GLYCOSIDES AND TANNINS

1. Cardioactive glycosides
 Glycosides are compounds that yield one or more 2. Anthraquinone glycosides (Anthracene)
sugars among the products of hydrolysis. -employed as stimulant cathartic
 Glycosides are condensation products of sugars a. Cascara sagrada
with various kinds or organic compounds with b. Frangula
added restriction that OH of the hemiacetal portion c. Aloe
of the carbon must participate in the condensation. d. Senna
 Chemically, are acetals in which the OH of the sugar e. Chrysarobin
is condensed with the OH of the nonsugar f. Rhubarb
components and the 2nd OH is condensed within the g. Danthron
sugar molecule itself to form an oxide. 3. Saponin glycosides (Sapogenin)
 Glycosides are SUGAR ETHERS. a. Glycyrrhiza or Licorice
b. Ginseng
2 COMPONENTS OF GLYCOSIDES c. Dioscorea
 Important characteristics of Saponin glycosides
A. AGLYCONE or GENIN a) Form colloidal solutions with water that
-NONSUGAR component foams upon shaking
-basis of classification b) Bitter acrid taste
-responsible for the therapeutic action c) Sternurotatory (irritating to the mucous
membrane)
B. GLYCONE d) Destroy RBC by hemolysis (toxic to cold-
-SUGAR component blooded animals (fish poison)
a) Beta D-glucose- most frequently occurring 4. Cyanophore/Cyanogenic glycosides (HCN)
sugar (formerly referred to as GLUCOSIDE) -widely employed as flavoring agents
 Both beta and alpha forms are possible but only the -anticancer claims (Laetrile/Vitamin B17-amygdalin
beta forms occur in plants. containing preparation)

5 CLASSIFICATIONS OF GLYCOSIDES

1. According to the identity of the sugar moiety

Ex: Glucoside-Glucose; Fructoside-Fructose  Common cyanophore glycosides

2. According to the complexity of the sugar moiety a) Derivatives of Mandelonitrile

Ex: Monosides, Biosides etc. (benzaldehyde-cyanohydrin)
Ex: Amygdalin (bitter almonds, kernels of apricots
3. According to the aglycone (feasible but intricate and other seeds of Rosaceae)
because of the large variety of aglycone)
Ex: Tannins, Sterols, Carotenoids, Anthocyanins b) Prunasin- Prunus serotina
c) Sambunigrin- Sambacus nigra
4. According to the therapeutic activity
Ex: Cardiotonics, Cathartics 5. Isothiocyanate glycosides (Isothiocyanates)
-from the seeds of cruciferous plants
a. Sinigrin (Black Mustard)
5. According to the chemical nature of the aglycone -hydrolyzed to form allylisothiocyanate
Ex: Anthraquinone, Saponins, Cyanophore (volatile mustard oil)
b. Sinalbin (White Mustard)
PROPERTIES OF GLYCOSIDES -hydrolyzed to form acrinyl isothiocyanate
(when pure) c. Gluconapin (Rape Seed)

