Antimicrobial alkaloids from Zanthoxylum tetraspermum and caudatum

Nissanka, Ajith P. K.; Karunaratne, Veranja; Bandara, B. M. Ratnayake; Kumar, Vijaya; Nakanishi, Teruyuki; Nishi, Masatoshi; Inada, Akira; Tillekeratne, L. M. V.; Wijesundara, D. S. A.; Gunatilaka, A. A. Leslie

doi:10.1016/s0031-9422(00)00402-7

Cited by 92 publications

(63 citation statements)

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“…[16][17][18] Compound 1 presented a positive test with Dragendorff´s reagent, indicating it to be an alkaloid. The IR spectrum presented bands at 3396 (ν OH ), 1708 (ν C=O ) , 1615, 1516 cm -1 attributed to aromatic rings.…”

Section: Resultsmentioning

confidence: 99%

“…The 1 H NMR spectrum of 1, exhibited signals corresponding to six aromatic hydrogen, characteristic of a benzophenanthridine system. 18 Accordingly, the aromatic region from compound (1) The absence of the methoxyl group in C-7 moves away the effect of the oxygen atom in C-6, justifying its largest chemical shift (d C 60.2) in compound 3, when compared with the correspondent d C 54.8, attributed to C-6 in compound 1; thus revealing ∆ C = 54.9-60.2 = -5.3 ppm as γ effect. Therefore, the structure of 1 was established as 6-acetonyl-N-methyldihydrodecarine, a decarine derivative.…”

Section: Resultsmentioning

confidence: 99%

“…Therefore, the structure of 1 was established as 6-acetonyl-N-methyldihydrodecarine, a decarine derivative. 18 Previous publications, 17,18 however, reported the isolation of the unstable parent alkaloids avicine and nitidine. Although acetone derivatives of avicine and nitidine have been reported in the literature, 19-21 as well as acetone aducts of two other benzophenantridine alkaloids, 22,23 it is controversial, however, whether those acetone derivatives are really present on the plant extract or were isolated as artifacts, due to the greater stability of the acetone aducts as compared to the parent alkaloids avicine and nitidine.…”

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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: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

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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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“…rigidum (Rutaceae) at a 20% concentration presented with an efficiency average of 99%. The Rutaceae family has been extensively studied with respect to the significant number of different secondary metabolites and its biological activities -antibacterial, fungicidal (NISSANKA et al, 2001) and acaricidal (ELANGO; RAHUMAN, 2011). The Zanthoxylum genus includes species with anti-fungicidal and repellent activity against Aedes aegypti (CHOOCHOTE et al, 2007).…”

Section: Discussionmentioning

confidence: 99%

Efficacy of extracts from plants of the Brazilian Pantanal against Rhipicephalus (Boophilus)microplus

Santos

Souza²,

Papassoni³

et al. 2013

Rev. Bras. Parasitol. Vet.

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This research evaluated the in vitro acaricidal activity of extracts from 21 plant species from the Pantanal of Mato Grosso do Sul. During stage I, a larval immersion test was performed using three extract concentrations (5%, 20%, and 40%). During stage II, we used only plants that showed over 95% efficiency at the 40% concentration in stage I in an amount sufficient for the adult immersion test. Aeschynomene denticulata, Angelonia hirta, Aspilia latissima, Caperonia castaneifolia, Centratherum punctatum, Crotalaria micans, Diodia kuntzei, Echinodorus paniculatus, Hyptis mutabilis, Lantana canescens, Melanthera latifolia, Ocotea diospyrifolia, Richardia grandiflora, Sebastiana hispida, Tocoyena formosa, Zanthoxylum rigidum, and Sesbania virgata (fruit extract) showed acaricidal activity against the larval stage of Rhipicephalus (Boophilus) microplus higher than 95% at a 40% (w/v) concentration, while Hippocratea volubilis and Randia armata showed moderate efficacy and Croton glandulosus and Senna obtusifolia had no effect. The M. latifolia, A. hirta, R. grandiflora, and A. latissima raw extracts were evaluated for their activity against adults, and only A. hirta showed an efficacy close to 90%. Eighteen extracts had an efficacy of up to 95% against larvae at a 40% concentration, seven extracts were effective at 20%, and only one (Sebastiana hispida) was effective at a 5% concentration.Keywords: Cattle tick, natural compounds, phytotherapy, parasites. ResumoEste trabalho avaliou a atividade acaricida in vitro de extratos de 21 espécies de plantas do Pantanal de Mato Grosso do Sul. Na etapa I, foi realizado um teste de imersão larval utilizando três concentrações de extrato (5%, 20% e 40%). Na etapa II, utilizou-se apenas as plantas que apresentaram eficácia superior a 95%, na concentração de 40% na etapa I e que apresentasse quantidade suficiente para o teste de imersão de adulto. Aeschynomene denticulata, Angelonia hirta, Aspilia latissima, Caperonia castaneifolia, Centratherum punctatum, Crotalaria micans, Diodia kuntzei, Echinodorus paniculatus, Hyptis mutabilis, Lantana canescens, Melanthera latifolia, Ocotea diospyrifolia, Richardia grandiflora, Sebastiana hispida, Tocoyena formosa, Zanthoxylum rigidum e Sesbania virgata (extrato do fruto) apresentaram atividade acaricida sobre larvas de Rhipicephalus (Boophilus) microplus superior a 95% na concentração de 40% (w/v), enquanto Hippocratea volubilis e Randia armata apresentaram eficácia moderada e Croton glandulosus e Senna obtusifolia não apresentaram efeito acaricida. Os extratos brutos de M. latifolia, A. hirta, R. grandiflora e A. latissima foram avaliados sobre adultos e A. hirta apresentou eficácia próxima de 90%. Dezoito extratos apresentaram eficácia de até 95%, contra larvas, na concentração de 40%, sete extratos foram eficazes a 20% e apenas um (Sebastiana hispida) foi eficaz na concentração de 5%.Palavras-chave: Carrapato bovino, compostos naturais, fitoterapia, parasitas.

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“…The main constituent, nitidine, exhibits an antineoplastic, reverse transcriptase inhibitor effect (Zhou et al, 2003). As a derivative of nitidine, 8-acetonyldihydronitidine, (I), showed significant antibacterial and antifungal activity (Nissanka et al, 2001). Our additional investigations of Z. nitidum led to the isolation of (I).…”

Section: Commentmentioning

confidence: 99%