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Anti-malarial, anti-trypanosomal, and anti-leishmanial activities of jacaranone isolated from Pentacalia desiderabilis (Vell.) Cuatrec. (Asteraceae)
Leishmaniasis, Chagas disease, and malaria affect the poorest population around the world, with an elevated mortality and morbidity. In addition, the therapeutic alternatives are usually toxic or ineffective drugs especially those against the trypanosomatids. In the course of selection of new anti-p...
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Published in: | Parasitology research (1987) 2012-01, Vol.110 (1), p.95-101 |
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container_title | Parasitology research (1987) |
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creator | Morais, Thiago R. Romoff, Paulete Fávero, Oriana A. Reimão, Juliana Q. Lourenço, Walkyria C. Tempone, André G. Hristov, Angelica D. Di Santi, Silvia M. Lago, João Henrique G. Sartorelli, Patricia Ferreira, Marcelo J. P. |
description | Leishmaniasis, Chagas disease, and malaria affect the poorest population around the world, with an elevated mortality and morbidity. In addition, the therapeutic alternatives are usually toxic or ineffective drugs especially those against the trypanosomatids. In the course of selection of new anti-protozoal compounds from Brazilian flora, the CH
2
C
l2
phase from MeOH extract obtained from the leaves of
Pentacalia desiderabilis
(Vell.) Cuatrec. (Asteraceae) showed in vitro anti-leishmanial, anti-malarial, and anti-trypanosomal activities. The chromatographic fractionation of the CH
2
Cl
2
phase led to the isolation of the bioactive compound, which was characterized as jacaranone [methyl (1-hydroxy-4-oxo-2,5-cyclohexandienyl)acetate], by spectroscopic methods. This compound showed activity against promastigotes of
Leishmania
(L.)
chagasi
,
Leishmania
(V.)
braziliensis
, and
Leishmania
(L.).
amazonensis
showing an IC
50
of 17.22, 12.93, and 11.86 μg/mL, respectively. Jacaranone was also tested in vitro against the
Trypanosoma cruzi
trypomastigotes and
Plasmodium falciparum
chloroquine-resistant parasites (K1 strain) showing an IC
50
of 13 and 7.82 μg/mL, respectively, and was 3.5-fold more effective than benznidazole in anti-
Trypanosoma cruzi
assay. However, despite of the potential against promatigotes forms, this compound was not effective against amastigotes of
L.
(L.)
chagasi
and
T. cruzi
. The cytotoxicity study using Kidney Rhesus monkey cells, demonstrated that jacaranone showed selectivity against
P. falciparum
(21.75 μg/mL) and a selectivity index of 3. The obtained results suggested that jacaranone, as other similar secondary metabolites or synthetic analogs, might be useful tolls for drug design for in vivo studies against protozoan diseases. |
doi_str_mv | 10.1007/s00436-011-2454-9 |
format | article |
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2
C
l2
phase from MeOH extract obtained from the leaves of
Pentacalia desiderabilis
(Vell.) Cuatrec. (Asteraceae) showed in vitro anti-leishmanial, anti-malarial, and anti-trypanosomal activities. The chromatographic fractionation of the CH
2
Cl
2
phase led to the isolation of the bioactive compound, which was characterized as jacaranone [methyl (1-hydroxy-4-oxo-2,5-cyclohexandienyl)acetate], by spectroscopic methods. This compound showed activity against promastigotes of
Leishmania
(L.)
chagasi
,
Leishmania
(V.)
braziliensis
, and
Leishmania
(L.).
amazonensis
showing an IC
50
of 17.22, 12.93, and 11.86 μg/mL, respectively. Jacaranone was also tested in vitro against the
Trypanosoma cruzi
trypomastigotes and
Plasmodium falciparum
chloroquine-resistant parasites (K1 strain) showing an IC
50
of 13 and 7.82 μg/mL, respectively, and was 3.5-fold more effective than benznidazole in anti-
Trypanosoma cruzi
assay. However, despite of the potential against promatigotes forms, this compound was not effective against amastigotes of
L.
