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INTRODUCTION
Tannins:
•These are the secondary metabolites which is in the form of a solution in cell
sap or distinct vacuoles.
•They are known as astringents from longtime.
•Tannins are used in leather industry to prevent Putrefaction. Putrefaction is
the final stage of death or decomposition.
•They are chemically complex organic substances contains polyphenols.
•They have high molecular weight.
•They are devoid of N
•They are non-crystalline substances.
General Tests:
•It precipitates alkaloids & gelatine.
•Tannins are precipitated by salts of Cu, Sn & Pb.
•Tannins are precipitated by chromic acid solution.
•Tannins are precipitated by Fecl3 is bluish black or brownish green color.
Classification of Tannins:
Based on the chemical nature or behaviour towards dry distillation process.
They are divided into
Black Catechu Pale Catechu Pterocarpus
Synonym Cutch, Catechu,
catechu nigrum
Pale catechu, terra
japonica, Gambier
Bijasal, Indian
kino tree, red
sandal wook, rakta
chandan
B. Source Extract prepaed –
heart wood of A.
Catechu -
Leguminosae
Extract prepared –
Leaves & young
shoots – Uncaria
gambier –
Rubiaceae
Dried juice –
Ptercarpus
marsupium –
Leguminosae
Chemical
Composition &
Chemistry
Catechu tannic acid
Acacatechin
Small amoutns –
Quercetin
 Catechin is a
flavan-3-ol, a
type of natural
phenol and
antioxidant.It is
a plant
secondary
metabolite.
7-33% catechins
Catechutannic acid
22 -50%
Quercitin
Gambier –
flourescin
 Catechin is a
flavan-3-ol, a
type of natural
phenol and
antioxidant.It is
a plant
secondary
metabolite.
70-80% Kinotannic
acid
Kino red
K-Pyrocatechin
Gallic acid
Kinotannic acid is a
glucosidal tannin.
Kinored is
anhydride of kinoin.
Kinoin in the
presence of oxidase
enzyme it forms
insoluble
phlobaphene.
It consists of santal
Pterocarpin
homopterocapin
Therapeutic uses
& Commercial
Applications
Dyeing & tanning
industry
Catechu is
considered as one
of the most potent
herbal medicines
use for anti-
diarrhea and anti-
ulcer
Local astringent.
Dyeing & tanning
industry
Catechu is included
in mouthwashes
and gargles used
for gum disease
(gingivitis), pain
and swelling inside
the mouth
(stomatitis), sore
throat, and mouth
ulcers.
Powerful astringent.
Treatment of
diarrhoea &
dysentery.
Dyeing & tanning
industry.
Resins:
•Resins are amorphous substance.
•These are mixture of essential oil and oxygenated products with terpenes &
carboxylic acid.
•They are translucent solids, semi-solids, or liquid substances.
•They are heavier than water which becomes soft when heated.
•They are electrically non-conductive.
•These are end products of metabolism which stores in schizogenous ducts or
glands.
•They are chemically organic acids or alcohols or esters and neutral resins.
•They are insoluble in water partially in light petroleum.
Benzoin Guggul Ginger
Synonym Sumatra benzoin,
Loban
Scented Bdellium,
Gum guggul,
Commiphora
weightii
Gingerin
Biological Source Balsamic resin
obtained from
styrax benzoin or S.
tonkinensis belongs
to family Styraceae
Oleogum resin-deep
incision- Stem bark
– Commiphora
weightii
Oleoresin-
Percolation –
Powdered rhizomes-
Zingiber officinale-
Zingiberaceae.
G. Source South eastern Asia,
Thailand
Africa India
Benzoin Guggul Ginger
Sumatra benzoin – free
balsamic acid (benzoic
and cinnamic acid)
Summaresinolic acid
Triterpenoid
Siaresinolic acid
Siam benzoin:
Coniferyl benzoate
Styrol, vanillin
Benzoic acid
 It is the simplest
aromatic carboxylic
acid.
Oleo gum devoid of
cinnamic acid and benzoic
acid
Terpenes – Myrcene or
caryophylline
Z-Guggulosterone
E-Guggulosterone
Guggulosterol-I,II,III.
