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

Author(s):Show less -

Grecco, Simone dos S. ^{[1, 2]} ; Dorigueto, Antonio C. ^[3] ; Landre, Iara M. ^[3] ; Soares, Marisi G. ^[3] ; Martho, Kevin ^[1] ; Lima, Ricardo ^[1] ; Pascon, Renata C. ^[1] ; Vallim, Marcelo A. ^[1] ; Capello, Tabata M. ^[1] ; Romoff, Paulete ^[4] ; Sartorelli, Patricia ^[1] ; Lago, Joao Henrique G. ^[1]

Affiliation

^[1] Univ Fed Sao Paulo, Inst Ciencias Ambientais Quim & Farmaceut, BR-09972270 Diadema, SP - Brazil

^[2] Univ Fed ABC, Ctr Ciencias Nat & Humanas, BR-09090400 Santo Andre, SP - Brazil

^[3] Univ Fed Alfenas, Inst Quim, BR-37130000 Alfenas, MG - Brazil

^[4] Univ Presbiteriana Mackenzie, Escola Engn, BR-01302090 Sao Paulo - Brazil

• Document type: Journal article
• Source: Molecules; v. 19, n. 6, p. 7528-7542, JUN 2014.
• Web of Science Citations: 4

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 mu g/mu L. 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. (AU)

• FAPESP's process: 11/51739-0 - Sustainable use of biodiversity in Atlantic Forest remnants in São Paulo: evaluation, isolation and molecular characterization of bioactive secondary metabolites in plant species
• Grantee: João Henrique Ghilardi Lago
• Support Opportunities: BIOTA-FAPESP Program - Regular Research Grants
• FAPESP's process: 06/57626-5 - Selection of potential molecules in plant species of São Paulo State highlands: chemical structure, relationship structure / biological activity associated with ecophysiological considerations
• Grantee: João Henrique Ghilardi Lago
• Support Opportunities: Research Grants - Young Investigators Grants