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FLAVONOID FERVER

FLAVONOID FERVER. And the Charm of Chalcones. Wine and the French paradox. The French are 2.5 times less likely than Americans to die of coronary heart disease. Regular consumption of red wine is linked to reduced clumping of platelets; improved cardiovascular risk profile;

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FLAVONOID FERVER

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  1. FLAVONOID FERVER And the Charm of Chalcones

  2. Wine and the French paradox The French are 2.5 times less likely than Americans to die of coronary heart disease. Regular consumption of red wine is linked to • reduced clumping of platelets; • improved cardiovascular risk profile; • increased levels of HDL’s

  3. Structural Features of Naturally Occurring Bioflavonoids

  4. Mechanisms of Bioactivity • Flavonoids are capable of scavenging free radicals and possibly quench singlet oxygen • Many naturally occurring flavonoids are capable of chelating metals and thereby preventing them from reducing H2O2 in hydroxyl radical formation. • Flavonoids have a synergistic effect on vitamin C and appear to stabilize ascorbic acid in human tissues

  5. Plant Biosynthesis of Flavonoids

  6. Crystal Structure of Quercetin

  7. Reaction of Quercetin with Hydroxyl Radicals

  8. Citrus limon Rutin

  9. Dried peels of bitter orange tree Naringinen-7-rhamnoglucoside

  10. Buchu Diosmetin

  11. Marigold flower Rhamnetin

  12. Milk Thistle Silybin

  13. Preparation of 2’-Hydroxychalcones

  14. Preparation of Chalcones by Claisen-Schmidt Condensation

  15. Stereoselectivity of Condensation

  16. Cyclization of 2’-Hydroxychalcones to Flavanols

  17. Delocalization of p electrons in Chalcone

  18. Charge Distribution in 2’-Hydroxy-4-dimethylaminochalcone

  19. 4-Dimethylaminochalcone, 10-5M in methanol

  20. 10-4 M DMAC in acidified methanol

  21. 4-Dimethylaminochalcone

  22. Absorbances of some Chalcones in the UV and IR

  23. Features of Strong Hydrogen Bonding • The pKa of the hydrogen donor is similar to the conjugate acid of the hydrogen acceptor; • The energy barrier to proton transfer diminishes as the distance between the heteroatoms involved in hydrogen-bonding is reduced to value less than the sum of the van der Waals radii: < 255 pm for O-H-O and < 265 pm for O-H-N); • H NMR chemical shifts for participating proton is far downfield (typically in the range of 16 to 20 ppm).

  24. Crystallographic Data for2’-Hydroxy-4-dimethylaminochalcone

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