Clerodane Diterpenoids and Acetylenic Lactones from Baccharris Paniculata

Rivera, A. Patricio; Arancibia, Luis; Castillo, M.

doi:10.1021/np50062a045

Cited by 17 publications

(19 citation statements)

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“…The NMR spectra of the isolated compounds 1 and 2 agreed with published data, except for the C-8 and C-9 carbons of compound 1. For this compound, 1 H- 13 C HSQC analysis ( Figure S7, Supplementary Information section) revealed that the carbon at d 21.8 (C-8) was correlated to the hydrogen at d 2.43 (H-8), and that the carbon at d 22.1 (C-9) was correlated to the hydrogen at d 1.62 (H-9), rather than the opposite, as reported by Rivera et al 13 These data are consistent with reports in the literature for the chemical shifts of carbons and hydrogens near triple bonds. 19 For compound 2, the 1 H-13 C HSQC analysis confirmed the attributions available in the literature.…”

Section: Resultsmentioning

confidence: 99%

“…1 H and 13 C nuclear magnetic resonance (NMR) spectra, as well as 1 H- 13 C heteronuclear single quantum coherence (HSQC) spectra, were recorded using either an AVANCE 400 MHz spectrometer or an AVANCE 500 MHz spectrometer (Bruker, Rheinstetten, Germany). The fractions and the purified compounds were analyzed by GC-MS using a 7890A gas chromatograph (Agilent, Santa Clara, CA) coupled to a 5975C inert XL MSD single quadrupole detector operated with 70 eV electron ionization.…”

Section: Instrumentationmentioning

confidence: 99%

“…NMR spectra ( 1 H, 13 C and HSQC) and attributions for compounds 1 and 2, together with the chromatography and NMR operational conditions, are available free of charge at http://jbcs.sbq.org.br as a PDF file.…”

Section: Supplementary Informationmentioning

confidence: 99%

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Conyza canadensis: Green Extraction Method of Bioactive Compounds and Evaluation of Their Antifungal Activity

Porto¹,

Rath²,

Queiroz³

2016

J. Braz. Chem. Soc.

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Synthetic fungicides are a common treatment for post-harvest diseases in fruits, although demand is increasing for alternatives such as biopesticides. The aim of this work was to investigate the presence of naturally occurring antifungal compounds in Brazilian specimens of the weed Conyza canadensis. Two compounds [(4Z)-lachnophyllum lactone and (4Z,8Z)-matricaria lactone] were isolated and their antifungal activities were evaluated against eight postharvest disease fungi. Aspergillus niger, Cladosporium sp., and Penicillium digitatum proved susceptible to the treatment (minimum inhibitory concentrations varying from 32 to 64 µg mL -1 ). These fungi are common postharvest pathogens of fruits and vegetables, causing rots and secreting mycotoxins. A green and sustainable extraction method employing pressurized hot water was developed and optimized (100 °C, 4 × 1 min cycles). Yields of 1.46 and 0.24 mg g -1 were obtained for (4Z)-lachnophyllum lactone and (4Z,8Z)-matricaria lactone, respectively. The extract could be applied directly to fruits and vegetables in postharvest treatments.

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Section: Resultsmentioning

confidence: 99%

Section: Instrumentationmentioning

confidence: 99%

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Conyza canadensis: Green Extraction Method of Bioactive Compounds and Evaluation of Their Antifungal Activity

Porto¹,

Rath²,

Queiroz³

2016

J. Braz. Chem. Soc.

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“…The molecular formula is C 11 13 Bioassays against Lactuca sativa and Agrostis stolonifera. Liquid−liquid partitioning and silica gel column chromatographic fractionation of the DCM extract of the aerial parts guided by La.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Bioassay-Directed Isolation and Identification of Phytotoxic and Fungitoxic Acetylenes from Conyza canadensis

Queiroz

Cantrell

Duke

et al. 2012

J. Agric. Food Chem.

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Conyza canadensis (L.) Cronquist syn. (horseweed) is a problematic and invasive weed with reported allelopathic properties. To identify the phytotoxic constituents of the aerial parts, a systematic bioactivity-guided fractionation of the dichloromethane extract was performed. Three active enyne derivatives, (2Z,8Z)-matricaria acid methyl ester, (4Z,8Z)-matricaria lactone, and (4Z)-lachnophyllum lactone, were identified. The lactones inhibited growth of the monocot Agrostis stolonifera (bentgrass) and the dicot Lactuca sativa (lettuce) at 1 mg mL(-1), while the (2Z,8Z)-matricaria acid methyl ester was less active. In a dose-response screening of the lactones for growth inhibitory activity against Lemna paucicostata , (4Z)-lachnophyllum lactone was the most active with an IC50 of 104 μM, while the (4Z,8Z)-matricaria lactone was less active (IC50 of 220 μM). In a fungal direct bioautography assay, the two lactones at 10 and 100 μg/spot inhibited growth of the plant pathogenic fungi Colletotrichum acutatum , Colletotrichum fragariae , and Colletotrichum gloeosporioides . In a dose-response screening of the lactones against six different plant pathogenic fungi, (4Z,8Z)-matricaria lactone was more active than the commercial fungicide azoxystrobin on Col. acutatum , Col. fragariae , and Col. gloeosporioides at 30 μM and about as active as the commercial fungicide captan against Col. gloeosporioides , while (4Z)-lachnophyllum lactone was less active.

