Glycoside
Priyanka Goswami
What are Glycosides?
• Organic molecules + sugar moiety (mostly monosacchrides)
• Definition: organic compounds, from plan...
Classification of Glycosides

1. C-Glycoside: when sugar moiety is linked with Carbon atom
• E.g. Cascaroside of Cascara, ...
Syllabus
Semester 7 :
• Anthraquinone
• Iso-thiocyante
• Cyanogenetic
• Napthaquinone
Semester 8:
• Cardiac
• Saponin
Anthraquinone glycoside
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•
•
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Rhubarb, Aloe, Senna and Cascara- purgative-unknown chemistry before.
Vegetable & ani...
Isolation
•
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Chrysophanol & chrysophanic acid: Rhubarb & Cascara
Aloe-emodin: Rhubarb & Senna
Rhein: Rhubarb & Sen...
Chemistry
• Derivative of anthraquinone Glycoside:
o
o
o
o
o
o

Dihydroxy phenol: Chrysophanol
Trihydroxy phenol: Emodin
T...
Extraction procedure
• Powder drug
• Macerate with immiscible organic solvent
(ether is recommended)
• Filter
• To the Fil...
Anthranols & Anthrones
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Reduced anthraquinone derivative
Occur either free or combined as glycosides
I...
Oxanthrones
• Intermediate product between anthraquinone and anthranols.
• They give anthraquinones on oxidation and fairb...
Dianthrones
• Derived from 2 anthrone molecules, which maybe identical or different.
• They readily form a result of mild ...
Pharmacological action
•
•
•
•

Action is restricted to large bowel.
Hence the effect is delayed up to 6 h or longer.
The ...
Anthraquinone
Glycoside
1.
2.
3.
4.
5.
6.
7.
8.

Rubia
Cochineal
Aloe
Hypericum
Cascara
Andira
Senna
Rhubarb
1. Rubia
alizarin

Syn: Madder
Source: dried roots of Rubia tinctorum
Family: Rubiaceae
GS: Asia, Europe
Specification: no...
2. Cochineal
• Source: dried female insect
Dactylopius coccus containing eggs and larvae
• Family: Coccidae, Order: Hemipt...
3. Aloe

• Syn: Kumari, Musabbar
• Source: dried juice of the leaves of Curacao-(Aloe barbadensis), Socotrine-(Aloe perryi...
Curacao aloe- Preparation
Barbados (Curacao) Aloe
V-shaped transverse cut at the base of flesh leaf
Place cut leaves in wo...
Cape aloe- Preparation
• Barbados (Curacao) Aloe
• Transversely cut leaves are arranged in a circular manner in the basin
...
Socotrine & Zanzibar aloePreparation
• Socotrine Aloe
o The juice of leaves is collected in goat skin and allowed to
becom...
Constituents
• Principal active constituent: aloin which is mixture of glucosides among
which barbaloin (aloe-emodin anthr...
Chemical Test
1. Nitrous acid Test: crystals of sodium nitrite along with small quantity of
acetic acid are added to aqueo...
USE
• Aloe is purgative; mainly on colon
• Ingredient of tincture of Benzoin (friar’s balsam)
• In cosmetics
4. Hypericum
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Syn: St. John’s wort
Source: dried aerial parts of Hypericum perforatum
Family: Hypericaceae (Clus...
5. Cascara
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Syn: Sacred bark, Chittern bark
Source: dried bark of Rhamnus purshiana
Family: Rhamnaceae
GS: Pacif...
6. Andira
Syn: Goa Powder
Source: lysogenous cavity in the wood of Andira araroba
Family: Leguminosae
GS: Malabar coast
Fo...
7. Senna
• Syn: Senna ki patti
• Source: dried leaflets of Cassia angustifolia (Indian-Tinnevelly),
Cassia acutifolia (Ale...
•
•
•
•
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•
•

Morphology:
Color: Yellowish green
Odor : Slight
Taste: mucilaginous, bitter,
characteristic
Shape: Lance...
Cultivation
• Soil: red loamy
• Sowing period: Feb-March & Oct-Nov
• Sowing method: broadcasting (by
hand mechanically)
• ...
