Rubipodanin B, a New Cytotoxic Cyclopeptide from Rubia podantha
Using the TLC cyclopeptide protosite detection method, a new cyclohexapeptide named rubipodanin B (1), together with 11 known Rubiaceae‐type cyclopeptides (RAs), RA‐X‐OMe (2), RA‐IV (3), RA‐XI (4), RA‐XIII‐OMe (5), rubiyunnanin C (6), RA‐I (7), RA‐III (8), RA‐V (9), RA‐VII (10), RA‐XII (11) and rubi...
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Veröffentlicht in: | Chemistry & biodiversity 2019-01, Vol.16 (1), p.e1800438-n/a |
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description | Using the TLC cyclopeptide protosite detection method, a new cyclohexapeptide named rubipodanin B (1), together with 11 known Rubiaceae‐type cyclopeptides (RAs), RA‐X‐OMe (2), RA‐IV (3), RA‐XI (4), RA‐XIII‐OMe (5), rubiyunnanin C (6), RA‐I (7), RA‐III (8), RA‐V (9), RA‐VII (10), RA‐XII (11) and rubipodanin A (12), were obtained from the roots and rhizomes of Rubia podantha Diels. The structures were determined using various spectroscopic methods. Among them, 2 was firstly identified as a natural product, and 3–6 were firstly isolated from this species. Cytotoxicity and NF‐κB signaling pathway activity of 1, 2, 4, 6, 7 and 9 were evaluated. All these compounds showed cytotoxic activities against three human tumor cell lines, MDA‐MB‐231, SW620 and HepG2, with the IC50 values between 0.015 and 10.27 μm, and only 7 and 9 possessed NF‐κB inhibitory activities with the IC50 values of 2.42 and 0.046 μm, respectively, which demonstrated that 2‐alanine amino acid plays a key role to maintain the RAs bioactivity. |
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The structures were determined using various spectroscopic methods. Among them, 2 was firstly identified as a natural product, and 3–6 were firstly isolated from this species. Cytotoxicity and NF‐κB signaling pathway activity of 1, 2, 4, 6, 7 and 9 were evaluated. All these compounds showed cytotoxic activities against three human tumor cell lines, MDA‐MB‐231, SW620 and HepG2, with the IC50 values between 0.015 and 10.27 μm, and only 7 and 9 possessed NF‐κB inhibitory activities with the IC50 values of 2.42 and 0.046 μm, respectively, which demonstrated that 2‐alanine amino acid plays a key role to maintain the RAs bioactivity.</description><identifier>ISSN: 1612-1872</identifier><identifier>EISSN: 1612-1880</identifier><identifier>DOI: 10.1002/cbdv.201800438</identifier><identifier>PMID: 30334345</identifier><language>eng</language><publisher>Switzerland: Wiley Subscription Services, Inc</publisher><subject>Alanine ; Amino acids ; Biocompatibility ; Biological activity ; cyclopeptides ; Cytotoxicity ; Identification methods ; Natural products ; Rhizomes ; Rubia podantha ; rubipodanin B ; Signal transduction ; structure elucidation ; Toxicity ; Tumor cell lines</subject><ispartof>Chemistry & biodiversity, 2019-01, Vol.16 (1), p.e1800438-n/a</ispartof><rights>2019 Wiley‐VHCA AG, Zurich, Switzerland</rights><rights>2018 Wiley-VHCA AG, Zurich, Switzerland.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3738-34c4804bc20b89139cb53ca8e7131bcf0fbb3cb635cc486d2b967464f862a9433</citedby><cites>FETCH-LOGICAL-c3738-34c4804bc20b89139cb53ca8e7131bcf0fbb3cb635cc486d2b967464f862a9433</cites><orcidid>0000-0002-3731-1000</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcbdv.201800438$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcbdv.201800438$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30334345$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hu, Yan‐Yun</creatorcontrib><creatorcontrib>Feng, Li</creatorcontrib><creatorcontrib>Wang, Jia</creatorcontrib><creatorcontrib>Zhang, Xue‐Jia</creatorcontrib><creatorcontrib>Wang, Zhe</creatorcontrib><creatorcontrib>Tan, Ning‐Hua</creatorcontrib><title>Rubipodanin B, a New Cytotoxic Cyclopeptide from Rubia podantha</title><title>Chemistry & biodiversity</title><addtitle>Chem Biodivers</addtitle><description>Using the TLC cyclopeptide protosite detection method, a new cyclohexapeptide named rubipodanin B (1), together with 11 known Rubiaceae‐type cyclopeptides (RAs), RA‐X‐OMe (2), RA‐IV (3), RA‐XI (4), RA‐XIII‐OMe (5), rubiyunnanin C (6), RA‐I (7), RA‐III (8), RA‐V (9), RA‐VII (10), RA‐XII (11) and rubipodanin A (12), were obtained from the roots and rhizomes of Rubia podantha Diels. The structures were determined using various spectroscopic methods. Among them, 2 was firstly identified as a natural product, and 3–6 were firstly isolated from this species. Cytotoxicity and NF‐κB signaling pathway activity of 1, 2, 4, 6, 7 and 9 were evaluated. All these compounds showed cytotoxic activities against three human tumor cell lines, MDA‐MB‐231, SW620 and HepG2, with the IC50 values between 0.015 and 10.27 μm, and only 7 and 9 possessed NF‐κB inhibitory activities with the IC50 values of 2.42 and 0.046 μm, respectively, which demonstrated that 2‐alanine amino acid plays a key role to maintain the RAs bioactivity.