Post on 01-Jun-2018
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Important Phenols
in Pharmacy:Simple Phenolics
Tannins
LigninsGLYCOSIDES
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Glycosidesa compound that yield one or more sugaramong the product of hydrolysis.
non-sugar
(genin)
sugar
(glycone)
glycosidic
linkage
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General Methods of
IsolationDestruction of hydrolyzing enzymes
De-fating
Extraction
Concentrate the extractives
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General Methods of
IsolationAdd water Filter
AqueousExtract
Treat withOrganic solvent
Add lead acetate
Purified glycosides(crystallization)
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Alcoholic orphenolic
AldehydeAlkaloidal
Anthracene oranthraquinone
Chromone
Coumarin
Cyanogenic
Flavonoidal
Glucosinolates/isothiocyanates(sulfur containing)
Napthoquinone
Steroidal (cardiac
glycosides)
Classification of Glycosides
based on aglycone
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Classification and
Nomenclature1. According to the type of glycosidiclinkage
2.According to the chemical groupofthe aglycone involved into the acetalunion
3. According to the nature of the simplesugarcomponent of the glycoside
4. According to the number of themonosaccharides in the sugar moiety
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O-Glycoside
CH2OH
OH
CH2OH
O-C6H11O5
C6H12O6 +
SugarSalicin
Glycosidic linkage-H2O
C-Glycoside
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N-Glycoside
S-GlycosideCH2 CH CH2 C
S C6H11O5
N OS O3K
Glycosidic linkage
Sinigrin
C6H12O6
Sugar
+ CH2 CH CH2 C
SH
N OS O3K
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5. According to the physiological orpharmacological activity/therapeutic
classification.6. According to the correlation to the
parent natural glycoside
7. According to the plant families
Classification and
Nomenclature
Amygdalin Prunasin R-mandelonitrile
Amygdalinhydrolase
Prunasinhydrolase
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Physical and Chemical
PropertiesPhysical PropertiesMost glycosides are water soluble
and SOLUBLEin alcohols.Insolubleor lesssolublein non
polar organic solvents.More sugar unitsin a glycoside
lead to more solublein polarsolvents.
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Physical and Chemical
PropertiesChemical PropertiesGlycosides do not reduceFehling's solution, but whensusceptible to hydrolysis give reducingsugars (C-glycosides are exceptions).
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Stability and Hydrolytic
CleavageAcid hydrolysis: all glycosides arehydrolyzable by acids.
Acetal linkage is more unstablebetween twoindividual sugars within the molecule
Glycosides containing 2-deoxy sugars aremore unstableeven at room temperature.
C-glycosides are very stable(need oxidativehydrolysis).
Alkali hydrolysis:
Strong alkali or mild alkali
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Enzymatic hydrolysis:Specific for each glycoside; but same
enzyme is capable to hydrolyze differentglycosides.
Emulsin isfound to hydrolysed most-
glycosidelinkages;Maltaseandinvertaseare -
glycosidases.
Stability and Hydrolytic
Cleavage
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Enzymatic hydrolysis:
Stability and Hydrolytic
Cleavage
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Identification Test
Unsaturated Steroidal andtriterpenoidal glycosidesLiebermanns Burchard Test Result: green color/violet-blue
Salkowskistest: yellow colorAntimony chloride test: pink solution
upon heatingTrichloroacetic acid test: colored pptTetranitromethane test: yellow solution
Zimmermann test: violet color
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Identification Test
Chemical tests for cardiacglycosides:
Keller killiani test (presence ofdigitoxose: reddish brown layer whichturns bluish green)
Lejal/Legal test: pink colorBaljet test: yellow to orange colorKedde test: pink color
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Identification Test
Anthraquinone glycosides:+ Borntragers/ Modified
borntragers(C-type)Result: Reddish coloration with alkali
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Coumarin glycosides
Ferric chloride test: deep green whichturns to yellow upon addition of conc.
Nitric acidFluorescence test: blue-green
fluorescence
LeucoanthocyaninsBate Smith and Metcalf Test Method
Strong-red or violet
Identification Test
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Cyanogenetic glycosides - hydrolysishydrocyanic acid tested by change Sodium picrate paper
(yellow) to red color. Sulfur containing glycosides
give black precipitate of silver sulfate upon
treatment with AgNO3solution. Saponin GlycosidesFroth TestAgar Cup Method Hemolytic Test
Identification Test
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Flavonoidal glycosides: Characteristic color with, NH4OH, AlCl3, FeCl3
Alkaline reagent test (ammonia test)
Shinoda test
Vanillin HCl test
Wilstatter Test aka Cyanidin TestWith conc. acid and Mg produces colors ranging
from orange to red, crimson and magenta andoccasionally to green or blue indicates thepresence of benzo-pyrone nucleus.
Identification Test
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Special Test based on thechemical structure
Determination of the glycosidiclinkages: Use of and glycosidases
Optical activity
Color reactions based on the sugar:
Keller Killiani (Test for 2-deoxysugars)
Glacial acetic acid containing + FeCl3+ H
2SO
4brown
ring free from red (acetic acid = blue).
2- Xanthydrol:
xanthydrol in glacial acetic containing 1% HCl + glycoside
[heat]
red color.
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Medicinal importance of
glycosides1. Cardiac drugs:cardiotonic glycosides
e.g: digitalis glycosides, strophanthus, squill
2. Laxatives: anthraquinone glycosidese.g: senna, aloes, rhubarb, cascara, frangula
3. Counter-irritants: thioglycosides and
their hydrolytic products e.g:allylisothiocyanate
4. Analgesics:methyl salicylate a hydrolyticproduct of gaultherin
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5. Anti rheumatic:e.g: salicin.
6. Some glycosides are claimed to reduce the
capillary fragility:e.g: flavonoidalglycosides, rutin, hesperidin
7. Anti-inflammatory:the glycoside
glycyrrhizin has a demulcent, expectorant andantispasmodic action
8. More recently as an anticancer agente.g.,amygdalin known in the U.S. as Laetrile
Medicinal importance ofglycosides
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Simple Phenolic
Compounds Catechol or _______Present in Kola seeds and leaves of
Gaultheriaspp.
The derivatives are the urushiolphenols of the poison oak andpoison ivy
Resorcinol or ________Constitute the narcotic principle of
cannabis
Hydroquinone or _______
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Other phenolics includes:
Eugenol phenolic phenylpropane
Vanillin phenolic aldehydesSalicylic acid
Ferulic acid
Caffeic acid
Study Table 21.1 page 221
Simple Phenolic
Compounds
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CN: Meadowsweet
SN:Filipendulaulmaria; Spirea ulmaria
FN:Rosaceae
Constituents:
Salicylaldehyde
Methylsalicylate
Benzaldehyde
Benzyl alcohol
Use/s:
Diuretic
Traditionally used as
anti-inflammatory,astringent andstomachic agent
Simple Phenolic
Compounds
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Methyl salicylate
Sources:
Gaultheria procumbensGaultheria fragrantissima
Betula lenta
Use/s:Counterirritant
Soothing effect
aka _______________
Simple Phenolic
Compounds
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Willow bark
Salix purpurea (purple)
S. daphnoides
S. fragillis (crack) Constituents:
Salicinphenolic glycosides
Condensed tannins
Isoquercitin, chalcone
Uses:
Anti-inflammatory in the tx ofrheumatism, arthritis and
muscular pains.
