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Secondary Products - II

Secondary Products - II . Phenolics. Phenolics. Synthesis of Phenolics. Phenolics are synthesized by a number of different pathways Two most important: Shikimic acid pathway - more important in plants Malonic acid pathway - more important in fungi . Shikimic Acid Pathway.

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Secondary Products - II

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  1. Secondary Products - II Phenolics

  2. Phenolics

  3. Synthesis of Phenolics • Phenolics are synthesized by a number of different pathways • Two most important: • Shikimic acidpathway - more important in plants • Malonic acid pathway - more important in fungi

  4. Shikimic Acid Pathway • Converts intermediates from glycolysis (phosphoenol-pyruvate) and the PPP (erythrose-4-PO4) into the aromatic amino acids: phenylalanine, tryptophan, and tyrosine

  5. See Shikimic Acid Pathway

  6. See Pathway for Phenolic Secondary Products

  7. Simple Phenolics • Allelopathic compounds • Defense cmpds against insect herbivores and fungi • Certain phenolics (furanocoumarins) are phototoxic - not toxic till activated by sunlight (near UV-A) • Activated furanocoumarins can insert into DNA and bind to pyrimidine bases - blocks transcription and leads to cell death • Abundant in Apiaceae • Urushiol in poison ivy

  8. Urushiol Poison ivy urushiol Poison oak urushiol

  9. Coumarins • Large group – 1300 coumarins have been identified • Basic coumarin is a 2 ring structure, phenol and pyrone • Many anticoagulants including Warfarin

  10. Lignin a complex phenolic Lignin monomers • Polymer of three phenolic alochols • Different species have different ratios of these monomers • Lignin in beech has 100:70:7 of coniferyl: sinapyl: para-coumaryl

  11. Flavinoids • One of the largest classes of phenolics • Carbon skeleton has 15 carbons with two benzene rings connected by a 3-C bridge -C3-

  12. Flavinoids • Flavinoids classified into different groups based on the degree of oxidation of the 3-C bridge • Anthocyanins • Flavones • Flavonols • Isoflavones • Majority of flavinoids exist as glycosides

  13. Anthocyanins

  14. Tannins • Tannin a general name for a large group of complex phenolic substances that are capable of tanning animal hides into leather by binding collagen

  15. Tetrahydrocannabinol

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