(L.)
chagasi
and
T. cruzi
. The cytotoxicity study using Kidney Rhesus monkey cells, demonstrated that jacaranone showed selectivity against
P. falciparum
(21.75 μg/mL) and a selectivity index of 3. The obtained results suggested that jacaranone, as other similar secondary metabolites or synthetic analogs, might be useful tolls for drug design for in vivo studies against protozoan diseases.</description><identifier>ISSN: 0932-0113</identifier><identifier>EISSN: 1432-1955</identifier><identifier>DOI: 10.1007/s00436-011-2454-9</identifier><identifier>PMID: 21614544</identifier><identifier>CODEN: PARREZ</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer-Verlag</publisher><subject>Animals ; Antiprotozoal Agents - isolation & purification ; Antiprotozoal Agents - pharmacology ; Antiprotozoal Agents - toxicity ; Asteraceae ; Asteraceae - chemistry ; Benzoquinones - isolation & purification ; Benzoquinones - pharmacology ; Benzoquinones - toxicity ; Biological and medical sciences ; Biomedical and Life Sciences ; Biomedicine ; Brazil ; Cell Line ; Cell Survival - drug effects ; Chromatography ; Fundamental and applied biological sciences. Psychology ; General aspects ; General aspects and techniques. Study of several systematic groups. Models ; Immunology ; Inhibitory Concentration 50 ; Invertebrates ; Leishmania ; Leishmania - drug effects ; Macaca mulatta ; Medical Microbiology ; Microbiology ; Original Paper ; Plant Extracts - isolation & purification ; Plant Extracts - pharmacology ; Plant Extracts - toxicity ; Plant Leaves - chemistry ; Plasmodium falciparum ; Plasmodium falciparum - drug effects ; Spectrum Analysis ; Trypanosoma cruzi ; Trypanosoma cruzi - drug effects</subject><ispartof>Parasitology research (1987), 2012-01, Vol.110 (1), p.95-101</ispartof><rights>Springer-Verlag 2011</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c472t-2d57780e34ae8e15c9884ce21db33d9d346b9b0c133cfad1b1bf9eb8ab6d813b3</citedby><cites>FETCH-LOGICAL-c472t-2d57780e34ae8e15c9884ce21db33d9d346b9b0c133cfad1b1bf9eb8ab6d813b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,786,790,27957,27958</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=25566999$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21614544$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Morais, Thiago R.</creatorcontrib><creatorcontrib>Romoff, Paulete</creatorcontrib><creatorcontrib>Fávero, Oriana A.</creatorcontrib><creatorcontrib>Reimão, Juliana Q.</creatorcontrib><creatorcontrib>Lourenço, Walkyria C.</creatorcontrib><creatorcontrib>Tempone, André G.</creatorcontrib><creatorcontrib>Hristov, Angelica D.</creatorcontrib><creatorcontrib>Di Santi, Silvia M.</creatorcontrib><creatorcontrib>Lago, João Henrique G.</creatorcontrib><creatorcontrib>Sartorelli, Patricia</creatorcontrib><creatorcontrib>Ferreira, Marcelo J. P.</creatorcontrib><title>Anti-malarial, anti-trypanosomal, and anti-leishmanial activities of jacaranone isolated from Pentacalia desiderabilis (Vell.) Cuatrec. (Asteraceae)</title><title>Parasitology research (1987)</title><addtitle>Parasitol Res</addtitle><addtitle>Parasitol Res</addtitle><description>Leishmaniasis, Chagas disease, and malaria affect the poorest population around the world, with an elevated mortality and morbidity. In addition, the therapeutic alternatives are usually toxic or ineffective drugs especially those against the trypanosomatids. In the course of selection of new anti-protozoal compounds from Brazilian flora, the CH
2
C
l2
phase from MeOH extract obtained from the leaves of
Pentacalia desiderabilis
(Vell.) Cuatrec. (Asteraceae) showed in vitro anti-leishmanial, anti-malarial, and anti-trypanosomal activities. The chromatographic fractionation of the CH
2
Cl
2
phase led to the isolation of the bioactive compound, which was characterized as jacaranone [methyl (1-hydroxy-4-oxo-2,5-cyclohexandienyl)acetate], by spectroscopic methods. This compound showed activity against promastigotes of
Leishmania
(L.)
chagasi
,
Leishmania
(V.)
braziliensis
, and
Leishmania
(L.).
amazonensis
showing an IC
50
of 17.22, 12.93, and 11.86 μg/mL, respectively. Jacaranone was also tested in vitro against the
Trypanosoma cruzi
trypomastigotes and
Plasmodium falciparum
chloroquine-resistant parasites (K1 strain) showing an IC
50
of 13 and 7.82 μg/mL, respectively, and was 3.5-fold more effective than benznidazole in anti-
Trypanosoma cruzi
assay. However, despite of the potential against promatigotes forms, this compound was not effective against amastigotes of
L.