Simple Phenolic
Compounds
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Black haw barkViburnum prunifolium
FN: CaprifoliaceaeConstituents:0.2% SalicinTannins/ and resins
Reported use/s:Tx of dysmenorrheaAbortifacientTx for asthma
Simple Phenolic
Compounds
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Hops:Humulus lupulus L. FN: Caprofoliaceae
Constituents:HumulenePhloroglucinol derivatives
humulone, lupulone
Xanthohumol Use/s:Anti estrogenAnti oxidant
Mild sedative
Simple Phenolic
Compounds
i l h li
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Male Fern (Filix Mas)
Dryopteris filix-mas
FN: Polypodiaceae Intact plant possess an
internal green color.
Constituent:
Phloroglucinol
derivatives
Use:
Anthelmintic(tapeworm)
Simple Phenolic
Compounds
i l h li
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Kamala
Mallotus philippinensis
FN: Euphorbiaceae
Constituents:
Phloroglucinolderivative like rottlerin
and isorottlerin
Use:
Anthelmintic
Simple Phenolic
Compounds
i l h li
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Wood tar(Stockholm tar)
FN: Pinaceae
Characteristics:Prepared by
destructive distillation
(methanol, acetone).Blackish semi liquidCharacteristics odor
Use:Tx psoriasis
Constituents:Cresols, Methyl cresolsCathecol/pyrocatechinGuaiacol (methyl
cathecol)Benzene
Toluene
Simple Phenolic
Compounds
Si l h li
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Coal tarPrepared by destructive
distillation of bituminous coal
Characteristics:Black viscous liquidForms alkaline solution withwater.
Petroleum spirit extract has ablue fluorescence enhanced byUV light
Use:Treatment of psoriasis
Simple Phenolic
Compounds
Si l h li
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Vanilla (Vanilla Pods)
Vanilla fragrans
V. planifoliaV. tahitensis
V. pompona
FN:Orchidaceae
Constituents:Glucovanillin
(vanilloside),
glucovanillic alcohol
Vanillin BP
Aldehydecorresponding tomethyl-protocathechuic acid
Uses:
Flavoring agents Coloring agents
Simple Phenolic
Compounds
Si l Ph li
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Bearberry (Uva ursi)Arctostaphylos uva-ursiFN: Ericaceae
Constituent:Arbutin, methyl arbutin, quercitin,
gallic acid, elagic acid, and ursolic acid
Use/s:Urinary AntisepticDiuretic (due to hydroquinone)Astringent
Simple Phenolic
Compounds
Si l Ph li
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Simple Phenolic
Compounds
Si l Ph li
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Capsicum (RedPeppers)
Capsicum annuumC. frutescensFN: Solanaceae
Constituents:CapsaicinRed carotenoids
capsanthin andcapsorubin.
Fixed oils
Use/s:Condiments cayenne
pepper Internally as atonic
dyspepsiaExternally as a counter-
irritant (plaster,ointment)
Used as a relief forrheumatism
Simple Phenolic
Compounds
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Coumarin Glycosides
Derivative of ________ These includes:(1)(2)(3)(4)
Umbelliferone[7-hydroxy coumarin] is thelactone of umbellic acid which occurs both inthe free state and in the form of glycosides in
some resins of the Umbelliferae
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In ammoniacal solution, these compound produceblue, blue-green or violet fluorescence (conjugateddouble bond system).
Study Table 21.2, pg 233
Coumarin Glycosides
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Furanocoumarinsresponsible for the
effect on the drugavailability.
WHY???
Coumarin Glycosides
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Angelica RootsAngelica archangelica L.FN: Umbelliferae
Constituents:FuranocoumarinsBergaptenAngelicinArchangelicinApterinMarmesin and psoralen
Use/s: Potent coronaryvasodilator effects Calcium antagonist
Coumarin Glycosides
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Coumarin Glycosides
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MelilotMelilotus officinalis
FN: LeguminosaeConstituent/s:Coumarin derivatives
Melilotic acidCaffeic acid
o-Coumaric acid
new-mown hay odor
Coumarin Glycosides
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Tonco seedDipteryx odorata andD.
oppositifoliaFamily Name: Leguminosae
Constituents:
1 3% coumarinUse/s:
Tobacco manufacture and
perfumery
Coumarin Glycosides
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Celery fruitApium graveolens
Family Name: Umbelliferae
Constituent/s:
Coumarin and phenolic glycosides
Furanocoumarins Use/s:
Tx of rheumatic disease
Coumarin Glycosides
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A th i
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Anthraquinone
Glycoside Stimulant cathartic exert their action by increasing
the tone of the smooth muscle in
the wall of the colon andstimulate the secretion of waterand electrolyte into the largeintestine.
Stimulant laxativehabit forming, may result to
laxative dependence and loss of
normal bowel function.
A th i
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Anthraquinone
GlycosideO
O
1
2
3
45
6
7
8
9
10
O
H H
1
2
3
45
6
7
8
9
10
OH
H
O
H OH
12
3
45
6
78
9
10
Anthraquinone
Oxanthrone
Anthrone Anthranol
4H
2H
Types of
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Types ofAnthraquinone Glycosides
O-glycosideswhere the aglycone moiety is 1,8dihydroxyanthraquinone derivatives
T f
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O-glycosidewhere the aglycone moiety partiallyreduced 1,8 dihydroxy anthraquinone, e.g.,Oxanthrone-type.
OH OH
O
H O
2
3
45
6
7 9
10
Gl
8 1
Emodin-oxanthrone-9-glucoside
Types ofAnthraquinone Glycosides
T f
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C-glycosidewhere the aglycone structure(anthrone derivative)
OH
CH2OH
OHO
H C6H11O5
2
3
5
6
7 9
10 4
8 1
Barbaloin
Types ofAnthraquinone Glycosides
T pes of
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O-glycosideswherethe aglycone moiety is
di-anthrone derivative(a dimer)e.g.,Sennosides where there
is C-Cbridge betweenthe anthranol units.
