Daphneodorins A–C, Anti-HIV Gnidimacrin Related Macrocyclic Daphnane Orthoesters from Daphne odora
Three novel gnidimacrin related macrocyclic daphnanes (GMDs), daphneodorins A–C (2–4), were isolated from Daphne odora Thunb., together with gnidimacrin (1). Their structures were established by extensive physicochemical and spectroscopic analyses. Compounds 2 and 3 potently inhibited HIV-1 replicat...
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| Published in | Organic letters Vol. 22; no. 1; pp. 11 - 15 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
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American Chemical Society
03.01.2020
Amer Chemical Soc |
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| Abstract | Three novel gnidimacrin related macrocyclic daphnanes (GMDs), daphneodorins A–C (2–4), were isolated from Daphne odora Thunb., together with gnidimacrin (1). Their structures were established by extensive physicochemical and spectroscopic analyses. Compounds 2 and 3 potently inhibited HIV-1 replication at subnanomolar concentrations (EC50 0.16 and 0.25 nM, respectively). Compounds 2–4 represent a novel type of GMDs that are highly oxygenated on the macrocyclic ring, suggesting good potential for anti-HIV drug development by further chemical modification. |
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| AbstractList | Three novel gnidimacrin related macrocyclic daphnanes (GMDs), daphneodorins A–C (2–4), were isolated from Daphne odora Thunb., together with gnidimacrin (1). Their structures were established by extensive physicochemical and spectroscopic analyses. Compounds 2 and 3 potently inhibited HIV-1 replication at subnanomolar concentrations (EC₅₀ 0.16 and 0.25 nM, respectively). Compounds 2–4 represent a novel type of GMDs that are highly oxygenated on the macrocyclic ring, suggesting good potential for anti-HIV drug development by further chemical modification. Three novel gnidimacrin related macrocyclic daphnanes (GMDs), daphneodorins A–C (2–4), were isolated from Daphne odora Thunb., together with gnidimacrin (1). Their structures were established by extensive physicochemical and spectroscopic analyses. Compounds 2 and 3 potently inhibited HIV-1 replication at subnanomolar concentrations (EC50 0.16 and 0.25 nM, respectively). Compounds 2–4 represent a novel type of GMDs that are highly oxygenated on the macrocyclic ring, suggesting good potential for anti-HIV drug development by further chemical modification. Three novel gnidimacrin related macrocyclic daphnanes (GMDs), daphneodorins A–C ( 2–4 ), were isolated from Daphne odora Thunb., together with gnidimacrin ( 1 ). Their structures were established by extensive physicochemical and spectroscopic analyses. Compounds 2 and 3 potently inhibited HIV-1 replication at subnanomolar concentrations (EC 50 0.16 and 0.25 nM, respectively). Compounds 2–4 represent a novel type of GMDs that are highly oxygenated on the macrocyclic ring, suggesting good potential for anti-HIV drug development by further chemical modification. Three novel gnidimacrin related macrocyclic daphnanes (GMDs), daphneodorins A-C ( - ), were isolated from Thunb., together with gnidimacrin ( ). Their structures were established by extensive physicochemical and spectroscopic analyses. Compounds and potently inhibited HIV-1 replication at subnanomolar concentrations (EC 0.16 and 0.25 nM, respectively). Compounds - represent a novel type of GMDs that are highly oxygenated on the macrocyclic ring, suggesting good potential for anti-HIV drug development by further chemical modification. Three novel gnidimacrin related macrocyclic daphnanes (GMDs), daphneodorins A-C (2-4), were isolated from Daphne odora Thunb., together with gnidimacrin (1). Their structures were established by extensive physicochemicai and spectroscopic analyses. Compounds 2 and 3 potently inhibited HIV-1 replication at subnanomolar concentrations (EC50 0.16 and 0.25 nM, respectively). Compounds 2-4 represent a novel type of GMDs that are highly oxygenated on the macrocyclic ring, suggesting good potential for anti-HIV drug development by further chemical modification. Three novel gnidimacrin related macrocyclic daphnanes (GMDs), daphneodorins A-C (2-4), were isolated from Daphne odora Thunb., together with gnidimacrin (1). Their structures were established by extensive physicochemical and spectroscopic analyses. Compounds 2 and 3 potently inhibited HIV-1 replication at subnanomolar concentrations (EC50 0.16 and 0.25 nM, respectively). Compounds 2-4 represent a novel type of GMDs that are highly oxygenated on the macrocyclic ring, suggesting good potential for anti-HIV drug development by further chemical modification.Three novel gnidimacrin related macrocyclic daphnanes (GMDs), daphneodorins A-C (2-4), were isolated from Daphne odora Thunb., together with gnidimacrin (1). Their structures were established by extensive physicochemical and spectroscopic analyses. Compounds 2 and 3 potently inhibited HIV-1 replication at subnanomolar concentrations (EC50 0.16 and 0.25 nM, respectively). Compounds 2-4 represent a novel type of GMDs that are highly oxygenated on the macrocyclic ring, suggesting good potential for anti-HIV drug development by further chemical modification. |
