Chuanxiongdiolides R4 and R5, phthalide dimers with a complex polycyclic skeleton from the aerial parts of Ligusticum chuanxiong and their vasodilator activity
[Display omitted] •Three novel phthalide dimers were isolated from the aerial parts of L. chuanxiong.•Compounds 1, 3, 4, 5, and 6 showed significant vasodilation effects.•Compounds 1, 3, and 5a showed the obvious Cav1.2 block activity.•The structure-activity relationship of phthalide dimers in vasod...
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| Veröffentlicht in: | Bioorganic chemistry 2021-02, Vol.107, p.104523-104523, Article 104523 |
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| creator | Tang, Fei Yan, Yong-Ming Yan, Hong-Ling Wang, Li-Xia Hu, Chang-Jiang Wang, Hong-Liang Ao, Hui Peng, Cheng Tan, Yu-Zhu |
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•Three novel phthalide dimers were isolated from the aerial parts of L. chuanxiong.•Compounds 1, 3, 4, 5, and 6 showed significant vasodilation effects.•Compounds 1, 3, and 5a showed the obvious Cav1.2 block activity.•The structure-activity relationship of phthalide dimers in vasodilation was discussed.
Chuanxiongdiolides R4-R6 (1–3), three novel phthalide dimers featuring two classes of unreported monomeric units (ligustilide/senkyunolide A and ligustilide/neocnidilide) with an unprecedented linkage style (3a,7′/7a,7′a), were isolated from the aerial parts of Ligusticum chuanxiong, together with three pairs of enantiomeric phthalide dimers [(−)/(+)-4a/4b, 5a/5b, and 6a/6b]. The bioassays revealed that compounds 1, 3, 4, 5, and 6 showed significant vasodilation effects, and the mechanism may be attributed to Cav1.2 activation blockade. Based on the established compounds library, the structure activity relationship of the phthalides was proposed. Our findings afford possible leads for developing new vasodilator against cardiovascular and cerebrovascular diseases such as hypertension and ischemic stroke. |
| doi_str_mv | 10.1016/j.bioorg.2020.104523 |
| format | Article |
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•Three novel phthalide dimers were isolated from the aerial parts of L. chuanxiong.•Compounds 1, 3, 4, 5, and 6 showed significant vasodilation effects.•Compounds 1, 3, and 5a showed the obvious Cav1.2 block activity.•The structure-activity relationship of phthalide dimers in vasodilation was discussed.
Chuanxiongdiolides R4-R6 (1–3), three novel phthalide dimers featuring two classes of unreported monomeric units (ligustilide/senkyunolide A and ligustilide/neocnidilide) with an unprecedented linkage style (3a,7′/7a,7′a), were isolated from the aerial parts of Ligusticum chuanxiong, together with three pairs of enantiomeric phthalide dimers [(−)/(+)-4a/4b, 5a/5b, and 6a/6b]. The bioassays revealed that compounds 1, 3, 4, 5, and 6 showed significant vasodilation effects, and the mechanism may be attributed to Cav1.2 activation blockade. Based on the established compounds library, the structure activity relationship of the phthalides was proposed. Our findings afford possible leads for developing new vasodilator against cardiovascular and cerebrovascular diseases such as hypertension and ischemic stroke.</description><identifier>ISSN: 0045-2068</identifier><identifier>EISSN: 1090-2120</identifier><identifier>DOI: 10.1016/j.bioorg.2020.104523</identifier><identifier>PMID: 33339668</identifier><language>eng</language><publisher>United States: Elsevier Inc</publisher><subject>Animals ; Benzofurans - chemistry ; Benzofurans - isolation & purification ; Benzofurans - metabolism ; Benzofurans - pharmacology ; Calcium Channel Blockers - chemistry ; Calcium Channel Blockers - isolation & purification ; Calcium Channel Blockers - metabolism ; Calcium Channel Blockers - pharmacology ; Calcium Channels, L-Type - metabolism ; Cav1.2 channel blockade ; HEK293 