Stability and Cytotoxicity of Gambogic Acid and Its Derivative, Gambogoic Acid
In this study, the stability of gambogic acid (GA), a polyprenylated xanthone with potent cytotoxicities against various cancer cell lines, was evaluated under several experimental conditions including addition of acids, alkalis and organic solvents. GA was stable when dissolved in acetone, acetonit...
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| Veröffentlicht in: | Biological & Pharmaceutical Bulletin 2005, Vol.28(12), pp.2335-2337 |
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| creator | Han, Quan-Bin Cheung, Susan Tai, Joseph Qiao, Chun-Feng Song, Jing-Zheng Xu, Hong-Xi |
| description | In this study, the stability of gambogic acid (GA), a polyprenylated xanthone with potent cytotoxicities against various cancer cell lines, was evaluated under several experimental conditions including addition of acids, alkalis and organic solvents. GA was stable when dissolved in acetone, acetonitrile, and chloroform, even when acids were added. However, a new derivative was produced after GA was stored in the methanol solution for a week at room temperature. The addition of alkalis could increase the rate of this chemical transformation. This derivative was determined to be gambogoic acid (GOA) by the HPLC-MS comparison with the known compound. GOA was proposed to be the product of neuclophilic addition of methanol to the olefinic bond at C-10 of GA. Furthermore, when these two compounds were tested for their cytotoxicity, GOA showed significantly weaker inhibitory effects than GA. It was therefore deduced that the α,β-unsaturated carbonyl moiety at C-10 contributed to the cytotoxicity of gambogic acid. |
| doi_str_mv | 10.1248/bpb.28.2335 |
| format | Article |
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GA was stable when dissolved in acetone, acetonitrile, and chloroform, even when acids were added. However, a new derivative was produced after GA was stored in the methanol solution for a week at room temperature. The addition of alkalis could increase the rate of this chemical transformation. This derivative was determined to be gambogoic acid (GOA) by the HPLC-MS comparison with the known compound. GOA was proposed to be the product of neuclophilic addition of methanol to the olefinic bond at C-10 of GA. Furthermore, when these two compounds were tested for their cytotoxicity, GOA showed significantly weaker inhibitory effects than GA. It was therefore deduced that the α,β-unsaturated carbonyl moiety at C-10 contributed to the cytotoxicity of gambogic acid.</description><identifier>ISSN: 0918-6158</identifier><identifier>EISSN: 1347-5215</identifier><identifier>DOI: 10.1248/bpb.28.2335</identifier><identifier>PMID: 16327177</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>Antineoplastic Agents - chemistry ; Antineoplastic Agents - isolation & purification ; Antineoplastic Agents - pharmacology ; Cell Line, Tumor ; Cell Proliferation - drug effects ; Cell Survival - drug effects ; Chromatography, High Pressure Liquid ; cytotoxicity ; Drug Screening Assays, Antitumor - methods ; Drug Stability ; gambogic acid ; gambogoic acid ; Garcinia hanburyi ; Humans ; Inhibitory Concentration 50 ; Methanol ; Resins, Plant - pharmacology ; Spectrometry, Mass, Electrospray Ionization ; stability ; Xanthones - chemistry ; Xanthones - isolation & purification ; Xanthones - pharmacology ; Xanthones - toxicity</subject><ispartof>Biological and Pharmaceutical Bulletin, 2005, Vol.28(12), pp.2335-2337</ispartof><rights>2005 The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 2005</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c691t-b22d8536b08d610e6910f83bd89e9c05d391f2e73612f4fa587c0a2c5a6beed33</citedby><cites>FETCH-LOGICAL-c691t-b22d8536b08d610e6910f83bd89e9c05d391f2e73612f4fa587c0a2c5a6beed33</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1877,4010,27900,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16327177$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Han, Quan-Bin</creatorcontrib><creatorcontrib>Cheung, Susan</creatorcontrib><creatorcontrib>Tai, Joseph</creatorcontrib><creatorcontrib>Qiao, Chun-Feng</creatorcontrib><creatorcontrib>Song, Jing-Zheng</creatorcontrib><creatorcontrib>Xu, Hong-Xi</creatorcontrib><creatorcontrib>University of British