Structural crystalline characterization of sakuranetin--an antimicrobial flavanone from twigs of Baccharis retusa (Asteraceae).

Autor: dos S Grecco S; Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, 09972-270 Diadema-SP, Brazil., Dorigueto AC; Instituto de Química, Universidade Federal de Alfenas, 37130-000 Alfenas-MG, Brazil., Landre IM; Instituto de Química, Universidade Federal de Alfenas, 37130-000 Alfenas-MG, Brazil., Soares MG; Instituto de Química, Universidade Federal de Alfenas, 37130-000 Alfenas-MG, Brazil., Martho K; Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, 09972-270 Diadema-SP, Brazil., Lima R; Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, 09972-270 Diadema-SP, Brazil., Pascon RC; Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, 09972-270 Diadema-SP, Brazil., Vallim MA; Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, 09972-270 Diadema-SP, Brazil., Capello TM; Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, 09972-270 Diadema-SP, Brazil., Romoff P; Escola de Engenharia, Universidade Presbiteriana Mackenzie, 01302-090 São Paulo-SP, Brazil., Sartorelli P; Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, 09972-270 Diadema-SP, Brazil., Lago JH; Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, 09972-270 Diadema-SP, Brazil. joao.lago@unifesp.br.
Jazyk: angličtina
Zdroj: Molecules (Basel, Switzerland) [Molecules] 2014 Jun 06; Vol. 19 (6), pp. 7528-42. Date of Electronic Publication: 2014 Jun 06.
DOI: 10.3390/molecules19067528
Abstrakt: 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.
Databáze: MEDLINE