Sesquiterpenes from Clove (Eugenia caryophyllata) as Potential Anticarcinogenic Agents
Bioassay-directed fractionation of clove terpenes from the plant Eugenia caryophyllata has led to the isolation of the following five active known compounds: beta-caryophyllene [1], beta-caryophyllene oxide [2], alpha-humulene [3], alpha-humulene epoxide I [4], and eugenol [5]. Their structures were...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 1992-07, Vol.55 (7), p.999-1003 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | Zheng, Guo-Qiang Kenney, Patrick M Lam, Luke K. T |
| description | Bioassay-directed fractionation of clove terpenes from the plant Eugenia caryophyllata has led to the isolation of the following five active known compounds: beta-caryophyllene [1], beta-caryophyllene oxide [2], alpha-humulene [3], alpha-humulene epoxide I [4], and eugenol [5]. Their structures were determined on the basis of spectral analysis (hreims, 1H and 13C nmr). These compounds showed significant activity as inducers of the detoxifying enzyme glutathione S-transferase in the mouse liver and small intestine. The ability of natural anticarcinogens to induce detoxifying enzymes has been found to correlate with their activity in the inhibition of chemical carcinogenesis. Thus, these sesquiterpenes show promise as potential anticarcinogenic agents. |
| doi_str_mv | 10.1021/np50085a029 |
| format | Article |
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T</creator><creatorcontrib>Zheng, Guo-Qiang ; Kenney, Patrick M ; Lam, Luke K. T</creatorcontrib><description>Bioassay-directed fractionation of clove terpenes from the plant Eugenia caryophyllata has led to the isolation of the following five active known compounds: beta-caryophyllene [1], beta-caryophyllene oxide [2], alpha-humulene [3], alpha-humulene epoxide I [4], and eugenol [5]. Their structures were determined on the basis of spectral analysis (hreims, 1H and 13C nmr). These compounds showed significant activity as inducers of the detoxifying enzyme glutathione S-transferase in the mouse liver and small intestine. The ability of natural anticarcinogens to induce detoxifying enzymes has been found to correlate with their activity in the inhibition of chemical carcinogenesis. Thus, these sesquiterpenes show promise as potential anticarcinogenic agents.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np50085a029</identifier><identifier>PMID: 1402962</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>ALPHA-HUMULENE ; ALPHA-HUMULENE EPOXIDE ; Animals ; Antineoplastic Agents - isolation & purification ; BETA-CARYOPHYLLENE ; BETA-CARYOPHYLLENE OXIDE ; Biological and medical sciences ; CARCINOGENESIS ; CARCINOGENOS ; CARCINOGENS ; COMPOSE PHENOLIQUE ; COMPUESTOS FENOLICOS ; Cytosol - enzymology ; DESINTOXICACION ; DETOXIFICATION ; ESTIMULO ; EUGENIA ; EUGENOL ; Female ; FOIE ; Gastric Mucosa - enzymology ; General pharmacology ; GLUTATHIONE TRANSFERASE ; Glutathione Transferase - metabolism ; HIGADO ; INTESTIN ; Intestinal Mucosa - enzymology ; INTESTINES ; INTESTINOS ; LIVER ; Liver - enzymology ; Medical sciences ; METABOLIC DETOXIFICATION ; METABOLISM ; METABOLISME ; METABOLISMO ; MICE ; Mice, Inbred A ; NEOPLASMAS ; NEOPLASME ; NEOPLASMS ; Pharmacognosy. 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Drug treatments ; PHENOLIC COMPOUNDS ; Plants, Medicinal ; RATON ; Sesquiterpenes - chemistry ; Sesquiterpenes - isolation & purification ; Sesquiterpenes - pharmacology ; SESQUITERPENOIDE ; SESQUITERPENOIDS ; SESQUITERPENOS ; SMALL INTESTINE ; SOURIS ; Spices ; STIMULATION ; STIMULI ; STIMULUS ; SUBSTANCE CANCERIGENE ; TRANSFERASAS ; TRANSFERASE ; TRANSFERASES</subject><ispartof>Journal of natural products (Washington, D.C.), 1992-07, Vol.55 (7), p.999-1003</ispartof><rights>1992 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a402t-f50e46ef4b86cc52ee6a7e66a973501eb8e569490b2525b17400011b66927cac3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/np50085a029$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np50085a029$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=5462468$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/1402962$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zheng, Guo-Qiang</creatorcontrib><creatorcontrib>Kenney, Patrick M</creatorcontrib><creatorcontrib>Lam, Luke K. T</creatorcontrib><title>Sesquiterpenes from Clove (Eugenia caryophyllata) as Potential Anticarcinogenic