Sennoside A&B
Types ofAnthraquinone Glycosides
Offi i l th i
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Official anthraquinonedrugs in B.P and U.S.P.:
Senna leaf & senna fruit (pod)
Aloes
Cascara tablets, elixir, dry exract, liquidextract
Rhubarb powdered, tincture
Danthrone Frangula bark
d
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Cascara SagradaRhamnus purshianus DecandolleFN: Rhamnaceae aka sacred barkCathartic used in the correction of habitual
constipation;Obtained by percolation and evaporation;Bitter taste and activity may be reduce by treating
extract with alkaline earth or Magnesium oxide
Casanthranolpurified, watersoluble mixtureof anthranol glycosides extracted from cascarasagrada
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Cascaroside A & B:optical isomers of barbaloinCascaroside C & D:optical isomers of chrysaloin
Cascara Sagrada
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Two aloins (secondary glycosides):Barbaloin derived from (C-10-C-glycoside) of
aloe-emodin anthrone
Chrysaloinderived from (C-10-C-glycoside)of chrysophanol anthrone.
Cascara Sagrada
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O- glycosides:derived from emodin, emodine oxanthrone, aloe
emodin and chrysophanol.
Cascara Sagrada
Frang la (B ckthorn
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Frangula (BuckthornBark)
Rhamnus frangula Linne
FN: Rhamnaceae
Constituents: Frangulins A & B,glucofrangulins A & B
It should be aged 1 year to reduce harsh
action of the glycosides to a milder form Frangulin (frangula emodin rhamnoside)
Glucofrangulin (frangula emodin
glucorhamnoside)
Frangula (Buckthorn
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Frangula (BuckthornBark)
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Aloe or Aloes
Aloe barbadensis Miller
(Curacao aloe)
AloeferoxMiller (Cape aloe)
Aloe africana Miller
Aloe spicata Baker.
FN: Liliaceae
Reddish black or brownishblack with nauseating and
bitter taste and disagreeable
characteristic odor.
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Dried latex of the leaves ofAloebarbadensis
Constituent/s:
Aloin A (Barbaloin)
Aloin B (Isobarbaloin)
A pharmaceutic aid for Compound
Benzoin Tincture
Use: Cathartic
Aloe or Aloes
Rhubarb aka Rheum/
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Rhubarb aka Rheum/Chinese Rhubarb
Rheum officinale Baillon
Rheum plamatumLinne
FN: Polygonaceae
Constituent:
Rhein anthrones
Use:
Drastic cathartic action(purgative)
Indian rhubarb aka
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Indian rhubarb akaHimalayan rhubarb
Rheum emodiWallion
Rheum webbianum Royle
FN: Polygonaceae Constituents:
Rhein, rhein anthrone, chrysophanol and
aloe emodin.Dianthrones of heteroanthrone types are
palmidin A,B,C, rheidins, sennosides A&B
and their oxalate esters (sennosides E&F).
Indian rhubarb aka
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Tannins present inrhubarb makes the drugconstipating.
Small doses: no purgativeaction but acts as
intestinal astringent, Large doses: purgation
Indian rhubarb akaHimalayan rhubarb
S /S l
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Senna/Senna leaves
Cassia acutifoliaDelile Alexandria orCassia Senna
Cassia angustifoliaVahl Tinnevelly
Senna FN: Fabaceae
Constituent:
Sennosides A and Brhein dianthrone(Sennidin A+B)
Use/s:Purgative (liquid extract, elixir or as
tablets prepared from dry extract)
S /S l
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Dianthrone
Only compound which is used tosome extent in current medicine
Used as standard in colorimetricassays of anthraquinoneglycosides.
Some of these syntheticcompounds act too drastically andalso caused kidney damage.
OH OHO
O
Anthrone
Senna/Senna leaves
S /S l
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Homo-dianthrones vs. hetero-dianthrones
O O
H
COOH
OH
O OH
COOH
O
H
2
3
5
6
7 9
10 4
8 1
Gl
Gl
Sennosides A &B
Senna/Senna leaves
O O
H
COOH
OH
O OH
CH2OH
O
H
2
3
5
6
79
10 4
8 1
Gl
Gl
Sennoside C&D
i d
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Cassia podsDried ripe fruits of Cassia fistulaFamily Name: Leguminosae
Constituents:
Rhein, ennidins and sennosides Aand B (leaves)
Barbaloin, rhein andleucoanthocyanidin (heartwood)
Use/s:
Laxative
h bi
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ChrysarobinA mixture of araroba or goa powder
and extracted with hot benezene
Araroba (Andira araroba)
Family name: Leguminosae
Constituent/s:
Chrysophanol anthranolUse/s:
Formerly used for skin disease
dd
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MadderFrom the root ofRubia tinctorumFamily: Rubiaceae
Constituents and use:Ruberythic acid that yieldsalizarin and primeverose upon
hydrolysisUsed as a dye but replaced by
synthetic dyes
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St. Johns WortHypericum perforatum Family: Clusiaceae
Constituent/s:
Hypericin and pseudohypericinIso-hypericin, emodin-anthrone
Prenylated phloroglucinol derivatives
Use/s:Anti-depressant
Tagged as natures Prozac
C hi l
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CochinealFrom dried female insectDactylopius
coccus, egg and larvae
Constituent:
Carminic acid (10%)Use/s:
Colorant/ indicator
Remember the following
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Primary glycosides: more active thanaloins;
Free anthraquinone: little purgative
activityC-C glycosides of aloins:very resistant
to hydrolysisand are not easily
hydrolyzed
Remember the following
for anthraquinoneglycosides:
SAR of Anthraquinone
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Glycosylation
Hydroxylation (C-1, C-8) Oxidation (C-9, C-10)
SAR of AnthraquinoneGlycosides
SAR of Anthraquinone
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The nature of substances at C-3:Derivative with CH2OH (as in aloe
emodin) are more active than those withCH3substitution. The latter more activethan derivative with COOH substitution atC-3.
Anthraquinone glycosides containing adimer is more active than a monomer.
SAR of AnthraquinoneGlycosides
SAR of Anthraquinone
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Effect of storage on the active ofanthracene glycosides:
Long storage bring oxidation ofanthranols and anthrones to give the lessactiveanthraquinones.
Anthraquinone glycosidesdo notcause any griping action (like anthranoland anthone), thus no antispasmodic suchasbelladonnais prescribed with them.
SAR of AnthraquinoneGlycosides
Properties of
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Properties ofAnthraquinone derivatives
Extracted and hydrolyzed by boiling withacids.
Aglyconesare extracted from the acidicsolution with ether or benzene.Upon shaking the ether or benzene layer with
aqueous alkali or ammonia solution, theaqueous layer assumes a deep red color, becauseof the formation of anthraquinone salts.