• Chemical Test: Borntrager’s Test
1. Boil  Drug + dilute H2SO4
2. Filter
3. Add to Filtrate: benzene (or ether or
chloro...
8. Rhubarb

• Syn: Revandchini
• Source: dried rhizomes of Indian - Rheum emodi
Chinese - Rheum palmatum, Rhum webbianum
•...
• Morphology:
o Round pieces are prepared from small rhizomes which are cut only transversely and
hence they are barrel sh...
• Chemical Test:
o Rhubarb gives modified Borntrager’s test positive
o Rhubarb + alkali  red color (due to anthraquinone ...
Rhapontic rhubarb
Source: rhizomes of Rheum rhapontic
GS: Southern siberia and surrounding region of Volga river
Descripti...
Iso thiocyanate Glycoside
• They are called as Glucosinates.
• Aglycone part of such glycoside contains isothiocyanate, as...
Brassica
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•
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Syn: black or brown mustard, sinapsis
Source: dried ripe seeds of brown or black Brassica nigra or Bra...
White brassica
• Source: dried seeds of Sinapsis alba
• Family: Cruciferae
• Constituents: glucoside sinalbin & myrosin.
o...
Cyanogenetic Glycoside
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Also termed as Cyanophore Glycoside
Derivatives of mandelonitrile
On hydrolysi...
1. Wild cherry bark
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•
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Syn: wild black cherry, Virginian prune bark
Source: dried bark of Prunus serotina
Family...
2. Bitter almond
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Syn: Amygdala amara
Source: dried ripe seeds of Prunus amygdalus
Family: Rosaceae
Consti...
Napthoquinone Glycoside
1.
2.
3.
4.
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Plumbago
Henna
Alkanna
Walnut
They are produced by higher plants, fungi...
1. Plumbago
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Syn: Chitrak
Source: dried matured roots of Plumbago zeylanica
Family: Plumbaginaceae
GS: India, ...
2. Alkanna
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Syn: Alkanet, Anchusae radix
Source: dried root of Alkanna tinctoria
Family: Boraginaceae
GS: Hungar...
3. Henna
Syn: Mehendi
Source: dried leaves of Lawsonia inermis
Family: Lythraceae
GS: North Africa,Egypt, India, Ceylon
OH...
4. Walnut
• Syn: apricot
• Source: dried fruits of Juglans regia,-Persian J.cinerea-Butter nuts, J.nigra-black
wallnut
• F...
Biosynthesis
• Transfer of a uridylyl group from uridine triphosphate to a sugar 1-phosphate.
• Enzymes catalysing reactio...
Biosynthesis of Juglone
Shikimic acid pathway

55-o-succinyl benozic
acid,
57-beta hydroxy
juglone,
56-juglone
Biosynthesis of Juglone

38-o-succinyl benozic acid,
40-1,4-dihydroxy-2-napthoic acid
41-lawsone
42-1,4-naphthaquinon
43-2...
Biosynthesis of anthraquinone
• By acetate mevalonate pathway or isochorismate alpha ketoglutaric acid
-acetate pathway.
•...
Biosynthesis of Aloe-emodin

Polyketide biosynthesis
Biosynthesis of Amygdalin
• Defense mechanism: ability to produce toxic amounts of HCN, which is
extremely toxic to most o...
