GLYCOSIDES Flashcards
upon hydrolysis yield one or more sugars
in addition to a nonsugar component known as aglycone, and the sugar component is called as glycone.
GLYCOSIDES
nonsugar component
AGLYCONE/GENIN
sugar component is called?
GLYCONE
The usual linkage between the sugar and the aglycone is an oxygen linkage between the reducing group of a sugar and an alcoholic or phenolic hydroxyl group of the aglycone.
GLYCOSIDES
linkage between the sugar and the aglycone
OXYGEN LINKAGE
the most numerous glycosides ones found in nature.
O-GLYCOSIDES
(S-glycosides)
SULFUR
(N-glycosides)
NITROGEN
(C-glycosides)
CARBON
widely distributed in the plant kingdom
and they play an important role in the regulatory, protective, and sanitary functions of plants.
GLYCOSIDES
Glycosides are widely distributed in the plant kingdom and they play an important role in the ______, _______, and ______ functions of plants.
REGULATORY, PROTECTIVE, SANITARY
Emulsin and other naturally occurring enzymes are
BETA GLYCOSIDES
is the most frequently occurring sugar
and primarily exists in plants
B-GLUCOSE
most frequent occurring glycoside
D-GLUCOSE
( Both alpha- and beta- glycosides are possible but only beta-forms occur in plants.)
Sugar Derivatives:
GLUCURONIC ACID
GALACTURONIC ACID
When sugar formed is glucose, its is term as
GLYCOSIDES
Nomenclature: ending in IN for trivial names
Digitoxin– Digitalis
Salicin– Salix
Prunasin– Prunus
Systematic naming replacing OSE suffix of the parent sugar with OSIDE.
Anoremic prefix (alpha/beta) and the configurational prefix (D/L) immediately precede the sugar stem name, and the chemical name of the aglycone precedes the name of the sugar.
SYSTEM OF NAMING
Sugar component
GLYCONE
If the glycone group of a glycoside is glucose, then the molecule is glucoside. If fructose, then the molecule is fructoside.
GLYCONE
If the glycone group of a glycoside is glucose, then the molecule is ______.
GLUCOSIDE
If the glycone group of a glycoside is fructose, then the molecule is ______.
FRUCTOSIDE
Glycosides are also classified according to the chemical nature of the aglycone. For the purpose of biochemistry and pharmacology, this is the most useful classification
AGLYCONE/GENIN
Glycosides are classified as _______
a-glycosides/ß-glycosides.
Some enzymes such as _____ can only hydrolyzed a- linkages.
a-amylase
Can affect b-linkages
EMULSIN
Cardioactive
(Steroidal)
Anthraquinone
Saponin
Cyanophore
Isothiocyanate
Flavonol
Alcohol
Aldehyde
Lactone
Phenol
Also known as Cardiac glycosides
CARDIOACTIVE (STEROIDAL) GLYCOSIDE
Characterized by their highly specific and powerful action on cardiac muscles.
CARDIOACTIVE (STEROIDAL) GLYCOSIDE
Increases the force of ______ contractions.
SYSTOLIC
Increases the force of systolic contractions.
CARDIOACTIVE (STEROIDAL) GLYCOSIDE
The ___________ depends both on the
structure of the aglycone and the type and number of sugar units to which it is attached.
THERAPEUTIC EFFICIENCY
The therapeutic efficiency depends both on the structure of the aglycone and the type and number of sugar units to which it is attached.
CARDIOACTIVE (STEROIDAL) GLYCOSIDE
Rare sugars:
DIGITALOSE
DIGITOXOSE
CYRAMOSE AND OTHER.