(L.)
chagasi
and
T. cruzi
. The cytotoxicity study using Kidney Rhesus monkey cells, demonstrated that jacaranone showed selectivity against
P. falciparum
(21.75 μg/mL) and a selectivity index of 3. The obtained results suggested that jacaranone, as other similar secondary metabolites or synthetic analogs, might be useful tolls for drug design for in vivo studies against protozoan diseases.</description><subject>Animals</subject><subject>Antiprotozoal Agents - isolation & purification</subject><subject>Antiprotozoal Agents - pharmacology</subject><subject>Antiprotozoal Agents - toxicity</subject><subject>Asteraceae</subject><subject>Asteraceae - chemistry</subject><subject>Benzoquinones - isolation & purification</subject><subject>Benzoquinones - pharmacology</subject><subject>Benzoquinones - toxicity</subject><subject>Biological and medical sciences</subject><subject>Biomedical and Life Sciences</subject><subject>Biomedicine</subject><subject>Brazil</subject><subject>Cell Line</subject><subject>Cell Survival - drug effects</subject><subject>Chromatography</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>General aspects</subject><subject>General aspects and techniques. Study of several systematic groups. Models</subject><subject>Immunology</subject><subject>Inhibitory Concentration 50</subject><subject>Invertebrates</subject><subject>Leishmania</subject><subject>Leishmania - drug effects</subject><subject>Macaca mulatta</subject><subject>Medical Microbiology</subject><subject>Microbiology</subject><subject>Original Paper</subject><subject>Plant Extracts - isolation & purification</subject><subject>Plant Extracts - pharmacology</subject><subject>Plant Extracts - toxicity</subject><subject>Plant Leaves - chemistry</subject><subject>Plasmodium falciparum</subject><subject>Plasmodium falciparum - drug effects</subject><subject>Spectrum Analysis</subject><subject>Trypanosoma cruzi</subject><subject>Trypanosoma cruzi - drug effects</subject><issn>0932-0113</issn><issn>1432-1955</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNp9kc2OFCEUhYnROO3oA7gxbEx6EquFgvph2enojMkkulC35AK3lE5V0QJlMu_hA0unWt254eee71zIuYS85GzHGeveJsakaCvGeVXLRlbqEdlwKeqKq6Z5TDZMlXNRxRV5ltKRMd61Uj4lVzVveTHIDfm1n7OvJhghehjfUDhfc3w4wRxSmNaSW8sj-vR9grmAFGz2P332mGgY6BEsxOKYkfoURsjo6BDDRD_hnIs2eqAOk3cYwfjRJ7r9iuO4u6GHBXJEu6PbfcpFtQh485w8GWBM-OKyX5Mv7999PtxV9x9vPxz295WVXZ2r2jVd1zMUErBH3ljV99JizZ0RwiknZGuUYZYLYQdw3HAzKDQ9mNb1XBhxTbZr31MMPxZMWU8-2fIxmDEsSfNGsrpuy1JQvqI2hpQiDvoU_QTxQXOmz8PQ6zB0iVufh6FV8by6tF_MhO6v40_6BXh9ASCVkIYSofXpH9c0bavUuVG9cqlI8zeM-hiWOJdo_vP6b0XPo7I</recordid><startdate>20120101</startdate><enddate>20120101</enddate><creator>Morais, Thiago R.</creator><creator>Romoff, Paulete</creator><creator>Fávero, Oriana A.</creator><creator>Reimão, Juliana Q.</creator><creator>Lourenço, Walkyria C.</creator><creator>Tempone, André G.</creator><creator>Hristov, Angelica D.</creator><creator>Di Santi, Silvia M.</creator><creator>Lago, João Henrique G.</creator><creator>Sartorelli, Patricia</creator><creator>Ferreira, Marcelo J. P.</creator><general>Springer-Verlag</general><general>Springer</general><scope>IQODW</scope><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>C1K</scope><scope>F1W</scope><scope>H95</scope><scope>H97</scope><scope>L.G</scope><scope>M7N</scope></search><sort><creationdate>20120101</creationdate><title>Anti-malarial, anti-trypanosomal, and anti-leishmanial activities of jacaranone isolated from Pentacalia desiderabilis (Vell.) Cuatrec. (Asteraceae)</title><author>Morais, Thiago R. ; Romoff, Paulete ; Fávero, Oriana A. ; Reimão, Juliana Q. ; Lourenço, Walkyria C. ; Tempone, André G. ; Hristov, Angelica D. ; Di Santi, Silvia M. ; Lago, João Henrique G. ; Sartorelli, Patricia ; Ferreira, Marcelo J. P.