resin and resin combinations

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RESINS AND RESIN COMBINATIONS :

RESINS AND RESIN COMBINATIONS DR. NAUREEN SHEHZADI DEPARTMENT OF PHARMACEUTICAL SCIENCES, FACULTY OF PHARMACY, SUPERIOR UNIVERSITY

CONTENTS OF PRESENTATION:

CONTENTS OF PRESENTATION Definition Occurrence in the plants Formation of resins in the plants Physical properties Chemical properties Preparation of resins Importance to the plants C omposition of resins Combinations of resin Classes and their representatives Resins: Rosin, Cannabis Glycoresins: Podophyllum, Jalap, Ipomoea, Colocynth Oleoresins: Terpentine, Capsicum, Ginger Oleo-gum resins: Asafoetida, Myrrh Balsams: Storax, Peruvian balsam, Tolu balsam, Benzoin

DEFINITION:

DEFINITION Resins are solid or semi-solid, amorphous products derived from natural living sources and are mostly from the plant origin (exception is shellac that is obtained from the secretions of insect) Resins are the secondary metabolites produced by higher plants and are nothing but oxidative products of terpenes. They may also be regarded as the end-products of destructive metabolism.

OCCURRENCE IN PLANTS:

OCCURRENCE IN PLANTS In plants, resins usually occur in different secretory zones or structures e.g. Ducts and cavities (Schizogenous and Schizolysigenous ducts) Resin cells Glandular hairs Occurrence Example Resin cells Ginger Ducts and cavities Pine wood Glandular hair Cannabis Sometimes, resins do not occur in specialized cells but are impregnated in all the elements of a tissue (e.g. Guaiacum resin is obtained from the heartwood of the plant; it is found in the vessels, fibres, medullary ray cells and woody parenchyma)

FORMATION OF RESIN IN PLANTS:

FORMATION OF RESIN IN PLANTS The formation of the resins in the plant is by virtue of its normal physiological functions. However, its yield may be enhanced in certain exceptional instances e.g. by inflicting injury to the living plant (e.g. Pine).

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Many resinous products are not formed by the plant itself unless and until purposeful and methodical injuries in the shape of incisions are made on them and secretions or plant exudates are tapped carefully (e.g. Tolu balsam)

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In some exceptionally rare instances, the resin occurs as a result of sucking the juice of the plants by scale insects and converting the sucked juice into the resinous substance that ultimately covers the insect itself and twigs of the plant (e.g. Laccifer lacca-shellac )

PHYSICAL PROPERTIES:

PHYSICAL PROPERTIES Hard Amorphous solids/semi-solids Translucent/transparent Tasteless or have little taste Heavier than water Complex mixture of allied substances e.g. resin acids, resin alcohols, resin esters, resinotannols and glucoresin etc. Fusible (upon heating, soften first and then melt forming either an adhesive or a sticky massive fluid, without undergoing any sort of decomposition or volatilization) Resins are bad conductors of electricity, but when rubbed usually become negatively charged.

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On being heated in the air i.e., in the presence of oxygen, resins usually burn readily with a smoky flame by virtue of the presence of a large number of C-atoms in their structure) On being heated in a closed container i.e., in the absence of oxygen, they undergo decomposition and very often give rise to empyreumatic products i.e., products chiefly comprising of hydrocarbons. They are practically insoluble in water , but frequently soluble in polar organic solvents e.g. ethanol, ether and chloroform (these form their respective solutions in these organic solvents which on evaporation, leave behind a thin-varnish-like film deposit), freely soluble in many other organic solvents e.g. acetone, n-hexane, benzene, carbon disulphide, as well as in fixed oils and volatile oils, dissolve in chloral hydrate solution , normally employed for clarification of certain sections of plant organs and usually insoluble in petroleum ether (a non-polar solvent) but with a few exceptions (colophony freshly powdered)

CHEMICAL PROPERTIES:

CHEMICAL PROPERTIES Resins are found to be a mixture of numerous compounds rather than a single pure chemical entity and their chemical properties are exclusively based upon the functional groups present in these substances. Resins, in general, are enriched with carbon (hydrocarbon compounds), deprived of nitrogen and contain a few oxygen in their respective molecules. Majority of resins undergo slow atmospheric oxidation whereby their color get darkened and solubility is impaired. The acidic resins when treated with alkaline solutions they yield soaps (or resin-soaps). The solutions of resins in alkalis distinctly differ from ordinary soap solutions by virtue of the fact that the former cannot be easily ‘salted-out’ by the addition of NaCl, unless it is used in large excess quantity.

PREPARATION OF RESINS:

PREPARATION OF RESINS Until now, no specific method is either proposed or suggested for the preparation of resins. In fact, there are two categories of resinous products; Natural Resins Prepared Resins This classification forms the basis of the methods employed in the preparation of the two aforesaid resins.

