Table Of ContentBIOCHEMICAL TARGETS OF
PLANT BIOACTIVE COMPOUNDS
A pharmacological reference guide to
sites of action and biological effects
GIDEON POLYA
CRC PRESS
Boca Raton London New York Washington, D.C.
Library of Congress Cataloging-in-Publication Data
Polya, Gideon Maxwell.
Biochemical targets of plant bioactive compounds : a pharmacological reference
guide to sites of action and biological effects 1 Gideon Polya.
p. cm.
Includes bibliographical references and index.
ISBN 0-41 5-30829-1
1. Materia medica, Vegetable-Handbooks,
manuals, etc. 2. Botanical
chemistry-Handbooks,
manuals, etc. 3. Plant products-Handbooks,
manuals, etc.
4. Pharmacology-Handbooks,
manuals, etc. 5. Plants-Metabolism-Handbooks,
manuals, etc. I. Title.
RS164 .P766
2003
61 5l.32-dc21
2002155281
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International Standard Book Number 0-41 5-30829- 1
Library of Congress Card Number 2002 15528 1
Printed in the United States of America
2 3 4 5 6 7 8 9 0
Printed on acid-free paper
Contents
List of tables
Preface
1 Plant defensive compounds and their molecular targets
I. I
Introduction I
1.2
Organization and scope ofthe book 2
1.3 Descr$tion of the tables 3
1.4
Using the tables 6
1.5
The structural diversiiy of plant defensive compounds 6
1.6 Plant alkaloids 8
1.7 Plantphenolics 21
1.8
Plant te9enes 33
1.9
Other plant compounds 44
2 Biochemistry - the chemistry of life
2.1
Introduction - water-based l$
5 2
2.2
Protein structure 5 3
2.3
Engmes and ligand-binding proteins 5 8
2.4 Metabolic strategies 66
2.5 Inhibition of biochemical processes by plant defensiue compounds 85
3 Neurotransmitter- and hormone-gated ion channels
3.1 Introduction - electrical signalling in excitable cells 86
3.2 Ionotropic neurotransmitter receptors - neurotransmitter-gatedzon channels 88
3.3 Structure and function of ionotropic receptors 88
4 Ion pumps, ligand- and voltage-gated ion channels
4.1 Introduction 123
4.2 Ion pumps 123
4.3
Voltage-gated Nui channels 125
4.4
Ligand-regulated and voltage-gated K'+ channels 126
4.5
Voltage-gated Ca"
channels 126
vi Contents
4.6
Ligand-gated Ca"
channels 126
4.7
Chloride transport and voltage-regulated chloride channels 127
5 Plasma membrane G protein-coupled receptors
5.1
Introduction - signalling via heterotrimeric Gproteins 157
5.2
G protein-coupled hormone and neurotransnzitter receptors 158
5.3
Hormones and neurotransmitters acting via G protein-coupled receptors 159
5.4
Activation of spec$c G protein-coupled receptors 160
5.5
Leucocyte and inzamnzation-related G protein-linked receptors 162
5.6
Other G protein-coupled receptors 164
6 Neurotransmitter transporters and converters
6.1
Introduction 231
6.2
Synthesis of neurotransmitters 232
6.3
Release of neurotransmittersjonz synaptic vesicles 233
6.4
Re-uptake of neurotransnzitters into neurons and synaptic vesicles 233
6.5
Neurotransmitter degradation 233
7 Cyclic nucleotide-, ca2+ - and nitric oxide-based signalling
7.1
Introduction 253
7.2
~ a " and calmodulin-dependent engymes 254
7.3
A d ~ y i y l cyclase 255
7.4
Manbrane-bound and soluble guanyiyl cyclases 255
7.5
Nitric oxide synthesis 256
7.6
Cyclic AMP- and cyclic GMP-dependentprotein kinases 257
7.7
Protein kinase honzologies and phosphoprotein phosphatases 257
7.8
Cyclic nucleotide phosphodiesterases 258
8 Signal-regulated protein kinases
Introduction 295
Cyclic AMP-dependent protein kinase 296
Cyclic GMP-dependent protein kinase 29 7
Protein kinase C 298
Ca2+ -calnzodulin-dependent protein kinases 298
AMP-dependent protein kinase 299
Receptor !yrosine kinases 300
Protein kinase B 301
Cytokine activation oftheJAK'/STATpathw(/~ 302
Cell cycle control 303
Receptor serine/threonine kinases 303
Other protein kinases 3 0 3
Phosphoprotein phosphatases 304
9 Gene expression, cell division and apoptosis
9.1
Introduction 339
9.2
Regulation of gene expression in prokaryotes 339
9.3
Regulation of transcr$tion in eukaryotes 340
9.4
M A processing and translation 342
9.5
Control of translation 342
9.6
Protein processing and post-translational mody5cation 343
9.7
Protein targeting 343
9.8
Cell division and apoptosis 344
9.9
HIVI infection and HIVI replication 345
9.10
Plant compounds intefering with gene expression 345
Contents vii
339
10 Taste and smell perception, pheromones and semiochemicals
10.1
Introduction 396
1 0.2
Sweet taste receptors 39 7
10.3
Bitter taste receptors 397
10.4
Saliy taste perception 398
10.5
Sour taste perception 398
10.6
Umami jplutamate taste perception) 398
10.7
Odorant perception 398
10.8
Animal pheronzones and other animal bioactives produced by plants 399
10.9
Other plant senziochemicals affecting aninzal behaviour 399
10.10 Odoriferous animal metabolites of ingestedplant compounds 399
11 Agonists and antagonists of cytosolic hormone receptors
11.1
Introduction 452
11.2
Steroid hormones 452
11.3
Non-steroid cytosolic hormone receptor ligands 453
11.4
Plant bioactives affecting cytosolic receptor-mediated signalling 454
12 Polynucleotides, polysaccharides, phospholipids and membranes
487
12.1
Introduction 487
12.2
Po~ynucleotides 488
12.3
Poiysaccharides and 01ip.osaccharides 489
12.4
Phosphol$ids and membranes 490
13 Inhibitors of digestion and metabolism
13.1
Introduction 51 7
13.2
Giycohydrolases 51 7
13.3
Proteases 518
13.4
Giyco&sis and tricarboxylic acid cycle
522
13.5
Mitochondria1 electron transport and oxidative phospho~ylation 522
13.6
Gluconeogenesis 523
13.7
Solute translocation 524
...