Naphthoquinone
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NaphthoquinoneGlycosides Produced by higher plants, fungi
and actinomycetes Use/s:Fungicidal, antibacterial, insecticides,
phytotoxic, cytostatic and anticarcinogenic
Juglans regiaFN: Juglandaceae4-D-glucoside of hydroguglone (leaves ofwalnut tree)
Naphthoquinone
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Synthesized via:Acetate and malonate pathway
Plumbagin (Plumbagospp)Shikimate/Succinyl CoA combined
pathway LawsoneShikimate/Mevalonate combined
pathway - Alkannin
NaphthoquinoneGlycosides
Naphthoquinone
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HennaLawsonia inermis FN: Lythraceae
Constituent/s: Lawsone (hydroxynaphthoquinone)
colorant Isoplumbagin anti-inflammatory
Use/s: hair dye astringent (stem-bark) Tx for jaundice, enlargement of the liver
and spleen
Tx for skin diseases
NaphthoquinoneGlycosides
Naphthoquinone
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Lithospermumsspp. (Family Name:Boraginaceae)
Reported hormonal activities
Shikonin naphthoquinone derivative
Scyllitol cyclitol
Cyanoglucoside lithospermocide
Use Purple roots tx burns, inflammation,wounds and ulcers
Lithospermum arvense (L. rudelare) oralcontraceptive agents, suppress estrus cycle.
NaphthoquinoneGlycosides
Naphthoquinone
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Alkana root(Alkanet/Anchusae radix)
Alkanna tinctoria
FN:Boraginaceae
Constituent & use:
Alkannin - Red
naphthoquinones
NaphthoquinoneGlycosides
Chromones and
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Chromones and
xanthones Structural derivative of benzo-pyroneChromones: iso form of coumarins ex:
eugenin from ___________.
Xanthonescame from the family _______,________, _______ and ________.
Reported use/s:
Anti-inflammatoryCNS stimulant/depressant
What is the complex xanthones present onmycotoxin pigment of ergot?
Fl id l Gl id
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Flavonoidal Glycosides
Largest group of naturallyoccurring phenols
It includes anthocyaninand
leucoanthocyanin Flavonoidals constitute the
majority of the
colored plant pigments Many flavonoidal compounds
present as a glycosidic or as a
free forms.
Flavone nucleus
Neoflavonoid nucleus
Fl id l Gl id
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Derived from flavan (2-phenyl-benzopyran), have abasic C-15 skeleton
Classes/types:
Flavones (2-phenyl chromones)
Isoflavones (3-phenyl chromones)
Flavonols
flavanones(true flavanoids) 2,3-dihydro
derivatives of flavonesAnthocyanidins
Chalcones
Aurones
Flavonoidal Glycosides
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Fl id l Gl id
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Chalconeshave nocentral pyrone ring
not true flavonoidal compounds.
chemically phenyl-styryl ketone, orbenzylidene acetophenone
Aurones
are oxidized form, obtained by
enzymatic oxidation.have five membered ring
(instead of the central pyronering)
Flavonoidal Glycosides
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Properties of Flavonoids
Dissolve in alkalis give intense yellow colorsolution, on the addition of acid becomecolorless
Exhibit strong fluorescence under UV light Soluble in water and alcohol. Ethylacetateis the solvent of choice for
the extraction of flavonoids from aqueoussolution
Fl id l Gl id
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HesperidinOccurs in various citrus fruits
Found in the root bark of rasaceous plants
Rutin Rutaceae Vitamin P
Flavonoidal Glycosides
Fla onoidal Gl cosides
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Flavonoidal Glycosides
Buchu leavesBarosma crenulata
FN: Rutaceae Constituent/s:
Diosmin - flavoneglycoside
Use/s:
Diuretic and diaphoreticaction
Flavonoidal Glycosides
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O
OH
O
O
OH
OCH3
A
B Rha-Gl
Upon hydrolysis, diosmin yields _______,________and ________.
Flavonoidal Glycosides
Flavonoidal Glycosides
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Rutin and quercetrin (flavonol glycosides)Rutinoccurs in the leaves of buckwheat. It is the 3-rhamnoglucoside (called rutinose)of
the genin quercitin. It gives on hydrolysis the aglycone (quercitin)beside one molecule of glucose, and one moleculeof rhamnose.
Rutinis used to decrease capillary fragility; It is a biflavonoids that plays a true vitamin
function.
Flavonoidal Glycosides
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Flavonoidal Glycosides
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O
OH
O
O
OR
OH
OHA
BH
Quercetin: R=H
Quercetrin: R= rhamnosyl
Rutin: R=rutinosyl
Flavonoidal Glycosides
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Flavonoidal Glycosides
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O
OH
O
O
OH
OCH3AB
R
Hesperitin R:H
R:rutinosyl Hesperidin
Flavonoidal Glycosides
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Flavonoidal Glycosides
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HO
OH
OH
O
O
O
O
OO
Genisteinshow significantestrogenic activity.
Rotenoidsemployed as insecticide
Flavonoidal Glycosides
The leaves and fruits ofSilybum
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ymarianumfamily
Compositae containsilymarin.
OH
OH
O
O
OH
O
O
A B
OH
OCH3
OHSilybin
Silymarin
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Silymarin Effective lipotropic and hepato-protective
therapy; It is a free radical scavenger (anti-oxidant)
Supportive treatment of acute and chronicalcoholic poisoning and toxin induce hepatitis; It is used for treatment of liver cirrhosis causedby plant toxins (mushroom, amanita), silymarin
IVAvailable in the market in the form of tablets,
effervescent granules.
Trade name: Legalon
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Birch
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BirchBetula pendula FN: Betulaceae
Constituent/s:
GlycosidesFlavonoids
Fixed oils
Anthocyanidin
Use/s:Tx of melanoma
Calendula/Marigold
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Calendula/Marigold
Calendula officinalis FN: Compositae
Constituent/s:
FlavonoidsTriterpenoids
Essential oils
Several polysaccharide
Use/s:
Tx of GIT disorder
Tx of minor wounds and rashes
Elder flower
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Elder flower
Sambucus nigra FN: Caprofoliaceae Constituent/s: Semi-solid volatile oil
FlavonoidsTriterpenes Sitosterol
Use/s:Tx of common coldAntipyreticDiaphoretic
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Java Tea
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Java Tea
Orthosiphon staminus FN: Laminaceae
Constituent/s:
Flavonoids
Diterpene
Phystosterol
Use/s:
Anti-hypertensive agent
Anti-diabetic
Tx of several GIT
disorder
Lime flower
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Lime flower Tilia odorata Tiliaceae Constituent/s:Fixed oils
FlavonoidsPhenolic acidMucilages (gums)
Use/s:
Tx for headacheAnti-spasmodic IndigestionNerve tonic
Motherwort
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Motherwort
Leonorus cardiaca FN: Laminaceae/Labiatae Constituent/s: Stachydrine
Flavonoids IrioidsTanninsTriterpenoids
Use/s:Tx dysmenorrheaCDV diseaseNervous tension
Olives leaves
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Olives leaves
Olea europea
Oleaceae
Constituent/s:
RutinOleorutin
Olive oil
Use/s:Tranquilizer
Anti-septic
Astringent
Passiflora
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Passiflora
Passiflora incarnata Passifloraceae
Constituent/s:
Flavonoids
Alkaloids
Volatile oils
Cyanogenetic
glycosides Use/s:
Anxiolytic
Spiny Restharrow
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Spiny Restharrow Ononis spinosa Leguminosae/Papilionaceae Constituent/s:
Isoflavones Tannins Lectins TriterpenoidsVolatile oils
Use/s: DiureticAnti-inflammatory Tx for the removal of kidney and
gallstones
Buckwheat
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BuckwheatFagopyrum esculentum Polygonaceae
Constituent/s:
Rutin Use/s:
Tx of varicose veins,childbalins
Retinal bleeding
Anthocyanidin and itsl id
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Glycoside
Anthocyanidinsare flavonoidsstructurally related to flavones.