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Natural Resins These resins usually formed as the exudates from various plants obtained either normally or as a result of pathogenic conditions e.g. deep incisions or cuts in the trunk of the plant (e.g. turpentine) or by hammering and scorching (e.g. balsam of Peru). Prepared Resins Oleo-resin: Solvent extraction with low boiling point solvents and distillation under vacuum In the case of oleo-resins, organic solvents with lower boiling points are normally employed e.g. ether and acetone for the extraction of drug and the volatile oil fraction can be removed conveniently through distillation under vacuum. Example: Colophony

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Extraction with alcohol and precipitation with water 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 a electric 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, ipomoea, capsicum, ginger and jalap Method for gum resins In the instance of gum-resins, the resin is extracted with 95% (v/v) ethanol while leaving the insoluble gum residue in the flask or soxhlet thimble. Heating By heating plant part e.g. in case of guaiacum

IMPORTANCE TO THE PLANTS:

IMPORTANCE TO THE PLANTS Resins primarily consist of secondary metabolites or compounds that apparently play no role in the primary physiology of a plant. While some scientists view resins only as waste products, their protective benefits to the plant are widely documented. The toxic resinous compounds may confound a wide range of herbivores, insects, and pathogens. The volatile phenolic compounds (in resins) may attract benefactors such as parasitoids or predators of the herbivores that attack the plant.

Composition of resin:

Composition of resin

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Characteristics Composition Example Resins Simple hydrocarbon compounds with some functional groups attached to them ( Cannabis , Rosin ) Resin alcohols (Resinols) Benzoresinol in benzoin and storesinol in Storax Resin acids Abietic acid (Colophony), Commiphoric acid (Myrrh), Alleuritc acid (Shellac ) Resin esters Benzyl benzoate and cinnamyl cinnamate ( Benzoin ) Ethyl cinnamate and cinnamyl cinnamate (Storax) Resenes Oxygenated inert compounds present in Myrrh Resin phenols (Resinotannols) Peru-resinotannol in Perubalsam, Tolu- resinotannol in Tolu balsam and siaresinotannol in benzoin

Combinations of resin:

Combinations of resin

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Class Characteristics Example Oleo-resin Naturally occurring mixtures of a volatile oil and a resin Turpentine Ginger Capsicum Oleo-gum resin A naturally occurring mix of volatile oil, Gums/Mucilagenous compound with a resin Myrrh Asafetida Glycoresins Resins in combination with sugar compounds via Glycosidal linkages Podophyllum Jalap Ipomoea Colocynth Balsams Resins in combination with benzoic or cinnamic acid Tolu balsam Peru balsam Storax Benzoin Gum resin s Resin in combinations with gum Ammoniacum

OLEO-GUM RESINS:

OLEO-GUM RESINS Mixtures of volatile oil, gum and resinous substances

Myrrh :

Myrrh

Myrrh :

Myrrh Botanical origin Commiphora molmol, Commiphora abyssinica , Commiphora myrrha Family Burseraceae Part used Stem Collection Secretions are obtained after spontaneous cracks or fissures in the bark. Sometimes incisions are also made in order to obtain secretions. These are light yellow in color and upon hardening in the air convert to reddish brown. Constituents 25-40% resin (alpha, beta and gamma commiphoric acid and alpha and beta heerabomyrrholic acid 57-61% gums, arabinose sugar 7-17% volatile oils (Eugenol, cuminic aldehyde, terpenes, esters and furano sesquiterpines Uses (ALAA) Antiseptic, astringent, local stimulant, aromatic, flavoring agent, expectorant, carminative

Asafoetida:

Asafoetida

Asafoetida :

Asafoetida Botanical origin Ferula foetida, Ferula asafoetida Family Umbelliferae Part used Root and rhizome Collection Resin is stored in large Schizogenous ducts and lysigenous cavities as milky liquid. Stem is removed and cut in slices. The exposed surface is covered by a dome shaped structure made of twigs and earth. It is golden yellow in color and packed in tine lined cases. Constituents Resin acid (ferulic acid, asaresinoferulate), Umbellic acid, Umbelliferone (lactone of umbellic acid) and u mbelliferyl esters Sulphur containing volatile oils, Gum R-2-butyl-1-propenyl disulphide (flavoring entity) Uses (CANALSE) Condiment, carminative, sedative (used in hysteria), expectorant, nervine, antiseptic, laxative, anthelmintic, hepatoprotective, anti-oxidant, anti-cancer agent

OLEO RESINS:

OLEO RESINS Mixtures of volatile oil and resinous substances

Terpentine:

Terpentine

Terpentine :