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c472t-2d57780e34ae8e15c9884ce21db33d9d346b9b0c133cfad1b1bf9eb8ab6d813b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Animals</topic><topic>Antiprotozoal Agents - isolation & purification</topic><topic>Antiprotozoal Agents - pharmacology</topic><topic>Antiprotozoal Agents - toxicity</topic><topic>Asteraceae</topic><topic>Asteraceae - chemistry</topic><topic>Benzoquinones - isolation & purification</topic><topic>Benzoquinones - pharmacology</topic><topic>Benzoquinones - toxicity</topic><topic>Biological and medical sciences</topic><topic>Biomedical and Life Sciences</topic><topic>Biomedicine</topic><topic>Brazil</topic><topic>Cell Line</topic><topic>Cell Survival - drug effects</topic><topic>Chromatography</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>General aspects</topic><topic>General aspects and techniques. Study of several systematic groups. Models</topic><topic>Immunology</topic><topic>Inhibitory Concentration 50</topic><topic>Invertebrates</topic><topic>Leishmania</topic><topic>Leishmania - drug effects</topic><topic>Macaca mulatta</topic><topic>Medical Microbiology</topic><topic>Microbiology</topic><topic>Original Paper</topic><topic>Plant Extracts - isolation & purification</topic><topic>Plant Extracts - pharmacology</topic><topic>Plant Extracts - toxicity</topic><topic>Plant Leaves - chemistry</topic><topic>Plasmodium falciparum</topic><topic>Plasmodium falciparum - drug effects</topic><topic>Spectrum Analysis</topic><topic>Trypanosoma cruzi</topic><topic>Trypanosoma cruzi - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Morais, Thiago R.</creatorcontrib><creatorcontrib>Romoff, Paulete</creatorcontrib><creatorcontrib>Fávero, Oriana A.</creatorcontrib><creatorcontrib>Reimão, Juliana Q.</creatorcontrib><creatorcontrib>Lourenço, Walkyria C.</creatorcontrib><creatorcontrib>Tempone, André G.</creatorcontrib><creatorcontrib>Hristov, Angelica D.</creatorcontrib><creatorcontrib>Di Santi, Silvia M.</creatorcontrib><creatorcontrib>Lago, João Henrique G.</creatorcontrib><creatorcontrib>Sartorelli, Patricia</creatorcontrib><creatorcontrib>Ferreira, Marcelo J. P.</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ASFA: Aquatic Sciences and Fisheries Abstracts</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 1: Biological Sciences & Living Resources</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 3: Aquatic Pollution & Environmental Quality</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) Professional</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><jtitle>Parasitology research (1987)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Morais, Thiago R.</au><au>Romoff, Paulete</au><au>Fávero, Oriana A.</au><au>Reimão, Juliana Q.</au><au>Lourenço, Walkyria C.</au><au>Tempone, André G.</au><au>Hristov, Angelica D.</au><au>Di Santi, Silvia M.</au><au>Lago, João Henrique G.</au><au>Sartorelli, Patricia</au><au>Ferreira, Marcelo J. P.