Lipids and essential oils as antimicrobial agents

338 Pages·2011·2.38 MB·English

by  Thormar H. (ed.)

RED BOX RULES ARE FOR PROOF STAGE ONLY. DELETE BEFORE FINAL PRINTING.
Lipids and Editor
Th ormar
Essential Oils
as Antimicrobial Agents
Editor: Halldor Th ormar
Faculty of Life and Environmental Sciences, University of Iceland
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Lipids and essential oils have strong antimicrobial properties - they kill or inhibit the growth of i
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microbes such as bacteria, fungi, and viruses. Th ey are being studied for use in the prevention and
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treatment of infections, as potential disinfectants, and for their preservative and antimicrobial s
properties when formulated as pharmaceuticals, in food products, and in cosmetics. n
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Lipids and Essential Oils as Antimicrobial Agents is a comprehensive review of the scientifi c in
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knowledge in this fi eld. International experts provide summaries on:
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• antibacterial, antiviral and antifungal activities of lipids c
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• membranes as targets of antimicrobial lipids r
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• antimicrobial lipids in milk s
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• antimicrobial lipids of the skin and tear fi lm s Editor Halldor Th ormar
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• antimicrobial lipids and innate immunity ae
• lipids as active ingredients in pharmaceuticals, cosmetics and health foods ln

• antimicrobial lipids as disinfectants, antiseptics and sanitizers At
• the chemistry and bioactivity of essential oils i LLiippiiddss aanndd
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• antiviral eff ects of plant-derived essential oils and pure oil components e
• antibacterial and antifungal activities of essential oils nl

