lecture 24 - anthraquinone glycosides

8/3/2019 Lecture 24 - Anthraquinone Glycosides

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PHARM. D

Chemical Pharmacognosy- I

Lecture 24May 2nd, 2011

ANTHRAQUINONEANTHRAQUINONEGLYCOSIDESGLYCOSIDES--IVIV

M.M. AhsanAhsan KhalidKhalid,, B.PharmB.Pharm, Pharm. D, Pharm. DM.PhilM.Phil Scholar (RIPS/RIU)Scholar (RIPS/RIU)

HIPSHIPS--HUKICHUKIC


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ALOE VERAALOE VERA


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HistoryHistory

Known as the lily of the desert.Known as the lily of the desert. Considered the plant ofConsidered the plant of

immortality by many nativeimmortality by many native

peoples.peoples.

Very long history of medicalVery long history of medical

usageusage

2200 B.C.2200 B.C.-- Mentioned on SumerianMentioned on Sumerian

clay tablets.clay tablets.

1550 B.C.1550 B.C.-- TheThe EbersEbers Papyrus statesPapyrus states

12 recipes for mixing Aloe with other12 recipes for mixing Aloe with other

agents to treat human disorders.agents to treat human disorders.

Usually the whole leaf was groundUsually the whole leaf was ground

and mixed with another medicinaland mixed with another medicinal

agent.agent.

Used by Cleopatra andUsed by Cleopatra and NerfertitiNerfertiti..


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History ContinuedHistory Continued

400 B.C.400 B.C.-- Extensively traded in the Near EastExtensively traded in the Near East

and Asia.and Asia.

333 B.C.333 B.C.-- The Island of Socotra was captured by AlexanderThe Island of Socotra was captured by Alexander

the Great because of its Aloe supplies.the Great because of its Aloe supplies. 68 A.D.68 A.D.-- DioscoridesDioscorides wrote a detailed description of Aloewrote a detailed description of Aloe

veravera and all of its uses.and all of its uses.

200 A.D.200 A.D.--AloeAloe veravera was an important part of Romanwas an important part of Roman

medicine and became extremely popular in Europe inmedicine and became extremely popular in Europe in

the centuries to come.the centuries to come. 1500 A.D.1500 A.D.-- Introduced to the New World by the ConquistadorsIntroduced to the New World by the Conquistadors


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Modern HistoryModern History

First modern medical paper published inFirst modern medical paper published in

1934.1934.

Described how the whole leaf wasDescribed how the whole leaf was

used to treat radiation dermatitis.used to treat radiation dermatitis. Many papers published in the 20Many papers published in the 20thth centurycentury

describing a wide range of medicinaldescribing a wide range of medicinal

properties.properties.

Reports have mainly focused on theReports have mainly focused on the

antidiabeticantidiabetic, anticancer, and antimicrobial, anticancer, and antimicrobialproperties of the whole leaf, gel, or juiceproperties of the whole leaf, gel, or juice

of the plant.of the plant.

Many species of Aloe have been studied.Many species of Aloe have been studied.


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Member of the lily family.

240 species ofAloe.

Aloe Vera, Aloe Barbadensis.

Succulent, perennial, evergreen.

Very hardy.

Native to Africa, but is now widespread.

It is a bitter herb with a wide range of

medicinal properties.

It contains over 75 compounds, many of

which are biologically active.

General Information


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AloeAloe -- LiliaceaeLiliaceae Definition:Definition: Aloes are theAloes are the

solid residue obtained bysolid residue obtained byevaporating the liquidevaporating the liquidwhich drains from thewhich drains from thetransversely cut leaves oftransversely cut leaves ofvariousvariousAloeAloe species.species.

The juice is usuallyThe juice is usuallyconcentrated by boilingconcentrated by boilingand solidifies on cooling.and solidifies on cooling.

Official varieties are theOfficial varieties are theCape Aloes from SA andCape Aloes from SA andKenya (Kenya (Aloe feroxAloe ferox), and), andthe Curacao Aloes fromthe Curacao Aloes fromWest IndiesWest Indies ((AloeAloebarbadensisbarbadensis

).).


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Preparation of Cape AloesPreparation of Cape Aloes

Cape Aloes are prepared from the wild plantsCape Aloes are prepared from the wild plantsof Aloe feroxof Aloe ferox

..

Leaves are cut transversely near the base.Leaves are cut transversely near the base.

200 leaves arranged around a shallow hole in the ground200 leaves arranged around a shallow hole in the ground

(lined with canvas or goatskin).(lined with canvas or goatskin).

Cut ends overlap & drain into the canvas.Cut ends overlap & drain into the canvas.

After 6hrs all the juice is collected.After 6hrs all the juice is collected.

Transferred to a drum.Transferred to a drum.

Boiled for 4hrs on an open fire.Boiled for 4hrs on an open fire.