Biosynthesis of Amygdalin
Anthraquinone-Napthaquione-Cyanogenetic Glycoside
Anthraquinone-Napthaquione-Cyanogenetic Glycoside
Anthraquinone-Napthaquione-Cyanogenetic Glycoside
Anthraquinone-Napthaquione-Cyanogenetic Glycoside
Anthraquinone-Napthaquione-Cyanogenetic Glycoside
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Anthraquinone-Napthaquione-Cyanogenetic Glycoside

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  • Anthraquinone-Napthaquione-Cyanogenetic Glycoside

    1. 1. Glycoside Priyanka Goswami
    2. 2. What are Glycosides? • Organic molecules + sugar moiety (mostly monosacchrides) • Definition: organic compounds, from plants & animal sources, which on enzymatic or acid hydrolysis, give one or more sugar moieties (glycone) with non-sugar moiety (aglycone-genin). • Acetayls or sugar ethers • Formed by –OH group of each of non-sugar and sugar moiety, with loss of water, -OH group of aglycone maybe alcoholic or phenolic and in some cases amines also. • Sugar involved in glycosides are of different types but mostly, beta-DGlucose. • Classification of Glycosdies either of o Chemical nature of aglycone part o Therapeutic activity of aglycone part o Linkage between glycone & aglycone
    3. 3. Classification of Glycosides 1. C-Glycoside: when sugar moiety is linked with Carbon atom • E.g. Cascaroside of Cascara, Aloin of Aloe, Carminic acid of Cochineal • Mainly present in Liliaceae family • Not hydrolysed by heating with dilute acid/alkali, but by oxidative hydrolysis with ferric chloride. • Glycone – OH + H.C –aglycone  Glycone –C-aglycone + H2O 2. O-Glycoside: when sugar moiety is linked with Oxygen atom • hydrolysed by treatment of acid/alkali in to aglycone and sugar • E.g glucoranillin • Glycone –OH + HO -aglycone  Glycone-O-aglycone + H2O 3. S-Glycoside: when sugar moiety is linked to sulphur atom • Occurrence Iso-thiocyante glycoside (Sinigrin from Black mustard) • Glycone –OH + HS-aglcyone  Glycone-S-aglycone + H2O 4. N- Glycoside: when sugar moiety is linked to nitrogen atom E.g. nucleoside, where amino group of base reacts with –OH group of ribose/deoxyribose, ultimately gives N-glycosidic form Glycone-OH + HN-aglycone  Glycone-N-aglycone + H2O
    4. 4. Syllabus Semester 7 : • Anthraquinone • Iso-thiocyante • Cyanogenetic • Napthaquinone Semester 8: • Cardiac • Saponin
    5. 5. Anthraquinone glycoside • • • • • • Rhubarb, Aloe, Senna and Cascara- purgative-unknown chemistry before. Vegetable & animal dyestuff –madder and cochineal Similarity between: purgative drugs & dye stuff: apparent Emodin-identified (aglycone-purgative drug-Rhamnus spp.) Alizarine-identified (aglycone-dyestuff-madder plant) Reduced anthraquinonesoxanthrone, anthrol , anthrone, union of two anthrone (dianthrone)
    6. 6. Isolation • • • • • Chrysophanol & chrysophanic acid: Rhubarb & Cascara Aloe-emodin: Rhubarb & Senna Rhein: Rhubarb & Senna Emodin/Frangula emodin: Rhubard & Cascara Synthesized either via acetate-malonate pathway or they are derived from shikimate and mevalonate. • Substitution at 1,8-dihydroxy.
    7. 7. Chemistry • Derivative of anthraquinone Glycoside: o o o o o o Dihydroxy phenol: Chrysophanol Trihydroxy phenol: Emodin Tetrahydroxy phenol: Carminic acid Methyl group: chrysophanol Hydroxymethyl group: Aloe-emodin Carboxyl group: Rhein & Carminic acid • Nature: o Orange-red compounds (medullary rays of Rhubarb & Cascara) o Usually soluble in hot water & dilute alcohol o Detected by Borntrager’s Test
    8. 8. Extraction procedure • Powder drug • Macerate with immiscible organic solvent (ether is recommended) • Filter • To the Filtrate: aqueous ammonia or caustic soda • Shake • Pink/red/violet color • Presence of anthraquinone derivative • If only glycosides are present; • First hydrolyzing with alcoholic KOH or acid. • When alkali is added to powdered drug/section  red color produced served to locate anthraquinone derivative in the tissue (e.g. medullary rays of cascara bark) . • If drug contains either very stable anthraquinone glycoside or reduced derivative of anthranol type , Borntrager’s test will be negative.
