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Molecules 2014, 19(6), 7528-7542; doi:10.3390/molecules19067528

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

Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, 09972-270 Diadema–SP, Brazil
Centro de Ciências Naturais e Humanas, Universidade Federal do ABC, 09090-400 Santo André–SP, Brazil
Instituto de Química, Universidade Federal de Alfenas, 37130-000 Alfenas–MG, Brazil
Escola de Engenharia, Universidade Presbiteriana Mackenzie, 01302-090 São Paulo–SP, Brazil
Author to whom correspondence should be addressed.
Received: 2 May 2014 / Revised: 3 June 2014 / Accepted: 3 June 2014 / Published: 6 June 2014
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Bioactivity-guided fractionation of an antimicrobial active extract from twigs of Baccharis retusa C. DC. (Asteraceae) yielded the flavanone 5,4'-dihydroxy-7-methoxy-flavanone (sakuranetin) as responsible for the detected activity. The structure of the bioactive compound was established on the basis of spectroscopic data analysis, including NMR and MS. Additionally, the structure of a new crystal form of sakuranetin was confirmed by X-ray diffratometry. The minimum inhibitory concentrations (MIC) of isolated compound were determined against pathogenic yeast belonging to the genus Candida (six species), Cryptococcus (two species/four serotypes) and S. cerevisiae BY 4742 (S288c background) and ranged from 0.32 to 0.63 μg/μL. Our results showed that sakuranetin, which structure was fully characterized, could be used as a tool for the design of novel and more efficacious antifungal agents. View Full-Text
Keywords: Baccharis retusa; sakuranetin; X-ray diffratometry; antimicrobial activity Baccharis retusa; sakuranetin; X-ray diffratometry; antimicrobial activity

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MDPI and ACS Style

dos S. Grecco, S.; Dorigueto, A.C.; Landre, I.M.; Soares, M.G.; Martho, K.; Lima, R.; Pascon, R.C.; Vallim, M.A.; Capello, T.M.; Romoff, P.; Sartorelli, P.; Lago, J.H.G. Structural Crystalline Characterization of Sakuranetin — An Antimicrobial Flavanone from Twigs of Baccharis retusa (Asteraceae). Molecules 2014, 19, 7528-7542.

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