Terpentine Botanical origin Pinus longifolia Pinus roxburghii Pinus excelsa Family Pinaceae Part used Stem Collection Pinus oleoresin is a normal i.e. physiological product of pine. The amount of oleoresin produced is generally enhanced by injury or by treatment with 50% H2SO4. Constituents Volatile oil (Dicyclic monoterpenes; camphene and d and L alpha-pinene and Monocyclic monoterpenes; Limonene and methyl carbachol Resin (rosin) Uses Externally as counter-irritant, rubifaciant and mild antiseptic. Rectified oil internally is used as diuretic, urinary antiseptic, anti-rheumatic and expectorant

Ginger :

Ginger

Ginger :

Ginger Botanical origin Zingiber officinale Family Zingiberaceae Part used Fresh and dried rhizome (scrapped/un-scrapped) Collection Extraction with alcohol and precipitation with water Constituents 1-2% volatile oil (Monoterpenoids: β- phellandrene, camphene, cineole, Citral, Borneol and Sesquiterpene: zingiberene, β- sesquiphellandrene, ar-curcumene, Zingiberol and Shagaol) 5-8% resinous matter, small amounts of starch and m ucilage Zingerone imparts sweet odor and pungency is due to gingerol which can be destroyed by 5%NaOH Uses Rhizome is aromatic and pungent so is used as a condiment and flavoring agent. Treats flatulence and colic, stimulant, anti-emetic, lowers blood cholesterol, anti-hypertensive The oil is used in the food and perfume industries. Reduces pain associated with inflammation in arthritis

Capsicum :

Capsicum

Capsicum :

Capsicum Botanical origin Capsicum annum Capsicum minimum Family Solanaceae Part used Fresh and dried fruit Collection Extraction with alcohol and precipitation with water Constituents Capsaicin (oleo-gum resin), ascorbic acid, carotenoids, volatile alkaloid (capsico), capsacutin, capsorubin, capsanthin Uses Powerful stimulant Condiment Treatment of addiction (relaxes dilated blood vessels) Analgesic (pain management of neuralgia, migraine, lumbago, arthritis) Counter-irritant Used in scarlantia, hoarseness, yellow fever and dyspepsia

GLYCORESINS:

GLYCORESINS Glycosidal combinations of resins which upon hydrolysis yield sugar and complex resin acids

Jalap :

Jalap

Jalap :

Jalap Botanical origin Exogonium purga Family Convolvulaceae Part used Dried tuberous root Collection Constituents Convulvolin, jalapin, ipurganol, Volatile oils, gums, starch and sugar Uses Purgative and cathartic

Ipomoea :

Ipomoea

Ipomoea :

Ipomoea Botanical origin Ipomoea orizabensis Family Convolvulaceae Part used Dried fusiform roots Collection Constituents Methyl pentoside, jalapinolic acid, ipurganol, ipuranol, sitorterol and volatile oils Uses Purgative and cathartic

Colocynth :

Colocynth

Colocynth :

Colocynth Botanical origin Citrullus colocyntris Family Curcurbitaceae Part used Dried pulp of fruit Collection Fruit is melon green in colour, globular in shape and bitter in taste. It is collected and peeled to remove epicarp. Seeds are removed and pulp is dried in sun light. Constituents Colocynthin, colocynthinine, a complex resinous mixture of cucurbitacin E or α-Elaterin, β -Elaterin, cucurbitacin L, in the form of glycoside Uses Carminative Hydrogouge purgative Anthelmintic Narcotic Insecticidal

Podophyllum :

Podophyllum

Podophyllum :

Podophyllum Botanical origin Podophyllum peltatum & Podophyllum emodi Family Part used Dried rhizome Collection Constituents Podophyllum resin or podophylline, α- peltatin and β- peltatin and p odophyllotoxin Uses Purgative and cytotoxic (anti-cancer drug)

BALSAMS:

BALSAMS Resins in combination with benzoic or cinnamic acid

Benzoin :

Benzoin

Benzoin :

Benzoin Botanical origin Styrax benzoin, Styrax palallloneurus (Sumatra benzoin) Styrax tonkinesis (Siam-Thailand benzoin) Family Styracaceae Part used Stem Constituents Free balsamic acids (20% cinnamic acid and 10% benzoic acid) Triterpenoid components include Siaresinolic acid and Sumaresinolic acid Small amount of vanillin Siam variety contains coniferyl cinnamate, benzoate and alcohol Uses Expectorant Anti-septic Externally used in cosmetics, perfumery and toiletry Add flavor in food and drinks

