Glycosides

Glycosides
Presented by
Name : Sadia Afrin Prova
Batch: 192
Dept: Department of Pharmaceutical Sciences,
Institution: North South University.
Course : Pharmacognosy (PHR 113)

Table of
Contents
05. 06. 07. 08.
Aloe
barbadensis
Prunus serotina Glycyrrhiza
glabra
Vanilla planifolia
01.
Introduction
02.
Digitalis
purpurea
03.
Strophanthusgr
atus
09.
References
04.
Cascara sagrada

Introduction
Glycosides are the organic compounds usually of plant origin and found in some animals, formed by the bond between sugar and
non-sugar moiety. These compounds upon hydrolysis yield one or more sugars (glycone) β_form and non-sugar (aglycone). The
linking between glycone and aglycone is usually an oxygen or ether linkage.
Sugar part of Glycosides: The most common sugar or glycone is beta-D glucose, but Rhamnose, Digitoxose, Cymarose, and
other sugars also present in glycosides. It is possible to find the alpha form of glycosides, but only the beta form is found in plants.
When the sugar form is glucose, the substance may also be called a glucoside.
Non-sugar part of Glycosides: This non-sugar or aglycone is the active part of glycoside, responsible for giving the
therapeutic effect. The sugar part gets hydrolyzed to facilitate glycoside absorption, transportation of aglycone to the site of action.
Classification of Glycosides:
 The glycosides are classified based on the type of aglycone in glycoside, such as as- Anthraquinone glycoside, Saponin glycoside,
Aldehyde glycoside, Phenol glycoside, etc.

The glycosides are classified based on the type of glycone in glycoside, such as as- Glucose-glucoside, Rhamnose- rhamnoside,
Digitoxose- digitoxoside, Arabinose-arabinoside, etc.
The third classification is based on the therapeutic effect given by glycoside such as- Cardiac glycosides ( Digitalis,
Strophanthus), Laxative glycosides ( Cascara sagrada, senna).
The fourth classification is based on the type of linkage between the sugar and non-sugar parts such as C- glycoside, N-
glycoside, O- glycoside, and S-glycoside. Here, the sugar part is linked to the carbon, nitrogen, oxygen, and sulphur atom of the
aglycone part, respectively.
Importance of Glycosides: Glycosides are present in a wide of varieties. They play an essential role in animal life with
wide varieties of therapeutic effects. The compounds present in the glycoside include many therapeutic agents that almost give
every pharmacological actions possible. Glycoside is used in making traditional and modern medicines such as purgative,
cathartics, anti-ulcers, etc.

Digitalis purpurea
Name: Foxglove, Purple Foxglove, Lady’s Glove, Digitalis.
Biological Name: Digitalis purpurea
Family: Scrophulariaceae (the figwort family)
Geographical Sources: Digitalis pupurea is a species of
biennial or annual flowering herb widely known and naturalized in
the United Kingdom and most of Europe, including some
Mediterranean regions in Italy. It can be found abundant locally in
the various habitats of Ireland, excluding the midlands. It is also
present in Britain, Deutschland, France, India, Kurdistan, Iraq, Japan,
Mexico, Nepal, Spain, and Turkey. Foxgloves are manufactured
commercially in the Netherlands and Eastern Europe.

Chemical Constituents
Digitalis purpurea includes 35
cardiac glycosides, including
digitoxin, digoxin, ouabain,
oleandrin, proscillaridin and
digitalin, and the saponin
digitonin.
Digitalis leaves contain 0.2–0.45% of both primary and secondary glycosides. Primary glycosides such as Purpurea glycosides A
and B are present in the fresh digitalis leaves. Their hydrolysis yields digitoxin and glucose or gitoxin and glucose, respectively.
Digitalis leaves also contain glycosides like odoroside-H, gitaloxin, verodoxin, and glucoverodoxin.
The constituents include oxidase enzymes, volatile oil, fatty matter, starch, gum, and sugars.

