Glycosides

Acetals/ ethers o Sugar attachments- more soluble and increase

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

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 Rhizones and roots of A.
Digoxin- most widely used cannabinum/androsaemifoliu
o More rapidly absorbed from GIT m
Strophanthus Apocynaceae
o Poison arrow/ onaya- seed Apocannoside,
o S. kombe/ hispidus- Apocynaceae cyanocannoside
o K- strophanthoside (glycoside)- K- strophanthidin
(aglycone) Adonis or pheasants eye
S. gratus/ Acokantheraschimperi A. vernalis
o Ouabain- G- strophanthin Ranunculaceae- adonitoxin,
o Ouabagenin- G- strophanthidin cymarin, K-strophanthin
Cactus grandiflorus/night blooming cerius
Squill- sea onion Cactaceae
o Urginea maritime/ indica Liliaceae
o cebolla marina- sea onion Black hellebore/christmas rose
Scillaren A Rhizones and roots
o Enzymatic hydrolysis- proscillaridin A (aglycone) Hellebores niger
o Acid hydrolysis- scillaridin A (aglycone) Ranunculaceae
o Scillaren B- glycoside o Helleborin
o Glucoscillaren A o Helleborein
o Proscillaridin A (can be further change)- o Helleberin (20 x
Scillarenin (final aglycone) (Scillaridin) more powerful)
o Expectorant, emetic, cardiotonic, diuretic Dangerous (obsolete)
redsquill o Hellebrigenin
red variety Green hellebore
scilliroside o Cardiac depressant
rat poison (U. maritima) Adelfa
Leaves of Neriumorlander
convallaria or lily of the valley root Apocynaceae
Oleandrin
rhizome and roots of c. majalisliliaceae

