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Lecture 21 - 23 Anthraquinone Glycosides

Lecture 21 - 23 Anthraquinone Glycosides

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PHARM.

D Chemical Pharmacognosy- I Lecture 21-23 April 25th, 2011

ANTHRAQUINONE GLYCOSIDES
M. Ahsan Khalid, B.Pharm, Pharm. D B.Pharm,
M.Phil Scholar (RIPS/RIU) HIPSHIPS-HUKIC

Anthraquinone Structure

Anthracene (Anthraquinone) Glycosides 

Anthracene glycosides are oxygenated derivatives of pharmacological importance that are used as laxatives or cathartics, anti-inflammatory, antibacterial, antifungal and also antias natural dyes. dyes.
O
tautomerization

OH
Oxidation Reduction

O

H

H Anthranol

H

OH

Anthrone

Oxanthrone

Reduction

O
8 9 10 5 4 1

Oxidation

O Anthraquinone

Anthracene glycosides 
 

Purgative principles Found in several plant drugs Occur in glycoside form 


and less commonly in aglycone form free aglycones have to be removed in assay because inactive 



2-3%w/w (both forms) based on anthracene molecule

Introduction to Anthraquinones 

Historically: Rhubarb, Senna, Aloes and Cascara were all used as purgative drugs. Monocotyledons: Only Liliaceae.  

Most commonly C-glycoside: barbaloin. C- 

Dicotyledons: Rubiaceae, Leguminosae, Polygonaceae, Rhamnaceae, Ericaceae, Euphorbiaceae, Lythraceae, Saxifragaceae, Scrophulariaceae and Verbenacacea. Also in certain fungi and lichen.

Anthranonls and Anthrones 
 

Reduced anthraquinone derivatives Occur either freely (aglycones) or as glycosides. Isomers Anthrone: Parent structure (pale yellow, nonnonsoluble in alkali, non-fluorescent) nonAnthronol: brown-yellow, soluble in alkali, brownstrongly fluorescent   

Anthronol derivatives (e.g. in Aloe ± have similar properties ± fluorescence used for identification)

Oxanthrones 


Found in Cascara bark Intermediate products (between anthraquinones and anthranols) When oxidised form anthraquinones  

Accomplished via Modified Borntrager¶s Test (oxanthrones oxidised using hydrogen peroxide)

Dianthrones 
  

Derived from 2 anthrone molecules 2 molecules may/not be identical Form easily due to mild oxidation of anthrones Form important aglycones 
 

Cassia Rheum Rhamnus 

3 oxygenated or substituted forms of the anthracene molecule exist

Anthraquinone (most common)

Anthrone (reduced form occurring in plant)

Dianthrone (reduced dimer) 

all flat, planar structures 

flat molecule can get into gut mucosa and irritate eventually causing peristalsis 

4 aglycone structures
all existing in any of the 3 forms  phenolic group is the irritant principle 

Chrysophanol Rhein anthraquinone

Aloe-emodin

Emodin

The activity decreases as oxidation level increase. 

Forms of Anthracene derivatives in Plants: 

Aglycones:

OH

O

OH

OH

O

OH

OH

O

OH

OH

O

OH

HO

O

CH3

O

CH 2OH

O

CH3

O

COOH

Emodin

Aloe-emodin

Chrysophanol

Rhein 

biologically active part is the glycoside 
tend

to have simple sugars attached

1- monoglucoside at C8 
O-linked

2- diglucoside at C1 andC8

3- µC¶- glycosides µC¶

have a direct C linkage ± aloins

* resistant to hydrolysis (need to use ferric chloride) 



all types combined to give complex mixture in the plant assays different since each compound has different purgative potency 

Dimeric Anthracene derivatives: 

They are derived from two anthracene unites connected by covalent C-C bond through C-10. C- 

HomoHomo-Dianthrones:
The two anthrone moieties are similar. e.g. Sennidins A&B and their similar. corresponding glycosides Sennosides A&B. They are all formed of A&B. two Rhein monomers. The A group are (l)-form while the B group are monomers. (l)meso compounds with zero optical rotation. rotation.
OR O OH

HOOC

H

H

COOH

OH
R= H R= Glc R= H R= Glc = = = =

O

OR
Sennidin A Sennoside A Sennidin B Sennoside B 

Hetero-Dianthrones: Hetero-Dianthrones:
The two anthrone moieties are different. e.g. Sennidins C&D and their different. corresponding glycosides Sennosides C&D. They are all formed of one C&D. Rhein and one Aloe-emodin monomers. The C group are (l)-form while Aloemonomers. (l)the D group are meso compounds with zero optical rotation. rotation.