Anthocyaninsglycosides of
anthocyanidins Etiology: anthoflower & kyanosblueAnthocyanidins and its glycosides
responsible for the permanent blue, purple,violet, mauve, and red color of flower, fruitsand leaves of higher plants
aka __________
Anthocyanidin and itsGl id
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Anthocyanidin Occurrence ofglycosides
Pelargonidin Flowers of Pelargonium and
pomengranateCyanidin Cornflowers, red poppies,
Rosa spp., cocoa and cherries
Peonidin Peonyl (Ranunculaceae)
Delphinidin Delphinium and Viola spp.
Petunidin Petunia spp.
Malvidin Malva spp.
Glycoside
Anthocyanidin and itsGl id
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Cyanidin
chlorideis an example ofanthocyanidins
Glycoside
Leucoanthocyanin
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y
Upon hydrolysis yields sugar andleucoanthocyanidin
Plant materials boiled with dilutedacids gives intense red or violet color
Lignans and Lignins
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Lignans and Lignins
Dimeric compounds formed essentially by theunion of 2 molecules of phenylpropene derivatives.
Optically active; arise by stereospecific, reductivecoupling between the middle carbons of the side-chain monomer
Podopyllumsppformed by 2 molecules ofconiferyl alcohol and corresponding acid.
Neolignans- derived same as lignans, but theC6-C3moieties are linked head to tail or head tohead and not through -carbons.
Lignans and Lignins
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Source Lignans Type of lignans
Guaiacum officinale -Guaiaconic acid A furano type lignansMyristica fragrans(Nutmeg)
Macelignans A dibenzylbutane-type
Piper cubeba (Tailed pepper) (-)-Cubebin A tetrahydrofuran-type
Podophyllumspp. Podophyllotoxin Aryltetralin typeSchinsandra chinensis Wuweizisu C Dibenzocyclooctadiene
type
Silybum marianum Silybin Flavonolignans
Urtica dioica (Nettle) Neo-olivilderivative
Tetrahydrofuran
Viscum album (Mistletoe) Eleutheroside E Tetrahydrofuran
Zanthoxylum clava-hercules (+)-Asarinin Tetrahydrofuran
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Saponin Glycosides
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Saponin Glycosides
Forms colloidal solution in water that foamsupon shaking, colorless and optically active.
Have bitter, acrid taste; irritating to themucous membrane; destroy red blood cellby hemolysis and are toxic especially tocold-blooded animalsSapotoxin-poisinous saponin used for
controlling schistosomiasis snails.2 types of sapogeninSteroidal-in monocot families
Triterpenoidal- in dicot families
Saponin Glycosides
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Saponins are a group of amorphous colloidalglycosides which is widely distributed in thehigher plants.
They are excellent emulsifying agents(modify surface tension).
Formerly used as detergents to replace soap
(e.g., quillaia). NOTE: very difficult to purify
Saponin Glycosides
Saponin Glycosides
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Chemically:Saponins are classified according to the
genin part into:
Steroidal type C25.Triterpinoidal type C30.
Both types of saponins have the glycosidic
linkage at position 3.
Saponin Glycosides
Saponin Glycosides
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HO
O
O
HO
R1
R2
COOH
DiosgeninQuillaic acid: R1=CHO, R=OH
Olianolic acid R1=CH3, R2=H
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O
OH
O
CO
OH
CH3
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O
Testosterone
HO
O
O
Diosgenin
O
O
CO
OH
CH2OH
Cortisone
O
Progesterone
Medicinal importance of
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Saponins increasethe rate of absorption ofmany pharmacological active substances
(e.g., cardiac glycosides). Many saponin-containing drugs are used as
expectorants (e.g., Ipecac, Senaga and
liquorice) as their contents of saponinsstimulate bronchial secretionand alsoactivate the cilliary epithelium of thebronchi.
saponins
Medicinal importance of
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The triterpenoidal saponin glycoside,glycyrrhizin,is the main sweet principle
of liquorice it is also useddemulcent,expectorant and antispasmodic action.
It is calcium and potassium salts of
glycyrrhizic acid, which in tern is thediglucuronic acidglycoside ofglycyrrhitinic acid.
saponins
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Saponins drugs OfficiallyB P and U S P:
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B.P and U.S.P:
Quillaia bark: used asemulsifier
Liquorice root: used as
flavoring agent andexpectorant
Glycyrrhiza (Licorice)
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root) Glycyrrhiza glabra Linne (Fabaceae)Glycyrrhizin-50x as sweet as sugar but once
converted to its algyone glycyrrhetic acid its
loses its sweetness Use/s:Demulcent, expectorant, increase fluid
retention.
Glycyrrhetic acid- used in dermatologicalpractice as anti inflammatory.
Licorice root extract- use in the tx of peptic ulcer& Addisons disease.
Ginseng
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G se g
Panax quinquefolius Linne (American ginseng)P. ginseng(Asian ginseng) Constituent/s:Ginsenosides, panaxoside and
chikusetsusaponins
Use/s:Tonic, stimulant, diuretic and carminative,
adaptogenic (anti stress) in the Orient-anemia,diabetes, insomnia, neurasthenia, gastritis andsexual impotence
Ginseng
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American ginsengAsian ginseng
Ginseng
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Cyanogenic Glycosides
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y g y
aka __________Yields ______ upon hydrolysis, benzaldehyde and
sugars
Plant containing these glycosides are toxic
The aglyconepart is a derivative ofbenzaldehyde cyanohydrinof a carbonylcompound (condensation product of HCNwith an
aldehyde or ketone); Detected with Guignardsreagent gives yellow
to maroon;
Picrate paper test brown to brick red color
Cyanogenic Glycosides
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C
O
H
CHCN
OH
CN
H
Benzaldehyde Mandilonitrile
SugarsMandilonitrile glycosides
C
CH3
CH3
O C
CH3
CH3
OH
CN
HCN Sugars
Linamarin
C
CH3
CH3CN
O-Gl
Acetone Acetone cyanohydrin
y g y
Amygdalin (D-Mandelonitrileti bi id )
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gentiobioside)
Amygdalinis the most widely distributedcyanophore glycoside.