Agents</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Bioassay-directed fractionation of clove terpenes from the plant Eugenia caryophyllata has led to the isolation of the following five active known compounds: beta-caryophyllene [1], beta-caryophyllene oxide [2], alpha-humulene [3], alpha-humulene epoxide I [4], and eugenol [5]. Their structures were determined on the basis of spectral analysis (hreims, 1H and 13C nmr). These compounds showed significant activity as inducers of the detoxifying enzyme glutathione S-transferase in the mouse liver and small intestine. The ability of natural anticarcinogens to induce detoxifying enzymes has been found to correlate with their activity in the inhibition of chemical carcinogenesis. Thus, these sesquiterpenes show promise as potential anticarcinogenic agents.</description><subject>ALPHA-HUMULENE</subject><subject>ALPHA-HUMULENE EPOXIDE</subject><subject>Animals</subject><subject>Antineoplastic Agents - isolation & purification</subject><subject>BETA-CARYOPHYLLENE</subject><subject>BETA-CARYOPHYLLENE OXIDE</subject><subject>Biological and medical sciences</subject><subject>CARCINOGENESIS</subject><subject>CARCINOGENOS</subject><subject>CARCINOGENS</subject><subject>COMPOSE PHENOLIQUE</subject><subject>COMPUESTOS FENOLICOS</subject><subject>Cytosol - enzymology</subject><subject>DESINTOXICACION</subject><subject>DETOXIFICATION</subject><subject>ESTIMULO</subject><subject>EUGENIA</subject><subject>EUGENOL</subject><subject>Female</subject><subject>FOIE</subject><subject>Gastric Mucosa - enzymology</subject><subject>General pharmacology</subject><subject>GLUTATHIONE TRANSFERASE</subject><subject>Glutathione Transferase - metabolism</subject><subject>HIGADO</subject><subject>INTESTIN</subject><subject>Intestinal Mucosa - enzymology</subject><subject>INTESTINES</subject><subject>INTESTINOS</subject><subject>LIVER</subject><subject>Liver - enzymology</subject><subject>Medical sciences</subject><subject>METABOLIC DETOXIFICATION</subject><subject>METABOLISM</subject><subject>METABOLISME</subject><subject>METABOLISMO</subject><subject>MICE</subject><subject>Mice, Inbred A</subject><subject>NEOPLASMAS</subject><subject>NEOPLASME</subject><subject>NEOPLASMS</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>PHENOLIC COMPOUNDS</subject><subject>Plants, Medicinal</subject><subject>RATON</subject><subject>Sesquiterpenes - chemistry</subject><subject>Sesquiterpenes - isolation & purification</subject><subject>Sesquiterpenes - pharmacology</subject><subject>SESQUITERPENOIDE</subject><subject>SESQUITERPENOIDS</subject><subject>SESQUITERPENOS</subject><subject>SMALL INTESTINE</subject><subject>SOURIS</subject><subject>Spices</subject><subject>STIMULATION</subject><subject>STIMULI</subject><subject>STIMULUS</subject><subject>SUBSTANCE CANCERIGENE</subject><subject>TRANSFERASAS</subject><subject>TRANSFERASE</subject><subject>TRANSFERASES</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1992</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMFL3EAUxgep6Lr15K1QyEFQKdE3M5lJclwW7RYEpbsui5fhZfpiY7NJnMlK97_vSER78PQdfj8e3_sYO-JwzkHwi6ZTAJlCEPkOG3ElINYg1Cc2Aq5lLDOd7LMD7x8BQEKu9tgeT4KsxYgt5-SfNlVPrqOGfFS6dh1N6_aZotPLzQM1FUYW3bbtfm_rGns8i9BHt21PTV9hHU1CBG6rpn2RbTQJ0fvPbLfE2tPha47Z3dXlYjqLr2--_5hOrmMMBfq4VECJpjIpMm2tEkQaU9Ia81Qq4FRkpHSe5FAIJVTB0yS8wHmhdS5Si1aO2bfhrnWt945K07lqHfoaDuZlHPPfOMH-OtjdpljTr3d3WCPw41eO3mJdOmxs5d80lWiR6Cxo8aBVvqe_bxjdH6NTmSqzuJ2b5WK2-pkvV-Y--F8Gv8TW4IMLJ-_muZQSUhXgyQDRevPYblwT9vqw_T-hl4_5</recordid><startdate>19920701</startdate><enddate>19920701</enddate><creator>Zheng, Guo-Qiang</creator><creator>Kenney, Patrick M</creator><creator>Lam, Luke K. T</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>19920701</creationdate><title>Sesquiterpenes from Clove (Eugenia caryophyllata) as Potential Anticarcinogenic Agents</title><author>Zheng, Guo-Qiang ; Kenney, Patrick M ; Lam, Luke K. T</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a402t-f50e46ef4b86cc52ee6a7e66a973501eb8e569490b2525b17400011b66927cac3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1992</creationdate><topic>ALPHA-HUMULENE</topic><topic>ALPHA-HUMULENE EPOXIDE</topic><topic>Animals</topic><topic>Antineoplastic Agents - isolation & purification</topic><topic>BETA-CARYOPHYLLENE</topic><topic>BETA-CARYOPHYLLENE OXIDE</topic><topic>Biological and medical sciences</topic><topic>CARCINOGENESIS</topic><topic>CARCINOGENOS</topic><topic>CARCINOGENS</topic><topic>COMPOSE PHENOLIQUE</topic><topic>COMPUESTOS