Evaluation of the Trypanocidal Activity of Lignans Isolated from the Leaves of Zanthoxylum naranjillo

Bastos, Jairo Kenupp; Albuquerque, Sérgio de; Silva, Márcio Luís Andrade e

doi:10.1055/s-1999-14012

Cited by 107 publications

(115 citation statements)

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“…1 Chemically, this genus is characterized by alkaloids, [2][3][4][5][6][7] cumarins, 5,6,8 lignans, 4,9,10 amides 11,12 and terpenes. 5,6,13,14 Ongoing studies have shown that Zanthoxylum exhibit a range of biological activities such as antichagas, 2 tripanocidal, 9 antiplasmodial, 7 anti-HIV 13 and antiinflammatory, 8,10 as well as antihelmintic. 12 Z. riedelianum is used in folk medicine as a decoction against different types of inflammations, rheumatism and skin stains.…”

Section: Introductionmentioning

confidence: 99%

6-acetonyl-N-methyl-dihydrodecarine, a new alkaloid from Zanthoxylum riedelianum

Fernandes¹,

Vieira²,

Silva³

et al. 2009

J. Braz. Chem. Soc.

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Um novo alcalóide benzofenantridínico, 6-acetonil-N-metil-diidrodecarina foi isolado das raízes de Zanthoxylum riedelianum juntamente com lupeol, 6-acetonildiidroqueleritrina e 6-acetonildiidroavicina. As estruturas dessas substâncias foram estabelecidas com base na análise dos dados espectrométricos de IV, EM e RMN incluindo experimentos 2D.A new benzophenanthridine alkaloid, 6-acetonyl-N-methyl-dihydrodecarine was isolated from Zanthoxylum riedelianum roots together with lupeol, 6-acetonyldihydrochelerythrine and 6-acetonyldihydroavicine. The structures were established from the IR, MS and NMR spectral data, including 2D-NMR experiments. Keywords: Zanthoxylum riedelianum, Rutaceae, benzophenanthridine alkaloids IntroductionThe Zanthoxylum genus (Rutaceae) is composed by more than 200 species and largely distributed around the world. 1 Chemically, this genus is characterized by alkaloids, 2-7 cumarins, 5,6,8 lignans, 4,9,10 amides 11,12 and terpenes. 5,6,13,14 Ongoing studies have shown that Zanthoxylum exhibit a range of biological activities such as antichagas, 2 tripanocidal, 9 antiplasmodial, 7 anti-HIV 13 and antiinflammatory, 8,10 as well as antihelmintic. 12 Z. riedelianum is used in folk medicine as a decoction against different types of inflammations, rheumatism and skin stains. 15 Previous works reported the identification of terpenes from the essential oil 14 and lignans from the leaves and the stem bark. 10 In this work we report the isolation and structural elucidation of a novel benzophenanthridine alkaloid, namely, 6-acetonyl-N-methyl-dihydrodecarine (1), together with two known alkaloids 6-acetonyldihydrochelerythrine (2) and 6-acetonyldihydroavicine (3) from the roots of Z. riedelianum. Experimental General proceduresMelting points were uncorrected. IR spectra were recorded on FTIR-Bomem-MB/100 model spectrophotometer using NaCl film. NMR spectra in CDCl 3 , were recorded on Bruker ARX-400 (400 MHz for 1 H and 100 MHz for 13 C); Bruker AC-200 (200 MHz for 1 H and 50 MHZ for 13 C) and Varian-Mercury 300 (300 MHz for 1 H and 75 MHz for 13 C) spectrometers, using tetramethylsilane (TMS) as internal standard. Electron Ionization Mass Spectra (ESI-MS) was undertaken employing a Quatro LC-Micromass UK model spectrometer. Optical rotations were determined on a Perkin-Elmer 341 polarimeter. CC: silica gel (Merck 70-230 mesh ASTM); TLC: silica gel G 60 and silica gel 60 PF 254 (Merck) were used to analyze the fractions collected from column chromatography (CC) with visualization by UV (254 and 366 nm), Dragendorff´s reagent and exposure to iodine vapor. Plant materialZanthoxylum riedelianum (Engl.) was collected in Rio Manso Highway, km 22, Chapada dos Guimarães, Mato 6-Acetonyl-N-methyl-dihydrodecarine, a New Alkaloid from Zanthoxylum riedelianum J. Braz. Chem. Soc. 380 Grosso State, Brazil. A voucher specimen (No. 24.080) was deposited at Universidade Federal de Mato Grosso Central Herbarium. Extraction and isolationDried roots (3.0 kg) were powdered and extracted with hexane and methanol by mac...