OR

O

OH

HOOC

H

H

CH2OH

OH
R= H R= Glc R= H R= Glc = = = =

O

OR
Sennidin C Sennoside C Sennidin D Sennoside D 

Glycosides: 

O-glycosides:
e.g. Cascarosides A & B. They are both O- and C-glycosides. Each one OCcontain two sugar unites. OH Glc O O

R1
R= Glc, R1= H R= H, R1= Glc

R

CH2OH
Cascaroside A Cascaroside B 

C-glycosides:
OH O OH

e.g. Barbaloin it is formed from the removal of one sugar from Cascarosides. Cascarosides.

CH2OH H Glc

Mechanism of action 

Molecules have to possess certain features for activity:
1- Glycosides 2- Carbonyl keto function on centre ring 3- 1,-8- positions have to have ±OH 1,- 

Potency: 

anthrone > anthraquinone> dianthrone anthraquinone> 

Aglycones not therapeutically active in animals ± lipid soluble ± absorbed in stomach and never reach colon to produce a local effect

Mechanism of Action: 

The glycosides are absorbed from the small intestine and re-excreted in the large reintestine where they increase the motility so produce laxation. laxation. Aglycones produce griping effect so it is recommended to prescripe antispasmodic with them.  



Highly active phenolic group irritant to mucosa Glycosides very water soluble ± reach large intestine where they are hydrolysed by E.coli enzymes ± become lipid soluble ± absorbed into circulation ± on way through gut wall disturb Aubach nerve plexus causing smooth muscle to contract ± peristalsis 5-8 hours to act 
   

take night before in low doses ± drug metabolised by liver and recirculated via bile to give more effect people esp elderly can become reliant on them needing higher dose to produce an effect carcinogenic ± Melanosis coli

StructureStructure-Activity Relationship: 
 

Glycosylation is essential for activity. Hydroxylation at C-1 and C-8 is essential for activity. CCOxidation level at C-9 and C-10 is important: CC  

Highest level of oxidation (anthraquinones) have the lowest activity. Oxanthrones are less active than anthrones. Complete reduction of C-9 and C-10 eliminates the activity. CC- 

Substitution at C-3 have great impact on activity: CCH2OH > CH3 > COOH

Extraction 
      

Most quite polar 

due to phenols and sugars

Water/alcohol or mixtures of them used Dried plant material percolation in industrial columns with dilute alcohol Tincture produced Partitioned with chloroform/ether to clean up (remove green pigment, fats, lipids) Clean yellow tincture subjected to column chromatography Gradual elution of individual glycosides Crystallised for purity 

Identification: 
   

Easy ± coloured orange-yellow orangeChemical test: Borntrager¶s test in alkali (KOH, NH3) phenolic groups -> phenate complex (bright red) TLC using silica gel ± plates do not have to be sprayed since yellow but can confirm with KOH (red spot) Mass spectrometry

Assay 

Isolating each active component too expensive 


powdered plant material (tablets or capsules) or aqueous (fluid) extracts used 

Difficult ± each component in mixture has different potency Safest assay is:  

[i] biological assay of dry material
wet faeces method ± cage full of mice or rats on a grid with collecting tray below ± feed eg senna in food ± collect faeces and weigh ± calculate ED50 ± oral dose in food correlating to faeces produced

[ii] chemical assay 

spectroscopy ± quick and cheap, more accurate but gives same emphasis to each compound 

To remove aglycones 

make an extract, shake with ether 

discard ether phase containing free aglycones  then acid hydrolyse aqueous phase containing glycosides  with ferric chloride for direct C- bonds C and with dilute HCl 
 

extract in CHCl3 


gives aglycones from glycosides then measure on spectrophotometer peak 515nm

colour with magnesium acetate OR do colourimetric assay ± red in alkali - 250nm

Chemical test:
Borntrager¶s and Modified Borntrager¶s test: 

For Aglycones: 


Extract plant material with organic solvent. Shake with NH4OH OR KOH. Boil plant material with dil. HCl for 10 min, filter and shake with organic solvent (Ether or Benzene). Separate the organic solvent. Shake with NH4OH OR KOH. Boil plant material with dil. HCl/FeCl3, filter and shake with organic solvent (Ether or Benzene). Separate the organic solvent. Shake with NH4OH OR KOH. 

