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Secondary Products. Introduction and Terpenes. Review of Primary Pathways I -Glycolysis. II – Krebs Cycle. Pyruvate  Acetyl-CoA. III – Pentose Phosphate Pathway. Secondary Products. What are secondary products? Where are they found? What do they do? Major Types of Secondary Products

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secondary products

Secondary Products

Introduction and Terpenes

secondary products1
Secondary Products
  • What are secondary products?
  • Where are they found?
  • What do they do?
  • Major Types of Secondary Products
    • Terpenes
    • Phenolics
    • Glycosides
    • Alkaloids
terpenes terpenoids
Terpenes (Terpenoids)
  • Diverse group of lipids – about 15,000 to 30,000
    • Insoluble in water
    • Synthesized from acetyl-CoA or Glycolysis intermediates
  • Derived from the union of 5-carbon isoprene units (C5H8)
    • terpenes also called isoprenes or isoprenoids
  • Called terpenoids if other elements included (especially oxygen)
isoprene molecule
Isoprene Molecule

H3C

CH-CH=CH2

H2C

t wo pathways of terpene synthesis
Two Pathways of Terpene Synthesis
  • Mevalonic Acid Pathway: 3 molecules of acetyl-CoA are joined together to form mevalonic acid
    • Mevalonic acid is a 6-carbon intermediate
    • Mevalonic acid is
      • phosphorylated with two phosphate groups - pyrophosphate (P-P)
      • decarboxylate and dehydrated to produce isopentyl pyrophosphate (isopentyl diphosphate) - IPP
      • IPP the activated building block
  • Mevalonate-Independent Pathway
    • Uses glycolysis intermediates to synthesize IPP
types of terpenes
Types of terpenes
  • Classified by number of isoprene units
    • sometimes compounds highly modified so its difficult to pick out isoprenes
  • Hemiterpenes - contain 1 isoprene unit (5-C)
  • Monoterpenes - contain 2 isoprene units (10-C)
  • Sesquiterpenes - 3 isoprenes (15-C)
  • Diterpenes - 4 isoprenes (20-C)
  • Triterpenes - 6 isoprenes (30-C)
  • Tetraterpenes - 8 isoprenes (40-C)
  • Polyterpenes - over 10 isoprenes
monoterpenes c 10
Monoterpenes: C-10
  • Many monoterpenes function as insect toxins
    • Pyrethrins – neurotoxins
    • Conifer resins – mixture of monoterpenes
    • Essential oils - many are insecticidal
    • Recent study showed that some essential oils released after the first insect attack – essential oil attracted predators to attacking insect
  • Many essential oils are also antibacterial and antifungal
  • Some essential oils attract pollinators
sesquiterpenes c 15
Sesquiterpenes: C-15
  • Strong feeding repellants to insects and mammals
  • Some antimicrobial as well
  • Often have a lactone ring
  • Gossypol in cotton responsible for insect resistance in some varieties (possible new spermicide)
  • Artemisinin produced by Artemesia annua
    • Lactone with potent anti-malarial activity
diterpenes c 20
Diterpenes: C-20
  • Toxins and feeding deterrents
  • High boiling point so not volatile essential oil - referred to as resins
  • Some diterpenes skin irritants
  • Cytotoxic lactone from Podocarpus have antileukemia activity
  • Taxol from Taxus is antimitotic - used to treat ovarian and breast cancer
triterpenes c 30
Triterpenes: C-30
  • Includes structurally diverse cmpds including steroids
    • Some important glycosides have a triterpene as the aglycone – digitalis, saponins
  • Some mimic insect hormones and interfere with development
  • Other triterpenes are antifeedants
    • Azadiractin from oil in neem tree best known