Resins

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Objective
At the end of this chapter students will be able to:
⚫ define and classify resins

⚫ identify resins

⚫ mention their use

⚫ describe their physical and chemical characteristics

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Introduction
⚫ Resins are solid or semi-solid amorphous products of complex chemical nature.
⚫ They are considered as end products of metabolism, and are believed to arise by
oxidation of polymerized terpenoids metabolites forming complex mixtures
⚫ They are simply extractions of plant material, are taken either from
⚫ the whole plant or
⚫ from specific parts of the plant (bark of trees, flowers of herbs, and buds of shrubs)

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Occurrence
⚫ Resins can be obtained from plant and animal sources are known as natural
sources resins.
⚫ They are found inside plants or are exuded by plants, such as sap, latex, or
mucilage forms.
⚫ It can be either in the internal part or on the surface of different parts of the plant.
⚫ They are obtained in different parts of plants
⚫ Resin Cell – Ginger
⚫ Glandular Hair – Cannabis
⚫ Schizogenous or Schizolysigenous Duct or Cavities – Pinewood
⚫ Induced at a Site of Injury / Incision - Benzoin

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⚫ Some examples of plant source resins are Asafoetida, Myrrh, Balsam,
Benzoin, Ginger, Colophony, Jalap, Podophyllum, etc.
⚫ Some examples of animal source resins are Shellac or Lac.
⚫ Sometimes animal and plants resins are obtained from fossils, they are
known as fossilized resin. Example: Amber which is fossilized tree resin,
often known as Copal.

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Properties
⚫ These are transparent or translucent solid or semisolid.
⚫ They are brittle solid.
⚫ They are fusible and flammable organic substances.
⚫ The specific gravity of Resins is more than water. Therefore, these are heavier
than water
⚫ They are soluble in volatile oils, ether, and alcohol.
⚫ They generally become soft at heating. On further heating, Resins will be melted
⚫ These compounds are highly enriched with carbon.
⚫ On storage, resins undergo a slow oxidation process in the atmosphere and
become dark in color.

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Chemistry
⚫ The resin produced by most plants is a viscous liquid, composed mainly of
volatile fluid terpenes, with lesser components of dissolved non-volatile solids
which make resin thick and sticky
⚫ The common terpenes in resin are the bicyclic terpenes alpha and beta-pinene and
sabinene, the monocyclic terpenes limonene and terpinolene, and smaller
amounts of the tricyclic sesquiterpenes.
⚫ Resins are enriched with carbon, deprived of nitrogen and contain oxygen.
⚫ Resins generally form soap when boiled with alkali.
⚫ They are associated with volatile oils (oleoresins), with gum (gum resins), or with
oil and gum (oleo-gum resins).
⚫ Electrically they are non-conductive masses

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How is Resin Made?

Based on their formation:

⚫ Physiological Resin: These types of Resins are formed by the normal metabolism
process. Example - cannabis, podophyllum, and ginger.
⚫ Pathological Resin: These types of Resin are formed by the result of the wound,
injury, or abnormal circumstances. Example - benzoin, asafoetida, and guggul.

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Classification of Resins

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Taxonomical Classification
The resins are grouped according to their botanical origin exclusively, such as:
• Coniferous Resins: e.g., Colophony, Sandarac;

• Berderidaceae Resins: e.g., Podopyllum and

• Zygophyllaceae Resins: e.g., Guaiacum

⚫ In this particular instance, it has been observed that the resins that usually occur in
plants of the same natural order, may exhibit more or less related characteristics
features.

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Resin combination
Classification of Resin is based on the nature of occurrence with other secondary
metabolites.
➢ Oleoresin- These are naturally occurring Resin, which is a mixture of Resin and
volatile oil. posses an essence due to volatile oils.
➢ Eg. capsicum, ginger, and copaiba.
➢ Gum Resin- These types of Resins are associated with the gum.
➢ Due to solubility in water, gums can be easily separated out from resin
by dissolving the gum in water
Eg. colophony and cannabis. Ammoniacum is an example of natural gum resin.

