lecture 25 anthraquinone glycosides-v

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PHARM. D

Chemical Pharmacognosy- I

Lecture 25May 4th, 2011

ANTHRAQUINONEANTHRAQUINONEGLYCOSIDESGLYCOSIDES--VV

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

HIPSHIPS--HUKICHUKIC



10 Main Component Groups of Aloe10 Main Component Groups of Aloe

LigninsLignins Inert except when inInert except when in

topical treatmentstopical treatments

SaponinsSaponins

3% of Aloe Vera gel3% of Aloe Vera gel Fatty AcidsFatty Acids

Cholesterol,Cholesterol,CampesterolCampesterol,, SisosterolSisosterol,,andand LupeolLupeol

SalicyclicSalicyclic acidacid AspirinAspirin--likelike

Amino AcidsAmino Acids 20 amino acids20 amino acids

VitaminsVitamins Vitamin D, A, C, E and B12Vitamin D, A, C, E and B12

EnzymesEnzymes Lipases, proteases,Lipases, proteases,

kinaseskinases MineralsMinerals

Ca, Na, K, Mg,Ca, Na, K, Mg, MnMn, Cu, Zn,, Cu, Zn,Cr, and SeCr, and Se

SugarsSugars Mono and polyMono and poly

saccharidessaccharides,, glucogluco--mannansmannans

AnthraquinonesAnthraquinones Most important:Most important: AloinAloin, and, and

EmodinEmodin



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



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



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 faster replicate faster

Smoothes skin because sticksSmoothes skin because sticksepidermal cells together whichepidermal cells together which

normally flakenormally flake Interferes with melanin depositInterferes with melanin deposit

production which lead to ³liver production which lead to ³liver spots´spots´



Aloe and DiabetesAloe and Diabetes

Characterized byCharacterized by hyperglycaemiahyperglycaemia and alterations of and 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



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



AntiAnti--Microbial/Microbial/--BacterialBacterial

50% gel leaf solution, complete inhibition of 50% gel leaf solution, complete inhibition of StaphylococcusStaphylococcus

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 gel just leaf or gel



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.



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



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



Aloe and Cancer Aloe and Cancer

AloeAloe--emodinemodin induces apoptosisinduces apoptosis

in T24 human bladder cancer in T24 human bladder cancer

cellscells

Inhibits cell viability, inducesInhibits cell viability, induces

G2/M arrestG2/M arrest

MechanismMechanism-- p53, p21,p53, p21, caspasecaspase

activationactivation

Treat Radiation Symptoms?Treat Radiation Symptoms?



Investigated anticancer effect of AE (1,8-dihydroy-3-[hydroxymethyl]-anthraquione) in

the T24 human bladder cancer cell line by studying apoptosis regulation.

AE, is purified from aloe vera leaves, has been reported to have antitumor activity.

Levels of cyclins, cyclin-dependent kinase 1 and other enzyme were examined

Results: AE inhibited cell viability, and induced Growth2/Mitosis arrest and

apoptosis in T24 cells.

AE increased the levels of Wee1 and cdc25c

AE may have led to inhibition of the levels of cyclin-dependent kinase 1 and cyclin 131,

which cause G2/M arrest.

AE induced p53 expression and was accompanied by the induction of p21 and

caspase-3 activation, which was associated with apoptosis.

Conclusions: AE induced apoptosis in T24 cells is mediated through the activation of

p53, p2l, Fas/APO-1, Bax and caspase-3.

No evidence that it can prevent radiation induced skin inflammation in Cancer patients.



Neuroectodermal Cancer Neuroectodermal Cancer

InhibitsInhibits neuroectodermalneuroectodermal tumors in mice.tumors in mice.

Few toxic effects, does not inhibit normal fibroblasts.Few toxic effects, does not inhibit normal fibroblasts.

Induces apoptosis and is specific to a tumor energyInduces apoptosis and is specific to a tumor energy--

dependent pathway of drug incorporationdependent pathway of drug incorporation



Cancer UCancer U--373373 GliomaGlioma CellsCells

Aloe-emodin from Aloe vera leaves has been reported to have antitumor activity.

