Sei sulla pagina 1di 9

GLYCOSIDES

Sugar ethers; heteropolysaccharides


Compounds that yield one or more sugars among the
products of hydrolysis
Both and glycosides are possible; only form
occurs in plants ADONIS / Pheasants eye
1. Aglycone/Genin portion non-sugar portion Adonis vernalis
2. Glycone portion sugar portion Constituents: adonitoxin, cymarin, K-
CLASSIFICATION BASED ON AGLYCONE COMPONENTS strophanthin
CONVALLARIA / Lily-of-the-valley Root
CARDIAC GLYCOSIDES Rhizome and root of Convallaria majalis
Have specific action on the cardiac tissues; they Constituents: convallotoxin
increase force of systolic contraction CACTUS GRANDIFLORUS / Night-blooming cereus
AGLYCONES: cardenolide, bufadienolide (scillarenin) Stem of Selenicereus grandiflorus
Derived from C21 steroid BLACK HELLEBORE / Christmas Rose
CPPP nucleus (cyclopentanoperhyrophenanthrin) (bufadienolide)
Rhizome and root of Helleborus niger,
Inhibit Na/K ATPase, thereby increasing the Ca2+ inside
Ranunculaceae
the heart muscles ( + inotropic effect )
Constituents: hellebrin; helleborin
Deoxysugars at C3
Use: Abortifacient, cardiotonic
Green Hellebore: Cardiac Depressant
APOCYNUM / Black Indian Hemp / Dogbane /
Canadian Hemp
Rhizome and root of Apocynum canabinum
Constituents: cymarin

Strophantus
Dried, ripe seed of Strophantus kombe
Preparation of arrow poisons (Africans)
Constituents: K-strophanthin
Strophantus gratus: has ouabain (G-
strophanthin)
SQUILL / Squill bulb (bufadienolide)
Dried sliced bulb of the white variety of
Urginea maritama, Liliaceae
Constituents: scillaren A
DACCBASSO (Digitalis, Apocynum, Convallaria, Cactus Use: expectorant, emetic, cardiotonic, diuretic
Grandiflorus, Black Hellebore, Adonis, Strophantus, Red squill: Red variety of U. maritama (USE:
Squill, Oleander) Rat Poison lack the vomiting reflex)
DIGITALIS (Narrow therapeutic index) ROSE BAY / Oleander
Digitoxin: very lipophilic, longer half-life (168 Nerium oleander; constituent: Oleandrin
to 192 hours)
Digoxin: more polar, shorter half-life (30 to 40
hours), excreted via kidneys (Lanoxin)
Digitalis purpurea Digitalis lanata
Other Name Foxglove Grecian Foxglove
Constituents Digitoxin, gitoxin, Digoxin, deslanoside,
gitaloxin (desacetyllanatoside)
CARDIOTONIC/CARDIOACTIVE/STEROL GROUP ANTHRAQUINONE DERIVATIVES
Detection of this group:
Orange-red compounds
1. Keller Killani Test Soluble in dilute alcohol and boiling/hot water
test for the presence of deoxy sugar Give a characteristic red, violet, green color with a
blue or violet coloration base (NH3 or NaOH)
2. Liebermann Burchard Test
test for unsaturated sterol group 5 Types:
conc. Sulfuric and acetic anhydride a. ANTHRAQUINONE (Anthracene derivative)
(+) Green, Blue Dihydroxy phenol such as chrysophanol & rhein
Pale Yellow = if saturated sterol trihydroxyphenol such as emodin
3. Salkowskis Test b. ANTHRANOL / Anthrone type
Test for sterol Ex: Chrysarobin
Conc. Sulfuric c. DIANTHRONE (2 molecules of anthrone)
(+) Red or violet Ex: Sennas main const. SENNOSIDE
4. Keddes test d. OXANTHRONE
Unsaturated lactone Intermediate between anthraquinone and anthranol
Standard: 0.025% digitoxin in MeOH EX: Emodin oxanthrone glucoside
Blue-violet coloration e. ALOIN TYPE / C glycoside
Ex: Barbaloin in Cascara sagrada

