EX 5 Flashcards
- a compound that yields one or more sugar and non-sugar componenet among the products of hydrolysis
- also known as sugar ethers
GLYCOSIDES
GLYCOSIDES
sugar component
glycone
GLYCOSIDES
non-sugar component
aglycone
GLYCOSIDES
are also known as
SUGAR ETHERS
- for regulatory, protective, sanitary compounds in plants
- various therapeutic uses such as cardiac glycosides, laxatives, local irritants, analgesics
GLYCOSIDES
GLYCOSIDES
for specific congestive heart failure
cardiac glycosides
GLYCOSIDES
senna leaves contains
senosites
GLYCOSIDES
- sugar component
- common denominator
- inactive
glycone
GLYCOSIDES
- non-sugar component
- basis of classification
- active
aglycone (genins)
GLYCOSIDES
aglycone is also known as
genins
GLYCOSIDES | ACCDNG TO THE GLYCONE PRESENT
if it is GLUCOSE
glucoside
GLYCOSIDES | ACCDNG TO THE GLYCONE PRESENT
if it is FRUCTOSE
fructoside
GLYCOSIDES | ACCDNG TO THE GLYCONE PRESENT
if it is GALACTOSE
galactoside
GLYCOSIDES | ACCDNG TO THE GLYCONE PRESENT
if it is GLUCURONIC ACID
glucuronide
types of glycosidic bonds
C
O
N
S
- the aglycone portion is an ALCOHOL derivative
- WILLOW BARK (Salix purpurea, S. fragilis)
ALCOHOL GLYCOSIDES
ALCOHOL GLYCOSIDES
____ hydrolyzes salicin to become saligin
EMULSIN
ALCOHOL GLYCOSIDES
emulsin hydrolyzes salicin to become ____
saliginin
ALCOHOL GLYCOSIDES
USE:
Willow bark
Salix purpurea, S. fragilis
rheumatoid arthritis
ALCOHOL GLYCOSIDES
other name for salicin
salicyl alcohol
ALCOHOL GLYCOSIDES
Salicin when OXIDIZED will become
salicylic acid
ALCOHOL GLYCOSIDES
SALICYLIC ACID when undergone ACETYLATION will become
aspirin
- the aglycone poriton is aldehyde derivative
- VANILLA (Vanilla planifolia, V. tahitensis)
ALDEHYDE GLYCOSIDES
ALDEHYDE GLYCOSIDES
the aglycone portion of VANILLA
vanillin
- largest group of naturally occuring PIGMENTS
- used as dyes, cathartics, and stimulant laxatives (habit-forming)
- derivatives are often orange-red compounds tat are soluble in hot water and in dilute alcohol
- give a characteristic red, violet, green, or purple color with a base
ANTHRAQUINONE GLYCOSIDES
ANTHRAQUINONE GLYCOSIDES
derivatives are often ____ compounds that are soluble in HOT water and in DILUTE alcohol
orange-red
ANTHRAQUINONE GLYCOSIDES
dervatives are SOLUBLE in ____ and in ____
HOT water
DILUTE alcohol
ANTHRAQUINONE GLYCOSIDES
give a characteristic ____, ____, ____, or ____ color with a base
red
violet
green
purple
VANILLA
Vanilla planifolia, V. tahitensis
ALDEHYDE GLYCOSIDES
WILLOW BARK
Salix purpurea, S. fragilis
ALCOHOL GLYCOSIDES
ANTHRAQUINONE GLYCOSIDES | TESTS
BONTRAGER’s test
red color in lower ammoniacal layer
R - red A - ammoniacal
ANTHRAQUINONE GLYCOSIDES | TESTS
MODIFIED BONTRAGER’s test
PINK
- Cascara sagrada (Rhamnus purshianus)
- Frangula (Rhamnus frangula)
- Aloe (Aloe barbadensis, A. ferpx, A. africana, A. spicata)
- Rhubarb (Rheum officinale, R. palmatum, R. rhabarbarum)
- Indian rhubarb (Rheum emodi, R. webbianum)
- Senna (Cassia acutifolia, C. angustifolia)
- Chrysarobin (Andira araroba)
ANTHRAQUINONE GLYCOSIDES
USE of ALL anthraquinone glycosides
CATHARTIC
all anthraquinone glycosides are CATHARTIC, except
CHRYSAROBIN
Andira araroba
USE:
Chrysarobin
Andira araroba
keratolytic
- the agluycone portion are derivatives of benzo-δ-pyrone nucleus
delta
CHROMONE glycosides
- Hypericum erectum
- Japanese eurya (Eurya japonica)
- Cassia multijuga
CHROMONE glycosides
- the aglycone portion are derivatives of benzo-α-pyrone nucleus
alpha
COUMARIN glycosides
- Tonka bean (Dipteryx odorata)
- Meadowsweet (Filipendula ulmaria)
- Sweet clover (Melilotus officinalis)
- Vanilla grass (Anthoxanthum odoratum)
COUMARIN glycosides
- releases cyanides
- yields hydrocyanic acid upon hydrolysis
- often found in legumes, root crops, and grasses
- usually in plants together with hydrolytic enzymes
- most are lost after plant harvest due to spontaneous hydrolysis
CYANOGENIC GLYCOSIDES
CYANOGENIC GLYCOSIDES
yields ____ upon hydrolysis
hydrocyanic acid
CYANOGENIC GLYCOSIDES
often found in ____, ____, ____
legumes
