Identification, structural modification, and dichotomous effects on human immunodeficiency virus type 1 (HIV-1) replication of ingenane esters from Euphorbia kansui

Euphorbia kansui showed potent anti-HIV-1 activity during screening of a library composed of plant extracts from Euphorbiaceae and Thymelaeaceae families. Bioassay-guided isolation led to identification of ingenane esters as the active compounds. Further chemical modification resulted in 3-(2-naphth...

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Published in	European journal of medicinal chemistry Vol. 156; pp. 618 - 627
Main Authors	Liu, Qingbo, Li, Wei, Huang, Li, Asada, Yoshihisa, Morris-Natschke, Susan L., Chen, Chin-Ho, Lee, Kuo-Hsiung, Koike, Kazuo
Format	Journal Article
Language	English
Published	ISSY-LES-MOULINEAUX Elsevier Masson SAS 05.08.2018 Elsevier
Subjects	3-(2-Naphthoyl)ingenol Anti-HIV Antiviral Agents - chemistry Antiviral Agents - isolation & purification Antiviral Agents - pharmacology Cell Line Chemistry, Medicinal Diterpenes - chemistry Diterpenes - isolation & purification Diterpenes - pharmacology Esters - chemistry Esters - isolation & purification Esters - pharmacology Euphorbia - chemistry Euphorbia kansui HIV Infections - drug therapy HIV-1 - drug effects HIV-1 - physiology Humans Ingenane Latency-reversing agent Life Sciences & Biomedicine Pharmacology & Pharmacy Plant Extracts - chemistry Plant Extracts - isolation & purification Plant Extracts - pharmacology Science & Technology Virus Replication - drug effects Euphorbia kansui 3-(2-Naphthoyl)ingenol Anti-HIV Ingenane Latency-reversing agent DITERPENES ACTIVATION ROOTS ANTIRETROVIRAL THERAPY LATENCY EXPRESSION
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Abstract	Euphorbia kansui showed potent anti-HIV-1 activity during screening of a library composed of plant extracts from Euphorbiaceae and Thymelaeaceae families. Bioassay-guided isolation led to identification of ingenane esters as the active compounds. Further chemical modification resulted in 3-(2-naphthoyl)ingenol (23), which exhibited the most potent anti-HIV-1 activity. Compound 23 also acted as an HIV-1-latency-reversing agent on activation of HIV-1 replication in a latently infected U1 cell model and a T cell latent HIV-1 model JLat-A2. [Display omitted] •MeOH extract of Euphorbia kansui showed potent anti-HIV-1 activity.•Ingenane esters from Euphorbia kansui are potent anti-HIV-1 agents.•Naphthoyl group at C-3 of 20-deoxyingenol and ingenol enhanced anti-HIV-1 activity.•3-(2-Naphthoyl)ingenol is a potent HIV-1 latency reversing agent.
AbstractList	Euphorbia kansui showed potent anti-HIV-1 activity during screening of a library composed of plant extracts from Euphorbiaceae and Thymelaeaceae families. Bioassay-guided isolation led to identification of ingenane esters as the active compounds. Further chemical modification resulted in 3-(2-naphthoyl)ingenol (23), which exhibited the most potent anti-HIV-1 activity. Compound 23 also acted as an HIV-1-latency-reversing agent on activation of HIV-1 replication in a latently infected U1 cell model and a T cell latent HIV-1 model JLat-A2. [Display omitted] •MeOH extract of Euphorbia kansui showed potent anti-HIV-1 activity.•Ingenane esters from Euphorbia kansui are potent anti-HIV-1 agents.•Naphthoyl group at C-3 of 20-deoxyingenol and ingenol enhanced anti-HIV-1 activity.•3-(2-Naphthoyl)ingenol is a potent HIV-1 latency reversing agent. Euphorbia kansui showed potent anti-HIV-1 activity during screening of a library composed of plant extracts from Euphorbiaceae and Thymelaeaceae families. Bioassay-guided isolation led to identification of ingenane esters as the active compounds. Further chemical modification resulted in 3-(2-naphthoyl)ingenol (23), which exhibited the most potent anti-HIV-1 activity. Compound 23 also acted as an HIV-1-latency-reversing agent on activation of HIV-1 replication in a latently infected U1 cell model and a T cell latent HIV-1 model JLat-A2.Euphorbia kansui showed potent anti-HIV-1 activity during screening of a library composed of plant extracts from Euphorbiaceae and Thymelaeaceae families. Bioassay-guided isolation led to identification of ingenane esters