Amygdalin- in Laetrile or vitamin B17
claimed to be anticancer and control sicklecell anemia.
It occurs in severalPrunusspecies, and isobtained from bitter almonds (Prunusamygdalusvar. amaraFamilyRosaceae).
C
CN
O
O
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Amygdalin
OH
CH2OH1
23
4
5
61
23
4
5
CH2
O
6
O H
C
CN
1
23
4
5
O
O HCH2OH
6
Prunasin
Cyanogenic Glycosides
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Acid hydrolysis of amygdalin split two moleculesof glucose and one molecule of mandelonitrile. Thelatter decomposes spontaneously to formbenzaldehyde and HCN.
Different enzymes act upon amygdalin in differentways:
CGl-Gl-O CN
H
Amygdalin
Amygdalase
Prunase
Emulsin
or acid
Glocose + PrunasinPrunase
Glucose + HCN +Benzaldehyde
Gentiobiose + Benzaldehyde + HCN
Glucose + Benzaldehyde + HCN
y g y
Wild cherry
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Wild black cherry treePrunus virginianaPrunus serotina Ehrhart (Rosaceae) Constituent:Prunasin- formed by partial hydrolysis of
amygdalin;Prunase, p-coumaric acid
Use/s:Sedative, reported
anticancer
Apricot pits
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p p
Prunus armeniaca linne.(Rosaceae)
Contains amygdalin and
emulsin Emulsin- an enzyme that
hydrolyzes glycosidereleasing toxic cyanides
Not use for tx cancerbecause of its potentialdanger.
Enzymatic hydrolysis of
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Amygdalin Prunasin R-mandelonitrile
Mandelonitrile lyase
Benzaldehyde+ HCN + Glucose
Amygdalin
hydrolase
Prunasinhydrolase
Enzymatic hydrolysis of
Amygdalin
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IsothiocyanateGl id
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Importance in treatment of cancer:Mustard: idole 3-carbinol derived
from indolylmethyl glucosinolatereduce risk of estradiol- linkedmammary cancer
Brocolli: 4-methyl sulfinylisothiocyanate induce carcinogenicprotective enzyme.
Glycosides
IsothiocyanateGl id
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The glycosides and theirspecific enzymes are found indifferent cellin the seeds.
They do notinteract untilthey are brought together bythe distruction of the cell
walls. The general structure of
thioglycosides is:
R C
S-GL
N-OSO3
-
X+
Glycosides
IsothiocyanateGl id
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Glycosides
IsothiocyanateGl id
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Sinigringives upon hydrolysis, glucose,
allylisothiocyanate (volatile oil of
mustard) and potassium acid sulfate.
Glycosides
IsothiocyanateGl id
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Hydrolysis of the glycoside sinalbingives a phenolicisothiocyanate (Acrinyl isothiocyanate), glucose andthe acid sulphate of a quaternary alkaloid, sinapine.
HO
CH3O
CH3O
CH-CH-COO-CH2-CH2-N
CH3
CH3
CH3
Sinalpine cation
+
Glycosides
IsothiocyanateGl id
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Black and whitemustard seeds areused as rubefacientsand counterirritants.
These effects are
attributed to theircontents ofthioglycosides.
Glycosides
Isothiocyanate Glycosides/Glucosinolates
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Glucosinolates
Major role in plants:Feeding deterrents against insect and mammals
Sulfur- Atom: Brassicaceae
Reported to have anticancer propertyindole 3-carbinol derived fromindolylmethyl glucosinolate reduce the
risk of estrogen linked breast cancer. Methylsulfinyl isothiocyante induce
anticarcinogenic protective enzymes
Black mustard
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Sinapis nigra or brown/blackmustardBrassica nigra Linne KochBrassica junceaLinne
czerniaewBrassicaceae
Constituent/s:Sinigrin- mustard oil S=C=N-CH2-CH=CH2
Use/s:Local irritant & emetic
Hydrolysis of Sinigrin
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Sinigrin Allyl isothiocyanate (mustard oil)myrosinase
+ glucose + H2SO4
y y g
White mustard
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Brassica albaHookerfillius
FN: Brassicaceae
Sinapis alba Sinalbin upon hydrolysis
by enzyme Myrosinaseyields p-hydroxybenzyl
isothiocyanate
Garlic (otherorganosulfur drugs)
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organosulfur drugs)
Allium sativumline
Family Name: Liliaceae
Alliin [(+)-S-allyl-L-cysteine sulfoxide]Comes with contact with enzyme alliinase when
garlic cells are crushed and is converted toAllicin (diallyl thiosulfate)
Allicin- has potent antibacterial effect, antihyperlipidemic and inhibits platelet aggregation.
Alcohol GlycosidesCH2OH
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y
Salicin (salicyl alcohol)Species ofSalixandPopulusSalix pupurea andSalix fragilis
FN: Salicaceae
Salicin is classified as:
Alcoholic glycoside, as it contains freeprimary alcoholic group.A phenolic glycoside, as its aglycone is
phenolic in nature.
OGl
Properties of Salicin
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Principal commercial source isSalix fragilis. Salicin is used for many years as a remedy in the
treatment of fever and rheumatism.
Now used as an analgesic-antipyretic in case of
periodic fever.
Better tolerated in the stomach than sodiumsalicylate, asprin and other antipyretics and anti-
inflammatory agents, which have largely displacedin medical practice.
Salicin is hydrolyzed by the enzyme emulsin intosaligenin (Salicyl alcohol) and glucose.
Properties of Salicin
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Acid hydrolysisof salicin gives glucoseand aphenolicethercalled saliretinwhich is acondensation product of two molecules ofsaligenin. CH2OH
OGl
Enzyme
Acid
CH2OH
OH
Saligenin
+ Glucose
CH2OH
O
CH2OH
Saliretin
+ Glucose
Aldehyde Glycosides
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Vanilla aka vanilla beanMexican or Bourbon Vanilla- Vanilla planifoliaAndrews (FN: Orchidaceae)
Tahiti Vanilla- Vanilla tahitensis J.W Moore
Constituent/s:Glucovanillin (avenein) and glucovanillic alcohol
Glucovanillin is a glycosidal constituent of greenvanilla pods.
Aldehyde Glycosides
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Vanillin is widely used as a flavoring agent. It maybe obtained fromvanilla podor prepared fromthe glycoside coniferin, lignin or from thephenolic volatile oil constituents eugenol.
