Cucurbitane-Type Triterpenoids from the Fruits of Momordica charantia and Their Cancer Chemopreventive Effects
Thirteen cucurbitane-type triterpene glycosides, including eight new compounds named charantosides I (6), II (7), III (10), IV (11), V (12), VI (13), VII (16), and VIII (17), and five known compounds, 8, 9, 14, 15, and 18, were isolated from a methanol extract of the fruits of Japanese Momordica cha...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2007-08, Vol.70 (8), p.1233-1239 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | Akihisa, Toshihiro Higo, Naoki Tokuda, Harukuni Ukiya, Motohiko Akazawa, Hiroyuki Tochigi, Yuichi Kimura, Yumiko Suzuki, Takashi Nishino, Hoyoku |
| description | Thirteen cucurbitane-type triterpene glycosides, including eight new compounds named charantosides I (6), II (7), III (10), IV (11), V (12), VI (13), VII (16), and VIII (17), and five known compounds, 8, 9, 14, 15, and 18, were isolated from a methanol extract of the fruits of Japanese Momordica charantia. The structures of the new compounds were determined on the basis of spectroscopic methods. On evaluation of these triterpene glycosides and five other cucurbitane-type triterpenes, 1−5, also isolated from the extract of M. charantia fruits, for their inhibitory effects on the induction of Epstein−Barr virus early antigen (EBV-EA) by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells, these compounds showed inhibitory effects on EBV-EA induction with IC50 values of 200−409 mol ratio/32 pmol TPA. In addition, upon evaluation of compounds 1−5 for inhibitory effects against activation of (±)-(E)-methyl-2[(E)-hydroxyimino]-5-nitro-6-methoxy-3-hexemide (NOR 1), a nitrogen oxide (NO) donor, compounds 1−3 showed moderate inhibitory effects. Compounds 1 and 2 exhibited marked inhibitory effects in both 7,12-dimethylbenz[a]anthracene (DMBA)- and peroxynitrite (ONOO-; PN)-induced mouse skin carcinogenesis tests. |
| doi_str_mv | 10.1021/np068075p |
| format | Article |
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The structures of the new compounds were determined on the basis of spectroscopic methods. On evaluation of these triterpene glycosides and five other cucurbitane-type triterpenes, 1−5, also isolated from the extract of M. charantia fruits, for their inhibitory effects on the induction of Epstein−Barr virus early antigen (EBV-EA) by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells, these compounds showed inhibitory effects on EBV-EA induction with IC50 values of 200−409 mol ratio/32 pmol TPA. In addition, upon evaluation of compounds 1−5 for inhibitory effects against activation of (±)-(E)-methyl-2[(E)-hydroxyimino]-5-nitro-6-methoxy-3-hexemide (NOR 1), a nitrogen oxide (NO) donor, compounds 1−3 showed moderate inhibitory effects. Compounds 1 and 2 exhibited marked inhibitory effects in both 7,12-dimethylbenz[a]anthracene (DMBA)- and peroxynitrite (ONOO-; PN)-induced mouse skin carcinogenesis tests.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np068075p</identifier><identifier>PMID: 17685651</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>9,10-Dimethyl-1,2-benzanthracene - pharmacology ; Animals ; anticarcinogenic activity ; Anticarcinogenic Agents - chemistry ; Anticarcinogenic Agents - classification ; Anticarcinogenic Agents - isolation & purification ; Anticarcinogenic Agents - pharmacology ; Antigens, Viral - drug effects ; Biological and medical sciences ; charantoside ; chemical structure ; chemoprevention ; Cucurbitaceae ; cucurbitane triterpenes ; cultured cells ; Fruit - chemistry ; fruits (plant anatomy) ; General pharmacology ; glycosides ; Glycosides - chemistry ; Glycosides - classification ; Glycosides - isolation & purification ; Glycosides - pharmacology ; Humans ; Inhibitory Concentration 50 ; Medical sciences ; medicinal plants ; Mice ; Molecular Structure ; Momordica charantia ; Momordica charantia - chemistry ; Nitric Oxide Donors - pharmacology ; Peroxynitrous Acid - pharmacology ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Plants, Medicinal - chemistry ; Skin Neoplasms - chemically induced ; spectral analysis ; Tetradecanoylphorbol Acetate - pharmacology ; traditional medicine ; Triterpenes - chemistry ; Triterpenes - classification ; Triterpenes - isolation & purification ; Triterpenes - pharmacology ; triterpenoids</subject><ispartof>Journal of natural products (Washington, D.C.), 2007-08, Vol.70 (8), p.1233-1239</ispartof><rights>Copyright © 2007 American Chemical Society and American Society of Pharmacognosy</rights><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a405t-21b3d0cf0a6f0f85af7f43e99b9421b83f3f8ee6c49129696bb0cf446dcb0fce3</citedby><cites>FETCH-LOGICAL-a405t-21b3d0cf0a6f0f85af7f43e99b9421b83f3f8ee6c49129696bb0cf446dcb0fce3</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/np068075p$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np068075p$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=19037299$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17685651$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Akihisa, Toshihiro</creatorcontrib><creatorcontrib>Higo, Naoki</creatorcontrib><creatorcontrib>Tokuda, Harukuni</creatorcontrib><creatorcontrib>Ukiya, Motohiko</creatorcontrib><creatorcontrib>Akazawa, Hiroyuki</creatorcontrib><creatorcontrib>Tochigi, Yuichi</creatorcontrib><creatorcontrib>Kimura, Yumiko</creatorcontrib><creatorcontrib>Suzuki, Takashi</creatorcontrib><creatorcontrib>Nishino, Hoyoku</creatorcontrib><title>Cucurbitane-Type Triterpenoids from the Fruits of Momordica charantia and Their Cancer Chemopreventive Effects</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Thirteen cucurbitane-type triterpene glycosides, including eight new compounds named charantosides I (6), II (7), III (10), IV (11), V (12), VI (13), VII (16), and VIII (17), and five known compounds, 8, 9, 14, 15, and 18, were isolated from a methanol extract of the fruits of Japanese Momordica charantia. The structures of the new compounds were determined on the basis of spectroscopic methods. On evaluation of these triterpene glycosides and five other cucurbitane-type triterpenes, 1−5, also isolated from the extract of M. charantia fruits, for their inhibitory effects on the induction of Epstein−Barr virus early antigen (EBV-EA) by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells, these compounds showed inhibitory effects on EBV-EA induction with IC50 values of 200−409 mol ratio/32 pmol TPA. In addition, upon evaluation of compounds 1−5 for inhibitory effects against activation of (±)-(E)-methyl-2[(E)-hydroxyimino]-5-nitro-6-methoxy-3-hexemide (NOR 1), a nitrogen oxide (NO) donor, compounds 1−3 showed moderate inhibitory effects. Compounds 1 and 2 exhibited marked inhibitory effects in both 7,12-dimethylbenz[a]anthracene (DMBA)- and peroxynitrite (ONOO-; PN)-induced mouse skin carcinogenesis tests.</description><subject>9,10-Dimethyl-1,2-benzanthracene - pharmacology</subject><subject>Animals</subject><subject>anticarcinogenic activity</subject><subject>Anticarcinogenic Agents - chemistry</subject><subject>Anticarcinogenic Agents - classification</subject><subject>Anticarcinogenic Agents - isolation & purification</subject><subject>Anticarcinogenic Agents - pharmacology</subject><subject>Antigens, Viral - drug effects</subject><subject>Biological and medical sciences</subject><subject>charantoside</subject><subject>chemical structure</subject><subject>chemoprevention</subject><subject>Cucurbitaceae</subject><subject>cucurbitane triterpenes</subject><subject>cultured cells</subject><subject>Fruit - chemistry</subject><subject>fruits (plant anatomy)</subject><subject>General pharmacology</subject><subject>glycosides</subject><subject>Glycosides - chemistry</subject><subject>Glycosides - classification</subject><subject>Glycosides - isolation & purification</subject><subject>Glycosides - pharmacology</subject><subject>Humans</subject><subject>Inhibitory Concentration 50</subject><subject>Medical sciences</subject><subject>medicinal plants</subject><subject>Mice</subject><subject>Molecular