Unusual Chromenes from Peperomia blanda
TL;DR: In this paper, the methanol extract of the aerial parts of Peperomia blanda (Piperaceae), two chromenes were isolated and characterized mainly through application of 2D-NMR spectroscopy.
Abstract: From the methanol extract of the aerial parts of Peperomia blanda (Piperaceae), two chromenes were isolated and characterized mainly through application of 2D-NMR spectroscopy. The structures were 2S-(4-methyl-3-pentenyl)-6-formyl-8-hydroxy-2,7-dimethyl-2H-chromene and 2S-(4-methyl-3-pentenyl)-5-hydroxy-6-formyl-2,7-dimethyl-2H-chromene named as blandachromenes I and II, respectively.
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TL;DR: The essential oil from P. claussenianum fresh leaves, which was rich in (E)-nerolidol, showed effective growth inhibition of L. amazonensis due to the high percentage of this metabolite in the mixture.
Abstract: Analyses of essential oils obtained from fresh and dried leaves and inflorescences of Piper clausenianum were performed using GC-FID, GC-MS and NMR techniques. Forty compounds were detected for these four oils with the total of identified constituents ranging from 88.7% for the dried inflorescences to 97.7% for the dried leaves. Sesquiterpenes were the main constituents in the volatile fraction from leaves with a high percentage of (E)-nerolidol (up to 83%). However, monoterpenes were identified in greater amount in the inflorescences, with linalool percentages from 50% up. The essential oils from fresh leaves and inflorescences were submitted to anti-parasitic activity against a strain of Leishmania amazonensis. Both samples showed biological activity, but the essential oil from P. claussenianum fresh leaves, which was rich in (E)-nerolidol, showed effective growth inhibition of L. amazonensis due to the high percentage of this metabolite in the mixture.
42 citations
TL;DR: 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: 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 CH2Cl2 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 CH2Cl2 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 IC50 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 IC50 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.
37 citations
TL;DR: The bioactivities of several compounds indicated their potential as antiparasites, antimicrobial, antiviral, cytotoxic agents against several tumoral strains and also as herbicides.
Abstract: The Peperomia is one of the giant genus among Angiosperms with approximately 1600 species spread in the tropics. Their species are valuable as ornamental and several medicinal uses were described but their phytochemistry is poorly investigated compared to Piper (2000 species). In spite of this scarcity, typical classes of secondary metabolites isolated from their species are characterized as polyketides, meroterpenes, chromenes, phenylpropanoids, lignans and amides, among which 2-acylcyclohexane-1,3-diones, orsellinic acid-based meroterpenes and secolignans (peperomins) are very specific to Peperomia. The bioactivities of several compounds indicated their potential as antiparasites, antimicrobial, antiviral, cytotoxic agents against several tumoral strains and also as herbicides.
23 citations
TL;DR: A secolignan, (−)-2-methyl-3-[bis(3′,4′-methylenedioxy-5′-methoxyphenyl) methyl]butyrolactone (1), with a rare cis configuration was isolated from the aerial parts of Peperomia blanda (Piperaceae).
17 citations
Cites background from "Unusual Chromenes from Peperomia bl..."
...blanda showed the presence of two chromenes (Velozo et al., 2006), two C-glycosylflavones with antioxidant activity (Velozo et al....
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...Chemical studies of the aerial parts of P. blanda showed the presence of two chromenes (Velozo et al., 2006), two C-glycosylflavones with antioxidant activity (Velozo et al., 2009), and five tetrahydrofuran lignans with trypanocidal activity (Felippe et al., 2008)....
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TL;DR: A novel chromene, (S)-2-methyl-2-(4-methylpent-3-enyl)-6-(propan-2-ylidene)-3,4,6,7-tetrahydropyrano[4,3-g]chromen-9(2H)-one (1), was isolated from the leaves of Peperomia pellucida (Piperaceae) as mentioned in this paper.
Abstract: A novel chromene, (S)-2-methyl-2-(4-methylpent-3-enyl)-6-(propan-2-ylidene)-3,4,6,7-tetrahydropyrano[4,3-g]chromen-9(2H)-one (1), was isolated from the leaves of Peperomia pellucida (Piperaceae). The chemical structure of 1 was determined by spectroscopic methods and comparison with those related compounds previously reported.
15 citations
Cites background from "Unusual Chromenes from Peperomia bl..."
...1° to blandachromene I [19] and lhotzchromene [20], therefore the S-configuration at C-2 was suggested....
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TL;DR: From the methanol extract of the aerial parts of Peperomia blanda (Piperaceae), two chromenes were isolated and characterized mainly through application of 2D-NMR spectroscopy.
25 citations