Drugs Containing Glycosides 2020 1
Drugs Containing Glycosides 2020 1
GLYCOSIDE
a.k.a. sugar ethers
Glycon – sugar content
-can consist of a single sugar group (monosaccharide) or several sugar groups
(oligosaccharide).
-Aglycon or genin part of the glycoside – non sugar component
Is any molecule in which a sugar group is bounded through its anomeric carbon to
another group via glycosidic bond.
The sugar found in glycosides maybe glucose, rhamnose (mono) or rarely deoxysugar
(cymarose- found in cardiac glycoside).
The term glycoside is a very general which embraces all the many and varied
Combinations of sugar and aglycons.
PROPERTIES:
1. They are crystalline or amorphous substances that are soluble in water or alcohols.
2. Insoluble in organic solvents like benzene and ether.
3. The aglycone part is soluble in organic solvents like benzene or ether.
4. They are hydrolysed by water, enzymes, and mineral acids.
5. They are optically active.
B. N-glycosides - sugar molecule is combined with N in the NH- (amino group) of aglycone.
(ex. Nucleosides)
Class Example
1. Anthraquinone glycoside Senna, aloe, ect.
2. Sterol and cardiac glycoside Digitalis, Squill, ect.
3. Saponin glycoside Dioscorea, licorice, ginseng, ect.
4. Cyanogenetic and cyanophoric Bitter almond, wild chery bark
5. Thiocynate and Isothiocynate glycoside Black mustard
6. Flavone glycoside Gingko
7. Aldehyde glycoside Vanilla
8. Phenol glycoside Bearberry
9. Steroidal glycoside Solanum
10. Bitter and Misc. glycoside Gentian, Picrrohiza, chirata, ect
GLYCOSIDES FAMILIES
I. ANTHRACENE GLYCOSIDES
2. ALOE -is the dried juice collected by incision, from the bases of the leaves of various
species of aloe. Aloe perryi, A. vera, A. barbadensis Mil. A. ferox Miller.
Aloe barbadensis
Cons: crystalline Aloins 30%
ß-barbaloin
Isobarbaloin
Isomer aloins
Amorphous aloin, resin, emodin, and aloe -emodin
Barbaloin (present in all varieties)
Uses:
1. Purgative
2. In higher doses may act as abortifacient
3. Vermifuge
4. Emmenagogue
5. Emollient
6. Stimulant
7. Stomachic
8. Tonic
9. Vulnerary
10. Extract is antibacterial
11. Clear gel of the leaf makes an excellent treatment for wounds, burns and other skin
disorder.
12. Speeding rate of healing and reducing the risk of infection.
13. Give soothing effect on all sort of burns and other skin problems.
4. CASCARA BARK (syn: Cascara sagrada, sacred bark, Buckthorn, chittem bark)
Dried bark of Rhamnus purshiana DC.
Cons: Aloin
Barbaloin
Uses:
1. Gentle Laxative
2. Useful in chronic constipation
3. The bark has tonic properties, promoting gastric digestion and appetite
4. Taken internally in the treatment of digestive complains, hemorrhoids, liver
problems and jaundice
II. STEROL OR CARDIAC GLYCOSIDE
1. DIGITALIS LEAVES (syn: digitalis, purple foxglove, finger flower, lady’s glove,
foxglove leaves, folia digitalis)
Dried leaves of Digitalis purpurae linne
Cons:
Foxglove Grecian foxglove (D. lanata)
Gitoxin Digoxin
Gitalotoxin Des acetyl lanatoside (deslanoside)
Uses:
1. foxglove is a widely used herbal medicine with a recognized stimulatory effect upon
the heart
2. used in allopathic medicine in the treatment of heart complaints
3. profound tonic effect upon a diseased heart, enabling the heart to beat more
slowly, powerfully, and regularly without requiring more oxygen
4. it stimulates the flow of urine which lowers the volume of the blood and lessens the
load on the heart.
5. Employed in the treatment of internal hemmorage, in inflammatory diseases, in
delirium tremens, in epilepsy, in acute mania and various other diseases
6. Digitalis has a commulative effect in the body, so the dose has to decided very
carefully.