| Author | Li, Wei Koike, Kazuo Chen, Chin-Ho Otsuki, Kouharu Asada, Yoshihisa Lee, Kuo-Hsiung |
| AuthorAffiliation | Natural Products Research Laboratories, UNC Eshelman School of Pharmacy Surgical Science, Department of Surgery Faculty of Pharmaceutical Sciences Chinese Medicine Research and Development Center University of North Carolina China Medical University and Hospital |
| AuthorAffiliation_xml | – name: Natural Products Research Laboratories, UNC Eshelman School of Pharmacy – name: Surgical Science, Department of Surgery – name: University of North Carolina – name: China Medical University and Hospital – name: Faculty of Pharmaceutical Sciences – name: Chinese Medicine Research and Development Center – name: Faculty of Pharmaceutical Sciences, Toho University, Miyama 2-2-1, Funabashi, Chiba 274-8510, Japan – name: Chinese Medicine Research and Development Center, China Medical University and Hospital, Tiachung, 40447, Taiwan – name: Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina 27599, United States – name: Surgical Science, Department of Surgery, Duke University Medical Center, Durham, North Carolina 27710, United States |
| Author_xml | – sequence: 1 givenname: Kouharu surname: Otsuki fullname: Otsuki, Kouharu organization: Faculty of Pharmaceutical Sciences – sequence: 2 givenname: Wei orcidid: 0000-0003-4143-8597 surname: Li fullname: Li, Wei email: liwei@phar.toho-u.ac.jp organization: Faculty of Pharmaceutical Sciences – sequence: 3 givenname: Yoshihisa surname: Asada fullname: Asada, Yoshihisa organization: Faculty of Pharmaceutical Sciences – sequence: 4 givenname: Chin-Ho orcidid: 0000-0001-6880-2104 surname: Chen fullname: Chen, Chin-Ho organization: Surgical Science, Department of Surgery – sequence: 5 givenname: Kuo-Hsiung orcidid: 0000-0002-6562-0070 surname: Lee fullname: Lee, Kuo-Hsiung organization: China Medical University and Hospital – sequence: 6 givenname: Kazuo surname: Koike fullname: Koike, Kazuo organization: Faculty of Pharmaceutical Sciences |
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| Snippet | Three novel gnidimacrin related macrocyclic daphnanes (GMDs), daphneodorins A–C (2–4), were isolated from Daphne odora Thunb., together with gnidimacrin (1).... Three novel gnidimacrin related macrocyclic daphnanes (GMDs), daphneodorins A-C (2-4), were isolated from Daphne odora Thunb., together with gnidimacrin (1).... Three novel gnidimacrin related macrocyclic daphnanes (GMDs), daphneodorins A-C ( - ), were isolated from Thunb., together with gnidimacrin ( ). Their... Three novel gnidimacrin related macrocyclic daphnanes (GMDs), daphneodorins A–C ( 2–4 ), were isolated from Daphne odora Thunb., together with gnidimacrin ( 1... |
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| SubjectTerms | Anti-HIV Agents - chemistry Anti-HIV Agents - isolation & purification Anti-HIV Agents - pharmacology antiretroviral agents chemical reactions chemical structure Chemistry Chemistry, Organic Daphne - chemistry Daphne odora Dose-Response Relationship, Drug drug development HIV-1 - drug effects Human immunodeficiency virus 1 Macrocyclic Compounds - chemistry Macrocyclic Compounds - isolation & purification Macrocyclic Compounds - pharmacology median effective concentration Microbial Sensitivity Tests Molecular Conformation ortho esters Physical Sciences Science & Technology spectral analysis Structure-Activity Relationship virus replication Virus Replication - drug effects |
| Title | Daphneodorins A–C, Anti-HIV Gnidimacrin Related Macrocyclic Daphnane Orthoesters from Daphne odora |
| URI | http://dx.doi.org/10.1021/acs.orglett.9b03539 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000506088700003 https://www.ncbi.nlm.nih.gov/pubmed/31680527 https://www.proquest.com/docview/2311921795 https://www.proquest.com/docview/2388743334 https://pubmed.ncbi.nlm.nih.gov/PMC7437546 |
| Volume | 22 |
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