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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.


Cleavage

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Enzymatic hydrolysis:


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
http://upload.wikimedia.org/wikipedia/commons/8/8e/Salicylic-acid-skeletal.svg

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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


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


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


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


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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.



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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.


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


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.


Naphthoquinone

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Alkana root(Alkanet/Anchusae radix)

Alkanna tinctoria

FN:Boraginaceae

Constituent & use:

Alkannin - Red

naphthoquinones


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


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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)


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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


Fla onoidal Gl cosides

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Buchu leavesBarosma crenulata

FN: Rutaceae Constituent/s:

Diosmin - flavoneglycoside

Use/s:

Diuretic and diaphoreticaction


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O

OH

O

O

OH

OCH3

A

B Rha-Gl

Upon hydrolysis, diosmin yields _______,________and ________.



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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.


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O

OH

O

O

OR

OH

OHA

BH

Quercetin: R=H

Quercetrin: R= rhamnosyl

Rutin: R=rutinosyl


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O

OH

O

O

OH

OCH3AB

R

Hesperitin R:H

R:rutinosyl Hesperidin


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HO

OH

OH

O

O

O

O

OO

Genisteinshow significantestrogenic activity.

Rotenoidsemployed as insecticide


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


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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


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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


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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


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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


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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


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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.


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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.


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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.


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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


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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.


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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


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(Aminoglycosides)Streptomycin Streptidin (aglycone) a nitrogen containing

cyclohexane derivative Streptobiosamine - glycone

Documents

Glycosides 14-15 (1)