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➢ Oleo Gum Resins- These types of Resins are a mixture of volatile oil, gum, and
Resin.
➢ Eg turmeric, asafoetida, and myrrh.
➢ Balsams- These types of Resin are a mixture of benzoic acid and cinnamic acid
or esters of these acids.
➢ It can occur in free or combined form.
➢ Eg. benzoin, tolu balsam, Peru balsam.
➢ Glyco Resin- This type of Resin occurs in combination with sugar.
➢ Eg. jalap and podophyllum

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 Chemical classification
Classification on the basis of chemical
constituents:
⚫ Acid resin- are mixtures of large
proportion of diterpenoid oxyacids,
carboxylic acids and phenolic acids
⚫ Found in free states or as the esters
derivatives.
⚫ They combine with alkali and their
metallic salts are termed as
resonates.
⚫ With aqueous solution of alkali they
form soap like solution or colloidal
suspension.
⚫ Eg: abietic acid (colophony),
copaivic acid and oxycopaivic acid
(copiba), primaric acid (fankicense)
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Resin alchohol-
⚫ These are complex alcohols of high molecular weights

⚫ present in free state or as ester of simple aromatic acids like benzoic acid,
cinnamic acid, and salicylic acid
⚫ Resin alcohols are further subdivided into:

I. Resinotannols (resin phenols)

⚫ have tannin like properties and form blue color with ferric chloride

Eg: Aloeresinotannol from aloe

II. Resinols
⚫ are high molecular weight non phenolic alcohols which do not give tannin
reaction with iron salts
Eg: Benzoresinol from benzoin
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⚫ Ester resins- these are esters of resin alcohol or resinotannol combined with
resin acid or balsamic acid.
Eg: cinnamyl cinnamate from storax
⚫ Resenes- these re the neutral and inert substances as they do not contain
characteristic functional group
Eg: Asafoetida contains drug about 50% of asaresene B.

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Uses
⚫ In bronchia asthma (Cannabis)
⚫ It is used as an anticancer drug (podophyllum)
⚫ They are local irritant and act as local cathartics (Jalap and Ipomea)
property.
⚫ It is used as a stimulant or diuretic agent.
⚫ It is used as an anti-inflammatory property.
⚫ Used externally as mild antiseptic in the form of tinctures (Benzoin)
⚫ Resins are used as a carminative agent.
⚫ It is used as an expectorant.
⚫ These are used as flavoring agents.
⚫ It is also used for bow treatments for instruments like cellos and violins

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Preparation of Resins

⚫ So far, no general method has either been suggested or proposed for the
preparation of resins.
⚫ In fact, there are two categories of resinous products, namely: (a) Natural Resins;
and (b) Prepared Resins
A. Natural Resins:
⚫ These resins usually formed as the exudates from various plants obtained either
normally or as a result of pathogenic conditions (i.e., by causing artificial
punctures), such as: mastic, sandarac.
⚫ These are also obtained by causing deep incisions or cuts in the trunk of the plant,
for instance: turpentine.
⚫ They may also be procured by hammering and scorching, such as: balsam of
Peru.
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B. Prepared Resins:
⚫ The resins obtained here are by different methods as described below:

⚫ (i) The crude drug containing resins is powdered and extracted with ethanol several
times till complete exhaustion takes place. The combined alcoholic extract is either,
evaporated on water-bath slowly in a fuming cup-board or poured slowly into cold
distilled water.
⚫ The precipitated resin is collected, washed with cold water and dried carefully under
shade or in a vacuum desiccator.
⚫ Examples: Podophyllum; Scammony and Jalap

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⚫ (ii) In the case of alco-resins, organic solvents with lower boiling points are normally
employed e.g., solvent ether (bp 37°C); acetone (bp 56.5°C), for their extraction.
However, the volatile oil fraction can be removed conveniently through distillation
under vacuo.
⚫ (iii) In the instance of gum-resins, the resin is aptly extracted with 95% (v/v) ethanol
while leaving the insoluble gum residue in the flask (or soxhlet thimble).

