GLYCOSIDES − Aldehyde group

− Phenol group
− compounds that yield one or more sugars among the product
of hydrolysis CARDIAC GLYCOSIDES
− A glycoside is any molecule in which a sugar group is bonded − Related to steroids, CPPP nucleus
through its anomeric carbon to another group via glycosidic − Sugar component is attached on the 3 position of the CPPP
bond. nucleus
o Cyclo, pentano, perhydro, phenanthrene
In aqueous solution hexoses and pentoses will cyclize, forming − 2 aglycone
alpha (a) and beta (B) forms o (1) cardenolides
o (2) bufadienolides (discovered from BUFALIN
− Trivial names have an “in” ending and the names indicate the isolated from the skin of toad)
source of glycosides
− Examples: [Link]-BURCHARD TEST
o digitoxin — from Digitalis − Tests the cardenolides/ bufadienolides
o Salicin from Salix
o Prunasin from Prunus [Link] REACTION
− Tests the presence of the lactone ring
− Systematic Names are usually formed by replacing the “ose” − Detect the presence of cardiac glycosides
suffix of the parent sugar with “oside”. The anomeric prefix (a-
or b- )and the configurational prefix (D or L) immediately [Link]-KILIANI
precede the sugar stem name, and the chemical name of the − 2-deoxy sugars
aglycone precedes the name of sugar.
− Example: Salicin – o – hydroxy – methylphenol B-D-
glycopyranoside CARDIAC GLYCOSIDES: ACTION
− The most frequently occurring sugar is B-D- glucose, although − Inotropic effect – the ability to increase the force of systolic
rhamnose, digitoxose, cymarose and other sugars are contraction
o Can increase bp
component of glycosides
− Depletion of Potassium ions increases Digoxin Toxicity
− Glucoside – when the sugar formed is glucose
− Glycoside – when other sugar other than glucose is produced.
[Link] (without arrythmia)
− AN ARRYTHMOGENIC
GLYCOSIDES: COMPONENTS
− SOURCES
− Aglycone, aglycon, or genin — non sugar component of
o Foxglove (D. Purpurea)
glycosides
o Grecian foxglove (D. lanata)
− Glycone — sugar component
SCROPHULARIACEAE (Active Glycosides)
GLYCOSIDES: IMPORTANCE
DIGITALIS PURPUREA DIGITALIS LANATA
− Involved in its regulatory, protective and sanitary functions of
Digitoxin Digoxin
plants
Gitaloxin Desacetyl Lanatoside
− Therapeutic agents Gitoxin (deslanoside)

*Digitoxin past DOC for CHF but now is Digoxin

GLYCOSIDES: OCCURRENCE
*Shorter Half life, shorter duration of action
− Widely distributed in the plant kingdom
o fruits, Seeds, Barks, Leaves *Digoxin and Digitoxin: has narrow therapeutic index/window
− Animals (relatively rare) *0.5-1.5 ng/mL
*Digoxin – less protein binding

CLASSIFICATION OF GLYCOSIDES BASED ON GLYCOSIDIC LINKAGE CARDIAC GLYCOSIDES: DIGOXIN

1. O-glycosides — phenol or OH group
2. N-glycoside — N of amino group (NH) − More commonly used
3. S-glycosides — S of thiol group (SH) − It is polar because of the —OH group in the structure
4. C-glycosides—on C atom − Easily eliminated therefore, short acting.
o Pigeon — used in the bioassay (potency)
o Antidote: Digoxin Immune fab
CLASSIFICATION OF GLYCOSIDES BASED ON THE CHEMICAL − Inotropic agent
NATURE OF THE AGLYCONE GROUP
CARDIAC GLYCOSIDES: DIGITOXIN
− Cardioactive Steroid group − Lipophilic
− Anthraquinone group − Longer half life
− Saponin group − Before it is the drug of choice for CHF but now, it used in the
− Cyanophore group management of arrhythmia, atrial fibrillations
− Glucosinolate or Isothiocyanate group − Deslanoside — It is used for rapid digitalization
− Flavonol group
− Alcohol group
[Link] ANTHRAQUINONE GLYCOSIDES
− AKA: Lily of the Valley − related to anthracene
− Liliaceae − Upon hydrolysis yield syne that are di-, tri-, or
− From Convallaria Majalis tetrahydroxyanthraquinones or modification of these
− Liliaceae compounds.
− CONVALLOTOXIN o Example. Frangulin A, which hydrolyze to emodin(1,6,8-
o active component trihydroxy3- methylanthraguinone) and rhamnose.
o Not recommended o Penicillium islandicum — species that produce several
anthraquinone glycosides.
[Link]
− AKA: Black Indian hemp, Dog Bane − anthranols are converted upon oxidation into anthraquinones.
− From Apocynum cannabinum − Schonteten’s test → is often used for anthranols
− CYMARIN – active cardiac glycoside − Anthranolsand anthrones are the main constituents of
APOCYANACEAE chrysarobin, a mixture of substances

