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8/14/2019 PHYTOCHEMICAL STUDY OF RESIN
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ADVANCED PHARMACOGNOSY
AND
PHYTOCHEMISTRY
SEMINAR ONPHYTOCHEMICAL STUDY OF RESIN
Supervised by: Inder makhija
Dr. M. Manjunath setty 090605015
Associate professor
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CONTENT
1. Introduction
2. Distribution of resin in plant
3. Properties of resin
4. Classification of resin
5. Isolation of resin
6. Estimation of resin
7. Biosynthesis of resin
8. Specific test for resin
9. Natural product containing resin
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INTRODUCTION
Resin are amorphous or transparent or translucent
solids, semisolid or liquid substance containing largenumber of carbon atom. They are usually formed in
schizogenous ducts or cavities and are end product of
metabolism.
Formation of resin: Generally the resin in plant is
formed in special passages or tubes called resin ducts.
These ducts are anastomose and so a single incision
can drain the resin from a considerable area of the plant.
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1) Physiologically produced resin
Plant which contain numerous resin ducts and
although tapping is necessary to drain the ducts
eg. Copaiba,
cannabis (glandular hair),
ginger (idioblast cell)
2) Pathologically produced resin
some plant do not have secretary structure, so
resin in these plant as a result of injury
eg. Balsam of tolu
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DISTRIBUTION OF RESIN IN
PLANT Distributed throughout the entire plant Kingdom,
specifically the spermatophyta i.e. the seed plants.
Notably, their present in almost rare and practically
negligible in the Pteridophyta i.e. the ferns and
their allies.
However, the resins have not been reported in the
Thallophyta i.e. the sea weeds, fungi etc.
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In general, the most important and extensively
studied resin containing families are namely:
Pinaceae(Colophony or
Rosin)
Leguminosae(Tolu balsam &Balsam of peru)
Dipterocarpaceae(Garijan -
balsam substitute
for Copaiba)
Burseraceae(Myrrh)
Umbelliferae(Asafoetida).
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PROPERTIES OF
RESINA. Physical propertiesAll resins are heavier than water.
They are usually hard, brittle, transparent or
translucent solids; some are slightly softsemisolids or liquid substances.
They are electrically non-conductive and
combustible masses. When heated they soften and fuse yielding a clear,
adhesive fluids.
They burn with smoky flame.
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B. Behaviour towards solvent
Resins are insoluble in water
Generally soluble in alcohol, ether, chloroform,acetone, carbon disulfide, solution of chloral
hydrate, fixed and volatile oils.
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RESINBASED ON CHEMICAL NATURE BASED ON
OCCURENCES
Resinacids
Resinalcohol
Resenes Glycoresin
Resinester
Copaiba
Ginger
Oleoresins
Asafoetida
Myrrh
Oleo-gum-resins
Balsum of peru
Balsam of tolu
Balsams
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A. Resin acids
E.g. i) , , and - Abetic acid (93%) colophony
iii) , , and - Commiphoric acid in myrrh
B. Resin alcohol
E.g. i) Benzoresinol from benzoinii) Storesinol from storax
Resinotannols :
E.g. i) Aloeresinotannol from aloeii) Peruresinotannol from balsam of peru
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C. Resenes
Complex neutral substance devoid of
characterizes chemical properties.
Do not form salts or esters , resist hydrolysis by
alkalies.
D. Glycoresins
E.g. Jalap and podophyllum
E. Resin esters
E.g. Benzyl benzoate in benzoin
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ISOLATION OF RESIN
1. By heating plant part
E.g. Guaiacum
A log of the wood is supported in a horizontal position
above the ground by two upright bars.
Log is then set on fire, large incision made in the middle
The melted resin runs out therefrom in considerable
abundance2. By processing the encrustations
E.g. Shellac is a resinous substance prepared from
an excretion from the bodies of scale insects of the
species.
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c) By percolation with alcohol and precipitation
with water.
E.g. podophyllum and ipomoea
d) By distillation for separation of oil.
E.g. copaiba and colophony
e) As plant exudates by incisions.
E.g. myrrh, asafoetida and balsams
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ESTIMATION OF RESIN
1) Estimation by Spectrophotometer: E.g. Guggul
a)Take 2.5g sample of guggul extract in 250ml R.B. flask
+ 0.5 N alcoholic KOH and reflux for 90 minutes.
b) Transfer the content of flask to a separator, Extract
with Petroleum ether .
c) Combine petroleum ether washings and wash withwater evaporate the petroleum ether and weigh the
residue.
d) Weigh accurately 0.1g of above residue and make it
to 10ml by spectrophotometric grade MeOH, Dilute 1ml of above solution to 10ml with MeOH and measure
absorbance at 327 nm using MeOH as blank.
Emax 1% cm path at 327 nm is 160.
