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Annona squamosa as botanical pesticide

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Annona squamosa as botanical pesticide;
Annonaceous acetogenins; annonin/squamocin;
Advancement in botanical research;
Structure activity relationship of squamocin/annonin; Chemistry and mode of action of squamocin/annonin

Published in: Education

Annona squamosa as botanical pesticide

  1. 1. Term Paper Presentation AC 602 Advancement in botanical research with reference to Annona squamosa Indian Agricultural Research Institute, New Delhi Prithusayak Mondal Roll No. 10064
  2. 2. Introduction • Importance of botanical pesticides • Current botanicals (Neem, rotenone, pyrethrum, nicotine & essential oils etc.) • Potential new botanical pesticide – Squamocin (Anonin) from the plant Annona squamosa Indian Agricultural Research Institute, New Delhi
  3. 3. Plant Profile Scientific Name: Annona squamosa Linn. Kingdom Plantae – Plants Subkingdom Tracheobionta – Vascular plants Superdivision Spermatophyta – Seed plants Division Magnoliophyta – Flowering plants Class Magnoliopsida – Dicotyledons Subclass Magnoliidae Order Magnoliales Family Annonaceae – Custard-apple family Genus Annona Species squamosa – Sugar apple Indian Agricultural Research Institute, New Delhi
  4. 4. Properties Indian Agricultural Research Institute, New Delhi Plant parts Use Bark Prevention of diarrhoea Root Treatment of dysentry Leaf Cold remedy, urine purification, treatment of hysteria Fruit Haematinic, cooling, sedative, stimulant, expectorant & maturant tonic; treatment of anaemia & burning sensation; making of ice cream & milk beverages Seed Abortifacient & pesticidal activity Antifeedant, insecticidal, antidiabetic, anti-tumour, anticancer, antibacterial & antiviral activity (Pandey et al., 2011)
  5. 5. Chemical constituents • The plant is reported to contain glycoside, alkaloids, saponins, flavonoids, tannins, carbohydrates, proteins, phenolic compounds, phytosterols, amino acids (Pandey et al., 2011) • The diterpenoid alkaloid atisine is the main component of the root • Annonaceous acetogenins – Botanical pesticides Indian Agricultural Research Institute, New Delhi
  6. 6. Preparation of Extract • Shade drying of leaves & homogenization to coarse powder • Sohhlet extraction using following solvents: 1) Petroleum ether (40-60°C), 2) Chloroform, 3) Ethylacetate, 4) Acetone, 5) Methanol • Concentration of extracts using rotary evaporator at 40-50C & drying Percentage practical yield of petroleum ether (40-60oC), chloroform, ethyl acetate, acetone and methanolic extracts were found to be 3.85, 2.33, 2.39, 1.2, 7.07 % w/w respectively Indian Agricultural Research Institute, New Delhi Agarwal et al., 2012
  7. 7. Preliminary phytochemical screening Indian Agricultural Research Institute, New Delhi
  8. 8. HPTLC Study Indian Agricultural Research Institute, New Delhi
  9. 9. Annonaceous Acetogenins • Acetogenins have gained much attention recently, because of its wide range of bioactive spectra • Series of C-35/C-37 natural products derived from C-32/ C-34 fatty acids that are combined with a 2-propanol unit • Characterized by a long aliphatic chain bearing a terminal methyl-substituted α,β-unsaturated γ-lactone ring (or ketolactone ring), with 1,2 or 3 THF rings located along the hydrocarbon chain and a number of oxygenated moities (hydroxyls, acetoxyls, ketones, epoxides) &/or double bonds Indian Agricultural Research Institute, New Delhi
  10. 10. Acetogenins Extraction Ground Annona squamosa seeds AcOEt Indian Agricultural Research Institute, New Delhi (2 kg) 1) Petroleum ether 2) Partition between petrolem ether & aquousmethanol Methanol layer Residue Petroleum ether Crude acetogenin fraction layer Silica gel chromatography CHCl3/ AcOEt=2:1 to AcOEt/ MeOH= 20:1 Araya et al., 2004 Fr. 1 2 3 4 5 6 7 8 9 10
  11. 11. Structures of Acetogenins R1=R2=R4=H, R3=OH: Squamocin R1=R2=R3=H, R4=OH: Squamocin-C R1=OH, R2=R3=R4=H: Squamocin-G R1=R2=R3=R4=H: Squamocin-L R1=R4=H,R2=R3=OH: Squamocin-O1,-O2 R 4 R 3 O H O O O O H R 2 R 1 O 2 4 1 5 3 7 R1=R2=H, R3=OH: Squamocin-D R1=R3=H, R2=OH: Squamocin-F R1=OH, R2=R3=H: Squamocin-H R1=R2=R3=H,: Squamocin-M R3 O O O OH R2 R1 O OH 24 15 37 Indian Agricultural Research Institute, New Delhi
  12. 12. O O Squamocin-N Squamosten-A O OH O 24 15 37 OH O O O H O H O H O O H 2 3 1 5 3 7 Structures of Acetogenins … Indian Agricultural Research Institute, New Delhi
