Anti-HIV Macrocyclic Daphnane Orthoesters with an Unusual Macrocyclic Ring from Edgeworthia chrysantha
Edgeworthianins A–E (1–5) were isolated from Edgeworthia chrysantha as a class of macrocyclic daphnane orthoesters with an unusual macrocyclic ring formed from a C14 aliphatic chain. Their structures were elucidated by extensive physicochemical and spectroscopic analyses. Compounds 2, 4, and 5 exhib...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2022-10, Vol.85 (10), p.2399-2405 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | Asada, Yoshihisa Otsuki, Kouharu Morooka, Miki Huang, Li Chen, Chin-Ho Koike, Kazuo Li, Wei |
| description | Edgeworthianins A–E (1–5) were isolated from Edgeworthia chrysantha as a class of macrocyclic daphnane orthoesters with an unusual macrocyclic ring formed from a C14 aliphatic chain. Their structures were elucidated by extensive physicochemical and spectroscopic analyses. Compounds 2, 4, and 5 exhibited potent anti-HIV activity against HIV-1 infection of MT4 cells with EC50 values of 29.3, 8.4, and 2.9 nM, respectively. These compounds broaden the findings of the structure–activity relationship of macrocyclic daphnane orthoesters for further anti-HIV drug development. |
| doi_str_mv | 10.1021/acs.jnatprod.2c00618 |
| format | Article |
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Their structures were elucidated by extensive physicochemical and spectroscopic analyses. Compounds 2, 4, and 5 exhibited potent anti-HIV activity against HIV-1 infection of MT4 cells with EC50 values of 29.3, 8.4, and 2.9 nM, respectively. 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Nat. Prod</addtitle><description>Edgeworthianins A–E (1–5) were isolated from Edgeworthia chrysantha as a class of macrocyclic daphnane orthoesters with an unusual macrocyclic ring formed from a C14 aliphatic chain. Their structures were elucidated by extensive physicochemical and spectroscopic analyses. Compounds 2, 4, and 5 exhibited potent anti-HIV activity against HIV-1 infection of MT4 cells with EC50 values of 29.3, 8.4, and 2.9 nM, respectively. These compounds broaden the findings of the structure–activity relationship of macrocyclic daphnane orthoesters for further anti-HIV drug development.</description><subject>Anti-HIV Agents - chemistry</subject><subject>Anti-HIV Agents - pharmacology</subject><subject>antiretroviral agents</subject><subject>antiretroviral properties</subject><subject>Diterpenes - chemistry</subject><subject>drug development</subject><subject>Edgeworthia</subject><subject>HIV infections</subject><subject>Molecular Structure</subject><subject>ortho esters</subject><subject>spectroscopy</subject><subject>Structure-Activity Relationship</subject><subject>structure-activity relationships</subject><subject>Thymelaeaceae - chemistry</subject><issn>0163-3864</issn><issn>1520-6025</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kUFPGzEQha2qqKSBf4CQj71sGK93nfWpQpRCJCokBFytidfOGm3s1N4tyr-vaQKCS08-zPveeN4j5ITBjEHJzlCn2ZPHYRNDOys1gGDNJzJhdQmFgLL-TCbABC94I6pD8jWlJwDgIOsv5JALJmQJ1YTYcz-44nrxSH-hjkFvde80_YGbzqM39DYOXTBpMDHRZzd0FD198GMasf8A3Dm_ojaGNb1sV-Y5ZMwh1V3cJvRDh0fkwGKfzPH-nZKHn5f3F9fFze3V4uL8psCq4UMhjOGS5UOYrSxHK4AvoWWAdVNLy_Uc-byU87axQsh6yedCWm1YpZtSWGNbPiXfd76bcbk2rTZ-iNirTXRrjFsV0KmPE-86tQp_FAPGqlLy7PBt7xDD7zGfrtYuadP3OY4wJsVZzRsu88IsrXbSnENK0di3PQzUS0cqd6ReO1L7jjJ2-v6Pb9BrKVkAO8E_PIzR58j-7_kX-4Ojhg</recordid><startdate>20221028</startdate><enddate>20221028</enddate><creator>Asada, Yoshihisa</creator><creator>Otsuki, Kouharu</creator><creator>Morooka, Miki</creator><creator>Huang, Li</creator><creator>Chen, Chin-Ho</creator><creator>Koike, Kazuo</creator><creator>Li, Wei</creator><general>American