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Resins
Podophyllotoxin, Curcumin
22/9/2020 Dr Payal Rahul Dande 1
Dr PayalRahul Dande
M.Pharm,PhD
SVKM’sNMIMS,SPTMShirpurcampus
UNIT-III (6 Hours):
• Isolation, Identification and Analysis of Phytoconstituents
a) Terpenoids: Menthol, Citral, Artemisin
b) Glycosides: Glycyrhetinic acid & Rutin
c) Alkaloids: Atropine, Quinine, Reserpine, Caffeine
d) Resins: Podophyllotoxin, Curcumin
22/9/2020 Dr Payal Rahul Dande 2
Resins: Introduction
• Resins are amorphous solid or semisolid substances are regarded as the
end products of secondarymetabolism.
• They may contain volatile oil, oxygenated products of terpenes and carboxylic
acid
• Always water insoluble but mostly soluble in alcohol, volatile & fixed oil and
other non polar organic solvents.
• Physically they are found to be hard, translucent or transparent and fusible
i.e., upon heating they first get softened and ultimately melt.
• Chemically, they are complex mixtures of allied substances, like: resin acids,
resin alcohols (resinols), resinotannols, resin esters or glucoresins
22/9/2020 Dr PayalRahul Dande 3
Podophyllotoxin
Isolation, Identificationand Analysis of Phytoconstituents
22/9/2020 Dr Payal Rahul Dande 4
Podophyllotoxin - Introduction
• Podophyllotoxin is a resin found in the rhizomes of Podophyllum
hexandrum or Podophyllum emodi of the family Berberidaceae
growing in the Himalayan forest in Kashmir, Sikkim and parts of UP.
• Podophyllotoxin: 20% in American & 40% in Indian variety.
22/9/2020 Dr Payal Rahul Dande 5
22/9/2020 Dr Payal Rahul Dande 6
Podophyllotoxin
• Chemicallyit is aryltetralinlactone lignan.
• It is a toxic, polycyclic antimitoticagent
• Formula:C22H22O8
• Molar mass: 414.405 g/mol
• Melting point: 183.3 to 184 °C
• Solubility:
• Very Soluble in chloroform and pure ethanol,
• Soluble in acetone or dichloromethane;
• insoluble or sparinglysoluble in water
• Insoluble in ethyl ether
22/9/2020 Dr Payal Rahul Dande 7
Extraction & Isolation
• Podophyllum root & rhizome powder is extracted using alcohol by
percolationmethod or soxhlet method
• The percolated extract is concentrated to syrup consistency by removing
alcohol by distillationmethod
• Acidifiedusing acidifiedwater (containing2% HCl) with continuous stirring
• Allowed to stand for two hours at 5oC to precipitate podophyllum resin
(approximately 40%)
• Filter under vacuum, washed with acidified water, cooled at 5oC, dissolved
in 90% alcohol.
• Alcohol is distilledoff to get residuedried at 80oC to a constant weight
• Use preparativeTLC to purify and crystallizethe product at 0oC
22/9/2020 Dr Payal Rahul Dande 8
22/9/2020 Dr Payal Rahul Dande 9
Identification
22/9/2020 Dr Payal Rahul Dande 10
Analysis
Retention time of about 9.455 minutes
22/9/2020 Dr Payal Rahul Dande 11
Podophylllotoxin uses
• Used for its anti-tumor activity
• Used in production of semi-synthetic drug Etoposide & teniposide.
• Topical: as an antiviral treatment for genital warts.
• Traditionally/ earlier
• It is used as drastic but slow acting purgative
• Used with other purgatives to prevent gripping action
• anthelmintic
22/9/2020 Dr Payal Rahul Dande 12
Curcumin
Isolation, Identificationand Analysis of Phytoconstituents
22/9/2020 Dr Payal Rahul Dande 13
Curcumin introduction
• Curcuminis a brightyellow chemical produced by Curcumalonga plants.
• It is the principal curcuminoid of turmeric (Curcumalonga), of family, Zingiberaceae.
