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Jean-luc Boevé - One of the best experts on this subject based on the ideXlab platform.
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Flavonoid glycosides and Naphthodianthrones in the Sawfly Tenthredo zonula and its Host-Plants, Hypericum perforatum and H. hirsutum
Journal of Chemical Ecology, 2011Co-Authors: Sara L. Crockett, Jean-luc BoevéAbstract:Larvae of the sawfly Tenthredo zonula are specialized on Hypericum . Whether the sawfly is able to sequester plant metabolites was unknown. Aerial materials of Hypericum perforatum and H. hirsutum , as well as dissected larvae and prepupae of T. zonula , were analyzed by HPLC to determine the presence and content of Flavonoid glycosides (rutin, hyperoside, isoquercitrin, and quercitrin) and naphthodianthrones (pseudohypericin and hypericin). All Flavonoid glycosides were detected in both Hypericum species, with hyperoside as major compound in H. perforatum (ca. 1.7 μmol/g fresh weight, FW) and isoquercitrin in H. hirsutum (0.7 μmol/g FW). Naphthodianthrones were present at low concentrations (0.02 μmol/g FW) in the former, and almost undetected in the latter species. In the body parts (i.e., hemolymph, digestive tract, salivary glands, or miscellaneous organs) of T. zonula , the surveyed compounds were detected more frequently in prepupae than in larvae. The compounds were not present in every sample, and Flavonoid glycosides especially occurred in highly variable amounts, with maximal concentrations of 41 μg rutin/prepupa in salivary glands, 8 μg hyperoside/prepupa in hemolymph (= 0.36 μmol/g FW), 32 μg isoquercitrin/prepupa in salivary glands, and 63 μg quercitrin/larva in miscellaneous organs (mainly composed of the integument). We conclude that Flavonoid glycosides are sequestered since they were detected in organs other than the digestive tract of larvae, and because prepupae are a non-feeding stage. The naphthodianthrone pseudohypericin, but not hypericin, occurred generally in the digestive tract (up to 0.25 μg/larva). Both naphthodianthrones and related unidentified compounds, but not Flavonoid glycosides, were found in the larval excrement. The highly variable distributions of Flavonoid glycosides and naphthodianthrones in T. zonula larvae and prepupae make it difficult to determine the ecological significance of these metabolites.
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Flavonoid glycosides and naphthodianthrones in the sawfly Tenthredo zonula and its host-plants, Hypericum perforatum and H. hirsutum.
Journal of chemical ecology, 2011Co-Authors: Sara L. Crockett, Jean-luc BoevéAbstract:Larvae of the sawfly Tenthredo zonula are specialized on Hypericum. Whether the sawfly is able to sequester plant metabolites was unknown. Aerial materials of Hypericum perforatum and H. hirsutum, as well as dissected larvae and prepupae of T. zonula, were analyzed by HPLC to determine the presence and content of Flavonoid glycosides (rutin, hyperoside, isoquercitrin, and quercitrin) and naphthodianthrones (pseudohypericin and hypericin). All Flavonoid glycosides were detected in both Hypericum species, with hyperoside as major compound in H. perforatum (ca. 1.7 μmol/g fresh weight, FW) and isoquercitrin in H. hirsutum (0.7 μmol/g FW). Naphthodianthrones were present at low concentrations (0.02 μmol/g FW) in the former, and almost undetected in the latter species. In the body parts (i.e., hemolymph, digestive tract, salivary glands, or miscellaneous organs) of T. zonula, the surveyed compounds were detected more frequently in prepupae than in larvae. The compounds were not present in every sample, and Flavonoid glycosides especially occurred in highly variable amounts, with maximal concentrations of 41 μg rutin/prepupa in salivary glands, 8 μg hyperoside/prepupa in hemolymph (= 0.36 μmol/g FW), 32 μg isoquercitrin/prepupa in salivary glands, and 63 μg quercitrin/larva in miscellaneous organs (mainly composed of the integument). We conclude that Flavonoid glycosides are sequestered since they were detected in organs other than the digestive tract of larvae, and because prepupae are a non-feeding stage. The naphthodianthrone pseudohypericin, but not hypericin, occurred generally in the digestive tract (up to 0.25 μg/larva). Both naphthodianthrones and related unidentified compounds, but not Flavonoid glycosides, were found in the larval excrement. The highly variable distributions of Flavonoid glycosides and naphthodianthrones in T. zonula larvae and prepupae make it difficult to determine the ecological significance of these metabolites.
