Gang The Biological Activity of Phytochemicals

1. Auflage 2010
ISBN: 978-1-4419-7299-6
Verlag: Springer-Verlag
Format: PDF
Kopierschutz: Adobe DRM (»Systemvoraussetzungen)

E-Book, Englisch, 214 Seiten

This is the first volume to be published under a new series agreement for Recent Advances in Phytochemistry, co-published with the Phytochemical Society of North America.

Autoren/Hrsg.

Gang, David

Inhaltsverzeichnis

1;Preface;6
2;Contents;9
3;Contributors;11
4;1 The Pursuit of Potent Anti-influenza Activity from the Antarctic Red Marine Alga Gigartina skottsbergii ;14
4.1;1.1 The Necessity for Antiviral Treatments;14
4.2;1.2 Natural Products: Red Marine Algae and the Antarctic Peninsula;15
4.3;1.3 Primary and Secondary Screening of Extract Library;16
4.4;1.4 Purification of Active Extract;18
4.5;1.5 Insight into the Mechanism of Action via Hemagglutination Assay and Drug Combination Studies;20
4.6;1.6 Conclusions;22
4.7;1.7 Experimental;22
4.8;References;24
5;2 Ginsenosides: Phytoanticipins or Host Recognition Factors;26
5.1;2.1 Introduction;26
5.2;2.2 Saponins;26
5.2.1;2.2.1 Chemical Structure and Diversity;26
5.2.2;2.2.2 Involvement of Saponins in Host--Pathogen Interactions;28
5.2.2.1;2.2.2.1 Avenacin A-1 and -Tomatine as Models for Plant Defense;28
5.2.2.2;2.2.2.2 Mode of Action Through Membrane Disruption;29
5.3;2.3 Ginsenosides Are Bidesmosidic Saponins with Mild Fungitoxicity;29
5.3.1;2.3.1 Structure, Nomenclature, and Biosynthesis of Ginseng Saponins;29
5.3.2;2.3.2 Distribution of Ginsenosides Within the Plant;30
5.3.3;2.3.3 Fungitoxicity of Ginsenosides;31
5.3.4;2.3.4 Ginsenosides in the Rhizosphere;32
5.4;2.4 Some Pathogens Can Degrade/Detoxify Saponins;32
5.4.1;2.4.1 Overview of ''Saponinases'' from Plant Pathogens;32
5.4.2;2.4.2 The Metabolism of Ginsenosides by Pathogens of Ginseng;34
5.4.3;2.4.3 P. irregulare Specifically Deglycosylates 20(S)-Protopanaxadiol Ginsenosides into Ginsenoside F2;35
5.4.4;2.4.4 P. irregulare Ginsenosidases Are Induced by Exposure to Ginsenosides In Vitro;35
5.4.5;2.4.5 Purification and Characterization of Ginsenosidases from P. irregulare;38
5.5;2.5 The Involvement of Ginsenosides and Ginsenosidases in the Ginseng-P. irregulare Pathosystem ;39
5.6;2.6 Summary and Future Directions;41
5.7;References;41
6;3 Fractionation of Grape Seed Proanthocyanidins for Bioactivity Assessment;46
6.1;3.1 Introduction;46
6.2;3.2 Methods for PA Extraction, Separation, and Analysis;48
6.2.1;3.2.1 Extraction of Grape Seed PAs;48
6.2.2;3.2.2 Fractionation of PAs;48
6.2.2.1;3.2.2.1 Solvent Precipitation;49
6.2.2.2;3.2.2.2 Fractionation on Toyopearl HW-40S;50
6.2.3;3.2.3 Quantification of PAs;51
6.2.4;3.2.4 Determination of PA Complexity;52
6.2.5;3.2.5 Determination of the Mean Degree of Polymerization of PAs;53
6.3;3.3 Case Studies for Fractionation of MegaNatural-AZ GSE;53
6.3.1;3.3.1 Solvent Precipitation;54
6.3.2;3.3.2 Fractionation on Toyopearl Resin;56
