Glycosides

Acetals/ ethers
-OH of the sugar is condensed with a OH group of the non-sugar component
Secondary OH is condensed within the sugar molecule itself to form and oxide ring
Sugars (-D-glucose)
Mineral acids and enzymes
Sugar component- glycone
Non-sugar component- aglycone/ genin
Regulatory/protective/ sanitary function
o Cardiotonics/laxative/ analgesic
Steroidal aglycones- cerdenolide and bufadienolide
Pharmacological effectiveness
o Aglycones- inherent activity
o Sugar attachments- more soluble and increase power of fixation to the heart muscle
Heart beats- depolarization
o Change in the permeability of the cell membrane
o Na+ into the ell and K+ moves out
o Na+, K+, -ATPase supplies energy from ATP to reverse process
o Pump Na+ out of the cell and K into the cell
Inhibit Na+, K+ -ATPase
o Increase in Na and decrease in K within the cells
o Stimulates secondary Na+, Ca++ exchange mechanism
o Remove intracellular Na increase in intracellular Ca++

Digitalis
Foxglove
Digitalis purpurea (Scrophulariaceae)
Assay- pigeon
Digitoxigenin Gitoxigenin (aglycone) Gitaloxigenin (aglycones)
Pupurea glycoside A Purpurea glycoside B Glucogitaloxin
Digitoxin Gitoxin Gitaloxin
(most lipid soluble)
Congestive heart failure, tachycardia, atrial flutter, atrial fibrillation

Digitalis lanata
Grecian foxglove
Lanatoside A Digitoxigenin
Lanatoside B Gitoxigenin
Lanatoside C (no counterpart)
Digoxin (no counterpart) Digoxigenin
Lanatoside D (no counterpart) Diginatigenin
Lanatoside E Gitaloxigenin

Cardiac glycosides
Digoxin- most widely used
o More rapidly absorbed from GIT
Strophanthus
o Poison arrow/ onaya- seed
o S. kombe/ hispidus- Apocynaceae
o K- strophanthoside (glycoside)- K- strophanthidin (aglycone)
S. gratus/ Acokanthera schimperi
o Ouabain- G- strophanthin
o Ouabagenin- G- strophanthidin

Squill- sea onion

o Urginea maritime/ indica Liliaceae
o cebolla marina- sea onion
Scillaren A
o Enzymatic hydrolysis- proscillaridin A (aglycone)
o Acid hydrolysis- scillaridin A (aglycone)
o Scillaren B- glycoside
o Glucoscillaren A
o Proscillaridin A (can be further change)- Scillarenin (final aglycone) (Scillaridin)
 o Expectorant, emetic, cardiotonic, diuretic
red squill
red variety
scilliroside
rat poison (U. maritima)
ANTRAQUINONE GLYCOSIDES
convallaria or lily of the valley root Exhibit little therapeutic activity
rhizome and roots of c. majalis liliaceae Sugar residue
convallatoxin, convallatoxol, convalloside o Facilitates absorption and translocation
of the aglycone to the site of action
apocynum/black indian hemp/ dog bane/canadian Stimulant cathartics
hemp o Increase tone of the smooth muscle in
Rhizones and roots of the wall of large intestines
A. Emodin, aloe emodin, chrysophanic acid rhein
cannabinum/androsae
mifolium Cascara sagrada
Apocynaceae Sacres/bitter/yellow/chittein bark/coffee berry
Apocannoside, Ramnus purshianus (rhamnaceae)
cyanocannoside Aged for 1 year
Reduced forms of emodin type glycosides
Adonis or pheasants eye converted to monomeric oxidized glycosides
A. vernalis with milder cathartic activity
Ranunculaceae- Inner surface of bark not exposed to sunlight to
adonitoxin, cymarin, K- retain yellow color
strophanthin O and C glycosides
Cactus grandiflorus/night blooming cerius o Cascarosides A,B,C, and D
Cactaceae C glycosides
o Barbaloin and deoxybarbaloin
Black hellebore/christmas rose (chrysaloin)
Rhizones and roots Cascarosides A, B, C, D
Hellebores niger o Primary glycosides of barbaloin and
Ranunculaceae chrysaloin
o Helleborin Cathartic to correct habitual constipation
o Helleborein Bitter taste ad activity reduced by alkaline
o Helleberin (20 x earths or magnesium oxide
more powerful) Casanthranol
Dangerous (obsolete) o A purified mixture of the anthranol
o Hellebrigenin glycosides from cascara sagrada
Green hellebore
o Cardiac Frangula
depressant Buckthorn/alder bark
Adelfa R. frangula
Leaves of Nerium Frangulin
orlander o Franguloside A and B= emodin
Apocynaceae Tonic diuretic, cathartic (veterinary), emetic
Oleandrin (fresh bark)