Xun Liao - One of the best experts on this subject based on the ideXlab platform.
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identification of Flavonoid glycosides in rosa chinensis flowers by liquid chromatography tandem mass spectrometry in combination with c nuclear magnetic resonance
Journal of Chromatography A, 2012Co-Authors: Lin-sen Qing, Ying Xue, Jian-guang Zhang, Zhi-feng Zhang, Jian Liang, Yan Jiang, Yi-ming Liu, Xun LiaoAbstract:Flowers of Rosa chinensis are widely used in traditional Chinese medicine as well as in food industry. Flavonoid glycosides are believed to be the major components in R. chinensis that are responsible for its antioxidant activities. In this work, a liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) method was developed for analysis of Flavonoid glycosides presented in ethyl acetate extract of dried R. chinensis flowers. Twelve Flavonoid glycosides were separated and detected. By comparing the retention times, UV spectra, and tandem MS fragments with those of respective authentic compounds, eight Flavonoid glycosides were unequivocally identified. Although the other four were also identified as Flavonoid glycosides, the glycosylation positions could not be determined due to lack of authentic compounds. Fortunately, the glycosylation effects were clearly observed in the (13)C NMR spectrum of the extract. The detailed structural information was, therefore, obtained to identify the four Flavonoid glycosides as quercetin-3-O-D-glucoside, quercetin-3-O-D-xyloside, kaempferol-3-O-D-xyloside and quercetin-3-O-D-(6″-coumaroyl)-galactoside. These Flavonoid glycosides were detected and identified for the first time in this botanic material. This work reports on the first use of (13)C NMR of a mixture to enhance a rapid HPLC-MS/MS analysis. The proposed analytical protocol was validated with a mixture of authentic Flavonoid glycosides.
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Identification of Flavonoid glycosides in Rosa chinensis Flowers by Liquid Chromatography-tandem Mass Spectrometry in Combination with 13C Nuclear Magnetic Resonance
Journal of chromatography. A, 2012Co-Authors: Lin-sen Qing, Ying Xue, Jian-guang Zhang, Zhi-feng Zhang, Jian Liang, Yan Jiang, Yi-ming Liu, Xun LiaoAbstract:Flowers of Rosa chinensis are widely used in traditional Chinese medicine as well as in food industry. Flavonoid glycosides are believed to be the major components in R. chinensis that are responsible for its antioxidant activities. In this work, a liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) method was developed for analysis of Flavonoid glycosides presented in ethyl acetate extract of dried R. chinensis flowers. Twelve Flavonoid glycosides were separated and detected. By comparing the retention times, UV spectra, and tandem MS fragments with those of respective authentic compounds, eight Flavonoid glycosides were unequivocally identified. Although the other four were also identified as Flavonoid glycosides, the glycosylation positions could not be determined due to lack of authentic compounds. Fortunately, the glycosylation effects were clearly observed in the C-13 NMR spectrum of the extract. The detailed structural information was, therefore, obtained to identify the four Flavonoid glycosides as quercetin-3-O-D-glucoside, quercetin-3-O-D-xyloside, kaempferol-3-O-D-xyloside and quercetin-3-O-D-(6 ''-coumaroyl)-galactoside. These Flavonoid glycosides were detected and identified for the first time in this botanic material. This work reports on the first use of C-13 NMR of a mixture to enhance a rapid HPLC-MS/MS analysis. The proposed analytical protocol was validated with a mixture of authentic Flavonoid glycosides. (C) 2012 Elsevier B.V. All rights reserved.
Xinmiao Liang - One of the best experts on this subject based on the ideXlab platform.
