3.3.

Glycosides

By: Betelhem Sirak (B.Pharm, MSc in

Pharmacognosy) 1
Glycoside
• Glycosides or sugar ethers, are a complex grouping which
can be broken down to yield one or more sugars (glycone)
parts and non-sugar parts (aglycone or genin).
• The term glycoside may refer to any natural product which
can potentially occur bound to sugars.
• It is important to note that glycosides are not a major
classification of phytochemicals as are alkaloids,
carbohydrates, phenols and terpenoids.

2
Glycoside…
• Pharmacological activity is due to the aglycone
• The sugar part influences pharmacokinetic
Sugar Non-
glycosidic Glycoside
(glycone bond
sugar
) (aglycone
)
Hydrolysi
s

Sugar Non-
(glycon + sugar
e) (aglycone)

3
 General properties of glycosides

Distribution

• Glycosides are mostly found in plants and microorganisms,

however, very few important glycosides are obtained from animals.
• Glycosides could be found in any part of plants.
• Glycosides are generally present in vacuoles of cells (intracellular).
• The amount of glycosides may vary in the same plant due to
seasonal and climatic conditions and also depending on the growth 4
 General properties of glycosides…
Chemical properties
• D-glucose is the most common sugar that occurs in glycosides.
• In most glycosides the sugar moiety is a true sugar; however, there are several
glycosides in which the sugar moiety is not a true sugar but rather a sugar
derivative such as uronic acids.
• In glycosides, the aglycone is attached to the C1 of sugars.
• As a result, they are non-reducing.
• By and large, glycosides glycosidic linkages in natural glycosides have the β-
form.
• More than one sugar molecule may be present in glycosides.
• The sugar molecules may be attached to the aglycone at different points or
• They may be attached to each other as disaccharides, trisaccharides
• Most glycosides are hydrolysable by boiling with acids.
5
 General properties of glycosides…
Chemical properties
• Almost all glycosides are accompanied by enzymes which can hydrolyze
them.
• The enzymes can be found in different cells of the plant or in the same cells
but being membrane bound.
• During injury to the tissue, germination or other physiological activity, the
enzymes may come with the glycosides, and the hydrolysis of glycosides
takes place.
Physical properties
• Most glycosides are crystalline compounds.
• The higher the sugar content, the less soluble are glycosides in organic
solvent.
• Glycosides form levorotaroy solutions in water and alcohol
• Most glycosides have bitter taste. 6
 Functions of glycosides in plants
• In plants, glycosides may be involved in regulatory(growth),
sanitary (detoxification) or protective activities.
• They may be used to
• Modify solubility of compounds using monosaccharide
• Stabilize some liable compounds.
• Store some organic compounds (harmful products such as
phenol).
• Some glycosides also are used as sugar reserves (Source of
energy), for example, for germinating seeds.
• Some colored flavonoids such as anthocyanins, which are found
in flowers may serve as pollinators. 7
 Pharmacological activity of glycosides
• Pharmacological activity of glycosides is intimately associated with the aglycone.

• The sugar part influences stability and solubility and ultimaetly pharmacokinetic
phenomena (absorption and distribution ) of the drug in the body.

• Some glycosides are not active in the glycosidic form but on hydrolysis, they yield
active aglycones.

• Such drugs are known as “ reactionary drugs”.

8
Glycosidic linkages
I. O-Glycosides
• The sugar is condensed with alcoholic or phenolic hydroxyl
group, or carboxylic group of the aglycone.
• O-glycosides could be regarded as sugar ethers.
• O-glycosides are the most abundant glycosides.
• They can easily be hydrolyzed boiling in mineral acids.

9
Glycosidic linkages…
II. S-glycosides:
• In these glycosides the sugar is condensed with a
sulfahydral (thiol) group of the aglycone.
• Natural S-glycosides are very few.
• They can easily be hydrolyzed by boiling in mineral acids.

10
Glycosidic linkages…
III. N-glycosides:
• In these glycosides the sugar is condensed with an amino
(-NH2 or –NH) group of the aglycone. E.g. nucleosides,
DNA, RNA.
• They can easily be hydroyzed by boiling in mineral acids.

11
Glycosidic linkages…
IV. C-glycosides:
• In these glycosides the sugar is condensed directly to a carbon
atom.
• They are highly resistant to acid hydrolysis.
• They can only be hydrolyzed oxdatively.