1. BORNTRAGGERS TEST
(+) Red color on the lower alkaline layer
(-) indicates a very stable form of anthraquinone
esp. the reduced types of anthranol but first the
1 left DIGOXIN; right - OUABAIN
sample must be hydrolyzed and oxidized
2. MODIFIED BORNTRAGGERS TEST
(+) pink color or red color in the alkaline layer
indicates the presence of a very stable type of
ANTHRAQUINONE GLYCOSIDES anthraquinone
AGLYCONE: Anthracene derivatives like
o Chrysophanol (rhubarb, cascara)
o Aloe emodin (Rhubarb, Senna)
o Rhein (Rhubarb, Senna)
o Emodin (Rhubarb, cascara)
Use: Stimulant cathartics to the large intestine, delayed
effect (6 hours or more)
EXCEPT for CHRYSAROBIN
MOA: They increase tone of smooth muscle in wall of
large intestines, inhibition of Calcium ion channel.
CASCARA SAGRADA / Rhamnus purshiana / Sacred
Bark
Should be aged for at least 1 year prior to use
Dried bark of Rhamnus purshiana
Constituents: Cascarosides A and B Optical
isomers of barbaloin
Cascarosides C and D optical isomers of
chrysaloin
To reduce its bitter taste, add MgO or alkaline
earths
Casanthranol: purified mixture of the anthranol
glycosides extracted from Cascara
C 10 R SAPONIN GLYCOSIDES
Cascaroside A OH Foam upon shaking
Cascaroside B OH Bitter, acrid taste
Cascaroside C H Irritating to mucous membranes
Cascaroside C H Destroy RBCs of cold blooded animals -> fish poisons
Aglycone: Sapogenin
FRANGULA / Buckthorn bark Toxic Aglycone: Sapotoxin
Dried bark of Rhamnus frangula Steroidal in nature
Component of Movicol (Frangula + Karaya One of the most toxic plant principles (Poisonous:
gum) Sapotoxins)
Glucofrangulin A (7%); frangulin Irritating to the mucus membrane; toxic to cold-
ALOES blooded animals (fish poisons)
Dried latex of leaves of Aloe barbadensis Hemolysis Test: destroy RBC
(Curacao / Barbados Aloe), A. spicata (Cape Capillary Test: measures fluidity of extract; (+) saponins
Aloe) tend to lower surface tension
Constituents: barbaloin (aloe-emodin Aglycone: sapogenin; Use: precursors in preparation
anthrone), chrysophanic acid of steroids
Use: ingredient in compound benzoin tincture, 2 Types:
cathartic (drastic) a. NEUTRAL SAPONINS derivatives of steroids
Aloe vera Gel: treatment of burns, abrasions, (Monocot)
skin irritations, purgative, alopecia b. ACID SAPONINS derivatives of triterpenoids (Dicot)
RHUBARB / Rheum / Chinese Rhubarb
Rhizome and root of Rheum officinale, R.
palmatum, Rhaponticum
Constituent: Rhein anthrones; glucorhein
Glucogalli, gallic acid astringent prop
Rhapontic rhubarb rhaponticin (under UV
blue fluorescence, absence for other rhubarb)
SENNA / Senna leaves / Slimming tea CHARACTERISTICS: a) In aqueous solution it will form a
Dried leaflet of Cassia acutifolia (Alexandria froth; b) can hemolyze RBC
senna)
Cassia angustifolia (Tinnevelly senna); 1. FROTH TEST
Fabaceae foam/lather formation; honeycomb froth
Constituent: sennosides A and B (more potent persisting for 10 mins above 2cm is positive for
than cascara) saponins
Sennidin A, B - aglycone
Cultivated on WET lands resembling rice 2. LIEBERMANN BURCHARD TEST
paddies; as successor to rice for steroidal type of saponins present in monocot
COCHINEAL plants
Dried female insect, Dactylopius coccus (+) blue / green for triterpenoidal type present in
Carminic acid dicot plants
HYPERICUM PERFORATUM (St. Johns Wort) (+) red, pink, or violet
Clusiaceae, dried aerial parts (+) pale yellow if saturated sterol or triterpenoid
Hypericin emodin anthrone is present
Mild to moderate depression
CHRYSAROBIN 3. HEMOLYSIS TEST
Mixture of neutral principles obtained from Use blood agar plate; gugo solution as standard
Goa powder (Andira araroba); Fabaceae (+) forms a hemolytical halo (white ring) zone of
