Constituents of the Vietnamese Medicinal Plant Orthosiphon stamineus
From the MeOH extract of the aerial part of Vietnamese Orthosiphon stamineus, five new isopimarane-type diterpenes [orthosiphols F-J (1-5)] and two new diterpenes [staminols A (6) and B (7)] with a novel carbon-framework, to which we proposed the name "staminane", and three new highly-oxyg...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 2000/11/01, Vol.48(11), pp.1711-1719 |
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| container_title | Chemical & pharmaceutical bulletin |
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| creator | TEZUKA, Yasuhiro STAMPOULIS, Pavlos BANSKOTA, Arjun H. AWALE, Suresh TRAN, Kim Qui SAIKI, Ikuo KADOTA, Shigetoshi |
| description | From the MeOH extract of the aerial part of Vietnamese Orthosiphon stamineus, five new isopimarane-type diterpenes [orthosiphols F-J (1-5)] and two new diterpenes [staminols A (6) and B (7)] with a novel carbon-framework, to which we proposed the name "staminane", and three new highly-oxygenated staminane-type diterpenes [staminolactones A (8) and B (9) and norstaminol A (10)] were isolated. Moreover, staminolactone A (8) is 8, 14-secostaminane-type and staminolactone B (9) is 13, 14-secostaminane-type, while norstaminol A (10) is 14-norstaminen-type. Together with these new diterpenes, sixteen known compounds were also isolated and identified to be : 7, 3', 4'-tri-O-methylluteolin (11), eupatorin (12), sinensetin (13), 5-hydroxy-6, 7, 3'4'-tetramethoxyflavone (14), salvigenin (15), ladanein (16), tetramethylscutellarein (17), 6-hydroxy-5, 7, 4'-trimethoxyflavone (18), vomifoliol (19), aurantiamide acetate (20), rosmarinic acid (21), caffeic acid (22), oleanolic acid (23), ursolic acid (24), betulinic acid (25), and β-sitosterol (26). All the isolated compounds were tested for their cytotoxicity towards highly liver metastatic murine colon 26-L5 carcinoma cells, and the new diterpenes, except for 4, and flavonoids (11, 12, 16, 18) showed cytotoxicity with an ED^ value between 10 and 90 μg/ml. |
| doi_str_mv | 10.1248/cpb.48.1711 |
| format | Article |
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Moreover, staminolactone A (8) is 8, 14-secostaminane-type and staminolactone B (9) is 13, 14-secostaminane-type, while norstaminol A (10) is 14-norstaminen-type. Together with these new diterpenes, sixteen known compounds were also isolated and identified to be : 7, 3', 4'-tri-O-methylluteolin (11), eupatorin (12), sinensetin (13), 5-hydroxy-6, 7, 3'4'-tetramethoxyflavone (14), salvigenin (15), ladanein (16), tetramethylscutellarein (17), 6-hydroxy-5, 7, 4'-trimethoxyflavone (18), vomifoliol (19), aurantiamide acetate (20), rosmarinic acid (21), caffeic acid (22), oleanolic acid (23), ursolic acid (24), betulinic acid (25), and β-sitosterol (26). All the isolated compounds were tested for their cytotoxicity towards highly liver metastatic murine colon 26-L5 carcinoma cells, and the new diterpenes, except for 4, and flavonoids (11, 12, 16, 18) showed cytotoxicity with an ED^ value between 10 and 90 μg/ml.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.48.1711</identifier><identifier>PMID: 11086900</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>Animals ; Antineoplastic Agents, Phytogenic - isolation & purification ; Antineoplastic Agents, Phytogenic - pharmacology ; Biological and medical sciences ; colon 26-L5 carcinoma ; cytotoxicity ; Diterpenes - chemistry ; Diterpenes - isolation & purification ; Diterpenes - pharmacology ; Drug Screening Assays, Antitumor ; General pharmacology ; isopimarane-type diterpene ; Magnetic Resonance Spectroscopy ; Medical sciences ; Mice ; Molecular Structure ; Orthosiphon stamineus ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Plant Extracts - analysis ; Plants, Medicinal - chemistry ; staminane-type diterpene ; Tumor Cells, Cultured ; Vietnam ; Vietnamese medicinal plant</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2000/11/01, Vol.48(11), pp.1711-1719</ispartof><rights>The Pharmaceutical Society of Japan</rights><rights>2001 INIST-CNRS</rights><rights>Copyright Japan Science and Technology Agency 2000</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c633t-60fa371b0e681847a149100b7c1a906b43fefdfebcffd8db935bda5f2d94edcb3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,1877,27905,27906</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=827164$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11086900$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>TEZUKA, Yasuhiro</creatorcontrib><creatorcontrib>STAMPOULIS, Pavlos</creatorcontrib><creatorcontrib>BANSKOTA, Arjun H.