ADVANCED PHARMACOGNOSY AND PHYTOCHEMISTRY

SEMINAR ON

“PHYTOCHEMICAL STUDY OF RESIN”

Supervised by: Inder makhija

Dr. M. Manjunath setty 090605015

Associate professor

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

INTRODUCTION

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.

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 BASED ON

OCCURENCES

Resin acids

Resin alcohol

Resenes Glycoresin

Resin ester

• Copaiba

• Ginger Oleoresins

• Asafoetida

• Myrrh Oleo-gum-

resins

• Balsum of peru

• Balsam of tolu Balsams

A. Resin acids

E.g. i) α, β, and γ- Abetic acid (93%) colophony

iii) α, β, and γ- 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.

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 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. 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

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)

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

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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