Labdane diterpenoids and highly methoxylated bibenzyls from the liverwort Frullania inouei
Seven labdane diterpenoids and four highly methoxylated bibenzyls were isolated from the liverwort Frullania inouei. Cytoxicity test showed bibenzyls were active to inhibit human tumor cells proliferation and had a reversal effect to MDR. Four undescribed labdane diterpenoids, 1,2-dehydro-3,7-dioxo-...
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| Veröffentlicht in: | Phytochemistry (Oxford) 2010-09, Vol.71 (13), p.1573-1578 |
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| creator | Guo, Dong-Xiao Xiang, Feng Wang, Xiao-Ning Yuan, Hui-Qing Xi, Guang-Min Wang, Yan-Yan Yu, Wen-Tao Lou, Hong-Xiang |
| description | Seven labdane diterpenoids and four highly methoxylated bibenzyls were isolated from the liverwort
Frullania inouei. Cytoxicity test showed bibenzyls were active to inhibit human tumor cells proliferation and had a reversal effect to MDR.
Four undescribed labdane diterpenoids, 1,2-dehydro-3,7-dioxo-manoyl oxide (
1), 1,2-dehydro-7
β-hydroxy-3-oxo-manoyl oxide (
2), 3,7-dioxo-manoyl oxide (
3), and 3
β-hydroxy-7-oxo-manoyl oxide (
4) together with three known diterpenoids (
5–
7) and four highly methoxylated bibenzyls (
8–
11) were isolated from the liverwort
Frullania inouei. The absolute structures of
1–
4 were established by combined analysis of NMR data, CD data coupled with TDDFT CD calculations, and single-crystal X-ray diffraction measurement. Cytotoxicity tests to human tumor KB, KB/VCR, K562 or K562/A02 cells showed bibenzyls
8–
11 inhibited cell proliferation with ID
50 values ranging from 11.3 to 49.6
μM and overcame the multidrug resistance (MDR) with the reversal fold (RF) values ranging from 3.19 to 10.91 (5
μM) for vincristine-resistant KB/VCR and RF values from 4.40 to 8.26 (5
μM) for adriamycin-resistant K562/A02 cells, respectively. However, none of the diterpenoids were found to be active (ID
50
>
50
μM). |
| doi_str_mv | 10.1016/j.phytochem.2010.05.023 |
| format | Article |
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Frullania inouei. Cytoxicity test showed bibenzyls were active to inhibit human tumor cells proliferation and had a reversal effect to MDR.
Four undescribed labdane diterpenoids, 1,2-dehydro-3,7-dioxo-manoyl oxide (
1), 1,2-dehydro-7
β-hydroxy-3-oxo-manoyl oxide (
2), 3,7-dioxo-manoyl oxide (
3), and 3
β-hydroxy-7-oxo-manoyl oxide (
4) together with three known diterpenoids (
5–
7) and four highly methoxylated bibenzyls (
8–
11) were isolated from the liverwort
Frullania inouei. The absolute structures of
1–
4 were established by combined analysis of NMR data, CD data coupled with TDDFT CD calculations, and single-crystal X-ray diffraction measurement. Cytotoxicity tests to human tumor KB, KB/VCR, K562 or K562/A02 cells showed bibenzyls
8–
11 inhibited cell proliferation with ID
50 values ranging from 11.3 to 49.6
μM and overcame the multidrug resistance (MDR) with the reversal fold (RF) values ranging from 3.19 to 10.91 (5
μM) for vincristine-resistant KB/VCR and RF values from 4.40 to 8.26 (5
μM) for adriamycin-resistant K562/A02 cells, respectively. However, none of the diterpenoids were found to be active (ID
50
>
50
μM).</description><identifier>ISSN: 0031-9422</identifier><identifier>EISSN: 1873-3700</identifier><identifier>DOI: 10.1016/j.phytochem.2010.05.023</identifier><identifier>PMID: 20561654</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>anticarcinogenic activity ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - isolation & purification ; Antineoplastic Agents - pharmacology ; Bibenzyls - chemistry ; Bibenzyls - isolation & purification ; Bibenzyls - pharmacology ; Biological and medical sciences ; Cell Line, Tumor ; chemical constituents of plants ; Chemical constitution ; chemical structure ; Chemosystematics ; Circular Dichroism ; crystal structure ; Cytotoxicity ; Diterpenes - chemistry ; Diterpenes - isolation & purification ; Diterpenes - pharmacology ; Diterpenoids ; Drug Resistance, Multiple - drug effects ; Frullania - chemistry ; Frullania inouei ; Fundamental and applied biological sciences. Psychology ; Hepaticopsida ; human cell lines ; Humans ; hydrocarbons ; in vitro studies ; Inhibitory Concentration 50 ; labdane diterpenoids ; Liverworts ; Magnetic Resonance Spectroscopy ; Models, Molecular ; Molecular Conformation ; mosses and liverworts ; Multidrug resistance ; multiple drug resistance ; neoplasms ; Plant physiology and development ; TDDFT CD calculations ; X-Ray Diffraction</subject><ispartof>Phytochemistry (Oxford), 2010-09, Vol.71 (13), p.1573-1578</ispartof><rights>2010 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>(c) 2010 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c424t-eb429763a80e33dcf7afcfa85d87cad7cfa293b016e42fa91dd490012ae5d9343</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0031942210002177$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=23072164$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20561654$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Guo, Dong-Xiao</creatorcontrib><creatorcontrib>Xiang, Feng</creatorcontrib><creatorcontrib>Wang, Xiao-Ning</creatorcontrib><creatorcontrib>Yuan, Hui-Qing</creatorcontrib><creatorcontrib>Xi, Guang-Min</creatorcontrib><creatorcontrib>Wang, Yan-Yan</creatorcontrib><creatorcontrib>Yu, Wen-Tao</creatorcontrib><creatorcontrib>Lou, Hong-Xiang</creatorcontrib><title>Labdane diterpenoids and highly methoxylated bibenzyls from the liverwort Frullania inouei</title><title>Phytochemistry (Oxford)</title><addtitle>Phytochemistry</addtitle><description>Seven labdane diterpenoids and four highly methoxylated bibenzyls were isolated from the liverwort
Frullania inouei. Cytoxicity test showed bibenzyls were active to inhibit human tumor cells proliferation and had a reversal effect to MDR.
Four undescribed labdane diterpenoids, 1,2-dehydro-3,7-dioxo-manoyl oxide (
1), 1,2-dehydro-7
β-hydroxy-3-oxo-manoyl oxide (
2), 3,7-dioxo-manoyl oxide (
3), and 3
β-hydroxy-7-oxo-manoyl oxide (
4) together with three known diterpenoids (
5–
7) and four highly methoxylated bibenzyls (
8–
11) were isolated from the liverwort
Frullania inouei. The absolute structures of
1–
4 were established by combined analysis of NMR data, CD data coupled with TDDFT CD calculations, and single-crystal X-ray diffraction measurement. Cytotoxicity tests to human tumor KB, KB/VCR, K562 or K562/A02 cells showed bibenzyls
8–
11 inhibited cell proliferation with ID
50 values ranging from 11.3 to 49.6
μM and overcame the multidrug resistance (MDR) with the reversal fold (RF) values ranging from 3.19 to 10.91 (5
μM) for vincristine-resistant KB/VCR and RF values from 4.40 to 8.26 (5
μM) for adriamycin-resistant K562/A02 cells, respectively. However, none of the diterpenoids were found to be active (ID
50
>
50
μM).</description><subject>anticarcinogenic activity</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - isolation & purification</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Bibenzyls - chemistry</subject><subject>Bibenzyls - isolation & purification</subject><subject>Bibenzyls - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Cell Line, Tumor</subject><subject>chemical constituents of plants</subject><subject>Chemical constitution</subject><subject>chemical structure</subject><subject>Chemosystematics</subject><subject>Circular Dichroism</subject><subject>crystal structure</subject><subject>Cytotoxicity</subject><subject>Diterpenes - chemistry</subject><subject>Diterpenes - isolation & purification</subject><subject>Diterpenes - pharmacology</subject><subject>Diterpenoids</subject><subject>Drug