Aloe
Dried latex (juice) of the leaves
Aloe barbadensis/ vera/ ferox/Africana/spicata
(liliaceae)
Barbaloin (aloe emodin)
o Main glycoside
Aloinosides, chrysophanic acid
Pharmaceutic aid for compound benzoic
tincture, cathartic
Activity released by soap and alkaline salts
Carminative reduced griping effects
Treatment of burns, abrasion and other skin
irritations, moisturizing, and emollient effects
Cell proliferative (wound-healing)
No scientific or clinical evidence to support the
therapeutic use of stabilized aloe gel products
Sabila/acibar

Rhubarb rheum
 Chinese rhubarb
o Rhizome and root of R.
officinale/planatum
Polygonaceae

Indian/ Himalayan rhubarb

R. emodi/webbianum
Rhein anthrones
Emodin, aloe emodin, chrysophanic acid, rhein
Astringent principles CYANOGENIC GLYCOSIDES
o Glucogallin, tetrarin, rheotannic acid Cynogenic
o Grittiness o Amygdalin and prunasin
o Calcium oxalate crystals o Emulsion (amygdalase and prunase)
o Aroma rheosmin Amygdalin
o Cathartic, tonic, bitter stomachic o Mandelonitrile glucoside (prunasin) +
Senna glucose
Hojlas de sen o Mandelonitrile (benzaldehyde-
Leaflets of cassia acutifolia/angustifolia cyanohydrin) + glucose
o Benzaldehyde + HCN
Fabaceae
Laetrile/vitamin B17
Graded according to size and color of leaflets
o Amygdalin- containing preparation with
o Blue green (best)
anti cancer claims
o Yellowish greesn (poorest)
o Control of sickle cell anemia not
Dimeric glycosides
recognized by FDA
o Aloe emodin/rhein
Wild cherry
o Sonnosides A and B (rhein dianthrones-
o Prunus virginiana
sennidin A and B)
o Stem bark of prunus serotina
o Sennosides C and D (dimeric
o Rosaceae
aglycones- rhein and aloe emodin)
o Lenticels
o Cathartic (senokot)
o Prunasin, prunase
o Acapulko/katanda (cassia alata)
o Mandelonitrile
(ringworm)
o Alexandria/tunnevelly o Sedative expectorant, syrup as
Chrysarobin flavoring
Mixture of neutral principles from Goa powder
Andira araroba (fabaceae)
FLAVANOL GLYCOSIDES
Chrysophenolanthrone/chrysoanthranol
Flavonoids
(anthranols and anthrones
Yellow pigment- rutin, quercitin, citus
Keratolytic agent for psoriases, trichophytosis
bioflavonoids [hesperidin (aglycone)
and chronic eczema
(hesperitin), diosmin, naringen]
Very irritating to the mucous membrane
Rutin and hesperidin (glycosides)
Danthron
o Vitamin P factors or permeability factor
Chrysazin
Capillary bleeding and
Orange crystalline powder
increased capillary fragility
Cathartic,dyestuffs
Treatment of colds
Hypericum
Rue
St. johns wort
o Garden rue/herb of grace
H. perforatum (hypericaceae)
o Leaves of ruta graveolens (rutaceae)
Hypericum and pseudohypericin
o Rutin (glycoside) = quercitin (aglycone)
Hyperforin (lipophilic extract)
o Capillary bleeding and increased
Mild to moderate depression (natures Prozac)
capillary fragility

