Antifungals and acetylcholinesterase inhibitors from the stem bark of Croton heliotropiifolius

Queiroz, Marcos Marçal Ferreira; Queiroz, Emerson Ferreira; Zeraik, Maria Luiza; Marti, Guillaume; Favre-Godal, Quentin; Simões-Pires, Cláudia A.; Marcourt, Laurence; Carrupt, Pierre‐Alain; Cuendet, Muriel; Paulo, Marçal Q.; Bolzani, Vanderlan da Silva; Wolfender, Jean‐Luc

doi:10.1016/j.phytol.2014.08.013

Cited by 31 publications

(26 citation statements)

References 28 publications

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“…and N-trans-feruloyl-5-hydroxytryptamine (moschamine) (5), 13 the flavonoids 3-o-methyl kaempferol (6), 14 3-o-methyl quercetin (7), 14 3,7-di-o-methyl quercetin (8) 15 and 3,3'-di-o-methyl quercetin (9), 16 and benzoic acid derivatives 4-hydroxybenzoic acid (10), 4-hydroxyBioactive Indole Alkaloids from Croton echioides J. Braz. Chem.…”

Section: N-trans-4-methoxy-cinnamoyl-5-hydroxytryptamine (4)mentioning

confidence: 99%

“…High-resolution electrospray ionization mass spectrometry (HR-ESIMS) were recorded on a BrukerDaltonics MicroTof (Bruker-Daltonics, Bremen, Germany), and the ESIMS were recorded on a Thermo Scientific Orbitrap LTQ XL spectrometer (Thermo Fisher System, San Jose, CA, USA) performed at University of Münster, Germany. Nuclear magnetic resonance (NMR) spectra were recorded on a Varian Mercury Plus 300 MHz spectrometer (7.02 T) (Varian, Palo Alto, CA, USA) operated at 75 MHz for 13 C and 300 MHz for 1 H and 2D NMR, using deuterated MeOH as solvent and tetramethylsilane (TMS) as internal standard. Medium pressure liquid chromatography (MPLC) separation was performed using a Waters 6000A (Waters, Milford, Massachusetts, USA) pump with a manual sample injection valve 10 mL loop coupled with different columns (450 × 10 mm internal diameter (i.d.…”

Section: General Experimental Proceduresmentioning

confidence: 99%

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Bioactive Indole Alkaloids fromCroton echioides

Novello

Marques

Pires

et al. 2016

Journal of the Brazilian Chemical Society

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Bioguided fractionation of a hydroethanolic extract from the stem bark of Croton echioides Baill. led to isolation of the new indole alkaloid N-trans-feruloyl-3,5-dihydroxyindolin-2-one as a stereoisomeric mixture and the known alkaloids N-trans-p-coumaroyl-tryptamine, N-trans-pcoumaroyl-5-hydroxytryptamine, N-trans-4-methoxy-cinnamoyl-5-hydroxytryptamine, N-transferuloyl-5-hydroxytryptamine (moschamine), from the ethyl acetate fraction. The flavonoids 3-o-methyl kaempferol, 3-o-methyl quercetin, 3,7-di-o-methyl quercetin and 3,3'-di-o-methyl quercetin, together with the benzoic acid derivatives 4-hydroxybenzoic acid, 4-hydroxy-3-methoxybenzoic acid and 4-hydroxy-3,5-dimethoxybenzoic acid were also isolated. Alkaloids and the flavonoids showed strong antioxidant properties in vitro radical scavenging assay (2,2-diphenyl-1-picrylhydrazyl, DPPH), with IC 50 values ranging from 9.2 to 17.5 µmol L

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Section: N-trans-4-methoxy-cinnamoyl-5-hydroxytryptamine (4)mentioning

confidence: 99%

Section: General Experimental Proceduresmentioning

confidence: 99%

Bioactive Indole Alkaloids fromCroton echioides

Novello

Marques

Pires

et al. 2016

Journal of the Brazilian Chemical Society

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“…et Zucc. (Tanaka et al 2003), Carthamus tinctorius L. (Sato et al 1985;Roh et al 2004), Croton heliotropiifolius Kunth (Queiroz et al 2014). To the best of our knowledge, Compound (1) in the Centaurea genus had been found in C. nigra and C. montana (Shoeb et al 2006).…”

Section: Chemotaxonomic Significancementioning

confidence: 91%

Lignans and indole alkaloids from the seeds of Centaurea vlachorum Hartvig (Asteraceae), growing wild in Albania and their biological activity

Hodaj

Tsiftsoglou

Abazi

et al. 2016

Natural Product Research

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The present phytochemical investigation of the seeds of Centaurea vlachorum led to the isolation and characterisation of four compounds including two indole alkaloids N-(p-coumaroyl) serotonin (1) and moschamine (2) and two dibenzylbutyrolactone lignans matairesinol (3) and arctiin (4). This is the first report on the isolation of non-volatile secondary metabolites from C. vlachorum. The chemataxonomic significance of these compounds was summarised. Moreover, the isolated compounds were tested for their free radical scavenging activity using the following in vitro assays: (i) interaction with the free stable radical of DPPH (1,1-diphenyl-2-picrylhydrazyl), (ii) inhibition of linoleic acid peroxidation with the dihydrochloric acid of 2,2-Azobis-2-amidinopropane (AAPH). Finally, their inhibitory activity towards soybean lipoxygenase was evaluated, using linoleic acid as substrate.

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“…This genus is rich in chemical constituents with biological activities, among them diterpenoids such as phorbol esters, clerodane, labdane, kaurane, grayanane, tigliane etc. (Liu et al, 2014;Wang et al, 2015;Zhang et al, 2015;Jang et al, 2016;Qiu et al, 2016). Croton species are also rich in active alkaloids (Queiroz et al, Cordeiro et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

Biological screening of extracts from leaf and stem bark of Croton floribundus Spreng. (Euphorbiaceae)

et al. 2018

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This work describes the preliminary evaluation of cytotoxic, antimicrobial, molluscicidal, antioxidant and anticholinesterase activities from leaf (LECF) and stem bark alcoholic extracts (BECF) of the species Croton floribundus Spreng. (Euphorbiaceae), popularly known as capixingui or tapixingui. BECF presented significant toxicity (LC50 = 89.6 μg/ml) in the Artemia salina Leach, 1819 (Crustacea: Branchiopoda) bioassay, whereas LECF did not show activity (LC50 > 1000 μg/ml). From DPPH method, the values of IC50 for the LECF and BECF were 61.2 μg/ml and 62.2 μg/ml, respectively, showing that C. floribundus has an expressive antioxidant activity. Antimicrobial susceptibility was evaluated by microdilution technique and only BECF was active against Staphylococcus aureus (MIC = 39.6 μg/ml). The extracts did not present molluscicidal activity against snail Biomphalaria glabrata Say, 1818 (Gastropoda: Planorbidae). Both extracts revealed the presence of several components with an inhibiting capacity of acetylcholinesterase enzyme on the bioautographic assay. C. floribundus showed to be a promising species considering that it exhibited good biological activity in the most assays performed.

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Antifungals and acetylcholinesterase inhibitors from the stem bark of Croton heliotropiifolius

Cited by 31 publications

References 28 publications

Bioactive Indole Alkaloids fromCroton echioides

Bioactive Indole Alkaloids fromCroton echioides

Lignans and indole alkaloids from the seeds of Centaurea vlachorum Hartvig (Asteraceae), growing wild in Albania and their biological activity

Biological screening of extracts from leaf and stem bark of Croton floribundus Spreng. (Euphorbiaceae)

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