    9. 9. Anthranols & Anthrones • • • • • • • • • • Reduced anthraquinone derivative Occur either free or combined as glycosides Isomeric and one may be partially converted to the other in solution. The parent substance, anthrone; pale yellow-non fluorescent substance and is insoluble in alkali. Anthranol derivatives, brownish-yellow, forms a strongly fluorescent solution in alkali. Anthranol derivative, found in aloe also have similar properties, strong green fluorescence which aloe gives in borax or other alkaline solution has been used for identification test. Anthranol & Anthrone, main constituents of chrysarobin, mixture of substance prepared by benzene extraction from the material (araroba) found in the trunk cavities of the tree Andira araroba. If a little chryasarobin is treated on a white tile with a drop of fuming nitric acid , anthranols are getting converted into anthraquinone glycoside. A drop of ammonia allowed to mix gradually with the acid liquid produces violet color. This modification of Borntrager’s Test had been used for identity before underlying chemistry was known.
    10. 10. Oxanthrones • Intermediate product between anthraquinone and anthranols. • They give anthraquinones on oxidation and fairbairn’s modification of the Borntrager’s test accomplishes this by means of hydrogen peroxide. • An Oxanthrone has been reported as a constituent of cascara bark.
    11. 11. Dianthrones • Derived from 2 anthrone molecules, which maybe identical or different. • They readily form a result of mild oxidation of the anthrone or mixed anthrones. (e.g. a solution in acetone and presence of atmospheric oxygen.) • They are important aglycones in species of Cassia, Rheum and Rhamnus. • Two chiral centers at C-10 and C-10’ are present in the dianthrones, and for a compound having two identical anthrone moieties e.g. sennidin A, two forms (the 10S, 10S’ and 10R, 10R’) . • Occur in plants as their 1,1’-diglucosides.
    12. 12. Pharmacological action • • • • Action is restricted to large bowel. Hence the effect is delayed up to 6 h or longer. The nature of peristaltic initiation is not known. But derivative influence the ion transport across colon cells by inhibition chloride channels.
    13. 13. Anthraquinone Glycoside 1. 2. 3. 4. 5. 6. 7. 8. Rubia Cochineal Aloe Hypericum Cascara Andira Senna Rhubarb
    14. 14. 1. Rubia alizarin Syn: Madder Source: dried roots of Rubia tinctorum Family: Rubiaceae GS: Asia, Europe Specification: not harvested before a minimum of 18 months & maximum of 2 months in order to get greater yield of dye. • Constituents: anthraquinone glycoside chiefly: ruberythric acid hydrolysisalizarin and primeverose • Use: dyeing cotton, wool, linen, silk. • Note: dyeing of cottton with alizarn originatd in India and subsequently reached other countries including Turkey. It was dyed from hard water bath containing alum as a mordant. The red color produced is quiet fast and useful for dyeing. • • • • •
    15. 15. 2. Cochineal • Source: dried female insect Dactylopius coccus containing eggs and larvae • Family: Coccidae, Order: Hemiptera • GS: America, Caribbean island • US-FDA approved color for food and drugs • Constituents: 10% Carminic acid (red coloring matter-glucosidal anthraquinone), 10% fat, 2% wax, Coccerin • CT: carminic acid + water  deep red color as do + acid  yellow-violet color • Use: coloring agent for foods, drugs, cosmetic products, preparation of lakes,inks, acid-base indicator, microscopic stain and in photography • Carmic acid is used to prepare carmine.
    16. 16. 3. Aloe • Syn: Kumari, Musabbar • Source: dried juice of the leaves of Curacao-(Aloe barbadensis), Socotrine-(Aloe perryi), Zanzibar-(Aloe ferox), Cape aloe-(Aloe spicata) • Family: Liliaceae • GS: africa, carribean island • Meaning: aloe from arabic word viz. alloch: a shining bitter substance; vera: true; ferox: wild; spicata: flowers in spikes; barbadensis: habitat of plant. • Description: Leaves: sessile; apex: strong spine; lower portion: rounder & upper portion: slightly concave • Cultivation: root sucker are used; grow well even in poor grades of soils and in dry climatic condition ; water logging near plant must be prevented; manure: N+P+K is used; leaves are cut in 2nd yr of cultivation.; drug is obtained from leaves of 12 years. • During collection of leaves; cut is given to leaves near their bases
    17. 17. Curacao aloe- Preparation Barbados (Curacao) Aloe V-shaped transverse cut at the base of flesh leaf Place cut leaves in wooden troughs Immediately placing in kerosene; due to spines on the leaves. Then place in wooden troughs & kept in titled position to drain out all the juice. • Boil the juice collected this way in large copper pans. • During boiling latex evaporates, juice is further thickened. • Thick juice is then poured into gourds or metal container where it hardens. • • • • •
    18. 18. Cape aloe- Preparation • Barbados (Curacao) Aloe • Transversely cut leaves are arranged in a circular manner in the basin shaped depression • Dug in the ground which is lined either with goat skin or canvas. • Leaves are placed in a such way so as to overlap the cut ends. • Kept in this position for 5-6 hours, till all the juice exudes out and collected in goat skin • Collected juice is transferred to large iron kettle where it boiled and stirred continuously with the help of a wooden paddle type instrument. • When boiling juice attains a desired concentration, it is poured into wooden cases.