Extracted using hot benzene hemolysis
Use: ketarolytic agent, for psoriasis, 4. CAPILLARY TUBE TEST
trichophytosis, eczema Saponins tend to lower the surface tension in water
Anthralin has replaced the use of chrysarobin
5. FEHLINGS TEST
Formation of a brick red ppt. of Cu2O.
Constituent: glycyrrhizin (50x as sweet as
sugar); genin portion: glycyrrhetic acid
4% glycyrrhizic acid
Use: expectorant, flavoring agent, mask taste
of bitter drugs (paralyze taste buds)
Glycyrrhetic acid: anti-inflammatory, for peptic
ulcer, Addisons disease
2 STEROIDAL (R); PENTACYCLIC TRITERPENOID (L)
CAUTION in HTNsive patients: glycyrrhizin
increases fluid and Na+ retention, K+ depletion
CENTELLA ASIATICA (Gotu kola, tiger grass)
Dried aerial parts (Apiaceae)
Asiaticoside, centelloside
Diuretic, antirheumatic, vasodilator
QUILLAJA BARK / Soap Bark (Q. saponaria)
Rosaceae
Dried inner bark
Quillaia saponin (10%)
SENEGA (Poly senega), Polygalaceae
Dried root crown and root
STEROIDAL SAPONIN TYPE Senegin
Stim expectorant in chronic bronchitis
DIOSCOREA / Yam
Mexican Yam: Dioscorea floribunda (best
source of STEROIDS)
Constituents: BOTOGENIN
Dioscorea spiculiflora contains diosgenin
(Glucocorticoid precursor)
FENUGREEK (Trigonella foenum graecum)
Fabaceae, oily embryo of seeds
Diosgenin
SARSAPARILLA ROOT (Smilax aristolochiaefolia),
Liliaceae, dried root
Smilagenin, parillin, sarsasapogenin
Tx of psoriasis, eczema, rheumatism, syphilis,
skin diseases
GINSENG
Panax ginseng, Araliaceae 3 top GLYCYRRHIZIC ACID; bottom MOLLUSCICIDAL
Panax quinquefolium (USA) SAPONIN FROM Phytolacca dodecandra
Aphrodisiac and Adaptogen (resistance to
stress) CYANOPHORE GLYCOSIDES
Constituents: Panaxosides, Ginsenosides and glycosides which yield hydrocyanic acid as one of the
Chikusetsusaponins products; derivatives of mandelonitrile
Tx of diabetis, anemia, gastritis, sexual test for the presence of cyanogenic glycosides:
impotence Grignard test
Ginseng of Europe: Chamomile (dried leaflet of Uses: flavoring agents
Matricaria chamomila) Anticancer claims (amygdalin-containing preparation:
Laetrile/Vitamin B17)
PENTACYCLIC TRITERPENOIDAL TYPE Possible control for sickle cell anemia
GLYCYRRHIZA / Licorice Root AMYGDALIN (Water & Amygdalase)
Dried roots/stolons of Glcyrrhiza glabra mandelonitrile glucose (water and prunase)
Increases the foaminess of beer madelonitrile + glucose benzaldehyde + HCN
Rhizome and root of Glycyrrhiza glabra AMYGDALASE AND PRUNASE are collectively known as
(Spanish); G. glabra var. glandulifera (Russian) EMULSIN (APE)
Amygdalin flavored vehicle, expectorant and
sedative; found in large quantities in:
- Bitter Almond (Prunus amydalus)
- Apricot (Prunus armeniaca)
- Wild Cherry / Prunus virginiana (Prunus serotina)
Prunasin dried stem bark of Prunus serotina / Wild
black cherry tree / Prunus virginiana
- Prunasin compound formed by partial hydrolysis
of amygdalin
- enzyme emulsin: consists of a mixture of 2
enzymes (prunase, amygdalase) BLACK MUSTARD / Sinapis nigra / brown mustard
Cassava Manihot esculenta; constituent: Dried seed of Brassica nigra
mannihotoxin, linamarin (toxic cyanogen) Constituents: sinigrin (potassium myronate)
with the enzyme Myrosin
Sinigrin (myrosin) allyl isothiocyanate
(volatile) (mustard oil)
WHITE MUSTARD / Sinapis alba
Died ripe seed of Brassica alba
Constituent: sinalbin
Sinalbin (myrosin) acrinyl isothiocyanate
(volatile) (pungent-tasting, less volatile)
1. ODOR TEST
For the volatile type
Ex: Allicin (in garlic)
ID Test in Garlic:
- 10 ml 1N NaOH + 10 ml water + heat
- Use sodium nitroferricyanide ts.
- Red or orange color
2. FERRIC CHLORIDE TEST
for the non-volatile type
Fe(SCN)3 blood red