Guggulosterone
 It is a phytosteroid.
Gingerin ( 18-35% Volatile
oil – ginger)
Gingerol
Zingerone, Shogaol
Gingerol
 Gingerol is a beta-
hydroxy ketone that is
5-hydroxydecan-3-one
substituted by a 4-
hydroxy-3-
methoxyphenyl moiety
at position 1.
Chemical constituents & Chemistry
Therapeutic uses & commercial Applications
Expectorant
Antiseptic
Compound tincture of
benzoin (inhalation
purpose)
Antiinflammatory
Antirheumatic
Hypolipidemic
hypocholestremic
Flavour in Carbonated
beverages, Spice.
Commercially,
Asafoetida Myrrh Colophony
Synonym Asafoetida, Gum asafoetida,
Devils dung
Bol, Gum
Myrrh, Myrrha
Rosin, Rosina,
Colophonium,
resin, Amber
resin, Pine Resin
Biological
Source
Oleogumresin – incision on
rhizomes and roots – Ferula
foetida – Umbelliferae
Oleo gum
resin-
commiphora
mol mol -
Burseraceae
Residue after
distillation of oil
from pinus sps -
Pinaceae
G. Source Central Asia Africa & Arab America, Pakistan
& India
Chemical
constituents
& Chemistry
Asaresinotannol (free) or commiphoric
acid
90% abietic acid
Therapeutic
uses &
commercial
Applications
Carminative, Intestinal
flatulence, powerful nervine
stimulant, flavouring agent
Stimulant,
antiseptic,
Mouth washes
& gargles
Diuretic,
Preparation of
ointments,
Varnishes, soaps,
printing inks.
GLYCOSIDES
Senna Bitter Almond
Synonym Tinnevelly Senna:
Senna leaf, Senai-ki-patti,
Tinnevelly senna
Alexandrian Senna:
Folia sennae Alexandrinae,
Cassia senna & Egyptian senna
Amygdala amara
Biological Source Tinnevelly Senna:
Dried leaflets – Cassia
angustilfolia-Leguminosae
Alexandrian Senna:
Dried leaflets – Cassia acutifolia-
Leguminosae
Dried ripened seeds –
Prunus amygdalus -
Rosaceae
Senna Bitter Almond
2 anthraquinone glycosides
Sennoside A & B; Sennoside B & C, rhein
8 diglucside
Aloe-emodin, rhein, Kaemferol.
2 naphthalene glycosides – Tinnevelley
glycoside
6 hydroxy musizin glycoside.
 Sennoside is a C- Glycoside.
 Sennoside is a diastereoisomeric
mixture containing sennoside A and
sennoside B.
40-50% fixed oil,
20% Proteins,
Enyzme – emulsion
Bitter glycoside – Amygdalin upon
hydrolysis gives 80% benzaldehyde and
2-6% hydrocyanic acid.
Amygdalin
 Amygdalin is a cyanogenic glucoside.
 Amygdalin is a cyanogenic
glycoside derived from the aromatic
amino acid phenylalanine.
Chemical constituents & Chemistry
Therapeutic uses
& commercial
Applications
Purgative in constipation.
The anthraquinones irritates and
stimulates the colon thereby
movements are increased due to
local action. The increase in
peristalsis causes reduction in
water absorption results in soft
& bulky faeces.
Produces gripping effect due to
emodin content.
Sedative due to
presence of hydrocyanic
acid,
Demulcent,
In perfumery &
Should not be used in
flavouring of foods.
Aloe
Cape Curacao Socotrine Zangiber
Synonym Aloe
Biological
Source
Solid residue obtained by evaporating the liquid – cut of leaves of
...... - Liliaceae
Aloe ferox Aloe barbadensis Aloe peryi
G. Source South Africe,
kenya
Island of
curacao
Island of
socotrine
zangiber
Chemistry
Principle constituent – Aloin
Barbaloin
Isobarbaloin
Aloe-emodin
Resins- Aloesin
Aloin B is a C-glycosyl compound.
Aloin extracted from natural sources is a mixture of two diastereomers, termed
aloin A (also called barbaloin) and aloin B (or isobarbaloin), which have similar
chemical properties.
