Industrial production of phytoconstituents, it is a part of an pharmacy syllabus, in this slide the content of syllabus is given in short and easy language.
Thanks you
Isolation, Identification and Analysis of PhytoconstituentsDr. Siddhi Upadhyay
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
Isolation, Identification and Analysis of PhytoconstituentsDr. Siddhi Upadhyay
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
Unit II Introduction to secondary metabolite
Steroids, Cardiac Glycosides & Triterpenoids:
Liquorice, Dioscorea, Digitalis
For video lecture suscribe youtube channel snehal chakorkar.
Unit I Metabolic pathways in
higher plants & their determination
Pharmacognosy & Phytochemistry II
B. Pharm. Vth Semester
Biosynthetic Pathways
Metabolic pathways
Extraction, isolation and structure elucidation of lignans(podophyllotoxin)Mohammad Khalid
Extraction, isolation and structure elucidation of- Lignans(Podophyllotoxin)
Introduction
Extraction and Isolation
Identification test
Sructure elucidation of Podophyllotoxin
Adverse Effects
Unit II Introduction to secondary metabolite
Steroids, Cardiac Glycosides & Triterpenoids:
Liquorice, Dioscorea, Digitalis
For video lecture suscribe youtube channel snehal chakorkar.
Unit I Metabolic pathways in
higher plants & their determination
Pharmacognosy & Phytochemistry II
B. Pharm. Vth Semester
Biosynthetic Pathways
Metabolic pathways
Extraction, isolation and structure elucidation of lignans(podophyllotoxin)Mohammad Khalid
Extraction, isolation and structure elucidation of- Lignans(Podophyllotoxin)
Introduction
Extraction and Isolation
Identification test
Sructure elucidation of Podophyllotoxin
Adverse Effects
Active constituent of Swertia chirata and Trigonella foenum graccum used in D...krishnapriyakr26
Synonyms : Chirayata, East Indian Balmony
Biological source : Chirata is the entire dried plant of Swertia chirata Linn.
Family : Gentianaceae
Propagation : Seeds
Geographical source : Chirata is found in India, Nepal and Bhutan at an altitude of 1200-1500 m.
Morphology : It is an erect annual herb, 60-125cm tall, stem robust, branching, cylindrical below and four- angled upwards.
Leaves- Ovate, broadly lanceoate, cordate at base
Flowers-Numerous very small greenish yellow in colour.
Fruits-Minutely pointed capsules.
Seeds-Smooth and many angled.
Chemical constituents
Swertia chirata mainly consisting of ;
Xanthones
Seccoirridoid glycosides
Flavanoids
Saponins
Lignans
Alkaloids
Terpenoids
Xanthones
Xanthone was isolated from the hexane fraction of the Swertia chirata plant and identified as 1,8-dihydroxy-3,5-dimethoxyxanthone (Swerchirin).
Swerchirin
Swerchirin is a member of the class of xanthones that is the 5-O-methyl derivative of bellidifolin.
Isolated from Swertia chirayita, it exhibits hypoglycemic activity.
It is a member of xanthones, an aromatic ether and a member of phenols.
Molecular formula C15H12O6.
Mangiferin
Aqueous extract of Swertia chirata has antidiabetic activity and is probably due to the active principle mangiferin.
Present in the stem of the swertia chirata.
It is a C-glycosyl compound and a member of xanthones.
Medicinal uses
Swertia chirata is used as:
Bitter tonic
Carminative, Laxative
Anti-pyretic, Febrifuge
Anti-periodic
Anti-inflammatory
Stomachic, and anti-helmintic.
It is used in treating piles, skin diseases, ulcers, and diabetes.
TRIGONELLA FOENUM GRAECUM
Synonym: Methi or fenugreek
Biological Source :Fenugreek consists of dried seeds of Trigonella foenum graecum.
Family : Fabaceae
Geographical Source: Plant grows wide in Northern India and is cultivated as a crop throughout India. It is also cultivated in southern and eastern Europe, Pakistan, France, Morocco And Egypt.
Trigonelline
Trigonelline an alkaloid with potential antidiabetic activity.