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isolation and bioactive evaluation of Flavonoid glycosides from lobelia chinensis lour using two dimensional liquid chromatography combined with label free cell phenotypic assays
Journal of Chromatography A, 2019Co-Authors: Jixia Wang, Yu Jin, Xinmiao Liang, Xiuli Zhang, Linlin Chen, Yaopeng Zhao, Zhiwei WangAbstract:Abstract Flavonoid glycosides are widespread in herbs and often used as medicines and nutraceuticals because of good bioactivities and low toxicities. However, due to their structural complexity and diversity, isolation of Flavonoid glycosides and evaluation of their bioactivities are still highly challenging. To solve this problem, a new method for separation and preparation of novel Flavonoid glycosides from Lobelia chinensis Lour (L. chinensis) was developed. To avoid the interference of non-Flavonoids, a solid phase extraction method was used to selectively enrich the Flavonoids from the total extract. Based on hydrophilic and hydrophobic properties of the Flavonoid chemical structure consisting of sugar residue and diphenylpropane (C6C3C6) skeleton, a structure-guided method development strategy was employed to design a 2D-HILIC × RPLC system in the first time. After optimization of chromatographic conditions, high selectivity and symmetric peaks of Flavonoids were obtained on a zwitterionic Click XIon column and a polar-modified Atlantis T3 column. Based on these two columns, a 2 D-HILIC × RPLC system was constructed and successfully enlarged from the analytical level to the preparative level. In the first dimension, 20 fractions were obtained with good peak shapes at high sample loading. In the second-dimensional preparation, nine compounds were isolated and identified. Seven of them were novel Flavonoid glycosides, lobelitin A-G, and two other known compounds were linatin and diosmin, respectively. Their target activities were evaluated via label-free cell phenotypic assays. Four novel Flavonoid glycosides lobelitin A-D were found to have agonistic activities at G protein-coupled receptor 35 (GPR35). These results demonstrated that this method was effective to orthogonally separate Flavonoids at the preparative level, especially for novel active Flavonoid glycosides. The discovery of Flavonoid glycosides with novel agonistic activity on GPR35 also sheds light on the mechanisms of action of L. chinensis relevant to its clinical application.
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selective separation of Flavonoid glycosides in dalbergia odorifera by matrix solid phase dispersion using titania
IEEE Journal of Solid-state Circuits, 2011Co-Authors: Hui Shi, Tu Liang, Jiatao Feng, Yu Jin, Xinmiao LiangAbstract:Selective separation of Flavonoid glycosides in Dalbergia odorifera by matrix solid-phase dispersion using titania
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identification of prenyl Flavonoid glycosides and phenolic acids in epimedium koreanum nakai by q tof ms combined with selective enrichment on click oligo ethylene glycol column
Journal of Pharmaceutical and Biomedical Analysis, 2010Co-Authors: Yaqin Wang, Yu Jin, Zhimou Guo, Xiuli Zhang, Li Wang, Xingya Xue, Xinmiao LiangAbstract:Prenyl Flavonoid glycosides and phenolic acids are constituents of the medicinal plant Epimedium koreanum Nakai (EK). An efficient method was developed to enrich these compounds and identify them, using ultra performance liquid chromatography combined with Q-TOF-MS, and a "click oligo (ethylene glycol)" (Click OEG) column. Using this method, 51 prenyl Flavonoid glycosides and 18 phenolic acids were identified or tentatively identified. Of these, 11 prenyl Flavonoid glycosides and 4 phenolic acids were new compounds, and 7 phenolic acids were newly identified in EK. Therefore, MS combined with selective enrichment provided a powerful means for analyzing prenyl Flavonoid glycosides and phenolic acids.
Lin-sen Qing - One of the best experts on this subject based on the ideXlab platform.
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Determination of Flavonoid glycosides by UPLC-MS to Authenticate Commercial Lemonade.
Molecules (Basel Switzerland), 2019Co-Authors: Ying Xue, Lin-sen Qing, Li Yong, Ming-qing Tang, Jing XieAbstract:So far, there is no report on the quality evaluation of lemonade available in the market. In this study, a sample preparation method was developed for the determination of Flavonoid glycosides by ultra-performance liquid chromatography–mass spectrometry (UPLC-MS) based on vortex-assisted dispersive liquid-liquid microextraction. First, potential Flavonoids in lemonade were scanned and identified by ultra-performance liquid chromatography–time of flight mass spectrometry (UPLC-TOF/MS). Five Flavonoid glycosides were identified as eriocitrin, narirutin, hesperidin, rutin, and diosmin according to the molecular formula provided by TOF/MS and subsequent confirmation of the authentic standard. Then, an ultra-performance liquid chromatography–triple quadrupole mass spectrometry (UPLC-QqQ/MS) method was developed to determine these five Flavonoid glycosides in lemonade. The results showed that the content of rutin in some lemonade was unreasonably high. We suspected that many illegal manufacturers achieved the goal of low-cost counterfeiting lemonade by adding rutin. This suggested that it was necessary for relevant departments of the state to make stricter regulations on the quality standards of lemonade beverages.
