Glycosides

Part 2
Summary
The cyclic form of glucose is a six-membered ring, with an intramolecular
hemiacetal formed by attack of the hydroxl on carbon #5 to the aldehyde
carbon (carbon #1, also called the anomeric carbon in carbohydrate
terminology). The cyclic form of glucose is called glucopyranose
deoxy-sugars
• These deoxy-sugars frequently contain a number of additional
modifications, including
• further deoxygenation (especially at the 6-position,but also
frequently at the C-3 position),
•

Galactose fucose
 Examples
• Deoxyribose, or 2-deoxy-D-ribose, a constituent of DNA
• Fucose, or 6-deoxy-L-galactose, main component of
brown algae, and present in N-linked glycans
• Rhamnose, or 6-deoxy-L-mannose, present in plant
glycosides: is a naturally occurring deoxy sugar. It can
be classified as either a methyl-pentose or a 6-deoxy-
hexose

manose Rhamanose
Examples
 Arbutin
• Arbutin is a glycoside; a glycosylated
hydroquinone extracted from the bearberry plant
among many other medicinal plants, primarily in
the family Ericaceae. Applied topically, it inhibits
tyrosinase and thus prevents the formation of
melanin.

4- Hydroxyphenyl-alpha-D-glucopyranoside.
Alpha Arbutin 2%
apha vs. beta new slide
Alpha-arbutin and deoxyarbutin are synthetic forms of arbutin,
while beta-arbutin is the plant-derived form of arbutin. “Both
forms of arbutin suppress melanin production, but studies have
shown that alpha-arbutin is more stable and is estimated to
be more than 10 times stronger than beta-arbutine
 Salicin
• Salicin is an alcoholic β-glucoside. Salicin is
produced in (and named after) willow (Salix)
bark. It is a biosynthetic precursor to
salicylaldehyde.

2-(Hydroxymethyl)phenyl β-D-glucopyranoside
Rhein-8-glucoside
• Rhein-8-glucoside is an anthraquinone glycoside
that has been found in rhubarb. It increases the rate
of sennoside A

Rhein 8-O-β-D-Glucopyranoside)
 Nomenclature: ‫توحيد االسم‬

anthraquinone

Rhein 8-O-β-D-Glucopyranoside)

1, 8-dihydroxyanthraquinone-3-carboxylic 1-hydroxyanthraquinone-3-carboxylic
acid) = Rhein acid) 8-O-β-D-Glucopyranoside
 sennosides
Sennosides are used to treat constipation. They may also be used to clean out the
intestines before a bowel examination/surgery.
 Barbaloin
*Barbaloin is C-glucoside of aloe.

*Aloin, also known as barbaloin, is a bitter, yellow-brown colored

compound noted in the exudate of at least 68 Aloe species at levels
from 0.1 to 6.6%.

* Barbaloin is the major anthraquinone compound that is isolated from

the leaf exudates of Aloe vera and is often used as a bittering agent in
alcoholic beverages

‫(لالطالع‬10–glucopyranosyl–1,8–dihydroxy–3–(hydroxymethyl)–9(10H)–anthraquinone:
aloin A)
 Digoxin
• Digoxin belongs to the class of medicines called
digitalis glycosides. It is used to improve the strength
and efficiency of the heart, or to control the rate and
rhythm of the heartbeat. This leads to better blood
circulation and reduced swelling of the hands and
ankles in patients with heart problems
 Lanatoside
• Lanatoside C (or isolanid) is a cardiac glycoside, a
type of drug that can be used in the treatment of
heart failure and cardiac arrhythmia
 Lanatoside A and B and C

While lanatosides A, B, and C have similar mechanisms of action and

pharmacological effects, they may differ in potency, pharmacokinetics, and other
specific properties. These differences can influence their clinical use and potential
side effects.
base hydrolysis
 Myrosin enzyme
• A member of the glycoside hydrolase family, myrosinase
possesses several similarities with the more O-
glycosidases.

• However, myrosinase is the only known enzyme found in

nature that can cleave a thio-linked glucose.
• Its known biological function is to catalyze the hydrolysis
of a class of compounds called glucosinolates.

Glucosinolate structure;
Hydrolysis using myrosin
enzyme
 ‫لالطالع انزيمات‬
• Emulsin, also known as β-glucosidase, is an enzyme that
catalyzes the hydrolysis of glycosidic bonds in various
substances, particularly glucosides. It belongs to the class of
hydrolases, which are enzymes that catalyze the cleavage of
chemical bonds through the addition of water molecules.

• Emulsin specifically acts on β-glycosidic bonds, breaking them

down into their constituent parts.
• For example, it can catalyze the hydrolysis of amygdalin, a
cyanogenic glycoside found in bitter almonds, into glucose,
benzaldehyde, and hydrogen cyanide. This reaction is what
causes bitter almonds to release cyanide when they are chewed
or crushed.
Hydrogen cyanide formation as a result of
hydrolysis of amygdalin.