Trigonelline is a natural quaternary alkaloid found in the seeds of
fenugreek
It is a methylbetaine derivative of nicotinic acid
Gentianine
Gentianine is a pyridine-derived alkaloid.
Molecular formula C10H9NO2.
IUPAC name is 5-Ethenyl-3,4-dihydropyrano[3,4-c]pyridin-1-one.
Gentianine is a metabolite of gentiopicroside and swertiamarin.
It is a crystalline solid with a melting point of 82-83 °C.
It is a base that forms salts, such as the hydrochloride salt.
Antidiabetic effect of gentianine by regulating the gene expression of PPAR-ɤ, GLUT-4 and adiponectin
4-Hydroxyisoleucine
It is a Natural Nonproteinogenic amino acid present in
T.foenum graecum seeds.
4-OH is posses insulinotropic biological activity.
Fenugreek has different pharmacological attributes such as a,
Hypoglycemic
Hypercholesterolemia
Gastro protective
Chemo-preventive
Anti-oxidant
Laxative
Appetite stimulation
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Biological screening of herbal drugs: Introduction and Need for
Phyto-Pharmacological Screening, New Strategies for evaluating
Natural Products, In vitro evaluation techniques for Antioxidants, Antimicrobial and Anticancer drugs. In vivo evaluation techniques
for Anti-inflammatory, Antiulcer, Anticancer, Wound healing, Antidiabetic, Hepatoprotective, Cardio protective, Diuretics and
Antifertility, Toxicity studies as per OECD guidelines
10. PRODUCTION AND UTILIZATION OF solasodine
Solasodine is obtained from the whole plant. Solanum xanthocarpum
and dried full growth berries of Solanum khasianum.
Family: Solanaceae.
ISOLATION OF SOLSODINE BY TWO METHODS METHOD 1 B.
METHOD 2
METHOD. 1
• Dried berries is powdered
• Defatted is extracted with ethanol
• Resultant is filtered , Concentrated & Treat with HCl & Reflux
Extract is made alkaline by ammonia
• Reflux for 1 hr, Filter it, Dry and wash Residue, Mix in chloroform
Evaporate solvent Solasodine , solid residue is obtained.
11. METHOD. 2
• Powdered drug + ethanol, Soxhlation 6 hrs.
• Solvent distilled off, Concentrated to syrupy mass
• Add 5 ml HCl , Boil . Reflux for 2 hr
• Cool it & Filter… Residue + Boil water…Adjust pH-9 by NH
3 (10%)
• Boil under reflux for 2 hrs, Cool & Filter Dry Ppt Solasodine,
solid residue is obtained.
UTILIZATION OF SOLASODINE Used as a precursor for
steroidal synthesis. It is first converted to 16-
dehydropregnalone acetate which acts as a precursor for
steroidal synthesis like Corticosteroids, Pregnane Used in
synthesis of Sex hormones and Oral contraceptives. Shows
Antispermatogenic Activity Used as Hypocholestremic Agent
Used as Antiatherosclerotic Agent .
12. Identification test:
1. Solasodine+ chloroform+Antimony trichloride – Dark red colour
2. Solasodine+ Formaldyhyde+H2SO4 – Dark red –violet colour
TLC:
Adsorbant : Silica gel G
Solvent system: n-hexane: methanol: acetone(8:1:1)
Detection: Cerium sulphate-H2SO4, heat at 110°C.
HPLC:
Method : Isocratic
Stationary phase: C18
Mobile phase: Methanol : Tris buffer 0.01M (pH 7.0)
13. PRODUCTION AND UTILIZATION OF diosgenin
Diosgenin is obtained from the dried tubers of various species of
Dioscorea . Dioscorea deltoida, Dioscorea prazeri, Dioscorea
floribunda . family Dioscoreaceae.
ISOLATION OF DIOSGENIN
• Tubers collected, washed, dried extracted with hot water or 90%
ethanol for 6 hrs
• alcoholic extract concentrated under vacuum, Filter it, filterate +
solvent ether or lead acetate solution
• hydrolysis by acid, extracted with pet. Ether
• Evaporate solvent diosgenin collected, dried and packed .