convallatoxin, convallatoxol, convalloside
ANTRAQUINONE GLYCOSIDES

Exhibit little therapeutic activity
apocynum/black indian hemp/ dog bane/canadian hemp
Sugar residue
 o Facilitates absorption and translocation of the Dimeric glycosides
aglycone to the site of action o Aloe emodin/rhein
Stimulant cathartics o Sonnosides A and B (rheindianthrones-sennidin A
o Increase tone of the smooth muscle in the wall of and B)
large intestines o Sennosides C and D (dimericaglycones- rhein and
Emodin, aloe emodin, chrysophanic acid rhein aloe emodin)
Cascara sagrada o Cathartic (senokot)
Sacres/bitter/yellow/chittein bark/coffee berry o Acapulko/katanda (cassia alata)(ringworm)
Ramnuspurshianus (rhamnaceae) o Alexandria/tunnevelly
Aged for 1 year
Reduced forms of emodin type glycosides converted to Chrysarobin
monomeric oxidized glycosides with milder cathartic Mixture of neutral principles from Goa powder
activity Andiraararoba (fabaceae)
Inner surface of bark not exposed to sunlight to retain Chrysophenolanthrone/chrysoanthranol (anthranols and
yellow color anthrones
O and C glycosides Keratolytic agent for psoriases, trichophytosis and chronic
o Cascarosides A,B,C, and D eczema
C glycosides Very irritating to the mucous membrane
o Barbaloin and deoxybarbaloin (chrysaloin) Danthron
Cascarosides A, B, C, D Chrysazin
o Primary glycosides of barbaloin and chrysaloin Orange crystalline powder
Cathartic to correct habitual constipation Cathartic,dyestuffs
Bitter taste ad activity reduced by alkaline earths or Hypericum
magnesium oxide St. johns wort
Casanthranol H. perforatum (hypericaceae)
o A purified mixture of the anthranol glycosides Hypericum and pseudohypericin
from cascara sagrada Hyperforin (lipophilic extract)
Mild to moderate depression (natures Prozac)
Frangula
Buckthorn/alder bark CYANOGENIC GLYCOSIDES
R. frangula Cynogenic
Frangulin o Amygdalin and prunasin
o Franguloside A and B= emodin o Emulsion (amygdalase and prunase)
Tonic diuretic, cathartic (veterinary), emetic (fresh bark) Amygdalin
o Mandelonitrileglucoside (prunasin) + glucose
Aloe o Mandelonitrile (benzaldehyde-cyanohydrin) +
Dried latex (juice) of the leaves glucose
Aloe barbadensis/ vera/ ferox/Africana/spicata (liliaceae) o Benzaldehyde + HCN
Barbaloin (aloe emodin) Laetrile/vitamin B17
o Main glycoside o Amygdalin- containing preparation with anti
Aloinosides, chrysophanic acid cancer claims
Pharmaceutic aid for compound benzoic tincture, cathartic o Control of sickle cell anemia not recognized by
Activity released by soap and alkaline salts FDA
Carminative reduced griping effects Wild cherry
Treatment of burns, abrasion and other skin irritations, o Prunusvirginiana
moisturizing, and emollient effects o Stem bark of prunusserotina
Cell proliferative (wound-healing) o Rosaceae
No scientific or clinical evidence to support the therapeutic o Lenticels
use of stabilized aloe gel products o Prunasin, prunase
Sabila/acibar o Mandelonitrile
o Sedative expectorant, syrup as flavoring
Rhubarb rheum
Chinese rhubarb
o Rhizome and root of R. officinale/planatum FLAVANOL GLYCOSIDES
Polygonaceae Flavonoids
Indian/ Himalayan rhubarb Yellow pigment- rutin, quercitin, citus bioflavonoids
R. emodi/webbianum [hesperidin (aglycone)(hesperitin), diosmin, naringen]
Rheinanthrones Rutin and hesperidin (glycosides)
Emodin, aloe emodin, chrysophanic acid, rhein o Vitamin P factors or permeability factor
Astringent principles Capillary bleeding and increased
o Glucogallin, tetrarin, rheotannic acid capillary fragility
o Grittiness Treatment of colds
o Calcium oxalate crystals Rue
o Aroma rheosmin o Garden rue/herb of grace
o Cathartic, tonic, bitter stomachic o Leaves of rutagraveolens (rutaceae)
Senna o Rutin (glycoside) = quercitin (aglycone)
Hojlas de sen o Capillary bleeding and increased capillary
Leaflets of cassia acutifolia/angustifolia fragility
Fabaceae
Graded according to size and color of leaflets
o Blue green (best) ISOTHIOCYANATE GLYCOSIDES
o Yellowish greesn (poorest)
 Mustards o Flowerhead of Artemisia cina, martima
o Black, crown, Chinese, white mustard (asteraceae)
o Yellow or English mustard o Santonin formerly used as an anthelmintic
o Sinapisnigra / alba o Niog-niogan
o Brassica nigra/juncea/alba Brassicaceae Quisqualisindica
o Sinigrin (potassium myronate) = Combretaceae
allylisothiocyanate (volatile oil) (aglycone) Cantharides
Glycoside ng black o Insects of cantharis vesicatoria (meloidae)
o Sinalbin = acrinylisothiocyanate (less volatile) o Spanish/Russian blistering flies
(aglycone) o Mylobriscirchorii (Chinese BF)
Glycoside ng white o Cantharidin
o Myrosin (enzyme that hydrolyze the glycosides of Irritant, blistering agent, vesicant
mustards) o warts removal
o Local irritant, emetic, rubefacient (reddening of coumarin
the skin), and vesicant o lactone of orthohydroxycinnamic acid
o condiment o sweet vernal grass, sweet clover, sweet scented
bedstraw, red clover
ALCOHOL GLYCOSIDES o former flavoring agent
Popular bud, willow bud, balm of gilead buds drug interaction