Uses:
Digitalis and its cardiac glycosides (particularly digoxin and
digitoxin) are used to treat congestive heart failure as cardiotonic
agents.
It is used for the treatment of Atrial fibrillation. Digitoxin rapidly
strengthens the heartbeat then very slowly excretes it.
By improving contractility and strengthening the cardiac muscle tone, it treats Atrial flutter, allowing the heart to pump more
steadily, vigorously, and consistently without the need for more oxygen.
The foxglove is a commonly used herbal medicine with a recognized cardiac stimulatory effect. The leaves are cardiac, diuretic,
stimulant, and tonic and used for the benefit in the treatment of dropsy.
Digitalis has also been employed in treating internal haemorrhage, inflammatory diseases, delirium tremens, epilepsy, acute
mania, and various other diseases.

Name: Climbing Oleander
Biological Name: Strophanthus gratus
Family: Apocynaceae
Geographical Sources: Strophanthus gratus, a climbing evergreen shrub, is native to tropical Africa and southern Africa. The
other varieties of Strophanthus gratus are found in some of the parts of Asia. It can be found in primary and secondary moist forests,
mostly at the edges of forests and thickets up to 650 m from sea level. For local use as medicine and export, Cameroon, Nigeria, and
Gabon harvest the wild plants. It is commonly cultivated as an ornamental climbing plant in the tropics and greenhouses' temperate
region and is highly prized for its rose-scented blossoms.
Strophanthus gratus

Ouabain
Many cardiac glycosides (cardenolides) have been isolated from the palnts of Strophanthus gratus species. The leaves contain
the lignans pinoresinol, 8-hydroxypinoresinol, and olivil.
Strophanthus gratus seeds contain 4–8% of a glycoside mixture with predominantly ouabagenin as aglycone: 90–95% is
ouabain (g-strophanthin), followed by acolongifloroside K, and strogoside, which has strogogenin as aglycone. Minor
components include different aglycones such as sarnovide and several sarmentosides.

Uses:
 The plant is significant in herbal medicine, having anti-
inflammatory and antioxidant action.
 The leaves are used to treat gonorrhoea and constipation.
An infusion of the leaves is rubbed on the body to cure
fever and to treat snakebites.
 The leaves used for healing and are added to guinea-
worm sores.
 The root decoction is reported to be an aphrodisiac.
 A decoction of the bark is taken to treat weakness.
 The seeds containing glycosides, particularly ouabain, are
used as rapid cardiac and vascular stimulants to treat
congestive heart failure.
 Many tribal groups use S. gratus in making poisonous
hunting arrows.

Cascara sagrada
Name: Cascara buckthorn, Cascara sagrada, Cascara, Bearberry.
Biological Name: Rhamnus purshiana
Family: Rhamnaceae
Geographical Sources: Cascara sagrada is a large shrub
native to North America, British Columbia, Canada, and Kenya.
The bark collected from the wild trees (growing to 6–12 m in
height) is also known as California buckthorn, yellow bark, and
sacred bark. Most of the present-day market supply comes from
Oregon, Washington, and southern British Columbia. The dried,
aged bark of R. purshiana has been used continually for many
years by both Pacific northwest native peoples and immigrant
Euro-Americans as a natural laxative medicine.

 Two types of anthracene compounds are
found in the tree. They are the normal O-
glycosides (based on emodin, 10-20%) and
aloinlike C-glycosides, about 80-90% of total
glycosides.
 The C-glycosides present in cascara are aloin
or barbaloin and deoxy barbaloin or
chrysaloin. Four primary glycosides or
barbaloin and deoxy barbaloin or chrysaloin. Four primary glycosides or cascarosides A, B, C, and D containing both O- and C-
glycosidic linkages are also present. Cascarosides A and B are the primary glycosides of aloin, and cascarosides C and D are
primary glycosides of chrysaloin. Sevel O-glycosides (10–20%) derived from emodin oxanthrone, aloe-emodin, and chrysophanol
are present in Cascara.
 Fresh cascara bark contains anthranol derivatives which on storage gets oxidized to anthraquinone.
 It also contains heterodianthrones like Palmidins A, B, and C, and a bitter lactone.
 Apart from glycosides, also contains fat, starch, glucose, volatile odorous oil, malic and tannic acids.

Cascara Sagrada Bark
Uses:
Cascara sagrada is widely used to treat constipation and
chronic constipation. The anthraquinones in the bark do
peristalsis, increasing the bowel movement's speed and
restoring the colon's usual tone. Thus, Cascara sagrada is
used as a natural laxative.
The bark also has tonic properties, promoting gastric
digestion and appetite.
The C. sagrada is also taken internally in the treatment of
haemorrhoids, liver problems, and jaundice.
Cascara is also used in veterinary work.

