title: Bioautography and chemical characterization of antimicrobial compound(s) in commercial water-soluble annatto extracts.
abstract: Annatto preparations based on extracts of the seed of tropical bush Bixa orellana L consist of carotenoid-type pigments. Previous reports indicate that commercial annatto extracts have biological activities against microorganisms of significance to food fermentation, preservation, and safety. The objective of this study was to separate and identify the compound(s) responsible for the antimicrobial activity of annatto preparations. Commercial water-soluble annatto extracts were screened by thin-layer chromatography and bioautography followed by liquid chromatography/photodiode array/mass spectrometry (LC/PDA/MS) analysis of active fractions. Bioautography revealed two fractions with antimicrobial activity against Staphylococcus aureus. LC/PDA/MS analysis of both fractions revealed 9'-cis-norbixin (UV(max) 460 and 489 nm) and all-trans-norbixin (UV(max) 287, 470, and 494 nm) as the major components. Structure confirmation was achieved by (1)H NMR spectroscopy. Results indicate that 9'-cis-norbixin and all-trans-norbixin are responsible for the antimicrobial properties of annatto.
authors.affiliation: Monell Chemical Senses Center, 3500 Market Street, Philadelphia, Pennsylvania 19104-3308, USA.
authors.forename: Veronica
authors.initials: V
authors.lastname: Galindo-Cuspinera
authors.forename: Scott A
authors.initials: SA
authors.lastname: Rankin
mesh_terms: D000890:Anti-Infective Agents / Q000737:chemistry* / Q000302:isolation & purification*; D001419:Bacteria / Q000187:drug effects; D031212:Bixaceae; D002338:Carotenoids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D002853:Chromatography, Liquid; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010936:Plant Extracts / Q000737:chemistry*; D012995:Solubility; D014867:Water
chemical_list: D000890:Anti-Infective Agents; D010936:Plant Extracts; D014867:Water; D002338:Carotenoids; C054041:annatto; C099823:norbixin