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Lipids and Essential Oils as Antimicrobial Agents is an essential guide to this important topic s
for researchers and advanced students in academia and research working in pharmaceutical,
i Essential Oils
cosmetic and food sciences, biochemistry and natural products chemistry, microbiology; and l
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for health care scientists and professionals working in the fi elds of public health and infectious
diseases. It will also be of interest to anyone concerned about health issues and particularly to
those who are conscious of the benefi ts of health food and natural products.
as Antimicrobial Agents
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Lipids and Essential Oils as
Antimicrobial Agents
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Lipids and Essential Oils
as Antimicrobial Agents
Editor
HALLDOR THORMAR
Faculty of Life and Environmental Sciences, University of Iceland,
Reykjavik, Iceland
A John Wiley and Sons, Ltd., Publication
iii
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Thiseditionfirstpublished2011
(cid:1)C 2011JohnWiley&Sons,Ltd
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LibraryofCongressCataloging-in-PublicationData
Lipidsandessentialoilsasantimicrobialagents/editor,HalldorThormar.
p.;cm.
Includesbibliographicalreferencesandindex.
ISBN978-0-470-74178-8(cloth)–ISBN978-0-470-97661-6(ebook)–ISBN978-0-470-97662-3(obook)
1.Anti-infectiveagents. 2.Lipids–Therapeuticuse. 3.Essencesandessentialoils–Therapeuticuse. I.Thormar,Halldor.
[DNLM:1.Anti-InfectiveAgents. 2.Lipids–pharmacology. 3.Oils,Volatile–pharmacology. QV250]
RM267.L572011
615(cid:2).792–dc22
2010037014
AcataloguerecordforthisbookisavailablefromtheBritishLibrary.
PrintISBN: 9780470741788
eBookISBN: 9780470976616
oBookISBN: 9780470976623
ePubISBN: 9780470976678
Typesetin10/12ptTimesbyAptaraInc.,NewDelhi,India.
PrintedandboundinSingaporebyMarkonoPrintMediaPteLtd.
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Contents
ListofContributors xi
Introduction xiii
1 MembranesasTargetsofAntimicrobialLipids 1
PeterJ.Quinn
1.1 Introduction 2
1.2 OilandWaterDon’tMix! 2
1.3 PolarLipids 3
1.3.1 TheAmphiphilicCharacterofPolarLipids 3
1.3.2 HydrophobicConstituentsofLipids 4
1.3.3 PolarGroupsofComplexLipids 5
1.4 PropertiesofSurfactants 7
1.4.1 CriticalMicelleConcentration 7
1.4.2 AggregationofSurface-ActiveMolecules 8
1.4.3 TheInfluenceofSolvent 9
1.5 CellMembranes 11
1.5.1 MembraneLipids 11
1.5.2 LipidDomainsinMembranes 13
1.5.3 MembraneProteins 15
1.5.4 MembraneStability 15
1.5.4.1 MembraneLipidPhaseBehaviour 17
1.5.4.2 MembraneLipidHomeostasisinHomoiothermicOrganisms18
1.5.4.3 MembraneLipidAdaptioninPoikilothermicOrganisms 19
1.6 TheActionofAntimicrobialLipidsonCellMembranes 20
1.7 Conclusions 21
Acknowledgements 21
References 22
2 AntibacterialEffectsofLipids:HistoricalReview(1881to1960) 25
HalldorThormar
2.1 Introduction 25
2.2 AntibacterialActivityofSoaps 26
2.2.1 AntibacterialActionofFattyAcidsandTheirDerivatives 29
2.3 InhibitionofLipidsandSerumAlbuminagainsttheAntibacterial
ActionofSoaps 33
2.4 DiverseActionsofFattyAcidsandTheirSaltsonBacteria 34
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2.5 TheNatureoftheBactericidalActionofFattyAcids 36
2.6 APossibleRoleofSoapsandFattyAcidsinHostDefenceagainst
Bacteria 38
2.7 StudiesofProphylacticandTherapeuticApplicationsofSoapsand
FattyAcids 40
2.8 Conclusions 43
References 43
3 Antibacterial,AntiviralandAntifungalActivitiesofLipids 47
GudmundurBergsson,HilmarHilmarssonandHalldorThormar
3.1 Introduction 48
3.2 AntibacterialActivitiesofFattyAcidsandMonoglycerides 48
3.2.1 ActivitiesagainstGram-PositiveBacteriaInVitro 48
3.2.2 ActivitiesagainstGram-NegativeBacteriaInVitro 51
3.2.3 AntibacterialMechanism 53
3.2.4 APossibleRoleofAntimicrobialLipidsinHostDefence
againstBacteria 57
3.3 AntiviralActivitiesofFattyAlcohols,FattyAcidsandMonoglycerides 58
3.3.1 EarlyStudiesofAntiviralLipids 58
3.3.2 AntiviralActivitiesofMilkLipids 60
3.3.3 AntiviralActivitiesofLipidsandFattyAlcohols 61