• It is sold as an herbal supplement, cosmetics ingredient, food flavouring, and food
colouringagent.
• Chemically, curcumin is a diarylheptanoid, belonging to the group of curcuminoids, which
are natural phenols responsible for turmeric's yellowcolor.
• It is a tautomeric compound existing in enolic form in organic solvents and in keto form in
water.
• Curcumin is an oil-soluble pigment, practically insoluble in water at acidic and neutral pH,
and soluble in alkali, soluble in ethanol (10 mg/ml), DMSO (25 mg/ml), acetic
acid, 0.1M NaOH, 10mM Na2CO3, acetone, water (< 0.1 mg/ml), and
chloroform
22/9/2020 Dr Payal Rahul Dande 14
22/9/2020 Dr Payal Rahul Dande 15
22/9/2020 Dr Payal Rahul Dande 16
22/9/2020 Dr Payal Rahul Dande 17
22/9/2020 Dr Payal Rahul Dande 18
TLC identification and estimation
• Sample : Dissolve 1mg curcumin in 1ml methanol
• Stationary phase: Silica Gel G
• Mobile phase: Chloroform: Ethanol: glacial acetic acid(94:5:1)
• Detecting agent: Observation at UV 365nm
• Rf: 0. 79
• Color: bright yellow florescent
22/9/2020 Dr Payal Rahul Dande 19
Quantitative estimation of curcumin
• Spectrophotometric method
• Spectroscopic analysis was carried out using Double beam Shimadzu
recording UV-Visible Spectrophotometer (Kyoto, Japan) model 1601
with 10 mm path length matched quartz cells was used for analytical
purpose.
• Stock solutions of curcumin containing 10µg/ml were prepared in
methanol and evaluated in UV spectrophotometer.
• Showed the peak with maximum absorbance at 421 nm.
• The method is applied to the determination of curcumin in
pharmaceutical formulations.
22/9/2020 Dr Payal Rahul Dande 20
Thank you
22/9/2020 Dr Payal Rahul Dande 21

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Resin

  • 1. Resins Podophyllotoxin, Curcumin 22/9/2020 Dr Payal Rahul Dande 1 Dr PayalRahul Dande M.Pharm,PhD SVKM’sNMIMS,SPTMShirpurcampus
  • 2. UNIT-III (6 Hours): • Isolation, Identification and Analysis of Phytoconstituents a) Terpenoids: Menthol, Citral, Artemisin b) Glycosides: Glycyrhetinic acid & Rutin c) Alkaloids: Atropine, Quinine, Reserpine, Caffeine d) Resins: Podophyllotoxin, Curcumin 22/9/2020 Dr Payal Rahul Dande 2
  • 3. Resins: Introduction • Resins are amorphous solid or semisolid substances are regarded as the end products of secondarymetabolism. • They may contain volatile oil, oxygenated products of terpenes and carboxylic acid • Always water insoluble but mostly soluble in alcohol, volatile & fixed oil and other non polar organic solvents. • Physically they are found to be hard, translucent or transparent and fusible i.e., upon heating they first get softened and ultimately melt. • Chemically, they are complex mixtures of allied substances, like: resin acids, resin alcohols (resinols), resinotannols, resin esters or glucoresins 22/9/2020 Dr PayalRahul Dande 3
  • 4. Podophyllotoxin Isolation, Identificationand Analysis of Phytoconstituents 22/9/2020 Dr Payal Rahul Dande 4
  • 5. Podophyllotoxin - Introduction • Podophyllotoxin is a resin found in the rhizomes of Podophyllum hexandrum or Podophyllum emodi of the family Berberidaceae growing in the Himalayan forest in Kashmir, Sikkim and parts of UP. • Podophyllotoxin: 20% in American & 40% in Indian variety. 22/9/2020 Dr Payal Rahul Dande 5
  • 6. 22/9/2020 Dr Payal Rahul Dande 6
