SOXHLET APPARATUS

HI, soxhlet apparatus (experiment) is one of my favourite experiments.

most of the students in their final year will work on soxhlet apparatus.

this is useful for extracting the chemical constituents like flavonoids, alkaloids, tannins, etc.,

this is found by a great scientist called SOXHLET

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FATHIMA INSTITUTE OF PHARMACY
Student Help Line Association


PHARMACOGNOSY II K. Bharath (B.Pharm)

Glycosides:

 Glycosides are organic compounds of plant and animal sources.
 Glycosides give sugar and non sugar moieties, on hydrolysis.
 Sugar moiety is called glycon and non sugar moiety is aglycone.
 Glycosides are acetals/sugar ethers formed by the interaction of hydroxyl groups of sugar and non sugar moiety, by loosing water molecule.
 β-D-glucose is involved in the glycosides.
 The sugars are galactose, mannose, rhamnose, digitoxose,cymarose etc.
 The linkage between glycone and aglycone is called glycosidic linkage.
 Based in this, glycosides are classified into α and β glycosides.

Classification of glycosides is done based on three things

o Chemical nature of aglycone part.
o
o Therapeutic activity of aglycone part.
o
o Linkage between glycone and aglycone part.




According to chemical nature of aglycone moiety:



Therapeutic activity:
i. Cathartics
ii. Cerbiotonics
iii. Analgesics
iv. Anti-rheumatics
v. Anti-ulcer
Linkage across glycone and aglycone part:
Actually link is between ’OH’ group of glycone and radicals like CH, -OH, -SH, and –NH of aglycone part by removing water molecule.
If CH is taken as radical for aglycone part then it is
C-glycoside
OHO-glycoside
NHN-glycoside
SHS-glycoside

C-glycosides:
Glycone –OH+HC-aglyconeglycone-C—aglycone+water
Ex: Aloe(Liliaceae), cascara
O-glycoside:
Glycone-OH+HO-aglyconeglycone-O-aglycone+water
Ex: Senna, rhubarb frangula etc,.
S-glycoside:
Glycone-OH+HS-aglyconeglycone-S-aglycone+water
Ex: Isothiocyanate glycosides
N-glycoside:
Glycone-OH+HN-glyconeglycone-N-glycone+water
Ex: Nucleosides
●Expect resin glycosides all the glycosides are soluble in water and dilute alcohol & insoluble in chloroform or Ether but aglycone moiety is soluble in chloroform & Ether

SAPONIN GLYCOSIDES
Saponin:
 These are the glycosides which give foam on shaking with NaHCO3.
 The saponin glycosides have soap like action.
 They are called haemotoxic because they cause haemolysis of erythrocytes(Red blood cells).Because of this, these are used as fish poisons.
 They cause irritation of Mucous membrane.
 Soluble in water and alcohol, but insoluble in non-polar organic solvents.
 The aglycone part is called sapogenin. Depending on the nature and structures they are divided into two groups
1. Steroidal saponins[Tetracyclic triterpenoid]
2. Pentacyclic Triterpenoid saponins



The following are the drugs containing saponin glycosides
i. Glycyrrhiza
ii. Ginseng
iii. Discorea
iv. Sarasaparilla
v. Senega



1.DIOSCOREA

Synonyms:Yam, Rheumatism root.

Biologcal Source:
It consists of dried tubers of plants, Dioscorea deltoidea, D.composita,and other species of Dioscorea, family Dioscoreaceae.

Geographical Source:
Found in North Western Himalayas upto an altitude of 1000-3000m,and also in Jammu and Kashmir,Himachal Pradesh.



CULTIVATION AND COLLECTON:
Mainly grown in TamilNadu, West Bengal, Maharashtra,Karnataka and Jammu and Kashmir.
 As raising the crop from seeds has disadvantages like longer time and variability in progeny(off spring),healthy tubers of about 70-80 gm in weight are selected for cultivation.
 They are sown in nursery beds after treating with fungicide
 It takes 30-40 days for their sprouting .
 After 3-4 months they are transplanted in field .
 They are placed at a distance of 30x60 cm.
 Trellis(support for climbing trees) are used.
 Inter-cropping with legumes can be done
 Diosgenin content is found to be high as well as rhizomes lose about 50% of their weight on drying.