Aloin is an anthraquinone glycosyl, meaning that its anthraquinone skeleton
has been modified by the addition of a sugar molecule.
Therapeutic uses
& commercial
Applications
Purgative,
Carminative, anti-inflammatory, treatment of burns &
wounds
Good moisturizing property
Antimicrobial hence used in cosmetic products.
Antiwrinkle property
Adulterant Natal aloes
Mocha aloes
Black catechu
Iridoids, Other terpenoids & Naphthaquinones
Iridoids:
•They are monoterpenes
•It consists of cyclopental pyranoid skeleton
•Iridoids are name after ants of Iridomermix genus from which were isolated
compounds involved in the defence mechanism of insects :iridoidal,
iridomyrmecin & related compounds.
•It is generally 10 carbons.
•It consists of glucoside – glycosidic linkage between OH group of anomeric carbon
of D-glucose and –OH group in the 1 position of aglycone.
•They are biosynthesized from acetate mevalonate pathway
•They are delicate due to their great instability.
Gentian
(Iridoid glycoside)
Artemisia
(Sesquiterpenoid)
Taxus
(Diterpenoid)
Synonym Indian gentian,
Kutki, Picrorrhiza
Sweet-annie, worm
weed, qninghao
Yew, Talispatra,
Himalayan Yew
Biological
Source
Dried rhizomes
Picrorhizza kurroa –
Scrophulariaceae
Herb – Artemisia
annua – Asteraceae
Dried leaves, bark &
roots – Taxus baccata,
T. Brevifolia, T.
Canadensis & T.
Cuspidate – Taxaceae
G. Source India, china China, Europe &
America
India, Canada &
America
Chemical
constituents
& Chemistry
Picroside I, II &
Kutkoside
Gentiopicroside
According to BP the
bitterness value
should not less than
NLT 10,000
Artemisinin
Deoxyartemisinin
Artemisinic acid
Amyrin
Luteolin
 It shows the
presence of lactone
ring & a peroxide
group.
 It is 8-hydroxy
santonin derivative
is responsible for
bitter taste of drug.
Taxol,
Cephalomannine, 10
deactyl baccatin III
Taxol
 It is a diterpenoid
(C20) alkaloidal
drug.
 The nitrogen atom
is not incorporated
in diterpene
skeleton
 The side chains in
taxol contain
aromatic rings
derived from
shikimic acid via
phenylalanine.
 It possess 4
membered oxetane
ring and complex
ester side chain in
their structures.
Therapeutic
uses &
commercial
Applications
Bitter tonic,
febrifuge, laxative,
antibacterial effect.
Traditionally used
in GIT infections,
anti-inflammatory &
wound healing.
Antimalarial, anti
HIV, anti-
inflammatory,
cytotoxic.
Anticancer
Lung carcinoma,
gastric and cervical
cancer and also
carcinomas head,
neck, prostate and
colon.
Carotenoids:
•They are the group of non-nitrogenous yellow, orange, or red pigments which are
widely distributed in living things.
•They are also called tetraterpenoids contains 8 isoprene units contains 40 carbon
atoms.
•They are over 600 known carotenoids.
•They are lipophilic compounds, soluble in oils and organic solvents.
•They can be isomerized by heat, acid & light.
•Many carotenoids exhibit spectral shifts with various agents and these spectral
changes are used for identification.
•Carotenoids are easily oxidized.
Types of carotenoids:
•It is classified into 2 classes.
•They are Cartenes & Xanthophylls
•Carotenes: They are purely hydrocarbons Ex: alpha carotene, beta carotene &
lycopene.
•Xanthophylls: They contains oxygen Ex: beta cryptoxanthin, lutein, zeaxanthin.
Carotenoid functions:
They are used as antioxidant, enhances immune function, UV skin protectant,
Provitamin A activity.
Lycopene:
Lycopene is a member of carotenoid gives characteristic red color to tomato,
watermelon and orange.
Xanthophylls:
The other type of carotenoid containing oxygen molecule (xanthophylls)
Source: Dark leafy greens such as spinach, broccoli.
Uses: antioxidant, cataracts.
Beta carotene:
It is known as provitamin A
Source: Yellow foods like carrot.