For O-Glycosides: O   

For C-Glycosides: C   

Positive result indicated by Rose Red colour in the aqueous alkaline layer.

Some Drugs containing Anthracene derivatives: 

Senna: Senna: 


Leaves and pods contain Sennosides A-D. The C-C bond protect the anthrone from oxidation. C- 

Cascara bark: bark: 
  

Contain Cascarosides A- D. Barbaloin present as a secondary glycoside in Cascara. Cascara. They are O- and C-glycosides. OCThe C-linked glucose at C-10 protect anthrones from CCoxidation. 

Aloes: 
 

The major glycoside in Aloes is the C-glycoside Barbaloin. CBarbaloin. Barbaloin is primary glycoside in Aloes. The C-linked glucose at C-10 protect anthrones from CCoxidation. 

Rhubarb: Rhubarb: 
It

is purgative only in large doses.  It contains high amount of tannins that have astringent effect. 

Frangula bark: bark: 
Contain

anthraquinone derivatives the most oxidized and least active.

SENNA

Senna - Leguminosae 

Definition: Consists of the dried leaflets of Cassia senna (Alexandrian senna), or Cassia angustifolia (Tinnevelly senna).

Cassia spp - Senna 
  

Indigenous to Africa (tropical regions) Used since 9th ± 10th century Introduced into medicine by Arab physicians (used both the leaves and pods) Exported by Alexandria ± name of the Sudanese drug. 

   

Collected in September Whole branches bearing leaves are dried in the sun. Pods and large stalks are separated with sieves. Leaves are graded (whole leaves, whole leaves and half-leave halfmix, siftings). Whole leaves ± sold to public

Senna - Collection 

Rest ± used for galenicals.

Senna - Constituents 

2 active glycosides: glycosides: 

Sennoside A Sennoside B

Both hydrolyse: 2 molecules glucose + aglycones: aglycones: Sennidin A and Sennidin B. B.

Sennoside C & Sennoside D  Rhein  Aloe-emodin Aloe Palmidin A (Rhubarb) 

Chemical constituents:
(i) 1 and 1,8 µO¶ glucosides
= 1st series glycosides aglycones: rhein, aglycones: rhein, aloe emodin

(ii) dimeric dianthrones
= 2nd series reduced products

dimer can be split into two parts with FeCl3 hydrolysis and monomer aglycones assayed for

Senna - Constituents 

Kaempferol (yellow flavanol) + glucoside (kaempferin) kaempferin) Mucilage Calcium oxalates Resin 

 

Comparison of Alexandrian and Tinnevelly Senna 

Macroscopical 
    

Macroscopical 
   

Seldom larger than 4 cm in length GreyGrey-green Asymmetric at base Broken and curled at edges Few press markings

Seldom exceeds 5cm in length YellowYellow-green Less asymmetric at base Seldom broken and normally flat Often shows impressions (mid vein)

Comparison between Alexandrian and Tinnevelly Senna 

Microscopical  

Microscopical  

Hairs ± numerous (approximately 3 epidermal cells apart) Most stomata have 2 subsidiary cells 

Hairs less numerous (approximately 6 epidermal cells apart) Stomata have 2-3 2subsidiary cells with the respective ratio 7:3

Comparison between Alexandrian and Tinnevelly Senna 

Chemical Tests  

Chemical Tests 

Ether extract of hydrolysed acid solution of herb with methanolic magnesioum acetate solution gives 


Same Test

Pink colour in daylight Pale green-orange greencolour in filtered UV light 



Orange colour in daylight YellowYellow-green colour in filtered UV light

Comparison between Alexandrian and Tinnevelly Senna 

TLC  

TLC 

Hydroxymusizin glycoside present

Tinnevellin glycoside present

Senna ± Allied Drugs & Substitutes 

Bombay, Mecca and Arabian Sennas (found in Cassia angustifolia from Arabia). Dog senna ± Cassia obovata Cassia auriculata ± Indian Senna Cassia podocarpa 

Substitutes or Adulterants 

Argel leaves ± Solenostemma argel Coriario myrtifolia    

Senna Fruit 

Definition: Senna pods are the dried, ripe fruits of Cassia senna and Cassia angustifolia, angustifolia, which are commercially known as Alexandrian and Tinnevelly senna pods respectively. Both have separate monographs

Senna Fruit - Collection 

Pods are collected with the leaves and dried in a similar fashion. After separation of the leaves, the pods are handhand-picked into various qualities, the finer being sold (commercially), while the finer pieces are used to make galenicals.

