Structural identification and UPLC-ESI-QTOF-MS2 analysis of flavonoids in the aquatic plant Landoltia punctata and their in vitro and in vivo antioxidant activities

•Apigenin 6-C-[β-D-apiofuranosyl-(1 → 2)]-β-D-glucopyranoside was isolated from L. punctata.•In total, 24 flavone glycosides were identified in L. punctata by UPLC-ESI-QTOF-MS2.•Apigenin 6-C-glycoside exhibited significant in vivo antioxidant activity in C. elegans. Duckweeds have long been consumed...

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Veröffentlicht in:Food chemistry 2021-05, Vol.343, p.128392, Article 128392
Hauptverfasser: Tsolmon, Bolor, Fang, Yang, Yang, Tao, Guo, Ling, He, Kaize, Li, Guo-You, Zhao, Hai
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creator Tsolmon, Bolor
Fang, Yang
Yang, Tao
Guo, Ling
He, Kaize
Li, Guo-You
Zhao, Hai
description •Apigenin 6-C-[β-D-apiofuranosyl-(1 → 2)]-β-D-glucopyranoside was isolated from L. punctata.•In total, 24 flavone glycosides were identified in L. punctata by UPLC-ESI-QTOF-MS2.•Apigenin 6-C-glycoside exhibited significant in vivo antioxidant activity in C. elegans. Duckweeds have long been consumed as vegetables in several South Asian countries. In this study of the chemical constituents of duckweed Landoltia punctata, a new compound, apigenin 6-C-[β-D-apiofuranosyl-(1 → 2)]-β-D-glucopyranoside (1), and a previously LC–MS identified compound, quercetin 3-O-β-D-apiofuranoside (3), as well as three known compounds, luteolin 6-C-[β-D-apiofuranosyl-(1 → 2)]-β-D-glucopyranoside (2), apigenin 6-C-β-D-glucopyranoside (4), and luteolin 7-O-neohespirodise (5), were isolated and identified on the basis of MS and NMR spectroscopic analyses and chemical derivations. In total, 24 flavonoids were identified in L. punctata 0001 by UPLC-ESI-QTOF-MS2. In DPPH and ABTS assays, 3 exhibited significant antioxidant activity with IC50 values of 4.03 ± 1.31 µg/mL and 14.9 ± 2.28 µg/mL, respectively. In in vivo antioxidant activity assays, 1 significantly increased the survival rate of juglone-exposed Caenorhabditis elegans by 2 to 3-fold, and by 75% following thermal damage. Compounds 1–5 exhibited moderate scavenging capacities of intracellular reactive oxygen species in C. elegans exposed to H2O2.
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Duckweeds have long been consumed as vegetables in several South Asian countries. In this study of the chemical constituents of duckweed Landoltia punctata, a new compound, apigenin 6-C-[β-D-apiofuranosyl-(1 → 2)]-β-D-glucopyranoside (1), and a previously LC–MS identified compound, quercetin 3-O-β-D-apiofuranoside (3), as well as three known compounds, luteolin 6-C-[β-D-apiofuranosyl-(1 → 2)]-β-D-glucopyranoside (2), apigenin 6-C-β-D-glucopyranoside (4), and luteolin 7-O-neohespirodise (5), were isolated and identified on the basis of MS and NMR spectroscopic analyses and chemical derivations. In total, 24 flavonoids were identified in L. punctata 0001 by UPLC-ESI-QTOF-MS2. In DPPH and ABTS assays, 3 exhibited significant antioxidant activity with IC50 values of 4.03 ± 1.31 µg/mL and 14.9 ± 2.28 µg/mL, respectively. In in vivo antioxidant activity assays, 1 significantly increased the survival rate of juglone-exposed Caenorhabditis elegans by 2 to 3-fold, and by 75% following thermal damage. 