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Section: Introductionmentioning

confidence: 99%

6-acetonyl-N-methyl-dihydrodecarine, a new alkaloid from Zanthoxylum riedelianum

Fernandes¹,

Vieira²,

Silva³

et al. 2009

J. Braz. Chem. Soc.

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“…3 De plantas da família Rutaceae foram isolados alcalóides e lignanas com atividades tripanocidas. 4,5 Além disso, as atividades sobre o T. cruzi ou sobre sua enzima GAPDH (gliceraldeído 3-fosfatodesidrogenase) de vários extratos e algumas substâncias isoladas desta mesma família foram determinadas. [6][7][8] A espécie Conchocarpus heterophyllus (A.…”

Section: Introductionunclassified

Piranoflavonas inéditas e atividades tripanocidas das substâncias isoladas de conchocarpus heterophyllus

Ambrozin¹,

Vieira²,

Fernandes³

et al. 2008

Quím. Nova

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. do Café, s/n, 14040-903 Ribeirão Preto -SP, BrasilRecebido em 18/5/07; aceito em 14/11/07; publicado na web em 19/3/08 NEW PYRANOFLAVONES AND TRYPANOCIDAL ACTIVITY OF COMPOUNDS ISOLATED FROM Conchocarpus heterophyllus. The phytochemical investigation of trypanocidal extracts from leaves and stems of Conchocarpus heterophyllus (A. St.-Hil.) Kallunki & Pirani (Rutaceae) afforded new pyranoflavones along with the known compounds flavone, 7-methoxyflavone, 5-hydroxyflavone, haplotusine, 1-methyl-2-phenyl-4-quinolone alkaloid, β-sitosterol, stigmasterol, and β-sitosteryl benzoate. Their structures were established based on their spectral data. NMR data for the alkaloid haplotusine and the new pyranoflavones are described for the first time herein. These compounds were assayed on the tripomastigote forms of Trypanosoma cruzi. Among them, haplotusine and 1-methyl-2-phenyl-4-quinolone showed moderate values of IC 50 136.9 and 144.9 µM, respectively.

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“…Since compound 17 was inactive, this finding implicated that the crucial structural element for activity of 16 may be due to the pinoresinol moiety rather than the taxifolin unit, consistent with reports on the antiprotozoal activity of lignans. 23,24) Next, we assessed the immunostimulating potential of compounds 1-17. First experiments have focused on the evaluation of 1-17 on the release of nitric oxide (NO), using the Griess assay.…”

Section: Resultsmentioning

confidence: 99%

Proanthocyanidins and Related Compounds: Antileishmanial Activity and Modulatory Effects on Nitric Oxide and Tumor Necrosis Factor-.ALPHA.-Release in the Murine Macrophage-Like Cell Line RAW 264.7.

Kolodziej

Kayser

Kiderlen

et al. 2001

Biological & Pharmaceutical Bulletin

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A series of 17 proanthocyanidins and structurally related compounds was tested for activity against Leishmania donovani amastigotes and promastigotes in vitro. Most of the polyphenols significantly inhibited the intracellular survival of L. donovani amastigotes (EC 50 0.8-10.6 nM) when compared with the antileishmanial drug Pentostam ® (EC 50 10.6 nM), but all were inactive against the extracellular form (EC 50 7.8 to Ͼ86 nM). Noteworthy is that all compounds exhibited only moderate or no cytotoxicity against the murine host cells (EC 50 7.8 to Ͼ56 nM; Ͼ25 m mg/ml). These polyphenols were further evaluated for immunomodulatory effects on macrophage functions, including release of nitric oxide (NO), tumor necrosis factor-a a (TNF) and interferon (IFN)-like properties using several functional assays. The results showed that all compounds induced murine RAW 264.7 cells only moderately to release NO (7-26 m mM) relative to the reference stimulus IFN-g g/LPS (119 m mM). The TNF-inducing potential of the polyphenols producing 50% lysis in murine L929 cells ranged from absent to 138 U/ml at the host cell subtoxic concentration of 50 m mg/ml. The highest TNF-inducing activity was associated with those flavan-3-ols with galloyl groups (98-127 U/ml). For proanthocyanidins, it appeared that an increase in the flavanyl chain length did not enhance the induction of TNF-release (32-86 U/ml and below detection limits for oligomers and polymers, respectively). With interferon-like activities, phylloflavan and a prodelphinidin polymer showed appreciable cytoprotective effects, as reflected by the inhibition of the cytopathic effect of encephalomyocarditis virus on L929 fibroblast cells (38 and 36 U/ml, respectively). All remaining compounds displayed only negligible or moderate protective effects at subtoxic concentrations up to 25 m mg/ml (Ͻ5 to 12 U/ml). These results indicate that proanthocyanidins and related compounds have favorable antileishmanial activity in vitro and might be considered as beneficial immunological response modifiers provided there are no bioavailability problems.

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Evaluation of the Trypanocidal Activity of Lignans Isolated from the Leaves of Zanthoxylum naranjillo

Cited by 107 publications

References 0 publications

6-acetonyl-N-methyl-dihydrodecarine, a new alkaloid from Zanthoxylum riedelianum

6-acetonyl-N-methyl-dihydrodecarine, a new alkaloid from Zanthoxylum riedelianum

Piranoflavonas inéditas e atividades tripanocidas das substâncias isoladas de conchocarpus heterophyllus

Proanthocyanidins and Related Compounds: Antileishmanial Activity and Modulatory Effects on Nitric Oxide and Tumor Necrosis Factor-.ALPHA.-Release in the Murine Macrophage-Like Cell Line RAW 264.7.

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