Structural Crystalline Characterization of Sakuranetin — An Antimicrobial Flavanone from Twigs of Baccharis retusa (Asteraceae)

Grecco, Simone dos Santos; Dorigueto, Antônio C.; Landre, I. M. R.; Soares, Marisi G.; Martho, Kevin Felipe Cruz; Lima, Ricardo Chaves; Pascon, Renata C.; Vallim, Marcelo A.; Capello, Tabata M.; Romoff, Paulete; Sartorelli, Patrı́cia; Lago, João Henrique G.

doi:10.3390/molecules19067528

Cited by 27 publications

(11 citation statements)

References 30 publications

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“…One-and two-dimensional nuclear magnetic resonance (NMR) spectra were recorded for the isolated compounds using deuterated dimethyl sulfoxide (DMSO-d 6 ). 1 H-and 13 C-NMR chemical shifts (see Supplementary Material) were in accordance with those reported for pinocembrin 1 [28][29][30], sakuranetin 2 [31][32][33][34], cirsimaritin 3 [26,[35][36][37], and naringenin 4 [27,28,[38][39][40][41]. An unambiguous assignment of the 13 C-NMR spectrum of these compounds was deduced from 1 H-1 H COSY, NOESY, HSQC, and HMBC spectra (see Supplementary Material).…”

Section: Column Chromatography Recrystallization Meohsupporting

confidence: 85%

Antiprotozoal Activity Against Entamoeba histolytica of Flavonoids Isolated from Lippia graveolens Kunth

et al. 2020

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Amebiasis caused by Entamoeba histolytica is nowadays a serious public health problem worldwide, especially in developing countries. Annually, up to 100,000 deaths occur across the world. Due to the resistance that pathogenic protozoa exhibit against commercial antiprotozoal drugs, a growing emphasis has been placed on plants used in traditional medicine to discover new antiparasitics. Previously, we reported the in vitro antiamoebic activity of a methanolic extract of Lippia graveolens Kunth (Mexican oregano). In this study, we outline the isolation and structure elucidation of antiamoebic compounds occurring in this plant. The subsequent work-up of this methanol extract by bioguided isolation using several chromatographic techniques yielded the flavonoids pinocembrin (1), sakuranetin (2), cirsimaritin (3), and naringenin (4). Structural elucidation of the isolated compounds was achieved by spectroscopic/spectrometric analyses and comparing literature data. These compounds revealed significant antiprotozoal activity against E. histolytica trophozoites using in vitro tests, showing a 50% inhibitory concentration (IC50) ranging from 28 to 154 µg/mL. Amebicide activity of sakuranetin and cirsimaritin is reported for the first time in this study. These research data may help to corroborate the use of this plant in traditional Mexican medicine for the treatment of dyspepsia.

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Section: Column Chromatography Recrystallization Meohsupporting

confidence: 85%

Antiprotozoal Activity Against Entamoeba histolytica of Flavonoids Isolated from Lippia graveolens Kunth

et al. 2020

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“…as the aglycone of sakuranin [17]. According to the literature, sakuranetin was shown to be the main flavonoid found in the species Baccharis retusa (family Asteraceae), a plant in southern Brazil [18] from which it was isolated and characterized.…”

Section: Sources Of Sakuranetinmentioning

confidence: 99%

“…Grecco et al showed that sakuranetin, which was extracted from twigs of Baccharis retusa, could be employed as a tool for designing novel and more efficient antifungal agents [18]. The minimum inhibitory concentration values (MIC) of the isolated compound were determined for pathogenic yeast belonging to the genus Candida (six species), Cryptococcus (two species/four serotypes) and S. cerevisiae BY 4742 (S288c background).…”