Chemistry:
It belongs to tetraterpenoids.
It contains 40 carbon atoms being built from 4 terpene units each containing 10
carbon atoms.
They take the form of polyene hydrocarbon chain which is terminated by rings,
may or may not have additional oxygen atoms attached.
The general structure of carotenoid is a polyene chain consisting of 9-11 double
bonds and possible terminating rings
General Structure of Carotenoids
Lycopene
Lutein

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UNIT-II PART IV.pptx

  • 1. INTRODUCTION Tannins: •These are the secondary metabolites which is in the form of a solution in cell sap or distinct vacuoles. •They are known as astringents from longtime. •Tannins are used in leather industry to prevent Putrefaction. Putrefaction is the final stage of death or decomposition. •They are chemically complex organic substances contains polyphenols. •They have high molecular weight. •They are devoid of N •They are non-crystalline substances. General Tests: •It precipitates alkaloids & gelatine. •Tannins are precipitated by salts of Cu, Sn & Pb. •Tannins are precipitated by chromic acid solution. •Tannins are precipitated by Fecl3 is bluish black or brownish green color.
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  • 3. Classification of Tannins: Based on the chemical nature or behaviour towards dry distillation process. They are divided into
  • 4. Black Catechu Pale Catechu Pterocarpus Synonym Cutch, Catechu, catechu nigrum Pale catechu, terra japonica, Gambier Bijasal, Indian kino tree, red sandal wook, rakta chandan B. Source Extract prepaed – heart wood of A. Catechu - Leguminosae Extract prepared – Leaves & young shoots – Uncaria gambier – Rubiaceae Dried juice – Ptercarpus marsupium – Leguminosae
  • 5. Chemical Composition & Chemistry Catechu tannic acid Acacatechin Small amoutns – Quercetin  Catechin is a flavan-3-ol, a type of natural phenol and antioxidant.It is a plant secondary metabolite. 7-33% catechins Catechutannic acid 22 -50% Quercitin Gambier – flourescin  Catechin is a flavan-3-ol, a type of natural phenol and antioxidant.It is a plant secondary metabolite. 70-80% Kinotannic acid Kino red K-Pyrocatechin Gallic acid Kinotannic acid is a glucosidal tannin. Kinored is anhydride of kinoin. Kinoin in the presence of oxidase enzyme it forms insoluble phlobaphene. It consists of santal Pterocarpin homopterocapin
  • 6. Therapeutic uses & Commercial Applications Dyeing & tanning industry Catechu is considered as one of the most potent herbal medicines use for anti- diarrhea and anti- ulcer Local astringent. Dyeing & tanning industry Catechu is included in mouthwashes and gargles used for gum disease (gingivitis), pain and swelling inside the mouth (stomatitis), sore throat, and mouth ulcers. Powerful astringent. Treatment of diarrhoea & dysentery. Dyeing & tanning industry.
  • 7. Resins: •Resins are amorphous substance. •These are mixture of essential oil and oxygenated products with terpenes & carboxylic acid. •They are translucent solids, semi-solids, or liquid substances. •They are heavier than water which becomes soft when heated. •They are electrically non-conductive. •These are end products of metabolism which stores in schizogenous ducts or glands. •They are chemically organic acids or alcohols or esters and neutral resins. •They are insoluble in water partially in light petroleum.
  • 8.