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Preparation of Cape AloesPreparation of Cape Aloes


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Cape AloesCape Aloes -- CharacteristicsCharacteristics

Dark brown or GreenDark brown or Green--

brownbrown

Glassy massesGlassy masses

Thin fragments haveThin fragments have

a deep olive coloura deep olive colour

SemiSemi--transparent.transparent.


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Cape AloesCape Aloes -- CharacteristicsCharacteristics

Powder: greenPowder: green--yellowyellow

Characteristic sour odourCharacteristic sour odour

(rhubarb/apple(rhubarb/apple--tarttart

odour).odour).

Taste: nauseous andTaste: nauseous and

bitter.bitter.

Microscopy: powder inMicroscopy: powder in

lactophenollactophenol amorphous.amorphous.


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Characteristics of Curacao AloesCharacteristics of Curacao Aloes Colour: yellowColour: yellow--brownbrown

chocolate brown.chocolate brown. Poor qualitiesPoor qualities

(overheated) black(overheated) blackcolour.colour.

OpaqueOpaque

Breaks with a waxyBreaks with a waxyfacturefacture

SemiSemi--transparenttransparent

More opaque on keeping.More opaque on keeping.

Nauseous and bitterNauseous and bittertaste.taste.

CharacteristicCharacteristic iodoformiodoformodour.odour.

Microscopy:Microscopy: lactophenollactophenol

acicular crystalsacicular crystals


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AloesAloes -- ConstituentsConstituents

CC--glycosidesglycosides

ResinsResins

GlycosidesGlycosides AloinAloin

BarbaloinBarbaloin

IsobarbaloinIsobarbaloin

AloeAloe--emodinemodin

Cape Aloes:Cape Aloes: Also ContainAlso ContainAloinoside AAloinoside A &&Aloinoside BAloinoside B

(O(O--glycosides ofglycosides ofbarbaloin)barbaloin)


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AloeAloe -- ConstituentsConstituents


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Aloe Constituents & ChemicalAloe Constituents & Chemical

Tests:Tests:Unlike CUnlike C--glycosides, Oglycosides, O--glycosides ofglycosides of

AloeAloe are not hydrolysed by heatingare not hydrolysed by heatingwith dilute acids or alkali.with dilute acids or alkali.

Can be decomposed with ferricCan be decomposed with ferric

chloride & dilute HLCchloride & dilute HLC

ModifiedModified BorntragersBorntragers TestTestoxidative hydrolysis.oxidative hydrolysis.

AnthraquinonesAnthraquinones give agive a redred colourcolour

when shaken with dilute ammonia.when shaken with dilute ammonia.

All Aloes give a strongAll Aloes give a strong greengreen

fluorescencefluorescence with boraxwith borax

(characteristic of(characteristic of anthranolsanthranols)) --

General test for aloes.General test for aloes.


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Aloe and Irritable Bowel Syndrome (IBS)Aloe and Irritable Bowel Syndrome (IBS)

Normal: digestive tractNormal: digestive tract

absorbs nutrients into bloodabsorbs nutrients into blood

bacteria helpsbacteria helps

breakdown foodbreakdown food

IBS: unabsorbed food coatsIBS: unabsorbed food coatsthe bowel preventing normalthe bowel preventing normal

absorptionabsorption

Symptoms:ExhaustionSymptoms:Exhaustion,,

constipation, diarrhea, andconstipation, diarrhea, and

indigestionindigestion Colonic Irrigation: loosedColonic Irrigation: loosed

and wash out residuesand wash out residues


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Aloe and Rheumatoid ArthritisAloe and Rheumatoid Arthritis

Two main types of arthritisTwo main types of arthritis

Osteoarthritis: wear andOsteoarthritis: wear andtear of lifetear of life

Rheumatoid:Rheumatoid:

autoimmune diseaseautoimmune disease Symptoms: stiff, red,Symptoms: stiff, red,

swollen jointsswollen joints

Traditional treatment: antiTraditional treatment: anti--inflammatory drugs withinflammatory drugs withsteroidssteroids

Aloe helps repair damageAloe helps repair damage Mode of Action: stimulateMode of Action: stimulate

the Cytokinesthe Cytokines

Varying resultsVarying results


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Aloe and CosmeticsAloe and Cosmetics

Added because of knownAdded because of knownrejuvenating actionrejuvenating action

Mode of Action:Mode of Action:

PolysaccachridesPolysaccachrides act asact as

moisturizersmoisturizers Stimulates the fibroblasts toStimulates the fibroblasts to

replicate fasterreplicate faster

Smoothes skin because sticksSmoothes skin because sticksepidermal cells together whichepidermal cells together whichnormally flakenormally flake

Interferes with melanin depositInterferes with melanin depositproduction which lead to liverproduction which lead to liverspotsspots


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Aloe and DiabetesAloe and Diabetes

Characterized byCharacterized by hyperglycaemiahyperglycaemia and alterations ofand alterations of

glucose and lipid metabolismglucose and lipid metabolism

Lead to cell damage and elevation of reactiveLead to cell damage and elevation of reactive

oxygen speciesoxygen species Must control blood glucose and lipid levelsMust control blood glucose and lipid levels