CHO
OCH3
O-Gl
CHO
OCH3
OH
Glucovanillin Vanillin
Vanillin from ConiferinCH=CH-CH2OH CH=CH CH OH
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OCH3
O-Gl
CH=CH-CH2OH
OCH3
CH=CH-CH2OH
OH
Coniferin Coniferyl alcohol
OCH3
OH
CHO
Vanillin
Hydrolysis Oxidation
OCH3
CH2-CH=CH2
OH
OCH3
OH
CH=CH-CH3
OCH3
OH
CHO
Vanillin
OxidationKOH
Eugenol isoeugenol
Vanillin from Eugenol
Aldehyde Glycosides
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The bulk of vanillin which is produced commerciallyis prepared from lignin, which gives uponhydrolysis coniferyl alcohol.
Ligninis obtained in extremely large amounts as a by
product of timber industry.
LigninHydrolysis
coniferyl alcohol
Cardiac Glycosides
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Steroidal in character with CPPP nucleus. Powerful action on the cardiac muscle:
increase muscle contractility or tone ofcardiac muscle.
Steroid aglycones:Cardenolides/ C23 steroid/ 5 member lactone
ring.Bufadenolides/ C24 steroid/ 6 member lactone
ring.
Cardiac Glycosides
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Identification Test:Keller Killiani 2-deoxy sugar; reddishbrown color turn to blue purpleLiebermann Burchard steroid; blue green
to pink purple or violet;Kedde test - lactone unsaturated; purple.
Digitalis or Foxgloves
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Digitalis purpurea Linne.
FN: Scrophulariaceae
Most medically important
glycosides Constituent/s:
Digitoxin
Gitoxin
Gitaloxin
Animal used in the assay:guinea pig, frog, cats, pigeon.
Grecian Foxglove
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Digitalis lanata Ehrhart
FN: Scophulariaceae
Source of digoxin 5 types of primary
glycosides:
lanatosides A to E(diginalids)
Lily of the Valley
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Convallaria majalisLinneFN: Liliaceae
Dried rhizomes and roots:
Principal glycosides:Convallatoxin
(strophanthidin andrhamnose)
Minor glucosides:Convallataxol and
Convalloside
Black Indian Hemp
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aka Dog bane/ Canadian hemp
Apocynum cannabinumLinne
FN: Apoynaceae
Dried rhizomes and roots
Principal constituents: cymarin
Other constituents:apocannosides and
cyanocannoside, adonotoxin, K-strophanthin.
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Black Hellerebore/Christmas rose
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Christmas rose
Dried rhizosomes androot of Helleborusniger Linne
(Ranunculaceae).
Possesses cardiac
stimulant properties incontrast to GreenHellebore
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Strophanthus
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Dried, ripe seed ofStrophanthus kombe
Oliver
Strophantus hispidus FN:Apocynaceae
Principal constituent:
K-strophanthoside(stroposide)
Strophanthidin
Strophanthus
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gratus From seed ofStrophanthus gratus
Wall et Hook. Baillon or from wood
ofAcokanthera spp.
FN: Apocynaceae
Ouabain aka
G-strophanthin
extremely poisonous
Squill/ Squill bulb
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Dried, fleshy, inner scales of the bulb of thewhite variety of Urginea maritime LinneBaker or Urginea indicaKunth (Liliaceae)aka Mediterrian Squill respectively
Principal constituent: scillaren A.
Minor constituent:
glucoscillaren Aproscillaridin A.
Uses: expectorant, emetic, cardiotonic and diuretic.
Red squill
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Bulb or bulb scales ofred variety of Urgeneamaritimelinne Baker
(Liliaceae)
Use: rat poison
The CPPP Nucleus
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O
R
OH
CH3
Sugar
Lactone ring
1
2
3
45
10
67
8
9
11
12
13
1415
16
17
Cardiac Glycosides
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The genins of all cardiac glycosides aresteroidal in nature, that act as cardiotonic
agents.
They are characterized by their highly specific
action cardiac muscle, increasing tone,
excitability and contractility of this muscle,
thus allowing the weakened heart to function
more efficiently.
Cardiac Glycosides
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Cardiac glycosides that - unsaturated5-membered lactose ring in position C-
17 are known as cardenolides.
Represented by the digitalis andstraphanthus group.
Cardiac Glycosides
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Digitalis glycosidescontain angularmethyl group at C-10,
Strophanthus glycosideare
characterized by presence of either analdehydic(CHO) or primaryalcoholic(C`H2OH) group at C-10.
O OCardiac Glycosides
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O
R
OH
CH3OH
Sugar
1
2
3
45
10
6
7
8
9
11
12
13
1415
16
17
CardenolidesDigitalis glycosides R=CH3Strophanthus glycosides R=CHO OR CH2OH
Cardiac Glycosides
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Cardiac agents that havedoubly unsaturated 6-membered lactone ring in
position C-17 are referredto as Bufadienolides.
This group includes thesquill glycosides and thetoad venom, Bufotoxin.
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Cardiac Glycosides
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Digitoxose Cyamarose Thevetose
Isolation difficulties
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Major difficulty in the isolation of primaryglycosides from the crude drug...
Why?
The Cardenolides Digitalis Group
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g p
D. purpurea, D. lanata, D. lutea and D. thapsi
O
OH
R1
R2
H
1
2
3
45
10
6
7
8
9
11 13
14
15
17
O O
12
16
The structures of the common aglycones of the digitalis group
The Cardenolides Digitalis Group
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The primary glycosides Lanatoside A,Lanatoside B, Lanatoside Care acted byspecific enzymewhich split the terminalglucose, give the secondary glycosidesacetyldigitoxin, acetylgitoxin andacetyldigoxin respectively.
The deacetyl-lanatosides A, B and Ccan be
obtained by the alkaline hydrolysisof thecorresponding lanatosides.
Digitoxin, gitoxin and digoxinare obtained bythe action of alkalion their acetyl-derivatives.
g p
The Cardenolides Digitalis Group
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Lanatoside A
Alkalinehydrolysis
Specific
enzymeAcetyldigitoxin
Specificenzyme
Alkaline
hydrolysis Digitoxin
Digitoxigenin + 3 digitoxose
Acid hydrolysis
purpurea gly. A
g p
Strophanthus Group
Gl id K h h id ( i id )
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Glycoside K-strophanthoside (a trioside),K-strophanthin B (bioside) and cymarin (amonoside) were isolated from differentstrophanthus species.
The Primary glycoside K-strophanthosidegives by hydrolysis one molecule of glucose
and the secondary glycoside K-strophanthoside B or K- strophanthin B.
Strophanthus Group
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The later gives by hydrolysis one moleculeof glucose and the tertiary glycosidecymarin, which on turn hydrolyze into the
genin K-strophanthidin and the deoxysugarcymarose.