Columbia</creatorcontrib><creatorcontrib>Hong Kong Jockey Club Institute of Chinese Medicine</creatorcontrib><creatorcontrib>Children's and Family Research Institute</creatorcontrib><creatorcontrib>bDepartments of Pathology and Pediatrics</creatorcontrib><creatorcontrib>Center for Complementary Medicine Research</creatorcontrib><creatorcontrib>aChinese Medicine Laboratory</creatorcontrib><title>Stability and Cytotoxicity of Gambogic Acid and Its Derivative, Gambogoic Acid</title><title>Biological & Pharmaceutical Bulletin</title><addtitle>Biol Pharm Bull</addtitle><description>In this study, the stability of gambogic acid (GA), a polyprenylated xanthone with potent cytotoxicities against various cancer cell lines, was evaluated under several experimental conditions including addition of acids, alkalis and organic solvents. GA was stable when dissolved in acetone, acetonitrile, and chloroform, even when acids were added. However, a new derivative was produced after GA was stored in the methanol solution for a week at room temperature. The addition of alkalis could increase the rate of this chemical transformation. This derivative was determined to be gambogoic acid (GOA) by the HPLC-MS comparison with the known compound. GOA was proposed to be the product of neuclophilic addition of methanol to the olefinic bond at C-10 of GA. Furthermore, when these two compounds were tested for their cytotoxicity, GOA showed significantly weaker inhibitory effects than GA. It was therefore deduced that the α,β-unsaturated carbonyl moiety at C-10 contributed to the cytotoxicity of gambogic acid.</description><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - isolation & purification</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>Cell Survival - drug effects</subject><subject>Chromatography, High Pressure Liquid</subject><subject>cytotoxicity</subject><subject>Drug Screening Assays, Antitumor - methods</subject><subject>Drug Stability</subject><subject>gambogic acid</subject><subject>gambogoic acid</subject><subject>Garcinia hanburyi</subject><subject>Humans</subject><subject>Inhibitory Concentration 50</subject><subject>Methanol</subject><subject>Resins, Plant - pharmacology</subject><subject>Spectrometry, Mass, Electrospray Ionization</subject><subject>stability</subject><subject>Xanthones - chemistry</subject><subject>Xanthones - isolation & purification</subject><subject>Xanthones - pharmacology</subject><subject>Xanthones - toxicity</subject><issn>0918-6158</issn><issn>1347-5215</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkE1v1DAQhq0K1G4LJ-5VJI6Q7diOP3IsC10qVeUAnC3bcYpX2Xhreyv23-N0U3oZSzOPnxm9CH3AsMSkkVdmZ5ZELgml7AQtMG1EzQhmb9ACWixrjpk8Q-cpbQBAAKGn6AxzSgQWYoHuf2Zt_ODzodJjV60OOeTw19upEfpqrbcmPHhbXVvfPRO3OVVfXfRPOvsn93kmwoy8Q297PST3fn4v0O-bb79W3-u7H-vb1fVdbXmLc20I6SSj3IDsOAZXmtBLajrZutYC62iLe-IE5Zj0Ta-ZFBY0sUxz41xH6QX6ePTuYnjcu5TVJuzjWFYq3DQtZZJyKNSnI2VjSCm6Xu2i3-p4UBjUlJ0q2Ski1ZRdoS9n595sXffKzmEVYH0EytRbPYRx8KN73WyTMD4MQREApgCIxEQBpc_6qQgMQnDcFtOXo2mTsn5w_1fpmL0d3MtZ5ftcJ8HL0P7RUbmR_gNTz5ZL</recordid><startdate>2005</startdate><enddate>2005</enddate><creator>Han, Quan-Bin</creator><creator>Cheung, Susan</creator><creator>Tai, Joseph</creator><creator>Qiao, Chun-Feng</creator><creator>Song, Jing-Zheng</creator><creator>Xu, Hong-Xi</creator><general>The Pharmaceutical Society of Japan</general><general>Pharmaceutical Society of Japan</general><general>Japan Science and Technology Agency</general><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>7QP</scope><scope>7QR</scope><scope>7TK</scope><scope>7U9</scope><scope>8FD</scope><scope>FR3</scope><scope>H94</scope><scope>P64</scope></search><sort><creationdate>2005</creationdate><title>Stability and Cytotoxicity of Gambogic Acid and Its Derivative, Gambogoic Acid</title><author>Han, Quan-Bin ; Cheung, Susan ; Tai, Joseph ; Qiao, Chun-Feng ; Song, Jing-Zheng ; Xu, Hong-Xi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c691t-b22d8536b08d610e6910f83bd89e9c05d391f2e73612f4fa587c0a2c5a6beed33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - isolation & purification</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation - drug effects</topic><topic>Cell Survival - drug effects</topic><topic>Chromatography, High Pressure Liquid</topic><topic>cytotoxicity</topic><topic>Drug Screening