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1. This e-content has been exclusively developed for the benefit of students & is purely for the Educational and teaching purpose under Section 52(1)(i) of the Indian Copyright Act (1957) Copyright Disclaimer under section 107 of the Copyright Act 1976, allowance is made for “fair use” for purposes such as criticism, comment, news reporting, teaching, scholarship, education and research1.
2. B.PHARM. 5th SEMESTER BP504 T. PHARMACOGNOSY AND PHYTOCHEMISTRY II (Theory)UNIT-IAcetate Mevalonate PathwayDr. Nisha SharmaSchool of Pharmaceutical SciencesC.S.J.M. University, Kanpurnishasharma@csjmu.ac.in2
3. Acetate PathwayAcetate Required for synthesis of various secondary metabolites in plants, is central moleculeStarting material is acetate utilized as acetyl Co-A(active form of acetate)Various straight chain or aromatic compounds are synthesized by acetateAcetate Mevalonate Pathway Contributes 1/3rd of secondary metabolitesBiosynthesis -active building block (universal precursor) Isoprene unit (C5)- for all isoprenoids (secondary metabolites)Isopentenyl pyrophosphate (universal precursor)Dimethyl allyl pyrophosphate (universal precursor)3
4. Acetate PathwayIsopentenyl pyrophosphate & Dimethyl allyl pyrophosphate are universal precursor for synthesis of Isoprenoids i.e. terpenoids & steroidsIsoprene unit (C5H8) - responsible along with other pathways for biogenesis of anthraquinone, naphthaquinone, terpenoids, glycosides, alkaloidsOccurrence of MAP: Eukaryotes, bacteria, plants, animalsIsoprene units- Monoterpenoids: 2 isoprene units:- 10 C - menthol, geraniolSesquiterpenoids: 3units: 15 C: termeroneDiterpenoids: 4 isoprene units- 20 C: phytolOxygenated Derivatives of terpenes4
5. Acetate Mevalonate PathwayStarting material for MAP: Acetyl Co-ACombination of 2 units of Ac-CO-A- Aceto acetyl Co-AAceto acetyl Co-A + 1 more Acetyl Co-A gives rise to β-hydroxy methyl glutryl Co-A, in presence of HMG Co-A synthaseHMG Co-A- reduced to Mevalonic acid in presence of HMG Co-A reductaseSo, called as acetate mevalonate pathwayMevalonic acid- Iso Pentenyl pyrophosphate in presence of isomerase enzymes converts to Di Methyl Allyl PyroPhosphate5
6. Acetate Pathway6GlycolysisPyruvate End productAcetyl Co-ATCAAcetate mevalonate pathwayAcetate melonate pathway-mevalonic acid Malonyl Co-Aterpenes & steroidsLong chain fatty acids & polyketidesIsoprenoids Squalene SteroidsLipids, fats , waxes
7. Types of compounds synthesized from Acetate Pathway7Iso Pentenyl Pyrophosphate + Di Methyl Allyl Pyro Phosphate (active isoprene units) CONDENSESGeranyl pyro PO4 (C10)Monoterpenes-Menthol, limonene, geraniol, linalool, citralFarnesyl PP C15sesquiterpenes- termerone, zingiberene, abscisic acid, santaloneIPPC-30SqualenesteroidsTerpenoidsSolanine, diosgenin2 Geranyl GPP C-20IPPDi terpenes TaxolPoly terpenes RubberC-40TetraterpenesIPP +2GGPPGibberellinsPhytolCarotenoids, lycopene, β carotene
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9. ReferencesMedicinal Natural Products: A Biosynthetic Approach, Paul M. Dewick, 3rd Ed. 2009, John Wiley & Sons, Ltd. England . The Biosynthesis of secondary metabolites, R.B. Herbert, 1st Ed. 1981, Chapman & hall, London.Pharmacognosy, C.K. Kokate, A.P. Purohit, S.B. Gokhale, 54th Ed. 2017, Nirali Publication, New DelhiTrease and Evans Pharmacognosy, W.C. Evans, 15th Ed. Elsevier, 2002.https://www.slideshare.net9