viii Contents
14 Anti-inflammatory, antioxidant and antidiabetic plant compounds
14.1
Introduction 595
14.2 Adhesion and movement of inzammatocy leucocytes 596
14.3
Chemokines 5 9 6
14.4 Phagocytosis 597
14.5
Kinins, ~ytokines, platelet activating factor and eicosanoids 598
14.6
Plant-derived anti-inJamnzatory conqounds 599
14.7
Diabetes nzellitus and plant antidiabetic compounds 599
14.8 Summary 601
Appendix: structures of key parent and representative compounds
Bibliography
Compound index
Plant genus index
Plant common names index
Subject index
Abbreviations
Tables
Nicotinic acetylcholine receptor agorlists and antagonists
Iorlotropic y-aminobutyric acid and benzodiazepirle receptors
Iorlotropic glutamate, glycirle and serotonin receptors
Sigma and vanilloid receptors
Ca'+-A~Pase, H f , K+-ATPase and Naf, Kf -ATPase
Voltage-gated Na+ channel
Ligand- and voltage-gated K+ channels
Voltage- and ligand-gated Ca2+ channels and ~
a
+
/Ca2+ antiporter
CFTR, voltage-gated C 1 channels and Naf -K+-'LC1 co-transporter
Adenosine receptors
Muscarinic acetylcholirle receptor
Adrenergic receptors
Dopamine receptors
Metabotropic GABA(B)-, glutamate- and serotonin-receptors
Opiate receptors
Leucocyte- and inflammation-related G protein-coupled receptors
Other G protein-linked receptors
G protein-interacting plant compounds
Synthesis of rleurotransmitters
Release of neurotransmitters from syrlaptic vesicles
Re-uptake of neurotransmitters into neurons and synaptic vesicles
Acetylcholinesterase
Morloamirle oxidase
Degradation of other neurotransmitters
Calmodulirl
Adenylyl cyclase and guanylyl cyclase
Nitric oxide synthesis
Cyclic nucleotide phosphodiesterases
Eukaryote protein kirlases
Activation of protein kirlase C by ~lant-derived phorbol esters
Receptor tyrosine kinase-mediated signalling
Phosphatidylirlositol 3-kinase
Phosphoproteirl phosphatases
Ribosome-inactivating polynucleotide aminoglycosidases
Protein synthesis
x Tables
DNA-dependent RNA and DNA synthesis and topoisomerases
Dihydrofolate reductase and thymidylate synthetase
HIV- 1 integrase and HIV- 1 reverse transcriptase
Actin, histone acetylase, histone deacetylase, cell division and tubulin
Apoptosis-inducing plant compounds
Sweet plant compounds
Bitter plant compounds
Sour (acid) tasting plant compounds
Odorant plant compounds
Animal pheromones and defensive agents occurring in plants
Some further plant-derived semiochemicals
Odoriferous human products of ingested plant compounds
Agonists and antagonists of cytosolic steroid hormone receptors
Cytosolic non-steroid hormone receptor agonists and antagonists
Polynucleotide-binding compounds
Lectins and polysaccharide hydrolases
Non-protein plant compounds permeabilizing membranes
Plant proteins directly or indirectly perturbing membranes
Inhibition of glycosidases by plant non-protein compounds
Plant a-amylase inhibitor (aAI) proteins
Plant polygalacturonase-inhibiting proteins
Inhibition of proteases by plant non-protein compounds
Inhibition of proteases by plant proteins
Oxidative phosphorylation and photophosphorylation
Multidrug resistance, glucose and other transporters
Various enzymes
Plant lipoxygenase and cyclooxygenase inhibitors
Antioxidant free radical scavengers
Pro-oxidant compounds
Antioxidant enzyme induction and pro-inflammatory blockage
Aldose reductase and aldehyde reductase inhibitors
Plant compounds with hypoglycaemic, antidiabetic and/or insulinotropic
effects
