Selective Effect of 2′,6′-Dihydroxy-4′-Methoxychalcone Isolated from Piper aduncum on Leishmania amazonensis

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Published inAntimicrobial Agents and Chemotherapy Vol. 43; no. 5; pp. 1234 - 1241
Main Authors TORRES-SANTOS, E. C, LIMA MOREIRA, D, KAPLAN, M. A. C, MEIRELLES, M. N, ROSSI-BERGMANN, B
Format Journal Article
LanguageEnglish
Published Washington, DC American Society for Microbiology 01.05.1999
Subjects
Animals
Anti-Infective Agents
Anti-Infective Agents - pharmacology
Anti-Infective Agents - therapeutic use
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antiparasitic agents
Antiparasitic Agents - pharmacology
Antiparasitic Agents - therapeutic use
Biological and medical sciences
Cells, Cultured
Chalcone
Chalcone - analogs & derivatives
Chalcone - pharmacology
Chalcone - therapeutic use
Chalcones
Leishmania
Leishmania - drug effects
Leishmania amazonensis
Leishmaniasis, Cutaneous
Leishmaniasis, Cutaneous - drug therapy
Macrophages - drug effects
Macrophages - parasitology
Macrophages - ultrastructure
Mechanisms of Action: Physiological Effects
Medical sciences
Mice
Mice, Inbred BALB C
Microscopy, Electron
Pharmacology. Drug treatments
Piper aduncum
Plant Extracts
Plant Extracts - pharmacology
Plant Extracts - therapeutic use
Plants - metabolism
Kinetoplastida
Protozoa
Toxicity
Inflorescence
Rodentia
Piperaceae
In vitro
Vertebrata
Mammalia
Mouse
Dicotyledones
Animal
Nitric oxide
Leishmania
Angiospermae
Parasiticid
Plant origin
Spermatophyta
Mechanism of action
Piper
Amastigote
Macrophage
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2′,6′-Dihydroxy-4′-methoxychalcone (DMC) was purified from the dichloromethane extract of Piper aduncum inflorescences. DMC showed significant activity in vitro against promastigotes and intracellular amastigotes of Leishmania amazonensis, with 50% effective doses of 0.5 and 24 μg/ml, respectively. Its inhibitory effect on amastigotes is apparently a direct effect on the parasites and is not due to activation of the nitrogen oxidative metabolism of macrophages, since the production of nitric oxide by both unstimulated and recombinant gamma interferon-stimulated macrophages was decreased rather than increased with DMC. The phagocytic activity of macrophages was functioning normally even with DMC concentrations as high as 80 μg/ml, as seen by electron microscopy and by the uptake of fluorescein isothiocyanate-labeled beads. Ultrastructural studies also showed that in the presence of DMC the mitochondria of promastigotes were enlarged and disorganized. Despite destruction of intracellular amastigotes, no disarrangement of macrophage organelles were observed, even at 80 μg of DMC/ml. These observations suggest that DMC is selectively toxic to the parasites. Its simple structure may well enable it to serve as a new lead compound for the synthesis of novel antileishmanial drugs.
2′,6′-Dihydroxy-4′-methoxychalcone (DMC) was purified from the dichloromethane extract of Piper aduncum inflorescences. DMC showed significant activity in vitro against promastigotes and intracellular amastigotes of Leishmania amazonensis , with 50% effective doses of 0.5 and 24 μg/ml, respectively. Its inhibitory effect on amastigotes is apparently a direct effect on the parasites and is not due to activation of the nitrogen oxidative metabolism of macrophages, since the production of nitric oxide by both unstimulated and recombinant gamma interferon-stimulated macrophages was decreased rather than increased with DMC. The phagocytic activity of macrophages was functioning normally even with DMC concentrations as high as 80 μg/ml, as seen by electron microscopy and by the uptake of fluorescein isothiocyanate-labeled beads. Ultrastructural studies also showed that in the presence of DMC the mitochondria of promastigotes were enlarged and disorganized. Despite destruction of intracellular amastigotes, no disarrangement of macrophage organelles were observed, even at 80 μg of DMC/ml. These observations suggest that DMC is selectively toxic to the parasites. Its simple structure may well enable it to serve as a new lead compound for the synthesis of novel antileishmanial drugs.
2',6'-Dihydroxy-4'-methoxychalcone (DMC) was purified from the dichloromethane extract of Piper aduncum inflorescences. DMC showed significant activity in vitro against promastigotes and intracellular amastigotes of Leishmania amazonensis, with 50% effective doses of 0.5 and 24 mu g/ml, respectively. Its inhibitory effect on amastigotes is apparently a direct effect on the parasites and is not due to activation of the nitrogen oxidative metabolism of macrophages, since the production of nitric oxide by both unstimulated and recombinant gamma interferon-stimulated macrophages was decreased rather than increased with DMC. The phagocytic activity of macrophages was functioning normally even with DMC concentrations as high as 80 mu g/ml, as seen by electron microscopy and by the uptake of fluorescein isothiocyanate-labeled beads. Ultra-structural studies also showed that in the presence of DMC the mitochondria of promastigotes were enlarged and disorganized. Despite destruction of intracellular amastigotes, no disarrangement of macrophage organelles were observed, even at 80 mu g of DMC/ml. These observations suggest that DMC is selectively toxic to the parasites. Its simple structure may well enable it to serve as a new lead compound for the synthesis of novel antileishmanial drugs.