Senna Fruit - Constituents 

Active constituents ± found in the pericarp Similar to those actives of the leaves 
 

Sennoside A Sennidin

Senna - Uses
Laxatives (habitual constipation or occasional use).  Lacks astringent after-effect (Rhubarb) after

Senna - Additional 
  

ContraContra-indications 

Medicinal Actions Vermifuge, diuretic, febrifuge Other uses: laxative candy (bitter taste). 

Gout, colitis, GI inflammation. 

Should not be used with cardiac glycosides. Seeds/pods give gentler action than leaves: more appropriate for the young, elderly and those prone to stomach cramps. NB: Over-use causes Overdependency. Overdose: nausea, bloody diarrhoea, vomiting and nephritis. LongLong-term use: dehydration & electrolyte depletion, worsening constipation and weakening intestinal muscles.

Also used to treat flatulence, gout, fever.  

Topically: poultice prepared with vinegar to treat pimples. NOTE: Senna may cause urine to become reddish ± no clinical significance. 
  

CASCARA

Cascara Bark- Rhamnaceae Bark

Definition: Official cascara sagrada is the dried bark of Rhamnus purshianus. purshianus. Bark is collected from wild trees (depletion is leading to the increase of cultivation)

Cascara 


Rhamnus pershiana (Rhamnaceae) Rhamnaceae) bark extract 

collected, dried and stored for 12 months ( anthraquinone content -> less toxic) discovered 100 years ago Rocky Mtns, W.Coast, US Mtns, W.Coast, griping action harder to eliminate 

modern substance 
 

more violent purgative 
 

Use: Use: night before to clear bowels for x-rays and barium meal

Rhamnus purhsianus - Cascara 

Etymology 

Rhamnos ± Greek, branch, shiny shrub. Purshiana after Pursh, botanist 1st described herb in 1814. 

Other Common Names 

Bearwood, bitterbark, buckthorn, coffeeberry, mountain cranberry, persiana, sacred bark.

Cascara Bark - History 
 

Recently introduced to Modern Medicine. Known to early Mexican and Spanish priests. Not introduced to medicine until 1877.

Cascara ± Collection & Preparation 

Collected form mid-April to end of midAugust, when it separates readily from the rest of the trunk. Longitudinal incisions are made 10cm apart and the bark removed. Tree is then usually felled and the branch bark separated. Bark is then dried in the shade with the cork facing upwards. This is referred to as µnatural¶ cascara. Commercial supplies are comminuted to give small, even fragments called µevenized¶, µprocessed¶, or µcompact¶ cascara.   

Cascara Bark - Storage 

During preparation and storage the bark should be protected from rain and damp (partial extraction of constituents may occur or bark may become mouldy). Should be stored for at least 1 year before use (although no longer a BP requirement). Bark appears to increase in medicinal value up unto its 4 years old (stored bark)  

Cascara Bark ± Why Stored for a Year?  

When stored for at least a year ± better tolerated by patient (less griping pains due to increased peristalsis) Yet as effective as fresh bark. Reason?  

Due to Hydrolysis and other changes that occur during storage. Bitter taste of Cascara can also be reduced by treating the bark with alkali (alkali earths or MgO). 