Name: Aloe vera, Barbados aloes
Biological Name: Aloe barbadensis miller
Family: Asphodelaceae
Geographical Sources: Aloe barbadensis miller is a shrubby, perennial, xerophytic, succulent species pf plant mostly growing
in African, Asian, European, and American drylands. Aloe Barbadensis is mainly from Northern Africa but was introduced in the
seventeenth century to the Barba dos Islands. Curaçao aloe, which is sometimes referred to as "Barbados aloe," produced from
cultivated plants of A. barbadensis, is an essential form occurring in the USA. It is also cultivated in India, mostly in Rajasthan, Andhra
Pradesh, Gujarat, Maharashtra, and Tamil Nadu.
Chemical Constituents:
 Aloe, the dried latex of the leaves of Aloe barbadensis, contains anthraquinone glycosides, the principal one is barbaloin (aloe-
emodin anthrone C-10 glucoside).
 Curaçao aloe also contains substantial chrysophanic acid, both free and mixed.
 Aloe also contains large amounts of resin (16-63%) and a pale-yellow volatile oil.
Aloe barbadensis

Uses:
Aloe gel has healing properties by which it increases the degree of collagen cross-linking and changes its composition of the
wound. So, it is used for the healing of wounds and injuries.
It is found in the compound benzoin tincture as a pharmaceutical excipient.
Aloe vera gel has been reported to have a protective effect against radiation damage to the skin. The fresh juice has been used for
the treatment of burns, abrasion, and other skin irritations.
Aloe is used as a cathartic. The aloe glycosides elicit a relatively drastic cathartic action.
Aloe vera is used in cleansers, toners, and creams. It has an anti-acne and anti-aging effect and moisturizes the skin.
Leaf

Prunus serotina
Name: Virginian Prune, Wild Black Cherry, Virginian Bark, Black
Cherry.
Biological Name: Prunus serotina
Family: Rosaceae
Geographical Sources: Prunus serotina, commonly referred to
as a black cherry, is a species of evergreen shrub/tree indigenous to
North America, Mexico, and Central America. The plant is extensively
spread from south-eastern Canada across the United States to Ontario
and Florida and westward to Dakota and marginalized communities in
central Texas. In Missouri, it is typically found in lowland and highland
forests and streams all over the state. In the mid 20th century, Prunus
serotina was introduced as an ornamental tree in Western and Central
Europe and became naturally localized .

The Wild Cherry bark contains prunasin, a
cyanogenetic glycoside (D-mandelonitrile
glucoside), and an enzyme prunase. The
partial hydrolysis of amygdalin yields
prunasin.
Prunasin's hydrolysis, in the presence of
water and prunase enzymes, yields
benzaldehyde, glucose, and hydrocyanic
acid (about 0.07–0.16%).
The other constituents include benzoic
acid, p-coumaric acid, coumarin derivative
scopoletin, starch, resin, tannin, gallic acid,
fatty matter, lignin, red coloring matter,
salts of calcium, potassium, and iron, and
traces of a volatile oil associated with
hydrocyanic acid.

Uses:
P. serotina is often planted as an ornamental tree, especially in fall.
The tree is used as an astringent tonic, pectoral, sedative, and expectorant. It has been used in the treatment of bronchitis,
catarrah, whooping cough, and dyspepsia.
The wild cherry syrup is mainly prepared from the inner bark, which gives a sedative taste with mild sedative properties. It is useful
useful for the treatment of irritable and persistent coughs.
The strong reddish-brown wood is commercially used for making a large number of products, including furniture and panels,
veneers, cabinets, toys, gun stocks, instrument/tool handles, and musical instruments.
The fruits are used to make jams, jellies, wines and have also been used to flavour certain liquors such as brandy and whiskey.