  13. 13. R=OH: Squamocin-B R=H: Squamocin-J R=OH: Squamocin-E R=H: Squamocin-K O O O H 2 2 1 3 Squamocin-I O H O O 3 5 O O 2 2 1 3 O O 3 5 R O H O H O O 2 2 1 3 O O 3 5 O H O H R Structures of Acetogenins … Indian Agricultural Research Institute, New Delhi
  14. 14. Structures of Acetogenins … 24 O O R1=OH: Squamostatin-C R1=H: Squamostatin-E O O OH OH OH R1 R2 19 12 37 R1=H, R2=OH: Squamostatin-A R1=OH, R2=H: Squamostatin-B R1=R2=H: Squamostatin-D 24 O O O O OH OH OH R1 19 12 37 H O O O 15 18 Squamostanal-A Indian Agricultural Research Institute, New Delhi
  15. 15. Structural Features The fundamental structural features of acetogenins are: (1) Having hydrocarbon chain, of C35 or C37 in length (2) 1~3 tetrahydrofuran rings are present (3) One γ-lactone is present at an end of hydrocarbon chain (4) 2~8 hydroxyl groups (rarely carbonyl or acetoxy group) are present Indian Agricultural Research Institute, New Delhi
  16. 16. Classification of Annonaceous Acetogenins Indian Agricultural Research Institute, New Delhi
  17. 17. Structure Activity Relationship (1) Generally, intensity of the bioactivity is (A) type (adjacent bis- THF) > (B) type (non adjacent bis-THF) > (C) type (mono-THF) > (D) type (non-THF) (2) γ-Lactone is crucial for activity (3) If all other structural features are identical, C35 acetogenins are more potent than the C37 acetogenins (4) Thirteen carbons space between the OH-flanked THF and γ- lactone is optimum for activity (5) Three hydroxyl groups, two flanking the THF ring(s) and another somewhere in the long hydrocarbon chain provide both the optimal position and polarity needed for the most potent activity, and for tetra-hydroxylated acetogenins the activity drops drastically Indian Agricultural Research Institute, New Delhi Alali et al., 1999
  18. 18. Structure Activity Relationship … (6) Neither the 4-OH group nor the 10-OH group is essential for activity (7) A ketone instead of a hydroxyl functional group decreases the activity (8) Derivatives (acetates, chloride etc.) decrease the activity (9) Ketolactone acetogenins are usually less active and more selective than their parent compounds (10) The THP ring compounds are as active as the THF compounds and have the same mechanism of action Indian Agricultural Research Institute, New Delhi Alali et al., 1999
  19. 19. Commercial Product ANOSOM® It is a biological insecticide based on botanical extract of Annona squamosa (Custard Apple / Seethaphal). ANOSOM® contains squamocin (annonin) as active ingredient and is formulated as 1% Emulsifiable Concentrate (10,000 ppm). ANOSOM® is non phytotoxic and not toxic to higher animals. Mode of Action Annonaceous acetogenins present in ANOSOM® have pesticidal and/or insect antifeedant properties. Target Pests Helicoverpa arimigera, Helicoverpa zea, Spodoptera litura, Spodoptera exigua, Earias spp. , Achaea janata, Nephotettix virescens, Bunch caterpillar, Green Leaf Hopper, Leaf Folder, Army worm, Cut Worm. Indian Agricultural Research Institute, New Delhi
  20. 20. Commercial Product … Crops ANOSOM® is suitable for application on cereals, millets, pulses, oilseeds, fibre crops, sugar crops, forage crops, plantation crops, vegetables, fruits, spices, flowers, medicinal crops, aromatic crops, orchards and ornamentals. Method of Application Foliar application : Mix ANOSOM® @ 2ml/ L of water and spray on crop canopy. The spray volume depends upon the crop canopy. It is recommended that BioPesticides are sprayed in early hours of morning or late afternoon for better results. UV radiation in peak sunny hours of the day may reduce the bio efficacy of BioPesticides. Shelf Life It is stable for a period of 24 months from the date of manufacturing. Indian Agricultural Research Institute, New Delhi
  21. 21. Mode of Action • They are potent inhibitors of NADH : ubiquinone oxidoreductase, which is an essential enzyme in complex I of the electron transport system (ETS) which eventually leads to oxidative phosphorylation in mitochondria (Lewis et al., 1993). • They act directly at the ubiquinone catalytic site(s) within complex 1 and in microbial glucose dehydrogenase (Friedrich et al., 1994). • They also inhibit the ubiquinone-linked NADH oxidase that is peculiar to the plasma membranes of cancerous cells and functions to permit cytosolic phosphorylation (substrate level phosphorylation) by restoration of NAD levels. Thus, the end result of both of these mechanisms is ATP deprivation (Morre et al., 1995). Indian Agricultural Research Institute, New Delhi
  22. 22. Indian Agricultural Research Institute, New Delhi

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