GUIGNARDS TEST FLAVONOL GLYCOSIDES


nonspecific test for cyanophore because there are other Flavonoids: rutin, quercetin, citrin
substances that can liberate H2S Bioflavonoids (hesperidin, hesperetin, diosmin,
sodium picrate paper needed in the test naringin)
yellow to brick red or any shade of red Vitamin P / Permeability factors: Rutin + hesperidin
HCN has an odor of bitter almond / peach kernels Treatment of capillary bleeding and increased
Result if within 15 minutes (+) capillary fragility; for HTN, radiation injuries
Result after 3 hours absence of cyanophore glycoside Flavonoid found in yellow flower pigment:
chalcones
ISOTHIOCYANATE GLYCOSIDES Rutin yellow crystalline powder, sol in alkali;
USE: condiments yields quercetin, rhamnose, glucose
From CRUCIFERAE family (Brassicaceae) Hesperidin yields hesperitin, rhamnose, glucose
Mustard oil glycoside Flavonoids or Bioflanoids from Citrus fruits and Soya
R-SCN Largest group of naturally occurring phenols
Flavones yellow
USES OF MUSTARD OILS: Local irritant & emetic;
Flavonoids dissolve in alkali yellow soln + acid
Rubefacient, vesicant and condiment
turn to colorless
1. Rutin and Hesperidin
- Vitamin P or Permeability Factors (formerly
known as citrin found in paprika/lemon peel)
- Uses: treatment of capillary bleeding secondary
to capillary fragility
- Treatment of symptoms of common colds
2. Hesperitin, diosmin and naringen
- Anti-HTN, pylori

WILSTATTER CYANIDIN TEST


For the presence of gamma benzopyrone nucleus
(+) orange to red to crimson & magenta occasionally
green/blue
BATE-SMITH & METCALF TEST
On addition of conc. HCl immediate red
For the presence of chalcones & aurones
If no color is produced, sample boiled and an intense
red color/violet for leucoanthocyanins
FOR ANTHOCYANINS WITH THE FLAVYLIUM ION
Extract with 1% HCl followed by boiling
(+) at boiling point an orange red to blue red coloration
is produced

VITEX AGNUS, Verbenaceae, Chaste Tree


Whole ripe dried fruit
Casticin, vitexin, penduletin
For PMS
BIRCH LEAF (Betula pendula), Betulaceae
Dried leaves
Hyperoside, quercitrin
Irigant of urinary tract in cases of inflammation,
for gout, astringent, mouthwash
CALENDULA FLOWER
C. officinalis, Asteraceae
ANTHOCYANIDINS Whole dried fully opened flowers
Hyperoside,, quercetrin
Flavonoids related to flavones GI disorders, tx of minor wounds
Anthocyanins glucosides JAVA TEA, Orthosiphon stamineus, Labiatae
- Sap pigments, the color of plant is determined by Sinensetin
pH of the sap Diuretic, DM and HPN
- Ppt in aq soln as Pb salts or picrates PASSIFLORA INCARNATA (Passion flower)
- (+) 20% HCl hydrolizes, crstallizes Dried aerial parts
Bilberry (Vaccinium myrtillus), Ericaceae Vitexin, orientin
- Anthocyanins (cyanidin 3 glucoside Cl) Sedative action
VISNAGA (Ammi visnaga), Apiaceae
Dried ripe fruits
Khellin
Coronary vasodilator, tx of angina pectoris
ALCOHOL GLYCOSIDES
Salicin produces saligenin / salicin alcohol after Detected by General Aldehyde Reactions:
hydrolysis with emulsin
AGLYCONE: Saligenin FEHLINGS TEST
Glycoside from willow and poplar barks; most from Cu2O brick red ppt
Salix purpurea and S. fragilis
Use: antirheumatic (like salicylic acid), anti- NESSLERS TEST
inflammatory
Gray ppt of Hg
Populin
Reagent K2HgI4 ts. Alkaline
- Glycoside from Populus tremula;
benzoylsalicin TOLLENS TEST
- Under phenolic glycosides (Trease and
Evans, 2009) Silver Mirror Test or Ammoniacal AgNO3 Test
Gradual deposition of silver mirror
SCHIFFS TEST
Magenta-red color restored if theres an aldehyde
complexation reaction