12
Primary and secondary glycosides

• Primary glycosides are those which have an oligosaccharide

unit and are extracted intact, without losing any sugar unit.

• Extraction and drying processes can result in the removal of 1 or

two sugars from primary glycosides giving rise to a new
glycoside with less number of sugar units.
• These types of glycosides are referred to as secondary glycosides.
13
 Classification of glycosides
• The classification of glycosides is highly challenging and often not
completely successful.
• For practical purposes, however, the following classification approach
has been used
1. Based on the sugar part
• Example
• Glucosides are those glycosides which have only glucose as their sugar part.
• E.g. Sennoside.
• Rhamnosides are those glycosides which have only rhamnose as their sugar part.
• E.g. frangullin.
• Rhamnoglucosides are those glycosides which have only rhamnose and glucose
as their sugar parts.
• E.g. Rutin
14
 Classification of glycosides…
2. Based on pharmacological activity
• Cardiac glycosides are those which have pharmacological effects on the
heart.

3. Based on the chemical nature of the aglycone

• Accordingly we have the following types of glycosides.
• Anthraquinone, Saponin, Flavonoids, Terpene, Alcohol, Simple
phenolic glycosides, Cyanogenetic (cyanophoric) glycosides,
Aldehyde glycosides, Isothiocyanate glycosides, Ester glycosides,
Lactone glycosides and Amino glycosides
15
Nomenclature of glycosides
1. Trivial names
• Have an “in” ending and
• The name indicates the source of the glycolyside.
• E.g. Digitoxin from digitalis
• Salicin from salix and
• Prunasin from pronus
16
 Nomenclature of glycosides…
Systemic names
• Are usually formed by replacing the “ ose” suffix of the parent sugar
with “oside”
• The anomeric prefix (α or β) and the configuration prefix (D or L)
immediately precede the sugar stem name, and the chemical name of
the aglycone precedes the name of the sugar.
• E.g. the systematic name for salicin is:
• O-hydroxymethylphenyl β-D-glucopyranoside 17
 Medicinally and
Pharmaceutically Important
Glycosides

18
1. Anthraquinone (anthracene) glycosides
• Anthraquinine glycosides are those glycosides which have
anthraquinone derivative aglycones.
• They are also called anthracene glycosides but anthracene does
not occur naturally. O

anthracene
O

Anthraquinone

• They are mostly O- glycosides but some C-glycosides also occur.

• The anthraquinone aglycones can exist in different oxidation
state.
19
1. Anthraquinone (anthracene) glycosides…
O OH

4H

O Anthranol
O
Anthrone
Anthraquinone -2H
2H
O

OH
Oxanthrone

O
Dianthrone 20
1. Anthraquinone (anthracene) glycosides…
• Example:
OH O OH

H OH
H
O
HO
HO O O OH CH2OH
OH HO
H
H H
O
OH
CH2OH
O OH
HO
Aloe-emodin 8-glucoside
(an O-glycoside) Barbaloin
(a C-glycoside)

21
 1. Anthraquinone (anthracene) glycosides…
• Pharmaceutical activity/therapeutic uses
• Stimulant cathartics
• Enhance motility of large intestine, leading to increased volume and
pressure that stimulates colonic motility.
• used commonly by patients with IBS who have severe constipation,
• Remarks:
• Glycosides of anthranols and anthrones elicit a more drastic action
than do the corresponding anthraquinone glycosides.
• The glycosides are hydrolyzed by the enzymes of the microflora to
the pharmacologically active free aglycones.
• They act on the large bowel.
• They increase the strength of peristalic contractions but not the
frequency. At larger doses, they cause colic pain.
• They are habit forming
• They must not be prescribed for more than 15 days. 22
1. Anthraquinone (anthracene) glycosides…
• Historically: Rhubarb, Senna, Aloes and Cascara were all used as
purgative drugs.
• Monocotyledons: Only Liliaceae.
• Most commonly C-glycoside: barbaloin.

• Dicotyledons: Rubiaceae, Leguminosae, Polygonaceae,

Rhamnaceae, Ericaceae, Euphorbiaceae, Lythraceae, Saxifragaceae,
Scrophulariaceae and Verbenacacea.
• Also in certain fungi and lichen.

