MODULE 2: GLYCOSIDES

GLYCOSIDES

Acetals in which the OH group of the sugar portion is condensed with the OH group of the non-sugar portion.

  • GLYCONE: SUGAR, INACTIVE

  • AGLYCONE / GENIN: NON-SUGAR, ACTIVE

  • Linked by a sugar-ether bond.

TEST FOR CARDIAC GLYCOSIDES

LIEBERMANN-BURCHARD TEST

  • Unsaturated steroidal glycone

  • positive result: BLUE-GREEN COMPLEX

SALKOWSKI’S TEST

  • Unsaturated steroidal glycone

  • positive result: RED COLOR AT THE JUNCTION

KELLER-KILLANI TEST

  • 2-deoxysugar (glycone)

  • positive result: REDDISH BROWN


CARDIAC GLYCOSIDES

GRECIAN FOXGLOVE (Digitalis lanata)

FOXGLOVE (Digitalis purpurea)

Active Constituent:

  • DIGITALIS - WATER SOLUBLE, LESS TOXIC

  • DIGITOXIN - LIPID SOLUBLE, MORE SOLUBLE


CONVALLARIA / LILY OF THE VALLEY (Convallaria majalis)

A.C: CONVALLOTOXIN


BLACK HELLEBORE / CHRISTMAS ROSE (Helleborus niger)

A.C:

  • HELLEBRIN - Cardiac stimulant


ADONIS / PHEASANT’S EYE (Adonis vernalis)

A.C: ADONITOXIN


STROPHANTUS (Strophanthus kombe)

A.C:

  • K-STROPHANTHIN

  • G-STROPHANTHIN (OUABAIN) - Toxic Form


OLEANDER (Nerium oleander)

A.C: OLEANDRIN


SQUILL (Urginea maritima)

A.C:

  • SCILLARENIN - only bufadienolide

  • should not contain the RED MOIETY (very toxic)


ANTRAQUINONE GLYCOSIDES]

CASACARA SAGRADA / SACRED BARK (Rhamnus purshianus)

A.C:

Cascaroides

  • AB: Optical isomer of BARBALOIN

  • CD: optical isomer of CHRYSAROBIN

  • Barked aged for 1 year - treated with MgO to mask bitter taste.

USE: as CATHARTIC

  • LANE’S PILL - contains casanthrol which is a purified mixture of anthranol glycosides)


FRANGULA / BACKTHORN BARK (Rhamus frangula)

A.C:

  • FRANGULIN

  • MOVICOL - KARAYA + FRANGULA (cathartic)


ALOE

  • Curacao – Aloe barbadensis, A. vera

  • Cape – A. spicata, A. Ferox

A.C: BARBALOIN

  • Management of BURN WOUNDS

  • Moisturizer

  • Component of CBT (compound benzo tincture)


RHUBARB

  • Chinese: Rheum officinale; R. palmatum

  • Indian/ Himalayan: R. emodi / R. webbianum

A.C: RHEIN ANTHRONES

  • USED AS CATHARTIC


SENNA

  • Tinnevelly – Cassia angustifolia

  • Alexandria – Cassia acutifolia

A.C: SENNOSIDES A & B

  • TINNEVELLY - full leaves are used

  • ALEXANDRIA - broken leaves are used

  • Cultivated in wet lands resembling rice paddies

QUALITY:

  • EMERALD GREEN - BEST

  • YELLOW GREEN - WORST

  • More potent than CASACARA


GOA POWDER (Andira araroba)

A.C: CHRYSAROBIN

  • Not cathartic but a KERATOLYTIC

  • Very irritating to mucous membranes

  • extracted using HOT BENZENE


SAPONIN GLYCOSIDES

LICORICE (Glycyrrhiza glabra)

A.C:

GLYCYRRHIZIN L GLYCYRRHIZIC ACID - 50x as sweet as sugar, can mask bitterness of QUININE.