6.4;3.4 Conclusions;57
6.5;References;58
7;4 Coloring Soybeans with Anthocyanins;60
7.1;4.1 Anthocyanin Biosynthesis in Black Soybean for the Visual Identification of Transgenic Grains;60
7.2;4.2 Anthocyanins in Black Soybean;61
7.2.1;4.2.1 Anthocyanin Composition in the Seed Coat of Black Soybean;61
7.2.2;4.2.2 Anthocyanin Biosynthesis, Flux, and Accumulation in Black Soybean;61
7.3;4.3 Is the Black Color in Plants Determined by Anthocyanins;65
7.3.1;4.3.1 Anthocyanin Levels Versus Composition in Black Plant Tissues;65
7.3.2;4.3.2 Are Anthocyanic Vacuolar Inclusions (AVIs) Required to Color Plant Tissues Black?;65
7.3.3;4.3.3 Does Co-pigmentation and Oxidation Have a Role in Blackening Seeds?;67
7.4;4.4 Engineering Seed Coat Color for the Visual Identification of Transgenic Grains;67
7.5;4.5 Concluding Remarks and Future Perspectives;68
7.6;References;68
8;5 Pharmacogenetics in Potential HerbDrug Interactions: Effects of Ginseng on CYP3A4 and CYP2C9 Allelic Variants;71
8.1;5.1 Introduction: Ginseng Drug Interactions;71
8.2;5.2 Cytochrome P450 (CYP) Enzymes;71
8.3;5.3 The Role of Polymorphisms;72
8.4;5.4 Recent Results on CYP3A4 and CYP2C9 Allelic Variants;73
8.5;5.5 Future Implications;75
8.6;5.6 Conclusions;76
8.7;References;77
9;6 Biosynthesis and Function of Citrus Glycosylated Flavonoids;78
9.1;6.1 Citrus Flavonoids and Flavonoid Glycosides;78
9.2;6.2 Biosynthesis of Flavonoids in Citrus;80
9.2.1;6.2.1 Phenylalanine Ammonia Lyase;80
9.2.2;6.2.2 Cinnamate 4-Hydroxylase;83
9.2.3;6.2.3 4-Coumarate:CoA Ligase;84
9.2.4;6.2.4 Chalcone Synthase;84
9.2.5;6.2.5 Chalcone Isomerase;85
9.2.6;6.2.6 Flavanone 3-Hydroxylase;86
9.2.7;6.2.7 Flavone Synthase;87
9.2.8;6.2.8 Flavonol Synthase;88
9.2.9;6.2.9 Dihydroflavonol 4-Reductase;89
9.2.10;6.2.10 Anthocyanidin Synthase;90
9.2.11;6.2.11 Flavanone 3'-Hydroxylase ;90
9.2.12;6.2.12 Flavanone 3', 5'-Hydroxylase ;91
9.3;6.3 Flavonoid Glycosylation in Citrus;91
9.3.1;6.3.1 Specificity of Flavonoid Glycosyltransferases in Citrus;97
9.4;6.4 Function of Citrus Flavonoid Glycosides;97
9.5;6.5 Concluding Remarks and Future Perspectives;98
9.6;References;98
10;7 Ginsenoside Variation Within and Between Ontario Ginseng Landraces: Relating Phytochemistry to Biological Activity;107
10.1;7.1 Introduction;107
10.2;7.2 Methods;108
10.2.1;7.2.1 Ginseng Collection and Extraction;108
10.2.2;7.2.2 HPLC-DAD Analysis;109
10.2.3;7.2.3 Anti-glycation Activity;109
10.2.4;7.2.4 Antioxidant Activity;109
10.2.5;7.2.5 Statistics;110
10.3;7.3 Results and Discussion;110
10.3.1;7.3.1 Ginsenoside Variation;110
10.3.2;7.3.2 Anti-glycation and Antioxidant Activity of Ginseng In Vitro;113
10.4;7.4 Conclusions and Future Directions;114
10.5;References;116
11;8 Heat, Color, and Flavor Compounds in Capsicum Fruit;118
11.1;8.1 Peppers;118
11.2;8.2 Pigments;119
11.2.1;8.2.1 Chlorophyll;119
11.2.2;8.2.2 Carotenoids;120