  • 9. Benzoin Guggul Ginger Synonym Sumatra benzoin, Loban Scented Bdellium, Gum guggul, Commiphora weightii Gingerin Biological Source Balsamic resin obtained from styrax benzoin or S. tonkinensis belongs to family Styraceae Oleogum resin-deep incision- Stem bark – Commiphora weightii Oleoresin- Percolation – Powdered rhizomes- Zingiber officinale- Zingiberaceae. G. Source South eastern Asia, Thailand Africa India
  • 10. Benzoin Guggul Ginger Sumatra benzoin – free balsamic acid (benzoic and cinnamic acid) Summaresinolic acid Triterpenoid Siaresinolic acid Siam benzoin: Coniferyl benzoate Styrol, vanillin Benzoic acid  It is the simplest aromatic carboxylic acid. Oleo gum devoid of cinnamic acid and benzoic acid Terpenes – Myrcene or caryophylline Z-Guggulosterone E-Guggulosterone Guggulosterol-I,II,III. Guggulosterone  It is a phytosteroid. Gingerin ( 18-35% Volatile oil – ginger) Gingerol Zingerone, Shogaol Gingerol  Gingerol is a beta- hydroxy ketone that is 5-hydroxydecan-3-one substituted by a 4- hydroxy-3- methoxyphenyl moiety at position 1. Chemical constituents & Chemistry Therapeutic uses & commercial Applications Expectorant Antiseptic Compound tincture of benzoin (inhalation purpose) Antiinflammatory Antirheumatic Hypolipidemic hypocholestremic Flavour in Carbonated beverages, Spice. Commercially,
  • 11. Asafoetida Myrrh Colophony Synonym Asafoetida, Gum asafoetida, Devils dung Bol, Gum Myrrh, Myrrha Rosin, Rosina, Colophonium, resin, Amber resin, Pine Resin Biological Source Oleogumresin – incision on rhizomes and roots – Ferula foetida – Umbelliferae Oleo gum resin- commiphora mol mol - Burseraceae Residue after distillation of oil from pinus sps - Pinaceae G. Source Central Asia Africa & Arab America, Pakistan & India Chemical constituents & Chemistry Asaresinotannol (free) or commiphoric acid 90% abietic acid
  • 12. Therapeutic uses & commercial Applications Carminative, Intestinal flatulence, powerful nervine stimulant, flavouring agent Stimulant, antiseptic, Mouth washes & gargles Diuretic, Preparation of ointments, Varnishes, soaps, printing inks. GLYCOSIDES Senna Bitter Almond Synonym Tinnevelly Senna: Senna leaf, Senai-ki-patti, Tinnevelly senna Alexandrian Senna: Folia sennae Alexandrinae, Cassia senna & Egyptian senna Amygdala amara Biological Source Tinnevelly Senna: Dried leaflets – Cassia angustilfolia-Leguminosae Alexandrian Senna: Dried leaflets – Cassia acutifolia- Leguminosae Dried ripened seeds – Prunus amygdalus - Rosaceae
  • 13. Senna Bitter Almond 2 anthraquinone glycosides Sennoside A & B; Sennoside B & C, rhein 8 diglucside Aloe-emodin, rhein, Kaemferol. 2 naphthalene glycosides – Tinnevelley glycoside 6 hydroxy musizin glycoside.  Sennoside is a C- Glycoside.  Sennoside is a diastereoisomeric mixture containing sennoside A and sennoside B. 40-50% fixed oil, 20% Proteins, Enyzme – emulsion Bitter glycoside – Amygdalin upon hydrolysis gives 80% benzaldehyde and 2-6% hydrocyanic acid. Amygdalin  Amygdalin is a cyanogenic glucoside.  Amygdalin is a cyanogenic glycoside derived from the aromatic amino acid phenylalanine. Chemical constituents & Chemistry
  • 14. Therapeutic uses & commercial Applications Purgative in constipation. The anthraquinones irritates and stimulates the colon thereby movements are increased due to local action. The increase in peristalsis causes reduction in water absorption results in soft & bulky faeces. Produces gripping effect due to emodin content. Sedative due to presence of hydrocyanic acid, Demulcent, In perfumery & Should not be used in flavouring of foods.
  • 15. Aloe Cape Curacao Socotrine Zangiber Synonym Aloe Biological Source Solid residue obtained by evaporating the liquid – cut of leaves of ...... - Liliaceae Aloe ferox Aloe barbadensis Aloe peryi G. Source South Africe, kenya Island of curacao Island of socotrine zangiber Chemistry Principle constituent – Aloin Barbaloin Isobarbaloin Aloe-emodin Resins- Aloesin Aloin B is a C-glycosyl compound. Aloin extracted from natural sources is a mixture of two diastereomers, termed aloin A (also called barbaloin) and aloin B (or isobarbaloin), which have similar chemical properties. Aloin is an anthraquinone glycosyl, meaning that its anthraquinone skeleton has been modified by the addition of a sugar molecule.