ISOTHIOCYANATE GLYCOSIDES

Mustards
o Black, crown, Chinese, white mustard
o Yellow or English mustard
o Sinapis nigra / alba
o Brassica nigra/juncea/alba
Brassicaceae
o Sinigrin (potassium myronate) =
allylisothiocyanate (volatile oil)
(aglycone)
Glycoside ng black
 o Sinalbin = acrinyl isothiocyanate (less
volatile) (aglycone)
Glycoside ng white
o Myrosin (enzyme that hydrolyze the
glycosides of mustards)
o Local irritant, emetic, rubefacient
(reddening of the skin), and vesicant
o condiment

ALDEHYDE GLYCOSIDES
ALCOHOL GLYCOSIDES Vanilla
Popular bud, willow bud, balm of gilead buds o Cured fruit of V.
Bark of salix purpurea/fragilis fragrans/plantifolia/tahitensis
Leaf buds of populous candicans/tacamahacca (orchidaceae)
(salicaceae) Green fruits
Salicin (natural forereunner of aspirin) o Glucovanillin
(antirheumatic) and populin Other name: Vanilloside or
Saligenin (salicyl alcohol) Avenein
Emulsin (amygdalase + prunasin) Glucose and vanillin (aglycone)
Analgesic, anti-inflammatory, febrifuge, o Glucovannilic alcohol
expectorant Glucose and vanillic alcohol
Vanillic aldehyde
PHENOL GLYCOSIDES 4-hydroxy-3-
arbutin, hesperidin, phloridzin methoxybenzaldehyde
baptisin Methylprotocatechuic aldehyde
iridin Vanillin (principal flavoring
uva-ursi agent) (aglycone)
o bearberry/rockberry Mexican (vera cruz vanilla)
o leaf of arctostaphylos uva- o Best grade
ursi/coactylis/adenotricha (ericaceae) Synthetic sources of vanillin
o arbutin o Coniferin, eugenol, lignin
hydroquinone and glucose Vanilla pods
o diuretic and astringent o Confectionery and perfumery