4. ADONIS ANTHRAQUINONE GLYCOSIDES: USE

− Stimulant cathartics
− AKA: Pheasant’s Eye
− exert their action by increasing the tone of the smooth muscle
− From Adonis Vernalis
in the wall of the colon and stimulate the secretion of water
− Ranunculaceae
and electrolytes into the large Intestine.
− Constituent: ADONITOXIN, CYMARIN, K-STROPHANTIN
− Detected by Borntrager test
− (+) red or pink coloration at the lower ammoniacal region
[Link] GRANDIFLORUS
− Occur in plants as hydroxylated, methylated or carboxylated
− CACTUS GRANDIFLORUS
− AKA: Night Blooming Cereus
− From Selenicereus grandifloras [Link] Sagrada
− CACTACEAE − Rhamnuss purshiana; Sacred bark
− Causes positive inotropic effect
Source/s:
[Link] HELLEBORE − Rhamnus purshiana (Rhamnaceae)
− AKA: Christmas Rose − Rhamnus- ancient classical name of buckthorn
− From Helleborus niger − Purshiana — given in honor of the German botanist, Friedrich
− RANUNCULACEAE Pursh
− HELLEBRIN — constituent − Use: Cathartic

3 variety 2 Types of Anthracene compounds

− Black — glycosidal, cardiac stimulant (inotropic) − normal O- glycosides(based on emodin) — about 10 —
− Green and White — alkaloidal, cardiac depressant 20%
− aloinlike C- glycosides- about 80 — 90%
[Link] − Ex. Barbaloin and deoxybarbaloin( chrysaloin)
− From S. kombe and S. hispidus
− Component: K. strophantoside
− G. strophantin (ouabain) - 3rd most important glycoside Main active principals:
available in the market − Cascarosides A → based on optical isomers of barbaloin
− Use in hunting − Cascarosides B
− Apocynaceae − Cascarosides C → based on optical isomers of chrysaloin
− Cascarosides D
[Link] OR SQUILL BULB
− From Urginea maritima
[Link]
− HYACINTHACEAE
− Rhamnus frangula Linne; BUCKS aes - Component of OTC
− Component: SCILLAREN- A, convert to scillarenin which is
product MOVICOL- also contains karaya
more active
− Laxative effect
− (made up of scillarenin, glucose and rhamnose)
− Due to presence of frangulins A and B and related
− Use: expectorant
glucofrangulins
− Red variety: rodenticide (used for rats)
[Link]
[Link]
− It yields not less than 50% of the water soluble extractive
− From Nerium oleander
− Aloes occur on the market as opaque masses that range from
− APOCYNACEAE
reddish black to brownish brown in color
− Genocide in Sri lank
− The taste of each variety of aloe is nauseating and bitter
− Component: Oleandrin, Digitalinum verum
− The characteristic odor 5 disagreeable Aloes are typical
− Oral ingestion — can cause poisoning
xerophytic plants.
− Mimics digoxin − types
o Curacao aloe
o Cape aloe
a. Curacao aloe − -1,6-dihydroxyanthraquinone is the natural constituent, but it
− Aloe barbadensis, Aloe vera is difficult to isolate.
− pharmaceutic aid for Compound Benzoin Tincture . − prepared synthetically from 1, 8-anthraquinone potassium
disulfonate.
[Link] aloe
− Aloe ferox, Aloe africana, Aloe spicata USES: Cathartic → Is an important intermediate in the manufacture
of anthralin and of alizarin and indanthrene dyestuffs
Cathartic → elicits drastic cathartic action

Aloe Vera gel

− Fresh mucilaginous gel contained in the parenchymatous
tissue in the center of the leaves of A. barbadensis
− for the treatment of burns, abrasions and other skin irritations.
− Moisturizing and emollient properties
− (taken from the mucilage of the leaf)

Principal anthraquinone glycosides

− Aloin A — barbaloin
− Aloin B — isobarbaloin

Inactive ingredients including large amounts of ( 16 to 63%) of

a resinous material plus volatile oil

[Link]
− Rheum officinale; Rheum
− R. palmatum; Chinese rhubarb
− R. emodi; Himalayan Rhubarb
− R. webbianum; Indian Rhubarb
− Use: Drastic cathartic

[Link]
− Cassia acutifolia; Alexandria senna
− Cassia angustifolia; Tinnevelly senna ( Fam. Fabaceae)
− Use: - Cathartic
− Senna is graded according to the size of the leaf and the color
of the leaflets:
− Dimeric glycosides- principal active constituents of senna
whose aglycones are composed of aloe-emodin and/or rhein
− Sennosides A and B pair of stereoisomers whose aglycones are
rhein dianthrone (sennidin A and B) Sennosides C and D are
minor constituents having dimeric aglycone Senna pods also
contain useful, active glycosides; some of the primary
glycosides in the pods have as many as 10 sugar molecules
attached to a rhein dianthrone nucleus
− Blue green —best grade, yellowish — poorest
− Cultivated on wet lands resembling rice paddies

CHRYSAROBIN
− Is a mixture of neutral principles obtained from Goa powder
− Obtained in the lysogenous cavities in the wood of Andira
araroba
− Hot benzene is used to extract chrysarobin ( 50-70%) yields
from Goa powder
− A representative sample contains approximately 30- 40% of
chrysophenolanthrone or chrysophenolanthranol, 20%
emodinanthrone-monomethyl ether, and 30% of dehydro-
emodinanthrone- monomethyl ether

USE:
− Keratolytic - psoriasis, trichophytosis and chronic eczema.
− Itis very irritating to mucous membranes and should not be
used on the face or scalp.

DANTHRON or CHRYSARIN
− -1,8- DIHYDROXYANTHRAQUINONE