1. Colorless or White  Isothiocyanate glycosides also known as

2. Optically active glucosinolates (represent a group of bound
3. Soluble in alcohol and dilute alcohol poisons like the cyanogenic glycosides).
 The S atom is conjugated with glucose as the S
FUNCTIONS OF GLYCOSIDES IN PLANTS glycoside.
 Characteristic constituents of the mustard family
1. Regulatory (Brassicaceae) as rapeseed, mustard, horseradish,
2. Sanitary broccoli, cabbage and turnips.
3. Protective  Feeding deterrent (insects) found to have
anticarcinogenic property.
CLASSIFICATION ACCORDING TO THE CHEMICAL
NATURE OF THE AGLYCONE
  Garlic possesses antihyperlipidemic and enhances
fibrinolytic activity and inhibits platelet
aggregation.
 (E) ajoene & (Z) ajoene formed from alicin
have antithrombotic property with the Z-
isomer being more bioactive.
6. Flavonol glycosides
-together with their algycones are termed as
flavonoids.
-occur as yellow pigments in higher plants
-best known flavonoid constituents
a) Rutin
b) Quercitrin
c) Citrus bioflavonoids (hesperidin,
hesperitin, diosmin, naringen)
-treatment of common colds
 Rutin and Hesperidin are referred to as
Vitamin P or Permeability Factors
(treatment for capillary bleeding)
7. Alcohol glycosides (Alcohol)
Ex: Salicin
-from the species of Salix and Populus
-willow and popular barks yield salicin
-Principal Sources
 Salix purpurea and Salix fragilis
-hydrolize into D-glucose and saligenin
(salicyl alcohol)
-has antirrheumatic properties
8. Aldehyde glycosides (Aldehyde)
a) Vanilla (vanillin develop during the curing
process)
 Vanillin is semisynthetically prepared
from:
-Coniferin (from pine trees)
-Eugenol (from clove oil)
-Lignin a by-product of the pulp industry
(from where most of vanillin in
commerce is made)
 Vanillin is used as flavoring agent.
9. Lactone glycosides (Coumarin)
a. Skimmin (Japanese Star Anise)
b. Aesculin (Horse Chestnut Tree)
c. Daphnin (Ash Bark)
d. Scopolin (Belladonna)
e. Limettin (Citrus Trees)
Uses of Coumarin and Coumarin Derivatives
a. Flavoring agent (pharmaceutically)
b. Anticoagulant (Dicumarol/Bishydroxycoumarin)
c. Antispasmodic
d. Uterine derivatives
e. For dermatologic purposes
(Cantharidin and Methoxsalen)
f. Anthelmintic (Santonin)
10. Phenol glycosides
a. Arbutin (Uva ursi, Chimapila)
b. Hespiridin (Citrus fruits)
c. Phloridzin (Rootbark of Rosaceous plant)
d. Baptisin (Baptisia, Iridin)
TANNINS
 Tannins are complex substances usually occur as
mixtures of polyphenols that are difficult to
separate because they do not crystallize.
 Tannins are also referred to as Tannin extracts.
 Tannins are usually localized in specific plant parts
as stems, leaves, fruits and barks.
3 CHEMICAL CLASSES OF TANNINS
(based on the identity of the phenolic nuclei)
A. Hydrolyzable Tannins / Pyrogallol Tannins
Ex: Gallitannins, Ellagitannins
-readily hydrolyze to yield phenolic acids (gallic
acid and related polyhydric compounds) and sugar
(glucose units)
-gives blue/black color with FeCl3 reagent
B. Nonhydrolyzable Tannins / Condensed Tannins
/ Catechol Tannins
Ex: Proanthocyanidins
-contain only phenolic nuclei but frequently are
linked to carbohydrates or proteins.
-(+) hydrolytic agents is polymerized producing
red-colored compounds (Phlobaphenes)
-gives blue to green color with FeCl3 reagent
C. Pseudotannins
Ex: Gallic acid, Catechins, Chlorogenic acid
-Both classes of tannins are widely distributed.
-Both are present although one type tends to
predominate.
Uses of Protein Precipitating Property of Tannins
a) Vegetable tanning
b) Poison antidote
c) Detection of gelatin, protein, alkaloids
PROPERTIES OF TANNINS
a. Non-crystallizable
b. Form colloidal solution with water possessing acid
reaction with sharp puckering taste
c. Precipitate solutions of gelatin and alkaloids
d. Form dark blue/greenish black soluble compounds
with Fe salts
e. Forms deep red color with K ferricyanate and
ammonia
f. Precipitated by salts of Cu, Pb, Tin, Strong aqueous K
dichromate
USES OF TANNINS
a. Astringent (GIT and skin abrasions)
b. Treatment of burns
c. Vegetable tanning (convert animal hides to leather)
“Bloom leather”-hydrolyzable tannin
“Tanners Red Leather”-nonhydrolyzable tannin
d. Manufacture of inks
e. Reagent in the detection of gelatin, proteins and
alkaloids.
f. Antidote for alkaloid poisoning
g. May have potential value as
cytotoxic/antineoplastic agents