Phytochemical analysis of Vernonanthura tweedieana and a validated UPLC-PDA method for the quantification of eriodictyol

Silva, Layzon Antonio Lemos da; Faqueti, Larissa; Reginatto, Flávio Henrique; Santos, Alan Diego da Conceição; Barison, Andersson; Biavatti, Maique W.

doi:10.1016/j.bjp.2015.07.009

Cited by 44 publications

(29 citation statements)

References 32 publications

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“…Tandem data of these peaks (Table ) are in agreement to the literature . All these four compounds were previously characterized from V. tweedieana species . Moreover, three others methoxylated flavones were also identified, namely, luteolin‐7‐methyl ether ( IV , t R : 2.26 min, m/z 301.0732 [C 16 H 12 O 6 +H] + ), genkwanin ( VIII , t R : 3.14 min, m/z 285.0757 [C 16 H 12 O 5 +H] + ), and velutin ( X , t R : 3.40 min, m/z 315.0851 [C 17 H 14 O 6 +H] + ), whose MS/MS data and fragmentation pattern were in according to literature .…”

Section: Resultssupporting

confidence: 85%

ESI‐QTof‐MS characterization of hirsutinolide and glaucolide sesquiterpene lactones: Fragmentation mechanisms and differentiation based on Na⁺/H⁺ adducts interactions in complex mixture

et al. 2019

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Sesquiterpene lactones (SL) have been reported with various biological effects.Among the described SL skeletons, hirsutinolide and glaucolide have not been extensively studied by mass spectrometry (MS), especially how to distinguish them in organic matrices. Thus, this paper reports (1) a strategy of their differentiation based on MS behavior during the ionization and (2) a proposal of the fragmentation pattern for both SL-subtypes. ESI(+)-HRMS data of four isolated SL (hirsutinolides 1 and 3; glaucolides 2 and 4) were recorded by direct and UPLC water-sample combined injections. These analyses revealed that hirsutinolides and glaucolides formed [M+Na] + ion during the operation of the direct MS injection, and ([M+Na] + and [M+H-H 2 O] + ) and[M+H] + ions were respectively observed for hirsutinolides and glaucolides during the operation of combined UPLC water and sample MS injection. Computational simulations showed that the complex hirsutinolide (1)-Na + formed with a lower preparation energy compared with the complex glaucolide (2)-Na + . However, despite their different behavior during the ionization process, ESI(+)-HRMS/MS analyses of 1-4 gave similar fragmentation patterns at m/z 277, 259, 241, and 231 that can be used as diagnostic ions for both skeletons. Moreover, the differentiation strategy based on the nature of the complex SL-adducts and their MS/MS fragmentation pattern were successfully applied for the chemical characterization of the extract from Vernonanthura tweedieana using UPLC-ESI-HRMS/MS. Among the characterized metabolites, SL with hirsutinolide and glaucolide skeletons showed the aforementioned diagnostic fragments and an ionization behavior that was similar to those observed during the water-sample combined injection. KEYWORDShirsutinolides and glaucolides, ESI-QTofMS n analysis, ESI adducts interaction, fragmentation mechanism, computational study Correction added on 22 May 2020, after online publication: the data in Tables 1, 2, 3, 5 and the citation numbering throughout the article were corrected post publication. /journal/jms 915 916 DA SILVA ET AL. Journal of MASS SPECTROMETRY RESULTS AND DISCUSSION ESI-HRMS/MS analysis of pure compoundsAs depicted in Table 1, ESI(+)-HRMS analysis by direct injection indicated that the SL 1-4 afforded as base peak the ions at m/z 445.1473 (1), m/z 487.1570 (2), m/z 419.1327 (3), and m/z 461.1422 (4), corresponding to [M+Na] + and suggesting a strong affinity for Na + . Moreover, protonated ions [M+H] + were not detected for the hirsutinolide skeletons ( compounds 1 and 3), whereas [M+H] + ions were observed in extremely low abundance for glaucolides 2 (m/z 465.1740, 15%) and 4 (m/z 439.1620, 2%).DA SILVA ET AL.

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Section: Resultssupporting

confidence: 85%

ESI‐QTof‐MS characterization of hirsutinolide and glaucolide sesquiterpene lactones: Fragmentation mechanisms and differentiation based on Na⁺/H⁺ adducts interactions in complex mixture

et al. 2019

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“…The combined 100% acetone and 50% acetone extract of aerial parts of B. linariifolia was subjected to various column chromatographic methods including MCI gel CHP20P, Sephadex LH-20, and silica gel, and four phenolic compounds were isolated. The chemical structures of the isolated compounds were elucidated as verbascoside (1) [35,36], vanillic acid (2) [37], apigenin (3) [38], and 6"-O-p-coumaroylprunin (4) [39] (Figure 1), on the basis of their NMR spectral data (Tables 1-3) and comparison to literature values. This is the first report for the isolation and identification of these phenolic compounds from B. linariifolia.…”