Bark of salixpurpurea/fragilis bishydroxycoumarin/dicumarol
Leaf buds of populous candicans/tacamahacca (salicaceae) o melilotusofficinalis
Salicin (natural forereunner of aspirin)(antirheumatic) and o fabaceae
populin o anticoagulant
Saligenin (salicyl alcohol) psoralens
Emulsin (amygdalase + prunasin) o photosensitizing furocoumarins
Analgesic, anti-inflammatory, febrifuge, expectorant methoxsalen/xanthotoxin
o facilitate repigmentation, control severe psoriasis
PHENOL GLYCOSIDES (UV radiation)
arbutin, hesperidin, phloridzin
baptisin MISCELLANEOUS GLYCOSIDAL DRUGS
iridin BITTER
uva-ursi o Gentian/bitter root/yellow root
o bearberry/rockberry Root and rhizome of gentian lutea
o leaf of arctostaphylosuva- (gentianaceae)
ursi/coactylis/adenotricha (ericaceae) Gentiopicrin/gentiamarin/gentianin
o arbutin Gentiogenin
hydroquinone and glucose Bitter tonic, carminative
o diuretic and astringent o Quassia/bitter wood/corales
Heartwood of picrasma excels?
Quassiaamara
ALDEHYDE GLYCOSIDES Simarubaceae
Vanilla Quassin (picrasmin and neoquassin)
o Cured fruit of V. fragrans/plantifolia/tahitensis Bitter tonic, febrifuge, carminative,
(orchidaceae) denatured alcohol
Green fruits Sweet
o Glucovanillin o Glycyrrhiza
Other name: Vanilloside or Avenein Neutral principle
Glucose and vanillin (aglycone) o Cocculus/fish berry/ Indian berry/ ligtang/
o Glucovannilic alcohol balasing
Glucose and vanillic alcohol Fruit of anamirtacocculus
Vanillic aldehyde Menispermaceae
4-hydroxy-3-methoxybenzaldehyde Cocculin/picrotoxin
Methylprotocatechuic aldehyde Menispermine/paramenispermine
Vanillin (principal flavoring agent) Coloring principles
(aglycone) o Red saunders/red sandalwood
Mexican (veracruz vanilla) Heartwood of pterocarpussantalinus
o Best grade Fabaceae
Synthetic sources of vanillin Santalin
o Coniferin, eugenol, lignin o Hematoxylon/logwood
Vanilla pods Haematoxyloncampechianum
o Confectionery and perfumery Hematoxylon, hematein
o Crocus/Spanish saffron
LACTONE GLYCOSIDES Stigmas of crocus sativus
Coumarin, skimming, aesculin, daphnin, fraxin, scopolin, Iridaceae
limettin Crocin(color), picrocrocin (taste),
Tonka beans, tonca seed, tonquin beans safranal (odor)
o Seed of dipteryx/oppositifolia, Coloring and flavoring agent
coumarounaodorata (fabaceae) o Carthamus/ American saffron/safflower/ kasubha
o Coumarin Tubular florets of carthamustinctorius
o Tobacco manufacture and perfumery Asteraceae
o Formerly used as flavoring agent o Cochineal/coccus
Santonica, levant, Alexandria wormseed Female insects of coccus cacti
 Cactaceae Demulcent, expectorant, flavoring, mask taste of bitter
Carminic acid, coccerin drugs, surfactant
Volatile oils Added to beer to increase foamness
o Arnica/talpica/Mt. tobacco Added to root beer to mask bitter taste
Flowerheads of arnica Glycyrrhetic acid for anti inflammatory property, peptic
Montana/fulgens/sororia/cardifolia ulcer, addisons disease
Asteraceae Glycyrrhizin- increases fluid and sodium retention,
Arnicin promotes potassium depletion (hypertension)
Local irritant, vulnerary
Tincture arnica Dioscorea (yams)
o Calamus/ sweet flag/ lubigan Root od D. spiculifora dioscin = diosgenin (major precursor
Peeled rhizome of acoruscalamus of glucocorticosteroids) and botogenin
Araceae Diuretic, diaphoretic, expectorant, and antispasmodic
Acorin
Carminative Dioscorea floribunda
Best source of steroids
SAPONIN GLYCOSIDES
Colloidal solutions in water Ginseng
Foam on shaking Root of Panax ginseng/quinquefolium (araliaceae)
Bitter acrid taste Panaxosides, ginsenosides, chikusetsusaponins
Sternutatory Ginsengenin (aglycone)
Irritating to the mucous membrane Diuretic, stomachic, carminative, diabetis, insomnia,
Destroy RBC by hemolysis sexual impotence, anemia, gastritis
Toxic (sapotoxin) Favorative Chinese remedy
Fish poisons
Sapogenins Senega (snakeroot)
Precursor for cortisone (steroidal sapogenins) Polygala senega (polygalaceae)
Outstanding plant steroids for cortisone production: Knotty crown, distinct ridge or kneel, methylsalicylate odor
o Liliaceae Senegin = senegenin + polygalic acid, pectin
o Amaryllidaceae Expectorant
o Dioscoreaceae (monocots)
o Apocynaceae (dicot) Quillaja (soap/murillo/china bark)
Diosgenin and botogenin- dioscorea Q. saponaria (rosaceae)
Hecogenin, manogenin, gitogenin- agave Quiallain, quillajic acid, calcium oxalate crystals
Sarsasapogenin, smilagenin- smilax (sternutatory)
Sarmentogenin- strophanthus Detergent, emulsifier, fire extinguisher, cleansing silk,
Sitosterol- crude vegetable oil metal polisher
Saponins is: Gogo (Entadascandens/phaseoloides- fabaceae)
o Neutral (steroidal)
o Acid (triterpenoid) Sarsaparilla (Smilax aristolochiaefolia-mexican)
Regelii (Honduras), febrifuga (Ecuadorian)- liliaceae
Glycyrrhiza Sarsaponin, smilacin, reageliin, stigmasterol =
Licorice or sweet wood sarsapogenin, smilagenin
Thizome and roots of G. glabra variety.,typica (Spanish) flavoring
variety., glandulifera (Russian)
Glycyrrhizin (glycyrrhizic acid)= glycyrrhetic acid and
glucuronic acid