11.3;8.3 Biosynthesis of Carotenoids in Peppers;121
11.4;8.4 Carotenoid Analysis;123
11.4.1;8.4.1 Anthocyanins;125
11.5;8.5 Capsaicinoids;125
11.5.1;8.5.1 Capsaicinoids Are Products of the Phenylpropanoid Pathway and the Branched Chain Fatty Acid Pathway;127
11.5.2;8.5.2 Capsaicinoids Accumulate in the Epidermal Cells of the Placenta;128
11.5.3;8.5.3 Genetic and Environmental Effects on the Expression of Pungency;128
11.6;8.6 Flavors or Volatile Aroma Compounds;129
11.7;8.7 Concluding Remarks;130
11.8;References;130
12;9 Fungal Attack and Cruciferous Defenses: Tricking Plant Pathogens;136
12.1;9.1 PlantPathogen Interactions: A Never-Ending Arms Race;136
12.2;9.2 Pathogen Attack: Phytotoxins and Elicitors from Cruciferous Fungi;137
12.3;9.3 Cruciferous Defenses: Phytoanticipins and Phytoalexins;141
12.4;9.4 Pathogen Counterattack: Fungal Detoxifying Enzymes and Paldoxins;144
12.5;9.5 Concluding Remarks and Future Perspectives;145
12.6;References;146
13;10 Glucosinolate Degradation Products in Fermented Meadowfoam Seed Meal and Their Herbicidal Activities;149
13.1;10.1 Introduction;149
13.2;10.2 Analytical Procedures;151
13.2.1;10.2.1 Isolation and Structure Determination of Glucolimnanthin from Meadowfoam Seed Meal;151
13.2.2;10.2.2 HPLC Analysis of Glucolimnanthin;152
13.2.3;10.2.3 Characterization of Glucosinolates by HPLC--Mass Spectrometry Using Precursor Ion Scanning;155
13.2.4;10.2.4 Identification of the Aglycone Moiety of the L. floccosa Glucosinolate with m/z 424 ;155
13.3;10.3 Herbicidal Activity of Glucolimnanthin and Its Degradation Products;158
13.3.1;10.3.1 Fermentation of Meadowfoam Seed Meal;158
13.3.2;10.3.2 Herbicidal Activity of Glucolimnanthin 1 and Its Individual Degradation Products 2--5;159
13.3.3;10.3.3 Herbicidal Activity of Fermented Meadowfoam Seed Meal;160
13.4;References;162
14;11 Elucidating the Metabolism of Plant Terpene Volatiles: Alternative Tools for Engineering Plant Defenses;166
14.1;11.1 Introduction;166
14.2;11.2 Targeting Volatile Terpene Biosynthesis for Manipulating Indirect Plant Defenses;168
14.3;11.3 Arabidopsis: A Small Weed and Its Genetic Resources for Volatile Terpene Biosynthesis;170
14.4;11.4 How Does Arabidopsis Assemble Homoterpene Volatiles;171
14.4.1;11.4.1 Formation of Alcohol Precursors;171
14.4.2;11.4.2 Oxidative Degradation of Geranyllinalool to TMTT;175
14.4.3;11.4.3 Subcellular Compartmentalization of Homoterpene Biosynthesis;176
14.5;11.5 Metabolic Engineering of Homoterpene Volatiles;177
14.6;11.6 Conclusions and Future Challenges;179
14.7;References;180
15;12 Stereoselectivity of the Biosynthesis of Norlignans and Related Compounds;186
15.1;12.1 Introduction;186
15.2;12.2 Norlignan Biosynthesis;187
15.3;12.3 Lignan Biosynthesis;191
15.3.1;12.3.1Lignans with 9(9')-Oxygen ;191
15.3.2;12.3.2 Other Types of Lignans;197
15.3.3;12.3.3 Biosynthesis of Neolignans;198
15.4;12.4 Concluding Remarks;200
15.5;References;201
16;Index;205