How does aloe-emodin regulate the cell cycle, cell proliferation and protein

kinase C (PKC) during glioma growth and development?

Aloe-emodin delayed the number of cells entering and exiting DN A synthesis

(S) phase in both SVG and U-373MG cells indicating that Aloe-emodin may

inhibit S phase progression. The aloe-emodin-induced decreased proliferation

was sustained at 48-96 h.

Aloe-emodin suppressed PKC activity and reduced the protein content of most

of the PKC isozymes.

Cancer growth inhibition by aloe-emodin was due to apoptosis (i.e.,

programmed cell death).



Gastric and Colorectal CancersGastric and Colorectal Cancers

Anticancer effects of aloe on sarcoma 180 in ICR mouse or human cancer

cells were determined.

Determine effect of aloe on life span prolongation, followed by oral

administration of Aloe vera (10 mg/kg/day, 50 mg/kg/day) or Aloe arborescens(10 mg/kg/day, 100 mg/kg/day) once a day for 14 days.

The administration of Aloe vera or Aloe arborescens did not suppress tumor

growth.

However the life span of ICR mouse was prolonged to 19% (P lt 0.05), 22% (P

lt 0.05), and 32% (P lt 0.05) by administration of Aloe vera 10 mg/kg/day, Aloe

vera 50 mg/kg/day, and Aloe arborescens 100 mg/kg/day, respectively.

Not necessarily an anti-cancer effect, but definitely an anti-growth effect.



ProductsProducts

Gel and latex.Gel and latex.

GelGel-- leaf pulp or mucilageleaf pulp or mucilage

obtained from theobtained from the parenchymalparenchymal

tissue.tissue.

LatexLatex-- bitter, yellow substancebitter, yellow substanceobtained fromobtained from pericyclicpericyclic tubulestubules

just beneath the outer skin of the just beneath the outer skin of the

leaves. (otherwise called µAloeleaves. (otherwise called µAloe

juice¶) juice¶)

Using a freshly cut leaf isUsing a freshly cut leaf is

thought to be the most effectivethought to be the most effective

treatment.treatment.



SummarySummary

1.1. Dental Health and HygieneDental Health and Hygiene

2.2. Provides Rapid SoothingProvides Rapid Soothing

3.3. Aids in Healthy DigestionAids in Healthy Digestion

4.4. Immune Support and FunctionImmune Support and Function5.5. Regulates Weight and Energy LevelsRegulates Weight and Energy Levels

6.6. Collagen andCollagen and ElastinElastin Repair Repair

7.7. Daily Dose of MineralsDaily Dose of Minerals

8.8. Daily Dose of VitaminsDaily Dose of Vitamins

9.9. AntiAnti--inflammatory Propertiesinflammatory Properties

10.10. Essential Amino AcidsEssential Amino Acids



Aloe Aloe -- UsesUses

PurgativePurgative

Seldom prescribed aloneSeldom prescribed alone

± ± activity is increasedactivity is increasedwhen administered withwhen administered with

small quantities of soapsmall quantities of soap

or alkaline salts;or alkaline salts;

Carminatives moderateCarminatives moderate

griping tendency.griping tendency.

Ingredient inIngredient in Friar¶sFriar¶s

Balsam.Balsam.



Aloe Aloe ± ± Additional Notes Additional Notes

Medicinal Uses:Medicinal Uses: Anti Anti--bacterial, antibacterial, anti--fungal,fungal,

chologoguechologogue,,emmenogogueemmenogogue,,antiinflammatoryantiinflammatory (juice),(juice),antianti--inflammatory ,inflammatory ,demulcent, immunedemulcent, immune--stimulating (gel).stimulating (gel).

Radiation burnsRadiation burns (internal and(internal and

external use)external use)

ContraContra--indicationsindicationsPregnancy & lactationPregnancy & lactation

(internal uses)(internal uses)

EtymologyEtymology Name derives from ArabicName derives from Arabic

alualu,, meaning shiny or bitter meaning shiny or bitter in reference to the gel.in reference to the gel.

