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PLANT GLYCOSIDES
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Glycoside Definition
A substance which on hydrolysis
yields a reducing sugar
+ one or more non-sugar substances(genin/aglycone)
Normally aromatic in nature
Known as the aromatic aglycone or geninportion
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Glycosides
Glycoside = Broad & general term
Embraces all the many variouscombinations of sugars & aglycones
e.g. Cardiac glycosides, flavonoidglycosides, phenolic glycosides etc.
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Glycoside Formation
In nature: Formed by theinteraction of thenucleotide of a sugargroup with the alcoholic
or Phenolic group of a2nd compound.
This glycoside is called an
O-glycoside
Most numerous kindfound in nature
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Other Glycoside Formation
Other glycosides occurthrough
sulphur links Called S-glycosides
Nitrogen links Called N-glycosides
Through Carbon links Called C-glycosides
NOTE:Reactions for both the formation and Hydrolysis ofl cosides are reversible
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Glycosidal Reduction
Glycosides themselves do not reduceFehlings solution, But the simple
sugars they produce on hydrolysis(aglycones) do (precipitate red cuprousoxide)
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Glycosidal Sugars
Sugars found in glycosides may be
Monosaccharides
Glucose Rhamnose
Fructose
Deoxysugars (more rare)
Cymarose
E.g. those found in the cardiac glycosides
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Terms used to DescribeGlycosides
A Glycoside is a
Glucoside Has glucose as the sugar component
Pentoside Has a sugar such as arabinose
Rhamnosides Contains rhamnose
Rhanmoglucosides Contains both rhamnose and glucose
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Terms used for Aglycones
Normally self-explanitory
E.g. Phenol
Anthroquinone
Sterol glycoside
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Other Glycosidal Terms
saponin (soap-like)
Cyanogenic (producing hydrocyanic acid)Cardiac (having an action on the heart)
Terms: Are used to group glycosidestogether which have similar functions &chemical structure.
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GLYCOSIDE STRUCTURE
2 types of genin are distinguished Based on the structure of the lactone ring
5-membered ring bufanolides orbufadienilolides
E.g. scillarenin
6-membered ring cardinolides or cardiacactive glycosides (medicinally more significant)
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Cardio-Active Glycosides
A small group of plantglycosides act directlyon the heart muscle.
These include (but are
not limited to cardiacglycosides orcardenolides)
Cardenolides aresteroidal glycosides
exert a slowing andstrengthening effect onthe failing cardiacmuscle.
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Cardenolide
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Cardiac Glycosides
E.g. Digitalispurpurea(PurpleFoxglove).
Other uses of theplant (and glycoside)include being used asarrow poisonings.
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Pharmacological Action of CardiacGlycosides
Effectiveness depends on both theaglycones and the sugar attachments.
Medicinal action depends on theaglycone
But the sugars make the compoundmore soluble in increases the fixationof the glycoside to the heart muscle
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Pharmacological Action of Cardiac
Glycosides The overall action of Digitalisglycosides is complicated
by the number of different effects produced.
The exact mode of action on the myocardial muscle stillneeds investigation.
It is thought to act in competition with K ions for specificreceptor enzymes (ATPase) sites in the cell membranesof the heart muscle when there is an influx of Na ions.
Effect is to increase the force of heart contraction
Diuretic action relates to the improved circulatory effects.
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Digitalispuruperea(Scrophulariaceae)
Description: A perennial herbgrowing up to 1.5m with asingle erect stem, broad lance-shaped leaves and bell-shaped, purple-pink or whiteflowers in long spikes
History: The poisonousnature of the leaves are wellknown, and the drug wasrecommended for use since1542.
Discovered by WilliamWithering, an 18th centurycountry doctor (cardiac effect)
His work led to the productionof a life-saving medicine
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7/31/2019 Plant Glycosides 2
18/48
Digitalispurpurea PurpleFoxglove
Definition:
Digitalisconsists ofthe dried leaves of
Digitalispurpurea. It is required to
contain at least 0.3%of total cardinolidescalculated asdigitoxin.