23
• Chemical tests for anthraquinone glycosides
• Borntrager’s test
• This test requires free anthraquinone-type aglycones.
• Anthraquinone-type aglycones produce pink, red or violet
color with NH4OH solution or NaHCO3 solution.
• Glycosides and reduced anthraquinone aglycones (anthrones,
anthranols, oxanthrones and dianthrones) do not give positive
result in this test.
• Schonteten’s test (Florence test for anthranols)
• Anthranols produce a strong green florescence in borax or
other alakli solutions

24
Crud drug Botanical source Active constituents Use

Senna Dried leaflets of cassia acutifolia or C. Sennosides A and B Stimulant

angustifolia (fam. Fabacieae) Cathartics

Rhubarb Dried rhizomes and roots of Rheum Sennosides, chrysophanol Laxative

officinale or other spices of Rheum glycosides, aloe-emidin
except R. raponticum (fam. glycosides and emodin
Polygonaceae) glycosides
Cascara Dried bark of Rhumunus purshina (fam. O-glycosides (10-20%), C- Laxative
Rhamnaceae) glycosides (80-90%) and some
free anthraquinones: e.g.
cascarosides
Aloe Dried juice of the leaves of various spp Two fractions: an anthraquinone Purgative
of Aloe like Aloe barbadensis (fam. fraction called “ aloin” and
Liliaceae) resins. Barbaloin is the major
const. 25
Senna

26
Cascara

27
Rhubarb

28
Aloe

29
2. Saponin glycosides
• Saponin glycosides have pentacyclic triterpinoid derivative or
steroidal (cyclopentanoperhydrophenanthrene) derivative as their
aglycone part.
• Saponin aglycones are commonly referred to as sapogenins.
• Based on the sapogenin unit, saponin glycosides are classified in to
pentacyclic triterpinoid glycosides and steroidal glycosides.

Pentacyclic skeleton steroidal skeleton

30
2. Saponin glycosides…
• General physical properties of saponin glycosides
• Produce foam (froth) in aqueous solutions.
• Are hemolytic to red blood cells.
• General chemical and physical properties of saponin glycosides
• In plants, steroidal sapogenins are the derivatives of pentacyclic
sapogenins (triterpenes).
• They are produced by removal of fragments and rearrangement reactions
• All saponin glycosides have β-O- glycosidic linkages at C-3.
• some may have O- or C- glycosidic linkage at other sites
• They form a 1:1 addition complex (precipitate) with cholesterol,
especially in the presence of Ca2+.
• This is the basis for their hemolytic activity. 31
2. Saponin glycosides…
• Have long been used in many parts of the world for their detergent
properties
• E.g. In South America bark of Quillia saponaria
• In Europe root of saponoria officinalis
• Foam in aqueous solution by forming colloidal solution, which
decreases surface tension
• Causes haemolysis or red blood cells hence toxic if injected to blood
stream especially to cold-blooded animals, e.g. frogs

32
2. Saponin glycosides…
• Pharmaceutical application of saponin glycosides
• Steroidal glycosides due to their structural similarity, they are used as
starting material for the semi-synthesis of steroid based drugs such as
• Sex hormones (for replacement therapy and preparations of oral contraceptives).
• Cortisones (steroidal anti-inflammatory drugs),
• Diuretic steroids (e.g. spironolactones),
• Cardiac glycosides and Vitamin D
• Example
• In 1934, only 20mg progestrone was isolated from 625 kg of ovaries
obtained from 50,000 cows.
• In 1944, following the procedure for the coversion of diosgenin to
progestrone, discovered by Russell Marker, progestrone was semi- 33
2. Saponin glycosides…

Diosgenin Progesterone

34
2. Saponin glycosides…
1. Steroidal saponins
• Less widely distributed in nature
• Common in: Dioscoraceae (e.g. discoria spp), Amaryllidaceae (e.g.Agavae spp)
Liliaceae (e.g. yucca and trillium spp)
• Useful starting materials for the synthesis of steroidal drugs
• Sterols (steroidal alcohols) such as β-sitosterol and stigmasterol
are employed as starting material for the production of steroidal
drugs.
• Note: continuous effort is being made to discover plants with high yield of
steroidal glycosides to ensure their regular supply to the drug industries.
35
2. Saponin glycosides…
• Botanical sources of steroidal glycosides:

