Saponin Glycosides

- Foams upon shaking

o Large C atoms (lipophilic) H2O soluble sugars (hydrophobic/hydrophilic
asymmetry): Lowers surface tension in aqueous solution
- Bitter, acrid taste
- Sternutatory, irritating to the mucous membrane
- Hemolyze RBC (toxic), employed as fish poison
- Hydrolysis yields SAPOGENIN (aglycone)
- Isolated by crystallization upon acetylation rxn
- SAPOTOXINS poisonous saponins

GLYCYRRHIZA
Sc. Name: Glycyrrhiza glabra
Family: Fabaceae
Common Name: Licorice root, Spanish Licorice Russian Licorice, Sweet Root
Constituents: Glycryrrhizin (Glycyrrhizic acid)
- 50x sweeter than sucrose
- Hydrolysis yields Glycyrrhetic acid (Glycyrrhetinic acid)
+ Glucoronic acid
- increases fluid and sodium retention and promotes
Potassium depletion
Liquiritin
Stegmasterol
Aspargine
Flavonoid Glycosides
Uses: Demulcent
Expectorant
Flavoring
Anti-inflammatory: dermatological prep

GINSENG
Sc. Name: Panax ginseng Panax quinquefolius
Family: Araliaceae
Common Name: American ginseng
Constituents: Ginsenosides
Panoxides
Chikusetsusaponins
Uses: Tonic
Stimulant
Diuretic
Carminative
Adaptogenic
Aphrodisiac and performance/endurance enhancer
Cyanogenic Glycosides
- Hydrolysis: Hydrocyanic acid catalyzed by β-glucosidases
- Der. Of mandelonitrile (benzaldehyde + cyanohydrin)
- Represented by amygdalin (bitter almonds, kernels of apricot, cherry, peaches
plum)
- Amygdalin & prunasin: (R)-mandelonitrile (AGLYCONE)
- Sambucus nigra: (S)-mandelonitrile (AGLYCONE)
- CYANOGENISIS: chemical defense response to organisms damaging the plant
tissue when feeding on intact plant part or attacking through the injury site
- Uses: Flavoring agent
Antineoplastic: Vit. B17 Laetrile
Control of sickle cell anemia

WILD CHERRY
Sc. Name: Prunus serotina
Family: Rosaceace
Common Name: Prunus virginiana, wild black cherry
Constituents: Prunasin: D-mandelonitrile glucoside
Prunase
p-Coumaric acid
Trimethyl gallic acid
Scopoletin
Uses: Flavorant
Sedative expectorant

APRICOT PITS
Sc. Name: Prunus
Family: Rosaceae
Common Name: apricot pits
Constituents: Emulsin
 Hydrolyzes releasing toxic cyanide
 Inactivated by heating
Amygdalin
Uses: Source of laetrile/amygdalin
- MOA: selective release of cyanide or toxic cyanide containing
compounds in the cancer cells without injury to the other normal
cell or tissue
Isothiocyanate Glycosides
- GLUCOSINOLATES (glycoside)
 Represents bound toxins
 Hydrolysis by myrosinase: D-glucose & labile aglycone ››› isothiocyanate
 Sulfur atom conjugated to glucose (S-glycoside) & a 2nd sulfur in a
sulfonated oxime grouping
- Aglycones present are alipathic or aromatic

BLACK MUSTARD
Sc. Name: Brassica nigra
Family: Brasiccaceae
Common Name: Sinapsis nigra, brown mustard
Constituents: Sinigrin
Volatile Mustard oil: allyl isothocyanate
Uses: Condiment
Irritant
Emetic
Rubefacient & vesicant

WHITE MUSTARD
Sc. Name: Brassica alba
Family: Brasiccaceae
Common Name: white mustard
Constituents: Sinalbin
 Hydrolysis with myrosinase: p-hydroxybenzyl isothiocyanate
Acrinyl isothiocyanate
Uses: Condiment
Irritant
Emetic
Rubefacient & vesicant

GARLIC
Sc. Name: Allium sativum
Family: Liliaceae
Common Name: garlic
Constituents: Allicin (diallyl disulfinate)
 Alliin + alliinase
 Characteristic odor and flavor
 Decompose in the presence of air and H2O: diallyl dislufie,
diallyl trisulfide
Uses: Antibacterial acivity
Antihyperlipidemic activity
Blood fibrinolytic activity and platelet aggregation
Antithrombotic
Alcohol Glycoside

SALICIN
Sc. Name: Salix purpurea, Salix fragalis
Family: Salicaceae
Common Name: Willow tree
Constituents: Salicin
 Hydrolysis by emulsion: D-glucose & saligenin (salicyl
alcohol)
 Axn resembles salicylic acid
Populin (benzoylsalicin)
Uses: Antirheumatic properties

Aldehyde Glycoside

VANILLA
Sc. Name: Vanilla planifolia
Family: Orchidaceae
Common Name: Mexican Vanilla
Bourbon Vanilla
Tahiti Vanilla
Constituents: Glucovanillin (avenein)
 Hydrolyzed: Glucose + Vanillin
Glucovanillic acid
 Hydrolyzed: Glucose + Vanillic alcohol ›› Oxidized: Vanillic
aldehyde (Vanillin)
Vanillin
 4-hyrdoxy-3-methoxybenaldehyde
 Methylprocatechuic aldehyde
 Other sources:
 Coniferin (cambium sap from pine tree)
 Eugenol (clove oil)
 Lignin (primary source of commercial vanilla)
 Ethyl vanillin (synthetic analog - lactone)
 Slightly soluble to H2O & glycerin
 Freely soluble to alcohol, chloroform, ether
 Fine, white to slightly yellow needle-like crystals that have an
odor and taste resembling vanilla
Uses: Flavoring for cocoa
Flavoring agent & Pharmaceutic aide
Phenol Glycoside
- Arbutin
 Hydrolysis: hydroquinone + glucose
- Hesperidin
 Various citrus fruits
- Phloridzin
 Rosaceous palnts
- Baptisin
 Baptisia
- Iridin
 Iris species

UVA URSI
Sc. Name: Arctostaphylos uva-ursi
Family: Ericaceae
Common Name: bearberry
Constituents: Arbutin
Corilagin
Pyroside
Quercitin
Gallic acid
Egalic acid
Ursolic acid
Uses: Antiseptic
Astringent