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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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Aloe and DiabetesAloe and Diabetes
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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Aloe and DiabetesAloe and Diabetes
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