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identification of Flavonoid glycosides in rosa chinensis flowers by liquid chromatography tandem mass spectrometry in combination with c nuclear magnetic resonance
Journal of Chromatography A, 2012Co-Authors: Lin-sen Qing, Ying Xue, Jian-guang Zhang, Zhi-feng Zhang, Jian Liang, Yan Jiang, Yi-ming Liu, Xun LiaoAbstract:Flowers of Rosa chinensis are widely used in traditional Chinese medicine as well as in food industry. Flavonoid glycosides are believed to be the major components in R. chinensis that are responsible for its antioxidant activities. In this work, a liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) method was developed for analysis of Flavonoid glycosides presented in ethyl acetate extract of dried R. chinensis flowers. Twelve Flavonoid glycosides were separated and detected. By comparing the retention times, UV spectra, and tandem MS fragments with those of respective authentic compounds, eight Flavonoid glycosides were unequivocally identified. Although the other four were also identified as Flavonoid glycosides, the glycosylation positions could not be determined due to lack of authentic compounds. Fortunately, the glycosylation effects were clearly observed in the (13)C NMR spectrum of the extract. The detailed structural information was, therefore, obtained to identify the four Flavonoid glycosides as quercetin-3-O-D-glucoside, quercetin-3-O-D-xyloside, kaempferol-3-O-D-xyloside and quercetin-3-O-D-(6″-coumaroyl)-galactoside. These Flavonoid glycosides were detected and identified for the first time in this botanic material. This work reports on the first use of (13)C NMR of a mixture to enhance a rapid HPLC-MS/MS analysis. The proposed analytical protocol was validated with a mixture of authentic Flavonoid glycosides.
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Identification of Flavonoid glycosides in Rosa chinensis Flowers by Liquid Chromatography-tandem Mass Spectrometry in Combination with 13C Nuclear Magnetic Resonance
Journal of chromatography. A, 2012Co-Authors: Lin-sen Qing, Ying Xue, Jian-guang Zhang, Zhi-feng Zhang, Jian Liang, Yan Jiang, Yi-ming Liu, Xun LiaoAbstract:Flowers of Rosa chinensis are widely used in traditional Chinese medicine as well as in food industry. Flavonoid glycosides are believed to be the major components in R. chinensis that are responsible for its antioxidant activities. In this work, a liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) method was developed for analysis of Flavonoid glycosides presented in ethyl acetate extract of dried R. chinensis flowers. Twelve Flavonoid glycosides were separated and detected. By comparing the retention times, UV spectra, and tandem MS fragments with those of respective authentic compounds, eight Flavonoid glycosides were unequivocally identified. Although the other four were also identified as Flavonoid glycosides, the glycosylation positions could not be determined due to lack of authentic compounds. Fortunately, the glycosylation effects were clearly observed in the C-13 NMR spectrum of the extract. The detailed structural information was, therefore, obtained to identify the four Flavonoid glycosides as quercetin-3-O-D-glucoside, quercetin-3-O-D-xyloside, kaempferol-3-O-D-xyloside and quercetin-3-O-D-(6 ''-coumaroyl)-galactoside. These Flavonoid glycosides were detected and identified for the first time in this botanic material. This work reports on the first use of C-13 NMR of a mixture to enhance a rapid HPLC-MS/MS analysis. The proposed analytical protocol was validated with a mixture of authentic Flavonoid glycosides. (C) 2012 Elsevier B.V. All rights reserved.
Sara L. Crockett - One of the best experts on this subject based on the ideXlab platform.