Black Cherry Prunus serotina Bark

Glycyrrhiza glabra
Name: Liquorice, Radix Glycyrrhizae, Sweet licorice.
Biological Name: Glycyrrhiza glabra
Family: Fabaceae
Geographical Sources: Glycyrrhiza glabra, commonly known as licorice, is a perennial herb about 1.5 m, indigenous to Spain,
Italy, England, France, Germany, and the USA. The plant is abundant in the wild state in Galicia and central and southern Russia. It
grows in fertile, gravel, or sandy soil along a river or stream where water is sufficient for the plant to thrive. G. glabra yields The
'Persian' licorice, collected in the Tigris and Euphrates' valleys in Iran and Iraq.
 Glycyrrhiza glabra root contains a saponin like glycoside, Glycyrrhizin (6–8%), which is 50 times sweeter than sugar. Upon
hydrolysis, glycyrrhizic acid is converted to the aglycone glycyrrhetic acid or glycyrrhetinic acid. Glycyrrhetic acid and triterpenoid
aglycone, associated with glucuronic acid disaccharide, can be found naturally as calcium and potassium salts in licorice root.
 Other compounds include flavonoid glycosides, such as liquirtin, isoliquirtin, rhamnoliquirilin, rhamnoisoliquirilin),
licopyranocoumarin, glisoflavone, licoarylcoumarin, shinpterocarpin, shinflavanone

The drug also contains sugar, starch (29%), gum, protein, fat (0.8%), resin, asparagin (2–4%), a trace of tannin in the outer bark of
the root, yellow colouring matter- chalcone glycoside isoliquiritin, and volatile oil (0.03%).

Uses:
 Glycyrrhiza is used considerably as flavouring agent and sweetening agent to mask the taste of bitter drugs.
 Commercially it is also used in chewing gums, cigarettes, chewing tobacco, chocolate candy for its sweetening properties. It is
also used in beer to increase the foaminess and root beer, stout, and porter to provide a bitter taste.
 It acts as an expectorant to treat bronchial problems such as catarrh, sore throat, bronchitis, colds, flu, and coughs. It also has
demulcent effects.
 Traditionally, licorice has also been used to treat many diseases such as asthma, tonsillitis, hyperdipsia, acidity, leucorrhoea,
bleeding, hemorrhagic diseases, and jaundice.
 It is a potent healing agent for tuberculosis.
 Glycyrrhiza is also used for its value in reducing fevers (glycyrretinic acid has an effect like aspirin), and it may have an
antibacterial action as well.
 It is used to treat chronic inflammation such as arthritis and rheumatic diseases, chronic skin conditions, and autoimmune
diseases in general.
 The licorice root extract is used for the treatment of peptic ulcer and Addison’s disease. Externally, the root is used in the
treatment of herpes, eczema, and shingles.

Vanilla planifolia
Name: The vanilla
Biological Name: Vanilla planifolia
Family: Orchidaceae
Geographical Sources: Vanilla planifolia, commonly called vanilla, is a
perennial, climbing terrestrial or epiphytic orchid vine native to Mexico and
Central America. Vanilla seed pods were known to the Aztecs of Mexico for its
flavoring qualities and were used to flavor cocoa. However, they were
unknown to the rest of the world until 1520 when the Spaniards brought the
plants from Mexico to Spain, and consequently, its use became popular in
Europe. At present, vanilla is the world's most important spice; 75% of the
trees are cultivated in Madagascar, Comores, and the Reunion Islands, with
the rest primarily coming from Indonesia, Tonga, Tahiti, and Mexico. 95% of
the world's traded vanilla is derived from Vanilla panifolia species.

Green vanilla contains two glycosides glucovanillin (avenein)
and glucovanillic alcohol. During the curing process, the
hydrolysis of glucovanillin by an enzyme yields vanillin. On the
other hand, glucovanillic alcohol is hydrolyzed into glucose and
vanillic alcohol. In turn, vanillic alcohol becomes oxidized into
vanillin ((4-hydroxy-3-methoxy benzaldehyde), which is primarily
primarily responsible for vanilla's characteristic flavor and smell.
The natural vanilla taste and flavour are derived from this
orchid's seed pods, as the seed pod contains approximately 3.5%
3.5% vanillin.
The other compounds include sugar (10%), fixed oil (10%), and
and calcium oxalate.

Uses:
The seedpods, whole fruit, powder, or fruit extract of vanilla are used as flavouring agents in a wide range of foods such as ice
creams, confectionery, baked goods, puddings. It is also used in foods to reduce the amount of sugar needed for sweetening.
 It is also among the essential fragrance in perfumery.
Vanilla seedpods have aphrodisiac effect property for . . which its
use is widespread in aromatherapy and can . . alleviate anxiety,
calm, relax and soften anger, frustrations, . . and irritability with its sweet
fragrance.
Vanilla is used as a flavouring agent in making . . . pharmaceutical
preparations such as syrups.
Vanilla is used as an antioxidant.
Traditionally, the seed pods are used as carminative, emmenagogue, and stimulant. They are used to cure fevers, spasms and
caries, and gastric complaints.