1.1(Grecian Foxglove)
Consists of the dried leaves of Digitalis lanata J.F.Ehrh
Cons: Lanatoside A, B,C, and E
Uses;
1. Commercial source of digoxin
2. Employed in the treatment of auricular fibrillation and congestive heart failure
Adverse reaction:
1. Nausea
2. Vomiting
3. Slow pulse
4. Visual disturbance
5. Anorexia
6. Fainting
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III. SAPONIN GLYCOSIDES
Saponis are glycoside compounds often referred to as “Natural Detergent” because
of their foamy texture.
The aglycone is referred to as the sapogenin and steroid saponins are called
sarsaponins
Saponins are bitter and reduce the palatability of livestock feeds
7. QUILLAIA (syn: soap bark, quillary bark, panama wood, murillo bark, Cortex quillaiae).
From the inner dried bark of Quillaia saponaria Molina.
Cons: Quillaic acid
Saponin 10%
Calcium oxalate
Starch
Sucrose
Tannin
Quillaic acid (from hydrolysis of quillaia saponin)
Uses:
1. Quillaia bark is used as emulsifying agent, coal tar emulsion, cleaning industrial
equipment, washing delicate fabrics, to prepare tooth powders, tooth paste, hair
shampoos, hair tonics, tar solutions and metal polishes.
2. Added to topical preparation for skin disorder.
3. Protective agent for cracks, bruises, frostbite, and insect bite.
4. Diuretic
5. Cutaneous stimulant
6. expectorant
Caution: the drug is highly irritating and causes nausea on internal consumption
F-gitonin
Desglucolanatigonin
Gitonin
Uses:
1. The fruit has cooling, anti-inflammatory, antarthritic, diuretic, tonic, aphrodisiac
properties.
2. Used in building immune system, in painful micturition, calculus affection and
impotency.
3. Improves and prolong the duration of erection.
4. Exerts a stimulating effect on reproductary organ.
Smilax ornata
Uses:
1. Used in chronic skin disease, rheumatism, passive dropsy, and in syphilis.
IV. CYANOGENIC GLYCOSIDE
1. ALMOND – fixed oil obtained by the expression from the seeds of Prunus amygdalus,
var. dulcis (sweet almond), amara (bitter almond).
Uses:
1. Expressed almond oil is an emollient and an ingredient in cosmetic.
2. Almond oil is used as laxative, emollient in the preparation of toilet articles.
3. Vehicle for oily injections.
4. Volatile almond oil is flavoring agent.
2. WILD CHERRY BARK (syn: Virginian prune, black cherry, Virginian bark, cortex pruni).
Is the dried bark of Prunus serotina Ehrhart.
Cons: Prunasin
Scopoletin
Starch
Resin
Tannin
Gallic acid
Fatty matter
Lignin
Red coloring matter
Salt of calcium, potassium, and iron
Volatile oil
Uses:
1. Astringent tonic
2. Pectoral
3. Sedative
4. Expectorant
5. Treatment of bronchitis
6. Valuable in catarrah, whooping cough, and dyspepsia.
IV. ISOTHIOCYANATE GLYCOSIDE
V. FLAVONE GLYCOSIDE
Yellow pigment – distributed in higher plants:
Rutin, Quercitrin, hyperoside, diosmin (buchu leaf)
Hesperidin (citrus bioflavonoids – lemon and orange peel)
Vitexin (Carategus)
Uses:
1. Used as an antiasthmatic and bronchodilator.
2. Extract of the leaves containing selected constituent are used in improving
peripheral and cerebral circulation in those elderly with symptoms of loss of short-
term memory, hearing, and concentration.
3. Vertigo, headache, anxiety, and apathy are cured.
1. VISNAGA (syn: bishop’s flower, greater ammi, toothpick weed, Viznaga, Khaizaran,
khellakraut, khillah, picktooth)
Ammi visnaga Linn.
