Loras College. Michael T. Wallerich Erin Dahlke Ph.D.

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1 Loras College Michael T Wallerich Erin Dahlke PhD

2 Flavonoids are a large family of polyphenolic compounds that are synthesized in plants and found in substances such as cocoa, apples, tomatoes, and grapes Over 4,000 flavonoids Known 1 all of which share a common backbone structure B 1 Breinholt et al Xenbiotica A C Flavonoid backbone

3 B A C Flavonoid Skeleton Isoflavone Flavonol Flavone Flavanone Flavanols Higdon, Jane Linus Pauling Institute at Oregon State University 005 Oregon State University June-July 009 Zhang et al Molecular Pharmaceutics 4 (007): 8-45

4 Flavonoid Flavones Isoflavone Flavanone Food Parsley, celery, hot peppers Soy Foods, Soybeans, legumes Citrus Fruits and Juices Flavonol Flavanol yellow onions, kale, broccoli, apples, berries, teas Teas, chocolate, grapes, berries, apples Daily intake ranges between 50 and 1,000 mg/day depending on diet 4 4 Mullie et alplant Foods Human Nutrition 6 (007): 9-98

5 Consumption of flavonoid-rich foods has been linked to many desirable health benefits including Antioxidant Activity Anti-inflammatory Anti-cancer Anti-allergic Decreased chances of Cardiovascular Diseases Decreased chances of Neurological Impairments Parkinson's disease/ Alzheimer's Higdon, Jane Linus Pauling Institute at Oregon State University 005 Oregon State University June-July 009

6 There are to current theories Antioxidant Theory: Flavonoids neutralize free radicals in the body via the phenolic B ring This decreased amount of free radicals is the reason for the health benfits 1 -H Cell Signaling Theory: Flavonoids have been shown inhibit or stimulant enzymes and proteins in the body depending on flavonoid concentrations Example: Protein kinase C (PKC) 1 Breinholt et al 1998 Xenobiotica Higdon, Jane Linus Pauling Institute at Oregon State University 005 Oregon State University June-July 009

7 What do we know about how flavonoids are processed by the body? 5 Flavonoid rich food is consumed, digested and metabolized in the small intestines Flavonoid is metabolized by Cytochrome P450 to form metabolites CYP450 is responsible for the metabolism of a large number of pharmaceutical and neutraceutical compounds Metabolism often results in the insertion of an OH group into a C-H bond increasing the water-solubility of the compound 5 Manach, Cet al American Journal of Clinical Nutrition 81 (005): 0-4

8 Breinholt et al 1 found that metabolism of flavonoids resulted in a change in the number and position of hydroxyl substituents on the molecule This group was the first to suggest that metabolites may have different biological activities than the parent flavonoid Kawaga et al 6 examined CYP450 mediated-metabolism of flavanone and found that the resulting metabolites belonged to three different subclasses of flavonoids Since different flavonoids classes are known to penetrate different bodily tissues and exhibit different biological activities understanding the metabolism of flavonoids may provide important keys to their biological activity When they examined the metabolism of 4 -methoxy flavanone they found metabolites belonging to only two subclasses of flavonoids 1 Breinholt et al 1998 Xenobiotica Manach, Cet al American Journal of Clinical Nutrition 81 (005): KAWAGA et al Xenobiotica 4 (004):

9 R=H R=OCH flavone flavanonol flavanone isoflavone

10

11 We are interested primarily in the - phenyl shift

12 Conversion of flavanone to isoflavone is interesting for several reasons! Why would a, phenyl shift occur when both the starting and the ending radical are secondary?

13 One possibly reason is that after the phenyl shift occurs we can observe a keto-enol tautomerization which puts the A and B rings in conjugation with each other 4 Keto Form 4 OH Enol Form

14 Why is the phenyl shift only observed when R = H and not when R = OCH?

15 To answer this we propose to examine the energetics of the phenyl transfer for a variety of electron withdrawing and electron donating groups?? To Reactant Intermediate Product Electron Withdrawing NO CN Cl H CH OCH OH Electron Donating

16 Using a series of substituents we have calculated the energy of reactant, product, and intermediate for the, phenyl shift and the energy of reaction for the enol-keto tautermerization All structures were optimized with two levels of theory ublyp/6-1g* ublyp/6-11g* All calculations were carried out using Gaussian 0

17 Energy (kcal per mole) Reactant 9 Energies? 4 Keto Form Energies from Reactant to Keto Form Small ublyp/6-1g* Basis Set ublyp/6-11g* Big Basis Set 1 0 NO CN Cl H CH OCH OH Substituent Groups

18 Energy kcal per mole Reactant Energies? Enol Form Energies from Reactant to Enol Form asdf ublyp/6-1g* Big ublyp/6-11g* Basis Set OH NO CN Cl H CH OCH OH Substituent Groups

19 Keto Form 4 Reactants 4 Enol Form OH Products Small Big NO CN Cl H CH OCH OH 05E E E E E+05 61E E E+05 1E+06 89E+0 111E+06 87E+0 754E E+04

20 Enol vs Keto Enol form is much more stable for all substituents Equilibrium constant shows that the equilibrium lies far toward the enol side All spontaneous at body temperature Substituent Effects Need to optimize the rest of the intermediate structures and also find the transition states before we can understand the results

21 Bernard and Arlene Gillis Loras College Minnesota Supercomputing Institute Midwest Undergraduate Computational Chemistry Consortium (MUC)

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