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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 Converts intermediates from glycolysis (phosphoenol-pyruvate) and the PPP (erythrose-4-PO4) into the aromatic amino acids: phenylalanine, tryptophan, and tyrosine See Shikimic Acid Pathway See Pathway for Phenolic Secondary Products 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 Urushiol Poison ivy urushiol Poison oak urushiol Coumarins Large group – 1300 coumarins have been identified Basic coumarin is a 2 ring structure, phenol and pyrone Many anticoagulants including Warfarin 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 Flavinoids One of the largest classes of phenolics Carbon skeleton has 15 carbons with two benzene rings connected by a 3-C bridge -C3- 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 Anthocyanins 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 Tetrahydrocannabinol