Anti-inflammatory Triterpenoid Saponins from the Stem Bark of Kalopanax pictus
Five new compounds, 16,23,29-trihydroxy-3-oxo-olean-12-en-28-oic acid (1), 4,23,29-trihydroxy-3,4-seco-olean-12-en-3-oate-28-oic acid (2), 3β,6β,23-trihydroxyolean-12-en-28-oic acid 28-O-β-d-glucopyranoside (3), 3-O-[2,3-di-O-acetyl-α-l-arabinopyranosyl]hederagenin 28-O-α-l-rhamnopyranosyl-(1→4)-β-d...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2011-09, Vol.74 (9), p.1908-1915 |
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| container_issue | 9 |
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| container_title | Journal of natural products (Washington, D.C.) |
| container_volume | 74 |
| creator | Quang, Tran H Ngan, Nguyen T. T Minh, Chau V Kiem, Phan V Nhiem, Nguyen X Tai, Bui H Thao, Nguyen P Tung, Nguyen H Song, Seok B Kim, Young H |
| description | Five new compounds, 16,23,29-trihydroxy-3-oxo-olean-12-en-28-oic acid (1), 4,23,29-trihydroxy-3,4-seco-olean-12-en-3-oate-28-oic acid (2), 3β,6β,23-trihydroxyolean-12-en-28-oic acid 28-O-β-d-glucopyranoside (3), 3-O-[2,3-di-O-acetyl-α-l-arabinopyranosyl]hederagenin 28-O-α-l-rhamnopyranosyl-(1→4)-β-d-glucopyranosyl-(1→6)-β-d-glucopyranoside (4), and 3-O-[3,4-di-O-acetyl-α-l-arabinopyranosyl]hederagenin 28-O-α-l-rhamnopyranosyl-(1→4)-β-d-glucopyranosyl-(1→6)-β-d-glucopyranoside (5), as well as 10 known compounds (6–15), were isolated from the stem bark of Kalopanax pictus. Compounds 1–5 and 7–14 inhibited TNFα-induced NF-κB transcriptional activity in HepG2 cells in a dose-dependent manner, with IC50 values ranging from 0.6 to 16.4 μM. Furthermore, the transcriptional inhibitory function of these compounds was confirmed on the basis of decreases in COX-2 and iNOS gene expression in HepG2 cells. The structure–activity relationship of the compounds with respect to anti-inflammatory activity is also discussed. |
| doi_str_mv | 10.1021/np200382s |
| format | Article |
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T ; Minh, Chau V ; Kiem, Phan V ; Nhiem, Nguyen X ; Tai, Bui H ; Thao, Nguyen P ; Tung, Nguyen H ; Song, Seok B ; Kim, Young H</creator><creatorcontrib>Quang, Tran H ; Ngan, Nguyen T. T ; Minh, Chau V ; Kiem, Phan V ; Nhiem, Nguyen X ; Tai, Bui H ; Thao, Nguyen P ; Tung, Nguyen H ; Song, Seok B ; Kim, Young H</creatorcontrib><description>Five new compounds, 16,23,29-trihydroxy-3-oxo-olean-12-en-28-oic acid (1), 4,23,29-trihydroxy-3,4-seco-olean-12-en-3-oate-28-oic acid (2), 3β,6β,23-trihydroxyolean-12-en-28-oic acid 28-O-β-d-glucopyranoside (3), 3-O-[2,3-di-O-acetyl-α-l-arabinopyranosyl]hederagenin 28-O-α-l-rhamnopyranosyl-(1→4)-β-d-glucopyranosyl-(1→6)-β-d-glucopyranoside (4), and 3-O-[3,4-di-O-acetyl-α-l-arabinopyranosyl]hederagenin 28-O-α-l-rhamnopyranosyl-(1→4)-β-d-glucopyranosyl-(1→6)-β-d-glucopyranoside (5), as well as 10 known compounds (6–15), were isolated from the stem bark of Kalopanax pictus. Compounds 1–5 and 7–14 inhibited TNFα-induced NF-κB transcriptional activity in HepG2 cells in a dose-dependent manner, with IC50 values ranging from 0.6 to 16.4 μM. Furthermore, the transcriptional inhibitory function of these compounds was confirmed on the basis of decreases in COX-2 and iNOS gene expression in HepG2 cells. The structure–activity relationship of the compounds with respect to anti-inflammatory activity is also discussed.