Transformation of Ginsenosides from Notoginseng by Artificial Gastric Juice Can Increase Cytotoxicity toward Cancer Cells
Multicomponent metabolic profile of notoginseng saponins in artificial gastric juice was qualitatively and quantitatively investigated, showing that ginsenosides were transformed via multiple pathways including deglycosylation, dehydration, hydration, and oxygenation. A total of 83 metabolites was i...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2014-03, Vol.62 (12), p.2558-2573 |
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| container_issue | 12 |
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| container_title | Journal of agricultural and food chemistry |
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| creator | Wang, Jing-Rong Yau, Lee Fong Zhang, Rui Xia, Yun Ma, Jing Ho, Hing Man Hu, Ping Hu, Ming Liu, Liang Jiang, Zhi-Hong |
| description | Multicomponent metabolic profile of notoginseng saponins in artificial gastric juice was qualitatively and quantitatively investigated, showing that ginsenosides were transformed via multiple pathways including deglycosylation, dehydration, hydration, and oxygenation. A total of 83 metabolites was identified by using UPLC-Q-TOF-MS, among which 16 new dammarane glycosides were further characterized by comparing with synthesized authentic compounds. Transformation time-course of notoginseng saponins in artificial gastric juice was quantitatively measured for the first time, showing rapid degradation of primary ginsenosides and concomitant formation of deglycosylation, hydration, and dehydration products. It was further demonstrated that the resultant metabolites exhibited enhanced cytotoxicity toward cancer cells. The extensive metabolism of ginsenosides within a transit time span in stomach, together with the formation of metabolites with diversified chemical structures possessing enhanced biological activities, indicated an important role of transformation in gastric juice in the systematic effects of ginsenosides. |
| doi_str_mv | 10.1021/jf405482s |
| format | Article |
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A total of 83 metabolites was identified by using UPLC-Q-TOF-MS, among which 16 new dammarane glycosides were further characterized by comparing with synthesized authentic compounds. Transformation time-course of notoginseng saponins in artificial gastric juice was quantitatively measured for the first time, showing rapid degradation of primary ginsenosides and concomitant formation of deglycosylation, hydration, and dehydration products. It was further demonstrated that the resultant metabolites exhibited enhanced cytotoxicity toward cancer cells. The extensive metabolism of ginsenosides within a transit time span in stomach, together with the formation of metabolites with diversified chemical structures possessing enhanced biological activities, indicated an important role of transformation in gastric juice in the systematic effects of ginsenosides.</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf405482s</identifier><identifier>PMID: 24555416</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Biotransformation ; Cell Line, Tumor ; chemical structure ; Chromatography, High Pressure Liquid ; cytotoxicity ; gastric juice ; Gastric Juice - metabolism ; ginsenosides ; Ginsenosides - chemistry ; Ginsenosides - metabolism ; Ginsenosides - pharmacology ; Humans ; Mass Spectrometry ; metabolism ; metabolites ; Models, Biological ; Molecular Structure ; neoplasm cells ; neoplasms ; Panax notoginseng - chemistry ; Panax notoginseng - metabolism ; Plant Extracts - chemistry ; Plant Extracts - metabolism ; Plant Extracts - pharmacology ; stomach ; Stomach - metabolism</subject><ispartof>Journal of agricultural and food chemistry, 2014-03, Vol.62 (12), p.2558-2573</ispartof><rights>Copyright © 2014 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a405t-b9bf732fe6343ad4707917402fdfcf78c73ec11c9d53d989a293899e245019a43</citedby><cites>FETCH-LOGICAL-a405t-b9bf732fe6343ad4707917402fdfcf78c73ec11c9d53d989a293899e245019a43</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jf405482s$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf405482s$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2764,27075,27923,27924,56737,56787</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24555416$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wang, Jing-Rong</creatorcontrib><creatorcontrib>Yau, Lee