GLYCOSIDES (Glucoside)

Sugar ethers; heteropolysaccharides

Compounds that yield one or more
sugars among the products of
hydrolysis
Both alpha and beta glycosides are
possible; only beta form occurs in
plants

1.) Non-sugar portion- Aglycone/Genin

portion
2.) Sugar portion Glycone
- classification base on aglycone
CPP- cyclopentanophenanthene
- steroidal structure
- indicates cardiac glycoside
CARDIAC GLYCOSIDES
-have specific action on the cardiac
tissues; they increase force of systolic
contraction
- aglycones: cardenolide, bufadienolide
bufadienolide: animals ex. Bufferlin from
frogs skin
-CPPP nucleus
- inhibit Na/K ATPase, thereby increasing
the Ca2+ inside the heart muscles (+
inotropic effect)
17th Beta position 5 membered lactone
ring (cardenolide)
17th Beta position 6 membered lactone
ring (Bufadienolide)
K most abundant intracellular cation
Na- most abundant extracellular cation
Digitalis inhibits K+ going outside and the
Na+ going inside therefore:
Increase in Na
Decrease in K
Increase Ca2+
DIGITALIS (narrow therapeutic index)
Digitoxin: very lipophilic, longer halflife (168 to 192hrs)
Digoxin- more polar, shorter half-life
(30 to 40hrs) excreted via kidneys
(Lanoxin)
Digitalis
Digitalis Lanata
Purpurea
Fox glove Grecian Foxglove

Other
names
constituent
s

Digitoxin,
gitoxin
gitaloxin

Digoxin,
desianoside
decacetyllanatos
ide

CONVALLARIA/LILY-OF-THE-VALLEYROOT
Rhizome and root of convallaria
majalis
Constituent: convallotoxin
APOCYNUM/BLACK INDIAN
HEMP/DOGBANE/CANADIAN HEMP
Rhizome and root of apocynum
canabinum
Constituent: cymarin
ADONIS/PHEASANTS EYE
Adonis vernalis
Constituents: adonitoxin, cymarin,
K-strophantin
CACTUS GRANDIFLORUS/NIGHT
BLOOMING CEREUS
Stem of selenicereus grandifolia
BLACK HELLEBORE/ CHRISTMAS ROSE
Rhizome and root of helleborus niger
Constituents: helleberin, green
hellebore (cardiac depressant), black
hellebore (stimulant)
STROPHANTUS
Dried, ripe seed of strophantus
kombe
Preparation of arrow poisoning
(Africans)
Constituens: K-Strophantin
Strohphantus gratus: has ouabain (Gstrophanthin) tubocurarine HCl
SK muscle relaxant
Arrow head poison
SQUILL/SQUILL BULB
Bulb of white variety of Urginea
maritime
Constituent: seillaren
Use: expectorant, emetics,
cardiotonic, diuretic
Red squill: variety of Urmaritima
Use: rat poison lack the vomiting
reflex
ROSE BAY/ OLEANDER
Nerium oleander

 Constituents: oleandrin
DACCBASSO
FAMILY
L - Liliaceae
A - Aponaceae
E Euphorbiaceae
CARDIOTONIC/CARDIOACTIVE/STEROL
GROUP
Detection of this group:
1. Keller Killiani Test test for the
presence of deoxysugar
- blue violet coloration
2. Liebermann Buchard Test - test
for unsaturated sterol group
conc. Sulfuric and acetic anhydride
(+)Green, Blue
- pale yellow if saturated sterol
3. Salkowskis Test test for sterol
- conc. Sulfuric (+) red or violet
4. Keddes Test - unsaturated lacton
- std. 0.025% digitoxin in MeOH
- blue violet coloration
ANTHRAQUINONE GLYCOSIDES
Aglycone: Anthracene
- use: stimulant cathartics except
for chrysarobin
- orange-red compounds
- sol. In dil alc. and boiling/hot
water
- give a char. Red, violet, green
color w/ a base
GROUP 1 Anthraquinone
2 Anthrone
3 Dianthrone
4 Oxanthrone
5 Aloin Type
5 TYPES:
1.) Anthraquinone (anthracene
derivative) dihydroxyphenol such
as chrysophanol & emodin
2.) Anthranol/ anthrone type
Ex. Chrysarobin
3.) Dianthrone (2 molecules of
anthrone)
Ex. Sennas main const. sennoside
4.) Oxanthrone intermediate bet.
Anthraquinone and anthranol
Ex. Emodin oxanthrone glucoside
5.)
Aloin Type