Chemical constituents:
(i) 4 primary glycosides 

O- and C- linkages C-

To get aglycones FeCl3 To get aloins oxidise with acid

(ii) C-glycosides - two aloins C 

barbaloin ± derived from aloe-emodin aloechrysaloin ± derived from chrysophanol derived from emodin oxanthrone, aloe-emodin, chrysophanol oxanthrone, aloe-emodin, incl. emodin, aloe-emodin, chrysophanol, herterodianthrones emodin, aloe-emodin, chrysophanol, palmidin A B C

(iii) a number of O-glycosides O

(iv) various dianthrones 

(v) aloe-emodin, chrysophanol, emodin in free state aloe-emodin, chrysophanol,

Cascara Bark ± Constituents 1 

4 main glycosides ± Called Cascarosides
Cascaroside A  Cascaroside B  Cascaroside C  Cascaroside D 

Cascara Bark ± Constituents 2 

2 aloins:
C ± Glycosides  Breakdown products of Cascarosides A-D A 
Barbaloin

(derived from aloe-emodin) aloe Chrysaloin (derived from chrysopanol anthrone)

Cascara Bark ± Constituents 3
O-glycosides  Derived from 

Emodin  Emodin oxanthrone  Aloe emodin  chrysophanol 

Cascara Bark ± Constituents 4 

Dianthrones
Those from  Emodin  Aloe-emodin Aloe Chrysophanol 


Hetrodianthrones 
Palmidin

A, B and C (Rhubarb)

Cascara Bark ± Constituents 5
Emodin  Aloe-emodin Aloe Chrysophanol 

(in the free state)

Cascara Bark - Substitutes 


Rhamnus alnifolia (too rare) Rhamnus crocea (bark is very different from official drug) Rhamnus californica (so closely related to Rhamnus purshianus some botanists do not consider them to be separate species). Rhamnus fallax  

Cascara Bark - Uses
Purgative  Similar to Senna  Normally as a tablet  Also used on animals 

Cascara Bark ± Additional 

Physiological Action  

Astringent (bark ± tannins), bitter tonic, chologogue, emetic, hepatic, stomachic.

Excessive use: nausea, vomiting, heamatorrhoea. Long term use: Weakens intestinal muscles. ContraContra-indications: children younger than 14, during pregnancy, lactation, IBS, Crohn¶s, intestinal obstruction, and idiopathic abdominal pain.

Medicinal Uses Move stagnation, clear heat. The most widely used laxative worldworld-wide. Topically: Used as a wash for herpes lesions  

RHUBARB

Rhubarb - Polygonaceae 

Definition: Rhubarb/Chinese Rhubarb is the rhizome of Rheum palmatum. Other palmatum. species and hybrids of Rheum, except R. Rheum, rhaponticum, may rhaponticum, also be included.

Chinese Rhubarb - History 
  

Chinese Rhubarb has a long history. Mentioned in a herbal of 2700BC. Formed an important article of commerce on the Chinese trade routes to Europe. Still used medicinally today.

Chinese Rhubarb ± Collection & Preparation 
    

Rhizomes are grown at high altitudes (+3000m). Collected in Autumn or spring (6-10yrs old) (6Cork is removed, cut. Artificially dried. Packed in tin-lined tinwooden cases. Inferior quality herbs are packed in hessian bags

Chinese Rhubarb - Constituents
1.

Anthraquinones without a carboxyl group ± chrysophanol, emodin, aloealoe-emodin & physcion. Also the glycosides of these substances.

2. Anthraquinones with a carboxyl group (rhein and its glycoside: glucorhein).

Chinese Rhubarb - Constituents
3.

Anthrones and dianthrones of chrysophanol, emodin, aloealoeemodin or physcoin.

5. Hetrodianthrones derived from 2 different anthrone molecules: Palmidin A and Palmidin B. B.

4. Dianthrone glucosides of rhein (Sennosides A and B).

Chinese Rhubarb - Constituents 

Free anthraquinones: anthraquinones: chrysophanol, emodin, aloe-emodin aloeand rhein. Some of the above constituents may also occur as glycosides. 

Chinese Rhubarb - Uses
‡ ‡

‡

‡

Bitter stomachic Diarrhoea (low doses) ± contains tannins Purgative (high doses) ± followed by an astringent effect. Suitable only for occasional for occasional use, not for chronic constipation.

Rhubarb - Additional 

Etymology  

Topical Uses: 

Rheo ± Greek, µto flow¶, in reference to the purgative properties. 

Medicinal Actions 

Poultice to treat boils, burns, wounds. Used to stop bleeding (tannins ± stypic and astringent). Used as a mouthwash for oral ulcers.

AntiAnti-helminthic, antiantibacterial, antiantiinflammatory, antiseptic, astringent (low doses), sialagoge, vulnerary 

Other uses: Acid content: fresh root can be used to polish brass. Caution  

Leaves should be avoided ± high calcium oxalate toxic

ALOE VERA

General Information

‡Member of the lily family. ‡240 species of Aloe. ‡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.