Fong</creatorcontrib><creatorcontrib>Zhang, Rui</creatorcontrib><creatorcontrib>Xia, Yun</creatorcontrib><creatorcontrib>Ma, Jing</creatorcontrib><creatorcontrib>Ho, Hing Man</creatorcontrib><creatorcontrib>Hu, Ping</creatorcontrib><creatorcontrib>Hu, Ming</creatorcontrib><creatorcontrib>Liu, Liang</creatorcontrib><creatorcontrib>Jiang, Zhi-Hong</creatorcontrib><title>Transformation of Ginsenosides from Notoginseng by Artificial Gastric Juice Can Increase Cytotoxicity toward Cancer Cells</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>Multicomponent metabolic profile of notoginseng saponins in artificial gastric juice was qualitatively and quantitatively investigated, showing that ginsenosides were transformed via multiple pathways including deglycosylation, dehydration, hydration, and oxygenation. A total of 83 metabolites was identified by using UPLC-Q-TOF-MS, among which 16 new dammarane glycosides were further characterized by comparing with synthesized authentic compounds. Transformation time-course of notoginseng saponins in artificial gastric juice was quantitatively measured for the first time, showing rapid degradation of primary ginsenosides and concomitant formation of deglycosylation, hydration, and dehydration products. It was further demonstrated that the resultant metabolites exhibited enhanced cytotoxicity toward cancer cells. The extensive metabolism of ginsenosides within a transit time span in stomach, together with the formation of metabolites with diversified chemical structures possessing enhanced biological activities, indicated an important role of transformation in gastric juice in the systematic effects of ginsenosides.</description><subject>Biotransformation</subject><subject>Cell Line, Tumor</subject><subject>chemical structure</subject><subject>Chromatography, High Pressure Liquid</subject><subject>cytotoxicity</subject><subject>gastric juice</subject><subject>Gastric Juice - metabolism</subject><subject>ginsenosides</subject><subject>Ginsenosides - chemistry</subject><subject>Ginsenosides - metabolism</subject><subject>Ginsenosides - pharmacology</subject><subject>Humans</subject><subject>Mass Spectrometry</subject><subject>metabolism</subject><subject>metabolites</subject><subject>Models, Biological</subject><subject>Molecular Structure</subject><subject>neoplasm cells</subject><subject>neoplasms</subject><subject>Panax notoginseng - chemistry</subject><subject>Panax notoginseng - metabolism</subject><subject>Plant Extracts - chemistry</subject><subject>Plant Extracts - metabolism</subject><subject>Plant Extracts - pharmacology</subject><subject>stomach</subject><subject>Stomach - metabolism</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0MFu1DAQBmALgehSOPAC4AsSHAIzSbyJj9UKlqIKDrRna9axV15t4uJxRPP2uGzpiZNl-_OM5xfiNcJHhBo_HXwLqu1rfiJWqGqoFGL_VKygXFa9WuOZeMF8AIBedfBcnNWtUqrF9Uos14km9jGNlEOcZPRyGyZ2U-QwOJY-xVF-jznu_57u5W6RFykHH2ygo9wS5xSs_DYH6-SGJnk52eSIy2bJ5dldcXmROf6mNNwD65LcuOORX4pnno7sXj2s5-Lmy-frzdfq6sf2cnNxVVEZKlc7vfNdU3u3btqGhraDTmPXQu0Hb33X265xFtHqQTWD7jXVuum1dmVEQE1tcy7en-repvhrdpzNGNiWH9Dk4swGFUKHoLUu9MOJ2hSZk_PmNoWR0mIQzH3S5jHpYt88lJ13oxse5b9oC3h7Ap6ioX0KbG5-1oBrAETdIBbx7iTIsjnEOU0lh_-0-gPr6o75</recordid><startdate>20140326</startdate><enddate>20140326</enddate><creator>Wang, Jing-Rong</creator><creator>Yau, Lee Fong</creator><creator>Zhang, Rui</creator><creator>Xia, Yun</creator><creator>Ma, Jing</creator><creator>Ho, Hing Man</creator><creator>Hu, Ping</creator><creator>Hu, Ming</creator><creator>Liu, Liang</creator><creator>Jiang, Zhi-Hong</creator><general>American Chemical Society</general><general>American Chemical Society, Books and Journals Division</general><scope>FBQ</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20140326</creationdate><title>Transformation of Ginsenosides from Notoginseng by Artificial Gastric Juice Can Increase Cytotoxicity toward Cancer Cells</title><author>Wang, Jing-Rong ; Yau, Lee Fong ; Zhang, Rui ; Xia, Yun ; Ma, Jing ; Ho, Hing Man ; Hu, Ping ; Hu, Ming ; Liu, Liang ; Jiang, Zhi-Hong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a405t-b9bf732fe6343ad4707917402fdfcf78c73ec11c9d53d989a293899e245019a43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Biotransformation</topic><topic>Cell Line, Tumor</topic><topic>chemical structure</topic><topic>Chromatography, High Pressure Liquid</topic><topic>cytotoxicity</topic><topic>gastric juice</topic><topic>Gastric Juice - metabolism</topic><topic>ginsenosides</topic><topic>Ginsenosides - chemistry</topic><topic>Ginsenosides - metabolism</topic><topic>Ginsenosides - pharmacology</topic><topic>Humans</topic><topic>Mass Spectrometry</topic><topic>metabolism</topic><topic>metabolites</topic><topic>Models, Biological</topic><topic>Molecular Structure</topic><topic>neoplasm cells</topic><topic>neoplasms</topic><topic>Panax notoginseng - chemistry</topic><topic>Panax notoginseng - metabolism</topic><topic>Plant Extracts - chemistry</topic><topic>Plant Extracts - metabolism</topic><topic>Plant Extracts - pharmacology</topic><topic>stomach</topic><topic>Stomach - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Jing-Rong</creatorcontrib><creatorcontrib>Yau, Lee Fong</creatorcontrib><creatorcontrib>Zhang, Rui</creatorcontrib><creatorcontrib>Xia, Yun</creatorcontrib><creatorcontrib>Ma, Jing</creatorcontrib><creatorcontrib>Ho, Hing Man</creatorcontrib><creatorcontrib>Hu, Ping</creatorcontrib><creatorcontrib>Hu, Ming</creatorcontrib><creatorcontrib>Liu, Liang</creatorcontrib><creatorcontrib>Jiang, Zhi-Hong</creatorcontrib><collection>AGRIS</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Jing-Rong</au><au>Yau, Lee Fong</au><au>Zhang, Rui</au><au>Xia, Yun</au><au>Ma, Jing</au><au>Ho, Hing Man</au><au>Hu, Ping</au><au>Hu, Ming</au><au>Liu, Liang</au><au>Jiang, Zhi-Hong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Transformation of Ginsenosides from Notoginseng by Artificial Gastric Juice Can Increase Cytotoxicity toward Cancer Cells</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2014-03-26</date><risdate>2014</risdate><volume>62</volume><issue>12</issue><spage>2558</spage><epage>2573</epage><pages>2558-2573</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><abstract>Multicomponent metabolic profile of notoginseng saponins in artificial gastric juice was qualitatively and quantitatively investigated, showing that ginsenosides were transformed via multiple pathways including deglycosylation, dehydration, hydration, and oxygenation. A total of 83 metabolites was identified by using UPLC-Q-TOF-MS, among which 16 new dammarane glycosides were further characterized by comparing with synthesized authentic compounds. Transformation time-course of notoginseng saponins in artificial gastric juice was quantitatively measured for the first time, showing rapid degradation of primary ginsenosides and concomitant formation of deglycosylation, hydration, and dehydration products. It was further demonstrated that the resultant metabolites exhibited enhanced cytotoxicity toward cancer cells. The extensive metabolism of ginsenosides within a transit time span in stomach, together with the formation of metabolites with diversified chemical structures possessing enhanced biological activities, indicated an important role of transformation in gastric juice in the systematic effects of ginsenosides.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>24555416</pmid><doi>10.1021/jf405482s</doi><tpages>16</tpages></addata></record> |
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| subjects | Biotransformation Cell Line, Tumor chemical structure Chromatography, High Pressure Liquid cytotoxicity gastric juice Gastric Juice - metabolism ginsenosides Ginsenosides - chemistry Ginsenosides - metabolism Ginsenosides - pharmacology Humans Mass Spectrometry metabolism metabolites Models, Biological Molecular Structure neoplasm cells neoplasms Panax notoginseng - chemistry Panax notoginseng - metabolism Plant Extracts - chemistry Plant Extracts - metabolism Plant Extracts - pharmacology stomach Stomach - metabolism |
| title | Transformation of Ginsenosides from Notoginseng by Artificial Gastric Juice Can Increase Cytotoxicity toward Cancer Cells |
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