as the active compounds. Further chemical modification resulted in 3-(2-naphthoyl)ingenol (23), which exhibited the most potent anti-HIV-1 activity. Compound 23 also acted as an HIV-1-latency-reversing agent on activation of HIV-1 replication in a latently infected U1 cell model and a T cell latent HIV-1 model JLat-A2. Euphorbia kansui showed potent anti-HIV-1 activity during screening of a library composed of plant extracts from Euphorbiaceae and Thymelaeaceae families. Bioassay-guided isolation led to identification of ingenane esters as the active compounds. Further chemical modification resulted in 3-(2-naphthoyl)ingenol ( 23 ), which exhibited the most potent anti-HIV-1 activity. Compound 23 also acted as an HIV-1-latency-reversing agent on activation of HIV-1 replication in a latently infected U1 cell model and a T cell latent HIV-1 model JLat-A2. Euphorbia kansui showed potent anti-HIV-1 activity during screening of a library composed of plant extracts from Euphorbiaceae and Thymelaeaceae families. Bioassay-guided isolation led to identification of ingenane esters as the active compounds. Further chemical modification resulted in 3-(2-naphthoyl)ingenol (23), which exhibited the most potent anti-HIV-1 activity. Compound 23 also acted as an HIV-1-latency-reversing agent on activation of HIV-1 replication in a latently infected U1 cell model and a T cell latent HIV-1 model JLat-A2. Euphorbia kansui showed potent anti-HIV-1 activity during screening of a library composed of plant extracts from Euphorbiaceae and Thymelaeaceae families. Bioassay-guided isolation led to identification of ingenane esters as the active compounds. Further chemical modification resulted in 3-(2-naphthoyl) ingenol (23), which exhibited the most potent anti-HIV-1 activity. Compound 23 also acted as an HIV-1-latency-reversing agent on activation of HIV-1 replication in a latently infected U1 cell model and a T cell latent HIV-1 model JLat-A2. (C) 2018 Elsevier Masson SAS. All rights reserved.
Author	Liu, Qingbo Chen, Chin-Ho Huang, Li Asada, Yoshihisa Lee, Kuo-Hsiung Morris-Natschke, Susan L. Li, Wei Koike, Kazuo
AuthorAffiliation	c Surgical Science, Department of Surgery, Duke University Medical Center, Durham, North Carolina 27710, United States a Faculty of Pharmaceutical Sciences, Toho University, Miyama 2-2-1, Funabashi, Chiba 274-8510, Japan b Key Laboratory of Structure-Based Drug Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China d Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina 27599, United States e Chinese Medicine Research and Development Center, China Medical University and Hospital, Taichung 40402, Taiwan
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Keywords	Euphorbia kansui 3-(2-Naphthoyl)ingenol Anti-HIV Ingenane Latency-reversing agent DITERPENES ACTIVATION ROOTS ANTIRETROVIRAL THERAPY LATENCY EXPRESSION
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Snippet	Euphorbia kansui showed potent anti-HIV-1 activity during screening of a library composed of plant extracts from Euphorbiaceae and Thymelaeaceae families.... Euphorbia kansui showed potent anti-HIV-1 activity during screening of a library composed of plant extracts from Euphorbiaceae and Thymelaeaceae families....
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SubjectTerms	3-(2-Naphthoyl)ingenol Anti-HIV Antiviral Agents - chemistry Antiviral Agents - isolation & purification Antiviral Agents - pharmacology Cell Line Chemistry, Medicinal Diterpenes - chemistry Diterpenes - isolation & purification Diterpenes - pharmacology Esters - chemistry Esters - isolation & purification Esters - pharmacology Euphorbia - chemistry Euphorbia kansui HIV Infections - drug therapy HIV-1 - drug effects HIV-1 - physiology Humans Ingenane Latency-reversing agent Life Sciences & Biomedicine Pharmacology & Pharmacy Plant Extracts - chemistry Plant Extracts - isolation & purification Plant Extracts - pharmacology Science & Technology Virus Replication - drug effects
Title	Identification, structural modification, and dichotomous effects on human immunodeficiency virus type 1 (HIV-1) replication of ingenane esters from Euphorbia kansui
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