Resistance, Multiple - drug effects</subject><subject>Frullania - chemistry</subject><subject>Frullania inouei</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Hepaticopsida</subject><subject>human cell lines</subject><subject>Humans</subject><subject>hydrocarbons</subject><subject>in vitro studies</subject><subject>Inhibitory Concentration 50</subject><subject>labdane diterpenoids</subject><subject>Liverworts</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Models, Molecular</subject><subject>Molecular Conformation</subject><subject>mosses and liverworts</subject><subject>Multidrug resistance</subject><subject>multiple drug resistance</subject><subject>neoplasms</subject><subject>Plant physiology and development</subject><subject>TDDFT CD calculations</subject><subject>X-Ray Diffraction</subject><issn>0031-9422</issn><issn>1873-3700</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1v1DAQhi0EosvCX6C-oJ6yjD8SJ8eqooC0EgfohYvl2JPGqyRe7GxL-uvxapdy5OSR9czMOw8hlww2DFj1cbfZ98scbI_jhkP-hXIDXLwgK1YrUQgF8JKsAAQrGsn5BXmT0g4AyrKqXpMLDmXFqlKuyM-taZ2ZkDo_Y9zjFLxL1EyO9v6-HxY64tyH38tgZnS09S1OT8uQaBfDSOce6eAfMD6GONPbeBgGM3lD_RQO6N-SV50ZEr47v2tyd_vpx82XYvvt89eb621hJZdzga3kjaqEqQGFcLZTprOdqUtXK2ucyjVvRJuvRsk70zDnZAPAuMHSNUKKNbk6zd3H8OuAadajTxaPWTAcklYZZ3WdZayJOpE2hpQidnof_Wjiohnoo1e9089e9dGrhlJnr7nz_XnHoR3RPff9FZmBD2fAJGuGLprJ-vSPE6A4q47c5YnrTNDmPmbm7nveJHJEJWXNM3F9IjA7e_AYdbIeJ4vOR7SzdsH_N-4fDfil-Q</recordid><startdate>20100901</startdate><enddate>20100901</enddate><creator>Guo, Dong-Xiao</creator><creator>Xiang, Feng</creator><creator>Wang, Xiao-Ning</creator><creator>Yuan, Hui-Qing</creator><creator>Xi, Guang-Min</creator><creator>Wang, Yan-Yan</creator><creator>Yu, Wen-Tao</creator><creator>Lou, Hong-Xiang</creator><general>Elsevier Ltd</general><general>Elsevier</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></search><sort><creationdate>20100901</creationdate><title>Labdane diterpenoids and highly methoxylated bibenzyls from the liverwort Frullania inouei</title><author>Guo, Dong-Xiao ; Xiang, Feng ; Wang, Xiao-Ning ; Yuan, Hui-Qing ; Xi, Guang-Min ; Wang, Yan-Yan ; Yu, Wen-Tao ; Lou, Hong-Xiang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c424t-eb429763a80e33dcf7afcfa85d87cad7cfa293b016e42fa91dd490012ae5d9343</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>anticarcinogenic activity</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - isolation & purification</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Bibenzyls - chemistry</topic><topic>Bibenzyls - isolation & purification</topic><topic>Bibenzyls - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Cell Line, Tumor</topic><topic>chemical constituents of plants</topic><topic>Chemical constitution</topic><topic>chemical structure</topic><topic>Chemosystematics</topic><topic>Circular Dichroism</topic><topic>crystal structure</topic><topic>Cytotoxicity</topic><topic>Diterpenes - chemistry</topic><topic>Diterpenes - isolation & purification</topic><topic>Diterpenes - pharmacology</topic><topic>Diterpenoids</topic><topic>Drug Resistance, Multiple - drug effects</topic><topic>Frullania - chemistry</topic><topic>Frullania inouei</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Hepaticopsida</topic><topic>human cell lines</topic><topic>Humans</topic><topic>hydrocarbons</topic><topic>in vitro studies</topic><topic>Inhibitory Concentration 50</topic><topic>labdane diterpenoids</topic><topic>Liverworts</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Models, Molecular</topic><topic>Molecular Conformation</topic><topic>mosses and liverworts</topic><topic>Multidrug resistance</topic><topic>multiple drug resistance</topic><topic>neoplasms</topic><topic>Plant physiology and development</topic><topic>TDDFT CD calculations</topic><topic>X-Ray