Identification of the chemical compositions of Ponkan peel by ultra performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry

Yang, Ying; Zhao, Xi; Pan, Yu; Zhou, Zhiqin

doi:10.1039/c5ay02633d

Cited by 43 publications

(39 citation statements)

References 50 publications

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“…Compounds 1-4 are the major CLs and 2 has also recently been found in the barks of Citrus genus [7,25] and in root bark of Dictamnus angustifolius [122,123]. When biological activities are considered, 2 shares the same profile of 1 ( Table 2) displaying comparable potencies in a range from five-fold lower to five-fold higher values than the ones shown by 1 [46,67,77].…”

Section: Nomilin (2mentioning

confidence: 56%

“…Furthermore, 14 and 46 were characterized for the first time in Ponkan peel. It is noteworthy that the method is very fast since the well separation of chemical components in Ponkan peel was completed in 7 min [7].…”

Section: Metabolomic Analysismentioning

confidence: 99%

“…CLs are regarded as highly oxygenated triterprenoids as they contain relatively high numbers of oxygen atoms (7)(8)(9)(10)(11) in their structures. CLs are found as both free aglycones and corresponding β-D-glucosides, the former mostly occurring in seeds while the latter are formed during fruit maturation.…”

Section: Complexity and Evolution Of Citrus Limonoid Researchmentioning

confidence: 99%

“…Citrus limonoids (CLs) are a crowded family of polycyclic secondary metabolites found mostly in seeds [1], fruits [2], and peel [3][4][5][6][7] tissues of citrus fruits, including lemons, limes, oranges (both sour and sweet), pumellos, grapefruits, bergamots, and mandarins [5]. CLs are regarded as highly oxygenated triterprenoids as they contain relatively high numbers of oxygen atoms (7)(8)(9)(10)(11) in their structures.…”

Section: Complexity and Evolution Of Citrus Limonoid Researchmentioning

confidence: 99%

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The Chemistry and Pharmacology of Citrus Limonoids

et al. 2016

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Citrus limonoids (CLs) are a group of highly oxygenated terpenoid secondary metabolites found mostly in the seeds, fruits and peel tissues of citrus fruits such as lemons, limes, oranges, pumellos, grapefruits, bergamots, and mandarins. Represented by limonin, the aglycones and glycosides of CLs have shown to display numerous pharmacological activities including anticancer, antimicrobial, antioxidant, antidiabetic and insecticidal among others. In this review, the chemistry and pharmacology of CLs are systematically scrutinised through the use of medicinal chemistry tools and structure-activity relationship approach. Synthetic derivatives and other structurally-related limonoids from other sources are include in the analysis. With the focus on literature in the past decade, the chemical classification of CLs, their physico-chemical properties as drugs, their biosynthesis and enzymatic modifications, possible ways of enhancing their biological activities through structural modifications, their ligand efficiency metrics and systematic graphical radar plot analysis to assess their developability as drugs are among those discussed in detail.

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Section: Nomilin (2mentioning

confidence: 56%

Section: Metabolomic Analysismentioning

confidence: 99%

Section: Complexity and Evolution Of Citrus Limonoid Researchmentioning

confidence: 99%

Section: Complexity and Evolution Of Citrus Limonoid Researchmentioning

confidence: 99%

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The Chemistry and Pharmacology of Citrus Limonoids

et al. 2016

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“…Flavonoids 1-10 were previously isolated from sweet oranges (C. sinensis). [18][19][20][21][22][23][24][25] The total concentration of flavonoids in the sample analyzed was 160.0 mg mL -1 and it was injected 20 times , respectively. This study showed the high quality and potential of the Brazilian CFPW considering the investigated compounds, which could serve as an inexpensive and readily available source of polymethoxylated flavonoids.…”

Section: Resultsmentioning

confidence: 99%

An Environmentally Friendly Procedure to Obtain Flavonoids From Brazilian Citrus Waste

