PCOG pt. 3

Glycosides

• mixed acetals

• yield one or more sugars among the product of hydrolysis

• suffix (-IN)

• Aglycone, aglycon/genin (no sugar)

• Glycone (w/ sugar)

What are the components of glycosides?

• regulatory

• protective

• sanitary functions of plants

• therapeutic agents

What are the importance of glycosides?

• Cardioactive steroid group

• Anthraquinone group

• Saponin group

• Cyanophore group

• Glucosinolate/Isothiocyanate group

• Flavonol group

• Alcohol group

• Aldehyde group

• Phenol group

• Lactone

What are the classifications of the glycosides based on the chemical nature of the aglycone group?

• froth test

• hemolysis test

• capillary tube test

Identification tests for saponin glycosides

• borntrager’s test

Identification tests for anthraquinone glycosides

• guignard’s test

Identification tests for cyanogenic glycosides

Cardiac glycosides

• related to steroids, CPPP nucleus

• sugar component is attached on the 3 position of the CPPP nucleus

• inotropic agents (changes heartrate)

cyclopentanoperhydrophenanthrene

meaning of CPPP

1. cardenolides

2. bufadienolides

the 2 aglycone in cardiac glycosides

Cardenolides

5-membered ring

Bufadienolides

• 6-membered ring

• discovered from bufalin isolated from the skin of toad

• + digoxin

• - betablockers

2 types of inotropic agents

• foxglove (D. purpurea)

• Grecian foxglove (D. lanata) Scrophulariaceae

synonyms of digitalis and its botanical sources

• digitoxin

• gitaloxin

• gitoxin

Constituents of D. purpurea (foxglove)

D. purpurea (foxglove)

• most lipid soluble

• digoxin

• desacetyl lanatoside (deslanoside)

Constituents of D. lanata (grecian foxglove)

D. lanata (grecian foxglove)

• polar, short-acting used for rapid digitalization

Lily of the Valley (Cobvallaria majalis)

synonym of convallaria and its botanical source

Convallotoxin

what is the constituent of convallaria (lily of the valley)

Black indian hemp, Dog bane (Apocynum cannabinum)

synonym of apocynum and its botanical source

cymarin

what is the constituent of apocynum

pheasant’s eye (Adonis vernalis)

synonym of adonis and its botanical source

• adonitoxin

• cymarin

• k-strophantin

what is the constituent of adonis

night blooming cereus (Selenicereus grandiflorus)

synonym of cactus grandiflorus and its botanical source

Christmas rose (Helleborus niger)

synonym of black hellebore and its botanical source

hellebrin

what is the constituent of black hellebore

• black

• green and white

3 varieties of black hellebore

black hellebore

glycosidal, cardiac stimulant (inotropic)

green and white hellebore

alkaloidal, cardiac depressant

S. kombe, S hispidus

botanical source of strophanthus

• K. strophantoside

• G. strophantin (ouabain)

what is the constituent of strophanthus

strophanthus

3rd most important glycoside available in the market

squill bulb (Urginea maritima)

synonym of squill and its botanical source

• scillaren-a, convert to scillarenin which is more active

what is constituents of squill

squill

• used as expectorant and has a red variety (rodenticide)

Oleander (Nerium oleander)

synonym of adelfa and its botanical source

oleandrin

what is constituents of adelfa

adelfa

genocide in sri lanka

Anthraquinone glycosides

• related to anthracene

• used as stimulant cathartics

• from Penicillium islandicum

• orange red compounds

• upon hydrolysis, the aglycone portion consists of a di- tri- or tetrahydroxyanthraquinone

borntrager test

what is the identification test for anthraquinone glycosides

Schonteten’s test

is often used for anthranols (green fluorescence)

Sacred bark (Rhamnus purshiana)

what is the synonym and botanical source of cascara sagrada

cascara sagrada (sacred bark)

found in lane’s pills

• casanthranol

• emodin - cascarosides

  • cascarosides A&B

  • cascarosides C&D

what is the constituents of cascara sagrada

• normal O-glycosides

• aloinlike C-glycosides

what are the two types of anthracene compounds

cascarosides A&B

based on optical isomers of barbaloin

cascarosides C&D

based on optical isomers of chrysaloin

normal O-glycosides

based on emodin (about 10-20%)

aloinlike C-glycosides

• about 80-90%

• eg. barbaloin and deoxybarbaloin

buckthorn bark (Rhamnus frangula)

what is the synonym and botanical source of frangula

frangulins A and B

what is the constituents of frangula

frangula

component of OTC product MOVICOL (also contains karaya)

sabila

what is the synonym of aloes (curacao aloe, cape aloe)