Aloe - Liliaceae
Definition: Aloes are the solid residue obtained by evaporating the liquid which drains from the transversely cut leaves of various Aloe species. The juice is usually concentrated by boiling and solidifies on cooling. 


Official varieties are the Cape Aloes from SA and Kenya (Aloe ferox), and (Aloe ferox), the Curacao Aloes from West Indies (Aloe barbadensis). barbadensis).

Preparation of Cape Aloes
Cape Aloes are prepared from the wild plants of Aloe ferox. ferox. Leaves are cut transversely near the base. 200 leaves arranged around a shallow hole in the ground (lined with canvas or goatskin). Cut ends overlap & drain into the canvas. After 6hrs all the juice is collected. Transferred to a drum. Boiled for 4hrs on an open fire. Poured into tins while hot solidifies.

Preparation of Cape Aloes

Cape Aloes - Characteristics 

Dark brown or GreenGreenbrown Glassy masses Thin fragments have a deep olive colour SemiSemi-transparent.   

Cape Aloes - Characteristics 

Powder: green-yellow greenRub 2 pieces of drug together ± powder is found on the surfaces. Characteristic sour odour (rhubarb/apple(rhubarb/apple-tart odour). Taste: nauseous and bitter. Microscopy: powder in lactophenol ± amorphous.    

Characteristics of Curacao Aloes 
 

     

Colour: yellow-brown ± yellowchocolate brown. Poor qualities (overheated) black colour. Opaque Breaks with a waxy facture SemiSemi-transparent More opaque on keeping. Nauseous and bitter taste. Characteristic iodoform odour. Microscopy: lactophenol ± acicular crystals

Aloes - Constituents 
 

C-glycosides Resins Glycosides 

Aloin 


Barbaloin Isobarbaloin 

AloeAloe-emodin

Cape Aloes: Also Contain Aloinoside A & Aloinoside B (O(O-glycosides of barbaloin)

Aloe - Constituents

Unlike C-glycosides, O-glycosides of COAloe are not hydrolysed by heating with dilute acids or alkali.  Can be decomposed with ferric NB: chloride & dilute HLC - NB: Modified Borntrager¶s Test ± oxidative hydrolysis. Anthraquinones give a red colour when shaken with dilute ammonia. 

Aloe Constituents & Chemical Tests:

NB: All Aloes give a strong green fluorescence with borax (characteristic of anthranols) General test for aloes.

History 
 

 

Known as the ³lily of the desert´. Considered the ³plant of immortality´ by many native peoples. Very long history of medical usage« 2200 B.C.- Mentioned on Sumerian B.C.clay tablets. 1550 B.C.- The Ebers Papyrus states B.C.12 recipes for mixing Aloe with other agents to treat human disorders.  Usually the whole leaf was ground and mixed with another medicinal agent.  Used by Cleopatra and Nerfertiti. Nerfertiti.

History Continued
400 B.C.- Extensively traded in the Near East B.C.and Asia. 333 B.C.- The Island of Socotra was captured by Alexander B.C.the Great because of its Aloe supplies. 68 A.D.- Dioscorides wrote a detailed description of Aloe A.D.vera and all of its uses. 200 A.D.- Aloe vera was an important part of Roman A.D.medicine and became extremely popular in Europe in the centuries to come. 1500 A.D.- Introduced to the New World by the Conquistadors A.D.- 

   

Modern History
First modern medical paper published in 1934.  Described how the whole leaf was used to treat radiation dermatitis. Many papers published in the 20th century describing a wide range of medicinal properties. Reports have mainly focused on the antidiabetic, antidiabetic, anticancer, and antimicrobial properties of the whole leaf, gel, or juice of the plant. Many species of Aloe have been studied.    

