Structural Crystalline Characterization of Sakuranetin — An Antimicrobial Flavanone from Twigs of Baccharis retusa (Asteraceae)
Open Access
- 6 June 2014
- Vol. 19 (6), 7528-7542
- https://doi.org/10.3390/molecules19067528
Abstract
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.Funding Information
- FAPESP (2011/51739-0, 2006/57626-5)
This publication has 29 references indexed in Scilit:
- Flavonone treatment reverses airway inflammation and remodelling in an asthma murine modelBritish Journal of Pharmacology, 2012
- Phenolic derivatives from Baccharis retusa DC. (Asteraceae)Biochemical Systematics and Ecology, 2012
- In vitro antileishmanial and antitrypanosomal activities of flavanones from Baccharis retusa DC. (Asteraceae)Experimental Parasitology, 2012
- Isolation of an antileishmanial and antitrypanosomal flavanone from the leaves of Baccharis retusa DC. (Asteraceae)Zeitschrift für Parasitenkunde, 2010
- In vitro antileishmanial, antiplasmodial and cytotoxic activities of phenolics and triterpenoids from Baccharis dracunculifolia D. C. (Asteraceae)Fitoterapia, 2009
- Gênero Baccharis (Asteraceae): aspectos químicos, econômicos e biológicosQuímica Nova, 2005
- Flavonóides e triterpenos de Baccharis pseudotenuifolia: bioatividade sobre Artemia salinaQuímica Nova, 2003
- Diterpene from Baccharis trimera with a relaxant effect on rat vascular smooth musclePhytochemistry, 2000
- Cytotoxic Constituents of Baccharis gaudichaudianaJournal of Natural Products, 1994
- Flavonoids fromInula viscosaPlanta Medica, 1985