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Extraction and isolation
⚫ Pharmaceutical resins are obtained from the plants and animals by one of the
following methods:
⚫ By extraction with alcohol and precipitation with water, e.g. jalap,
podophyllum,…etc.
⚫ By distillation for separation of oil, e.g. copaiba, colophony,…etc.
⚫ By heating the plant part, e.g. guaiacum.
⚫ As plant exudates by incisions, e.g. myrrh, asafoetida, balsams,…etc.
⚫ By collecting fossil resins, e.g. copal, kauri,…etc.
⚫ By processing the encrustations i.e. shellac

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Drugs Containing Resins

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1. Podopyllum
⚫ The term is derived from ancient Greek word means `foot leaf'
⚫ also known as Mayapple because of its fruits ripen in
spring
⚫ The genus Podophyllum is generally represented by two
species:
⚫ P. hexandrum - Himalayan Mayapple
⚫ P. peltatum - American Mayapple
⚫ P. peltatum contains lower amounts of resin in comparison to P.
hexandrum

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Podopyllum Cont…
P. hexandrum P. peltatum

⚫ Podophyllum is an endangered but high value medicinal

plant from temperate and cold climatic zones of the globe
⚫ It has wide scope of organized scientific study on its
different aspects Hiwot A. ([Link], MSc.), August, 2022 23
Uses
⚫ Podophyllin (a crude resin)

⚫ vermifuge and emetic

⚫ purgative
⚫ antitumour properties Podophyllotoxin
⚫ Podophyllotoxin,
⚫ blocks polymerization of tubules into
microtubules, leading to an arrest of mitosis
and thus resulting in destruction of the warts.
⚫ developed to be anticancer agents

-Peltatin, R = CH3
-Peltatin, R = H

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Derivatives of Podophylotoxin
1. Etoposide
⚫ Lignan derivative obtained semi-synthetically from
podophyllotoxin
⚫ Used in the treatment of small-cell lung cancer, testicular
cancer, lymphomas and leukaemias

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Derivatives Cont…
2. Teniposide
⚫ Thenylidene derivative

⚫ Used in the treatment of paediatric cancer: lymphocytic leukaemia,

brain tumours

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2. Ginger
Geographical sources
• Jamaica
• China
• India
• Africa

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Constituents
⚫ Volatile oils (1 – 2%)
⚫ Camphene
⚫ Cineole
⚫ Citral
⚫ Borneol
⚫ Sesquiterpene HC’s
⚫Zingiberene & Zingiberol (Sesquiterpene alcohol)
⚫ Resins
⚫ Gingerols – pungent component – Anti-inflammatory
⚫ Shogaols – increases bile secretion
⚫ Starch
⚫ Mucilage Hiwot A. ([Link], MSc.), August, 2022 28
Chemical Structures

⚫ Gingerols are a homologous series of phenols

⚫ The most abundant is [6]-gingerol

⚫ The pungency of dry ginger mainly results from shogaols

which are dehydrated forms of gingerols

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Uses and Actions
⚫ Actions
⚫ Carminative
⚫ Stimulant
⚫ Anti-emetic
⚫ Anti-bacterial & Anti-fungal
⚫ Gingerol – pungent component – Anti-inflammatory
⚫ Shogaols– increases bile secretion & enhanced GIT activity
⚫ Uses
⚫ Motion Sickness
⚫ Morning Sickness

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3. Capsicum
⚫ is the dried ripe fruit of Capsicum frutenscens, known in commerce African
chilies, C. annum, known in commerce Tabasco pepper

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Chemical Constituents
⚫ capsaicinoids
⚫ volatile oils (1.5%)
⚫ fixed oil
⚫ carotenoids
⚫ ascorbic acid

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Capsaicinoids
⚫ Capsaicinoids are considered the active ingredients of OC.
⚫ Capsaicinoids are isolated through a solvent extraction of the dried, ripened fruit
of chili peppers then dried, and compounded together
⚫ The final oleoresin contains several branched-chain alkyl vanillylamides, in
addition to capsaicin, the major component in OC.
⚫ Cause the spicy flavor (pungency) of chili pepper fruit
⚫ The predominant capsaicinoid components of OC are capsaicin (70%),
dihydrocapsaicin (20%), norhydrocapsaicin (7%), homocapsaicin (1%), and
homodihydrocapsaicin (1%)