• aloin A - barbaloin

• aloin B - isobarbaloin

what are the constituents of aloes

aloes (curacao aloe, cape aloe)

• pharmaceutical aid for compound benzoin tincture

• cathartic

Aloe vera gel

• for burns, abrasions, and skin irritation, inflammation, alopecia

• Rheum

• Chinese rhubarb

• Himalayan rhubarb

• Indian rhubarb

synonyms of rhubarb

rheum officinale

what is the botanical source of rheum

rheum palmatum

what is the botanical source of chinese rhubarb

rheum emodi

what is the botanical source of himalayan rhubarb

rheum webbianum

what is the botanical source of indian rhubarb

rhein anthrones

constituent of rhubarb

senna

cultivated on wet lands resembling rice paddies

blue green senna

best grade senna

yellowish senna

poorest senna

• Alexandria senna

• Tinevelly senna

synonyms of senna

cassia acutifolia

botanical source of alexandria senna

cassia angustifoli

botanical source of tinevelly senna

• aloe-emodin/rhein sennosides

constituents of senna

sennosides A and B

a pair of stereoisomers whose aglycones are rhein dianthrone

sennosides C and D

dimeric aglycone

Chrysarobin

• is a mixture of neutral principles obtained from goa powder (Abdira araroba)

• not employed as cathartic because it is too irritating to use

• used as keratolytic - psoriasis, trichophytosis and chronic eczema

hot benzene

used to extract chrysarobin

danthron/chrysarin (1,8-dihydroxyanthraquinone)

• used as cathartic

• is an important intermediate in the manufacture of anthralin and of alizarin and indanthrene dyestuffs

froth test

form colloidal solutions in water that foam upon shaking

saponin glycosides

• they have bitter, acrid taste and drugs containing them are usually sternutatory and otherwise irritating to the mucous membrane

• widely distributed in the plant kingdom

• toxic to insects and mollusks

• used to control schistosomiasis

• fish poison

• source of anti-inflammatory agents

hemolysis test

destroy red blood cells by hemolysis and are toxic especially to cold-blooded animals

• steroids

• triterpenoids

2 types of saponin

diosgenin and botogenin

the most important plant steroids for the partial synthesis of steroid hormones - from the genus of dioscorea

• hecogenin

• manogenin

• gitogenin

from species of Agave

sitosterol

from crude vegetable oils

licorice root

synonyms of glycyrrhiza

glycyrrhiza

• mask the taste of bitter drugs

• increase foaminess in beer

• used in peptic ulcer and addison;’s disease

• spanish licorice

• russian licorice

botanical sources of glycyrrhiza

glycyrrhizin (glycyrrhizic acid)

• 50 times as sweet as sugar

• used to increase fluid and sodium retention and promotes potassium depletion

• CI: patients with cardiac failure and hypertension

glycyrrhetic acid

• aglycone portion of glycyrrhizin

• anti-inflammatory agent

mexican yam (D. floribunda/D. spiculiflora)

synonyms of dioscorea

• dioscin → diosgenin

• botogenen and diosgenin

constituents of dioscorea

dioscorea

• best source of steroids

• major precursor of glucocorticoids, oral contraceptives and sex hormones

american ginseng (Panax ginseng/Panax quinquefolius)

synonyms of ginseng

ginseng

• tonic, stimulant, diuretic, and carminative properties

• performance and endurance enhancer

• it is used in the tx of anemia, diabetes, insomnia, nuerasthenia, gastritis, and sexual impotence (aphrodisiac)

• ginsenosides

• panaxosides

• chikusetsusaponins

• ginsenoside Rg1

constituents of ginseng

Ginsenoside Rg1

one of the major saponins

Psidium guajava

vaginal wash after giving birth and as antibacterial agent

Lupulin

used in the manufacture of beer

• humulone (a-acids)

• lupulone (b-acids)

main compounds responsible for the bitterness of lupulin

agave

molluscicide

acid saponin

type of saponin glycoside with the pentacyclic triterpenoidal aglycone is commonly isolated in dicotyledonous plants

Cyanogenic glycosides

• glycosides yielding hydrocyanic acid

• b-glucosidases

• derivatives of mandelonitrile

• detected by guignard test

• enzyme: emulsin