title: Structural crystalline characterization of sakuranetin--an antimicrobial flavanone from twigs of Baccharis retusa (Asteraceae).
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.
authors.affiliation: Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, 09972-270 Diadema-SP, Brazil.
authors.forename: Simone
authors.initials: S
authors.lastname: dos S Grecco
authors.affiliation: Instituto de Química, Universidade Federal de Alfenas, 37130-000 Alfenas-MG, Brazil.
authors.forename: Antônio C
authors.initials: AC
authors.lastname: Dorigueto
authors.affiliation: Instituto de Química, Universidade Federal de Alfenas, 37130-000 Alfenas-MG, Brazil.
authors.forename: Iara M
authors.initials: IM
authors.lastname: Landre
authors.affiliation: Instituto de Química, Universidade Federal de Alfenas, 37130-000 Alfenas-MG, Brazil.
authors.forename: Marisi G
authors.initials: MG
authors.lastname: Soares
authors.affiliation: Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, 09972-270 Diadema-SP, Brazil.
authors.forename: Kevin
authors.initials: K
authors.lastname: Martho
authors.affiliation: Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, 09972-270 Diadema-SP, Brazil.
authors.forename: Ricardo
authors.initials: R
authors.lastname: Lima
authors.affiliation: Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, 09972-270 Diadema-SP, Brazil.
authors.forename: Renata C
authors.initials: RC
authors.lastname: Pascon
authors.affiliation: Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, 09972-270 Diadema-SP, Brazil.
authors.forename: Marcelo A
authors.initials: MA
authors.lastname: Vallim
authors.affiliation: Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, 09972-270 Diadema-SP, Brazil.
authors.forename: Tabata M
authors.initials: TM
authors.lastname: Capello
authors.affiliation: Escola de Engenharia, Universidade Presbiteriana Mackenzie, 01302-090 São Paulo-SP, Brazil.
authors.forename: Paulete
authors.initials: P
authors.lastname: Romoff
authors.affiliation: Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, 09972-270 Diadema-SP, Brazil.
authors.forename: Patricia
authors.initials: P
authors.lastname: Sartorelli
authors.affiliation: Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, 09972-270 Diadema-SP, Brazil. joao.lago@unifesp.br.
authors.forename: João Henrique G
authors.initials: JH
authors.lastname: Lago
mesh_terms: D000890:Anti-Infective Agents / Q000737:chemistry* / Q000494:pharmacology*; D019659:Asteraceae / Q000737:chemistry*; D002175:Candida / Q000187:drug effects; D003454:Cryptococcus / Q000187:drug effects; D005419:Flavonoids / Q000737:chemistry* / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D012441:Saccharomyces cerevisiae / Q000187:drug effects; D000094162:Phytoalexins
chemical_list: D000890:Anti-Infective Agents; D005419:Flavonoids; C099724:sakuranetin; D000094162:Phytoalexins