LACTONE GLYCOSIDES
Coumarin, skimming, aesculin, daphnin, fraxin,
scopolin, limettin
Tonka beans, tonca seed, tonquin beans
o Seed of dipteryx/oppositifolia,
coumarouna odorata (fabaceae)
o Coumarin
o Tobacco manufacture and perfumery
o Formerly used as flavoring agent
Santonica, levant, Alexandria wormseed
o Flowerhead of Artemisia cina, martima
(asteraceae)
o Santonin formerly used as an
anthelmintic
o Niog-niogan
Quisqualis indica
Combretaceae
Cantharides
o Insects of cantharis vesicatoria
(meloidae)
o Spanish/Russian blistering flies
o Mylobris circhorii (Chinese BF)
o Cantharidin
Irritant, blistering agent,
vesicant
o warts removal
coumarin
o lactone of ortho hydroxycinnamic acid
 o sweet vernal grass, sweet clover, sweet Asteraceae
scented bedstraw, red clover Arnicin
o former flavoring agent Local irritant, vulnerary
drug interaction Tincture arnica
o Calamus/ sweet flag/ lubigan
bishydroxycoumarin/dicumarol
Peeled rhizome of acorus calamus
o melilotus officinalis Araceae
o fabaceae Acorin
o anticoagulant Carminative
psoralens
o photosensitizing furocoumarins
methoxsalen/xanthotoxin
o facilitate repigmentation, control
severe psoriasis (UV radiation) SAPONIN GLYCOSIDES
Colloidal solutions in water
Foam on shaking
Bitter acrid taste
Sternutatory
Irritating to the mucous membrane
MISCELLANEOUS GLYCOSIDAL DRUGS Destroy RBC by hemolysis
BITTER Toxic (sapotoxin)
o Gentian/bitter root/yellow root Fish poisons
Root and rhizome of gentian lutea Sapogenins
(gentianaceae) Precursor for cortisone (steroidal sapogenins)
Gentiopicrin/gentiamarin/gentianin Outstanding plant steroids for cortisone production:
Gentiogenin o Liliaceae
Bitter tonic, carminative o Amaryllidaceae
o Quassia/bitter wood/corales o Dioscoreaceae (monocots)
Heartwood of picrasma excels? o Apocynaceae (dicot)
Quassia amara Diosgenin and botogenin- dioscorea
Simarubaceae Hecogenin, manogenin, gitogenin- agave
Quassin (picrasmin and Sarsasapogenin, smilagenin- smilax
neoquassin) Sarmentogenin- strophanthus
Bitter tonic, febrifuge, carminative, Sitosterol- crude vegetable oil
denatured alcohol Saponins is:
Sweet o Neutral (steroidal)
o Glycyrrhiza o Acid (triterpenoid)
Neutral principle
o Cocculus/fish berry/ Indian berry/ ligtang/ Glycyrrhiza
balasing Licorice or sweet wood
Fruit of anamirta cocculus Thizome and roots of G. glabra variety., typica
Menispermaceae (Spanish) variety., glandulifera (Russian)
Cocculin/picrotoxin Glycyrrhizin (glycyrrhizic acid)= glycyrrhetic acid and
Menispermine/paramenispermine glucuronic acid
Coloring principles Demulcent, expectorant, flavoring, mask taste of
o Red saunders/red sandalwood bitter drugs, surfactant
Heartwood of pterocarpus Added to beer to increase foamness
santalinus Added to root beer to mask bitter taste
Fabaceae Glycyrrhetic acid for anti inflammatory property,
Santalin peptic ulcer, addisons disease
o Hematoxylon/logwood Glycyrrhizin- increases fluid and sodium retention,
Haematoxylon campechianum promotes potassium depletion (hypertension)
Hematoxylon, hematein
o Crocus/Spanish saffron Dioscorea (yams)
Stigmas of crocus sativus Root od D. spiculifora dioscin = diosgenin (major
Iridaceae precursor of glucocorticosteroids) and botogenin
Crocin(color), picrocrocin (taste), Diuretic, diaphoretic, expectorant, and antispasmodic
safranal (odor)
Coloring and flavoring agent Dioscorea floribunda
o Carthamus/ American saffron/safflower/ Best source of steroids
kasubha
Tubular florets of carthamus Ginseng
tinctorius Root of Panax ginseng/quinquefolium (araliaceae)
Asteraceae Panaxosides, ginsenosides, chikusetsusaponins
o Cochineal/coccus Ginsengenin (aglycone)
Female insects of coccus cacti Diuretic, stomachic, carminative, diabetis, insomnia,
Cactaceae sexual impotence, anemia, gastritis
Carminic acid, coccerin Favorative Chinese remedy
Volatile oils
o Arnica/talpica/Mt. tobacco Senega (snakeroot)
Polygala senega (polygalaceae)
Flowerheads of arnica
Montana/fulgens/sororia/cardifolia
 Knotty crown, distinct ridge or kneel, Regelii (Honduras), febrifuga (Ecuadorian)- liliaceae
methylsalicylate odor Sarsaponin, smilacin, reageliin, stigmasterol =
Senegin = senegenin + polygalic acid, pectin sarsapogenin, smilagenin
Expectorant flavoring

Quillaja (soap/murillo/china bark)

Q. saponaria (rosaceae)
Quiallain, quillajic acid, calcium oxalate crystals
(sternutatory)
Detergent, emulsifier, fire extinguisher, cleansing
silk, metal polisher
Gogo (Entada scandens/phaseoloides- fabaceae)

Sarsaparilla (Smilax aristolochiaefolia-mexican)