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Anti-malarial, anti-trypanosomal, and anti-leishmanial activities of jacaranone isolated from Pentacalia desiderabilis (Vell.) Cuatrec. (Asteraceae)</atitle><jtitle>Parasitology research (1987)</jtitle><stitle>Parasitol Res</stitle><addtitle>Parasitol Res</addtitle><date>2012-01-01</date><risdate>2012</risdate><volume>110</volume><issue>1</issue><spage>95</spage><epage>101</epage><pages>95-101</pages><issn>0932-0113</issn><eissn>1432-1955</eissn><coden>PARREZ</coden><notes>ObjectType-Article-1</notes><notes>SourceType-Scholarly Journals-1</notes><notes>ObjectType-Feature-2</notes><notes>content type line 23</notes><abstract>Leishmaniasis, Chagas disease, and malaria affect the poorest population around the world, with an elevated mortality and morbidity. In addition, the therapeutic alternatives are usually toxic or ineffective drugs especially those against the trypanosomatids. In the course of selection of new anti-protozoal compounds from Brazilian flora, the CH
2
C
l2
phase from MeOH extract obtained from the leaves of
Pentacalia desiderabilis
(Vell.) Cuatrec. (Asteraceae) showed in vitro anti-leishmanial, anti-malarial, and anti-trypanosomal activities. The chromatographic fractionation of the CH
2
Cl
2
phase led to the isolation of the bioactive compound, which was characterized as jacaranone [methyl (1-hydroxy-4-oxo-2,5-cyclohexandienyl)acetate], by spectroscopic methods. This compound showed activity against promastigotes of
Leishmania
(L.)
chagasi
,
Leishmania
(V.)
braziliensis
, and
Leishmania
(L.).
amazonensis
showing an IC
50
of 17.22, 12.93, and 11.86 μg/mL, respectively. Jacaranone was also tested in vitro against the
Trypanosoma cruzi
trypomastigotes and
Plasmodium falciparum
chloroquine-resistant parasites (K1 strain) showing an IC
50
of 13 and 7.82 μg/mL, respectively, and was 3.5-fold more effective than benznidazole in anti-
Trypanosoma cruzi
assay. However, despite of the potential against promatigotes forms, this compound was not effective against amastigotes of
L.
(L.)
chagasi
and
T. cruzi
. The cytotoxicity study using Kidney Rhesus monkey cells, demonstrated that jacaranone showed selectivity against
P. falciparum
(21.75 μg/mL) and a selectivity index of 3. The obtained results suggested that jacaranone, as other similar secondary metabolites or synthetic analogs, might be useful tolls for drug design for in vivo studies against protozoan diseases.</abstract><cop>Berlin/Heidelberg</cop><pub>Springer-Verlag</pub><pmid>21614544</pmid><doi>10.1007/s00436-011-2454-9</doi><tpages>7</tpages></addata></record> |
fulltext | fulltext |
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ispartof | Parasitology research (1987), 2012-01, Vol.110 (1), p.95-101 |
issn | 0932-0113 1432-1955 |
language | eng |
recordid | cdi_proquest_miscellaneous_1540226402 |
source | Springer Link |
subjects | Animals Antiprotozoal Agents - isolation & purification Antiprotozoal Agents - pharmacology Antiprotozoal Agents - toxicity Asteraceae Asteraceae - chemistry Benzoquinones - isolation & purification Benzoquinones - pharmacology Benzoquinones - toxicity Biological and medical sciences Biomedical and Life Sciences Biomedicine Brazil Cell Line Cell Survival - drug effects Chromatography Fundamental and applied biological sciences. Psychology General aspects General aspects and techniques. Study of several systematic groups. Models Immunology Inhibitory Concentration 50 Invertebrates Leishmania Leishmania - drug effects Macaca mulatta Medical Microbiology Microbiology Original Paper Plant Extracts - isolation & purification Plant Extracts - pharmacology Plant Extracts - toxicity Plant Leaves - chemistry Plasmodium falciparum Plasmodium falciparum - drug effects Spectrum Analysis Trypanosoma cruzi Trypanosoma cruzi - drug effects |
title | Anti-malarial, anti-trypanosomal, and anti-leishmanial activities of jacaranone isolated from Pentacalia desiderabilis (Vell.) Cuatrec. (Asteraceae) |
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