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Secondary Products III Glycosides

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Rosaceae (Rose Family) contains cyanogenic glycoside - amygdalin. Amygdalin from apricot pits source of Laetrile. Cassava. Amygdalin. Glucosinolates ... – PowerPoint PPT presentation

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Title: Secondary Products III Glycosides


1
Secondary Products III Glycosides
2
Glycosides
  • Sugar most commonly found is glucose
  • Non-sugar molecule known as the aglycone and may
    be
  • amino acid derivatives
  • steroids
  • triterpenes

3
Glycosides
  • Most common types
  • Saponins
  • Cardiac Glycosides (Cardenolides)
  • Cyanogenic Glycosides
  • Anthraquinone Glycosides
  • Glucosinolates (sometimes not included)
  • Most glycosides function as deterrents to
    herbivores

4
Saponins
  • Terpene glycosides
  • Steroid glycosides
  • Steroid-alkaloid glycosides
  • Triterpene glycosides
  • Sapogenins
  • Properties of saponins
  • Effects of saponins on water

5
Useful saponins
  • Saponins from yam - Disocorea spp. are the source
    of steroids used for human hormones
  • Birth control pills - most synthetic but some
    still use natural hormones
  • Anti-inflammatory steroids
  • Licorice - Glycyrrhiza glabra produces saponins
    that possibly help gastric ulcers because they
    suppress prostoglandins

6
Cardiac glycosides
  • Properties
  • Distribution
  • Best known are digitoxin and digoxin from
    Digitalis purpurea (foxglove) 30 glycosides
  • Other poisonous plants with cardiac glycosides
  • Oleander - Nerium oleander - oleandrin
  • Milkweed - Asclepias spp - asclepiadin
  • Lily of the Valley - Convallaria sp.
    convallotoxin and convallarin
  • Physiological Action

7
Foxglove Digitalis purpurea
8
Digitoxin
9
Sugars in digitoxin
  • 2 molecules of digitose
  • 1 molecule of 1-acetyl digitose
  • 1 molecule of glucose

Digitose
10
Oleander
11
Oleandrin
12
Milkweeds
13
Convallaria majalis
14
Convallotoxin
15
Cyanogenic glycosides
  • Distribution
  • Most derived from 4 amino acids (phenylalanine,
    tyrosine, valine, or isoleucine) or from
    nicotinic acid
  • Cyanogenic glycosides are not toxic by themselves
  • Two enzymes involved in toxicity
  • b-glycosidase releases the sugars
  • Hydroxynitrile lyase releases HCN
  • Effects of HCN

16
Electron Transport System
17
Cyanogenic Glycosides
  • Variability
  • Cassava (Manioc esculenta) major food crop with
    cyanogenic glycosides
  • Rosaceae (Rose Family) contains cyanogenic
    glycoside - amygdalin
  • Amygdalin from apricot pits source of Laetrile

18
Cassava
19
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20
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21
Amygdalin
22
Glucosinolates
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