    19. 19. Socotrine & Zanzibar aloePreparation • Socotrine Aloe o The juice of leaves is collected in goat skin and allowed to become semisolid in nature. • Zanzibar Aloe o The juice of this variety is poured into skins of some small carnivoros animals. o Where it get solidifies and as such packed in wooden boxes
    20. 20. Constituents • Principal active constituent: aloin which is mixture of glucosides among which barbaloin (aloe-emodin anthrone C-10 glucoside) is the chief constituent. • Barbaloin is a C-glycoside and it is not hydrolysed by heating with dilute acids or alkalis. Ferric chloride is decomposes barbaloin by oxidative hydrolysis into aloe-emodin-anthrone, little aloe-emodin and glucose. • Along with barbaloin, aloe also contains isobarbaloin, beta barbaloin, aloeemodin & resin. • Aloeresin also responsible for purgative action of aloe.
    21. 21. Chemical Test 1. Nitrous acid Test: crystals of sodium nitrite along with small quantity of acetic acid are added to aqueous solution of aloe 1. 2. 3. Curacao aloe: sharp pink to carmine color Cape aloe: faint pink color Socotrine/Zanzibar aloe: very less change in color (due to isobarbaloin) 1. Nitric acid Test: either by directly applying nitric acid to drug or to its aqueous solution 1. 2. 3. 4. Curacao aloe: deep brownish red color Cape aloe: brownish color changing to green Socotrine aloe: pale brownish-yellow color Zanzibar aloe: Yellowish brown color
    22. 22. USE • Aloe is purgative; mainly on colon • Ingredient of tincture of Benzoin (friar’s balsam) • In cosmetics
    23. 23. 4. Hypericum • • • • • Syn: St. John’s wort Source: dried aerial parts of Hypericum perforatum Family: Hypericaceae (Clusiaceae) GS: Europe, Central Asia, Himalaya History: flowering on June 24th –St. John’s day o known in ancient Greece for anti inflammatory & healing property o Meaning: hyper: above; icon (eikon)-picture: refers to practice of healing • Constituents: • Anthraquinones: Hypericin ,Pseudohypericin, isohypericin & emodin-anthrone • Use: used in treatment of anxiety & depression, used to lower plasma concentration of the protease inhibitor
    24. 24. 5. Cascara • • • • • Syn: Sacred bark, Chittern bark Source: dried bark of Rhamnus purshiana Family: Rhamnaceae GS: Pacific coast of North america Constituents:  Bark stored for at least 1 year gave galenicals.  During storage its getting hydrolysed & change during storage.  Very bitter taste is reduced by treating it with alkali, alkali earth & magnesium oxide. o 6-9% anthracene derivative (o-glycoside & c-glycoside) o Cascaroside A, B, C, D o Aloin • Use: purgative, used in the form of liquid extract/tablet prepared from dry extract, veterinary work
    25. 25. 6. Andira Syn: Goa Powder Source: lysogenous cavity in the wood of Andira araroba Family: Leguminosae GS: Malabar coast Form: Chrysarobin-a mixture of substance obtained by extraction with hot benzene. • Constituents: Chrysaphanol anthranol (gives strong green fluorescence in alkaline solution), emodin-anthrone-monomethyl ether • Use: keratolytic agent, treatment of psoriasis, trichophytosis, chronic eczema, skin disease • • • • •