root crops
grasses
CYANOGENIC GLYCOSIDES
usually in plants together with ____
hydrolytic enzymes
CYANOGENIC GLYCOSIDES
most are LOST after plant harvest due to ____
spontaneous hydrolysis
amygdalin
CYANOGENIC glycoside
CYANOGENIC GLYCOSIDES
- laetrile
- vitamin B17
- thought to have anti-tumor properties
amygdalin
CYANOGENIC GLYCOSIDES | TESTS
appearance of various shades of RED within 15minutes when the tube is warmed
(yellow to brick red)
GUIGNARD’S TEST
CYANOGENIC GLYCOSIDES | TESTS
GUIGNARD’s test
various shades of red within 15mins when warmed
yellow to brick red
- Wild cherry (Prunus serotina)
- Apricot (Prunus armeniaca)
- Almond (Prunus amygdalus)
- Cassava (Manihot esculenta)
CYANOGENIC GLYCOSIDES
- most common
- phenolic plant pigments containing a benzo-γ-pyrone nucleus
- include anthocyanins, leucoanthocyanins, catechins, aurones, chalcones
- have reported anti-viral, anti-fungal, anti-inflammatory, cytotoxic activites
FLAVONOID glycosides
FLAVONOID GLYCOSIDES
ANTHOCYANINS on hydrolysis yield sugars and COLORED aglycones known as ____
anthocyanidins
FLAVONOID GLYCOSIDES
LEUCOANTHOCYANINS have their aglycone known as ____
leucoanthocyanidin
FLAVONOID GLYCOSIDES | TESTS
BATE-SMITH & METCALF test
strong red or violet
FLAVONOID GLYCOSIDES | TESTS
WILSTATTER “CYANIDIN” test
orange to red, crimson, magenta
occasionally green or blue
- Hesperidin
- Naringin
- Rutin
- Quercitin
FLAVONOID GLYCOSIDES
the aglycone portion is an iridoid, usually bound to the glyucone portion glucose
IRIDOID GLYCOSIDES
- Asterids (Aucuba japonica, Eucommia ulmoides)
- Catalpa (Catalpa bignonioides, C. speciosa)
IRIDOID GLYCOSIDES
- derived from the hydrolysis of GLUCOSINOLATES (sulphur-containing compounds found in cruciferous plants)
- found their importance because of their anti-cancer properties
ISOTHIOCYANATE GLYCOSIDES
- Black mustard (Brassica nigra)
- White mustard (Brassica alba)
ISOTHIOCYANATE
ISOTHIOCYANATE GLYCOSIDES
derived from the hydrolysis of ____ (sulphur-containing compounds found in cruciferous plants)
GLUCOSINOLATES
ISOTHIOCYANATE GLYCOSIDES
glucosinolates are ____-containing compounds
sulphur
ISOTHIOCYANATE GLYCOSIDES
glucosinolates are found in ____ plants
cruciferous
the aglycone portion is a phenol group
PHENOL GLYCOSIDES
Bearberry
(Arctostaphylos uva-ursi)
PHENOL glycosides
- cardiac glycosides
- prominent effect on the heart muscle
- cardenolide, bufadienolide
STEROIDAL GLYCOSIDES
STEROIDAL GLYCOSIDES
also known as
cardiac glycosides
STEROIDAL GLYCOSIDES
steroidal nucleus
cyclopentanoperhydrophenanthrene
STEROIDAL GLYCOSIDES
STEROIDAL SKELETON:
* more common
* has optimum activity
* C-23
* 5 membered lactone ring
CARDENOLIDE
STEROIDAL GLYCOSIDES
STEROIDAL SKELETON:
* less common
* less activity
* C-24
* 6 membered lactone ring
BUFADIENOLIDE
STEROIDAL GLYCOSIDES | TESTS
test for 2-DEOXYSUGARS
KELLER-KILLIANI
STEROIDAL GLYCOSIDES | TESTS
KELLER-KILLIANI test
reddish brown to blue or purple
STEROIDAL GLYCOSIDES | TESTS
test for unsaturated STEROIDS and TRITERPENES
LIEBERMANN-BURCHARD
STEROIDAL GLYCOSIDES | TESTS
LIBERMANN-BURCHARD test
blue to green, red, pink, purple, or violet
STEROIDAL GLYCOSIDES | TESTS
test for unsaturated LACTONES
KEDDE’s
STEROIDAL GLYCOSIDES | TESTS
KEDDE’s test
blue-violet
- Foxlgove (Digitalis purpurea)
- Grecian foxglove (Digitalis lanata)
- Convallaria (Convallaria majalis)
- Pheasant’s eye (Adonis vernalis)
- Black hellebore (Helleborus niger)
- Dogbane (Apocynum cannabinum)
- Adelfa (Nerium oleander)
- Strophantus (Strophantus kombe)
- Ouabain (Strophantus gratus, Acokanthera ouabaio)
- Squill (white var of Urginea maritima, U. indica)
- Red squill (red var. of U. maritima)
STEROIDAL glycosides
STEROIDAL GLYCOSIDES
white variation of Urginea maritima
squill
STEROIDAL GLYCOSIDES
red variety of U. maritima
red squill
- found their use as natural sweeteners, as subtitute for sugar (40-300 times sweeter than sucrose
STEVIOL GLYCOSIDES
STEVIOL GLYCOSIDES
found their use as ____
natural sweeteners
40-300 times SWEETER than sucrose
steviol, stevia ??
