ADVANCED PHARMACOGNOSY AND PHYTOCHEMISTRY

SEMINAR ON

PHYTOCHEMICAL STUDY OF RESIN

Supervised by: Dr. M. Manjunath setty Associate professor

Inder makhija 090605015

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

Resin are amorphous or transparent or translucent solids, semisolid or liquid substance containing large number 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.

INTRODUCTION

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

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.

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).

PROPERTIES OF
RESIN
A. Physical properties All resins are heavier than water. They are usually hard, brittle, transparent or translucent solids; some are slightly soft semisolids 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.

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.

C. Chemical properties

Resins are complex mixtures of different type of substances; these include acids, esters, glycosidic bodies and in different substances called as resenes. The element nitrogen does not enter into the composition of any resin constituent. Many resins when boiled with alkalies yield soaps which are termed resin soaps.

CLASSIFICATION OF RESIN
BASED ON CHEMICAL NATURE OCCURENCES BASED ON

Resin acids

Resin alcohol

Oleoresins

Copaiba Ginger
Asafoetida Myrrh Balsum of peru Balsam of tolu

Resenes

Glycoresin

Oleo-gumresins

Resin ester
Balsams

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 benzoin ii) Storesinol from storax

Resinotannols :
E.g. i) Aloeresinotannol from aloe ii) Peruresinotannol from balsam of peru

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

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 abundance 2. By processing the encrustations E.g. Shellac is a resinous substance prepared from an excretion from the bodies of scale insects of the species.

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

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 with water 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 1 ml 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.

Estimation by Non-aqueous titration E.g. Boswellia Serrata a) Reagent

2)

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 was performed. Results obtained. Each ml of 0.1 (N) potassium methoxide 0.0456 gm of boswellic acid.

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 HPLC grade 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 pure podophyllotoxin as standard. Peak area percentages and extinction co-efficient were calculated from chromatograms of standard detected at 230nm.

TESTS FOR SPECIFIC RESINS

Benzoin: a) To 2.5gm benzoin, add 10ml of ether, shake it 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 petroleum ether and double the volume with dilute solution of copper acetate, petroleum layer takes emerald green colour (due to copper salt of abietic acid) Myrrh: a) Triturated with water yellowish emulsion

b) Dry ethereal extract when treated with bromine vapour reddish in colour

BIOSYNTHESIS OF RESIN COMPONENTS The exact chemical identity of most constituents of resin mixtures is unknown, thus detailed information on the biosynthesis of these plant constituents is necessary lacking. Many resin components are considered to arise by oxidation 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

Sr.No.
1.

Name of drug and synonym

Podophyllum resin

Biological source
Podophyllum hexandrum P. emodi (Berberidaceae) Pinus species (Pinaceae) Ipomoea purga (Convolvulaceae) Cannabis sativa (Cannabinaceae)

Active constituents
Resin, podophyllotoxin Resin acids, abietic acid, resene Resin, volatile oil, jalapin, convolvulin Resin, tetrahydrocannabinol

2. 3. 4.

Colophony Jalap Cannabis

OLEORESIN
1. 2. Ginger Capsicum Zingiber officinale (Zingiberaceae) - Capsicum annum (Solanaceae) Gingerol, shogaol, zingerone Capsanthin, capsaicin

3.

Copaiba

Copaifera species (Leguminosae)

resin acids

OLEO-GUM RESINS
1. Myrrh Commiphora molmol (Burserraceae) Volatile oil, gum, resin, commiphoric acids

2.

Asafoetida

Ferula foetida (Umbelliferae)

asaresinotannol

BALSAMS
Sr.No. Name of drug and synonym Biological source Active constituents

1.

Benzoin

-Styrax benzoin (Sumatra benzoin), Styrax tonkinensis (Siam benzoin) (styraceae)

Myroxylon balsumum (Leguminaceae)

Benzoic and cinnamic acids and their esters, sumaresinolic and siaresinolic acid, coniferyl acetate
Cinnamic acid, benzoic acid, benzoyl benzoate, toluresinotannol, volatile oil Resin (storesin) free and cinnamic ester

2.

Tolu balsam

3.

Storax

Liquidamber orientalis (Hamamelidaceae)

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 Phytopharmaceuticals by 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 edition 1985; 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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