Chemical Society and American Society of Pharmacognosy</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>7S9</scope><scope>L.6</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0001-6730-0663</orcidid><orcidid>https://orcid.org/0000-0003-4143-8597</orcidid><orcidid>https://orcid.org/0000-0001-6880-2104</orcidid></search><sort><creationdate>20221028</creationdate><title>Anti-HIV Macrocyclic Daphnane Orthoesters with an Unusual Macrocyclic Ring from Edgeworthia chrysantha</title><author>Asada, Yoshihisa ; Otsuki, Kouharu ; Morooka, Miki ; Huang, Li ; Chen, Chin-Ho ; Koike, Kazuo ; Li, Wei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a483t-6ee3916181f4f3af603b0d10a5859f3c7a37297d8f6695b3769fce14c826fefd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Anti-HIV Agents - chemistry</topic><topic>Anti-HIV Agents - pharmacology</topic><topic>antiretroviral agents</topic><topic>antiretroviral properties</topic><topic>Diterpenes - chemistry</topic><topic>drug development</topic><topic>Edgeworthia</topic><topic>HIV infections</topic><topic>Molecular Structure</topic><topic>ortho esters</topic><topic>spectroscopy</topic><topic>Structure-Activity Relationship</topic><topic>structure-activity relationships</topic><topic>Thymelaeaceae - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Asada, Yoshihisa</creatorcontrib><creatorcontrib>Otsuki, Kouharu</creatorcontrib><creatorcontrib>Morooka, Miki</creatorcontrib><creatorcontrib>Huang, Li</creatorcontrib><creatorcontrib>Chen, Chin-Ho</creatorcontrib><creatorcontrib>Koike, Kazuo</creatorcontrib><creatorcontrib>Li, Wei</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Asada, Yoshihisa</au><au>Otsuki, Kouharu</au><au>Morooka, Miki</au><au>Huang, Li</au><au>Chen, Chin-Ho</au><au>Koike, Kazuo</au><au>Li, Wei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Anti-HIV Macrocyclic Daphnane Orthoesters with an Unusual Macrocyclic Ring from Edgeworthia chrysantha</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2022-10-28</date><risdate>2022</risdate><volume>85</volume><issue>10</issue><spage>2399</spage><epage>2405</epage><pages>2399-2405</pages><issn>0163-3864</issn><issn>1520-6025</issn><eissn>1520-6025</eissn><abstract>Edgeworthianins A–E (1–5) were isolated from Edgeworthia chrysantha as a class of macrocyclic daphnane orthoesters with an unusual macrocyclic ring formed from a C14 aliphatic chain. Their structures were elucidated by extensive physicochemical and spectroscopic analyses. Compounds 2, 4, and 5 exhibited potent anti-HIV activity against HIV-1 infection of MT4 cells with EC50 values of 29.3, 8.4, and 2.9 nM, respectively. 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| source | ACS_美国化学学会期刊（与NSTL共建）; MEDLINE |
| subjects | Anti-HIV Agents - chemistry Anti-HIV Agents - pharmacology antiretroviral agents antiretroviral properties Diterpenes - chemistry drug development Edgeworthia HIV infections Molecular Structure ortho esters spectroscopy Structure-Activity Relationship structure-activity relationships Thymelaeaceae - chemistry |
| title | Anti-HIV Macrocyclic Daphnane Orthoesters with an Unusual Macrocyclic Ring from Edgeworthia chrysantha |
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