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7/31/2019 Plant Glycosides 2
19/48
Digitalispurpurea
Parts Used:
Leaves
Habitat: Native to Western Europe. Although the plantis cultivated, wild plants are thought to be superior.
Collection:
First or second-year leaves are permitted.
After collection the leaves should be dried as soon aspossible at a temperature of about 60C.
Stored in airtight containers & protected from light.
Moisture content should be no more than 6%.
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-5053_TN.jpg&imgrefurl=http://www.acclaimimages.com/search_terms/cartoons.html&h=100&w=94&sz=5&hl=en&start=2&tbnid=OuW-LIlsNnk63M:&tbnh=82&tbnw=77&prev=/images%3Fq%3Dheart%2Bcartoons%26gbv%3D2%26hl%3Denhttp://images.google.co.za/imgres?imgurl=http://67.15.62.77/_gallery/_TN/0093-0610-0810-5053_TN.jpg&imgrefurl=http://www.acclaimimages.com/search_terms/cartoons.html&h=100&w=94&sz=5&hl=en&start=2&tbnid=OuW-LIlsNnk63M:&tbnh=82&tbnw=77&prev=/images%3Fq%3Dheart%2Bcartoons%26gbv%3D2%26hl%3Denhttp://images.google.co.za/imgres?imgurl=http://67.15.62.77/_gallery/_TN/0093-0610-0810-5053_TN.jpg&imgrefurl=http://www.acclaimimages.com/search_terms/cartoons.html&h=100&w=94&sz=5&hl=en&start=2&tbnid=OuW-LIlsNnk63M:&tbnh=82&tbnw=77&prev=/images%3Fq%3Dheart%2Bcartoons%26gbv%3D2%26hl%3Denhttp://images.google.co.za/imgres?imgurl=http://67.15.62.77/_gallery/_TN/0093-0610-0810-5053_TN.jpg&imgrefurl=http://www.acclaimimages.com/search_terms/cartoons.html&h=100&w=94&sz=5&hl=en&start=2&tbnid=OuW-LIlsNnk63M:&tbnh=82&tbnw=77&prev=/images%3Fq%3Dheart%2Bcartoons%26gbv%3D2%26hl%3Denhttp://images.google.co.za/imgres?imgurl=http://67.15.62.77/_gallery/_TN/0093-0610-0810-5053_TN.jpg&imgrefurl=http://www.acclaimimages.com/search_terms/cartoons.html&h=100&w=94&sz=5&hl=en&start=2&tbnid=OuW-LIlsNnk63M:&tbnh=82&tbnw=77&prev=/images%3Fq%3Dheart%2Bcartoons%26gbv%3D2%26hl%3Den 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7/31/2019 Plant Glycosides 2
20/48
Digitalispurpurea- Collection There is a general belief that the
pharmacological activity of the leaves increaseduring the course of the day to reach amaximum in the early afternoon (when theyshould be harvested).
This was supported by assays done in 1956which showed a greater activity of the leaves atnoon than 8am, irrespective of if the leaves
where in the sun or shade. However, other work indicates that there is no
glycosidal content variation of the leaves whenmeasured at 3-hour intervals.