Sugars found in cardioactive glycoside
GLUCOSE
RHAMNOSE
DEOXY SUGAR
Digitoxin, Digitonin, Digitalin
DIGITALIS/FOXGLOVE
Digitalis/Foxglove
DIGITOXIN
DIGITONIN
DIGITALIN
Convallarin, Convallatoxin, Convallamarin
Lilly of the valley root/Convallaria root
Lilly of the valley root/Convallaria root
Convallarin, Convallatoxin, Convallamarin
Scillain, Scillitoxin
SQUILL
Squill
Scillain, Scillitoxin
Strophantin, Strophantic acid
STROPHANTUS
Strophantus
Strophantin, Strophantic acid
Other source of cardioactive glycoside
Asiatic hydrocotyl
Pandacaqui
Periwinkle
Ouabin
Yellow bells
Sources of cardioactive glycosides
DIGITALIS/FOXGLOVE
LILY OF THE VALLEY ROOT / CONVALLARIA ROOT
SQUILL
STROPHANTUS
Are glycosides in which the aglycones are anthracene derivatives are sometimes referred to as the
ANTHRAQUINONE GLYCOSIDES
Stimulant cathartics or purgatives
ANTHRAQUINONE
Increases the tone of the smooth muscles in the cell wall of the colon and stimulate the secretion of water and electrolytes into the large intestine.
ANTHRAQUINONE GLYCOSIDES
Habit-forming laxative dependence and loss of normal bowel function.
ANTHRAQUINONE GLYCOSIDES
Anthraquinone glycosides sources:
Aloe
Frangula
Rhubarb
Sacred bark
Senna
Anthraquinone Glycosides Constituents:
Anthraquinones
Anthranols and Anthrones
Oxanthrols
Dianthrones
Alloin-type/C-glycosides
Yield aglycone known as
SAPOGENIN
Yield aglycone known as Sapogenin– Steroid/Hiterpenoid
SAPONIN GLYCOSIDES
Plant materials containing saponins have long been used for their _______ properties
DETERGENT
Plant materials containing saponins have long been used for their detergent properties
SAPONIN GLYCOSIDES
Characterized by forming colloidal solutions in water with foam upon shaking in an aqueous solution.
SAPONIN GLYCOSIDES
Hemolytic properties and when injected into the blood stream are highly toxic, causing the RBC to disintegrate, especially to cold-blooded animals. – fish poisons
SAPONIN GLYCOSIDES
poisonous saponins
SAPOTOXINS
When taken orally, saponins are comparatively _______.
NONTOXIC
rich in saponins, but it is widely used as a
flavoring of pharmaceuticals and beverages
SARSAPARILLA
Sources of Saponin Glycosides
SARSAPARILLA
GINSENG
GLYCYRRHIZA/LICORICE ROOT
Other sources of saponin glycosides:
SENEGA
SOAP BARK
Glycosides yielding hydrocyanic acid as one of the products of hydrolysis.
CYANOPHORE GLYCOSIDES
Also known as Cyanogenic glycosides
CYANOPHORE GLYCOSIDES
Cyanophore glycosides is also known for?
CYANOGENIC GLYCOSIDES
is a chemical defense response to
organisms damaging the plant tissue when feeding on intact plant parts or attacking the plant through a site of injury.
CYANOGENESIS
(CYANOPHORE CAN BE USED AS FLAVORING AGENTS)
Amygdalin-containing preparations known as Laetrile/Vitamin B17 and possibly for sickle cell anemia control.
ANTICANCER
most widely distributed
AMYGDALIN
common cyanophore glycoside
MANDELONITRILE (BENZALDEHYDE CYANOHYDRIN)
Sources of cyanophore glycosides:
BITTER ALMONDS - AMYGDALIN
WILD CHERRY / WILD BLACK CHERRY TREE - PRUNASIN (D-MANDELONITRILE)
CASSAVA - MANNIHOTOXIN
APRICOT PITS - AMYGDALIN
Mannihotoxin
CASSAVA
Prunasin (D-Mandelonitrile)
WILD CHERRY TREE/ WILD BLACK CHERRY TREE
Also known as Glucosinolate
ISOTHIOCYANATE GLYCOSIDES
Isothiocyanate glycoside is also known as
GLUCOSINOLATE
Act as feeding deterrents against insects and mammals.