    26. 26. 7. Senna • Syn: Senna ki patti • Source: dried leaflets of Cassia angustifolia (Indian-Tinnevelly), Cassia acutifolia (Alexandrian ) • Family: Leguminosae • Description: small shrub; 1 m high • GS: TamilNadu, Africa • Constituents: Sennoside A, BhydrolysisSennidin A,B o Sennoside C,D o Rhein o Aloe-emodin
    27. 27. • • • • • • • • Morphology: Color: Yellowish green Odor : Slight Taste: mucilaginous, bitter, characteristic Shape: Lanceolate Margin: entire Apex: acute Base: asymmetric Indian senna leafs are bigger in size compared to Alexandrian senna. • • • • • Microscopy: iso-bilateral leaf epidermal cells have straight walls, many contain mucilage Both surface: scattered, unicellular, non-lignified trichome Stomata: paracytic; spongy mesophyll; cluster crystals
    28. 28. Cultivation • Soil: red loamy • Sowing period: Feb-March & Oct-Nov • Sowing method: broadcasting (by hand mechanically) • Earlier germination: seed surface is abraded or triturated with sand. • Avoided: High rain & water logging • After 2-3 of sowing • Harvesting: leaves in 3 steps  First Plucking: leaflet thick, green  Second: after 1 month  Third: after 4-6 weeks • Sennoside content maximum at fully grown, decreasing on maturation of pods • • • • • • Collection & Preparation: Period: September Sun Drying: branches bearing leaves & pods Separation by sieves of : pods & large Stalks Tossed: shallow trays Grading of leaves: sieve & hand picking • Whole leaves • whole leaves, whole leave-half leave, • sifting Packed somewhat loosely in bales (cotton or paper)
    29. 29. • Chemical Test: Borntrager’s Test 1. Boil  Drug + dilute H2SO4 2. Filter 3. Add to Filtrate: benzene (or ether or chloroform) 4. Shake well 5. Separation : Organic layer 6. Add to Organic Layer: Ammonia 7. Color: pink-red color ( presence of anthraquinone) • Uses: purgative in perpetual constipation • Allied Species: 1. Dog Senna: Cassia obovata 2. Palth Senna: Cassia auriculata
    30. 30. 8. Rhubarb • Syn: Revandchini • Source: dried rhizomes of Indian - Rheum emodi Chinese - Rheum palmatum, Rhum webbianum • Family: Polygonaceae • GS: South east China, Tiber, Korea, India • Collection & Preparation: • • • • • • • Wild plants, altitude more than 3000 meter, its must for growth. Drought resistant plant; seed propagation by rhizome Obtained from 6-10 year old plant; rhizome portion is dug up in spring or autumn Aerial portion , dies in winter; rhizome remaining in ground regenerate in next spring. Collected rhizomes, cleaned, decorticated and dried. Larger rhizomes are cut Transversely or longitudinally. Pieces are threaded by piercing a hole in them and such threaded pieces are dried under shade.; some of the pieces are artificially dried. • Drug is packed in wooden cases.
