Canada Research Chair in Food Microbiology and Probiotics Department of Agricultural, Food and Nutritional Science Edmonton, Alberta, Canada www.ualberta.ca.

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Presentation transcript:

Canada Research Chair in Food Microbiology and Probiotics Department of Agricultural, Food and Nutritional Science Edmonton, Alberta, Canada Antimicrobial compounds from plants Michael G. Gänzle, Christina Engels, and Andreas Schieber

Role of Lipoxygenases in Plants Inhibition of microbial growth after injury Cell signalling after wounding and pathogen attack Synthesis of attractors to enemies of herbivores Lipid mobilisation during germination Regulation of vegetative growth Parasitic wasp (Cotesia marginiventris) Beet Armyworm

Role of Phenolic Compounds in Plants Pigments Attractants Protection against pests Protection against UV irradiation I don‘t like it !!! Defence systems preformedinduced

C 6 -C 1 CompoundsC 6 -C 3 Compounds C6C6C6C6 C6C6C6C6 Phenolic Acids C 6 -C 1 -C 6 Compounds Xanthones C 6 -C 2 -C 6 Compounds Stilbenes C 6 -C 3 -C 6 Compounds Flavonoids C6C6C6C6 C6C6C6C6 C6C6C6C6 C6C6C6C6 C6C6C6C6 C6C6C6C6 Diversity of Plant Polyphenols

COMP. REV. FOOD SCI. FOOD SAFETY 8: 157 Antimicrobial compounds from plants: an overview

Antimicrobial polyphenols from plants: Limitations for food applications - Much of the literature data is based on complex mixture of compounds => are Canadian berries the same as Finnish berries? - Compounds have potent biological and technological activities other than antimicrobial activity => blue beef with citrus flavour? - Limited data on mode of action of polyphenols => Interactions with other hurdles applied in food processing?

Antimicrobial activity of mango polyphenols Mangifera indica L. World production: 30 Mio t./year 35 – 60% peels and kernels Recovery of valuable compounds?

HPLC Profile of Phenolic Compounds From Mango Kernel Extracts Food Chem 71, 61 Antimicrobially active fractions HydrolyzableTannins Rapid Commun Mass Spectrom 18, 2208

Tannins Subclass of polyphenols (to) tan = precipitate proteins Condensed and hydrolyzable tannins: Polyol core esterified with phenolic acids Penta-O-galloylglucose

Purification of tannins Extract with hexane Extract with aqueous acetone Liquid-liquid extraction Ethyl acetate phase Aqueous phase Dichloromethane phase Low Pressure Liquid Chromatography Fractions 1 to 3 Fractions 4.6 and 5.3 Semi-preparative HPLC Penta-O-galloylglucose Hepta-O-galloylglucose Hexa-O-galloylglucose Dried mango kernels  Purification of fractions with antimicrobial activity Engels et al., J Agric Food Chem 57:7712

Antimicrobial activity of purified gallotannins a) Diameter of zone of inhibition (cm); b) -, no inhibition

Gallotannin-Iron complex visualised by CAS agar diffusion assay Gallic acidMangiferinTannic acid EDTA Mango kernel extract

Effect of iron on antimicrobial activity of mango kernel extract Fe 2+ Fe 3+ Indicator strain: B. subtilis.

Antimicrobial activity of mango gallotannins - interim summary - - Gallotannins from mango exhibit highly selective antibacterial activity - Gallotannins have tanning and iron-complexing activities Further studies to determine minimum inhibitory activities and the mode of action require higher concentrations of purified compounds!

High Speed Counter Current Chromatography High-speed counter current chromatography Isolation and purification of compounds Larger sample injections for preparative purification! HSCCC Extract with hexane Extract with aqueous acetone Liquid-liquid extraction Ethyl acetate phase Aqueous phase Dichloromethane phase Low Pressure Liquid Chromatography Fractions 1 to 3 Fractions 4.6 and 5.3 Semi-preparative HPLC Penta-O-galloylglucose Hepta-O-galloylglucose Hexa-O-galloylglucose Dried mango kernels X

Component A Component B High Speed Counter Current Chromatography: Principle of Separation

Component A Component B High Speed Counter Current Chromatography: Principle of Separation

HSCCC

G F E D C A Separation of mango gallotannins by HSCCC B

Identity and purity of gallotannins: LC/MS

Antimicrobial activities of gallotannins: Structure-function relationships MIC Concentration to withdraw iron from CAS*Fe complex

Antimicrobial activities of gallotannins: Inhibitory spectrum Food Chem 71, 61, J Agric Food Chem 57:7712

Mode of action of gallotannins Resistance of lactic acid bacteria and bifidobacteria: the iron anomaly Lactic acid bacteria and bifidobacteria do not require iron for growth as their metabolism depends neither on Fe-S enzymes of the respiratory chain (all aerobes), nor on Fe-S enzymes involved in metabolic pathways of strict anaerobes. Resistance of Enterobacteriaceae and plant pathogens: - permeability barrier of the outer membrane? - production of siderophores for iron sequestration?

Food and Feed applications of gallotannins - perspectives - Highly selective antimicrobial activity - selective inhibition of pathogens, coupled with stimulation of protective lactic acid bacteria on food? - beneficial shifts of intestinal microbiota in feed applications? Role of cations in antimicrobial activity - Do other divalent cations (Ca 2+, Mg 2+ ) mitigate antimicrobial activity of gallotannins? - Does tanning activity alter food qualitiy? - reduced iron availability in food and feed?

Exploration of the diversity of plant bioactives by => Preparative purification of active compounds => Determination of structure-function relationships => Mode of action and relationship of antimicrobial activity to other biological activities Antimicrobial compounds from plants: Limiations and perspectives - Most literature data is based on complex mixture of compounds - Compounds have potent biological and technological activities other than antimicrobial activity - Very limited data on mode of action

Acknowledgements Collaborators Dr. Reinhold Carle, U Hohenheim, Germany Financial support NSERC and Research Chairs of Canada …..for your attention

UV Absorbance G F E Characterisation of fractions by LC/MS

10 GG 9 GG 8 GG 7 GG 6 GG 5 GG Separation of mango gallotannins by HSCCC 4 GG

Meta-depsidic bonding Structural isomers of gallotannins

Salicylic acid 4-Hydroxy- benzoic acid Proto- catechuic acid Gallic acid Willow barks Berries Onion/potatoskins Mango peels, grapes Preservatives C 6 -C 1 Compounds: Hydroxybenzoic Acids

Volatile formation from lipid peroxides by Lipoxygenase Linoleic acid 13-LOOH hexanal + 12-oxo-9-cis-dodecenoic acid -Injury of plant tissue disrupts separation of enzyme and substrate! LOX

Antioxidant and antimicrobial activities of mango (Mangifera indica L.) by-products Christina Engels – September 17, 2008 Characterization Analytical HPLC puglkg Dried mango kernels and peels Extract with aqueous acetone Liquid-liquid-partitioning Ethyl acetate phase Aqueous remains Dichloromethane phase Low Pressure Liquid Chromatography Fraction 1 to 3Fraction 4.1 to 5.8 Semi-prep HPLC Penta-O-galloylglucose Hepta-O-galloylglucose Hexa-O-galloylglucose HPLC MS AB AntiOx Penta-O-galloylglucose Hexa-O-galloylglucose Hepta-O-galloylglucose