Ex. Barbaloin in cascara sagrada

Borntragers Test
(+) red color on the low alkaline layer
(-) indicates a very stable form of
anthraquinone esp. the reduced types of
anthranol but first sample must be
hydrolyzed and oxidized
Modified Borntragers Test
(+) pink color or red color in the alkaline
layer indicates the presents of a very
stable type of anthraquinone
CASCARA SAGRADA/ RHAMNUS
PURSHIANA/ SACRED BARK
Should be aged atleast 1yr prior to
use
Dried bark
Constituents: cascarosides a and b
optical isomers of barbaloin
Cascarosides c and d optical
isomers of chrysaloin
To reduce bitter taste add MgO or
alkaline earths
Casanthranol purified mixture of
anthraquinone glycosides extracted
form cascara
FRANGULA/ BUCKTHORN BARK
Dried bark
Component of Movicol (frangula +
karaya gum)
Frangulin
ALOES
Dried latex of leaves
Constituents: barbaloin (aloe-emodin
anthrone) , chrysophanic acid
useL ingredient in compound benzoin
tincture, cathartic (drastic)
Aloe vera gels: treatment of burns,
abrasions, skin irritations, purgative,
alopecia
RHUBARB/RHEUM/CHINESE RHUBARB
Rhizome and root
Constituents: rhein anthrones
SENNA/SENNA LEAVES/SLIMMING TEA
Dried leaflet
Constituents: sennosides A and B
(more potent thant cascara)
Cultivated on wet lands
CHRYSAROBIN

Mixture of neutral principles obtained

from goa powder
Extracted using hot benzene
Use: keratolytic agent, for psoriasis,
trichophytosis, eczema
Anthralin has replaced the use of
chrysarobin
CRAFSC
SAPONIN GLYCOSDIES
- foam upon shaking
- bitter, acrid taste
- irritating to mucous membrane
- destroy rbc of cold blooded
animals -> fish poison
- hemolytical halo
- tonic
- Aglycone: Sapogenin
- Steroidal in nature
- 4th ring is 5-membered steroidal
- 4th ring is 6 membered terpinoidal
- one of the most toxic plant
- capillary test: measures fluidity of
extract; (+) saponins tent to
decrease surface tension
- precursor in the prep of steorids
- 2 Types:
a.) Neutral Saponins
derivative of steroids
b.) Acid Saponins derivative of
triterpenoids
Characteristics:
a.) in aqueous soln it will form a
froth
b.) can hemolyze RBC
FROTH TEST
- foam/lather formation
- honeycomb froth persisting for 10 min
about 2cm is positive
- add aqueous sod carbonate if froth is
unstable to neutralize free acids
LIEBERMANN BURCHARD TEST
- for steroidal type of saponin in
monocot plants
- (+) blue or green
- for triterpenoidal type present in
dicot plants
- (+) red, pink or violet
- pale yellow if saturated sterol or
triterpenoid is present

