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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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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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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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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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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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Digitalis Active Constituents

also contains anthraquinone glycosides

Saponins

Sopogenins

Flavonoids

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Active Constituents

Other glycosides (present in smallerquantities) include

Digitalose

Glucose

Verdoxin (x3 more toxic than gitaloxin)

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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

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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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Digitalispurpurea

Allied Drugs

D. thaspi

D.