References
1. Digitalis purpurea
• William Charles Evans, et al. Trease and Evans’ Pharmacognosy. 16th ed., Edinburgh, Saunders/Elsevier, 2009.
• B Shah. Textbook of Pharmacognosy and Phytochemistry. 1st ed., 2009.
• Tyler, Varro E, et al. Pharmacognosy. Philadelphia, Lea & Febiger, 1998.
• Al-Snafi, Ali. (2017). PHYTOCHEMICAL CONSTITUENTS AND MEDICINAL PROPERTIES OF DIGITALIS LANATA AND DIGITALIS
PURPUREA-A REVIEW. Indo Am J P Sci. 4. 225-234. 10.5281/zenodo.344926.
• Negi, J.S, et al. “Determination of Mineral Contents of Digitalis Purpurea L. and Digitalis Lanata Ehrh.” Journal of Soil Science
and Plant Nutrition, no. ahead, 2012, pp. 0–0, 10.4067/s0718-95162012005000008. Accessed 30 Apr. 2020.
• https://pfaf.org/user/Plant.aspx?LatinName=Digitalis+purpurea
• Al-Snafi, Ali. (2017). PHYTOCHEMICAL CONSTITUENTS AND MEDICINAL PROPERTIES OF DIGITALIS LANATA AND DIGITALIS
PURPUREA-A REVIEW. Indo Am J P Sci. 4. 225-234. 10.5281/zenodo.344926.
2. Strophanthus gratus
• Ofori – Baah, Samuel, and Lawrence Sheringham Borquaye. “Ethanolic Leaf Extract from Strophanthus Gratus (Hook.) Franch.
(Apocynaceae) Exhibits Anti-Inflammatory and Antioxidant Activities.” Cogent Biology, vol. 5, no. 1, 31 Dec. 2019,
10.1080/23312025.2019.1710431. Accessed 7 Feb. 2020.
• http://tropical.theferns.info/viewtropical.php?id=Strophanthus+gratus
• https://conservatoryofflowers.org/bloom/strophantus-gratus/

3. Cascara sagrada
• https://www.verywellhealth.com/cascara-sagrada-89046
4. Glycyrrhiza glabra
• El-Saber Batiha, Gaber, et al. “Traditional Uses, Bioactive Chemical Constituents, and Pharmacological and Toxicological
Activities of Glycyrrhiza Glabra L. (Fabaceae).” Biomolecules, vol. 10, no. 3, 25 Feb. 2020, 10.3390/biom10030352.
• Thakur, Ajit Kumar, and Pooja Raj. “Pharmacological Perspective of Glycyrrhiza GlabraLinn.: A Mini-Review.” Journal of
Analytical & Pharmaceutical Research, vol. 5, no. 5, 4 Aug. 2017, 10.15406/japlr.2017.05.00156. Accessed 15 Nov. 2020.
• https://www.healthline.com/nutrition/licorice-root
5. Aloe barbadensis
• Surjushe, Amar, et al. “Aloe Vera: A Short Review.” Indian Journal of Dermatology, vol. 53, no. 4, 2008, p. 163, 10.4103/0019-
5154.44785.

• https://www.gardenia.net/plant/aloe-barbadensis-barbados-aloe
• https://www.ourhouseplants.com/plants/aloe
• https://www.finegardening.com/article/meet-the-aloe-vera-plant-aloe-barbadensis
6. Prunus serotina
• https://www.cabi.org/isc/datasheet/44360
• http://www.missouribotanicalgarden.org/PlantFinder/PlantFinderDetails.aspx?kempercode=a914
7. Vanilla planifolia
• https://www.missouribotanicalgarden.org/PlantFinder/PlantFinderDetails.aspx?taxonid=283438
• http://powo.science.kew.org/taxon/urn:lsid:ipni.org:names:262578-2#uses
• https://pfaf.org/user/Plant.aspx?LatinName=Vanilla+planifolia

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