GLYCOSIDES & TANNINS Flashcards by Mac Asprec

Glycosides occurs in what form in plants

Beta form

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Components of glycosides and activity

Glycone : inactive form as vehicle

Aglycone : active form, genin basis for classification

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Unsaturated steroidal aglycone tests:

Liebermann-Burchard : + blue/green, yellow for saturated

Salkowski’s test : +red/violet

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2 deoxy sugar glycone test

Keller Killani : +reddish brown

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Bufadienolides are

Inactive & Rare

C-24 doubly unsaturated 6 membered lactone ring

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Cardenolides

Common & active

C-23 a & b unsaturdated 5-membered lactone ring

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Cardiac glycoside from digitalis

Digoxin - water

Digitoxin - lipid

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Aka Lily of the Valley

Source of convallatoxin

Convallaria

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Aka dogbane

Source of cymarine

Apocynum

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Aka xmas rose

Source of hellebrin

Black hellebore

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Aka pheasant’s eye

Source of adonitoxin

Adobis

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3 components of strophantus

K strophantin (good)
G strophantin (bad)
Oubain (toxic)

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Glycosides which contain anthracene: aglycone

Anthraquinone glycosides

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Id test for anthraquinone glycosides and derivative color

Borntranger’s Test

+ orange

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Constituents of cascara sagrada (rhamnus purshianus)

Cascarosides A&B - optical isomer of barbaloin

Cascarosides C&D - optical isomer of chrysaloin

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Purified mix of anthranil & glycoside

Lane’s pill or casanthol

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Constituents of aloe used for burn & cathartic

Aloe emodin & barbaloins

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Therapeutic rhubarb or Chinese rhubarb

Rheum officinale

Rheum palmatum

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Ornamental or Indian/Himalayan rhubarb

Rheum emodi

Rheum webbianum

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Derivative color of senna

Constituents

Blue green

Sennosides A,B,C,D

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Only anthraquinone glycoside not used as cathartic instead as keratolytic

Chrysarobin

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Used to extract chrysarobin from Andira araroba

Hot benzene

Forms 2cm froth upon shaking, sternutatory, fish poison

Saponins

Used to increase beer foam

Glycyrrhiza or licorice

Contains a diosgenin for glucocorticoid

Dioscorea spiculiflora

Contains steroidal diosgenin

Dioscorea floribunda

Contains amygdalin (water + amygdalase)

Cyanophoic or Cyanogenic Glycosides

Mixture of amygdalase + prunase

Emulsin

Id test for cyanogenic glycosides

Guignard's test + brick red

Contains laetrile or vit b17 for sickle cell anemia

Bitter almond or prunus amygdalus

Gluconapinisothiocyanate glycosides came from

Rapeseed (brassica napus)

Gluconasturtiin isothiocyanate glycoside came from

Watercress (nastatium officinale)

Test for isothiocyanate glycoside

Fehling's test + blood red (non volatile) Odor test: mustard smell (volatile) Garlic (allicin)

Sinigrin source

Brassica nigra or black mustard

Sinalbin source

Brassica alba or white mustard

Flavonol glycosides from citrus fruits and soya

Rutin & Hesperidin - vit P permeability factors for capillary bleeding

Flavonol glycoside for common cold

Hesperitin, Diosmin & Naringen

A hepatoprotective flavonol glycoside from milk thistle

Silibinin & silymarin

Alcohol glycoside from salix purpurea and salix fragilis

Salicin

Tests for alcohol glycoside

Fehling's +red Nessler's + gray Tollen's + silvermirror Schiff's + recolorization

Aldehyde glycoside from vanilla planifolia

Vanillin

Phenol glycoside from arctostaphylos urva ursi as astringen & diuretic

Arbutin

Contains uroshiol which cause contact dermatitis

Poison ivy or poison oak

A lactone glycoside from dried insect Catharis besicatoria or Russian Fly

Cantharides

Causes priaprism or sustained erection

Cantharides or cantharidin

Photosynthesizing furocoumarins from Bishop's flower (ammi majus)

Psoralens (lactone glycoside)

Polypeptides unable to crystallize | Protein precipitant found in leaves or barks

Tannins

Local sources of tannins

Guava, Kamachile (pithecolobium dulce) and duhat (syzigium cumini)

+ in Goldbeater's test

True Tannins

Readily hydrolyzed tannins that yield phenolic acid and sugar Leather is bloom Blue black FeCl test - Bromine Test

Hydrolyzable Tannins

Aka condensed tannin From condensation of catechin and leucocyanidin Polymerize to phlobatannileather is tanners red Green black FeCl + Bromine Test

Non-hydrolyzable tannins

Negative Goldbeater's test | Ex. are hamamelis leaf, nutgall & japanese gall

Pseudotannins

Obtained from plant Quercus infectoria when insect Cynips tinctoria bores hole & lays ovum

Gallic + Ellagic = Tannic Acid from Nutgall (GET)

Component of Japanese/Chonese gall

Gallic acid