</creatorcontrib><creatorcontrib>AWALE, Suresh</creatorcontrib><creatorcontrib>TRAN, Kim Qui</creatorcontrib><creatorcontrib>SAIKI, Ikuo</creatorcontrib><creatorcontrib>KADOTA, Shigetoshi</creatorcontrib><title>Constituents of the Vietnamese Medicinal Plant Orthosiphon stamineus</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>From the MeOH extract of the aerial part of Vietnamese Orthosiphon stamineus, five new isopimarane-type diterpenes [orthosiphols F-J (1-5)] and two new diterpenes [staminols A (6) and B (7)] with a novel carbon-framework, to which we proposed the name "staminane", and three new highly-oxygenated staminane-type diterpenes [staminolactones A (8) and B (9) and norstaminol A (10)] were isolated. Moreover, staminolactone A (8) is 8, 14-secostaminane-type and staminolactone B (9) is 13, 14-secostaminane-type, while norstaminol A (10) is 14-norstaminen-type. Together with these new diterpenes, sixteen known compounds were also isolated and identified to be : 7, 3', 4'-tri-O-methylluteolin (11), eupatorin (12), sinensetin (13), 5-hydroxy-6, 7, 3'4'-tetramethoxyflavone (14), salvigenin (15), ladanein (16), tetramethylscutellarein (17), 6-hydroxy-5, 7, 4'-trimethoxyflavone (18), vomifoliol (19), aurantiamide acetate (20), rosmarinic acid (21), caffeic acid (22), oleanolic acid (23), ursolic acid (24), betulinic acid (25), and β-sitosterol (26). All the isolated compounds were tested for their cytotoxicity towards highly liver metastatic murine colon 26-L5 carcinoma cells, and the new diterpenes, except for 4, and flavonoids (11, 12, 16, 18) showed cytotoxicity with an ED^ value between 10 and 90 μg/ml.</description><subject>Animals</subject><subject>Antineoplastic Agents, Phytogenic - isolation & purification</subject><subject>Antineoplastic Agents, Phytogenic - pharmacology</subject><subject>Biological and medical sciences</subject><subject>colon 26-L5 carcinoma</subject><subject>cytotoxicity</subject><subject>Diterpenes - chemistry</subject><subject>Diterpenes - isolation & purification</subject><subject>Diterpenes - pharmacology</subject><subject>Drug Screening Assays, Antitumor</subject><subject>General pharmacology</subject><subject>isopimarane-type diterpene</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Molecular Structure</subject><subject>Orthosiphon stamineus</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Plant Extracts - analysis</subject><subject>Plants, Medicinal - chemistry</subject><subject>staminane-type diterpene</subject><subject>Tumor Cells, Cultured</subject><subject>Vietnam</subject><subject>Vietnamese medicinal plant</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkE1v1DAQQC0EotvCiTuKhMQFZZmxna8j2tKCVFQOwNWynTHrVeIstnPg35OwqxZx8Rz8NM9-jL1C2CKX7Xt7NFvZbrFBfMI2KGRTVpyLp2wDAF3JRS0u2GVKBwBeQSOeswtEaOsOYMOud1NI2eeZQk7F5Iq8p-KHpxz0SImKL9R764Meiq-DDrm4j3k_JX_cT6FIWY8-0JxesGdOD4lenucV-37z8dvuU3l3f_t59-GutLUQuazBadGgAapbbGWjUXYIYBqLuoPaSOHI9Y6Mda5ve9OJyvS6crzvJPXWiCv29rT3GKdfM6WsRp8sDcvLaJqTarhcgoBcwDf_gYdpjssvkkJZgxBcNCv17kTZOKUUyalj9KOOvxWCWtOqJa1axpp2oV-fd85mpP6RPbf8R6qT1YOLOlifHriWN1iv0psTdVjy_aSHax2ztwOtSuyq9q8Wz-fqfwT2OioK4g8DZ5mB</recordid><startdate>20001101</startdate><enddate>20001101</enddate><creator>TEZUKA, Yasuhiro</creator><creator>STAMPOULIS, Pavlos</creator><creator>BANSKOTA, Arjun H.</creator><creator>AWALE, Suresh</creator><creator>TRAN, Kim Qui</creator><creator>SAIKI, Ikuo</creator><creator>KADOTA, Shigetoshi</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</general><general>Japan Science and Technology Agency</general><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><scope>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope><scope>7X8</scope></search><sort><creationdate>20001101</creationdate><title>Constituents of the Vietnamese Medicinal Plant Orthosiphon stamineus</title><author>TEZUKA, Yasuhiro ; STAMPOULIS, Pavlos ; BANSKOTA, Arjun H. ; AWALE, Suresh ; TRAN, Kim Qui ; SAIKI, Ikuo ; KADOTA, Shigetoshi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c633t-60fa371b0e681847a149100b7c1a906b43fefdfebcffd8db935bda5f2d94edcb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>Animals</topic><topic>Antineoplastic Agents, Phytogenic - isolation & purification</topic><topic>Antineoplastic Agents, Phytogenic - pharmacology</topic><topic>Biological and medical sciences</topic><topic>colon 26-L5 carcinoma</topic><topic>cytotoxicity</topic><topic>Diterpenes - chemistry</topic><topic>Diterpenes - isolation & purification</topic><topic>Diterpenes - pharmacology</topic><topic>Drug Screening Assays, Antitumor</topic><topic>General pharmacology</topic><topic>isopimarane-type diterpene</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Molecular Structure</topic><topic>Orthosiphon stamineus</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Plant Extracts - analysis</topic><topic>Plants, Medicinal - chemistry</topic><topic>staminane-type diterpene</topic><topic>Tumor Cells, Cultured</topic><topic>Vietnam</topic><topic>Vietnamese medicinal plant</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>TEZUKA, Yasuhiro</creatorcontrib><creatorcontrib>STAMPOULIS, Pavlos</creatorcontrib><creatorcontrib>BANSKOTA, Arjun H.</creatorcontrib><creatorcontrib>AWALE, Suresh</creatorcontrib><creatorcontrib>TRAN, Kim Qui</creatorcontrib><creatorcontrib>SAIKI, Ikuo</creatorcontrib><creatorcontrib>KADOTA, Shigetoshi</creatorcontrib><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><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>TEZUKA, Yasuhiro</au><au>STAMPOULIS, Pavlos</au><au>BANSKOTA, Arjun H.</au><au>AWALE, Suresh</au><au>TRAN, Kim Qui</au><au>SAIKI, Ikuo</au><au>KADOTA, Shigetoshi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Constituents of the Vietnamese Medicinal Plant Orthosiphon stamineus</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2000-11-01</date><risdate>2000</risdate><volume>48</volume><issue>11</issue><spage>1711</spage><epage>1719</epage><pages>1711-1719</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>From the MeOH extract of the aerial part of Vietnamese Orthosiphon stamineus, five new isopimarane-type diterpenes [orthosiphols F-J (1-5)] and two new diterpenes [staminols A (6) and B (7)] with a novel carbon-framework, to which we proposed the name "staminane", and three new highly-oxygenated staminane-type diterpenes [staminolactones A (8) and B (9) and norstaminol A (10)] were isolated. Moreover, staminolactone A (8) is 8, 14-secostaminane-type and staminolactone B (9) is 13, 14-secostaminane-type, while norstaminol A (10) is 14-norstaminen-type. Together with these new diterpenes, sixteen known compounds were also isolated and identified to be : 7, 3', 4'-tri-O-methylluteolin (11), eupatorin (12), sinensetin (13), 5-hydroxy-6, 7, 3'4'-tetramethoxyflavone (14), salvigenin (15), ladanein (16), tetramethylscutellarein (17), 6-hydroxy-5, 7, 4'-trimethoxyflavone (18), vomifoliol (19), aurantiamide acetate (20), rosmarinic acid (21), caffeic acid (22), oleanolic acid (23), ursolic acid (24), betulinic acid (25), and β-sitosterol (26). All the isolated compounds were tested for their cytotoxicity towards highly liver metastatic murine colon 26-L5 carcinoma cells, and the new diterpenes, except for 4, and flavonoids (11, 12, 16, 18) showed cytotoxicity with an ED^ value between 10 and 90 μg/ml.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>11086900</pmid><doi>10.1248/cpb.48.1711</doi><tpages>9</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Animals Antineoplastic Agents, Phytogenic - isolation & purification Antineoplastic Agents, Phytogenic - pharmacology Biological and medical sciences colon 26-L5 carcinoma cytotoxicity Diterpenes - chemistry Diterpenes - isolation & purification Diterpenes - pharmacology Drug Screening Assays, Antitumor General pharmacology isopimarane-type diterpene Magnetic Resonance Spectroscopy Medical sciences Mice Molecular Structure Orthosiphon stamineus Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Plant Extracts - analysis Plants, Medicinal - chemistry staminane-type diterpene Tumor Cells, Cultured Vietnam Vietnamese medicinal plant |
| title | Constituents of the Vietnamese Medicinal Plant Orthosiphon stamineus |
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