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Secondary Products III Glycosides. Glycosides. Sugar most commonly found is glucose Non-sugar molecule known as the aglycone and may be amino acid derivatives steroids triterpenes. Glycosides. Most common types Saponins Cardiac Glycosides (Cardenolides) Cyanogenic Glycosides

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glycosides
Glycosides
  • Sugar most commonly found is glucose
  • Non-sugar molecule known as the aglycone and may be
    • amino acid derivatives
    • steroids
    • triterpenes
glycosides1
Glycosides
  • Most common types
    • Saponins
    • Cardiac Glycosides (Cardenolides)
    • Cyanogenic Glycosides
    • Anthraquinone Glycosides
    • Glucosinolates (sometimes not included)
  • Most glycosides function as deterrents to herbivores
saponins
Saponins
  • Terpene glycosides
    • Steroid glycosides
    • Steroid-alkaloid glycosides
    • Triterpene glycosides
  • Sapogenins
  • Properties of saponins
  • Effects of saponins on water
useful saponins
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 - Glycyrrhizaglabra produces saponins that possibly help gastric ulcers because they suppress prostoglandins
cardiac glycosides
Cardiac glycosides
  • Properties
  • Distribution
  • Best known are digitoxin and digoxin from Digitalis purpurea (foxglove) – 30 glycosides
  • Other poisonous plants with cardiac glycosides
    • Oleander - Neriumoleander - oleandrin
    • Milkweed - Asclepias spp - asclepiadin
    • Lily of the Valley - Convallaria sp. – convallotoxin and convallarin
  • Physiological Action
slide7

Foxglove

Digitalis purpurea

sugars in digitoxin
Sugars in digitoxin
  • 2 molecules of digitose
  • 1 molecule of 1-acetyl digitose
  • 1 molecule of glucose

Digitose

cyanogenic glycosides
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
cyanogenic glycosides1
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