  • 16. Therapeutic uses & commercial Applications Purgative, Carminative, anti-inflammatory, treatment of burns & wounds Good moisturizing property Antimicrobial hence used in cosmetic products. Antiwrinkle property Adulterant Natal aloes Mocha aloes Black catechu
  • 17. Iridoids, Other terpenoids & Naphthaquinones Iridoids: •They are monoterpenes •It consists of cyclopental pyranoid skeleton •Iridoids are name after ants of Iridomermix genus from which were isolated compounds involved in the defence mechanism of insects :iridoidal, iridomyrmecin & related compounds. •It is generally 10 carbons. •It consists of glucoside – glycosidic linkage between OH group of anomeric carbon of D-glucose and –OH group in the 1 position of aglycone. •They are biosynthesized from acetate mevalonate pathway •They are delicate due to their great instability.
  • 18. Gentian (Iridoid glycoside) Artemisia (Sesquiterpenoid) Taxus (Diterpenoid) Synonym Indian gentian, Kutki, Picrorrhiza Sweet-annie, worm weed, qninghao Yew, Talispatra, Himalayan Yew Biological Source Dried rhizomes Picrorhizza kurroa – Scrophulariaceae Herb – Artemisia annua – Asteraceae Dried leaves, bark & roots – Taxus baccata, T. Brevifolia, T. Canadensis & T. Cuspidate – Taxaceae G. Source India, china China, Europe & America India, Canada & America
  • 19. Chemical constituents & Chemistry Picroside I, II & Kutkoside Gentiopicroside According to BP the bitterness value should not less than NLT 10,000 Artemisinin Deoxyartemisinin Artemisinic acid Amyrin Luteolin  It shows the presence of lactone ring & a peroxide group.  It is 8-hydroxy santonin derivative is responsible for bitter taste of drug. Taxol, Cephalomannine, 10 deactyl baccatin III Taxol  It is a diterpenoid (C20) alkaloidal drug.  The nitrogen atom is not incorporated in diterpene skeleton  The side chains in taxol contain aromatic rings derived from shikimic acid via phenylalanine.  It possess 4 membered oxetane ring and complex ester side chain in their structures.
  • 20. Therapeutic uses & commercial Applications Bitter tonic, febrifuge, laxative, antibacterial effect. Traditionally used in GIT infections, anti-inflammatory & wound healing. Antimalarial, anti HIV, anti- inflammatory, cytotoxic. Anticancer Lung carcinoma, gastric and cervical cancer and also carcinomas head, neck, prostate and colon.
  • 21. Carotenoids: •They are the group of non-nitrogenous yellow, orange, or red pigments which are widely distributed in living things. •They are also called tetraterpenoids contains 8 isoprene units contains 40 carbon atoms. •They are over 600 known carotenoids. •They are lipophilic compounds, soluble in oils and organic solvents. •They can be isomerized by heat, acid & light. •Many carotenoids exhibit spectral shifts with various agents and these spectral changes are used for identification. •Carotenoids are easily oxidized.
  • 22. Types of carotenoids: •It is classified into 2 classes. •They are Cartenes & Xanthophylls •Carotenes: They are purely hydrocarbons Ex: alpha carotene, beta carotene & lycopene. •Xanthophylls: They contains oxygen Ex: beta cryptoxanthin, lutein, zeaxanthin. Carotenoid functions: They are used as antioxidant, enhances immune function, UV skin protectant, Provitamin A activity. Lycopene: Lycopene is a member of carotenoid gives characteristic red color to tomato, watermelon and orange. Xanthophylls: The other type of carotenoid containing oxygen molecule (xanthophylls) Source: Dark leafy greens such as spinach, broccoli. Uses: antioxidant, cataracts.
  • 23. Beta carotene: It is known as provitamin A Source: Yellow foods like carrot. Chemistry: It belongs to tetraterpenoids. It contains 40 carbon atoms being built from 4 terpene units each containing 10 carbon atoms. They take the form of polyene hydrocarbon chain which is terminated by rings, may or may not have additional oxygen atoms attached. The general structure of carotenoid is a polyene chain consisting of 9-11 double bonds and possible terminating rings General Structure of Carotenoids