ISOTHIOCYANATE GLYCOSIDES
Anticarcinogenic
ISOTHIOCYANATE GLYCOSIDES
canola oil
OILSEEDS (RAPESEED)
mustard, horseradish
CONDIMENTS
broccoli, cabbage, turnips
VEGETABLES
Sources of Isothiocyanate Glycosides:
BLACK MUSTARD - SINIGRIN
WHITE MUSTARD - SINALBIN
GARLIC
sinigrin
BLACK MUSTARD
Sinalbin
WHITE MUSTARD
White mustard
SINALBIN
Black mustard
SINIGRIN
Generally termed as Flavonoids (Flavone, Isoflavone, Flavonol and Flavanone)
FLAVONOL GLYCOSIDES
Flavonol glycosides is generally termed as?
FLAVONOIDS (FLAVONE, ISLOFLAVONE, FLAVANOL, FLAVANONE)
Widely distributed in nature in the free state or as glycosides but are more common in higher plants particularly in red, blue, of yellow pigments of flowers
and fruits.
FLAVONOL GLYCOSIDES
Widely distributed in nature in the free state or as glycosides but are more common in higher plants particularly in _____, _____, of ______ pigments of flowers
and fruits.
RED BLUE YELLOW
Widely distributed in nature in the free state or as glycosides but are more common in higher plants particularly in ____, _____, of _____ pigments of flowers
and fruits.
RED BLUE YELLOW
Rutin
BUCKWHEAT AND RUE
Sources of Flavonol Glycosides:
BUCKWHEAT AND RUE
QUERCUS AND TINCTORIA
CITRUS FRUITS
MILK THISTLE
Quercitrin
Quercus Tinctoria
Vitamin P/Permeability Factor
RUTIN AND HESPERIDIN
Hesperidin
CITRUS FRUITS
Hesperidin, Hesperitin, Diosmin, Naringen.
CITRUS BIOFLAVONOIDS
As dietary supplement
RUTIN AND CITRUS FLAVONOIDS
Ripe fruits of Silybum marianum
Silymarin
Supportive treatment for chronic inflammatory liver conditions and cirrhosis.
MILK THISTLE
Upon hydrolysis, Salicin from Willow and Poplar barks yields Salicyl alcohol (Saligenin ) and Glucose.
ALCOHOL GLYCOSIDES
Sources of Alcohol Glycosides:
SALICIN
species of Salix and Populus
SALICIN
Sources under Salicin in Alcohol Glycosides:
Salix Purpurea and Salix Fragilis
Antirheumatic
Analgesic
Other sources of Alcohol Glycosides:
HAMEMELIS
MAZEREUM
VIBURNUM
XANTHOXYLLUM
Consist of glucose combined with Hydroxybenzaldehyde, thus representing a glycoside having an aldehyde aglycone.
ALDEHYDE GLYCOSIDES
Sources of Aldehyde Glycosides:
VANILLA -VANILLIN
VANILLIN
VANILLA
Uses as pharmaceutic acid and flavoring agent?
VANILLA
a derivative of benzo-a-pyrone has been found in about 150 species belonging to over 30 different families
COUMARIN
Coumarin
TONKA SEEDS
Santonin
SANTONICA
Camtharidin
CANTHARIDES
Formerly use as flavoring agent, anticoagulant
SEEDS
Antispasmodics
BARKS
Uterine Sedatives:
TONKA SEEDS
SANTONICA
CANTHARIDES
SEEDS
BARKS
Aglycone group of many of the naturally-occurring glycosides are phenolic in character.
PHENOL GLYCOSIDES
Sources of Phenol Glycosides:
UVA URSI
ROOT BARKS OF ROSACEOUS PLANTS
BAPTISIA
IRIS SPECIES
Arbutin
UVA URSI
PHLORIDZIN
Root barks of Rosaceous plants
Phloridzin
Root barks of Rosaceous plants
Baptisin
Baptisia
Iridin
IRIS SPECIES