USES:

  • Expectorant, demulcent

  • Mask the bitterness of drugs

  • Increase foaminess of beer

  • Imparts bitter taste to root beer

  • Treatment of ADDISON’S & PEPTIC ULCER DISEASE

C/I: CHF and HTN > Promotes sodium and water retention - increase BP


DIOSCOREA / MEXICAN YAM

  • Dioscorea floribunda

  • Dioscorea spiculifora

A.C:

  • DIOSGENIN

  • BOTOGENIN

  • D.FLORILAMDA (best source)

  • Major precursor for STEROID SYNTHESIS (Glucocorticoids)


GINSENG

  • Asian – Panax ginseng

  • American – Panax quinquefolius

A.C:

  • Panaxosides

  • Ginsenosides

  • Chikusetsusaponins

USES:

  • APHRODISIAS

  • ADAPTOGEN

  • TONIC

C/I: ASPIRIN = increase the risk of BLEEDING.


CYANOGENIC GLYCOSIDES

  • ID Test: GUIGNARD TEST / PRUSSIC ACID TEST = (+) various shades of RED.

  • Laetrile aka VITAMIN B17 – was used for the Treatment of SICKLE CELL ANEMIA. (banned by US FDA)

  • Enzymes: Amygdalase + Prunase = EMULSIN

PLANT

  • BITTER ALMOND (Prunus amygdalus); AC: AMYGDALIN


  • APRICOT (Prunus armeniaca); AC: PRUNASIN


  • WILD CHERRY (Prunus serotina); AC: PRUNASIN


  • PEACH (Prunus persica); AC: PRUNASIN


  • CASSAVA (Mannihot esculenta); AC: MANNIHOTOXIN


  • FLAX (Linum usitatissimum); AC: LINMARIN


ISOTHIOCYANATE GLYCOSIDES

BLACK MUSTARD (Sinapis nigra)

  • Brassica nigra

  • SINIGRIN

  • ALYL ISOTHIOCYANATE - MUSTARD VOLATILE OIL

WHITE MUSTARD (Sinapis nigra)

  • Brassica alba

  • SINALBIN

  • ACRINYL ISOTHIOCYANATE - PUNGENT OIL

RAPESEED

  • Brassica napus

  • GLUCONAPIN


FLAVONOL GLYCOSIDES

FLAVONOIDS

  • RUTIN, HEPERIDIN

  • VITAMIN P - Treatment of capillary bleeding and fragility

  • HESPIRITIN, DIORMIN, NARINGEN - treatment for common cold symptoms.

  • RUTIN, QUERCITIN - yellow pigment.

MILK THISTLE (Silybum marianum)

A.C: SILYMARIN

  • HEPATOPROTECTIVE

GINGKO (Gingko biloba)

A.C: GINKGOLIDES, BILOLABIDES

  • Memory enhancement


ALCOHOL GLYCOSIDES

WILLOW BARK (Salix purpurea / Salix fragilis)

A.C: SALICIN — SALIGENIN

USES:

  • ANTIRHEUMATIC, ANTI-INFLAMMATORY

  • Hydrolyzed to saligenin (salicyl alcohol) and D-glucose by emulsin.


ALDEHYDE GLYCOSIDES

VANILLA (Vanilla plantifolia)

A.C: VANILLIN

  • Used as flavorant

  • SWEATING PROCESS - vanilla pods are sun-dried during the day; wrapped in a woolen cloths at night.

PHENOL GLYCOSIDES

UVA URSI / BEARBERRY (Arcotostaphylos uva ursi)

AC: ARBUTIN

  • Antiseptic and astringent

  • Other uses: Mild diuretic (present in teas)

POISON IVY (Rhus radicans)

POISON OAK (R. toxicodendron)

AC: UROSHIOL

  • Type 4 hypersensitivity

  • contact dermatitis


LACTONE GLYCOSIDES

TONKA BEANS (Dipteryx odorata)

AC: COUMARIN (orthohydroxycinnamic acid)

  • Fragrant odor, bitter aromatic and burning taste

  • Use: Flavoring agent; Anticoagulant (precursor of Warfarin)


YELLOW SWEET CLOVER

AC: DICUMAROL - bishydroxycoumarin


CANTHARIDES (Cantharis vesicatoria)

AC: CANTHARIDIN

  • Uses: Irritant, Vesicant, Aphrodisiac, Wart-removal


BISHOP FLOWERS (Ammi majus)

AC: PSORALENS

  • Photosensitizing furocoumarins

  • Methoxsalen – repigmentation in vitiligo

  • Trioxsalen – synthetic furocoumarin