10 Main Component Groups of Aloe 


Vitamins 
 

Lignins 

Vitamin D, A, C, E and B12 Lipases, proteases, kinases Ca, Na, K, Mg, Mn, Cu, Zn, Mn, Cr, and Se Mono and poly saccharides, glucosaccharides, glucomannans Most important: Aloin, and Aloin, Emodin 
  

Enzymes Minerals 

Inert except when in topical treatments 3% of Aloe Vera gel Cholesterol, Campesterol, Sisosterol, Campesterol, Sisosterol, and Lupeol AspirinAspirin-like 20 amino acids

Saponins 
 

Fatty Acids 

Sugars 

Salicyclic acid 
 

Anthraquinones 

Amino Acids

Aloe and Irritable Bowel Syndrome (IBS)    

Normal: digestive tract absorbs nutrients into blood  bacteria helps breakdown food IBS: unabsorbed food coats the bowel preventing normal absorption Symptoms:Exhaustion, Symptoms:Exhaustion, constipation, diarrhea, and indigestion Colonic Irrigation: loosed and wash out residues

Aloe and Rheumatoid Arthritis  

 

Two main types of arthritis  Osteoarthritis: wear and tear of life  Rheumatoid: autoimmune disease Symptoms: stiff, red, swollen joints Traditional treatment: antiantiinflammatory drugs with steroids Aloe helps repair damage  Mode of Action: stimulate the Cytokines  Varying results

Aloe and Cosmetics 


Added because of known rejuvenating action Mode of Action:  Polysaccachrides act as moisturizers  Stimulates the fibroblasts to replicate faster  Smoothes skin because sticks epidermal cells together which normally flake  Interferes with melanin deposit production which lead to ³liver spots´

Aloe and Diabetes  



Characterized by hyperglycaemia and alterations of glucose and lipid metabolism  Lead to cell damage and elevation of reactive oxygen species Must control blood glucose and lipid levels Aloe shown to reduce blood glucose in diabetic rats

Aloe and Diabetes
Control (mg/dL) Chlosterol Triglycerides Phospholipids Free fatty acids LDLs HDLs 92.6 5.7 735±5.2 80.5±5.7 58.3±3.6 45.1±2.9 26.5±1.7 Control 228.3 15.1 229.3±16.1 163.8±11.1 145.2±10.5 139.2±10.3 21.3±1.6 Diabetic + 300mg/kg Aloe vera 98.3 8.5 79.2±5.2 85.7±5.8 64.7±4.1 48.5±3.1 23.4±1.5 (mg/dL) +600microgram/kg Glibenclamide 106.2 7.0 83.4±5.8 88.8±6.7 66.1±4.6 53.4±3.4 22.03±1.42

Control Diabetic Control 332.27 ±20.80 +300 mg/kg Aloe vera 96.8±5.30 +600microgram/kg Glibenclamide 118.46±6.56

Blood Glucose (mg/dL) Plasma Insulin 85.81 ±5.20 15.86±1.38 5.12±0.68 14.12±1.48 12.52±0.69

Aloe and Diabetes  

Decrease in blood glucose due to stimulation of insulin secretion Decrease in cholesterol, triglycerides, phospholipids, and free fatty acids from increased clearance and decreased transporters

Anti-Microbial/Anti-Microbial/-Bacterial 
   

50% gel leaf solution, complete inhibition of Staphylococcus aureus Due to phenolics Efficacy of gel or leaf? S. aureus inhibited by both Other bacteria inhibited by just leaf or gel

Aloe, Antimicrobials, and Wounds  

When aloe is combined with other anti-microbials, antia wound heals faster than with the anti-microbial antialone. Possibly due to its moisturizing capability as well.

Immune Booster?  



Asian practice of ingesting herbs to support the immune system May have a direct inhibitory effect on microbes Also, selectively modulates cells of the immune system

Alveolar Osteitis
Dry Socket (Wisdom teeth extraction) Acemannan Hydrogel (from clear inner gel of aloe vera) vera)  Normal treatment 7.6% develop AO  With Acemannan 1.1% develop AO  

Normal

Dry socket, clot does not form properly

Burn Treatment 
 

Shows increased healing effects on 2nd degree burns AntiAnti-inflammation and wound healing promotion Vessels return to normal size quicker than with untreated burns

Aloe and Cancer  

 

AloeAloe-emodin induces apoptosis in T24 human bladder cancer cells Inhibits cell viability, induces G2/M arrest MechanismMechanism- p53, p21, caspase activation Treat Radiation Symptoms?

