secondary metabolites derived from shikimic acid (phenyl … · 2021. 2. 11. · the shikimic acid...
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Secondary metabolites derived from Shikimic acid (Phenyl propanoids and
Lignans)
Shikimic acid
OH
OH
HO
CO2H
SCH 511 1Dr. Solomon Derese
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Learning Objectives
• Recognize the role of shikimic acid, chorismic acid
and prephenic acid in biosynthesis.
• Recognize that cinnamic acid derivatives are
precursors to other natural products like lignans
and coumarines.
2SCH 511 Dr. Solomon Derese
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The Shikimic Acid PathwayThis pathway (unique to plants) leads to theformation of the aromatic amino acidsphenylalanine and tyrosine and to the formation ofmany other phenyl-C3 compounds(phenylpropanoids).
C C C
Phenylpropanoids
Phenyl-C3
SCH 511 3Dr. Solomon Derese
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Cleavage of the C3 side chain leads to manyphenyl-C1 compounds.
Phenyl-C1
C C C C
b-Oxidation
SCH 511 4Dr. Solomon Derese
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Biosynthesis of Shikimic Acid
The shikimate pathway begins with thecondensation of PhosphoEnolPyruvate(PEP) and D-erythrose 4-phosphategiving 3-Deoxy-D-Arabino-Heptulosonate-7-Phosphate (DAHP) in areaction catalysed by the enzymephospho-2-dehydro-3-deoxyheptonatealdolase (DAHP synthase).
SCH 511 5Dr. Solomon Derese
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DAHP
SCH 511 6Dr. Solomon Derese
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SCH 511 7Dr. Solomon Derese
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Chorismate is a key Intermediate in theSynthesis of Tryptophan, Phenylalanine, andTyrosine.
Aromatic rings are not readily available in theenvironment, even though the benzene ringis very stable. The branched pathway totryptophan, phenylalanine, and tyrosine,occurring in bacteria, fungi, and plants, is themain biological route of aromatic ringformation.
SCH 511 8Dr. Solomon Derese
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Chorismic acid
NAD+
- H2O
CO2H
OHO
4-Hydroxyphenylpyruvicacid
- CO2
- CO2
SCH 511 9Dr. Solomon Derese
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Phenylalanine Ammonia Lyase (PAL)
Tyrosine Ammonia Lyase (TAL)SCH 511 10Dr. Solomon Derese
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CoumarinsSecondary metabolites with the general formula:
It has a sweet scent, readily recognized as the scentof newly-mown hay.
Coumarins have a C6-C3skeleton, with an oxygenheterocycle as part of theC3-unit.
Coumarins owe their class name to ‘Coumarou’, thevernacular name of the tonka bean (Dipteryxodorata Willd.,Fabaceae), from which coumarinitself was isolated in 1820.SCH 511 11Dr. Solomon Derese
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O OHO
Umbeliferone
O OHO
HO
Aesculetin Herniarin
O OMeO
O OO
Psoralen
O OO
OImperatorin
Examples of Coumarins
SCH 511 12Dr. Solomon Derese
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SCH 511 Dr. Solomon Derese 13
O OCoumarin
Lactone formation
Lactone formation
Biosynthesis of Coumarins
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SCH 511 14Dr. Solomon Derese
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Lignans
Lignans are a large group of natural productscharacterized by the coupling of two C6C3units.
Lignans are a class of naturally occurringplant phenols that are derivedbiosynthetically from dimerization ofcinnamic acid.
Definition
SCH 511 15Dr. Solomon Derese
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Biosynthesis of Lignans
SCH 511 16Dr. Solomon Derese
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Radical pairing A + D;B + D; D + D, etcyield different typesof lignans.
SCH 511 17Dr. Solomon Derese
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D
D
SCH 511 18Dr. Solomon Derese
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OH
OMe
OH
HO
O
MeO
SCH 511 19Dr. Solomon Derese
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H+
OH
OMe
OH
HO
O
MeOOH
OH
OH
OMe
HO
MeO
IsolariciresinolSCH 511 20Dr. Solomon Derese
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SCH 511 21Dr. Solomon Derese