HEMOLYSIS TEST
- use blood agar plate
- gugo soln as std
- (+) forms a hemolytical halo
(white ring) zone of hemolysis
CAPILLARY TUBE TEST
- saponins tend to lower the
surface tension in water
FEHLINGS
-formation of a brick red ppt of Cu2O
GLYXYRRHIZA/ LICORICE ROOT
pentacyclic triterpenoidal
dried roots
increases the foaminess of beer
constituents: glycyrrhizin (50x as
sweet as sugar)
use: expectorant, flavoring
glycyrrhetic acid: anti-inflammatory
for peptic ulcer, addisons disease
caution in hypertensive patients
K depletion
STEROIDAL TYPE
DIOSCOREA/ YAM
Constituent: botogenin
Contains diosgenin which is a
glucocorticoid precursor
Best source of steroids
GINSENG
Panax quinquefolius
Constituents: panaxosides,
ginsenosides and chikusetsusaponins
CYANOPHORE GLYCOSIDES
- yield hydrocyanic acid as one of
the products
- derivatives of mandelonitrile
- test: Grignard Test
- uses: flavoring agent, anticancer
claims
- possible control for sickle cell
anemia
- amydalase and prunase are
collectively known as EMULSIN
Amygdalin found in large quantities in
bitter almond (prunus amygdalus)
- flavored vehicle, expectorant and
sedative

Prunasin- dried stem brak of prunus

serotina
GUIGNARDS TEST
- non specific test bec there are
other subs that can liberate
aldehyde
- sod nicrate paper is needed
- yellow to brick red
- HCN has an odor of bitter almond
- Result: if within 15mins (+); after
3hrs (-)
ISOTHIOCYANATE GLYCOSIDES
- use: condiments
- CRUCIFERAE family
BLACK MUSTARD/ SINAPIS NIGRA/
BROWN MUSTARD
Constituent: sinigrin (K myronate) w.
enzyme myrosin
Sinigrin volatile mustard oil
WHITE MUSTARD/ SINAPIS ALBA
Constituent: sinalbin (less volatile)
ODOR TEST
-for the volatile type
ex. Allicin (in garlic)
ID TEST OF GARLIC
10mL 1N NaOH + 10mL water + heat
use sodium nitroferricyanide t.s
- red/orange color
FERRIC CHLORIDE TEST
-for non volatile
-blood red
Use of Mustard Oils:
-local irritant and emetic
-rubefacient, vesicant and condiment
FLAVONOL GLYCOSIDES
- flavonoids: rutin, quercetin, citrin
- bioflavonoids (hesperidin,
hesperetin, diosmin, naringen)
- capillary bleeding and increase
capillary fragility
Flavonoids or Bioflavonoids from
Citrus fruits and Soya
- largest group of naturally
occurring phenol
- flavones: yellow

flavonoids dissolved in alkali- yel

soln- acid turn to colorless

1.)
RUTIN AND HESPERIDIN
VIT P or permeaboloty factors
(formerly known as citrin found in
paprika/ lemon peel)
-treatment for capillary bleeding
- for symptoms of common colds
ANTHOCYANIDINS
BILBERRY (VACCINIUM MYRTILLUS)
ERICACEAE
FLAVONOL GROUP/ GLYCOSIDE
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 W/ THE
FLAVYLIUM ION
- extract w. 1% HCl, boil
- (+) at boiling pt an orange to blue
red coloration is produced
VITEX AGNUS, VERBENACEAE, CHASTE
TREE
whole ripe dried fruit
for PMS
BIRCH LEAF (BETULA PENDULA)
BETULACEAE; DRIED LEAVES
for urinary tract inflammation, for
gout, astringent
CALENDULA FLOWER
for minor wounds
JAVA TEA, ORTHOSIPHON STAMINEUS,
LABIATAAE
diuretic
for HTN
PASSIFLORA INCARNATA (PASSION
FLOWER)
sedative

ALCOHOL GLYCOSIDES
-detected by esther formation
Salicin produces saligenin/ salicin
alcohon after hydrolysis with emulsin
- Aglycone: Saligenin
antirheumatic, anti-inflammatory
VIBURNUM PRUNIFOLIUM
Dysmenorrhea, bleeding, asthma
HUMULUS LUPULUS (CANNABINACEAE)
Lupulin: reddish brown powder has
bitter aromatic taste
Detected by General aldehyde
reaction:

FEHLINGS TEST
-brick red ppt
NESSLERS TEST
-gray ppt
TOLENS TEST OR SILVER MIRROR
TEST
-gradual disposition of silver mirror
SCHIFS TEST
- magenta-red color restored if theres a
aldehyde