Assays, Antitumor - methods</topic><topic>Drug Stability</topic><topic>gambogic acid</topic><topic>gambogoic acid</topic><topic>Garcinia hanburyi</topic><topic>Humans</topic><topic>Inhibitory Concentration 50</topic><topic>Methanol</topic><topic>Resins, Plant - pharmacology</topic><topic>Spectrometry, Mass, Electrospray Ionization</topic><topic>stability</topic><topic>Xanthones - chemistry</topic><topic>Xanthones - isolation & purification</topic><topic>Xanthones - pharmacology</topic><topic>Xanthones - toxicity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Han, Quan-Bin</creatorcontrib><creatorcontrib>Cheung, Susan</creatorcontrib><creatorcontrib>Tai, Joseph</creatorcontrib><creatorcontrib>Qiao, Chun-Feng</creatorcontrib><creatorcontrib>Song, Jing-Zheng</creatorcontrib><creatorcontrib>Xu, Hong-Xi</creatorcontrib><creatorcontrib>University of British Columbia</creatorcontrib><creatorcontrib>Hong Kong Jockey Club Institute of Chinese Medicine</creatorcontrib><creatorcontrib>Children's and Family Research Institute</creatorcontrib><creatorcontrib>bDepartments of Pathology and Pediatrics</creatorcontrib><creatorcontrib>Center for Complementary Medicine Research</creatorcontrib><creatorcontrib>aChinese Medicine Laboratory</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Calcium & Calcified Tissue Abstracts</collection><collection>Chemoreception Abstracts</collection><collection>Neurosciences Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Biological & Pharmaceutical Bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Han, Quan-Bin</au><au>Cheung, Susan</au><au>Tai, Joseph</au><au>Qiao, Chun-Feng</au><au>Song, Jing-Zheng</au><au>Xu, Hong-Xi</au><aucorp>University of British Columbia</aucorp><aucorp>Hong Kong Jockey Club Institute of Chinese Medicine</aucorp><aucorp>Children's and Family Research Institute</aucorp><aucorp>bDepartments of Pathology and Pediatrics</aucorp><aucorp>Center for Complementary Medicine Research</aucorp><aucorp>aChinese Medicine Laboratory</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Stability and Cytotoxicity of Gambogic Acid and Its Derivative, Gambogoic Acid</atitle><jtitle>Biological & Pharmaceutical Bulletin</jtitle><addtitle>Biol Pharm Bull</addtitle><date>2005</date><risdate>2005</risdate><volume>28</volume><issue>12</issue><spage>2335</spage><epage>2337</epage><pages>2335-2337</pages><issn>0918-6158</issn><eissn>1347-5215</eissn><abstract>In this study, the stability of gambogic acid (GA), a polyprenylated xanthone with potent cytotoxicities against various cancer cell lines, was evaluated under several experimental conditions including addition of acids, alkalis and organic solvents. GA was stable when dissolved in acetone, acetonitrile, and chloroform, even when acids were added. However, a new derivative was produced after GA was stored in the methanol solution for a week at room temperature. The addition of alkalis could increase the rate of this chemical transformation. This derivative was determined to be gambogoic acid (GOA) by the HPLC-MS comparison with the known compound. GOA was proposed to be the product of neuclophilic addition of methanol to the olefinic bond at C-10 of GA. Furthermore, when these two compounds were tested for their cytotoxicity, GOA showed significantly weaker inhibitory effects than GA. It was therefore deduced that the α,β-unsaturated carbonyl moiety at C-10 contributed to the cytotoxicity of gambogic acid.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>16327177</pmid><doi>10.1248/bpb.28.2335</doi><tpages>3</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Antineoplastic Agents - chemistry Antineoplastic Agents - isolation & purification Antineoplastic Agents - pharmacology Cell Line, Tumor Cell Proliferation - drug effects Cell Survival - drug effects Chromatography, High Pressure Liquid cytotoxicity Drug Screening Assays, Antitumor - methods Drug Stability gambogic acid gambogoic acid Garcinia hanburyi Humans Inhibitory Concentration 50 Methanol Resins, Plant - pharmacology Spectrometry, Mass, Electrospray Ionization stability Xanthones - chemistry Xanthones - isolation & purification Xanthones - pharmacology Xanthones - toxicity |
| title | Stability and Cytotoxicity of Gambogic Acid and Its Derivative, Gambogoic Acid |
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