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5/12/2018 Lecture 25 Anthraquinone Glycosides-V - slidepdf.com
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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
5/12/2018 Lecture 25 Anthraquinone Glycosides-V - slidepdf.com
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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
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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 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´
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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
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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 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
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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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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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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?
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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.
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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
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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).
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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.
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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.
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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
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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.
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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.
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COCHINEALCOCHINEAL
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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.
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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.
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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.
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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.
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Cochineal CollectionCochineal Collection
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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.
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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
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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