Antileishmanial activity and cytotoxicity of ent-beyerene diterpenoids

[Display omitted] We describe the in vitro activity of two natural isomeric ent-beyerene diterpenes, several derivatives and synthetic intermediates. Beyerenols 1 and 2 showed EC50 of 4.6 ± 9.4 and 5.3 ± 9.4 μg/mL against amastigotes of L. (V) brazilensis, with SI of 5.1 and 7.7, respectively. Beyer...

Full description

Saved in:
Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2019-01, Vol.27 (1), p.153-160
Main Authors: Murillo, Jilmar A., Gil, Juan F., Upegui, Yulieth A., Restrepo, Adriana M., Robledo, Sara M., Quiñones, Winston, Echeverri, Fernando, San Martin, Aurelio, Olivo, Horacio F., Escobar, Gustavo
Format: Article
Language:English
Subjects:
Antileishmanial
ent-Beyerene diterpenoids
Leishmania brazilensis
Semisynthesis
Steviol
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-c401t-e4edc2b1e857aa06218f542e9067a1b63af62ef1600dc093408fdea56d2636953
cites cdi_FETCH-LOGICAL-c401t-e4edc2b1e857aa06218f542e9067a1b63af62ef1600dc093408fdea56d2636953
container_end_page 160
container_issue 1
container_start_page 153
container_title Bioorganic & medicinal chemistry
container_volume 27
creator Murillo, Jilmar A.
Gil, Juan F.
Upegui, Yulieth A.
Restrepo, Adriana M.
Robledo, Sara M.
Quiñones, Winston
Echeverri, Fernando
San Martin, Aurelio
Olivo, Horacio F.
Escobar, Gustavo
description [Display omitted] We describe the in vitro activity of two natural isomeric ent-beyerene diterpenes, several derivatives and synthetic intermediates. Beyerenols 1 and 2 showed EC50 of 4.6 ± 9.4 and 5.3 ± 9.4 μg/mL against amastigotes of L. (V) brazilensis, with SI of 5.1 and 7.7, respectively. Beyerenol 1 was synthesized from stevioside. In vivo experiments with bereyenols showed cure in 50% of hamsters infected with L. (V) brazilensis topically applied as Cream I (beyerenol 1, 0.81%, w/w) and Cream III (beyerenol 2, 1.96%, w/w). These results suggest that beyerenols are potential candidates for cutaneous leishmaniasis chemotherapy by topical application. In vitro assays of amastigotes of L. (V) brazilensis showed EC50 of 1.1 ± 0.1 and 1.3 ± 0.04 μg/mL, with SI of 3.1 and 3.5 for hydrazone intermediates 10 and 11, respectively.
doi_str_mv 10.1016/j.bmc.2018.11.030
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2138645876</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0968089618316158</els_id><sourcerecordid>2138645876</sourcerecordid><originalsourceid>FETCH-LOGICAL-c401t-e4edc2b1e857aa06218f542e9067a1b63af62ef1600dc093408fdea56d2636953</originalsourceid><addsrcrecordid>eNp9kE1rGzEURUVJaBy3P6CbMMtsZvqepJE1dGVMnRQM3TRroZHeUJn5cCQ51P--Y-x2mdWDy7kX3mHsC0KFgOrrvmoHV3FAXSFWIOADW6BUshSiwRu2gEbpEnSj7th9SnsA4LLBj-xOgNS8lmrBtusxh55C-j3YMdi-sC6Ht5BPhR194U55ytOf4M7B1BU05rKlE0UaqfAhUzzQOAWfPrHbzvaJPl_vkr1sv__aPJe7n08_Nutd6SRgLkmSd7xF0vXKWlAcdVdLTg2olcVWCdspTh0qAO-gERJ058nWynMlVFOLJXu87B7i9HqklM0QkqO-tyNNx2Q4Cq1krVdqRvGCujilFKkzhxgGG08GwZz1mb2Z9ZmzPoNoZn1z5-E6f2wH8v8b_3zNwLcLQPOTb4GiSS7Q6MiHSC4bP4V35v8C1p6AVQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2138645876</pqid></control><display><type>article</type><title>Antileishmanial activity and cytotoxicity of ent-beyerene diterpenoids</title><source>ScienceDirect Journals</source><creator>Murillo, Jilmar A. ; Gil, Juan F. ; Upegui, Yulieth A. ; Restrepo, Adriana M. ; Robledo, Sara M. ; Quiñones, Winston ; Echeverri, Fernando ; San Martin, Aurelio ; Olivo, Horacio F. ; Escobar, Gustavo</creator><creatorcontrib>Murillo, Jilmar A. ; Gil, Juan F. ; Upegui, Yulieth A. ; Restrepo, Adriana M. ; Robledo, Sara M. ; Quiñones, Winston ; Echeverri, Fernando ; San Martin, Aurelio ; Olivo, Horacio F. ; Escobar, Gustavo</creatorcontrib><description>[Display omitted] We describe the in vitro activity of two natural isomeric ent-beyerene diterpenes, several derivatives and synthetic intermediates. Beyerenols 1 and 2 showed EC50 of 4.6 ± 9.4 and 5.3 ± 9.4 μg/mL against amastigotes of L. (V) brazilensis, with SI of 5.1 and 7.7, respectively. Beyerenol 1 was synthesized from stevioside. In vivo experiments with bereyenols showed cure in 50% of hamsters infected with L. (V) brazilensis topically applied as Cream I (beyerenol 1, 0.81%, w/w) and Cream III (beyerenol 2, 1.96%, w/w). These results suggest that beyerenols are potential candidates for cutaneous leishmaniasis chemotherapy by topical application. In vitro assays of amastigotes of L. (V) brazilensis showed EC50 of 1.1 ± 0.1 and 1.3 ± 0.04 μg/mL, with SI of 3.1 and 3.5 for hydrazone intermediates 10 and 11, respectively.