Bioautography and Chemical Characterization of Antimicrobial Compound(s) in Commercial Water-Soluble Annatto Extracts

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 ob...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2005-04, Vol.53 (7), p.2524-2529
Main Authors: Galindo-Cuspinera, Veronica, Rankin, Scott A
Format: Article
Language:English
Subjects:
Anti-Infective Agents - chemistry
Anti-Infective Agents - isolation & purification
antibacterial properties
Bacteria - drug effects
Biological and medical sciences
Bixa orellana
Bixaceae
carotenoids
Carotenoids - chemistry
Carotenoids - isolation & purification
Carotenoids - pharmacology
chemical composition
Chromatography, Liquid
food coloring
Food industries
Food microbiology
food preservatives
Fundamental and applied biological sciences. Psychology
Hydrogen-Ion Concentration
Magnetic Resonance Spectroscopy
Mass Spectrometry
norbixin
Plant Extracts - chemistry
seed extracts
Solubility
Staphylococcus aureus
Water
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Summary: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 (UVmax 460 and 489 nm) and all-trans-norbixin (UVmax 287, 470, and 494 nm) as the major components. Structure confirmation was achieved by 1H NMR spectroscopy. Results indicate that 9‘-cis-norbixin and all-trans-norbixin are responsible for the antimicrobial properties of annatto. Keywords: Annatto; achiote; bioautography; antimicrobial; carotenoids; natural colorant; norbixin; LC/PDA/MS
ISSN:0021-8561
1520-5118
DOI:10.1021/jf048056q