Crude drug Botanical sources Steroidal saponin

Diaoscoria Dried rizomes of several spp. Of Diaoscoria Dioscin (diosgenin)

(yam) such as D. macrostachya (fam.
Diaoscoreaceaea)
Sisal Agave sisalana (fam. Agavaceae) hecogenin
Fenugreek Seeds of Trigonella feonum-graecum (fam. Dioscin (diosgenin)
seeds Fabaceae)
Soya bean The seeds of glycine max (fam.Fabaceae) β-sitosterol and
sterols stigmasterol
36
 2. Saponin glycosides…
2. Triterpenoidal saponins
• Abundant in many dicotyledonous families:
• Caryophyllaceae, Sapindaceae, Polygolaceae
• Uses
• Foaming beer
• Cleaning industrial equipment and fine fabrics
• Powerful emulsifier of certain resin, fats and fixed oils
• Antifungal and antibacterial agents,
• Lowering of blood cholesterol
• Inhibition of cancer cell growth 37
2. Saponin glycosides…
i. Licorice
• Dried unpeeled roots and rhizomes of Glycyrrhiza glabra (Fabaceae)
• Contains a saponin glycoside called Glycyrrhizin
• Uses:
• As sweetening agent
• Treatment of rheumatoid arthritis
• Anti-inflammatory
• Potential for the treatment of peptic ulcer

38
2. Saponin glycosides…
ii. Phytolacca dodecandra
• Commonly known as “endod” in Amharic
• Contain a glycoside called Lemmatoxin

39
3. Cardiac Glycosides
• The aglycones of these glycosides have a steroidal nucleus
with a lactone functional group.
• According to the size of the lactone ring, cardiac glycosides
are classified into two groups:
• Cardenolides, which have 5-membered lactone (ɤ-lactone)
• Bufadienolides, which have 6-membered lactone (α-
pyrone)

40
3. Cardiac Glycosides…
• Steroids in nature exerts powerful action on the cardiac
muscle.
• Plant glycosides with specific action on heart
• Historical use:
• To assassinate people, arrow poisons
• Historical sources: South American toad skins, African plant extracts
• Modern use:
• To treat congestive heart failure (dropsy)
• Aglycone structure important for activity
• As a glycoside the sugar moiety is attached to the #3 position
of the steroid nucleus 41
3. Cardiac Glycosides…
• General Formula
• The R group at the 17-position
defines the class of cardiac
glycoside.
• Cardinolides are obtained
almost entirely from plants.
• Most bufadienolides are
obtained from frogs
(Bufonidae) and very few come
from plants.
42
3. Cardiac Glycosides…
• 2ndry glycosides are very common in the extraction of cardiac
glycosides.
• If drying is not carried out with precaution, β-glycosidase removes the
terminal glucose in many primary glycosides.
• Sugars occurring in cardiac glycosides
• The glycone part is almost always found β substituted at position 3.
• The sugar moiety could be a monosacharide but often an oligosacharides
(2-4) units.
• The sugars most commonly used include L- rhamnose, D-glucose, D-
digitoxose, D- digitalose, D-digginose, D-sarmentose, L- vallarose, and
D-fructose
43
3. Cardiac Glycosides…
• Pharmacological activity and therapeutic uses
• As their name implies cardiac glycosides, have specific and strong action on
the muscle of the heart.
• Cardenolides are commonly used for treatment.
• The bufadionilides tend to be highly toxic.
• They increase the strength of the contraction of the heart and thus used for cardiac
insufficiency and congestive heart failure (dropsy).
• They increase cardiac out put and decrease heart rate and heart volume.
• In addition, the improved circulation increases renal secretion which relives
edema.
• Their activity is due to their aglycone.
• Both the glycosides and the free aglycone show more or less equal activity.
• However, the sugar units greatly influence absorption, on set of action and half44
 3. Cardiac Glycosides…
Crude drug Botanical source Important cardiac
glycosides isolated
Digitalis Dried leaves of (Digitalis purpurea Digitoxin, gitoxin, and
(foxglove) (Scrophulariaceae) gitaloxin and other nearly 30
glycosides.
Grecian foxglove Dried leaves of (Digitalis lanta Lanatosides A-E, digoxin
(Scrophulariaceae) and other nearly 65
glycosides.
Strophanthus Dried ripe seed of Strophanthus kombe K-strophanthoside
and S. hispidus (Apocyanaceae)
Squill (squill The cut and dried, fleshy inner scales of Scillaren A (a bufadienolide)
bulb) the bulb of the white variety of Urginea
maritima 45
3. Cardiac Glycosides…
• Sources
• Scrophulariaceae
• Digitalis purpurea leaves (foxglove)
• Digitalis lanata leaves – white flowers
• Apocyanaceae
• Strophanthus vine seeds – Africa
• Liliceae
• Urginea bulbs (squill) – Europe, India
• Convallaria leaves (lily of the valley) –
• also produces a volatile oil perfume
46
4. Flavonoid Glycosides
• Flavonoids are glycosides in which the aglycone has C6-C3-C6 nucleus.
• They are usually substituted by hydroxyl groups.
• They are responsible for the color of flowers, fruits and sometimes
leaves.
• Flavonoidal compounds occur mainly as O-glycosides, sometimes as
C-glycosides and free aglycones.
• The major structural categories are flavones, flavanones, flavonols,
anthocyanidins, catechins (flavan-3-ols or flavan-3,4-diols).
• Can get several forms of flavonoids depending on nuclei
• Often yellow (flavus Latin – yellow) 47
4. Flavonoid Glycosides…