    31. 31. • Morphology: o Round pieces are prepared from small rhizomes which are cut only transversely and hence they are barrel shaped. o Shape: cylindrical or Conical; dimension: 8-10 cm length & 4 cm thickness o Odor : Sharp; Taste: astringent; color: yellow surface and pale brown to red in color. o Drug with pink fracture is regarded as high quality drug. o Presence of start spots which indicates abnormal vascular bundle; appears as reddish brown line. • Constituents: Anthraquinone with carboxyl group: Rhein & Glucorhein Anthraquione without carboxyl group: aloe-emdin, emodin, chryasophanol, physcion Anthrones & Dianthrones of alo-emodin, emodin, chryasaphanol and physcion Heterodianthrone: Palmidin A, Palmidin B, Palmidin C Astringent part mainly consists of Gallic acid as glucogallin, tannin, catechin & epicathechin o Rheinolic acid, pectin, starch, fast & Calcium oxalate o o o o o
    32. 32. • Chemical Test: o Rhubarb gives modified Borntrager’s test positive o Rhubarb + alkali  red color (due to anthraquinone glycoside) • Use: Bitter stomachic, treatment of diarrhoea, purgative
    33. 33. Rhapontic rhubarb Source: rhizomes of Rheum rhapontic GS: Southern siberia and surrounding region of Volga river Description: pinkish in color and shrunken in nature Constituents: Rhaponticin-crystalline glycoside, derivative of stilbenediphenyl-ethylene • CT: 1. 0.5 g powder + 10 ml 45% alcohol  for 20 minute shaking occasionally; 2. filter & press 1 drop of filtrate on filter paper 3. Examine under UV light 4. blue fluorescence in UV light • Use: estrogenic activity • • • •
    34. 34. Iso thiocyanate Glycoside • They are called as Glucosinates. • Aglycone part of such glycoside contains isothiocyanate, as it contains sulphur along with nitrogen. • Widely scattered in family Cruciferae, Resedaceae, Capparidaceae. • Contain enzyme Myrosinase
    35. 35. Brassica • • • • • Syn: black or brown mustard, sinapsis Source: dried ripe seeds of brown or black Brassica nigra or Brassica juncea Family: Cruciferae GS: Europe, US, India, USSR Constituents: sinigrin (potassium myronate), myrosin enzyme, o volatile oil, 90% allylisothiocyantae o Seed: 27% fixed oil, 30% protein, o mucilage, sinapine hydrogen sulphate • Use: in the form of plasters, rubefacients counter irritant, in large doses emetic, as an condiment
    36. 36. White brassica • Source: dried seeds of Sinapsis alba • Family: Cruciferae • Constituents: glucoside sinalbin & myrosin. o In presence of moisture decomposition takes place with formation of isothiocyanate, sinapine hydrogen sulphate, glucose o Isothiocyanate: pungent taste, rubefacient property o Fixed oil, protein, mucilage • Use: same as previous 1
    37. 37. Cyanogenetic Glycoside • • • • • • • • • • Also termed as Cyanophore Glycoside Derivatives of mandelonitrile On hydrolysis yields  Benzaldehyde & HCN, this changes Sodium picrate into Sodium purpurate, color changes from yellow to brick-red. Amygdalin  bitter almond Prunasin  wild cherry bark Linamarin  linseed Phaseolunatin  bean, Phaseolus lunatus  hydrolysis  prussic acid First to discover cyanogenetic glycoside Presence or absence of HCN was taxonomic importance and used it as a character for separating the subfamilies of Rosaceae Chemical test: 1. Powder + water  allow to moist • Impregnate strip of filter paper  neck of flask • Treatment of filter paper with o Sodium picrate: yellow  gets converted to sodium isopurpurate (brick-red) 2. Freshly prepared Guaicum resin in absolute alcohol  allowed to dry on filter paper
    38. 38. 1. Wild cherry bark • • • • • • Syn: wild black cherry, Virginian prune bark Source: dried bark of Prunus serotina Family: Rosaceae GS: Canada, US Maximum Pharmacological action during Autumn season. Constituents: prunasin  hydrolysis  glucose + benzaldehyde, enzyme prunase, hydrocyanic acid, benzoic acid, trimethylgallic acid, coumaric acid o Tannin, resin  hydrolysis  scopoletin • CT: 1) HCN liberated on hydrolysis reduces mercurous nitrate to metallic nitrate • Use: syrup-tincture in cough preparation, mild sedative, irritable & persistent cough
    39. 39. 2. Bitter almond • • • • • • • • Syn: Amygdala amara Source: dried ripe seeds of Prunus amygdalus Family: Rosaceae Constituent: chief-Amygdalin, 40-50% fixed oil, 20% protein, enzyme: emulsin Amygdalin  hydrolysis  Benzaldehyde + HCN HCN  very toxic & makes the drug unsuitable for internal consumption Sweet almond do not contain amygdalin Uses: Demulcent, Sedative due to HCN, perfumery industry & flavoring of foods
    40. 40. Napthoquinone Glycoside 1. 2. 3. 4. • • • • • • • Plumbago Henna Alkanna Walnut They are produced by higher plants, fungi & actinomycetes and exhibit broad range of biological activities like fungicidal, antibacterial, insecticidal, phytotoxic and anticarcinogenic In plants, they commonly occur in reduced & glycosidic form of 4-beta-D-glucoside of alpha-hydro-juglone On extraction & work-up or in the soil, compounds oxidatively converted to color compounds like napthoquinone. Biosynthesized by variety of pathway Lawsone by shikimic-succinyl coA combined pathway. Plumbagin by acetate-mevalonate pathway Alkannin by shikimate-mevalonate pathway
    41. 41. 1. Plumbago • • • • • • Syn: Chitrak Source: dried matured roots of Plumbago zeylanica Family: Plumbaginaceae GS: India, Ceylon Constituents: Plumbagin Use: increase digestive power, promote appetite, hypoglycemic, hypolipidaemic, CNS stimulant, in dyspepsia, piles, skin diseases.
