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The Biochemistry and Medical Significance of the Flavonoids

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The Biochemistry and Medical Significance of the Flavonoids Pharmacology & Therapeutics 96 (2002) 67–202 The biochemistry and medical significance of the flavonoids Bent H. Havsteen* Department of Biochemistry, University of Kiel, Olshausenstrasse 40, D-24098 Kiel, Germany Abstract Flavonoids are plant pigments that are synthesised from phenylalanine, generally display marvelous colors known from flower petals, mostly emit brilliant fluorescence when they are excited by UV light, and are ubiquitous to green plant cells. The flavonoids are used by botanists for taxonomical classification. They regulate plant growth by inhibition of the exocytosis of the auxin indolyl acetic acid, as well as by induction of gene expression, and they influence other biological cells in numerous ways. Flavonoids inhibit or kill many bacterial strains, inhibit important viral enzymes, such as reverse transcriptase and protease, and destroy some pathogenic protozoans. Yet, their toxicity to animal cells is low. Flavonoids are major functional components of many herbal and insect preparations for medical use, e.g., propolis (bee’s glue) and honey, which have been used since ancient times. The daily intake of flavonoids with normal food, especially fruit and vegetables, is 1–2 g. Modern authorised physicians are increasing their use of pure flavonoids to treat many important common diseases, due to their proven ability to inhibit specific enzymes, to simulate some hormones and neurotransmitters, and to scavenge free radicals. D 2002 Elsevier Science Inc. All rights reserved. Keywords: Flavonoids; Benzopyrones; Heat shock proteins; Gene expression; Enzyme inhibition Abbreviations: Ab, b-amyloid; AC, adenylate cyclase; ACTH, adrenocorticotrophic hormone; AD, Alzheimer’s disease; AIDS, acquired immunodeficiency syndrome; APC, antigen-presenting cell; cAMP, cyclic AMP; CAT, chloramphenicol acetyltransferase; cGMP, cyclic GMP; CoA, coenzyme A; COX, cyclo- oxygenase; CSF, colony stimulating factor; DAG, diacylglycerol; ER, estrogen receptor; FA, fatty acid; GABA, g-aminobutyric acid; GC-MS, gas chromatography-mass spectrometry; GSH, glutathione; HIV, human immunodeficiency virus; HMG, 3-hydroxy-3-methyl-glutaryl; HSE, heat shock regulatory element; HSF, heat shock factor; HSP, heat shock protein; HTLV, human T-lymphocyte-associated virus; IAA, indolyl acetic acid; ICE, interconverting enzyme; IFN, interferon; Ig, immunoglobulin; IL, interleukin; LDL, low-density lipoprotein; MHC, major histocompatibility complex; NK-T-Ly, natural killer T-lymphocyte; NO, nitric oxide; PDE, phosphodiesterase; PG, prostaglandin; PGI2, prostacyclin; PIL, phosphatidylinositol lipase; PKC, protein kinase C; PL, phospholipase; PRR, proton relaxation rate; Pyr-P, pyridoxal phosphate; R, receptor; RA, rheumatoid arthritis; SIV, Simian immunodeficiency virus; SOD, superoxide dismutase; THF, tetrahydrofolate; TIMP, tissue inhibitor of matrix metalloproteinase; TNF, tumor necrosis factor; Tx, thromboxane; XO, xanthine oxidase. Contents 1. Preface ............................................... 69 2. Introduction ............................................ 70 3. The chemistry of flavonoids .................................... 71 3.1. Structure and nomenclature................................. 71 3.2. The oxidation-reduction potential of flavonoids ...................... 71 3.3. Acid-base properties .................................... 72 3.3.1. The tautomery of anthocyanin........................... 72 3.4. Absorption and fluorescence spectra of flavonoids ..................... 74 3.5. Optical activity of flavonoids................................ 76 3.6. Radical scavenging by flavonoids ............................. 77 3.7. Linear free-energy relationships applied to the flavonoids ................. 80 3.7.1. The nature of the problem............................. 80 3.7.2. Linear free-energy relationships .......................... 80 * Current Address: Abildgaardsvej 49, DK-2830 Virum, Denmark. Tel.: +49-0431-880-3214. E-mail address: [email protected] (B.H. Havsteen). 0163-7258/02/$ – see front matter D 2002 Elsevier Science Inc. All rights reserved. PII: S0163-7258(02)00298-X 68 B.H. Havsteen / Pharmacology & Therapeutics 96 (2002) 67–202 4. The occurrence of flavonoids ................................... 81 4.1. Distribution in nature .................................... 81 5. Identification of flavonoids .................................... 82 5.1. Magnetic resonance spectrometry of flavonoids ...................... 83 5.1.1. Introduction .................................... 83 5.1.2. Information available from proton relaxation rates ................ 83 5.1.3. The theory of pulsed nuclear magnetic resonance ................. 