Aloe shown to reduce blood glucose in diabetic ratsAloe shown to reduce blood glucose in diabetic rats


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Control (mg/dL)

Control + 300mg/kg Aloe vera +600microgram/kg Glibenclamide

Chlosterol 92.6 5.7 228.3 15.1 98.3 8.5 106.2 7.0

Triglycerides 735 5.2 229.3 16.1 79.2 5.2 83.4 5.8

Phospholipids 80.5 5.7 163.8 11.1 85.7 5.8 88.8 6.7

Free fatty acids 58.3 3.6 145.2 10.5 64.7 4.1 66.1 4.6LDLs 45.1 2.9 139.2 10.3 48.5 3.1 53.4 3.4

HDLs 26.5 1.7 21.3 1.6 23.4 1.5 22.03 1.42

Diabetic (mg/dL)


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Decrease in blood glucoseDecrease in blood glucose

due to stimulation of insulindue to stimulation of insulin

secretionsecretion Decrease in cholesterol,Decrease in cholesterol,

triglycerides, phospholipids,triglycerides, phospholipids,

and free fatty acids fromand free fatty acids from

increased clearance andincreased clearance and

decreased transportersdecreased transporters


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AntiAnti--Microbial/Microbial/--BacterialBacterial

50% gel leaf solution, complete inhibition of50% gel leaf solution, complete inhibition ofStaphylococcusStaphylococcus

aureusaureus

Due toDue to phenolicsphenolics

Efficacy of gel or leaf?Efficacy of gel or leaf?

S.S. aureusaureus inhibited by bothinhibited by both

Other bacteria inhibited byOther bacteria inhibited by

just leaf or geljust leaf or gel


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Aloe, Antimicrobials, and WoundsAloe, Antimicrobials, and Wounds

When aloe is combinedWhen aloe is combined

with other antiwith other anti--microbials,microbials,

a wound heals faster thana wound heals faster thanwith the antiwith the anti--microbialmicrobial

alone.alone.

Possibly due to itsPossibly due to its

moisturizing capability asmoisturizing capability as

well.well.


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Immune Booster?Immune Booster?

Asian practice of ingestingAsian practice of ingesting

herbs to support the immuneherbs to support the immune

systemsystem May have a direct inhibitoryMay have a direct inhibitory

effect on microbeseffect on microbes

Also, selectively modulatesAlso, selectively modulates

cells of the immune systemcells of the immune system


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Alveolar OsteitisAlveolar Osteitis

Dry Socket (Wisdom teeth extraction)Dry Socket (Wisdom teeth extraction)

AcemannanAcemannan HydrogelHydrogel (from clear inner gel of aloe(from clear inner gel of aloe veravera))

Normal treatment 7.6% develop AONormal treatment 7.6% develop AO

WithWith AcemannanAcemannan 1.1% develop AO1.1% develop AO

Normal Dry socket, clot does not

form properly


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Burn TreatmentBurn Treatment

Shows increased healing effects on 2Shows increased healing effects on 2ndnd degree burnsdegree burns

AntiAnti--inflammation and wound healing promotioninflammation and wound healing promotion

Vessels return to normal size quicker than withVessels return to normal size quicker than with

untreated burnsuntreated burns


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CochinealCochineal -- CharacteristicsCharacteristics

Oval in shapeOval in shape

Half cm in lengthHalf cm in length

ExaminedExamined

microscopically aftermicroscopically after

removing theremoving the

colouring mattercolouring matter(ammonia solution).(ammonia solution).

Each insect contains 60Each insect contains 60

450 eggs and450 eggs and

larvae.larvae.


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CochinealCochineal -- ConstituentsConstituents

CC--glycosideglycoside anthraquinone derivativeanthraquinone derivative brightbrightpurple, waterpurple, water--solublesoluble colouring mattercolouring matter

Carminic acidCarminic acid

FatFat WaxWax

Adulteration:Adulteration: occurs by increasing the weight ofoccurs by increasing the weight ofthe insects by dressing it with inorganic matterthe insects by dressing it with inorganic matterin a colour which blends in with that of thein a colour which blends in with that of theinsect.insect.

Detected when insects are placed in waterDetected when insects are placed in water


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Last Word on AnthraquinonesLast Word on Anthraquinones

Anthraquinones take aboutAnthraquinones take about10hours to produce an effect10hours to produce an effect(take overnight)(take overnight)

Should not be used for moreShould not be used for more

than 10 days.than 10 days.

Should not be used byShould not be used bychildren, pregnant andchildren, pregnant andlactating women.lactating women.

Cause griping pain.Cause griping pain.

Are habitAre habit--forming.forming.

Anthraquinones = phenolicAnthraquinones = phenolicglycosides, used as anglycosides, used as an

irritating laxativeirritating laxative

lecture 24 - anthraquinone glycosides

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