    42. 42. 2. Alkanna • • • • • Syn: Alkanet, Anchusae radix Source: dried root of Alkanna tinctoria Family: Boraginaceae GS: Hungary, South europe, Turkey Constituents: alkannin, alkali sensitive ester of angelic acid, alkannan & shikonin • CT: treatment of this extract with hydroxide gives a blue solution from which a dye is precipitated by treatment with acid. • Uses: coloring oils-tars, in tincture for the microscopical detection of oils-tars
    43. 43. 3. Henna Syn: Mehendi Source: dried leaves of Lawsonia inermis Family: Lythraceae GS: North Africa,Egypt, India, Ceylon OH Constituents: lawsone (coloring matter:hydroxynapthaquinone), phenolic glycoside, coumarins, xanthones, quinoids, beta sitosterol glucoside, flavonoids: luteoline o Fats, resin, tannin • Use: dye for hair, wool washed in dilute solution of ammonia and boiled in a decoction of drug, treatment of jaundice, enlargement of the liver and spleen, skin disesease • • • • •
    44. 44. 4. Walnut • Syn: apricot • Source: dried fruits of Juglans regia,-Persian J.cinerea-Butter nuts, J.nigra-black wallnut • Family: Juglandaceae • GS: Asia, America • Constituents: Juglone (5-hydroxy, 1,4 napthaquinone), glycosides of alphahydrojuglone in its reduced form brown dye juglone on extraction and work up. • Use: dyeing wool and cotton to yellowish brown color, although it no longer has any commercial value as a dye. It is fungicide and also finds its use in the treatment of skin disease, sunburn, scalp itching, peeling & dandruff. • Note: used to detect the trace amounts of nickel salts since it gives a deep violet color with such salts.
    45. 45. Biosynthesis • Transfer of a uridylyl group from uridine triphosphate to a sugar 1-phosphate. • Enzymes catalysing reactions are called as referred to a uridylyl transferase and have been isolated from animal, plant and microbial sources. • Glycosyl transferases involves the transfer of the sugar from uridine diphosphate to a suitable acceptor aglycone, thus forming glycoside. • UTP + sugar-1-P ---1--- UDP-sugar + Ppi • UDP-sugar + acceptor ---2--- acceptor-sugar + UDP
    46. 46. Biosynthesis of Juglone Shikimic acid pathway 55-o-succinyl benozic acid, 57-beta hydroxy juglone, 56-juglone
    47. 47. Biosynthesis of Juglone 38-o-succinyl benozic acid, 40-1,4-dihydroxy-2-napthoic acid 41-lawsone 42-1,4-naphthaquinon 43-2-carboxy-4-oxotetralone
    48. 48. Biosynthesis of anthraquinone • By acetate mevalonate pathway or isochorismate alpha ketoglutaric acid -acetate pathway. • Followed by polyketide
    49. 49. Biosynthesis of Aloe-emodin Polyketide biosynthesis
    50. 50. Biosynthesis of Amygdalin • Defense mechanism: ability to produce toxic amounts of HCN, which is extremely toxic to most of the organism as it inhibits cytochrome oxidase and other respiratory enzymes. • Shikimic acid pathway.. Amino acid phenyl alanine. • Amygdalin serves as a phagostimulant for malacosoma americana. • (A natural plant substance that induces feeding by an insect.) • Young fruits only contain prunasin, but after development, the cotyledons contains amygdalin.
    51. 51. Biosynthesis of Amygdalin

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