Cons: Khellin
Visnagin chief constituent
Khellol
Furanocoumarin compounds
Pyranocoumarin esters (visnadin, samidin, and dihydrosamidin)
Fixed oil
Protein
Uses:
1. Visnaga is an effective muscle relaxant
2. Alleviate the excruciating pain of the kidney stones.
3. Khellin is used in the treatment of asthma.
4. Seeds are diuretic, antiasthmatic, and lithontripic.
5. The seed have a strong antispasmodic action on the smaller bronchial muscle,
urinary and blood vessel without affecting blood pressure.
Ammi majus
Cons: Xanthotoxin 0.4-1.9 %
Imperatorin
Bergapten
Isopimpilin
Furanocoumarins
Uses:
1. furanocoumarin which stimulate pigment production in the skin that is exposed to
sunlight, thus it is used in the treatment of vitiligo (piebald skin), and psoriasis.
Uses:
1. The fruits are aphrodisiac, antibacterial, and tonic to the genital organ.
2. The seed is anthelmintic, antibacterial, aphrodisiac, astringent, cytotoxic,
diaphoretic, diuretic, stimulant, stomachic, and tonic.
3. Used in the treatment of febrile disease, premature ejaculation, impotence, lower
back pain, frequent urination, incontinence, and bed wetting.
4. Externally, used for various skin ailments such leprosy, leukoderma, and hair loss.
Psoralea corylifolia
Cons: Vanillin
Glucovanillin (vanilloside) green vanilla
Glucovallinic alcohol
During curing: glucovannilic alcohol (hydrolysis yield glucose and vanillic alcohol)
Vallinic alcohol (oxidation) = vanillic aldehyde (vanillin)
Glucovanillin hydrolysis = yield glucose and vanillin.
Relative contents: anisyl alcohol, anisaldehyde, anisyl ethers, anisic acid ester, piperonal,
and p-hydroxybenzoic acid, vitispiranes – add to the flavor of the pods.
Uses:
1. Vanilla pods are widely used in confectionary and in perfumery.
Uva-ursi
Cons:
Arbutin (in the leaves) gallic acid
Methyl arbutin ursolic acid
Quercetin α- amyrin
Ursone β-amyrin
Iriodoids terpenoids
Quinones
Tannin 6-10%
Uses:
1. The leaves have diuretic and astringent properties.
2. As infusion, used in urethritis and cystitis.
1. SOLANUM
It consists of the dried berries of Solanum khasianum C.B Clarke.
Solanum khasianum
Cons:
Steroidal glycoalkaloid (solasodine 3%)
Solakhasianin (rhamnose and galactose sugar component)
Greenish -yellow fixed oil 8-10%
Uses:
1. Solasodine is used as precursor for steroidal synthesis.
2. 16-dehydro-pregnenelone acetate is used as precursor for steroids
(corticosteroids, pregnane, and androstanes)- these are useful as sex hormones,
and oral contraceptive.
Gentiana lutea
Uses:
1. Use as herbal bitter in the treatment of digestive disorders.
2. Used to measure scientific basis for measuring bitterness (because it contain
the most bitter compound).
3. Useful in state of exhaustion from chronic illness, in all cases of debility,
weakness of the digestive system and lack of appetite.
4. Strengthen human system, stimulating the liver, gall bladder and digestive
system.
5. Excellent tonic to combine with a purgative in order to prevents it debilitating
effects.
6. Anthelmintic
7. Anti-inflammatory
8. Antiseptic
9. Emmenagogue
10. Febrifuge
11. Refrigerant
12. Stomachic
13. Taken internally in the treatment of liver complaints, indigestion, gastric
infection and anorexia.
Caution: it should not be prescribed for patients with gastric and duodenal ulcer.
2.PICRORHIZA (Syn: kami, kuru (hindi), katvee)
Consist of dried rhizome of Picrorhiza kurroa Royle ex Benth., cut into small pieces
and freed from attached rootlets.