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Uses
⚫ culinary importance
⚫ used medicinally in creams to counter neuralgia and in
other topical pain-relieving preparations
⚫ The initial burning effect of capsaicin is found to
affect the pain receptors, making them less
sensitive
⚫ antioxidant, anticarcinogenic , promotion of energy
metabolism and suppression of fat accumulation , and
anti-inflammatory

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Myrrh
⚫ oleo-gum resin exudates obtained from
several species in the genus Commiphora
⚫ Mainly harvested from Commiphora myrrha,
a low growing, desert tree that exudes a
viscous yellow gum, which hardens into a
reddish-brown resin.
⚫ It contains :
⚫ 57–61% water-soluble gum

⚫ 7–17% volatile oils

⚫ 25–40% alcohol-soluble resins and

⚫ 3–4% impurities

⚫ The name myrrh is derived from the Arabic

and Hebrew word mur, which means bitter
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Chemistry
⚫ The alcohol-soluble resins of myrrh consist of:
⚫ commiphoric acids

⚫ commiphorinic acid

⚫ heeraboresene

⚫ heerabomyrrhols

⚫ commiferin……

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 Chemistry Cont…
⚫ The volatile oil fraction contains:
⚫ Terpenes, elemol
⚫ cinnamaldehyde
⚫ cuminaldehyde
⚫ cumicalcohol
⚫ eugenol, heerabolene,
⚫ limonine, dipentene, pinene....
⚫ Its characteristic odor is due to the furanosesquiterpenes
⚫ The water-soluble gum or mucilage fraction is composed
mainly of acidic polysaccharide with galactose, xylose, 4-
O-methyl-glucuronic acid and arabinose

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Uses
⚫ food, flavor, liqueur and beverage, cosmetics, perfumery and others.
⚫ frankincense and myrrh have several local applications in medicinal, hygienic, and
insecticide areas that could be developed through research
⚫ Myrrh has been shown anti-inflammatory, antipyretic and antimicrobial activity that
work in two ways:
▪ it stimulates the production of white blood corpuscles (with their anti-
pathogenic actions)
▪ it has a direct anti-microbial effect

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4. Cannabis

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Cannabis
⚫ is the general name given to a variety of substances prepared from the
plant Cannabis sativa
⚫ In small doses, it is classified as a depressant
⚫ In larger doses, it can be an hallucinogen
⚫ The dried plant, resin or oil is commonly smoked for recreational
purposes
⚫ can also be ingested by cooking it in food
⚫ is also called 'gunga', 'dope', 'hash', 'weed', 'hemp', 'grass' and 'mull‘
⚫ is normally a dioecious plant

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History
⚫ Cannabis is among the very oldest of economic plants,
providing fiber, edible seed, and drug resin

1st archaeological evidence Used in Europe

of hemp use Ritual use
in India Used semi-
Medical use Hashish use in legal in
in China Arab world CA/AZ

8000 BC 2700 BC 2000 BC 1000 AD 1850s 1996

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 Why do people use cannabis?
To experience euphoria or perceptual distortions because various
mental and physical effects.
To relieve mental symptoms
⚫ negative symptoms of schizophrenia
⚫ anxiety
To relieve physical symptoms
⚫ eg nausea, anorexia, cancer & HIV
Medical cannabis: the use of cannabis to treat disease or improve
symptoms.