Section: Resultsmentioning

confidence: 99%

Phenolic Compounds from the Aerial Parts of Blepharis linariifolia Pers. and Their Free Radical Scavenging and Enzyme Inhibitory Activities

et al. 2019

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Background: Blepharis linariifolia Pers. (Family: Acanthaceae) is used in traditional medicines as a general tonic and for the treatment of various health problems in Sudan. The main aim of this study was to isolate and identify the major chemical constituents from the aerial parts of B. linariifolia and evaluate their bioactivities. Methods: The dried aerial parts of the plant were extracted successively with 100% acetone and 50% acetone, and thereafter the combined extract was subjected to repeated column chromatography to isolate the main components. Free radical scavenging activity was evaluated using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical method, and in vitro enzyme inhibitory activities against α-glucosidase, pancreatic lipase, and mushroom tyrosinase were evaluated. Results: From the detailed chemical analysis, verbascoside (1), vanillic acid (2), apigenin (3), and 6″-O-p-coumaroylprunin (4), were isolated and their structures were identified on the basis of their nuclear magnetic resonance (NMR) spectral data. Among the isolated compounds, verbascoside (1) showed the most potent free radical scavenging activity (IC50 = 22.03 ± 0.04 μM). Apigenin (3) and 6″-O-p-coumaroylprunin (4) showed promising inhibitory activities against all tested enzymes. Apigenin (3) showed the most potent inhibitory activity against α-glucosidase and tyrosinase (IC50 = 34.73 ± 1.78 μM and 23.14 ± 1.83 μM, respectively), whereas 6″-O-p-coumaroylprunin (4) showed potent inhibition for lipase (IC50 = 2.25 ± 0.17 μM). Conclusions: Four phenolic compounds were isolated and identified from B. linariifolia acetone extract, which are reported for the first time from this plant. All compounds showed good DPPH free radical scavenging activities, with verbascoside (1) being the most potent. Apigenin (3) was the most active as α-glucosidase and mushroom tyrosinase inhibitor, while 6″-O-p-coumaroylprunin (4) showed potent inhibitory activity for pancreatic lipase.

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“…Based on the NMR and MS investigations, compound 1 was identified as ingenol, 11 compound 2 as naringenin (4′,5,7-trihydroxyflavanone), 12,13 and compound 3 as eriodictyol (3′,4′,5,7-tetrahydroxyflavanone). 12,13 All compounds were isolated for the first time from E. matabelensis. 5 Ingenol 3-angelate, the best-known ingenol derivative, is used in human therapy (Picato) for the treatment of actinic keratosis, a precancerous skin disease.…”

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Isolation and Pharmacological Investigation of Compounds From Euphorbia matabelensis

Hammadi

Kúsz

Mwangi

et al. 2019

Natural Product Communications

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This work deals with the isolation and pharmacological investigations of compounds of Euphorbia matabelensis. After multiple separation process, including thin layer chromatography (TLC), vacuum liquid chromatography, preparative TLC, and high-performance liquid chromatography, 1 diterpene (ingenol) and 2 flavonoids (naringenin and eriodictyol) were obtained from the methanol extracts prepared from the stems and roots of the plant. The structures of the isolated compounds were determined by nuclear magnetic resonance (NMR) and MS measurements and comparison with literature data. All compounds were isolated for the first time from the plant. Eriodictyol was detected for the first time from a Euphorbia species. The compounds were tested for their antiproliferative (on HeLa, C33a, MCF-7, and MDA-MB-231 cell lines) and GIRK channel blocking activities. None of the compounds proved to be active in these test systems.

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Phytochemical analysis of Vernonanthura tweedieana and a validated UPLC-PDA method for the quantification of eriodictyol

Cited by 44 publications

References 32 publications

ESI‐QTof‐MS characterization of hirsutinolide and glaucolide sesquiterpene lactones: Fragmentation mechanisms and differentiation based on Na⁺/H⁺ adducts interactions in complex mixture

ESI‐QTof‐MS characterization of hirsutinolide and glaucolide sesquiterpene lactones: Fragmentation mechanisms and differentiation based on Na⁺/H⁺ adducts interactions in complex mixture

Phenolic Compounds from the Aerial Parts of Blepharis linariifolia Pers. and Their Free Radical Scavenging and Enzyme Inhibitory Activities

Isolation and Pharmacological Investigation of Compounds From Euphorbia matabelensis

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Phytochemical analysis of Vernonanthura tweedieana and a validated UPLC-PDA method for the quantification of eriodictyol

Cited by 44 publications

References 32 publications

ESI‐QTof‐MS characterization of hirsutinolide and glaucolide sesquiterpene lactones: Fragmentation mechanisms and differentiation based on Na+/H+ adducts interactions in complex mixture

ESI‐QTof‐MS characterization of hirsutinolide and glaucolide sesquiterpene lactones: Fragmentation mechanisms and differentiation based on Na+/H+ adducts interactions in complex mixture

Phenolic Compounds from the Aerial Parts of Blepharis linariifolia Pers. and Their Free Radical Scavenging and Enzyme Inhibitory Activities

Isolation and Pharmacological Investigation of Compounds From Euphorbia matabelensis

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ESI‐QTof‐MS characterization of hirsutinolide and glaucolide sesquiterpene lactones: Fragmentation mechanisms and differentiation based on Na⁺/H⁺ adducts interactions in complex mixture

ESI‐QTof‐MS characterization of hirsutinolide and glaucolide sesquiterpene lactones: Fragmentation mechanisms and differentiation based on Na⁺/H⁺ adducts interactions in complex mixture