STEVIA
Stevia rebaudiana
STEVIOL glycosides
- steroidal/triterpenoid glycosides characterized by their ability to froth when agitated - used as detergent
- exert a powerful hemolytic action on RBCs and are highly toxic when injected into the bloodstream - used as fish poison
- harmless when taken orally
- 2 types: steroidal, triterpenoidal
SAPONINS
SAPONINS
they are characterized by their ability to ____ when agitated
FROTH
SAPONINS
froth: are used as ____
detergent
SAPONINS
exert a ____ on RBCs and highly toxic when injected into the bloodstream
powerful hemolytic action
SAPONINS
- contains ____ which is a poisonous saponin
- has interesting spermicidal and mulloscicidal activity
SAPOTOXIN
.SAPONINS
sapotoxin has interesting ____ and ____ activity
spermicidal and molluscicidal
SAPONINS
2 TYPES:
* monocot
* Dioscoreaceae
STEROIDAL
SAPONINS
2 TYPES:
* dicot
* Agavaceae
triterpenoidal
SAPONINS
aglycone portion
sapogenin
SAPONINS
27 carbons
Neutral saponins
Steroids
SAPONINS
30 carbons
Acid saponins
Triterpenoids
SAPONIN | SYNTHESIS REAGENTS USE
use to produce acid saponin if present are PRECIPITATED as LEAD SALTS
Neutral Lead acetate
SAPONIN | SYNTHESIS REAGENTS USE
Neutral Lead acetate is used to produce ____ if present are precipitated as lead salts
acid saponin
SAPONIN | SYNTHESIS REAGENTS USE
use to precipitate NEUTRAL saponin
Basic Lead Acetate
SAPONIN | SYNTHESIS REAGENTS USE
Basic Lead acetate is used to precipitate ____
neutral saponin
SAPONIN | SYNTHESIS REAGENTS USE
use to DECOMPOSE lead acetate
Hydrogen sulfide
SAPONIN | PROPERTIES
soluble in ____ and ____
water & alcohol
SAPONIN | PROPERTIES
form ____ with water
persistent froth
SAPONIN | PROPERTIES
cause ____ if reach the blood
hemolysis of RBCs
SAPONIN | PROPERTIES
shape/form
amorphous
SAPONIN | PROPERTIES
taste
bitter, acrid
SAPONIN | TESTS
honeycomb froth greater than 2cm persistent for 10mins
FROTH test
SAPONIN | TESTS
clear zones of hemolysis (hemolytic halos)
Agar cup hemolytic test
SAPONIN | TESTS
formation of precipitate (BARIUM HYDROXIDE reacts with neutral saponins)
neutral saponins have NO acid-base groups
BARYTA WATER TEST
SAPONIN | TESTS
BARYTA WATER TEST:
____ reacts with neutral saponins
barium hydroxide
SAPONIN | TESTS
neutral saponins have NO ____ groups
acid-base groups
SAPONIN | TESTS
formation of precipitate (BASIC LEAD ACETATE reacts with neutral saponins)
LEAD ACETATE TEST
SAPONIN | TESTS
PHYSICAL TEST: Gugo Extract
* color
golden yellow to orange
SAPONIN | TESTS
PHYSICAL TEST: Gugo Extract
* odor
odorless
SAPONIN | TESTS
PHYSICAL TEST: Gugo Extract
* taste
slightly bitter, acrid
- Licorice (Glycyrrhiza glabra)
- Yam (Dioscorea floribuna, D. alata)
- Ginseng (Panax ginseng, P. quinquefolius)
- Gugo (Entada phaseoloides)
SAPONINS
IRIDOID GLYCOSIDES
glycoside portion of CATLPA
Catalpol
IRIDOID GLYCOSIDES
glycoside of ASTERIDS
Aucubin
glycone portion of SENNOSIDE
glucose
glycone portion of FRANGULIN
rhamnose
glycone portion of DIGITOXIN
digitoxose