Thesis-Final 03 June 2011 pdf - Jacobs University

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Background Chapter 2 Figure 13: A simplified diagram of enzymes and major products in the synthesis of chlorogenic acid in plants. The product names appear between the arrows. Enzymes involved in this pathway are PAL:, phenylalanine ammonia lyase; C4H, cinnamate 4- hydroxylase; 4CL, 4-hydroxycinnamoyl-CoA ligase; HCT, hydroxycinnamoyl-CoA shikimate/quinate hydroxycinnamoyl transferase; HQT, hydroxycinnamoyl CoA quinate hydroxycinnamoyl transferase; C3’H, p-coumaroyl ester 3’-hydroxylase. 26
Background Chapter 2 Chlorogenic acid is a product of the phenylpropanoid biochemical pathway and the first step in the phenylpropanoid pathway involves the deamination of phenylalanine to cinnamate via the enzyme phenylalanine ammonia lyase (PAL). Phenylalanine ammonia lyase RNA levels respond to several regulatory signals, and were reported to be a main factor affecting CGA levels in transgenic systems. Synthesis of CGA from cinnamate requires four enzymes to complete two hydroxylations on the aromatic ring and a conjugation of the hydroxycinnamate and quinate moieties: cinnamate-4- hydroxylase (C4H), 4-coumaroyl-CoA ligase (4CL), coumaroyl-CoA:quinate hydroxycinnamoyl- transferase (HQT), and coumarate/coumaroylquinate-3- hydroxylase (C3H). 182,183 Metabolism of chlorogenic acids and health Dietary polyphenols when tested in animals or humans affect various physiologic and physiopathologic processes, but the exact nature of the active compounds is still unknown. Knowledge concerning the absorption of chlorogenic acid in humans is essential to evaluate possible health effects in vivo because the absorbed fraction of chlorogenic acid will enter into the blood circulation and thus can induce biological effects in the blood circulation. Furthermore, the fraction that is not absorbed will enter into the colon where it might have biological effects. Like other dietary polyphenols, chlorogenic acids are an antioxidant. In vitro, it scavenges radicals generated in the aqueous phase, 184,185 increases the resistance of LDL to lipid peroxidation 186,187,188 and inhibits DNA damage. 189,190 In vivo, when added to the diet, it inhibits chemically induced carcinogenesis of the large intestine, liver and tongue in rats and hamsters. 191,192,193,194 Caffeic acid and chlorogenic acids have antioxidant properties, illustrated by their ability to scavenge various free radicals when tested in vitro. 195,196,197,198,199 In vivo, when ingested with the diet, caffeic acid and chlorogenic acid increase the plasma antioxidant capacity, the concentrations of endogenous antioxidants such as vitamin E and the exvivo resistance of lipoproteins to oxidation. 200,201,202 Chlorogenic acids also are able to reverse the pro-oxidant effects of drugs such as paraquat. 2<strong>03</strong> Chlorogenic 27
Page 1 and 2: Synthesis of Chlorogenic Acids & Ch
Page 3 and 4: “Imagination is more important th
Page 5 and 6: Abbreviations Ac Ac 2 O AcOH MeCN C
Page 7 and 8: CONTENT Chapter 1 vi
Page 9 and 10: Content Chapter 1 Preparation of ac
Page 11 and 12: Content Chapter 1 (1S, 3R, 4R, 5R)-
Page 13 and 14: Background Chapter 2 Phenolic Phyto
Page 15 and 16: Background Chapter 2 Types of polyp
Page 17 and 18: Background Chapter 2 Stilbenes cont
Page 19 and 20: Background Chapter 2 Biosynthesis o
Page 21 and 22: Background Chapter 2 Biological act
Page 23 and 24: Background Chapter 2 terpenoids, to
Page 25 and 26: Background Chapter 2 Table 2: Bioav
Page 27 and 28: Background Chapter 2 These well kno
Page 29 and 30: Background Chapter 2 Hydroxycinnami
Page 31 and 32: Background Chapter 2 small amounts
Page 33 and 34: Background Chapter 2 Cinnamate tran
Page 35 and 36: Background Chapter 2 used in the is
Page 37: Background Chapter 2 acid is implic
Page 41 and 42: Background Chapter 2 HO O HO OH C O
Page 43 and 44: Background Chapter 2 acyl migration
Page 45 and 46: Background Chapter 2 Reported Synth
Page 47 and 48: Background Chapter 2 1-O-Cinnamoylq
Page 49 and 50: Background Chapter 2 O O O H + CinO
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Page 55 and 56: Background Chapter 2 Esterification
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Page 59 and 60: Background Chapter 2 Table 5: Chlor
Page 61 and 62: Background Chapter 2 roasting degre
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Conclusions Chapter 4 Conclusions A
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Conclusions Chapter 4 Mono-acyl chl
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Conclusions Chapter 4 The products
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Conclusions Chapter 4 Di-acyl chlor
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Conclusions Chapter 4 Poly-acyl chl
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EXPERIMENTAL Chapter 5 181
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Synthesis of starting materials Qui
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Annex Chapter 6 Acetyl ferulic acid
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Annex Chapter 6 3, 4-dimethoxycinna
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Annex Chapter 6 3, 4-O-Isopropylide
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Annex Chapter 6 1-(β, β, β-trich
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Annex Chapter 6 (1S, 3R, 4R, 5R)-1-
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Annex Chapter 6 (1R,3R,4S,5R)-1-dim
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Annex Chapter 6 (1R, 3R, 4S, 5R)-1-
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Annex Chapter 6 5- diacetylcaffeoyl
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Annex Chapter 6 5- acetyl p-coumaro
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Annex Chapter 6 5-cinnamoyl bisacet
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Annex Chapter 6 5-O-feruloylquinic
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Annex Chapter 6 5-O-dimethoxycinnam
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Annex Chapter 6 (1S,3R,4R,5R)-1-(β
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Annex Chapter 6 (1S,3R,4R,5R) 1- (
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Annex Chapter 6 (1S,3R,4R,5R)-3,4-b
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Annex Chapter 6 (1S,3R,4R,5R)-1,3-d
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Annex Chapter 6 (1S,3R,4R,5R)-1,3-b
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Annex Chapter 6 (1S,3R,4R,5R)-1,4-d
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Annex Chapter 6 Quinide tri-acetate
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Annex Chapter 6 (1S, 3R, 4R, 5R)-1,
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Annex Chapter 6 745 [M+H], 544 [M-C
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Annex Chapter 6 (C-24), 121.95 (C-3
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REFERENCES Chapter 6 253
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References Chapter 6 21 D. Strack,
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References Chapter 6 62 K. Herrmann
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References Chapter 6 104 N. Shibuya
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References Chapter 6 148 B. Möller
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References Chapter 6 187 M. Nardini
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References Chapter 6 221 M. F. Andr
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References Chapter 6 264 L. Panizzi
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References Chapter 6 303 J. Hucke,
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