Other usesOther uses KhoiKhoi--San hunters rub gelSan hunters rub gel

on their bodies to reduceon their bodies to reducesweating and mask their sweating and mask their scent.scent.

Used to break nailUsed to break nail--bitingbitinghabit.habit.



COCHINEALCOCHINEAL



CochinealCochineal

Definition:Definition: CochinealCochineal

is the dried femaleis the dried female

insect,insect, DactylopiusDactylopius

coccuscoccus, containing, containingeggs and larvae.eggs and larvae.

Insects areInsects are

indigenous to Centralindigenous to Central

America, commercial America, commercialsupplies are derivedsupplies are derived

from Peru.from Peru.



CochinealCochineal Eggs are protected duringEggs are protected during

the rainy season arethe rainy season are

µsown¶ on cactiµsown¶ on cacti ± ± onon

which it is intended towhich it is intended tobreed.breed.

Both male and femalesBoth male and females

arise. After a time,arise. After a time,

fecundation occurs.fecundation occurs.

Females attachFemales attach

themselves to the cactithemselves to the cacti

and the males die out.and the males die out.

Females swell to x2 their Females swell to x2 their

original size due tooriginal size due to

developing larvae &developing larvae &

develop red colouringdevelop red colouringmatter.matter.



CochinealCochineal

Larvae mature after 14days and escape fromLarvae mature after 14days and escape fromthe now dead body of the parent.the now dead body of the parent.

Only a small portion develop into males.Only a small portion develop into males.

For next 2 weeks, males fly and young femalesFor next 2 weeks, males fly and young females

crawl on the plant.crawl on the plant.

Life cycle = 6 weeks.Life cycle = 6 weeks.

33--5 generations may be produced in 1 season.5 generations may be produced in 1 season.



CochinealCochineal -- CollectionCollection Insects are brushed from plants with smallInsects are brushed from plants with small

brooms and killed (some left to provide for brooms and killed (some left to provide for subsequent crops).subsequent crops).

First crop killed contains the most colouringFirst crop killed contains the most colouringmatter.matter.

Insects are killed by plunging them in boilingInsects are killed by plunging them in boilingwater, stove heat or exposure to fumes bywater, stove heat or exposure to fumes byburning sulphur or charcoal.burning sulphur or charcoal.

If heat is usedIf heat is used ± ± insects change to purpleinsects change to purple ± ± blackblack ± ± called µblack grain¶.called µblack grain¶.

Fume killedFume killed ± ± turn purpleturn purple--grey called µsilver grey called µsilver grain¶.grain¶.

Small immature insects and larvae which can beSmall immature insects and larvae which can beseparated by sieves are sold as µgranilla¶ or separated by sieves are sold as µgranilla¶ or

siftings.siftings.



Cochineal CollectionCochineal Collection



CochinealCochineal -- CharacteristicsCharacteristics

Oval in shapeOval in shape

Half cm in lengthHalf cm in length

ExaminedExamined

microscopically after microscopically after

removing theremoving the

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

Each insect contains 60Each insect contains 60

± ± 450 eggs and450 eggs and

larvae.larvae.



CochinealCochineal -- ConstituentsConstituents

CC--glycosideglycoside ± ± anthraquinone derivativeanthraquinone derivative brightbrightpurple, water purple, water--solublesoluble colouring matter colouring matter

Carminic acidCarminic acid

FatFat WaxWax

Adulteration: Adulteration: occurs by increasing the weight of occurs by increasing the weight of the insects by µdressing¶ it with inorganic matter the insects by µdressing¶ it with inorganic matter in 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 water Detected when insects are placed in water



Last Word on AnthraquinonesLast Word on Anthraquinones

Anthraquinones Anthraquinones take abouttake 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 habit Are habit--forming.forming.

Anthraquinones Anthraquinones == phenolicphenolicglycosides, used as anglycosides, used as an

irritating laxativeirritating laxative

lecture 25 anthraquinone glycosides-v

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