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Forms and Preparations
Marijuana
⚫ the dried leaves and flowers (buds) of the cannabis plant that are
smoked in a joint or a bong.
⚫ most common form

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“Bubble Gum” “Big Bud” “Dutch Northern Lights”
Forms and Preparations
⚫ Hashish
⚫ dried resin from top of female plant
⚫ that is usually mixed with tobacco and somoked or added to foods
⚫ THC usually 2-5%, but up to 15%
⚫ Hash Oil
⚫ organic extraction
from hashish
⚫ THC usually ~ 10-20%
up to 70%

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Effects on Behavior
Low - moderate doses
⚫ disinhibition, relaxation, drowsiness
⚫ feeling of well being, exhileration, euphoria
⚫ sensory - perceptual changes
⚫ recent memory impairment
⚫ balance/stability impaired
⚫ decreased muscle strength, small tremor
⚫ poor on complex motor tasks (e.g., driving)

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Hiwot A. ([Link], MSc.), August, 2022 48
Effects on behavior
High doses
⚫ pseudohallucinations
⚫ synesthesias
⚫ impaired judgement, reaction time
⚫ pronounced motor impairment
⚫ increasingly disorganized thoughts, confusion, paranoia, agitation

Not lethal even at very high doses

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Pharmacokinetics
Absorption
⚫ very lipid soluble
⚫ good absorption if smoked (20-37%)
⚫ rapid peak
⚫ slow absorption with oral

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Cannabinoids
⚫ a group of terpenophenolics compounds that are
pharmacologically active compounds
⚫ over 65 (delta-9-tetrahydrocannabinol (Δ 9-THC), Δ 8-THC,
CH 3

cannabinol, etc.) OH

H 3C
CH 2 CH 2
H 3C O CH 2 CH 2 CH 3
9-Tetrahydrocannabinol

⚫ The FDA has not approved the cannabis plant for any medical
use, however it approved several drugs that contain individual
cannabinoids.
⚫ Epidiolex, which contains a purified form of CBD derived from
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cannabis, was approved for the treatment of seizures associated
 Some Common Cannabinoids
In the plant: In your body Synthetic:
(endogenous):

Δ9 – THC 2-arichidonyl CP 55,940

glycerol (2 – AG)

Δ8 – THC anandamide HU – 210

cannabidiol and
cannabinol

Structure of THC and synthetic analogs

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Hiwot A. ([Link], MSc.), August, 2022 53
Mode of Cannabis Action
⚫ Two specific cannabinoid receptors
⚫ CB1 - brain and peripheral tissues
⚫ CB2 - immune system

⚫ Linked to G-proteins with diverse downstream signalling pathways

⚫ Euphoria results from stimulation of mesolimbic dopaminergic neurons, like other

drugs of abuse

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 Cannabinoid receptor (CB1) distribution

Cannabinoid receptors are localized in areas that control movement (basal

ganglia, cerebellum), cognition (cerebral cortex), and attention and memory
(hippocampus).

Cannabinoid receptors are notably sparse in areas that control heart rate and
respiration (medulla), explaining why there are not fatal overdoses of marijuana.

Cannabinoid receptors are also located in areas that control emesis (nucleus of
the solitary tract) and pain, suggesting medical potential of marijuana.
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Cannabinoid receptor
antagonists

SR 141716
(Rimonabant),
LY320135 and AM281
All have marked
selectivity for CB1
receptors over CB2

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Metabolism
⚫ rapid initial drop due to redistribution to fats
⚫ slower metabolism in liver
⚫ metabolites may persist for a week

Major biolgically active

compound may be metabolite
1. Primary metabolic product of  9-THC
(11-OH-  9-THC) is more potent than  9-THC
2. Delay between peak plasma levels and “high”
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 Therapeutic use of Cannabinoids
Registered products
Promising indications: Dronabinol (Marinol®)
controlling nausea and vomiting (cancer, For severe nausea and vomiting
HIV) associated with cancer
stimulating appetite (cancer, HIV)
slight spasticity with pain (multiple
chemotherapy.
sclerosis) For the treatment of AIDS-related
(chronic) pain anorexia
Gilles de la Tourette’s syndrome Nabilone (Cesamet®)
asthma
extra pyramidal symptoms
For severe nausea and vomiting
therapy resistant glaucoma associated with cancer
chemotherapy

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Potential medical uses
⚫ Glaucoma (increased intraocular pressure)
⚫ Antiemetic (reduce nausea and vomiting)
⚫ Anticonvulsant
⚫ Enhance appetite (e.g., AIDS patients)
⚫ Analgesic

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