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“…Nos países da América do Sul, a morte de bovinos e ovinos ao se alimentarem com folhas de Baccharis 11-13 levou à avaliação da atividade citotóxica [14][15][16][17][18] destas espécies. Do ponto de vista fitoquímico, apesar de não mais que 15% das espécies terem sido estudadas, quanto à sua composição micromolecular, pode-se observar que o gênero é caracterizado pelo acúmulo de sesquiterpenos, diterpenos, triterpenos e flavonóides [19][20][21][22][23] . No presente trabalho realizamos a investigação fitoquímica de B. pseudotenuifolia, juntamente com a avaliação do efeito citotóxico dos extratos, utilizando ensaios com A. salina 24 .…”

Section: Introductionunclassified

Flavonóides e triterpenos de Baccharis pseudotenuifolia: bioatividade sobre Artemia salina

Moreira¹,

Coutinho²,

Montanher³

et al. 2003

Quím. Nova

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Recebido em 14/3/02; aceito em 5/12/02 FLAVONOIDS AND TRITERPENES FROM Baccharis pseudotenuifolia -BIOACTIVITY ON Artemia salina. The phytochemical investigation of the chloroformic and methanolic extracts of the Baccharis pseudotenuifolia led to the isolation of triterpenes, steroids and flavonoids. From chloroformic extract were isolated oleanolic acid and α-spinasterol while from methanolic extract were isolated the flavonoids: hispidulin, naringenin, 3'-methoxy-luteolin, apigenin, kaempferol, eriodyctiol, aromadendrin, quercetin, 3'-methoxy-quercetin, quercetin-3-O-rhamnoside and quercetin-3-O-glucoside. The structure of these compounds were identified by IR, CG/MS, 1 H and 13 C NMR spectral analysis and comparison with literature. In addition, the extracts were evaluated by means of Brine Shrimp Lethality test and the highier activity was observed in the chloroformic extract.Keywords: Baccharis pseudotenuifolia; Artemia salina; flavonoids. INTRODUÇÃO Plantas do gênero Isolamento dos triterpenos e esteróisO extrato em clorofórmio da espécie B. pseudotenuifolia foi submetido a um pré-fracionamento por filtração em leito de CaCO 3 -Na 2 CO 3 -Celite, utilizando-se como eluentes clorofórmio e metanol. Desta forma obteve-se duas frações: uma fração lipofílica eluída com clorofórmio, constituída essencialmente de ceras e uma fração metanólica. A fração metanólica foi submetida ao fracionamento por cromatografia em coluna de sílica gel, utilizando-se como eluente hexano/acetato de etila em gradiente de polaridade. Com este procedimento obteve-se o isolamento do ácido oleanólico (1) 25 . O fracionamento da fração lipofílica em coluna de sílica, eluída com gradiente hexano/acetato de etila, resultou no isolamento de α-espinasterol (2) 26,27 . Isolamento dos flavonóidesO extrato metanólico de B. pseudotenuifolia foi cromatografado em coluna de sílica gel eluída com mistura hexano/acetato de etila/ metanol no modo gradiente de polaridade. As frações que deram reação positiva com o regente FeCl 3 em cromatografia em camada delgada (ccd) foram reunidas em dois grupos. O grupo de menor polaridade foi recromatografado em coluna de sílica gel (gradiente: hexano-acetato de etila) e as frações contendo flavonóides (ccd-FeCl 3 ) foram submetidas a sucessivas cromatografias em coluna de sílica flash 28 sob pressão e purificações por recristalizações, resultando no isolamento dos flavonóides 3 a 10. O grupo mais polar foi submetido a uma gel filtração em Sephadex LH-20 resultando em duas frações flavonoídicas, segundo ccd-FeCl 3 . A recromatografia destas frações em coluna de sílica eluída com clorofórmio/metanol no modo gradiente de polaridade resultou no isolamento de quercetina 11 e na obtenção da mistura quercetina-3-O-ramnosídeo 12 e quercetina-3-O-glicosídeo 13. Bioensaio com Artemia salinaUtilizou-se a metodologia de Meyer 29 adaptada. Cerca de 10 lar-

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Clerodane Diterpenoids and Acetylenic Lactones from Baccharris Paniculata

Cited by 17 publications

References 4 publications

Conyza canadensis: Green Extraction Method of Bioactive Compounds and Evaluation of Their Antifungal Activity

Conyza canadensis: Green Extraction Method of Bioactive Compounds and Evaluation of Their Antifungal Activity

Bioassay-Directed Isolation and Identification of Phytotoxic and Fungitoxic Acetylenes from Conyza canadensis

Flavonóides e triterpenos de Baccharis pseudotenuifolia: bioatividade sobre Artemia salina

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