83 5.1.4. The measurement of relaxation times ....................... 86 5.1.5. Applications of proton resonance relaxation.................... 88 5.1.6. Concluding remarks on nuclear magnetic resonance ............... 88 5.2. Identification of flavonoids by gas chromatography-mass spectrometry .......... 89 5.2.1. Scope ....................................... 89 5.2.2. Analysis of propolis by gas chromatography-mass spectrometry ......... 89 5.3. Analysis of propolis by high performance liquid chromatography ............. 89 5.3.1. Scope ....................................... 89 5.3.2. The analytical procedure. ............................. 89 6. The biosynthesis of flavonoids................................... 90 6.1. Anabolism ......................................... 90 6.2. The genetics of flavonoids ................................. 92 7. The role of the flavonoids in plant physiology .......................... 93 7.1. Flavonoids as signals of symbiosis ............................. 95 8. The pharmacology of flavonoids in animals ............................ 95 8.1. Pharmacodynamics ..................................... 96 8.2. Acute toxicity of flavonoids ................................ 97 8.3. Long-term effects of flavonoids .............................. 97 8.4. The catabolism of flavonoids ................................ 97 9. The immunology of the flavonoids ................................ 99 9.1. The flavonoids as antigens ................................ 100 9.2. Flavonoids as immune modulators ............................ 100 10. Scavenging of free radicals by flavonoids ............................ 101 11. The electron transfer catalysis by flavonoids .......................... 103 12. The flavonoids as enzyme inhibitors............................... 104 12.1. Hydrolases ....................................... 104 12.2. Oxidoreductases..................................... 106 12.3. Kinases ......................................... 108 12.4. Isomerases ....................................... 108 12.5. Transferases ....................................... 108 12.6. Ligases and lyases ................................... 108 13. The hormone action of flavonoids ................................ 108 14. The mutagenic potential of flavonoids.............................. 108 15. The influence of the flavonoids on the sensory system ..................... 109 15.1. The olfactory system .................................. 109 15.2. The neurostimulatory effect of flavonoids ....................... 110 15.3. The analgesic effect of flavonoids ........................... 110 16. Complexes of flavonoids with heavy metal ions......................... 110 17. Medical, technical, gastronomic, and other applications of flavonoids ............. 111 17.1. Hypertension and microbleeding ............................ 112 17.2. Inflammation ...................................... 114 17.3. The effect of flavonoids on the condition of diabetes mellitus patients......... 121 17.4. Local anaesthesia by flavonoids ............................ 125 17.5. Protein-rich oedema ................................... 126 17.6. Loosening of connective tissue ............................. 127 17.7. The effect of flavonoids on allergy and asthma..................... 128 17.8. The influence of flavonoids on cancer ......................... 130 17.8.1. The biology of cancer ............................ 130 17.8.2. The treatment of cancer by flavonoids .................... 133 17.8.3. Biochemical processes of cancer influenced by flavonoids ......... 134 17.8.4. Stress response ................................ 136 17.9. The influence of flavonoids on cardiovascular diseases................. 140 17.9.1. The genetic disposition............................ 140 17.9.2. The role of flavonoids in the dietary component of cardiovascular stress . 141 B.H. Havsteen / Pharmacology & Therapeutics 96 (2002) 67–202 69 17.9.3. Flavonoids in the management of ischaemia/reperfusion damage ...... 142 17.10. The effect of flavonoids on gastrointestinal ulcers ................... 143 17.11. The effect of flavonoids on rheumatic diseases ..................... 144 17.12. Bacterial infection.................................... 145 17.13. The antiviral properties of flavonoids.......................... 147 17.14. Morbus alzheimer’s ................................... 152 17.15. Wound healing ..................................... 154 17.15.1. Cellular reactions to damage ........................ 154 17.15.2. Peroxidation of lipids by free radicals ................... 154 17.15.3. Metabolic changes caused by organic solvents ............... 156 17.15.4. Hypoxic cell damage ............................ 157 17.15.5. Tissue regeneration ............................. 158 17.15.6. The anabolism ............................... 158 17.16. Heavy metal detoxification
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