Structure</subject><subject>Momordica charantia</subject><subject>Momordica charantia - chemistry</subject><subject>Nitric Oxide Donors - pharmacology</subject><subject>Peroxynitrous Acid - pharmacology</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Plants, Medicinal - chemistry</subject><subject>Skin Neoplasms - chemically induced</subject><subject>spectral analysis</subject><subject>Tetradecanoylphorbol Acetate - pharmacology</subject><subject>traditional medicine</subject><subject>Triterpenes - chemistry</subject><subject>Triterpenes - classification</subject><subject>Triterpenes - isolation & purification</subject><subject>Triterpenes - pharmacology</subject><subject>triterpenoids</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0MFu1DAQBmALgehSOPAC4AsHDoFxHDvxEUVdilSgoqngZjnOmHVp4shOKvr2uNpV98JpDv-nGc1PyGsGHxiU7OM0g2ygFvMTsmGihEJCKZ6SDTDJC97I6oS8SOkGADgo8ZycsFo2Qgq2IVO72jX2fjETFt39jLSLfsE44xT8kKiLYaTLDuk2rn5JNDj6NYwhDt4aancmmmnxhpppoN0OfaStmSzmscMxzBHvMOd3SM-cQ7ukl-SZM7cJXx3mKbnennXteXHx_fOX9tNFYSoQS1Gyng9gHRjpwDXCuNpVHJXqVZWzhjvuGkRpK8VKJZXs-6yrSg62B2eRn5L3-702hpQiOj1HP5p4rxnoh870Y2fZvtnbee1HHI7yUFIG7w7AJGtuXf7Z-nR0CnhdKpVdsXc-Lfj3MTfxj5Y1r4XuLq90-7O9_PZr-0M32b_de2eCNr9j3nl9VQLjAA0TooLjZWOTvglrnHJp_3nhH_Bfmpk</recordid><startdate>20070801</startdate><enddate>20070801</enddate><creator>Akihisa, Toshihiro</creator><creator>Higo, Naoki</creator><creator>Tokuda, Harukuni</creator><creator>Ukiya, Motohiko</creator><creator>Akazawa, Hiroyuki</creator><creator>Tochigi, Yuichi</creator><creator>Kimura, Yumiko</creator><creator>Suzuki, Takashi</creator><creator>Nishino, Hoyoku</creator><general>American Chemical Society</general><general>American Society of Pharmacognosy</general><scope>FBQ</scope><scope>BSCLL</scope><scope>IQODW</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></search><sort><creationdate>20070801</creationdate><title>Cucurbitane-Type Triterpenoids from the Fruits of Momordica charantia and Their Cancer Chemopreventive Effects</title><author>Akihisa, Toshihiro ; Higo, Naoki ; Tokuda, Harukuni ; Ukiya, Motohiko ; Akazawa, Hiroyuki ; Tochigi, Yuichi ; Kimura, Yumiko ; Suzuki, Takashi ; Nishino, Hoyoku</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a405t-21b3d0cf0a6f0f85af7f43e99b9421b83f3f8ee6c49129696bb0cf446dcb0fce3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>9,10-Dimethyl-1,2-benzanthracene - pharmacology</topic><topic>Animals</topic><topic>anticarcinogenic activity</topic><topic>Anticarcinogenic Agents - chemistry</topic><topic>Anticarcinogenic Agents - classification</topic><topic>Anticarcinogenic Agents - isolation & purification</topic><topic>Anticarcinogenic Agents - pharmacology</topic><topic>Antigens, Viral - drug effects</topic><topic>Biological and medical sciences</topic><topic>charantoside</topic><topic>chemical structure</topic><topic>chemoprevention</topic><topic>Cucurbitaceae</topic><topic>cucurbitane triterpenes</topic><topic>cultured cells</topic><topic>Fruit - chemistry</topic><topic>fruits (plant anatomy)</topic><topic>General pharmacology</topic><topic>glycosides</topic><topic>Glycosides - chemistry</topic><topic>Glycosides - classification</topic><topic>Glycosides - isolation & purification</topic><topic>Glycosides - pharmacology</topic><topic>Humans</topic><topic>Inhibitory Concentration 50</topic><topic>Medical sciences</topic><topic>medicinal plants</topic><topic>Mice</topic><topic>Molecular Structure</topic><topic>Momordica charantia</topic><topic>Momordica charantia - chemistry</topic><topic>Nitric Oxide Donors - pharmacology</topic><topic>Peroxynitrous Acid - pharmacology</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Plants, Medicinal - chemistry</topic><topic>Skin Neoplasms - chemically induced</topic><topic>spectral analysis</topic><topic>Tetradecanoylphorbol Acetate - pharmacology</topic><topic>traditional medicine</topic><topic>Triterpenes - chemistry</topic><topic>Triterpenes - classification</topic><topic>Triterpenes - isolation & purification</topic><topic>Triterpenes - pharmacology</topic><topic>triterpenoids</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Akihisa, Toshihiro</creatorcontrib><creatorcontrib>Higo, Naoki</creatorcontrib><creatorcontrib>Tokuda, Harukuni</creatorcontrib><creatorcontrib>Ukiya, Motohiko</creatorcontrib><creatorcontrib>Akazawa, Hiroyuki</creatorcontrib><creatorcontrib>Tochigi, Yuichi</creatorcontrib><creatorcontrib>Kimura, Yumiko</creatorcontrib><creatorcontrib>Suzuki, Takashi</creatorcontrib><creatorcontrib>Nishino, Hoyoku</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Akihisa, Toshihiro</au><au>Higo, Naoki</au><au>Tokuda, Harukuni</au><au>Ukiya, Motohiko</au><au>Akazawa, Hiroyuki</au><au>Tochigi, Yuichi</au><au>Kimura, Yumiko</au><au>Suzuki, Takashi</au><au>Nishino, Hoyoku</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cucurbitane-Type Triterpenoids from the Fruits of Momordica charantia and Their Cancer Chemopreventive Effects</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2007-08-01</date><risdate>2007</risdate><volume>70</volume><issue>8</issue><spage>1233</spage><epage>1239</epage><pages>1233-1239</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>Thirteen cucurbitane-type triterpene glycosides, including eight new compounds named charantosides I (6), II (7), III (10), IV (11), V (12), VI (13), VII (16), and VIII (17), and five known compounds, 8, 9, 14, 15, and 18, were isolated from a methanol extract of the fruits of Japanese Momordica charantia. The structures of the new compounds were determined on the basis of spectroscopic methods. On evaluation of these triterpene glycosides and five other cucurbitane-type triterpenes, 1−5, also isolated from the extract of M. charantia fruits, for their inhibitory effects on the induction of Epstein−Barr virus early antigen (EBV-EA) by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells, these compounds showed inhibitory effects on EBV-EA induction with IC50 values of 200−409 mol ratio/32 pmol TPA. In addition, upon evaluation of compounds 1−5 for inhibitory effects against activation of (±)-(E)-methyl-2[(E)-hydroxyimino]-5-nitro-6-methoxy-3-hexemide (NOR 1), a nitrogen oxide (NO) donor, compounds 1−3 showed moderate inhibitory effects. Compounds 1 and 2 exhibited marked inhibitory effects in both 7,12-dimethylbenz[a]anthracene (DMBA)- and peroxynitrite (ONOO-; PN)-induced mouse skin carcinogenesis tests.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>17685651</pmid><doi>10.1021/np068075p</doi><tpages>7</tpages></addata></record> |
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| ispartof | Journal of natural products (Washington, D.C.), 2007-08, Vol.70 (8), p.1233-1239 |
| issn | 0163-3864 1520-6025 |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | 9,10-Dimethyl-1,2-benzanthracene - pharmacology Animals anticarcinogenic activity Anticarcinogenic Agents - chemistry Anticarcinogenic Agents - classification Anticarcinogenic Agents - isolation & purification Anticarcinogenic Agents - pharmacology Antigens, Viral - drug effects Biological and medical sciences charantoside chemical structure chemoprevention Cucurbitaceae cucurbitane triterpenes cultured cells Fruit - chemistry fruits (plant anatomy) General pharmacology glycosides Glycosides - chemistry Glycosides - classification Glycosides - isolation & purification Glycosides - pharmacology Humans Inhibitory Concentration 50 Medical sciences medicinal plants Mice Molecular Structure Momordica charantia Momordica charantia - chemistry Nitric Oxide Donors - pharmacology Peroxynitrous Acid - pharmacology Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Plants, Medicinal - chemistry Skin Neoplasms - chemically induced spectral analysis Tetradecanoylphorbol Acetate - pharmacology traditional medicine Triterpenes - chemistry Triterpenes - classification Triterpenes - isolation & purification Triterpenes - pharmacology triterpenoids |
| title | Cucurbitane-Type Triterpenoids from the Fruits of Momordica charantia and Their Cancer Chemopreventive Effects |
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