14. UTILIZATION OF DIOSGENIN
Used as a precursor for steroidal synthesis. It is first converted to 16
dehydropregnalone acetate which acts as a precursor for steroidal
synthesis like Corticosteroids, Pregnane Used in synthesis of Sex
hormones and Oral contraceptives. In treatment of Rheumatism.
• Identification test:
1. Libermann test
2. Libermann-Burchard test
3. Salkowski reaction
• TLC:
• Adsorbant : Silica gel G
• Solvent system: Tolune: Ethyl acetate(7:3)
• Detection: Anysaldehyde-H2SO4, heat
at 110°C.
15. Digitalis
Digitalis purpurea leaves (foxglove)
Digitalis lanata leaves – white flowers
Scrophulariaceae
Active compounds: Cardiac glycosides:
Digitoxine, Digoxin
17. • Identification test:
1. Kedde test – Bluish to purple colour
2. Baljet reagent – Yellow, orange to deep red colour
3. Keller-killani test for digitoxose sugar – Initially red brown
layer changes to blue green.
4. Legal test (Cardenolides) – Pink or red colour
TLC/HPTLC:
Stationary phase: Silica gel 60 HPTLC DIOL Plate,
Mobile phase: Ethyl acetate/ ammonia solution 25%
Detection: MnCl3 - H2SO4 heat at 110°C.
18. PRODUCTION AND UTILIZATION OF podophyllotoxin
It is obtained from the dried rhizomes and root of Podophyllum
hexandrum Family: Berberidaceae
ISOLATION OF PODOPHYLLOTOXIN DRIED RHIZOME
• Powder extract with ethanol soxhlation, distillation, concentrate to
syrupy mass.
• add (HCL + H2O) cool at 5°c
• allowed to stand for 2 hrs, filter under vacuum
• wash residue with acidified water, cool below 5 °C
• residue + hot alcohol (90%) filter & evaporate
• dry residue to constant weight at 80 °C.
19. UTILIZATION OF PODOPHYLLOTOXIN: Potent Anti tumor agent
Used in treatment of Cancer, antiproliferative agent.
Chemical test: T.S.+ 50% H2SO4 – Violet blue colouration
TLC/HPTLC:
Stationary phase: Silica gel G, Fig.: Podophyllotoxin
Mobile phase: Cloroform: methanol (25:1)
Detection: Methanol - H2SO4 heat at 110°C
• HPLC:
• Method : Isocratic
• Stationary phase: C18
• Mobile phase: Acetonitril:water:Methanol (37: 58: 5)
• Detection: UV Visible 280nm
20. Andrographis(Kalmegh)
• Andrographolide is a labdane diterpenoid that has been
isolated from the stem and leaves of Andrographis
paniculata.Andrographolide is an extremely bitter
substance.
• Andrographolide has been studied for its effects on cell
signaling, immunomodulation, and stroke. Study has shown
that andrographlide may bind to a spectrum of protein
targets including NF-κB and actin by covalent modification.
• Andrographis paniculata herb to identify its possible
anticataractogenic effect on selenite induced cataract
model. Andrographis paniculata is a known herb having
antioxidative property.
• In Ayurvedic medicine, it is used as a bitter tonic, to
stimulate digestion and as a treatment for a wide range of
conditions, such as diabetes and hepatitis.
21. Method of isolation:
1. Successive extraction of the powder with petroleum ether (40 -60°C), chloroform, ethyl
acetate, acetone, methanol and test each extract for activity.
2. Further fractionation of the active extract/s by suitable solvents and test the fractions for
activity.
3. Subject the active fractions to column chromatography.
Chemical test: Kedde test – Violet blue colouration
TLC/HPTLC:
Stationary phase: Silica gel G,
Mobile phase: Cloroform: tolune: methanol (66: 26: 8)
Detection: Anisaldehyde - H2SO4 heat at 110°C
Andrographolides
• HPLC:
• Method : Isocratic
• Stationary phase: C18
• Mobile phase: Acetonitril : phosphoric acid in water (40:60)
• Detection: PDA 223 nm
22. Phyllanthus
• The genus Phyllanthus (Euphorbiaceae) contains 550– 750 species
in 10–11 subgenera that are distributed in all tropical regions of the
world from Africa to Asia, South America and the West Indies.