Diffraction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Guo, Dong-Xiao</creatorcontrib><creatorcontrib>Xiang, Feng</creatorcontrib><creatorcontrib>Wang, Xiao-Ning</creatorcontrib><creatorcontrib>Yuan, Hui-Qing</creatorcontrib><creatorcontrib>Xi, Guang-Min</creatorcontrib><creatorcontrib>Wang, Yan-Yan</creatorcontrib><creatorcontrib>Yu, Wen-Tao</creatorcontrib><creatorcontrib>Lou, Hong-Xiang</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><jtitle>Phytochemistry (Oxford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Guo, Dong-Xiao</au><au>Xiang, Feng</au><au>Wang, Xiao-Ning</au><au>Yuan, Hui-Qing</au><au>Xi, Guang-Min</au><au>Wang, Yan-Yan</au><au>Yu, Wen-Tao</au><au>Lou, Hong-Xiang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Labdane diterpenoids and highly methoxylated bibenzyls from the liverwort Frullania inouei</atitle><jtitle>Phytochemistry (Oxford)</jtitle><addtitle>Phytochemistry</addtitle><date>2010-09-01</date><risdate>2010</risdate><volume>71</volume><issue>13</issue><spage>1573</spage><epage>1578</epage><pages>1573-1578</pages><issn>0031-9422</issn><eissn>1873-3700</eissn><abstract>Seven labdane diterpenoids and four highly methoxylated bibenzyls were isolated from the liverwort
Frullania inouei. Cytoxicity test showed bibenzyls were active to inhibit human tumor cells proliferation and had a reversal effect to MDR.
Four undescribed labdane diterpenoids, 1,2-dehydro-3,7-dioxo-manoyl oxide (
1), 1,2-dehydro-7
β-hydroxy-3-oxo-manoyl oxide (
2), 3,7-dioxo-manoyl oxide (
3), and 3
β-hydroxy-7-oxo-manoyl oxide (
4) together with three known diterpenoids (
5–
7) and four highly methoxylated bibenzyls (
8–
11) were isolated from the liverwort
Frullania inouei. The absolute structures of
1–
4 were established by combined analysis of NMR data, CD data coupled with TDDFT CD calculations, and single-crystal X-ray diffraction measurement. Cytotoxicity tests to human tumor KB, KB/VCR, K562 or K562/A02 cells showed bibenzyls
8–
11 inhibited cell proliferation with ID
50 values ranging from 11.3 to 49.6
μM and overcame the multidrug resistance (MDR) with the reversal fold (RF) values ranging from 3.19 to 10.91 (5
μM) for vincristine-resistant KB/VCR and RF values from 4.40 to 8.26 (5
μM) for adriamycin-resistant K562/A02 cells, respectively. However, none of the diterpenoids were found to be active (ID
50
>
50
μM).</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>20561654</pmid><doi>10.1016/j.phytochem.2010.05.023</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
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| ispartof | Phytochemistry (Oxford), 2010-09, Vol.71 (13), p.1573-1578 |
| issn | 0031-9422 1873-3700 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | anticarcinogenic activity Antineoplastic Agents - chemistry Antineoplastic Agents - isolation & purification Antineoplastic Agents - pharmacology Bibenzyls - chemistry Bibenzyls - isolation & purification Bibenzyls - pharmacology Biological and medical sciences Cell Line, Tumor chemical constituents of plants Chemical constitution chemical structure Chemosystematics Circular Dichroism crystal structure Cytotoxicity Diterpenes - chemistry Diterpenes - isolation & purification Diterpenes - pharmacology Diterpenoids Drug Resistance, Multiple - drug effects Frullania - chemistry Frullania inouei Fundamental and applied biological sciences. Psychology Hepaticopsida human cell lines Humans hydrocarbons in vitro studies Inhibitory Concentration 50 labdane diterpenoids Liverworts Magnetic Resonance Spectroscopy Models, Molecular Molecular Conformation mosses and liverworts Multidrug resistance multiple drug resistance neoplasms Plant physiology and development TDDFT CD calculations X-Ray Diffraction |
| title | Labdane diterpenoids and highly methoxylated bibenzyls from the liverwort Frullania inouei |
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