Exp 5 Flashcards by Nerd Lab

“sugar ethers”; a compound that yield 1 or more sugar and a non-sugar component among the products of hydrolysis

Glycosides

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functions of glycosides

regulatory, productive, & sanitary compounds
cardiac glycosides, laxatives, local irritants, analgesics, etc

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two components of glycosides

• glycone
• aglycone (genins)

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what are the components of glycone?

• sugar component
• common denominator
• inactive

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what are the components of aglycone?

• non-sugar component
• basis of classification
• active

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if it’s glucose, it’s called?

glucoside

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if it’s fructose, it’s called?

fructoside

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if it’s galactose, it’s called?

galactoside

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if it’s glucoronic acid, it’s called?

glucoronide

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four classifications based on glycosidic bond

C, O, N, S

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classification based on aglycone portion

alcohol, aldehyde, anthraquinone, chromone, coumarin, cyanogenic, flavonoid, iridoid, isothiocyanate, phenol, saponin, steroidal, & steviol

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the aglycone portion is an alcohol derivative

alcohol glycosides

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source of alcohol glycosides

willow bark (salix purpurea, s. fragilis)

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the aglycone portion is an aldehyde derivative

aldehyde glycosides

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source of aldehyde glycosides

vanilla (vanilla planifolia, v. tahitensis)

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• largest group of naturally occuring quinone pigments
• dyes, cathartics, stimulant laxative (habit-forming

anthraquine glycosides

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• derivatives are often orange-red compounds that are soluble in hot water and in dilute alcohol
• gives a characteristic red, violet, green, or purple color with a base

anthraquinone glycosides

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tests for anthraquinone

bontrager’s test & modified bontrager’s test

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result of bontrager’s test

red coloration in the lower ammoniacal layer

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result of modified bontrager’s test

pink color

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sources of anthraquinone

• cascara sagrada
• frangula
• aloe vera
• rhubarb
• indian rhubarb
• senna
• chrysarobin

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the aglycone portion are derivative of benzo-δ-pyrone nucleus

chromone glycosides

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sources of chromone glycosides

• hypericum erectum
• japanese eurya (eurya japonica)
• cassia multijuga

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the aglycone portion are derivative of benzo-α-pyrone nucleus

coumarin glycosides

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sources of coumarin glycosides

• tonka bean (dipteryx odorata) • meadowsweet (filipendula ulmaria) • sweet clover (melilotus officinalis) • vanilla grass (anthoxanthum odoratum)

• yields hydrocyanic acid upon hydrolysis • often found in legumes, root crops, and grasses • usually in plants together with hydrolytic enzymes

cyanogenic glycosides

most cyanogenic glycosides are lost after plant harvest due to what?

spontaneous hydrolysis

laetrile, thought to have anti-tumor properties

amygdalin

test for cyanogenic glycosides

guignard’s test

appearance of various shades of red within 15 mins when the tube is warmed (yellow to brick red)

guignard’s test

sources of cyanogenic glycosides

wild cherry (prunus serotina) apricot (prunus armeniaca) almond (prunus amygdalus) cassava (manihot esculenta)

• phenolic plant pigments containing a benzo-y-pyrone nucleus • anthocyanins, leucoanthocyanins, catechins, aurones, calchones • anti-viral, anti-fungal, anti-inflammatory, and cytotoxic

flavonoid glycosides

anthocyanins on hydrolysis yield sugars and colored aglycones

anthocyanidins

the aglycone of leucoanthocyanins

leucoanthocyanidin

test for flavonoid

bate-smith & metcalf test, wilstatter “cyanidin” test

result of bate-smith & metcalf test

strong red or violet color

result wilstatter “cyanidin” test

colors range from orange to red, to crimson and magenta, and occassionaly to green or blue

examples of flavonoid glycosides

• hesperidin • naringin • rutin • quercitin

the aglycone portion is an iridoid, usually bound to the glycone portion glucose

iridoid glycosides

sources of iridoid glycosides

• asterids (aucuba japonica, eucommia ulmoides) - aucubin • catalpa (catalpa bignonioides, c. speciosa) - catalpol

• derived from the hydrolysis of glucosinolates • anti-cancer

isothiocyanate glycosides

sulphur-containing compounds found in cruciferous plants

glucosinolates

sources of isothiocyanate glycosides

• black mustard (brassica nigra) • white mustard (brassica alba)

the aglycone portion is a phenol group

phenol glycosides

source of phenol glycosides

bearberry (arctostaphylos uva-ursi)

• cardiac glycoside • prominent effect on the heart muscle

steroidal glycosides

cyclopentanoperhydrophenanthrene nucleus

steroidal nucleus

cyclopentanoperhydrophenanthrene

steroidal skeleton

more common, has optimum activity, C-23, 5-membered lactone ring

cardenolide

less common, less activity, C-24, 6-membered lactone ring

bufadienolide

test for steroidal

• keller-killiani test • liebermann-burchard test • kedde’s test

test for 2-deoxysugars; reddish-brown which may turn blue or purple

keller-killiani test

test for unsaturated steroids and triterpenes; colors range from blue to green, red, pink, purple, or violet

liebermann-burchard test

test for unsaturated lactones; blue-violet color

kedde’s test

sources of steroidal

foxglove, grecian foxglove, convallaria, pheasant’s eye, black hellebore, dogbane, adelfa, strophantus, ouabain, squill, red squill

• the aglycone portion is a steviol • natural sweeteners, as sub for sugar (40-300 times sweeter than sucrose)

steviol glycosides

source of steviol

stevia (stevia rebaudiana)

harmless when taken orally

saponins

two types of saponins

• steroidal (monocot families; dioscoreaceae) • triterpenoidal (dicot; agavaceae)

steroidal/triterpenoid glycosides characterized by their ability to froth when agitated

saponin used as detergent

exert a powerful hemolytic action on RBCs and are highly toxic when injected into the bloodstream

saponin used as fish poison

contains sapotoxin which is a poisonous saponin

saponin with interesting spermicidal & molluscicidal activity

used to produce acid saponin if present are precipitated as lead salts

neutral lead acetate

used to precipitate neutral saponin

basic lead acetate

used to decompose lead precipitate

hydrogen sulfide

properties of saponin glycoside

• amorphous; soluble (H2O & alc) • persistent froth • hemolysis of RBC’s • bitter, acrid taste

test for saponins

• froth test • agar cup hemolytic test • fehling’s test • baryta water test • lead acetate test

extract used for saponins physical test

gugo extract

color, odor, and taste of gugo extract

• golden yellow to orange • odorless • slightly bitter, acrid

sources of saponins

• licorice (glycyrrhiza glabra) • yam (dioscorea floribuna, d. alata) • ginseng (panax ginseng, p. quinquefolius) • gugo (entada phaseoloides)

philippine sources

adelfa, akapulko, campanero, campanilla, gugo, kalumbibit, lukban, maguey, pistula, sabila

official usp 24/nf 19 drugs

7 usp 24 4 nf 19