MICROSCOPIC STRUCTURES:

Colour: slightly brown.
Odour: odourless.
Taste: bitter.
Size: varies dipending on sizes rhizomes.

MACROSCOPIC CHARACTERS:

Epidermis:Absent in transverse section of drug.
Cork: Few layers followed by parenchymatous.
Stele:Major part of drug and consists of close Collateral fibro-vascular bundles.
Endodermis and pericycle is indistinguishable.



CHEMICAL CONSTITUENTS :

Rhizome contain 75% of starch.It contains diosgenin ,steroidal sapogenin(4-6%), its glycosides , smilagenin and epismilagenin and β-isomer yammogenin.
Rhizomes also contain sapogenase.Diosgenin is the hydrolytic product of saponin dioscin.

USES:
Used in synthesis of corticosteroids , sex harmones , oral contraceptives and used in treatment of rheumatic arthritis(inflammation and deformation of bone), asthma, eczema.
Isolation:
Hydrolysis of dioscin is done by mineral acids.Diosgenin is liberated and extracted with the help of non polar solvents like benzene or solvent ether.
Diosgenin is degraded to 16-dehydro pregnenelone acetate.This is used for synthesis of
a. Corticosteroids like cortisone, hydrocortisone, prednisolone
b. Pregnenes like progesterone, 17-α-hydroxy progesterone
c. Androstanes like testosterone. Methyl testosterone, etc,and
d. 19-NOR steroids like estrone, 17- α-ehynyl estradiol and norethisterone acetate.
The above steps are done by microbial transformations.

ISOLATION OF ALKALOIDS by bharath.

 Isolation of alkaloids is very easy.
 First we have to identify the presence of alkaloid in the plant.
 These alkaloids are treated with the different reagents like
tannic acid,
picric acid,
picolinic acid,
perchloric acid,
mercuric iodide{Mayer’s reagent},
iodine dissolved in potassium iodide{Wegner’s reagent},
potassium bismuth iodide{Dragendoffr’s reagent},
phosphomolybdic acid{Sonneuschein’s reagent }, and
phosphotungstic acid {Scheibler’s reagent}, with wich the alkaloids either give precipitate or turbidity.
 These reagents do not have quantitative analysis of alkaloids, because the compound are not sufficiently insoluble and partly because the reagents precipitate out other organic substances also. A general procedure recommended by Manske is described below.


 Extraction of plant material with petroleum ether for the removal of soluble fats
 Again extraction with methyl alcohol to remove cellulosic and other insoluble material and the filtrate so obtained is evaporated.
 Then it is dissolved in water, acidified to pH 2 and steam distilled to remove methyl alcohol.
 Now paraffin is used to remove suspended impurities.
 Then filtrate is extracted with ether or chloroform to remove water soluble non basic organic material and the steam distilled where the steam volatile alkaloids are separated.
 Again extracted with ether or chloroform and the etheral layer obtained after this extraction is evaporated to give crude alkaloids.
 The crude mixture is separated into individual alkaloids by
 Fractional crystallization,
 Fractional precipitation,
 Column chromatography,
 Partition chromatography,
 Gas chromatography ,
 Counter current extraction.
This is about isolation of alkaloids

Tabular form of saponin glycosides

Contents DIOSCOREA GLYCYRRHIZA GINSENG SENEGA
Synonym Yam,Rheumatism root. Glycyrrhiza ,
Liquoric root,mulethi,glycyrrhizae radix. Ninjin,Pannag, Panax . Senega root, rattle snake root, Senega snake root.
Biological source Dried stem tubers of dioscorea deltoidea, D.composita
DIASCORACEAE Dried ,peeled or unpeeled, root and stolon of Glycyrrhiza glabra linn.
LEGUMINOSAE Dried root of Panaxginseng P.japonic P.notoginseng ARALIACEAE Dried root and rootstock of Polygala senega.
POLYGALACEAE
Geographical sourse Northwestern Himalayas from Kashmir and Punjab to Nepal and china U.S.A. and Mexico Spain, Siciy and England.
Glycyrrhiza glabra var.glandulifera – Russia
Glycyrrhiza glabra var.Violacea- Iran Korea ,China, Russia .Japan, Kanada , U.S.A Indigenous to Minnesota in U.S.A and eastern Canada,Japan.
Macroscopic characters Colour:Slightly brown
Odour:Odourless
Taste:Bitter
Size:Varies depending upon age of Rhizomes Colour :Unpeeled-Yellowish brown- -internally-dark yellow, externally-brown
Peeled:Pale yellow in colour
Odour::Faint and characteristic
Taste :Sweet
Size :Length 20 to 50 cm and 2 cm in diameter
Shape:cylindrical pieces,peeles angular
Fracture:It is fibrous in dark and splintery in wood Colour:Yellowish,White or Red
These are transluscent and possess stem cars
Shape:Tuberous corpulent roots Shape:Elongated tapering root and bearing a tufted crown
Colour:Grenish to brownish yellow
Fracture:smooth and splintery
Taste:first sweet and then acrid
odour:characteristics of methyl salicylate
Bharath’s SAPONIN GLYCOSIDES