Cells ; Heterocyclic Compounds, Bridged-Ring - chemical synthesis ; Heterocyclic Compounds, Bridged-Ring - isolation & purification ; Heterocyclic Compounds, Bridged-Ring - metabolism ; Heterocyclic Compounds, Bridged-Ring - pharmacology ; Humans ; Ligusticum - chemistry ; Molecular Docking Simulation ; Molecular Structure ; Phthalide dimers ; Plant Components, Aerial - chemistry ; Protein Binding ; Rabbits ; Rats ; Rats, Sprague-Dawley ; Stereoisomerism ; Structure-Activity Relationship ; The aerial parts of Ligusticum chuanxiong ; Vasodilation activity ; Vasodilator Agents - chemistry ; Vasodilator Agents - isolation & purification ; Vasodilator Agents - metabolism ; Vasodilator Agents - pharmacology</subject><ispartof>Bioorganic chemistry, 2021-02, Vol.107, p.104523-104523, Article 104523</ispartof><rights>2020 Elsevier Inc.</rights><rights>Copyright © 2020 Elsevier Inc. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c362t-64732c2b13e23590a6c9b74e5ed69b2308aeebaddc0c00c665ac5bb4632de0343</citedby><cites>FETCH-LOGICAL-c362t-64732c2b13e23590a6c9b74e5ed69b2308aeebaddc0c00c665ac5bb4632de0343</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bioorg.2020.104523$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33339668$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tang, Fei</creatorcontrib><creatorcontrib>Yan, Yong-Ming</creatorcontrib><creatorcontrib>Yan, Hong-Ling</creatorcontrib><creatorcontrib>Wang, Li-Xia</creatorcontrib><creatorcontrib>Hu, Chang-Jiang</creatorcontrib><creatorcontrib>Wang, Hong-Liang</creatorcontrib><creatorcontrib>Ao, Hui</creatorcontrib><creatorcontrib>Peng, Cheng</creatorcontrib><creatorcontrib>Tan, Yu-Zhu</creatorcontrib><title>Chuanxiongdiolides R4 and R5, phthalide dimers with a complex polycyclic skeleton from the aerial parts of Ligusticum chuanxiong and their vasodilator activity</title><title>Bioorganic chemistry</title><addtitle>Bioorg Chem</addtitle><description>[Display omitted]
•Three novel phthalide dimers were isolated from the aerial parts of L. chuanxiong.•Compounds 1, 3, 4, 5, and 6 showed significant vasodilation effects.•Compounds 1, 3, and 5a showed the obvious Cav1.2 block activity.•The structure-activity relationship of phthalide dimers in vasodilation was discussed.
Chuanxiongdiolides R4-R6 (1–3), three novel phthalide dimers featuring two classes of unreported monomeric units (ligustilide/senkyunolide A and ligustilide/neocnidilide) with an unprecedented linkage style (3a,7′/7a,7′a), were isolated from the aerial parts of Ligusticum chuanxiong, together with three pairs of enantiomeric phthalide dimers [(−)/(+)-4a/4b, 5a/5b, and 6a/6b]. The bioassays revealed that compounds 1, 3, 4, 5, and 6 showed significant vasodilation effects, and the mechanism may be attributed to Cav1.2 activation blockade. Based on the established compounds library, the structure activity relationship of the phthalides was proposed. Our findings afford possible leads for developing new vasodilator against cardiovascular and cerebrovascular diseases such as hypertension and ischemic stroke.</description><subject>Animals</subject><subject>Benzofurans - chemistry</subject><subject>Benzofurans - isolation & purification</subject><subject>Benzofurans - metabolism</subject><subject>Benzofurans - pharmacology</subject><subject>Calcium Channel Blockers - chemistry</subject><subject>Calcium Channel Blockers - isolation & purification</subject><subject>Calcium Channel Blockers - metabolism</subject><subject>Calcium Channel Blockers - pharmacology</subject><subject>Calcium Channels, L-Type - metabolism</subject><subject>Cav1.2 channel blockade</subject><subject>HEK293 Cells</subject><subject>Heterocyclic Compounds, Bridged-Ring - chemical synthesis</subject><subject>Heterocyclic Compounds, Bridged-Ring - isolation & purification</subject><subject>Heterocyclic Compounds, Bridged-Ring - metabolism</subject><subject>Heterocyclic Compounds, Bridged-Ring - pharmacology</subject><subject>Humans</subject><subject>Ligusticum - chemistry</subject><subject>Molecular Docking Simulation</subject><subject>Molecular Structure</subject><subject>Phthalide dimers</subject><subject>Plant Components, Aerial - chemistry</subject><subject>Protein Binding</subject><subject>Rabbits</subject><subject>Rats</subject><subject>Rats, Sprague-Dawley</subject><subject>Stereoisomerism</subject><subject>Structure-Activity Relationship</subject><subject>The aerial parts of Ligusticum chuanxiong</subject><subject>Vasodilation activity</subject><subject>Vasodilator Agents - chemistry</subject><subject>Vasodilator Agents - isolation & purification</subject><subject>Vasodilator Agents - metabolism</subject><subject>Vasodilator Agents - pharmacology</subject><issn>0045-2068</issn><issn>1090-2120</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kV2LEzEUhoMobnf1H4jk0gun5mvSzo0gRV2hICx6HTLJaXtqZjImmbr9Nf5Vp866l56bwMtzzkt4CHnF2ZIzrt8dly3GmPZLwcQlUrWQT8iCs4ZVggv2lCzYFFaC6fUVuc75yBjnaqWfkys5TaP1ekF-bw6j7e8x9nuPMaCHTO8Utb2nd_VbOhzKwV5S6rGDlOkvLAdqqYvdEOCeDjGc3dkFdDT_gAAl9nSXYkfLAaiFhDbQwaaSadzRLe7HXNCNHXWPrX-rJhoTPdkcPQZbYqLWFTxhOb8gz3Y2ZHj58N6Q758-ftvcVtuvn79sPmwrJ7UolVYrKZxouQQh64ZZ7Zp2paAGr5tWSLa2AK313jHHmNO6tq5uW6Wl8MCkkjfkzXx3SPHnCLmYDrODEGwPccxGqBVXWjRST6iaUZdizgl2ZkjY2XQ2nJmLGnM0sxpzUWNmNdPa64eGse3APy79czEB72cApn-eEJLJDqF34DGBK8ZH_H_DH7jPpOU</recordid><startdate>202102</startdate><enddate>202102</enddate><creator>Tang, Fei</creator><creator>Yan, Yong-Ming</creator><creator>Yan, Hong-Ling</creator><creator>Wang, Li-Xia</creator><creator>Hu, Chang-Jiang</creator><creator>Wang, Hong-Liang</creator><creator>Ao, Hui</creator><creator>Peng, Cheng</creator><creator>Tan, Yu-Zhu</creator><general>Elsevier Inc</general><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>202102</creationdate><title>Chuanxiongdiolides R4 and R5, phthalide dimers with a complex polycyclic skeleton from the aerial parts of Ligusticum chuanxiong and their vasodilator activity</title><author>Tang, Fei ; Yan, Yong-Ming ; Yan, Hong-Ling ; Wang, Li-Xia ; Hu, Chang-Jiang ; Wang, Hong-Liang ; Ao, Hui ; Peng, Cheng ; Tan, Yu-Zhu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c362t-64732c2b13e23590a6c9b74e5ed69b2308aeebaddc0c00c665ac5bb4632de0343</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Animals</topic><topic>Benzofurans - chemistry</topic><topic>Benzofurans - isolation & purification</topic><topic>Benzofurans - metabolism</topic><topic>Benzofurans - pharmacology</topic><topic>Calcium Channel Blockers - chemistry</topic><topic>Calcium Channel Blockers - isolation & purification</topic><topic>Calcium Channel Blockers - metabolism</topic><topic>Calcium Channel Blockers - pharmacology</topic><topic>Calcium Channels, L-Type - metabolism</topic><topic>Cav1.2 channel blockade</topic><topic>HEK293 Cells</topic><topic>Heterocyclic Compounds, Bridged-Ring - chemical synthesis</topic><topic>Heterocyclic Compounds, Bridged-Ring - isolation & purification</topic><topic>Heterocyclic Compounds, Bridged-Ring - metabolism</topic><topic>Heterocyclic Compounds, Bridged-Ring - pharmacology</topic><topic>Humans</topic><topic>Ligusticum - chemistry</topic><topic>Molecular Docking Simulation</topic><topic>Molecular Structure</topic><topic>Phthalide dimers</topic><topic>Plant Components, Aerial - chemistry</topic><topic>Protein Binding</topic><topic>Rabbits</topic><topic>Rats</topic><topic>Rats, Sprague-Dawley</topic><topic>Stereoisomerism</topic><topic>Structure-Activity Relationship</topic><topic>The aerial parts of Ligusticum chuanxiong</topic><topic>Vasodilation activity</topic><topic>Vasodilator Agents - chemistry</topic><topic>Vasodilator Agents - isolation & purification</topic><topic>Vasodilator Agents - metabolism</topic><topic>Vasodilator