3.3.4 AntiviralMechanismofLipids 65
3.4 AntifungalActivitiesofFattyAcidsandMonoglycerides 67
3.4.1 InVitroStudies 67
3.4.2 InVivoStudies 71
3.5 Conclusions 74
References 75
4 AntimicrobialLipidsinMilk 81
CharlesE.Isaacs
4.1 Introduction 82
4.2 Occurrence 83
4.2.1 Biosynthesis 83
4.2.2 QuantitativeAssays 83
4.2.2.1 MeasurementofAntibacterialActivity 83
4.2.2.2 MeasurementofAntiviralActivity 84
4.3 MolecularProperties 84
4.3.1 LipidsinMilkandPlantOils 84
4.3.2 DependenceofAntimicrobialActivityonChainLength,
SaturationandpH 85
4.4 AntimicrobialActivity 85
4.4.1 MechanismofAction 85
4.4.2 SynergybetweenAntimicrobialLipidsandAntimicrobial
Peptides 87
4.4.2.1 AntimicrobialPeptidesandProteins 87
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4.4.2.2 PotentialSynergismbetweenAntimicrobialMilk
LipidsandPeptides 88
4.4.3 InfluencingFactors 88
4.4.4 Spectrum 89
4.5 Applications 89
4.5.1 AdditiveAdvantagetoFoodsandBiologicalProducts 89
4.5.2 PhysiologicalAdvantage 90
4.5.3 SexuallyTransmittedPathogensandTopicalActivity 91
4.6 Safety,ToleranceandEfficacy 91
4.7 Conclusions 92
References 92
5 AntimicrobialLipidsoftheSkinandTearFilm 99
CarolL.Bratt,PhilWertz,DavidDrake,DeborahV.Dawsonand
KimA.Brogden
5.1 Introduction 100
5.2 InnateImmuneMechanismsinSkin 101
5.2.1 TheExtensiveCutaneousMicrobialBurden 101
5.2.2 CutaneousInnateImmuneMechanisms 104
5.3 TypesandLocationsofLipidsoftheSkinandTearFilm 106
5.3.1 HypodermalandDermalLipids 107
5.3.2 EpidermalLipids 107
5.3.3 SecretedLipids 109
5.3.4 Tear-FilmLipids 109
5.4 FunctionsofLipids 111
5.4.1 CutaneousLipidsasPermeabilityBarriers 111
5.4.2 CutaneousLipidsasInnateImmuneMechanisms 111
5.5 AntimicrobialActivityofLipidsandTheirMechanismsofKilling 111
5.5.1 LipidDeficiencies 112
5.5.2 LipidAntimicrobialActivityandMechanismofAction 112
5.5.2.1 Sphingolipids 113
5.5.2.2 Fattyacids 114
5.6 SynergyofCutaneousLipidsandOtherInnateImmuneMolecules 114
5.7 LipidsasTherapeuticAgents 115
5.8 Conclusions 115
Acknowledgements 116
References 116
6 AntimicrobialLipidsandInnateImmunity 123
HalldorThormar
6.1 Introduction 124
6.2 TheRoleofHumanMilkLipidsinInnateImmunity 126
6.2.1 Breast-FeedingProtectsInfantsagainstInfection 126
6.2.2 FactorsinHumanMilkwhichProtectagainstInfection 127
6.2.3 AntmicrobialLipidsinHumanMilkandTheirPossible
ProtectiveFunction 129
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6.3 AntimicrobialLipidsinthePulmonaryMucosa 134
6.3.1 TheInnateImmuneSystemoftheRespiratoryTract 134
6.3.2 AntimicrobialFattyAcidsintheAlveoliofAnimaland
HumanLungs 135
6.4 AntimicrobialSkinLipids 137
6.4.1 TheSelf-DisinfectingPoweroftheHumanSkin 137
6.4.2 TheRoleofSkinLipidsintheSelf-DisinfectionofHumanSkin 137
6.4.3 SebumLipidsasaSourceofAntimicrobialFattyAcidsintheSkin 139
6.4.4 StratumCorneumasaSourceofAntimicrobialLipidsintheSkin 142
6.4.5 AntimicrobialLipidsasaPartoftheInnateImmuneDefence 144
6.5 Conclusions 144
References 144
7 LipidsasActiveIngredientsinPharmaceuticals,Cosmeticsand
HealthFoods 151
Tho´rd´ısKristmundsdo´ttirandSku´liSku´lason
7.1 Introduction 152
7.2 AntimicrobialEffectsofLipids 152
7.2.1 AntibacterialActivity 152
7.2.2 AntiviralActivity 153
7.2.3 AntifungalActivity 154
7.3 LipidsinPharmaceuticals 155
7.3.1 LipidsinPharmacopeias 155
7.3.2 MicrobicidalLipidsforTreatmentofMucosalandSkinInfections 155
7.3.3 LipidsasPenetrationEnhancersinPharmaceuticalDosageForms 159
7.4 MicrobicidalLipidsinAgricultureandAquaculture 160
7.5 LipidsinTherapy 163
7.5.1 EffectofLipidsonInfectiousandInflammatoryDiseases 163
7.5.2 EffectofLipidsonPsoriasis 165
7.5.3 EffectofLipidsonCardiovascularDiseases 165
7.5.4 EffectofLipidsonCognitiveFunction 166
7.6 LipidsinCosmetics 167
7.6.1 SourcesofLipidsUsedinCosmetics 167
7.6.2 AntimicrobialActivityofLipidsinCosmetics 168
7.6.3 OtherActivitiesofLipidsinCosmetics 169
7.7 LipidsinHealthFood 169
7.8 Conclusions 171
References 171
8 AntimicrobialLipidsasDisinfectants,AntisepticsandSanitizers 179
HalldorThormarandHilmarHilmarsson
8.1 Introduction 179
8.2 SoapsasDisinfectantsandAntiseptics 182
8.3 UseofBactericidalLipidstoReduceMicrobialContaminationofFood
Products 184