Uses Rhizomes-Rich source of Diosgenin
Diosgenin is precursor for synthesis of
-severalcorticoids
-sex harmones
-oral contraceptives used in treatment of Rheumatic arthritis
Expectorant,demulscent,flavouring agent in drugs like NH3Cl, alkaliliodides,quinine,cascara..
Treating peptic ulcer.
Anti spasmodic due to presence of isoliquiritin
Rhematid arthritis,addison’s disease.
Antiinflammatory drug.Not recommended during pregnancy and breast feeding because low levels of testosterone in men and high levels of prolactin in women.
It si immunomodulatory drug.
Increae the resistance.
Both stimulant and sedative.
Used as aphrodisiac
Demulscent in gastritis and aneamia.Prolongs the life of diabetic persons.
Used in Adrenal and Thyroid dysfunctioning
Chemical constituents 75% Starch
main constituent Diosgenin

glycosides
Smilagenin
Epismilagenin,
β–isomer yammoginin
Rhizomes–sapogenase(enzyme)
Tubers–glycosides,
Phenolic compounds
Diosgenin is the hydrolythic product of saponindioscin Main constituentglycyrrhizin(glycyrrhizic acid)
Glycyrrhizinic acid on hydrolysis yields glycyrrhetinic acid (glycyrretic acid)
It consists of triterpenoid structure
Spanish5–10%,
Russiaabout 10%,
Persia7.5–3%,
glucose,sucrose,asparagin,
Presence of flavonoids like liquiritin and isoliquiritin.causes anti gaustric effect and anti ulcer effect.
Carbenoxolone:oleandane derivative, has mineralocorticoid activity.↑prostaglandins,↓pepsinogen.



Ginsenosides(13)
Panaxosides
Chikustsusaponin
Dammarol(aglycone of Ginsenosides)
Oleanolic acid(aglycone of panaxadiol)

Panaxosides gives Oleanolic acid,
Panaxadiol,
Panaxatriol on decomposition
Bharath’s SPAONIN GLYCOSIDES
`

FATHIMA INSTITUTE OF PHARMACY
Student Help Line Association


PHARMACOGNOSY II K. Bharath (B.Pharm)

Glycosides:

 Glycosides are organic compounds of plant and animal sources.
 Glycosides give sugar and non sugar moieties, on hydrolysis.
 Sugar moiety is called glycon and non sugar moiety is aglycone.
 Glycosides are acetals/sugar ethers formed by the interaction of hydroxyl groups of sugar and non sugar moiety, by loosing water molecule.
 β-D-glucose is involved in the glycosides.
 The sugars are galactose, mannose, rhamnose, digitoxose,cymarose etc.
 The linkage between glycone and aglycone is called glycosidic linkage.
 Based in this, glycosides are classified into α and β glycosides.

Classification of glycosides is done based on three things

o Chemical nature of aglycone part.
o
o Therapeutic activity of aglycone part.
o
o Linkage between glycone and aglycone part.