48
4. Flavonoid Glycosides… O

O
O

O
Isoflavanoid
O
Flavanone
Flavone

O
O
O

OH

OH
O

Flavonols Catechin (Flavan -3-ol)

Anthocyanidin
49
4. Flavonoid Glycosides…
• Many have yellow color
• Anthocyanins have red, blue or purple color
• Most absorb in the UV region
• Exhibit various pharmacological activities including anti-
inflammatory (and analgesic) properties
• Anti-allergic effects
• Antithrombotic, vasoprotective properties
• Antioxidant
• Anti-inflammatory

50
4. Flavonoid Glycosides…
• Some medicinally important flavonoids
• Rutin (Vitamin P)
• Used as for the treatment of capillary bleeding and
increased capillary fragility
• From Fagopyrum esculentum (buckwheat)

51
4. Flavonoid Glycosides…
• Silybin
• Silybin is the major active compound isolated from
silymarin, a hepato protective Flavonoidal fraction
obtained from Silybum mariamum (Astraceae) (Milk
Thistle, St. Mary Thistle) .
• Silybin and also silymarin are used for wide range of liver
O OH

OH
problems.
O
OH
O
O
O O
OH CH3
OH
OH OH
O
OH
O OH OH
OH O
Silybin 52
Silymarin
4. Flavonoid Glycosides…
• Properties of flavonoid glycosides
• water and alcohol soluble
• give brightly coloured solutions crystallise easily
• may give colour reactions eg
• MgCl2 -> violet -> orange
• alkali KOH -> orange
• easy to detect

53
5. Isothiocynate Glycosides
• These are glycosides based on the following general formula:
N O SO3- K+

R C
S C6H11O6

• The basic structure of glucosinolates comprises a glucose residue, a

sulfate group found as potassium salt and a variable aglycone.
• They are S-glycosides widely distributed in family Cruciferae and
Brassicaceae
• Since glucosinolates are ionic compounds they can be separated on ion
exchange resin.
54
5. Isothiocynate Glycosides…

• When the tissues of glucosinolates-containing plants are

bruised, the glucosinolates are hydrolyzed by a
thioglucosidase commonly known as myrosinase (myrosin)
which is always found in this type of plants.
• In all cases the free aglycone is unstable and rearranges.
• If the pH is neutral, the product will be a strong-smelling volatile
isothiocyanate.

55
5. Isothiocynate Glycosides…
• A notable example of glucosinolates is sinigirin, which occurs in the
seeds of black mustard (Brsssica nigra. Brassicaceae) or Indian
mustard (B.juncea: Brassicaceae)
• Siningrin is allylglucosinolate and up on hydrolysis by myrosinase,
it produces allyl isothicynate.
• Allyl isothiocyanate is strong-smelling volatile compound
• Responsible for the astringent odor and flavor of mustard
• In order to see the effect of hydrolysis, mustard seeds have to be soaked in
water for few days.