Neuroectodermal Cancer
Inhibits neuroectodermal tumors in mice. Few toxic effects, does not inhibit normal fibroblasts. Induces apoptosis and is specific to a tumor energyenergydependent pathway of drug incorporation  



Cancer U-373 Glioma Cells U   

Aloe emodin Regulation of cell cycle, cell proliferation and protein kinase C (PKC) Inhibits S phase Suppresses PKC activity

Gastric and Colorectal Cancers  



Aloe vera and Aloe arborescens did not suppress tumor growth Life prolongation up to 32% in mice Dose dependent

Products 
  



Gel and latex. GelGel- leaf pulp or mucilage obtained from the parenchymal tissue. LatexLatex- bitter, yellow substance obtained from pericyclic tubules just beneath the outer skin of the leaves. (otherwise called µAloe juice¶) These terms are often confused by consumers. Using a freshly cut leaf is thought to be the most effective treatment.

Summary
Dental Health and Hygiene 2. Provides Rapid Soothing 3. Aids in Healthy Digestion 4. Immune Support and Function Regulates Weight and Energy Levels 6. Collagen and Elastin Repair 7. Daily Dose of Minerals 8. Daily Dose of Vitamins 9. AntiAnti-inflammatory Properties 10. Essential Amino Acids
1.

5.

Aloe - Uses 

Purgative Seldom prescribed alone ± activity is increased when administered with small quantities of soap or alkaline salts; Carminatives moderate griping tendency. Ingredient in Friar¶s Balsam.  

Aloe ± Additional Notes 

Medicinal Uses:  

Etymology 

AntiAnti-bacterial, anti-fungal, antichologoge, emmenogogue, antianti-inflammatory (juice), antianti-inflammatory , demulcent, vulnerary, immuneimmune-stimulating (gel).

Name derives from Arabic alu, meaning shiny or bitter in reference to the gel. 

Other uses 

Radiation burns (internal and external use) 

ContraContra-indications
Pregnancy & lactation (internal uses) 

KhoiKhoi-San hunters rub gel on their bodies to reduce sweating and mask their scent. Used to break nail-biting nailhabit.

Aloe vera Products    

These are derived from the mucilage gel ± parenchyma cells Should not be confused with aloes (juice of pericycle ± juice used for laxative effect). Cosmetic industry (usefulness often exaggerated) - Used as suntan lotions, tonics and food additives. Mucilage = polysaccharide of glucomannans and pectin

COCHINEAL

Cochineal  

Definition: Cochineal is the dried female insect, Dactylopius coccus, coccus, containing eggs and larvae. Insects are indigenous to Central America, commercial supplies are derived from Peru. 

Eggs are protected during the rainy season are µsown¶ on cacti ± on which it is intended to breed. Both male and females arise. After a time, fecundation occurs. Females attach themselves to the cacti and the males die out. Females swell to x2 their original size due to developing larvae & develop red colouring matter.

Cochineal  

Cochineal 

Larvae mature after 14days and escape from the now dead body of the parent. Only a small portion develop into males. For next 2 weeks, males fly and young females crawl on the plant. Life cycle = 6 weeks. 3-5 generations may be produced in 1 season.    

Cochineal - Collection 
  

 

Insects are brushed from plants with small brooms and killed (some left to provide for subsequent crops). First crop killed contains the most colouring matter. Insects are killed by plunging them in boiling water, stove heat or exposure to fumes by burning sulphur or charcoal. If heat is used ± insects change to purple ± black ± called µblack grain¶. Fume killed ± turn purple-grey called µsilver purplegrain¶. Small immature insects and larvae which can be separated by sieves are sold as µgranilla¶ or siftings.

Cochineal Collection

Cochineal - Characteristics
Oval in shape Half cm in length Examined microscopically after removing the colouring matter (ammonia solution). Each insect contains 60 ± 450 eggs and larvae.

Cochineal - Constituents 
   

C-glycoside ± anthraquinone derivative purple, water-soluble colouring matter waterCarminic acid Fat Wax

bright 

Adulteration: occurs by increasing the weight of the insects by µdressing¶ it with inorganic matter in a colour which blends in with that of the insect. Detected when insects are placed in water

Last Word on Anthraquinones 

Anthraquinones take about 10hours to produce an effect (take overnight) Should not be used for more than 10 days. Should not be used by children, pregnant and lactating women. Cause griping pain. Are habit-forming. habitAnthraquinones = phenolic glycosides, used as an irritating laxative   

 

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