Section: Antimicrobial Activitymentioning

confidence: 99%

A Review on Sources and Pharmacological Aspects of Sakuranetin

Stompor

2020

Nutrients

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Sakuranetin belongs to the group of methoxylated flavanones. It is widely distributed in Polyomnia fruticosa and rice, where it acts as a phytoalexin. Other natural sources of this compound are, among others, grass trees, shrubs, flowering plants, cheery, and some herbal drugs, where it has been found in the form of glycosides (mainly sakuranin). Sakuranetin has antiproliferative activity against human cell lines typical for B16BL6 melanoma, esophageal squamous cell carcinoma (ESCC) and colon cancer (Colo 320). Moreover, sakuranetin shows antiviral activity towards human rhinovirus 3 and influenza B virus and was reported to have antioxidant, antimicrobial, antiinflammatory, antiparasitic, antimutagenic, and antiallergic properties. The aim of this review is to present the current status of knowledge of pro-health properties of sakuranetin.

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“…As part of our continuous research aiming at the discovery of new antimicrobial agents from Brazilian plant species [16,17,18,19,20], in this work we determined the chemical composition of essential oils extracted from three different selected plant species: E. erythropappus (leaves and branches), P. barbatus (leaves), and P. amboinicus (leaves). Additionally, their antimicrobial potential against yeasts and bacteria (including some strains that displayed resistance to antibiotics [21,22] was assessed in broth microdilution assays and the minimum inhibitory concentration (MIC) was thus determined.…”

Section: Introductionmentioning

confidence: 99%

Assessing the Chemical Composition and Antimicrobial Activity of Essential Oils from Brazilian Plants—Eremanthus erythropappus (Asteraceae), Plectrantuns barbatus, and P. amboinicus (Lamiaceae)

et al. 2015

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Abstract:The chemical composition and antimicrobial activity of essential oils obtained from three Brazilian plant species-leaves and branches of Eremanthus erythropappus (Asteraceae), leaves of Plectranthus barbatus, and leaves of P. amboinicus (Lamiaceae)-were determined. Analysis by GC/MS and determination of Kovats indexes both indicated δ-elemene (leaves-42.61% and branches-23.41%) as well as (−)-α-bisabolol (leaves-24.80% and stem bark-66.16%) as major constituents of E. erythropappus essential oils. The main components of leaves of P. barbatus were identified as (Z)-caryophyllene (17.98%), germacrene D (17.35%), and viridiflorol (14.13%); whereas those of leaves of P. amboinicus were characterized as p-cymene (12.01%), γ-terpinene OPEN ACCESSMolecules 2015, 20 8441 (14.74%), carvacrol (37.70%), and (Z)-caryophyllene (14.07%). The antimicrobial activity against yeasts and bacteria was assessed in broth microdilution assays to determine the minimum inhibitory concentration (MIC) necessary to inhibit microbial growth. In addition, the crude oil of branches of E. erythropappus was subjected to chromatographic separation procedures to afford purified (−)-α-bisabolol. This compound displayed biological activity against pathogenic yeasts, thus suggesting that the antimicrobial effect observed with crude oils of E. erythropappus leaves and branches may be related to the occurrence of (−)-α-bisabolol as their main component. Our results showed that crude oils of Brazilian plants, specifically E. erythropappus, P. barbatus, and P. amboinicus and its components, could be used as a tool for the developing novel and more efficacious antimicrobial agents.

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Structural Crystalline Characterization of Sakuranetin — An Antimicrobial Flavanone from Twigs of Baccharis retusa (Asteraceae)

Cited by 27 publications

References 30 publications

Antiprotozoal Activity Against Entamoeba histolytica of Flavonoids Isolated from Lippia graveolens Kunth

Antiprotozoal Activity Against Entamoeba histolytica of Flavonoids Isolated from Lippia graveolens Kunth

A Review on Sources and Pharmacological Aspects of Sakuranetin

Assessing the Chemical Composition and Antimicrobial Activity of Essential Oils from Brazilian Plants—Eremanthus erythropappus (Asteraceae), Plectrantuns barbatus, and P. amboinicus (Lamiaceae)

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