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2. CSIR-CENTRAL INSTITUTE OF MEDICINAL AND AROMATIC PLANT LUCKNOW, INDIA BIOSYNTHESIS OF ANDROGRAPHOLIDE IN ANDROGRAPHIS PANICULATA DR. ANAND AKHILA NISHI SRIVASTAVA EX- DEPUTY DIRECTOR, RESEARCH SCHOLAR PRINCIPAL SCIENTIST, CSIR-CIMAP CSIR, LUCKNOW,INDIA LUCKNOW, INDIA

3. ANDROGRAPHIS PANICULATA Abortifacient (can abort pregnancy Acrid (rubifacient to the skin) Analgesic (pain killer) Anti-inflammatory (reduces swelling) Antibacterial (fights bacterial activity) Antiperiodic (counteracts periodic/intermittent diseases, such as malaria) Antipyretic (fever reducer) Antithrombotic (blood clot preventative) Antiviral (inhibits viral activity) Cancerolytic (fights, even kills, cancer cells) Cardioprotective (protects heart muscles) Choleretic (alters the properties and flow of bile) Depurative (cleans and purifies the system, particularly the blood) Digestive (promotes digestion) Expectorant (promotes mucus discharge from the respiratory system) Hepatoprotective (protects the liver and gall bladder) Hypoglycemic (blood sugar reducer) Immune Enhancement (increases white cell phagocytosis) Laxative (aids bowel elimination) Sedative (a relaxing herb) Andrographolide

4. IPP AND DMAPP ARE THE BUILDING BLOCKS IN THE BIOSYNTHESIS OF TERPENOIDS Watch how these two units join ‘Head to Tail’ to form the monoterpene family IPP DMAPP

5. FOUR ISOPRENE UNITS JOIN TO FORM ANDROGRAPHOLIDE (A DITERPENE) Andrographolide

6. It is well known that all the terpenoid compounds are biosynthesised from mevalonic acid pathways. However during last 10 years an alternative pathway to mevalonate pathway has been discovered known as Deoxyxylulose pathway, commonly known as DXP. In certain bacteria, mevalonate pathway exists in the cytosol whereas the DXP in plastids. It has also been shown that MVA pathway is responsible for the biosynthesis of sesquiterpenes and sterols whereas DXP for monoterpenes, diterpenes and carotenoids. It has also been shown that both the pathways cross over in some higher plants. The reassessment of MVA and DXP in higher plants is on in many international laboratories BACKGROUND OF THE STUDY

7. MEVALONIC ACID PATHWAY THROUGH PYRUVATE –ACETATE AFTER THE BREAKDOWN OF GLOCOUSE- THIS IS BELIVED TO OCCUR IN CYTOSOL DURING THE FORMATION OF C15 & C30 COMPOUNDS

9. DXP PATHWAY OR NON-MEVALONATE PATHWAY IS BELIEVED TO BE EXISTING IN PLASTIDS AND FOLLOWED IN THE BIOSYNTHESIS OF MONO AND DITERPENES

11. Dried plant material of 13 C fed twigs of Andrographis paniculata 50 gms x 4 times Hot Soxhlet extraction with MeOH (250 ml x 4) 5 -6 hrs Concentrated under vacuum Concentrate subjected to CC (Si Gel) packed in hexane EtOAc : Hexane ( 0:100; 5:95;10:90, 15:85:; 20:80; 25:75; 30:70; 35:65; 40:60; 45:55; 50:50:; 55:45; 60:40; 65:35; 70:30; 75:25; 80:20; 85:15; 90:10; 95:5; 100:0) White compounds have been obtained in fraction EtOAc:Hexane 75:25; 80:20. After purification and washing the white solid to remove the hexane soluble part the white crystalline compound was identified as andrographolide through NMR spectra. EXTRACTION OF ANDROGRAPHOLIDE

12. POSSIBLE BIOGENETIC ROUTES TO ANDROGRAPHOLIDE

14. Precursor fed Andrographolide[1- 13 C]acetate[2- 13 C]acetate[1,6- 13 C 2 ]glucose Possible biogenetic route MVA pathwayMVA PathwayDXP Pathway Chemical shift (PPM) and Integration Ratio C-137.837.40.237.3 1.8 37.40.3 C-228.828.52.028.40.328.4 4.1 C-379.279.00.379.3 1.6 79.10.2 C-443.443.8 1.2 43.50.443.50.3 C-555.255.10.055.1 1.7 55.10.2 C-624.5 1.6 24.5 0.1 24.4 4.4 C-738.438.80.438.5 1.8 38.60.4 C-8147.9148.1 1.1 147.7 0.2 147.80.2 C-956.656.30.256.2 1.5 56.40.4 C-1038.038.5 1.9 38.30.038.30.3 C-1124.924.7 1.4 24.9 0.2 24.8 4.5 C-12146.8146.90.2146.8 1.7 146.70.3 C-13130.2130.1 1.6 130.1 0.3 130.10.2 C-1466.266.00.466.3 1.9 66.20.4 C-1575.275.0 1.3 75.1 0.2 75.1 4.3 C-16170.3170.50.7170.3 1.7 170.2 4.6 C-17109.0109.60.2109.4 1.8 109.1 4.2 C-1823.823.30.323.3 1.6 23.7 4.5 C-1964.264.10.264.4 1.5 64.10.1 C-2015.315.10.215.21.615.24.3

16. CONCLUSION 1.Biosynthesis of Andrographolide in Andragraphis paniculata primarily proceeds through DXP pathway 2.There are indications that MVA pathway is also operative 3.This indicates that there is a crosstalk between DXP and MVA pathway and the precursors like IPP do migrate through plastidial membrane from cytosol into plastids 4.The site of synthesis of andrographolide is very likely in the plastids

17. NISHI SRIVASTAVA M.Sc. (Organic chemistry) in 2007 CSIR-Research Intern in 2009-2011 in CSIR-CIMAP CSIR-Senior Research Fellow continue since 2012 CSIR-NBRI and pursuing Ph.D. Published five International paper in journal Phytochemistry (Elsevier), Journal of Plant Interaction, Journal of planar chromatography, Journal of Biomedical analysis and Journal of Phytochemistry Experinced in Biosynthetic pathways exploration of terpenoid compounds in plants and analytical method development for quantification of secondary metabolites using HPTLC, HPLC and GC- MS NISHI SRIVASTAVA

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