56
5. Isothiocynate Glycosides…
• Sinigrin
• Occurs in the seeds of black mustard (Brassica nigra: Brassicaceae) or
Indian mustard (B. juncea: Brassicaceae)
• Uses of allyl isothiocyanate
• as condiment
• is used as counter irritant (rubefacient)
• used in the form of plasters
N O SO3- K+
H2O + KHSO3 + C6H12O6
CH2=CHCH2 C H2C=CHCH2-N=C=S
S C6H11O6 Myrosinase
Ally isothiocyanate
Sinigrin
(allylglucosinolate)
57
 R CN
6. Cyanogenic glycosides
R'' O sugar
• Cyanogenic glycosides are glycosides which produce hydrocyanic acid
(HCN) upon completed hydrolysis
• All cyanogenic glycosides are glycosides of 2-hydroxylnitriles.
• Hydrolysis of cyanogenic glycosides occurs when there is injury of cells that
leads to mixing of hydrolyzing enzymes and the glycosides.
• In cyanogenic glycosides, the sugar (most of the time glucose) is hydrolyzed
by more or less specific enzyme.
• The resulting hydroxynitrile lyase to produce a carbonyl compound (an
aldehyde or a ketone) and HCN.
• Cyanogenic glycosides are important plant toxins.
• The glycosides themselves are not toxic however, the hydolysis product, HCN is so.
58
6. Cyanogenic glycosides…
• Occurrence and distribution of cyanogenic glycosides
• Over 2500 plant species are potentially cyanogenic.
• Some these are edible, even stable foods.
• Cyanogenic glycosides are very common in the family Rosaceae, Fabaceae,
poaceae etc
• Examples of plants containing cyanogenetic glycosides:
• Apricot, Bitter almond, Peach, Pear , Apple, Plum, Wild cherry(bark)
• Cassava (Manihot esculenta: Euohorbaceae)
• Linseed (Linom usitatissimum: Linaceae)
• A notable example of cyanogenetic glycosides is amygdalin which
occurs in a number of prunus spp.
• The hydrolysis of amygdalin is results in benzaldehayde 59
7. Coumarin glycosides
• These are glycosides which have coumarin based aglycone.
O O
5 4
6 3

7
O 2 O
8

• In the plant, coumarin is believed to exist in a glycoside form but upon

injury to the plant, it losses the sugar part

60
 O O

O OH O

7. Coumarin glycosides… O
OH

O OH
Warf arin O
Dicoumarol
• Pharmacological activity
• Some coumarin derivatives have anticoagulant activity
• Used as oral anticoagulant agents
• Most of the naturally occurring coumarins lack anticoagulant activity but they
are converted to derivatives with such acivity, by microbial action (e.g.
Dicoumarol).
• The structural requirements for a coumarin derivatives to exihibit anticoagulant
activity are the 4-hydroxy group and a substituent at C3.
• Dicoumarol is very potent anticoagulant which can not be used for treatment
purpose.
• However, it was used as a lead compond for the synthesis of coumarin based oral
antcoagulants such as warfarin. 61
7. Coumarin glycosides…
• Historical background:
• In the 1920’s, the use of Sweet clover (Melilotus alba and M.officinalis
(Fabaceae ) as hay crop was wide spread in the northern USA and Canada.
• All Melilotus spp. Contain melilotoside (a glucoside of 2-hydroxycinnamic
acid ). This glycoside can easily loss its sugar and then lactonize to form
coumarin.
• When sweet clover is put as hey, it is easily contaminated with molds
particularly, when conditions are wet at cutting or curing. Molds such as
Penicillium nigricuans, P.jinsi and Aspergillus metablize 2-hydroxycinnamic
acid in to dicoumarol
• A series of wet summers led to an epidemic of bleeding in cattle and it was
found out that it was due to dicoumarol.
• Remark: important grass can potentially be toxic to cattle, due to
anticoagulant coumarins 62
8. Simplephenolic glycosides
• Alcohol glycosides
• These are glycosides which give an alcoholic aglycone up to hydrolysis.
• A notable example is salicin which is isolated from willow bark (Salix
fragilis or S.purpurea: Solanaceae).
• Traditionally willow bark has been and still is used
• For fever and flu-like symptoms
• As an analgesic (for headaches and toothaches)
• Orally or topically for symptomatic relief of minor pains of the joint and rheumatoid
disorders.
CH2OH CH2OH COOH CH2OH O

O glc OH oxidation OH O C CH3

in the
body

Aspirin
Salicin Salicyl Salicylic 63