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Flavonoid glycosides and Naphthodianthrones in the Sawfly Tenthredo zonula and its Host-Plants, Hypericum perforatum and H. hirsutum
Journal of Chemical Ecology, 2011Co-Authors: Sara L. Crockett, Jean-luc BoevéAbstract:Larvae of the sawfly Tenthredo zonula are specialized on Hypericum . Whether the sawfly is able to sequester plant metabolites was unknown. Aerial materials of Hypericum perforatum and H. hirsutum , as well as dissected larvae and prepupae of T. zonula , were analyzed by HPLC to determine the presence and content of Flavonoid glycosides (rutin, hyperoside, isoquercitrin, and quercitrin) and naphthodianthrones (pseudohypericin and hypericin). All Flavonoid glycosides were detected in both Hypericum species, with hyperoside as major compound in H. perforatum (ca. 1.7 μmol/g fresh weight, FW) and isoquercitrin in H. hirsutum (0.7 μmol/g FW). Naphthodianthrones were present at low concentrations (0.02 μmol/g FW) in the former, and almost undetected in the latter species. In the body parts (i.e., hemolymph, digestive tract, salivary glands, or miscellaneous organs) of T. zonula , the surveyed compounds were detected more frequently in prepupae than in larvae. The compounds were not present in every sample, and Flavonoid glycosides especially occurred in highly variable amounts, with maximal concentrations of 41 μg rutin/prepupa in salivary glands, 8 μg hyperoside/prepupa in hemolymph (= 0.36 μmol/g FW), 32 μg isoquercitrin/prepupa in salivary glands, and 63 μg quercitrin/larva in miscellaneous organs (mainly composed of the integument). We conclude that Flavonoid glycosides are sequestered since they were detected in organs other than the digestive tract of larvae, and because prepupae are a non-feeding stage. The naphthodianthrone pseudohypericin, but not hypericin, occurred generally in the digestive tract (up to 0.25 μg/larva). Both naphthodianthrones and related unidentified compounds, but not Flavonoid glycosides, were found in the larval excrement. The highly variable distributions of Flavonoid glycosides and naphthodianthrones in T. zonula larvae and prepupae make it difficult to determine the ecological significance of these metabolites.
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Flavonoid glycosides and naphthodianthrones in the sawfly Tenthredo zonula and its host-plants, Hypericum perforatum and H. hirsutum.
Journal of chemical ecology, 2011Co-Authors: Sara L. Crockett, Jean-luc BoevéAbstract:Larvae of the sawfly Tenthredo zonula are specialized on Hypericum. Whether the sawfly is able to sequester plant metabolites was unknown. Aerial materials of Hypericum perforatum and H. hirsutum, as well as dissected larvae and prepupae of T. zonula, were analyzed by HPLC to determine the presence and content of Flavonoid glycosides (rutin, hyperoside, isoquercitrin, and quercitrin) and naphthodianthrones (pseudohypericin and hypericin). All Flavonoid glycosides were detected in both Hypericum species, with hyperoside as major compound in H. perforatum (ca. 1.7 μmol/g fresh weight, FW) and isoquercitrin in H. hirsutum (0.7 μmol/g FW). Naphthodianthrones were present at low concentrations (0.02 μmol/g FW) in the former, and almost undetected in the latter species. In the body parts (i.e., hemolymph, digestive tract, salivary glands, or miscellaneous organs) of T. zonula, the surveyed compounds were detected more frequently in prepupae than in larvae. The compounds were not present in every sample, and Flavonoid glycosides especially occurred in highly variable amounts, with maximal concentrations of 41 μg rutin/prepupa in salivary glands, 8 μg hyperoside/prepupa in hemolymph (= 0.36 μmol/g FW), 32 μg isoquercitrin/prepupa in salivary glands, and 63 μg quercitrin/larva in miscellaneous organs (mainly composed of the integument). We conclude that Flavonoid glycosides are sequestered since they were detected in organs other than the digestive tract of larvae, and because prepupae are a non-feeding stage. The naphthodianthrone pseudohypericin, but not hypericin, occurred generally in the digestive tract (up to 0.25 μg/larva). Both naphthodianthrones and related unidentified compounds, but not Flavonoid glycosides, were found in the larval excrement. The highly variable distributions of Flavonoid glycosides and naphthodianthrones in T. zonula larvae and prepupae make it difficult to determine the ecological significance of these metabolites.