Phyllanthus amarus is the most widespread species and is typically
to be found along roads and valleys,
• The major lignans of the genus, namely, phyllanthin (1) and
hypophyllanthin (2), have been shown to be anti-hepatotoxic
against carbon tetrachloride- and galactosamine-induced
hepatotoxicity in primary cultured rat hepatocytes
23. Procedure:
• Mix powder drug with lime water,
allow to stand overnight.
• The mass is transfer to soxhlet apparatus
and extract with pet. Ether
• Collect pet. Ether extract & Concentrate it.
• Mix with methanol and boil. Collect the defatted extract conc.
It evaporate upto dryness.
• Dry residue mix in pet. Ether, concentrate and allow to stand
(yellow oil get saperate) .
• Residue is used for column chromatography by silica gel G
and elute with n-hexane: ethyl acetate (99:1)
• Collect the fractions of 99- 108 hypophyllanthin and 109- 137
phyllanthin.
• Saperate pure phyllanthin and perform its TLC
25. Withanolides
•Withania somnifera (Solanaceae), known
in India as Ashwagandha or winter cherry.
•Adaptogenic, anti-sedative and anti-
convulsion activities, and the plant has
been employed in the treatment of
neurological disorders, geriatric debilities,
arthritis and stress- and behaviour-related
problems
•Nine closely related withanolides of W.
somnifera, viz. 27-hydroxy withanone (1),
17-hydroxy withaferin A (2), 17-hydroxy-
27-deoxy withaferin A (3), withaferin A
(4), withanolide D (5), 27-hydroxy
withanolide B (6), withanolide A (7),
withanone (8) and 27- deoxywithaferin A
(9)
26. Isolation of withanolides:
• Take 10 gm dried powder. Place it in a 500 ml stopperd flask. Add
100ml of 1% solution of H2SO4 and mix well.
• Keep this mixture overnight. Shake it for half hr on horizontal
shaker.
• Filter and collect, wash residue with 40ml of 1% H2SO4 and
collect the washings in filtrate. Repeat the process twice
• Add Cacl2
• Filter, conc. it to get withania alkaloid.
TLC:
• Adsorbant : Silica gel G
• Solvent system: Chloroform:Methanol(99:1)
• Detection: UV 254
27. Identification test:
Sodium picrate test: Yellow colour of paper turns to brick red.
Guaiacum resin test: Cut surface of bark+ Cuso4 moisten filter paper-
cut surface of bark turns to blue colour.
Ephidrine
Ephidra gerandiana. Family Ephidraceae
C.C.: Ephidrine, Pseudoephidrine.
Caution is advised as an overdose can be fatal, causing high blood
pressure, racing of the heart, confusion, nervous stupor, twitching,
convolutions and death. Ephedrine is seen as a performance-
boosting herb and is a forbidden substance in many sporting events
such as athletics. This herb should not be used by people who are
taking monoamine oxidase inhibitors, or suffering from high blood
pressure, hyperthyroidism or glaucoma.
28. Extraction:
• Dried arial stem powder.
• Extract with pet. Ether. Dry marc and moisten with ammonia.
• Extract marc with alcohol. Filter and evaporate filtrate to obtained
syrupy mass.
• Extract this marc with 3 portions aq. Alcohol. Make alkaline
• Filter and evaporate to obtained dry residue of ephidrine.
Identification test:
1. Ephedrine crystal test- T.S.+ Chloroform allow to stand 24hrs.
Evaporate solvents
2. Ephidrine copper sulphate : 1ml HCL 0.5ml of 5% CuSO4 + few
drops of NaOH solution. Now add 2ml of ether and shake well. –
Aq. Layer will blue & ether layer become purple.
29. TLC/HPTLC:
Stationary phase: Silica gel G,
Mobile phase: Tolune: Chloroform: ethanol (29:6: 15)
Detection: Dragendroff reagent (Orange brown colour)or
0.5% iodine in chloroform (UV 365nm).
HPLC:
• Method : Isocratic
• Stationary phase: Pentaflurophenylpropyl (PFPP)
• Mobile phase: Ammonium acetate (7M) in Acetonitrile
:water (9:1)
• Detection: UV visible detection at 215nm.