Labdane Diterpenoid Glycosides from Alpinia densespicata and Their Nitric Oxide Inhibitory Activities in Macrophages
Four new labdane diterpene glycosides (1−4) named alpindenosides A, B, C, and D, two new norditerpene glycosides (5, 6) named noralpindenosides A and B, and three known flavonoid glycosides (7−9) have been isolated from the stems of Alpinia densespicata. Structural elucidation of compounds 1−6 was b...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2009-06, Vol.72 (6), p.1097-1101 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | Kuo, Yu-Jen Hsiao, Ping-Chun Zhang, Li-Jie Wu, Ming-Der Liang, Yu-Han Ho, Hsiu-O Kuo, Yao-Haur |
| description | Four new labdane diterpene glycosides (1−4) named alpindenosides A, B, C, and D, two new norditerpene glycosides (5, 6) named noralpindenosides A and B, and three known flavonoid glycosides (7−9) have been isolated from the stems of Alpinia densespicata. Structural elucidation of compounds 1−6 was based on spectroscopic data. Compounds 1−9 all exhibited moderate NO inhibitory activities, whereas they were noncytotoxic at 20 μM against several human tumor cell lines. |
| doi_str_mv | 10.1021/np900019n |
| format | Article |
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Structural elucidation of compounds 1−6 was based on spectroscopic data. Compounds 1−9 all exhibited moderate NO inhibitory activities, whereas they were noncytotoxic at 20 μM against several human tumor cell lines.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np900019n</identifier><identifier>PMID: 19555124</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Northbrook, IL: American Chemical Society and American Society of Pharmacognosy</publisher><subject>alpindenosides ; Alpinia ; Alpinia - chemistry ; Alpinia densespicata ; Animals ; anti-inflammatory activity ; Biological and medical sciences ; chemical constituents of plants ; chemical structure ; cytotoxicity ; Diterpenes - chemistry ; Diterpenes - isolation & purification ; Diterpenes - pharmacology ; diterpenoids ; Drug Screening Assays, Antitumor ; Drugs, Chinese Herbal - chemistry ; Drugs, Chinese Herbal - isolation & purification ; Drugs, Chinese Herbal - pharmacology ; General pharmacology ; glycosides ; Glycosides - chemistry ; Glycosides - pharmacology ; HeLa Cells ; human cell lines ; Humans ; KB Cells ; labdane diterpenoids ; Lipopolysaccharides - pharmacology ; macrophages ; Macrophages - drug effects ; Medical sciences ; medicinal properties ; Mice ; Molecular Structure ; neoplasms ; nitric oxide ; Nitric Oxide - antagonists & inhibitors ; noralpindenosides ; Nuclear Magnetic Resonance, Biomolecular ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; phytochemicals ; spectroscopy ; stems</subject><ispartof>Journal of natural products (Washington, D.C.), 2009-06, Vol.72 (6), p.1097-1101</ispartof><rights>Copyright © 2009 American Chemical Society and American Society of Pharmacognosy</rights><rights>2009 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a431t-63b51bec71521409fde1bd965caedfd36c12be46c43879786a8526187c9ee76e3</citedby><cites>FETCH-LOGICAL-a431t-63b51bec71521409fde1bd965caedfd36c12be46c43879786a8526187c9ee76e3</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/np900019n$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np900019n$$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=21714583$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19555124$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kuo, Yu-Jen</creatorcontrib><creatorcontrib>Hsiao, Ping-Chun</creatorcontrib><creatorcontrib>Zhang, Li-Jie</creatorcontrib><creatorcontrib>Wu, Ming-Der</creatorcontrib><creatorcontrib>Liang, Yu-Han</creatorcontrib><creatorcontrib>Ho, Hsiu-O</creatorcontrib><creatorcontrib>Kuo, Yao-Haur</creatorcontrib><title>Labdane Diterpenoid Glycosides from Alpinia densespicata and Their Nitric Oxide Inhibitory Activities in Macrophages</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Four new labdane diterpene glycosides (1−4) named alpindenosides A, B, C, and D, two new norditerpene glycosides (5, 6) named noralpindenosides A and B, and three known flavonoid glycosides (7−9) have been isolated from the stems of Alpinia densespicata. Structural elucidation of compounds 1−6 was based on spectroscopic data. Compounds 1−9 all exhibited moderate NO inhibitory activities, whereas they were noncytotoxic at 20 μM against several human tumor cell lines.