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Duckweeds have long been consumed as vegetables in several South Asian countries. In this study of the chemical constituents of duckweed Landoltia punctata, a new compound, apigenin 6-C-[β-D-apiofuranosyl-(1 → 2)]-β-D-glucopyranoside (1), and a previously LC–MS identified compound, quercetin 3-O-β-D-apiofuranoside (3), as well as three known compounds, luteolin 6-C-[β-D-apiofuranosyl-(1 → 2)]-β-D-glucopyranoside (2), apigenin 6-C-β-D-glucopyranoside (4), and luteolin 7-O-neohespirodise (5), were isolated and identified on the basis of MS and NMR spectroscopic analyses and chemical derivations. In total, 24 flavonoids were identified in L. punctata 0001 by UPLC-ESI-QTOF-MS2. In DPPH and ABTS assays, 3 exhibited significant antioxidant activity with IC50 values of 4.03 ± 1.31 µg/mL and 14.9 ± 2.28 µg/mL, respectively. In in vivo antioxidant activity assays, 1 significantly increased the survival rate of juglone-exposed Caenorhabditis elegans by 2 to 3-fold, and by 75% following thermal damage. Compounds 1–5 exhibited moderate scavenging capacities of intracellular reactive oxygen species in C. elegans exposed to H2O2.</description><subject>Antioxidant activity</subject><subject>Caenorhabditis elegans</subject><subject>Chemistry</subject><subject>Chemistry, Applied</subject><subject>Duckweeds</subject><subject>Flavonoid C-glycoside</subject><subject>Food Science &amp; Technology</subject><subject>Landoltia punctata</subject><subject>Life Sciences &amp; Biomedicine</subject><subject>Nutrition &amp; Dietetics</subject><subject>Physical Sciences</subject><subject>Science &amp; Technology</subject><issn>0308-8146</issn><issn>1873-7072</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>HGBXW</sourceid><recordid>eNqNkc1OGzEYRa2qVUlpX6HyvprUP5kZz45qBAUpiFaBteX4R3zRYKe2J8D79EHxJMAWVrY_3XNtHSP0nZI5JbT5uZm7EIy-tXdzRlgZMsE79gHNqGh51ZKWfUQzwomoBF00R-hLShtCSpKKz-iIc9qVGjZD_1c5jjqPUQ0YjPUZHGiVIXisvME3f5Z9dbq6qP5eX51VlytWpmp4TJBwcNgNahd8AJMweJxvLVb_xgJrvB2Uz3hZKsKQQeHt6HVWWe1LSxDiROwgx7Af7Q-7aV-ufgAz0UpnKAmw6Sv65NSQ7Lfn9RjdnJ1e9-fV8ur3Rf9rWWnW1rmy2jBhBVOcrdWiOCCUckZqpVnDWkO1cJw1TeeorQ3tOkE7Q8Va8La2xqwpP0bNoVfHkFK0Tm4j3Kn4KCmRk3a5kS_a5aRdHrQX8McBvLfr4JIG67V9hYv3htSLtluUHe1KWrw_3UPef0cfRp8LenJAbdGwAxvlM24gWp2lCfDWW58ATOCwGw</recordid><startdate>20210501</startdate><enddate>20210501</enddate><creator>Tsolmon, Bolor</creator><creator>Fang, Yang</creator><creator>Yang, Tao</creator><creator>Guo, Ling</creator><creator>He, Kaize</creator><creator>Li, Guo-You</creator><creator>Zhao, Hai</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>BLEPL</scope><scope>DTL</scope><scope>HGBXW</scope><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-6116-6149</orcidid></search><sort><creationdate>20210501</creationdate><title>Structural identification and UPLC-ESI-QTOF-MS2 analysis of flavonoids in the aquatic plant Landoltia punctata and their in vitro and in vivo antioxidant activities</title><author>Tsolmon, Bolor ; Fang, Yang ; Yang, Tao ; Guo, Ling ; He, Kaize ; Li, Guo-You ; Zhao, Hai</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c275t-ecd28e82a32ba47070113205ac2627d1c8f32669f1e5d199819d18b8375eddb13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Antioxidant activity</topic><topic>Caenorhabditis elegans</topic><topic>Chemistry</topic><topic>Chemistry, Applied</topic><topic>Duckweeds</topic><topic>Flavonoid C-glycoside</topic><topic>Food Science &amp; Technology</topic><topic>Landoltia punctata</topic><topic>Life Sciences &amp; Biomedicine</topic><topic>Nutrition &amp; Dietetics</topic><topic>Physical Sciences</topic><topic>Science &amp; Technology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tsolmon, Bolor</creatorcontrib><creatorcontrib>Fang, Yang</creatorcontrib><creatorcontrib>Yang, Tao</creatorcontrib><creatorcontrib>Guo, Ling</creatorcontrib><creatorcontrib>He, Kaize</creatorcontrib><creatorcontrib>Li, Guo-You</creatorcontrib><creatorcontrib>Zhao, Hai</creatorcontrib><collection>Web of Science Core Collection</collection><collection>Science Citation Index Expanded</collection><collection>Web of Science - Science Citation Index Expanded - 2021</collection><collection>CrossRef</collection><jtitle>Food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tsolmon, Bolor</au><au>Fang, Yang</au><au>Yang, Tao</au><au>Guo, Ling</au><au>He, Kaize</au><au>Li, Guo-You</au><au>Zhao, Hai</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Structural identification and UPLC-ESI-QTOF-MS2 analysis of flavonoids in the aquatic plant Landoltia punctata and their in vitro and in vivo antioxidant activities</atitle><jtitle>Food chemistry</jtitle><stitle>FOOD CHEM</stitle><date>2021-05-01</date><risdate>2021</risdate><volume>343</volume><spage>128392</spage><pages>128392-</pages><artnum>128392</artnum><issn>0308-8146</issn><eissn>1873-7072</eissn><abstract>•Apigenin 6-C-[β-D-apiofuranosyl-(1 → 2)]-β-D-glucopyranoside was isolated from L. punctata.•In total, 24 flavone glycosides were identified in L. punctata by UPLC-ESI-QTOF-MS2.•Apigenin 6-C-glycoside exhibited significant in vivo antioxidant activity in C. elegans. Duckweeds have long been consumed as vegetables in several South Asian countries. In this study of the chemical constituents of duckweed Landoltia punctata, a new compound, apigenin 6-C-[β-D-apiofuranosyl-(1 → 2)]-β-D-glucopyranoside (1), and a previously LC–MS identified compound, quercetin 3-O-β-D-apiofuranoside (3), as well as three known compounds, luteolin 6-C-[β-D-apiofuranosyl-(1 → 2)]-β-D-glucopyranoside (2), apigenin 6-C-β-D-glucopyranoside (4), and luteolin 7-O-neohespirodise (5), were isolated and identified on the basis of MS and NMR spectroscopic analyses and chemical derivations. In total, 24 flavonoids were identified in L. punctata 0001 by UPLC-ESI-QTOF-MS2. In DPPH and ABTS assays, 3 exhibited significant antioxidant activity with IC50 values of 4.03 ± 1.31 µg/mL and 14.9 ± 2.28 µg/mL, respectively. In in vivo antioxidant activity assays, 1 significantly increased the survival rate of juglone-exposed Caenorhabditis elegans by 2 to 3-fold, and by 75% following thermal damage. Compounds 1–5 exhibited moderate scavenging capacities of intracellular reactive oxygen species in C. elegans exposed to H2O2.</abstract><cop>OXFORD</cop><pub>Elsevier Ltd</pub><pmid>33191012</pmid><doi>10.1016/j.foodchem.2020.128392</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0002-6116-6149</orcidid></addata></record>
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subjects Antioxidant activity
Caenorhabditis elegans
Chemistry
Chemistry, Applied
Duckweeds
Flavonoid C-glycoside
Food Science & Technology
Landoltia punctata
Life Sciences & Biomedicine
Nutrition & Dietetics
Physical Sciences
Science & Technology
title Structural identification and UPLC-ESI-QTOF-MS2 analysis of flavonoids in the aquatic plant Landoltia punctata and their in vitro and in vivo antioxidant activities
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