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2018.11.030</identifier><identifier>PMID: 30482546</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Antileishmanial ; ent-Beyerene diterpenoids ; Leishmania brazilensis ; Semisynthesis ; Steviol</subject><ispartof>Bioorganic &amp; medicinal chemistry, 2019-01, Vol.27 (1), p.153-160</ispartof><rights>2018</rights><rights>Copyright © 2018. Published by Elsevier Ltd.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c401t-e4edc2b1e857aa06218f542e9067a1b63af62ef1600dc093408fdea56d2636953</citedby><cites>FETCH-LOGICAL-c401t-e4edc2b1e857aa06218f542e9067a1b63af62ef1600dc093408fdea56d2636953</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30482546$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Murillo, Jilmar A.</creatorcontrib><creatorcontrib>Gil, Juan F.</creatorcontrib><creatorcontrib>Upegui, Yulieth A.</creatorcontrib><creatorcontrib>Restrepo, Adriana M.</creatorcontrib><creatorcontrib>Robledo, Sara M.</creatorcontrib><creatorcontrib>Quiñones, Winston</creatorcontrib><creatorcontrib>Echeverri, Fernando</creatorcontrib><creatorcontrib>San Martin, Aurelio</creatorcontrib><creatorcontrib>Olivo, Horacio F.</creatorcontrib><creatorcontrib>Escobar, Gustavo</creatorcontrib><title>Antileishmanial activity and cytotoxicity of ent-beyerene diterpenoids</title><title>Bioorganic &amp; medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>[Display omitted] We describe the in vitro activity of two natural isomeric ent-beyerene diterpenes, several derivatives and synthetic intermediates. Beyerenols 1 and 2 showed EC50 of 4.6 ± 9.4 and 5.3 ± 9.4 μg/mL against amastigotes of L. (V) brazilensis, with SI of 5.1 and 7.7, respectively. Beyerenol 1 was synthesized from stevioside. In vivo experiments with bereyenols showed cure in 50% of hamsters infected with L. (V) brazilensis topically applied as Cream I (beyerenol 1, 0.81%, w/w) and Cream III (beyerenol 2, 1.96%, w/w). These results suggest that beyerenols are potential candidates for cutaneous leishmaniasis chemotherapy by topical application. In vitro assays of amastigotes of L. (V) brazilensis showed EC50 of 1.1 ± 0.1 and 1.3 ± 0.04 μg/mL, with SI of 3.1 and 3.5 for hydrazone intermediates 10 and 11, respectively.</description><subject>Antileishmanial</subject><subject>ent-Beyerene diterpenoids</subject><subject>Leishmania brazilensis</subject><subject>Semisynthesis</subject><subject>Steviol</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp9kE1rGzEURUVJaBy3P6CbMMtsZvqepJE1dGVMnRQM3TRroZHeUJn5cCQ51P--Y-x2mdWDy7kX3mHsC0KFgOrrvmoHV3FAXSFWIOADW6BUshSiwRu2gEbpEnSj7th9SnsA4LLBj-xOgNS8lmrBtusxh55C-j3YMdi-sC6Ht5BPhR194U55ytOf4M7B1BU05rKlE0UaqfAhUzzQOAWfPrHbzvaJPl_vkr1sv__aPJe7n08_Nutd6SRgLkmSd7xF0vXKWlAcdVdLTg2olcVWCdspTh0qAO-gERJ058nWynMlVFOLJXu87B7i9HqklM0QkqO-tyNNx2Q4Cq1krVdqRvGCujilFKkzhxgGG08GwZz1mb2Z9ZmzPoNoZn1z5-E6f2wH8v8b_3zNwLcLQPOTb4GiSS7Q6MiHSC4bP4V35v8C1p6AVQ</recordid><startdate>20190101</startdate><enddate>20190101</enddate><creator>Murillo, Jilmar A.</creator><creator>Gil, Juan F.</creator><creator>Upegui, Yulieth A.</creator><creator>Restrepo, Adriana M.</creator><creator>Robledo, Sara M.</creator><creator>Quiñones, Winston</creator><creator>Echeverri, Fernando</creator><creator>San Martin, Aurelio</creator><creator>Olivo, Horacio F.