Agents - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tang, Fei</creatorcontrib><creatorcontrib>Yan, Yong-Ming</creatorcontrib><creatorcontrib>Yan, Hong-Ling</creatorcontrib><creatorcontrib>Wang, Li-Xia</creatorcontrib><creatorcontrib>Hu, Chang-Jiang</creatorcontrib><creatorcontrib>Wang, Hong-Liang</creatorcontrib><creatorcontrib>Ao, Hui</creatorcontrib><creatorcontrib>Peng, Cheng</creatorcontrib><creatorcontrib>Tan, Yu-Zhu</creatorcontrib><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>Bioorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tang, Fei</au><au>Yan, Yong-Ming</au><au>Yan, Hong-Ling</au><au>Wang, Li-Xia</au><au>Hu, Chang-Jiang</au><au>Wang, Hong-Liang</au><au>Ao, Hui</au><au>Peng, Cheng</au><au>Tan, Yu-Zhu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chuanxiongdiolides R4 and R5, phthalide dimers with a complex polycyclic skeleton from the aerial parts of Ligusticum chuanxiong and their vasodilator activity</atitle><jtitle>Bioorganic chemistry</jtitle><addtitle>Bioorg Chem</addtitle><date>2021-02</date><risdate>2021</risdate><volume>107</volume><spage>104523</spage><epage>104523</epage><pages>104523-104523</pages><artnum>104523</artnum><issn>0045-2068</issn><eissn>1090-2120</eissn><abstract>[Display omitted]
•Three novel phthalide dimers were isolated from the aerial parts of L. chuanxiong.•Compounds 1, 3, 4, 5, and 6 showed significant vasodilation effects.•Compounds 1, 3, and 5a showed the obvious Cav1.2 block activity.•The structure-activity relationship of phthalide dimers in vasodilation was discussed.
Chuanxiongdiolides R4-R6 (1–3), three novel phthalide dimers featuring two classes of unreported monomeric units (ligustilide/senkyunolide A and ligustilide/neocnidilide) with an unprecedented linkage style (3a,7′/7a,7′a), were isolated from the aerial parts of Ligusticum chuanxiong, together with three pairs of enantiomeric phthalide dimers [(−)/(+)-4a/4b, 5a/5b, and 6a/6b]. The bioassays revealed that compounds 1, 3, 4, 5, and 6 showed significant vasodilation effects, and the mechanism may be attributed to Cav1.2 activation blockade. Based on the established compounds library, the structure activity relationship of the phthalides was proposed. Our findings afford possible leads for developing new vasodilator against cardiovascular and cerebrovascular diseases such as hypertension and ischemic stroke.</abstract><cop>United States</cop><pub>Elsevier Inc</pub><pmid>33339668</pmid><doi>10.1016/j.bioorg.2020.104523</doi><tpages>1</tpages></addata></record> |
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| subjects | Animals Benzofurans - chemistry Benzofurans - isolation & purification Benzofurans - metabolism Benzofurans - pharmacology Calcium Channel Blockers - chemistry Calcium Channel Blockers - isolation & purification Calcium Channel Blockers - metabolism Calcium Channel Blockers - pharmacology Calcium Channels, L-Type - metabolism Cav1.2 channel blockade HEK293 Cells Heterocyclic Compounds, Bridged-Ring - chemical synthesis Heterocyclic Compounds, Bridged-Ring - isolation & purification Heterocyclic Compounds, Bridged-Ring - metabolism Heterocyclic Compounds, Bridged-Ring - pharmacology Humans Ligusticum - chemistry Molecular Docking Simulation Molecular Structure Phthalide dimers Plant Components, Aerial - chemistry Protein Binding Rabbits Rats Rats, Sprague-Dawley Stereoisomerism Structure-Activity Relationship The aerial parts of Ligusticum chuanxiong Vasodilation activity Vasodilator Agents - chemistry Vasodilator Agents - isolation & purification Vasodilator Agents - metabolism Vasodilator Agents - pharmacology |
| title | Chuanxiongdiolides R4 and R5, phthalide dimers with a complex polycyclic skeleton from the aerial parts of Ligusticum chuanxiong and their vasodilator activity |
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