Picrorhiza kurroa
Cons:
Picrorhizin (active constituent) on Apocynin
hydrolysis yield picrorhizetin and 6-feruioylcatalpol
dextrose. Vernicoside,
Kutkin (bitter principle) minecoside,
Picroside I, II, III picein,
D-mannitol androsin,
Vallinic acid β-D-6-cinnamoylglucose
Kurrin arvenin III
Kutkiol phenolic glycoside (picein and androsin)
Kutkisterol seven cucurbitacin glycoside
Uses:
1. Picrorhiza is bitter, cathartic, stomachic.
2. Used in fever and dyspepsiaand in purgative preparations.
3. Antiperiodic and cholagogue, febrifuge, and antimalarial.
4. Cured different types of jaundice.
5. Removes kidney stone
6. Emmenagogue
7. Emetic
8. Abortifacient
9. Antidote for dog bite.
10. Externally, used in skin disease.
11. Improves eye sight
12. Laxative in small doses
13. Cathartic in large doses
2. CHIRATA (syn: Indian gentian, Indian balmony, chirayta, Ophelia chirata, swertia
chirayita)
Consists of the entire herb of Swertia chirata Buch-Ham.
It contains not less than 1.3 % bitter constituent.
Cons:
Chiritin
Gentiopicrin
Amarogentin (phenol carboxylic acid ester of sweroside
, a substance related to gentiopicrin)
Ophelic acid (non crystalline bitter substance)
Gentainine
Gentiocrucine
Swertia chirata
Uses:
1. Ingredient in well known ayurvedic preparation mahasudarshan churna and
Sudarshan churna used successfully in chronic fever.
2. The whole plant is extremely bitter tonic digestive herb that lowers fevers and is
stimulant.
3. Beneficial effect on the liver, promoting the flow of bile.
4. Cures constipation
5. Treatment for dyspepsia
3. QUASSIA (syn: lignum quassiae, bitter wood, Jamaica quassia, bitter ash)
Is the dried wood of the stem of Aeschrion excelsa (Picroena excelsa Linld
or Picrasma excelsa (S.W) Planchon).
Picrasma excelsa
Cons:
1. Bitter amaroid compounds
Quassin
Isoquassin (picrasmin)
Neoquassin and 18-hydroxy quassin
Volatile oil
Gummy extractive pectin
Woody fiber
Tartrate and sulphate of lime
Chlorides of calcium and sodium
Salts (oxalate, and ammoniacal salt)
nitrate of potash
sulphate of soda)
Uses:
1. quassia wood is a pure bitter tonic and stomachic.
2. Vermicide and slight narcotic
3. It acts on flies and some of the higher animals as a narcotic poison.
4. Valuable remedy in convalescence, after acute disease and in debility and atonic
dyspepsia.
5. Antispasmodic in fever
6. Increase appetite (small doses)
Cons:
1. Kalmeghin (bitter crystalline diterpene lactone)
2. Andrgrapholide flavonoids and phenol
3. Lactones (andrographolide, 14-deoxy-11-oxo- andragrapholide, 14-deoxy-11, 12-
didehydroandrographolide, 14-deoxyandrographolide, and neoandrographolide)
4. The leaves contains (β-sitossterol glucoside, caffeic, chlorogenic, and dicaffeoyl-
quinic acid, carvacrol, eugenol,myristic acid, hentriacontane, tritriacontane, oroxylin
A, wogonin, andrograpanin, 14-deoxy-12-methoxyandrographolide, andrographidines
A-F, and stigmasterol.
Uses:
1. Febrifuge, tonic, alterative, anthelmintic, astringent, anodyne, alexipharmic
(antidote to poison), cholagogue (promotes discharge of bile) properties.
2. Useful in debility, cholera, diabetes, swelling, itches, consumption, influenza, piles,
gonorrhea, bronchitis, dysentery, dyspepsia, fever, and in weakness.
3. A decoction of the plant as a blood purifier and as cure for torphid (mentally and
physically inactive/lethargic), and jaundice.
4. The pills prepared from macerated leaves and certain spice (e. cardamom, clove,
cinnamon) are given for stomach ailments for infants.
Prepared by:
Beverly Joy O. Gadiano