</creator><creator>Escobar, Gustavo</creator><general>Elsevier Ltd</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20190101</creationdate><title>Antileishmanial activity and cytotoxicity of ent-beyerene diterpenoids</title><author>Murillo, Jilmar A. ; Gil, Juan F. ; Upegui, Yulieth A. ; Restrepo, Adriana M. ; Robledo, Sara M. ; Quiñones, Winston ; Echeverri, Fernando ; San Martin, Aurelio ; Olivo, Horacio F. ; Escobar, Gustavo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c401t-e4edc2b1e857aa06218f542e9067a1b63af62ef1600dc093408fdea56d2636953</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Antileishmanial</topic><topic>ent-Beyerene diterpenoids</topic><topic>Leishmania brazilensis</topic><topic>Semisynthesis</topic><topic>Steviol</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Murillo, Jilmar A.</creatorcontrib><creatorcontrib>Gil, Juan F.</creatorcontrib><creatorcontrib>Upegui, Yulieth A.</creatorcontrib><creatorcontrib>Restrepo, Adriana M.</creatorcontrib><creatorcontrib>Robledo, Sara M.</creatorcontrib><creatorcontrib>Quiñones, Winston</creatorcontrib><creatorcontrib>Echeverri, Fernando</creatorcontrib><creatorcontrib>San Martin, Aurelio</creatorcontrib><creatorcontrib>Olivo, Horacio F.</creatorcontrib><creatorcontrib>Escobar, Gustavo</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic &amp; medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Murillo, Jilmar A.</au><au>Gil, Juan F.</au><au>Upegui, Yulieth A.</au><au>Restrepo, Adriana M.</au><au>Robledo, Sara M.</au><au>Quiñones, Winston</au><au>Echeverri, Fernando</au><au>San Martin, Aurelio</au><au>Olivo, Horacio F.</au><au>Escobar, Gustavo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antileishmanial activity and cytotoxicity of ent-beyerene diterpenoids</atitle><jtitle>Bioorganic &amp; medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2019-01-01</date><risdate>2019</risdate><volume>27</volume><issue>1</issue><spage>153</spage><epage>160</epage><pages>153-160</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>[Display omitted] We describe the in vitro activity of two natural isomeric ent-beyerene diterpenes, several derivatives and synthetic intermediates. Beyerenols 1 and 2 showed EC50 of 4.6 ± 9.4 and 5.3 ± 9.4 μg/mL against amastigotes of L. (V) brazilensis, with SI of 5.1 and 7.7, respectively. Beyerenol 1 was synthesized from stevioside. In vivo experiments with bereyenols showed cure in 50% of hamsters infected with L. (V) brazilensis topically applied as Cream I (beyerenol 1, 0.81%, w/w) and Cream III (beyerenol 2, 1.96%, w/w). These results suggest that beyerenols are potential candidates for cutaneous leishmaniasis chemotherapy by topical application. In vitro assays of amastigotes of L. (V) brazilensis showed EC50 of 1.1 ± 0.1 and 1.3 ± 0.04 μg/mL, with SI of 3.1 and 3.5 for hydrazone intermediates 10 and 11, respectively.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>30482546</pmid><doi>10.1016/j.bmc.2018.11.030</doi><tpages>8</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0968-0896
ispartof Bioorganic & medicinal chemistry, 2019-01, Vol.27 (1), p.153-160
issn 0968-0896
1464-3391
language eng
recordid cdi_proquest_miscellaneous_2138645876
source ScienceDirect Journals
subjects Antileishmanial
ent-Beyerene diterpenoids
Leishmania brazilensis
Semisynthesis
Steviol
title Antileishmanial activity and cytotoxicity of ent-beyerene diterpenoids
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-30T21%3A53%3A19IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Antileishmanial%20activity%20and%20cytotoxicity%20of%20ent-beyerene%20diterpenoids&rft.jtitle=Bioorganic%20&%20medicinal%20chemistry&rft.au=Murillo,%20Jilmar%20A.&rft.date=2019-01-01&rft.volume=27&rft.issue=1&rft.spage=153&rft.epage=160&rft.pages=153-160&rft.issn=0968-0896&rft.eissn=1464-3391&rft_id=info:doi/10.1016/j.bmc.2018.11.030&rft_dat=%3Cproquest_cross%3E2138645876%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c401t-e4edc2b1e857aa06218f542e9067a1b63af62ef1600dc093408fdea56d2636953%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2138645876&rft_id=info:pmid/30482546&rfr_iscdi=true