CHEM 800
NATURAL PRODUCTS CHEMISTRY
Lecture Notes

3/16 - 4/4

Glucosinolates. Cyanogenic glycosides.

Phenolics


Volatile natural products

See also T.Robinson,"Organic constituents of higher plants":

Chapters 7 and 15 (glucosinolates, cyanogenic glycosides)


Simple phenolics:

C6, C6 - C1, C6 - C3

Acidity, water-solubility, complexation with metal ions, glycosides.

Structure of lignin.


Flavonoids, C6 - C3 - C6

Basic ring structure, numbering, substitution pattern.

Classes of flavonoids.

Biosynthesis:
A-ring is acetate derived; B-ring is derived from shikimate.


Isolation, separation, spectroscopic structure elucidation of flavonoids:

Spectroscopic structure elucidation of the diflavonoid bryoflavone:
MS, 1H-NMR, UV/VIS


Anthocyanins

Effect of pH, substitution pattern, complexation with AlCl3 on absorption maxima.
Bathochromic effect; auxochrome.
Compare pp.368-369 in Mann et al.


Tannins:

Acidic, astringent.

Hydrolyzable tannins and condensed tannins.


Testing for antioxidant activity of various flavonoids with DPPH (see JAFC 1997(45), 632 - 638).


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