more useful in the structural investigations (Popov and Handijeva, 1983). CI with ammonia as reactant gas has been mainly used for iridoid acetate derivatives.…”

Section: Iridoid and Secoiridoid Glycosidesmentioning

confidence: 99%

Mass spectrometry of underivatized naturally occurring glycosides

Wolfender

Maillard

Marston

et al. 1992

Phytochemical Analysis

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Mass spectrometry is essential for the structure determination of naturally occurring glycosides. Molecular weight and sugar sequence information can be obtained. Development of “soft” ionization techniques has allowed a direct mass spectrometric investigation of underivatized glycosides. Numerous different and complementary methods of ionization have been used for their study. For a given compound, the choice of a particular technique is crucial in order to obtain the structural information needed. A brief survey of these ionization techniques is given, together with examples of their use in major classes of plant glycosides.

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Mass spectrometry of iridoids

Cited by 14 publications

References 61 publications

Characterization of iridoids by fast atom bombardment mass spectrometry followed by collision-induced dissociation of [M + Li]+ ions

Characterization of iridoids by fast atom bombardment mass spectrometry followed by collision-induced dissociation of [M + Li]+ ions

Brazilian Biodiversity Fruits: Discovering Bioactive Compounds from Underexplored Sources

Mass spectrometry of underivatized naturally occurring glycosides

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