</description><subject>alpindenosides</subject><subject>Alpinia</subject><subject>Alpinia - chemistry</subject><subject>Alpinia densespicata</subject><subject>Animals</subject><subject>anti-inflammatory activity</subject><subject>Biological and medical sciences</subject><subject>chemical constituents of plants</subject><subject>chemical structure</subject><subject>cytotoxicity</subject><subject>Diterpenes - chemistry</subject><subject>Diterpenes - isolation & purification</subject><subject>Diterpenes - pharmacology</subject><subject>diterpenoids</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Drugs, Chinese Herbal - chemistry</subject><subject>Drugs, Chinese Herbal - isolation & purification</subject><subject>Drugs, Chinese Herbal - pharmacology</subject><subject>General pharmacology</subject><subject>glycosides</subject><subject>Glycosides - chemistry</subject><subject>Glycosides - pharmacology</subject><subject>HeLa Cells</subject><subject>human cell lines</subject><subject>Humans</subject><subject>KB Cells</subject><subject>labdane diterpenoids</subject><subject>Lipopolysaccharides - pharmacology</subject><subject>macrophages</subject><subject>Macrophages - drug effects</subject><subject>Medical sciences</subject><subject>medicinal properties</subject><subject>Mice</subject><subject>Molecular Structure</subject><subject>neoplasms</subject><subject>nitric oxide</subject><subject>Nitric Oxide - antagonists & inhibitors</subject><subject>noralpindenosides</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>phytochemicals</subject><subject>spectroscopy</subject><subject>stems</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0s1u1DAUBWALUdGhsOAFwBuoWAR8_Zd4OSpQKg10QbuOHPum4yrjBDuDmLfH1YzaTVVW3nw-8tExIW-AfQLG4XOcDGMMTHxGFqA4qzTj6jlZMNCiEo2Wx-RlzrfFCGbUC3IMRikFXC7IvLKdtxHplzBjmjCOwdPzYefGHDxm2qdxQ5fDFGKw1GPMmKfg7GypjZ5erTEk-jPMKTh6-bfcoBdxHbowj2lHl24Of8IcSkyI9Id1aZzW9gbzK3LU2yHj68N5Qq6_fb06-16tLs8vzparykoBc6VFp6BDV5dOIJnpPULnjVbOou-90A54h1I7KZra1I22jeIamtoZxFqjOCGn-9wpjb-3mOd2E7LDYSiFx21u6xoMCG3E_6WSSspGyiI_PCl1LcEwCQV-3MNSO-eEfTulsLFp1wJr72Zr72cr9u0hdNtt0D_Iw04FvD8Am50d-mSjC_necahBquaux7u96-3Y2ptUzPUvzkCUr6C54Pwhybrc3o7bFMsCjzzpH7yWtOs</recordid><startdate>20090601</startdate><enddate>20090601</enddate><creator>Kuo, Yu-Jen</creator><creator>Hsiao, Ping-Chun</creator><creator>Zhang, Li-Jie</creator><creator>Wu, Ming-Der</creator><creator>Liang, Yu-Han</creator><creator>Ho, Hsiu-O</creator><creator>Kuo, Yao-Haur</creator><general>American Chemical Society and American Society of Pharmacognosy</general><general>American Society of Pharmacognosy</general><scope>FBQ</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><scope>7X8</scope><scope>7T5</scope><scope>H94</scope></search><sort><creationdate>20090601</creationdate><title>Labdane Diterpenoid Glycosides from Alpinia densespicata and Their Nitric Oxide Inhibitory Activities in Macrophages</title><author>Kuo, Yu-Jen ; Hsiao, Ping-Chun ; Zhang, Li-Jie ; Wu, Ming-Der ; Liang, Yu-Han ; Ho, Hsiu-O ; Kuo, Yao-Haur</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a431t-63b51bec71521409fde1bd965caedfd36c12be46c43879786a8526187c9ee76e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>alpindenosides</topic><topic>Alpinia</topic><topic>Alpinia - chemistry</topic><topic>Alpinia densespicata</topic><topic>Animals</topic><topic>anti-inflammatory activity</topic><topic>Biological and medical sciences</topic><topic>chemical constituents of plants</topic><topic>chemical structure</topic><topic>cytotoxicity</topic><topic>Diterpenes - chemistry</topic><topic>Diterpenes - isolation & purification</topic><topic>Diterpenes - pharmacology</topic><topic>diterpenoids</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Drugs, Chinese Herbal - chemistry</topic><topic>Drugs, Chinese Herbal - isolation & purification</topic><topic>Drugs, Chinese Herbal - pharmacology</topic><topic>General pharmacology</topic><topic>glycosides</topic><topic>Glycosides - chemistry</topic><topic>Glycosides - pharmacology</topic><topic>HeLa Cells</topic><topic>human cell lines</topic><topic>Humans</topic><topic>KB Cells</topic><topic>labdane diterpenoids</topic><topic>Lipopolysaccharides - pharmacology</topic><topic>macrophages</topic><topic>Macrophages - drug effects</topic><topic>Medical sciences</topic><topic>medicinal properties</topic><topic>Mice</topic><topic>Molecular Structure</topic><topic>neoplasms</topic><topic>nitric oxide</topic><topic>Nitric Oxide - antagonists & inhibitors</topic><topic>noralpindenosides</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>phytochemicals</topic><topic>spectroscopy</topic><topic>stems</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kuo, Yu-Jen</creatorcontrib><creatorcontrib>Hsiao, Ping-Chun</creatorcontrib><creatorcontrib>Zhang, Li-Jie</creatorcontrib><creatorcontrib>Wu, Ming-Der</creatorcontrib><creatorcontrib>Liang, Yu-Han</creatorcontrib><creatorcontrib>Ho, Hsiu-O</creatorcontrib><creatorcontrib>Kuo, Yao-Haur</creatorcontrib><collection>AGRIS</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><collection>MEDLINE - Academic</collection><collection>Immunology Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kuo, Yu-Jen</au><au>Hsiao, Ping-Chun</au><au>Zhang, Li-Jie</au><au>Wu, Ming-Der</au><au>Liang, Yu-Han</au><au>Ho, Hsiu-O</au><au>Kuo, Yao-Haur</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Labdane Diterpenoid Glycosides from Alpinia densespicata and Their Nitric Oxide Inhibitory Activities in Macrophages</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2009-06-01</date><risdate>2009</risdate><volume>72</volume><issue>6</issue><spage>1097</spage><epage>1101</epage><pages>1097-1101</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>Four new labdane diterpene glycosides (1−4) named alpindenosides A, B, C, and D, two new norditerpene glycosides (5, 6) named noralpindenosides A and B, and three known flavonoid glycosides (7−9) have been isolated from the stems of Alpinia densespicata. Structural elucidation of compounds 1−6 was based on spectroscopic data. Compounds 1−9 all exhibited moderate NO inhibitory activities, whereas they were noncytotoxic at 20 μM against several human tumor cell lines.</abstract><cop>Northbrook, IL</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>19555124</pmid><doi>10.1021/np900019n</doi><tpages>5</tpages></addata></record> |
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| subjects | alpindenosides Alpinia Alpinia - chemistry Alpinia densespicata Animals anti-inflammatory activity Biological and medical sciences chemical constituents of plants chemical structure cytotoxicity Diterpenes - chemistry Diterpenes - isolation & purification Diterpenes - pharmacology diterpenoids Drug Screening Assays, Antitumor Drugs, Chinese Herbal - chemistry Drugs, Chinese Herbal - isolation & purification Drugs, Chinese Herbal - pharmacology General pharmacology glycosides Glycosides - chemistry Glycosides - pharmacology HeLa Cells human cell lines Humans KB Cells labdane diterpenoids Lipopolysaccharides - pharmacology macrophages Macrophages - drug effects Medical sciences medicinal properties Mice Molecular Structure neoplasms nitric oxide Nitric Oxide - antagonists & inhibitors noralpindenosides Nuclear Magnetic Resonance, Biomolecular Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments phytochemicals spectroscopy stems |
| title | Labdane Diterpenoid Glycosides from Alpinia densespicata and Their Nitric Oxide Inhibitory Activities in Macrophages |
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