2',6'-Dihydroxy-4'-methoxychalcone (DMC) was purified from the dichloromethane extract of Piper aduncum inflorescences. DMC showed significant activity in vitro against promastigotes and intracellular amastigotes of Leishmania amazonensis, with 50% effective doses of 0.5 and 24 micrograms/ml, respectively. Its inhibitory effect on amastigotes is apparently a direct effect on the parasites and is not due to activation of the nitrogen oxidative metabolism of macrophages, since the production of nitric oxide by both unstimulated and recombinant gamma interferon-stimulated macrophages was decreased rather than increased with DMC. The phagocytic activity of macrophages was functioning normally even with DMC concentrations as high as 80 micrograms/ml, as seen by electron microscopy and by the uptake of fluorescein isothiocyanate-labeled beads. Ultrastructural studies also showed that in the presence of DMC the mitochondria of promastigotes were enlarged and disorganized. Despite destruction of intracellular amastigotes, no disarrangement of macrophage organelles were observed, even at 80 micrograms of DMC/ml. These observations suggest that DMC is selectively toxic to the parasites. Its simple structure may well enable it to serve as a new lead compound for the synthesis of novel antileishmanial drugs.
Author Bartira Rossi-Bergmann
Davyson Lima Moreira
Maria Auxiliadora C. Kaplan
Eduardo Caio Torres-Santos
Maria Nazareth Meirelles
AuthorAffiliation Instituto de Biofisica Carlos Chagas Filho 1 and Núcleo de Pesquisa de Produtos Naturais, 2 Universidade Federal do Rio de Janeiro, and Laboratório de Ultraestrutura Celular, Instituto Oswaldo Cruz, FIOCRUZ, 3 Rio de Janeiro, Brazil
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Issue 5
Keywords Kinetoplastida
Protozoa
Toxicity
Inflorescence
Rodentia
Piperaceae
In vitro
Vertebrata
Mammalia
Mouse
Dicotyledones
Animal
Nitric oxide
Leishmania
Angiospermae
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Amastigote
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Corresponding author. Mailing address: Instituto de Biofisica Carlos Chagas Filho, Universidade Federal do Rio de Janeiro, 21.949-900 Rio de Janeiro, RJ, Brazil. Phone: 55 (21) 260 6963. Fax: 55 (21) 2808193. E-mail: bbergman@ibccf.biof.ufrj.br.
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PublicationPlace Washington, DC
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– name: United States
PublicationTitle Antimicrobial Agents and Chemotherapy
PublicationTitleAbbrev Antimicrob. Agents Chemother
PublicationTitleAlternate Antimicrob Agents Chemother
PublicationYear 1999
Publisher American Society for Microbiology
Publisher_xml – name: American Society for Microbiology
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2',6'-Dihydroxy-4'-methoxychalcone (DMC) was purified from the dichloromethane extract of Piper aduncum inflorescences. DMC showed significant activity in...
2′,6′-Dihydroxy-4′-methoxychalcone (DMC) was purified from the dichloromethane extract of Piper aduncum inflorescences. DMC showed significant activity in...
2′,6′-Dihydroxy-4′-methoxychalcone (DMC) was purified from the dichloromethane extract of Piper aduncum inflorescences. DMC showed significant activity in...
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StartPage 1234
SubjectTerms Animals
Anti-Infective Agents
Anti-Infective Agents - pharmacology
Anti-Infective Agents - therapeutic use
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antiparasitic agents
Antiparasitic Agents - pharmacology
Antiparasitic Agents - therapeutic use
Biological and medical sciences
Cells, Cultured
Chalcone
Chalcone - analogs & derivatives
Chalcone - pharmacology
Chalcone - therapeutic use
Chalcones
Leishmania
Leishmania - drug effects
Leishmania amazonensis
Leishmaniasis, Cutaneous
Leishmaniasis, Cutaneous - drug therapy
Macrophages - drug effects
Macrophages - parasitology
Macrophages - ultrastructure
Mechanisms of Action: Physiological Effects
Medical sciences
Mice
Mice, Inbred BALB C
Microscopy, Electron
Pharmacology. Drug treatments
Piper aduncum
Plant Extracts
Plant Extracts - pharmacology
Plant Extracts - therapeutic use
Plants - metabolism
Title Selective Effect of 2′,6′-Dihydroxy-4′-Methoxychalcone Isolated from Piper aduncum on Leishmania amazonensis
URI http://aac.asm.org/content/43/5/1234.abstract
https://www.ncbi.nlm.nih.gov/pubmed/10223942
https://journals.asm.org/doi/10.1128/AAC.43.5.1234
https://search.proquest.com/docview/17252938
https://pubmed.ncbi.nlm.nih.gov/PMC89139
Volume 43
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