</description><subject>Alanine</subject><subject>Amino acids</subject><subject>Biocompatibility</subject><subject>Biological activity</subject><subject>cyclopeptides</subject><subject>Cytotoxicity</subject><subject>Identification methods</subject><subject>Natural products</subject><subject>Rhizomes</subject><subject>Rubia podantha</subject><subject>rubipodanin B</subject><subject>Signal transduction</subject><subject>structure elucidation</subject><subject>Toxicity</subject><subject>Tumor cell lines</subject><issn>1612-1872</issn><issn>1612-1880</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqF0M1LwzAYBvAgipvTq0cpePFgZ76apifZ6icMBVGvIUlT7Gib2rTO_fdmbk7w4ikv4fc-vDwAHCM4RhDiC62yjzGGiENICd8BQ8QQDhHncHc7x3gADpybe-__-T4YEEgIJTQagsunXhWNzWRd1MH0PJDBg1kE6bKznf0stJ90aRvTdEVmgry1VbBakMH3SvcmD8FeLktnjjbvCLzcXD-nd-Hs8fY-ncxCTWLCQ0I15ZAqjaHiCSKJVhHRkpsYEaR0DnOliFaMRNpDlmGVsJgymnOGZUIJGYGzdW7T2vfeuE5UhdOmLGVtbO8ERhhHMWc89vT0D53bvq39dV4xjjGllHk1XivdWudak4umLSrZLgWCYlWtWFUrttX6hZNNbK8qk235T5ceJGuwKEqz_CdOpNOr19_wL5Hlguc</recordid><startdate>201901</startdate><enddate>201901</enddate><creator>Hu, Yan‐Yun</creator><creator>Feng, Li</creator><creator>Wang, Jia</creator><creator>Zhang, Xue‐Jia</creator><creator>Wang, Zhe</creator><creator>Tan, Ning‐Hua</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7TM</scope><scope>8FD</scope><scope>FR3</scope><scope>K9.</scope><scope>M7N</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-3731-1000</orcidid></search><sort><creationdate>201901</creationdate><title>Rubipodanin B, a New Cytotoxic Cyclopeptide from Rubia podantha</title><author>Hu, Yan‐Yun ; Feng, Li ; Wang, Jia ; Zhang, Xue‐Jia ; Wang, Zhe ; Tan, Ning‐Hua</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3738-34c4804bc20b89139cb53ca8e7131bcf0fbb3cb635cc486d2b967464f862a9433</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Alanine</topic><topic>Amino acids</topic><topic>Biocompatibility</topic><topic>Biological activity</topic><topic>cyclopeptides</topic><topic>Cytotoxicity</topic><topic>Identification methods</topic><topic>Natural products</topic><topic>Rhizomes</topic><topic>Rubia podantha</topic><topic>rubipodanin B</topic><topic>Signal transduction</topic><topic>structure elucidation</topic><topic>Toxicity</topic><topic>Tumor cell lines</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hu, Yan‐Yun</creatorcontrib><creatorcontrib>Feng, Li</creatorcontrib><creatorcontrib>Wang, Jia</creatorcontrib><creatorcontrib>Zhang, Xue‐Jia</creatorcontrib><creatorcontrib>Wang, Zhe</creatorcontrib><creatorcontrib>Tan, Ning‐Hua</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry & biodiversity</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hu, Yan‐Yun</au><au>Feng, Li</au><au>Wang, Jia</au><au>Zhang, Xue‐Jia</au><au>Wang, Zhe</au><au>Tan, Ning‐Hua</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Rubipodanin B, a New Cytotoxic Cyclopeptide from Rubia podantha</atitle><jtitle>Chemistry & biodiversity</jtitle><addtitle>Chem Biodivers</addtitle><date>2019-01</date><risdate>2019</risdate><volume>16</volume><issue>1</issue><spage>e1800438</spage><epage>n/a</epage><pages>e1800438-n/a</pages><issn>1612-1872</issn><eissn>1612-1880</eissn><abstract>Using the TLC cyclopeptide protosite detection method, a new cyclohexapeptide named rubipodanin B (1), together with 11 known Rubiaceae‐type cyclopeptides (RAs), RA‐X‐OMe (2), RA‐IV (3), RA‐XI (4), RA‐XIII‐OMe (5), rubiyunnanin C (6), RA‐I (7), RA‐III (8), RA‐V (9), RA‐VII (10), RA‐XII (11) and rubipodanin A (12), were obtained from the roots and rhizomes of Rubia podantha Diels. The structures were determined using various spectroscopic methods. Among them, 2 was firstly identified as a natural product, and 3–6 were firstly isolated from this species. Cytotoxicity and NF‐κB signaling pathway activity of 1, 2, 4, 6, 7 and 9 were evaluated. All these compounds showed cytotoxic activities against three human tumor cell lines, MDA‐MB‐231, SW620 and HepG2, with the IC50 values between 0.015 and 10.27 μm, and only 7 and 9 possessed NF‐κB inhibitory activities with the IC50 values of 2.42 and 0.046 μm, respectively, which demonstrated that 2‐alanine amino acid plays a key role to maintain the RAs bioactivity.</abstract><cop>Switzerland</cop><pub>Wiley Subscription Services, Inc</pub><pmid>30334345</pmid><doi>10.1002/cbdv.201800438</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-3731-1000</orcidid></addata></record> |
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subjects | Alanine Amino acids Biocompatibility Biological activity cyclopeptides Cytotoxicity Identification methods Natural products Rhizomes Rubia podantha rubipodanin B Signal transduction structure elucidation Toxicity Tumor cell lines |
title | Rubipodanin B, a New Cytotoxic Cyclopeptide from Rubia podantha |
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