Bellete¹,

Ramin²,

Porto³

et al. 2018

J. Braz. Chem. Soc.

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Currently, most food waste is used as animal feed and this process does not take advantage of the available chemical composition. A Brazilian example is the citrus fruit processing wastes (CFPW), which have begun to draw attention due to their biological importance. In order to access the main compounds of this matrix, an efficient and environmentally friendly procedure was tested. From this extract, flavonoids as naringenin, hesperitin, chrysoeriol, sinensetin, 3,5,6,7,3',4'-hexamethoxyflavone, nobiletin, 5-methoxysalvigenin, 3,5,6,7,8,3',4'-heptamethoxyflavone, 3,5,6,7,4'-pentamethoxyflavone and isosakuranetin were identified by high performance liquid chromatography (HPLC-UV), liquid chromatography-mass spectrometry (LC-MS) and liquid chromatography-nuclear magnetic resonance (LC-NMR). This study describes the potential use of citrus waste as a source of biologically active compounds. The extraction method proposed for this work was not expensive and the flavonoids were obtained in large amounts, thus, this extraction method is being developed using pilot plant scale-up techniques and will soon be available to the industry at a low cost.

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Antioxidant capacity and fragmentation features of C‐glycoside isoflavones by high‐resolution electrospray ionization tandem mass spectrometry using collision‐induced and high‐energy collisional dissociation techniques

et al. 2021

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The rapid annotation and identification by mass spectrometry techniques of flavonoids remains a challenge, due to their structural diversity and the limited availability of reference standards. This study applies a workflow to characterize two isoflavonoids, the orobol-C-glycosides analogs, using high-energy collisional dissociation (HCD)-and collision-induced dissociation (CID)-type fragmentation patterns, and also to evaluate the antioxidant effects of these compounds by ferric reducing antioxidant power (FRAP), 2,2 0 -azino-bis(3-ethylbenzothiazolin acid) 6-sulfonic acid (ABTS), and 2,2-diphenyl-1-picrylhydrazyl (DPPH) methods. By the CID-type fragmentation, in positive mode and at all high-resolution mass spectrometry (HRMS) multiple stage, there were shown differences in the annotation of the compounds, mainly concerning some ratios of relative abundance. At CID-MS 2 20 eV, the compounds could be efficiently characterized, because they present distinct base peaks [M + H] + and [M + H-H 2 O] + for the orobol-8-C-and orobol-6-C-glycoside, respectively. Similarly, by the HCD-type fragmentation, in HRMS 2 stage, differences between orobol analogs in both mode of ionization were observed. However, the HR HCD-MS 2 at 80 eV, in positive mode, generated more ions and each isomer presented different base peaks ions, [0,2X] + for the orobol-8-C-glycoside and [0,3X] + for the orobol-6-Cglycoside. By the DPPH, the 8-C-derivative showed a very close value compared with the standard rutin and, in the ABTS method, a higher radical-scavenging activity. In both methods, the EC 50 of orobol-8-C-glycoside was almost twice better compared with orobol-6-C-glycoside. In FRAP, both C-glycosides showed a good capacity as Fe +3 reducing agents. We could realize that combined MS techniques, highlighting the positive mode of ionization, can be used to evaluate the isoflavones analogs being useful to differentiate between the isomeric flavones; therefore, these data are important to mass spectrometry dereplication studies become more efficient.

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Identification of the chemical compositions of Ponkan peel by ultra performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry

Abstract: A new UPLC-Q-TOF-MS method has been reported for the qualitative analysis and profiling of chemical compositions of Ponkan peel.

Cited by 43 publications

References 50 publications

The Chemistry and Pharmacology of Citrus Limonoids

The Chemistry and Pharmacology of Citrus Limonoids

An Environmentally Friendly Procedure to Obtain Flavonoids From Brazilian Citrus Waste

Antioxidant capacity and fragmentation features of C‐glycoside isoflavones by high‐resolution electrospray ionization tandem mass spectrometry using collision‐induced and high‐energy collisional dissociation techniques

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