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-5053_TN.jpg&imgrefurl=http://www.acclaimimages.com/search_terms/cartoons.html&h=100&w=94&sz=5&hl=en&start=2&tbnid=OuW-LIlsNnk63M:&tbnh=82&tbnw=77&prev=/images%3Fq%3Dheart%2Bcartoons%26gbv%3D2%26hl%3Denhttp://images.google.co.za/imgres?imgurl=http://67.15.62.77/_gallery/_TN/0093-0610-0810-5053_TN.jpg&imgrefurl=http://www.acclaimimages.com/search_terms/cartoons.html&h=100&w=94&sz=5&hl=en&start=2&tbnid=OuW-LIlsNnk63M:&tbnh=82&tbnw=77&prev=/images%3Fq%3Dheart%2Bcartoons%26gbv%3D2%26hl%3Denhttp://images.google.co.za/imgres?imgurl=http://67.15.62.77/_gallery/_TN/0093-0610-0810-5053_TN.jpg&imgrefurl=http://www.acclaimimages.com/search_terms/cartoons.html&h=100&w=94&sz=5&hl=en&start=2&tbnid=OuW-LIlsNnk63M:&tbnh=82&tbnw=77&prev=/images%3Fq%3Dheart%2Bcartoons%26gbv%3D2%26hl%3Den 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7/31/2019 Plant Glycosides 2
21/48
Microscopical Characteristics
Stomata and hairspresent on both surfaces(more on lower surface)
No calcium oxalate
Clothing hairs are
uniseriate
Glandular hairs
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7/31/2019 Plant Glycosides 2
22/48
Active Constituents
glycosides purpurea glycoside A
purpurea glycoside B
(2 main actives in the fresh leaf)
Glucogitaloxin
At C-3 of the genin: a linear chain of 3digitoxose sugar moieties terminated byglucose
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7/31/2019 Plant Glycosides 2
23/48
Active Constituents
On drying: enzymedegradation takes place loss of the terminalglucose. Produces
Digitoxin Gitoxin Gitaloxin
(main actives in driedleaves)
Poor storage leads tofurther hydrolysis andcomplete loss of action
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-5053_TN.jpg&imgrefurl=http://www.acclaimimages.com/search_terms/cartoons.html&h=100&w=94&sz=5&hl=en&start=2&tbnid=OuW-LIlsNnk63M:&tbnh=82&tbnw=77&prev=/images%3Fq%3Dheart%2Bcartoons%26gbv%3D2%26hl%3Denhttp://images.google.co.za/imgres?imgurl=http://67.15.62.77/_gallery/_TN/0093-0610-0810-5053_TN.jpg&imgrefurl=http://www.acclaimimages.com/search_terms/cartoons.html&h=100&w=94&sz=5&hl=en&start=2&tbnid=OuW-LIlsNnk63M:&tbnh=82&tbnw=77&prev=/images%3Fq%3Dheart%2Bcartoons%26gbv%3D2%26hl%3Denhttp://images.google.co.za/imgres?imgurl=http://67.15.62.77/_gallery/_TN/0093-0610-0810-5053_TN.jpg&imgrefurl=http://www.acclaimimages.com/search_terms/cartoons.html&h=100&w=94&sz=5&hl=en&start=2&tbnid=OuW-LIlsNnk63M:&tbnh=82&tbnw=77&prev=/images%3Fq%3Dheart%2Bcartoons%26gbv%3D2%26hl%3Denhttp://images.google.co.za/imgres?imgurl=http://67.15.62.77/_gallery/_TN/0093-0610-0810-5053_TN.jpg&imgrefurl=http://www.acclaimimages.com/search_terms/cartoons.html&h=100&w=94&sz=5&hl=en&start=2&tbnid=OuW-LIlsNnk63M:&tbnh=82&tbnw=77&prev=/images%3Fq%3Dheart%2Bcartoons%26gbv%3D2%26hl%3Den -
7/31/2019 Plant Glycosides 2
24/48
Digitalis Active Constituents
also contains anthraquinone glycosides
Saponins
Sopogenins
Flavonoids
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7/31/2019 Plant Glycosides 2
25/48
Active Constituents
Other glycosides (present in smallerquantities) include
Digitalose
Glucose
Verdoxin (x3 more toxic than gitaloxin)
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7/31/2019 Plant Glycosides 2
26/48
Digitalis Active Constituents
It is generally agreed that the first-yearleaves collected in Jan-Feb (SouthernHemisphere) have the highest content of
total glycosides. After that they decreaseduring the winter months. After thatanother peak is reached during the time of
flowering, but not as high as the first one.
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7/31/2019 Plant Glycosides 2
27/48
Digitalis Medicinal Actions
tonic effect on the diseased heart
glycosides enable the heart to beat more
strongly, slowly and regularly, withoutusing or needing more O2.
Stimulates urine production lesseningthe load on the heart.
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7/31/2019 Plant Glycosides 2
28/48
NB!
Kellar-Keliani Test for digitoxise
Pg 509/Pg146
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7/31/2019 Plant Glycosides 2
29/48
Digitalispurpurea
Allied Drugs
D. thaspi
D.