According to chemical nature of aglycone moiety:



Therapeutic activity:
i. Cathartics
ii. Cerbiotonics
iii. Analgesics
iv. Anti-rheumatics
v. Anti-ulcer
Linkage across glycone and aglycone part:
Actually link is between ’OH’ group of glycone and radicals like CH, -OH, -SH, and –NH of aglycone part by removing water molecule.
If CH is taken as radical for aglycone part then it is
C-glycoside
OHO-glycoside
NHN-glycoside
SHS-glycoside

C-glycosides:
Glycone –OH+HC-aglyconeglycone-C—aglycone+water
Ex: Aloe(Liliaceae), cascara
O-glycoside:
Glycone-OH+HO-aglyconeglycone-O-aglycone+water
Ex: Senna, rhubarb frangula etc,.
S-glycoside:
Glycone-OH+HS-aglyconeglycone-S-aglycone+water
Ex: Isothiocyanate glycosides
N-glycoside:
Glycone-OH+HN-glyconeglycone-N-glycone+water
Ex: Nucleosides
●Expect resin glycosides all the glycosides are soluble in water and dilute alcohol & insoluble in chloroform or Ether but aglycone moiety is soluble in chloroform & Ether

SAPONIN GLYCOSIDES
Saponin:
 These are the glycosides which give foam on shaking with NaHCO3.
 The saponin glycosides have soap like action.
 They are called haemotoxic because they cause haemolysis of erythrocytes(Red blood cells).Because of this, these are used as fish poisons.
 They cause irritation of Mucous membrane.
 Soluble in water and alcohol, but insoluble in non-polar organic solvents.
 The aglycone part is called sapogenin. Depending on the nature and structures they are divided into two groups
1. Steroidal saponins[Tetracyclic triterpenoid]
2. Pentacyclic Triterpenoid saponins



The following are the drugs containing saponin glycosides
i. Glycyrrhiza
ii. Ginseng
iii. Discorea
iv. Sarasaparilla
v. Senega



1.DIOSCOREA

Synonyms:Yam, Rheumatism root.

Biologcal Source:
It consists of dried tubers of plants, Dioscorea deltoidea, D.composita,and other species of Dioscorea, family Dioscoreaceae.

Geographical Source:
Found in North Western Himalayas upto an altitude of 1000-3000m,and also in Jammu and Kashmir,Himachal Pradesh.



CULTIVATION AND COLLECTON:
Mainly grown in TamilNadu, West Bengal, Maharashtra,Karnataka and Jammu and Kashmir.
 As raising the crop from seeds has disadvantages like longer time and variability in progeny(off spring),healthy tubers of about 70-80 gm in weight are selected for cultivation.
 They are sown in nursery beds after treating with fungicide
 It takes 30-40 days for their sprouting .
 After 3-4 months they are transplanted in field .
 They are placed at a distance of 30x60 cm.
 Trellis(support for climbing trees) are used.
 Inter-cropping with legumes can be done
 Diosgenin content is found to be high as well as rhizomes lose about 50% of their weight on drying.

MICROSCOPIC STRUCTURES:

Colour: slightly brown.
Odour: odourless.
Taste: bitter.
Size: varies dipending on sizes rhizomes.

MACROSCOPIC CHARACTERS:

Epidermis:Absent in transverse section of drug.
Cork: Few layers followed by parenchymatous.
Stele:Major part of drug and consists of close Collateral fibro-vascular bundles.
Endodermis and pericycle is indistinguishable.



CHEMICAL CONSTITUENTS :

Rhizome contain 75% of starch.It contains diosgenin ,steroidal sapogenin(4-6%), its glycosides , smilagenin and epismilagenin and β-isomer yammogenin.
Rhizomes also contain sapogenase.Diosgenin is the hydrolytic product of saponin dioscin.

USES:
Used in synthesis of corticosteroids , sex harmones , oral contraceptives and used in treatment of rheumatic arthritis(inflammation and deformation of bone), asthma, eczema.
Isolation:
Hydrolysis of dioscin is done by mineral acids.Diosgenin is liberated and extracted with the help of non polar solvents like benzene or solvent ether.
Diosgenin is degraded to 16-dehydro pregnenelone acetate.This is used for synthesis of
a. Corticosteroids like cortisone, hydrocortisone, prednisolone
b. Pregnenes like progesterone, 17-α-hydroxy progesterone
c. Androstanes like testosterone. Methyl testosterone, etc,and
d. 19-NOR steroids like estrone, 17- α-ehynyl estradiol and norethisterone acetate.
The above steps are done by microbial transformations.