  • 7. Podophyllotoxin • Chemicallyit is aryltetralinlactone lignan. • It is a toxic, polycyclic antimitoticagent • Formula:C22H22O8 • Molar mass: 414.405 g/mol • Melting point: 183.3 to 184 °C • Solubility: • Very Soluble in chloroform and pure ethanol, • Soluble in acetone or dichloromethane; • insoluble or sparinglysoluble in water • Insoluble in ethyl ether 22/9/2020 Dr Payal Rahul Dande 7
  • 8. Extraction & Isolation • Podophyllum root & rhizome powder is extracted using alcohol by percolationmethod or soxhlet method • The percolated extract is concentrated to syrup consistency by removing alcohol by distillationmethod • Acidifiedusing acidifiedwater (containing2% HCl) with continuous stirring • Allowed to stand for two hours at 5oC to precipitate podophyllum resin (approximately 40%) • Filter under vacuum, washed with acidified water, cooled at 5oC, dissolved in 90% alcohol. • Alcohol is distilledoff to get residuedried at 80oC to a constant weight • Use preparativeTLC to purify and crystallizethe product at 0oC 22/9/2020 Dr Payal Rahul Dande 8
  • 9. 22/9/2020 Dr Payal Rahul Dande 9
  • 11. Analysis Retention time of about 9.455 minutes 22/9/2020 Dr Payal Rahul Dande 11
  • 12. Podophylllotoxin uses • Used for its anti-tumor activity • Used in production of semi-synthetic drug Etoposide & teniposide. • Topical: as an antiviral treatment for genital warts. • Traditionally/ earlier • It is used as drastic but slow acting purgative • Used with other purgatives to prevent gripping action • anthelmintic 22/9/2020 Dr Payal Rahul Dande 12
  • 13. Curcumin Isolation, Identificationand Analysis of Phytoconstituents 22/9/2020 Dr Payal Rahul Dande 13
  • 14. Curcumin introduction • Curcuminis a brightyellow chemical produced by Curcumalonga plants. • It is the principal curcuminoid of turmeric (Curcumalonga), of family, Zingiberaceae. • It is sold as an herbal supplement, cosmetics ingredient, food flavouring, and food colouringagent. • Chemically, curcumin is a diarylheptanoid, belonging to the group of curcuminoids, which are natural phenols responsible for turmeric's yellowcolor. • It is a tautomeric compound existing in enolic form in organic solvents and in keto form in water. • Curcumin is an oil-soluble pigment, practically insoluble in water at acidic and neutral pH, and soluble in alkali, soluble in ethanol (10 mg/ml), DMSO (25 mg/ml), acetic acid, 0.1M NaOH, 10mM Na2CO3, acetone, water (< 0.1 mg/ml), and chloroform 22/9/2020 Dr Payal Rahul Dande 14
  • 15. 22/9/2020 Dr Payal Rahul Dande 15
  • 16. 22/9/2020 Dr Payal Rahul Dande 16
  • 17. 22/9/2020 Dr Payal Rahul Dande 17
  • 18. 22/9/2020 Dr Payal Rahul Dande 18
  • 19. TLC identification and estimation • Sample : Dissolve 1mg curcumin in 1ml methanol • Stationary phase: Silica Gel G • Mobile phase: Chloroform: Ethanol: glacial acetic acid(94:5:1) • Detecting agent: Observation at UV 365nm • Rf: 0. 79 • Color: bright yellow florescent 22/9/2020 Dr Payal Rahul Dande 19
  • 20. Quantitative estimation of curcumin • Spectrophotometric method • Spectroscopic analysis was carried out using Double beam Shimadzu recording UV-Visible Spectrophotometer (Kyoto, Japan) model 1601 with 10 mm path length matched quartz cells was used for analytical purpose. • Stock solutions of curcumin containing 10µg/ml were prepared in methanol and evaluated in UV spectrophotometer. • Showed the peak with maximum absorbance at 421 nm. • The method is applied to the determination of curcumin in pharmaceutical formulations. 22/9/2020 Dr Payal Rahul Dande 20
  • 21. Thank you 22/9/2020 Dr Payal Rahul Dande 21