ALDEHYDE GLYCOSIDES
VANILLA / Vanilla bean / Pods
Unripe fruit of Vanilla planifolia (Mexican,
Bourbon vanilla); V. fragans
VIBURNUM PRUNIFOLIUM (Caprifoliaceae) Vanilla tahitensis (Tahiti Vanilla)
Black haw bark Constituents: glucovanillin (avenein),
Dysmenorrhea, bleeding, asthma glucovanillic alcohol
Has 0.2% salicin, isovaleric acid Curing activates the formation of the glycosides
HUMULUS LUPULUS (Cannabinaceae)
Vanillin/vanillic aldehyde: principle flavoring
Hops
Constituent: (4-hydroxy-3-
Dried strobiles methoxybenzaldehyde)
Lupulin, reddish brown powder has bitter Synthesized via ferulic acid
aromatic taste [humulone (-acids); lupulone Confectionary, perfumery
(-acids)] phloroglucinol der.
Xanthohumol cytotoxic effects on CA cells
Bitterness of beer
KAMALA LACTONE GLYCOSIDE
Trichomes and glands COUMARIN
Mallotus philippinensis (Euphorbiaceae) Derivative of benzo--pyrone
Dull red brown powder without odor or taste Lactone of O-hydroxycinnamic acid
Rottlerin, isorottlerin anthelmintic Flavoring agent
Tapeworm infestation NATURAL SOURCES:
Tonka Beans/Tonco Seed (Dipteryx odorata)
- dried seeds, coumarin source, tobacco manuf,
perfumery
- CONS: Dicoumarol, bishydroxycoumarin
anticoagulant, Warfarin
- FURANOCOUMARINS grapefruit juice; inhibitor of Cyt
P450 (CYP3A4, CYP3A5)

Detected by Ester Formation


C2H5-OH + CH3COOH CH3COOC2H5 (Aldehyde Glycoside)
CANTHARIDES / Spanish flies / Russian flies /
Blistering flies
Dried insect Cantharis vesicatoria
Constituent: cantharidin
Rubefacient, irritant, vesicant
Aphrodisiac (irritates urinary tract priapism), topical
warts treatment

PSORALENS
Methoxsalen, 8-methoxypsoralen
SWEET VERNAL GRASS (Anthoxanthum odoratum) Xanthotoxin: constituent of Ammi majus
SWEET CLOVER (Melilotus alba) Aid repigmentation in vitiligo, and symptomatic control
SWEET-SCENTED BEDSTRAW (Galium triflorum) for psoriasis
RED CLOVER (Trifolium pretense)

MELILOT (Fabaceae)
PSORALEN
Yellow papilionaceous flower
Improperly cured leaves and flowering tops Melilotus
officinalis
Melilotoside, melilotic acid, caffeic acid For UNSATURATED LACTONE Keddes Test
For SATURATED LACTONE Chromatography
SPRAYS USED FOR CHROMATOGRAPHY
a) Folin Ciocalteau
Blue spots
presence of hydroquinone & catechol type
b) Vanillin HCl
Pink spots
Presence of resorcinol & phoroglucinol type
4 Melimotus officinale
c) Gibbs reagent
SKIMMIN Various colors of different phenols (2,6-
Jap. Star Anise; Aesculin, aesculetin horse chestnut dichloroquinone 4-chloroimide)
tree
Anticoagulant (now prepared synthetically) PHENOL GLYCOSIDES
UVA URSI / Bearberry
Dried leaf of Arctostaphyllos uva-ursi (herbal
tea available)
Ericaceae
Arbutin; methyl arbutin
Diuretic, astringent, weak urinary antiseptic
Skimmin
MILLONS TEST
Peach/salmon/pink coloration mercury complex of the
nitrophenyl derivative
O C 6 H 11 O5 OH

+ H2O + C 6 H 12 O6

G lucos e
ANGELICA ROOT (A. archangelica, Apiaceae) OH OH
Arbutin Hydroquinone
Angelicin, archangelicin, apterin
Coronary vasodilator effects, Ca antagonist
MISCELLANEOUS GLYCOSIDES
Neutral Glycosides
Dried ripe seed of Anamirta cocculus
(Menispermaceae)
Bitter Glycosides
Quassia amara
- Heartwood of Quassia amara
(Simarubaceae) in Surinam (Bitter Wood,
Bitter Ash) QUASSIN
Picrasma excels
- Jamaican; PICRASMIN
Gentiana lutea
- Root & rhizome
- Bitter root; Gentianaceae
Sweet Glycosides
Glycyrrhiza glabra var. typica & var. glandulifera
(Fabaceae)
Coloring Glycosides dried stigmas
Crocus sativus (Iridaceae) PICROCROCIN
Haematoxylon campechianum (Fabaceae)
HEMATOXYLIN; Heartwood
Pterocarpus santalinus (Fabaceae) SANTALIN
Coccus cacti (Coccidae) CARMINIC ACID;
dried female insect enclosing a young larvae;
Dactylopius coccus
Ochrolechia tartarea (Ochrolechiaceae)
natural source of litmus powder
Volatile Oil-Containing Glycoside
Arnica
- Dried flower heads of Arnica montana
(European); A. fulgens; A. sororia; A. cardifolia
(American)
- Mountain tobacco
- ARNICIN

Calamus
- The dried peeled rhizome of Acorus calamus
(Aracaceae)
- Sweet Flag
- ACORIN

Potrebbero piacerti anche