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np200382s</identifier><identifier>PMID: 21870831</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Northbrook, IL: American Chemical Society and American Society of Pharmacognosy</publisher><subject>Anti-Inflammatory Agents - chemistry ; Anti-Inflammatory Agents - isolation & purification ; Anti-Inflammatory Agents - pharmacology ; Base Sequence ; Biological and medical sciences ; Cyclooxygenase 2 Inhibitors - chemistry ; Cyclooxygenase 2 Inhibitors - isolation & purification ; Cyclooxygenase 2 Inhibitors - pharmacology ; General pharmacology ; Hep G2 Cells ; Humans ; Kalopanax - chemistry ; Korea ; Medical sciences ; Molecular Structure ; NF-kappa B - drug effects ; Nitric Oxide Synthase Type II - antagonists & inhibitors ; Pharmacognosy. 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T</creatorcontrib><creatorcontrib>Minh, Chau V</creatorcontrib><creatorcontrib>Kiem, Phan V</creatorcontrib><creatorcontrib>Nhiem, Nguyen X</creatorcontrib><creatorcontrib>Tai, Bui H</creatorcontrib><creatorcontrib>Thao, Nguyen P</creatorcontrib><creatorcontrib>Tung, Nguyen H</creatorcontrib><creatorcontrib>Song, Seok B</creatorcontrib><creatorcontrib>Kim, Young H</creatorcontrib><title>Anti-inflammatory Triterpenoid Saponins from the Stem Bark of Kalopanax pictus</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Five new compounds, 16,23,29-trihydroxy-3-oxo-olean-12-en-28-oic acid (1), 4,23,29-trihydroxy-3,4-seco-olean-12-en-3-oate-28-oic acid (2), 3β,6β,23-trihydroxyolean-12-en-28-oic acid 28-O-β-d-glucopyranoside (3), 3-O-[2,3-di-O-acetyl-α-l-arabinopyranosyl]hederagenin 28-O-α-l-rhamnopyranosyl-(1→4)-β-d-glucopyranosyl-(1→6)-β-d-glucopyranoside (4), and 3-O-[3,4-di-O-acetyl-α-l-arabinopyranosyl]hederagenin 28-O-α-l-rhamnopyranosyl-(1→4)-β-d-glucopyranosyl-(1→6)-β-d-glucopyranoside (5), as well as 10 known compounds (6–15), were isolated from the stem bark of Kalopanax pictus. Compounds 1–5 and 7–14 inhibited TNFα-induced NF-κB transcriptional activity in HepG2 cells in a dose-dependent manner, with IC50 values ranging from 0.6 to 16.4 μM. Furthermore, the transcriptional inhibitory function of these compounds was confirmed on the basis of decreases in COX-2 and iNOS gene expression in HepG2 cells. The structure–activity relationship of the compounds with respect to anti-inflammatory activity is also discussed.</description><subject>Anti-Inflammatory Agents - chemistry</subject><subject>Anti-Inflammatory Agents - isolation & purification</subject><subject>Anti-Inflammatory Agents - pharmacology</subject><subject>Base Sequence</subject><subject>Biological and medical sciences</subject><subject>Cyclooxygenase 2 Inhibitors - chemistry</subject><subject>Cyclooxygenase 2 Inhibitors - isolation & purification</subject><subject>Cyclooxygenase 2 Inhibitors - pharmacology</subject><subject>General pharmacology</subject><subject>Hep G2 Cells</subject><subject>Humans</subject><subject>Kalopanax - chemistry</subject><subject>Korea</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>NF-kappa B - drug effects</subject><subject>Nitric Oxide Synthase Type II - antagonists & inhibitors</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Plant Bark - chemistry</subject><subject>Saponins - chemistry</subject><subject>Saponins - isolation & purification</subject><subject>Saponins - pharmacology</subject><subject>Structure-Activity Relationship</subject><subject>Triterpenes - chemistry</subject><subject>Triterpenes - isolation & purification</subject><subject>Triterpenes - pharmacology</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0MtKxTAQgOEgih4vC19AshFxUc2tabpU8YaiC3VdJjkJRtukJi143t6KR90IMovZfMzAj9AuJUeUMHocekYIVyyvoBktGSkkYeUqmhEqecGVFBtoM-cXMiFSl-tog1FVEcXpDN2dhMEXPrgWug6GmBb4MfnBpt6G6Of4AfoYfMjYpdjh4dnih8F2-BTSK44O30AbewjwjntvhjFvozUHbbY7y72Fni7OH8-uitv7y-uzk9sCeCWHQlaMyooax7We10xoTZ0URlagQDlX1goqgFKA1pwRqQUn3JVGcKOspNrwLXTwdbdP8W20eWg6n41tWwg2jrmpaS2opEz9K1UtCK05Kyd5-CVNijkn65o--Q7SoqGk-ezc_HSe7N7y6qg7O_-R32EnsL8EkA20LkEwPv86UU5T818HJjcvcUxhyvbHww9lnJC6</recordid><startdate>20110923</startdate><enddate>20110923</enddate><creator>Quang, Tran H</creator><creator>Ngan, Nguyen T. 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Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Plant Bark - chemistry</topic><topic>Saponins - chemistry</topic><topic>Saponins - isolation & purification</topic><topic>Saponins - pharmacology</topic><topic>Structure-Activity Relationship</topic><topic>Triterpenes - chemistry</topic><topic>Triterpenes - isolation & purification</topic><topic>Triterpenes - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Quang, Tran H</creatorcontrib><creatorcontrib>Ngan, Nguyen T. 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Prod</addtitle><date>2011-09-23</date><risdate>2011</risdate><volume>74</volume><issue>9</issue><spage>1908</spage><epage>1915</epage><pages>1908-1915</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>Five new compounds, 16,23,29-trihydroxy-3-oxo-olean-12-en-28-oic acid (1), 4,23,29-trihydroxy-3,4-seco-olean-12-en-3-oate-28-oic acid (2), 3β,6β,23-trihydroxyolean-12-en-28-oic acid 28-O-β-d-glucopyranoside (3), 3-O-[2,3-di-O-acetyl-α-l-arabinopyranosyl]hederagenin 28-O-α-l-rhamnopyranosyl-(1→4)-β-d-glucopyranosyl-(1→6)-β-d-glucopyranoside (4), and 3-O-[3,4-di-O-acetyl-α-l-arabinopyranosyl]hederagenin 28-O-α-l-rhamnopyranosyl-(1→4)-β-d-glucopyranosyl-(1→6)-β-d-glucopyranoside (5), as well as 10 known compounds (6–15), were isolated from the stem bark of Kalopanax pictus. Compounds 1–5 and 7–14 inhibited TNFα-induced NF-κB transcriptional activity in HepG2 cells in a dose-dependent manner, with IC50 values ranging from 0.6 to 16.4 μM. Furthermore, the transcriptional inhibitory function of these compounds was confirmed on the basis of decreases in COX-2 and iNOS gene expression in HepG2 cells. The structure–activity relationship of the compounds with respect to anti-inflammatory activity is also discussed.</abstract><cop>Northbrook, IL</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>21870831</pmid><doi>10.1021/np200382s</doi><tpages>8</tpages></addata></record> |
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| subjects | Anti-Inflammatory Agents - chemistry Anti-Inflammatory Agents - isolation & purification Anti-Inflammatory Agents - pharmacology Base Sequence Biological and medical sciences Cyclooxygenase 2 Inhibitors - chemistry Cyclooxygenase 2 Inhibitors - isolation & purification Cyclooxygenase 2 Inhibitors - pharmacology General pharmacology Hep G2 Cells Humans Kalopanax - chemistry Korea Medical sciences Molecular Structure NF-kappa B - drug effects Nitric Oxide Synthase Type II - antagonists & inhibitors Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Plant Bark - chemistry Saponins - chemistry Saponins - isolation & purification Saponins - pharmacology Structure-Activity Relationship Triterpenes - chemistry Triterpenes - isolation & purification Triterpenes - pharmacology |
| title | Anti-inflammatory Triterpenoid Saponins from the Stem Bark of Kalopanax pictus |
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