O O
Strophanthus Group
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O
CHO
OH
OH
1
2
3
4
10
6
7
8
9
11 13
14 15
17
O O
12
16
5
K- strophanthidin
Cymarin
K- strophanthin B
K- strophanthoside
Cymarose
B-glucose
a-glucose
Strophanthus Group
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The seeds ofStrophanthus gratus containsanother glycoside named Ouabain or (G-strophanthin), which yield on hydrolysisrhamnose and the aglycone ouabagenin.
Ouabagenin differs from K-strophanthidin
in having 2 additional (OH) groups at C-1and C-11 and having a 1ry alcoholic groupat C-10 instead of the aldehydic group.
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BufadienolidesG f di ti t i l d
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Group of cardioactive agentsincludesthe squill glycosides (the scillarins) and theToad poison (Bufotoxin).
Genins of squill glycosides differ from those
of the cardenolides in two importantaspects:They have six membered doubly
unsaturated lactone ring in position C-17.They have at least one double bond in the
steroid nucleus.
O
O
Bufadienolides
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O
OH
Glucose-Glucose-Rhamnose
Scillaridin A
Proscillaridin A
Scillarin A
Glucoscillarin AThe ufadienolides of SquillName of glycosides StructureGlucoscillarin Scillaridin A ---RHG---GScillarin A Scillaridin A ---RHGProscillaridin A Scillaridin A ---RHB
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Physical and ChemicalProperties of Cardiac Glycosides
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Solvent extraction:Alcoholis a good solvent for both the
glycosides and the aglycones. Solvent of
choice for the extraction of all CG fromdrugs.
Petroleum etherand etherare used fordefatting process of drug, they do notdissolve CG.
Physical and ChemicalProperties of Cardiac Glycosides
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Stability:Acid hydrolysis cleavage of the glycosides into
aglycones and sugar residues.
Specific enzyme usually coexist with cardiacglycosides in plants, which may split theprimaryglycosidesinto glycone withless sugar units.
Cardiac glycosides deteriorateduringdrying and storage unless special precautionsare taken.
Physical and ChemicalProperties of Cardiac Glycosides
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Stability:Protected against excessivemoisture
contentand that these drugs should be stored in
sealed containers over dehydratingagents.Heat stabilizescardiac glycosides to destroy
the enzymes at higher temperatures. At highertemperature, the tertiary OH group at C-14may split off as water, leading to formation of aninactive anhydro-form of cardiacglycosides.
Physical and ChemicalProperties of Cardiac Glycosides
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O
R
OH
CH3
Sugar
1
2
3
45
10
67
8
9
11
12
13
14
15
16
17
O O
O
R
CH3
Sugar
1
2
3
45
10
6
7
8
9
11
12
13
14
15
16
17
O O
-H2O
Physical and ChemicalProperties of Cardiac Glycosides
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The gitoxin has in addition to tertiary OH atC-14 another secondary OH at C-16.
Both OH groups split as water by the action
of H2SO4with the formation of twoadditional double bonds.
These with the double bond of the lactone
ring from a conjugated double bond systemthat makes the compound fluorescent in UVlight. (Refer to the previous slide )
Medicinal Importance
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Cardiotonics, CHF, rheumatic heartdisease, atherosclerosis, HTN.
Diuretics (capillary of the kidneys aredialated).
SAR of CardiacGlycosides
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Glycosides The glycone partdisplays a great
influence on the solubility and the rate of
absorption and distribution of theglycosides to the site of action.
Small change in the molecules such as achange of the location of the OH group,modify the cardiac activity or eveneliminate it completely.
SAR of CardiacGlycosides
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Glycosides The saturation and/or cleavage of the
lactone ring, destroys the cardiac activity.
Therefore, the closely related CG, differgreatly in the rate of absorption, duration ofaction and their cumulative effect.
Cardiac drugsOfficial in B.P. and USP
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O c a . . a d US
Digitalis leaf (digitalis tablets)
Digitoxin tablets 200g/tablet
Digoxin injection contain 0.0025% digoxin
Digoxin tablets contain 250g/tablet
Gitalin, lanatoside C, deslanoside,
strophanthus, strophanthin, ouabain andsquill.
Bitter Glycosides
Glycosides with bitter taste also referred to
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Glycosides with bitter taste, also referred toas bitter principle
Complex organic compounds containinglactone ring, soluble in water and very
bitter in taste even in much dilutedsolutions.
Increase the secretions of GIT by reflex
action and are used as stomachic, febrifugeand bitter tonic.
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Iridoid and secoiridoid
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glycosides
Good source includes: Lamiaceae(especially genera Phlomis, Stachys andEremostachys), Gentianaceae, Valerianaceaeand Oleaceae
Iridoid Glycosides
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Devils clawHarpagophytum procumbens Family Name: Pedaliaceae
Constituent/s:Harpagoside, Harpagide, Procumbine
(major)
Use/s:Tx of osteoarthritis, rheumatoid arthritis,
indigestion and low back pain
Iridoid Glycosid
es
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PicrorhizaPicrorhiza kurroaFamily Name: Scrophulariaceae
Constituent/s:Picrosides I-IVKutkoside
Use/s: Tx of indigestion, dyspepsia,constipation, liver dysfunction,bronchial problems and fever.
Ash tree:Fraxinus excelsior
Secoiridoid Glycosides
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Olive tree: Olea europaea; Ligustrumobtusifolium
Family Name: Oleaceae
Constituent:Oleuropein Use/s:HypotensiveAnti-oxidantAnti-viralAnti-microbial
Cysteine Derivatives
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Occur as sulfoxides in the genusAllium
Responsible for the lachrymatory factor of
onions and garlic. S-(trans-propen-1-yl)-cysteine sulfoxide
present in onion
S-allyl derivative: present in garlic
Cysteine Derivatives
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Garlic SN:Allium sativum
FN: Liliaceae
Constituents:
Alliin
Alliin Allinase
allicinDiallydisulfide, diallyltrisulfide gives
the characteristic garlic odor
Miscellaneous Glycosides
STEROIDAL ALKALOIDAL
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GLYCOSIDES: Solanaceae andLiliaceaeWith hemolytic property
- solanin: Present in potato (Solanumtuberosum)
Soladulcin:Bitter-sweet (Solanum
dulcamara)Tomatin: Tomato (Lycopersicon esculentum)
Rubijervin: Veratrumspp.
Miscellaneous Glycosides
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GLYCOSIDAL RESINSConvolvulaceae Family
Examples are: Jalap and Scammony
Upon hydrolysis will yield glucose,rhamnose, fucose, fatty acids and hydroxylderivatives.
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ANTIBIOTIC GLYCOSIDES
Miscellaneous Glycosides
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(Aminoglycosides)Streptomycin Streptidin (aglycone) a nitrogen containing
cyclohexane derivative Streptobiosamine - glycone