FENOLICOS</topic><topic>Cytosol - enzymology</topic><topic>DESINTOXICACION</topic><topic>DETOXIFICATION</topic><topic>ESTIMULO</topic><topic>EUGENIA</topic><topic>EUGENOL</topic><topic>Female</topic><topic>FOIE</topic><topic>Gastric Mucosa - enzymology</topic><topic>General pharmacology</topic><topic>GLUTATHIONE TRANSFERASE</topic><topic>Glutathione Transferase - metabolism</topic><topic>HIGADO</topic><topic>INTESTIN</topic><topic>Intestinal Mucosa - enzymology</topic><topic>INTESTINES</topic><topic>INTESTINOS</topic><topic>LIVER</topic><topic>Liver - enzymology</topic><topic>Medical sciences</topic><topic>METABOLIC DETOXIFICATION</topic><topic>METABOLISM</topic><topic>METABOLISME</topic><topic>METABOLISMO</topic><topic>MICE</topic><topic>Mice, Inbred A</topic><topic>NEOPLASMAS</topic><topic>NEOPLASME</topic><topic>NEOPLASMS</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>PHENOLIC COMPOUNDS</topic><topic>Plants, Medicinal</topic><topic>RATON</topic><topic>Sesquiterpenes - chemistry</topic><topic>Sesquiterpenes - isolation & purification</topic><topic>Sesquiterpenes - pharmacology</topic><topic>SESQUITERPENOIDE</topic><topic>SESQUITERPENOIDS</topic><topic>SESQUITERPENOS</topic><topic>SMALL INTESTINE</topic><topic>SOURIS</topic><topic>Spices</topic><topic>STIMULATION</topic><topic>STIMULI</topic><topic>STIMULUS</topic><topic>SUBSTANCE CANCERIGENE</topic><topic>TRANSFERASAS</topic><topic>TRANSFERASE</topic><topic>TRANSFERASES</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zheng, Guo-Qiang</creatorcontrib><creatorcontrib>Kenney, Patrick M</creatorcontrib><creatorcontrib>Lam, Luke K. T</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>Zheng, Guo-Qiang</au><au>Kenney, Patrick M</au><au>Lam, Luke K. T</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Sesquiterpenes from Clove (Eugenia caryophyllata) as Potential Anticarcinogenic Agents</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>1992-07-01</date><risdate>1992</risdate><volume>55</volume><issue>7</issue><spage>999</spage><epage>1003</epage><pages>999-1003</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>Bioassay-directed fractionation of clove terpenes from the plant Eugenia caryophyllata has led to the isolation of the following five active known compounds: beta-caryophyllene [1], beta-caryophyllene oxide [2], alpha-humulene [3], alpha-humulene epoxide I [4], and eugenol [5]. Their structures were determined on the basis of spectral analysis (hreims, 1H and 13C nmr). These compounds showed significant activity as inducers of the detoxifying enzyme glutathione S-transferase in the mouse liver and small intestine. The ability of natural anticarcinogens to induce detoxifying enzymes has been found to correlate with their activity in the inhibition of chemical carcinogenesis. Thus, these sesquiterpenes show promise as potential anticarcinogenic agents.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>1402962</pmid><doi>10.1021/np50085a029</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0163-3864 |
| ispartof | Journal of natural products (Washington, D.C.), 1992-07, Vol.55 (7), p.999-1003 |
| issn | 0163-3864 1520-6025 |
| language | eng |
| recordid | cdi_crossref_primary_10_1021_np50085a029 |
| source | MEDLINE; American Chemical Society Journals |
| subjects | ALPHA-HUMULENE ALPHA-HUMULENE EPOXIDE Animals Antineoplastic Agents - isolation & purification BETA-CARYOPHYLLENE BETA-CARYOPHYLLENE OXIDE Biological and medical sciences CARCINOGENESIS CARCINOGENOS CARCINOGENS COMPOSE PHENOLIQUE COMPUESTOS FENOLICOS Cytosol - enzymology DESINTOXICACION DETOXIFICATION ESTIMULO EUGENIA EUGENOL Female FOIE Gastric Mucosa - enzymology General pharmacology GLUTATHIONE TRANSFERASE Glutathione Transferase - metabolism HIGADO INTESTIN Intestinal Mucosa - enzymology INTESTINES INTESTINOS LIVER Liver - enzymology Medical sciences METABOLIC DETOXIFICATION METABOLISM METABOLISME METABOLISMO MICE Mice, Inbred A NEOPLASMAS NEOPLASME NEOPLASMS Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments PHENOLIC COMPOUNDS Plants, Medicinal RATON Sesquiterpenes - chemistry Sesquiterpenes - isolation & purification Sesquiterpenes - pharmacology SESQUITERPENOIDE SESQUITERPENOIDS SESQUITERPENOS SMALL INTESTINE SOURIS Spices STIMULATION STIMULI STIMULUS SUBSTANCE CANCERIGENE TRANSFERASAS TRANSFERASE TRANSFERASES |
| title | Sesquiterpenes from Clove (Eugenia caryophyllata) as Potential Anticarcinogenic Agents |
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