Tannins Flashcards by meimei moo

t/f: tannins are a mixture of polyphenols difficult to separate because they
strongly crystallize

false. Tannins are a mixture of polyphenols difficult to separate because they
DO NOT crystallize

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t/f tannins convert animal hide to leather

true

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source of tannins

barks / stems

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Use: astringent, antidote to alkaloidal poisoning, precipitants, tanning and dyeing industry

tannins

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example of carcinogenic tannin

chewing of betel nut (Areca catechu)

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mechanism of betel nut as carcinogenic

contains ARECOLINE, which is a CNS STIMULANT and a family of nicotine
link to high risk of ESOPHAGEAL CANCER

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tannins

pseud & true

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true tannins

hydrolysable, condensed, complex

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hydrolysable tannins

gallo and ellagitannins

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t/f: pseudotannins do not precipitate leather but can precipitate gelatin

true

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pseudotannins
- MW of ___________
- _____ MW

MW of <1,000
LOW MW since they exist as individual molecules (combine = true tannin)

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true tannins
- MW of ___________
- _____ MW

MW of 1000 - 5000
MODERATE SIZE MW

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t/f: true tannin polyphenol must be too large

false. they must NEITHER be:
- Too large (greater than 5000) as to be unable to enter the interstices of the collagen fibrils
- Too small (less than 1000) that it is unable to crosslink protein molecules of adjacent fibrils

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t/f pseudo and true tannins are both POSITIVE in GELATIN TEST

true

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true tannin result on GOLDBEATER’s

(+) Brown black spot (using ox intestine)

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pseudo tannin result on GOLDBEATER’s

negative

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test for tannin mechanism

Quantitatively detected by tanning Gold-beater’s skin test by its adsorption on standard hide powder

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t/f: tannin can precipitate gelatin

true

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true tannins (name)
hydrolyzable : __________
non-hydrolyzable : __________

hydrolyzable : PYROGALLOTANNIN
non-hydrolyzable : PHLOBATANNIN, CONDENSED

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phenolic nuclei
hydrolyzable : __________
non-hydrolyzable : __________

hydrolyzable : Gallic and ellagic
non-hydrolyzable : Catechin and
chlorogenic acid

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yield when heated
hydrolyzable : __________
non-hydrolyzable : __________

hydrolyzable : PYROGALLOL
non-hydrolyzable : CATECHOL

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leather produced
hydrolyzable : __________
non-hydrolyzable : __________

hydrolyzable : BLOOM
non-hydrolyzable : TANNER’S RED

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Hydrolyzable result in
FeCl3 =
Br2 =
KMnO4 =
Matchstick =
Chlorogenic =

Hydrolyzable result in
FeCl3 = BLUE BLACK
Br2 = NO PPT
KMnO4 =COLORLESS
Matchstick = -
Chlorogenic = -

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Non-hydrolyzable result in
FeCl3 =
Br2 =
KMnO4 =
Matchstick =
Chlorogenic =

Non-hydrolyzable result in
FeCl3 = GREEN BLACK
Br2 = PPT
KMnO4 = VIOLET
Matchstick = (+) PINK/RED
Chlorogenic = (+) GRADUAL CHANGE TO GREEN

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t/f Hydrochloric acid cannot hydrolyze catechins and chlorogenic acid that is why there is a formation of precipitate

true

phenolic aglycone: gallic acid

gallotanin

phenolic aglycone: ellagic acid, no sugar component

ellagitannin

hydrolyzable tannins contains glucose (thus, glycosides)

true

hydrolysable tannin from the lactonization of hexahydroxydiphenic acid

ellagitannin

Contains flavonoids (nonglycoside)

nonhydrolyzable / condensed tannin

t/f: non hydrolyzable tannins are readily hydrolyzed to simpler molecules and do not contain sugar moiety

false. NOT READILY HYDROLYZED

t/f: Cinnamic acid and Coumaric acid can form condensed Tannins

true

Hybrid (mix of) both hydrolysable and non-hydrolysable tannins

complex

Term applied by Okuda for tannins with both hydrolysable and condensed portions

complex

hamamelis is used in eyedrops to

soothe the eye

Scientific Name: Leaf of Hamamelis virginiana Constituent: Hamamelitannin

Hamamelis / Witch Hazel

Hamamelis use

Use: astringent, hemostatic properties

t/f: witch hazel is an anti-inflammatory due to 5-LOX inhibition (can be used for teething preparation, sprains, bruise, superficial wounds)

true

nutgall / aleppo oak old concept by _______ new concept by _________

old concept by TYLER new concept by TREASE & EVANS

Constituent: tannic acid, gallic acid

old concept

Constituent: 50-70% gallotannic acis, gallic acid

new concept

use of nutgall

use: tanning and dyeing industry, astringent

Scientific Name: Excrescence from twigs of Quercus infectoria

Nutgall / Aleppo Oak

Nutgall caused by the puncture of insect Cynips tinctoria

old concept

Nutgall caused by the puncture and deposition of eggs of gallwasp Adleria gallaetinctoriae / Cynips tinctoriae

new concept

nutgall color which has the most gallic acid

blue color

nutgall color which has decomposed tannin, with circular tunnel (no tannin anymore, not harvested)

white color

nutgall color which is mature as the insect escape from the gall

white color

CNS active comp of MeOH gall extract

syringic acid

Scientific Name: Dried pericarp of fruit Punica granatum

Pomegranate

t/f pomegranate has 28% ellagitannin (primarily punicalagin)

true

pomegranate use

use: astringent, for diarrhea

pomegranate has synergism with antibiotics especially against _________ and a potential against ____________ and ___________

pomegranate has synergism with antibiotics especially against MRSA and a potential against HERPES and HIV

Scientific Name: Vaccinium macrocarpon Family: Ericaceae Constituent: Condensed tannins Use: For urinary tract infections

Cranberry

t/f: tannins are soluble in water, alcohol, glycerol, dilute alkalis, and acetone BUT sparingly soluble in organic solvents

true

test that differentiates pseudo and true tannins using ox intestine

goldbeater's test

negative in goldbeater's

pseudotannins

positive result of goldbeater's

black/brown

general test for tannins

gelatin test

positive result for gelatin test (both true and pseudo)

fleshy ppt

test for catechin (pseudotannin)

matchstick test

t/f: matchstick test positive on hydrolyzable tannin

false. test positive on NON HYDROLYSABLE tannin (+) pink/red wood

pink/red wood on flame on matchstick test is due to

phloroglucinol

test for (+) non-hydrolysable tannins with result of green color

chlorogenic acid test

tannin use: Treatment for burns, bed sores, minor ulceration

Astringent

tannin use: styptics and internally for protecting inflamed surfaces of mouth and throat

Protein precipitant

Inhibit peroxidation and trap free radicals

antioxidant

tannin use: Stop cancer, inhibits replication of virus capable of preventing or stopping wounds and then applied to the wounds

Enzymatic inhibitors

tannin use: also used for alkaloidal and heavy metal poisoning as part of the "universal antidote" (with MgO and activated charcoal)

Antidote

t/f: Tannins can precipitate alkaloids and heavy metals

true

potential antitumor, anti-angiogenic in mice (especially epigallocatechin-3-gallate)

condensed tannin

dangers of tannin

hepatotoxic, carcinogenic

effect when absorbed tannic acid can cause severe central necrosis of the liver

hepatotoxic

Tannins Flashcards

(75 cards)