E ti ti b N tit ti
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2) Estimation by Non-aqueous titration
E.g. Boswellia Serrata
a) Reagent
Dry DMF as solvent Standard 0.1 (N) potassium methoxide
Primary standard Benzoic acid AR
Indicator thymol blue
b) 200mg of powdered drug, take in conical flask +50ml of DMF and 4 drops of thymol blue indicator
c) solution titrated with 0.1 (N) potassium methoxide
solution till the blue end point. Blank titration wasperformed. Results obtained. Each ml of 0.1 (N)potassium methoxide 0.0456 gm of boswellicacid.
3) RP HPLC E g Podophyllotoxin
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3) RP
HPLC E.g.Podophyllotoxin
a) Plant material extracted thrice with MeOH,
b) The extracts were combined filtered and dried under vacuum.The concentrate was redissolved in HPLCgrade MeOH for
quantitative analysis.c) Methanol extract was resinified with acid H2O. The precipitated
resin was redissolved in HPLC grade MeOH.
Column used: Lichrosper Flow rate : 1 ml / min
Run time: 20 min Detection wavelength: 230nm
Solvent system: Acetonitrile : H2O (4:6)
d) Podophylloltoxin content analysis in the extract and resin was
performed by the extract standard MeOH, using purepodophyllotoxin as standard.
Peak area percentages and extinction co-efficient were calculatedfrom chromatograms of standard detected at 230nm.
TESTS FOR SPECIFIC RESINS
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TESTS FOR SPECIFIC RESINS
Benzoin: a) To 2.5gm benzoin, add 10ml of ether, shakeit well and pour 2-3 ml of this extract in a porcelain dish,
add 2-3 drops H2SO4.deep brown colour= sumatra benzoin
deep purplish red colour = Siam benzoin.
Colophony: a) Dissolve colophony in light petroleumether and double the volume with dilute solution of copperacetate, petroleum layer takes emerald green colour(dueto copper salt of abietic acid)
Myrrh: a) Triturated with water yellowish emulsion
b) Dry ethereal extract when treated with bromine vapourreddish in colour
OS S S O S CO O S
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BIOSYNTHESIS OF RESIN COMPONENTS
The exact chemical identity of most constituents of
resin mixtures is unknown, thus detailed
information on the biosynthesis of these plantconstituents is necessary lacking.
Many resin components are considered to arise byoxidation of polymerized terpenoid metabolites. It
is known that acetate and mevalonate are
incorporated into some resins. Biosynthesis of capsaicin from phenyl propanoid
pathway and valine pathway
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Sr.No. Name of drug and
synonym
Biological source Active constituents
1. Podophyllum resin Podophyllum hexandrum
P. emodi (Berberidaceae)
Resin,
podophyllotoxin
2. Colophony Pinus species (Pinaceae) Resin acids, abietic
acid, resene
3. Jalap Ipomoea purga
(Convolvulaceae)
Resin, volatile oil,
jalapin, convolvulin
4. Cannabis Cannabis sativa
(Cannabinaceae)
Resin,
tetrahydrocannabinol
OLEORESIN
1. Ginger Zingiber officinale
(Zingiberaceae)
Gingerol, shogaol,
zingerone
2. Capsicum - Capsicum annum
(Solanaceae)
Capsanthin, capsaicin
3. Copaiba Copaifera species
(Leguminosae)
resin acids
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OLEO-GUM RESINS
1. Myrrh Comm iphora mo lmol
(Burserraceae)
Volatile oil, gum, resin,
commiphoric acids
2. Asafoetida Ferula foetida (Umbelliferae) asaresinotannol
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BALSAMSSr.No. Name of drug and synonym Biological source Active constituents
1. Benzoin -Styrax benzoin
(Sumatra benzoin),
Styrax tonkinensis
(Siam benzoin)
(styraceae)
Benzoic and
cinnamic acids and
their esters,
sumaresinolic and
siaresinolic acid,
coniferyl acetate
2. Tolu balsam Myroxylon
balsumum
(Leguminaceae)
Cinnamic acid,
benzoic acid,
benzoyl benzoate,toluresinotannol,
volatile oil
3. Storax Liquidamber
orientalis
(Hamamelidaceae)
Resin (storesin) free
and cinnamic ester
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REFERENCE
A Textbook of Pharmacognosy by T.C. Denston;5th edition 1950; page no. 469-472
Pharmacognosy by Edward.P.Claus, V.E.Tyler,L.R.Brady; 6th edition 1970; page no. 201-219
The Practical Evaluation of Phytopharmaceuticalsby K.R.Brain and T.D.Turner; page no. 60, 145
British Pharmacopoeia; vol-1 2005; page no. 231
Modern Pharmacognosy by T.E.Wallis; 5th
edition1985; page no-483-485
Pharmacognosy by C.K.Kokate, A.P.Purohit,S.B.Gokhale; 22nd edition 1990; page no-392-395
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THANK YOU