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Collection Seeds of Styrax are sown in rice fields (rice shading the young trees during 1 st year). After harvesting of rice, the tress are allowed to grow until they are about 7 years old. Triangular wounds are made in a vertical row about 40cm apart, bark between wounds being scraped. 1 st secretion is very sticky and is rejected. After making further cuts, each about 4 cm above the preceding ones, harder secretion is obtained. Further incisions, after 3 months, the secretion becomes amorphous instead of crystalline. About 6 weeks of fresh tapping, the product is scrapped off and the outer layer (finest quality)being kept separate from the next layer (intermediate quality). About 2 weeks later the strip is scrapped again, giving a lower quality darker in color and containing fragments of bark. Grading is done by mixing 3 quality: best contains most almonds and worst contains a few almonds but abundant resin mixture. Blending is done by breaking up the drug, mixing different proportion of 3 qualities, softening in the sun, s tamping in to Tins & commercial drug arrives in plaited container with plastic wrapping

Tolu balsam:

Tolu balsam

Tolu balsam:

Tolu balsam Botanical origin Myroxylon balsamum Family Leguminosae Part used Trunk of the tree Collection On the trunk, v-shaped incisions are made and resin is allowed to flow. Buckets or receivers are attached to the trunk of tree for collection of resin (optimum yield per tree is 8-10kg) Constituents Tolu resinotannol Resin alcohols combined with cinnamic acid and benzoic acid Benzyl benzoate, small quantity of vanillin (imparts aroma) Free cinnamic acid and benzoic acid Eugenol, styrene, ferulic acid, terpenes Uses Expectorant Anti-septic (useful for preparing benzoin tincture) Flavoring agent for cough syrup

Peru balsam:

Peru balsam

Peru balsam:

Peru balsam Botanical origin Myroxylon pereiri Family Leguminosae Part used Trunk of the tree (young twigs) Collection Trunk is beaten using handle of axe or stone and scorched. A rag is placed under the bark to absorb resin. As secretions are pathological, these come out after about 5 days and resin flows for about 5-6 weeks. The rags are collected and put into strong rope bags which are twisted at the ends and pressed so that balsam falls into boiling water. Balsam sinks at the bottom of water, the water is decanted, balsam is collected, packed in tin containers. It is dark brown in color with vanilla like odor.

Conti…:

Conti… Constituents Benzyl cinnamate (cinnamein), cinnamyl cinnamate (styracin), benzyl benzoate Resin (28%) includes peruresinotannol esters with cinnamic acid, benzoic acid and alcohols (nerolidol, farnesol, benzyl alcohol and small quantities of vanillin and cinnamic acid Uses Mild irritant Anti-scabies Useful in skin ulcers and ring worms infections Antiseptic Parasiticidal Rubifaciant Astringent (used to treat diarrhea and catarrh)

Storax :

Storax

Storax :

Storax Botanical origin Liquidamber orientalis Family Part used Trunk of the tree Collection Constituents It consists of two resinous alkaloids α- storesin Β- storesin Also contain cinnamic acid and benzoic acid and their esters (ethyl cinnamate and cinnamyl cinnamate) Uses Anti-septic Expectorant Used for preparing benzoin tincture Also employed in cancer treatment

RESIN:

RESIN

ROSIN :

ROSIN

ROSIN:

ROSIN Botanical origin Pinus palustris, Pinus pinaster, Pinus halepnsis, Pinus carribacea Family Pinaceae Part used Trunk of tree Collection Terpentine oil after distillation left behind a solid residue called rosin. It is yellow or amber colored. Constituents It contains 90% resin acids (free) Resenes, esters of fatty acids, pi acids Alpha, beta and gamma abietic acid Spinic acid Uses Preparation of zinc oxide ointments, adhesive plastics Abietic acid pose antimicrobial and anti-ulcer activity

CANNABIS:

CANNABIS

CANNABIS:

CANNABIS Botanical origin Cannabis sativa (marijuana) Family Cannabinaceae Part used Dried flowering tops Constituents Cannabinoids: C11, C12 Cannabinols: Tetrahydrocannabinol (THC), Cannabidiol (CBD) Cannabidiol-carboxylic acid Cannabigerol Cannabichromene Uses Tonic Sedative and narcotic Strong analgesic Intoxicant Stomachic Antispasmodic Anxiolytic Anti-convulsant Anti-tussive

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Cannabis products and their preparation GANJA Seeds are sown in rows about 1.3m apart and male plants are discarded. Resinous tops of the unfertilized plants are cut about 5months after sowing and pressed in to cakes. Known as flat or Bombay ganja when 30 cm long pieces of the herb are bundled and pressed Round or Bengal ganja is prepared by rolling the wilted tops between the hands Ganja is legally produced under license in Bengal & southern India BHANG OR HASHISH Larger leaves and twigs of both male and female plants are s moked with or without tobacco. This product is unfit for medicinal use because of inherent deficiency of resin in its contents. It is taken in form of an electuary made by digestion with melted butter CHARAS It is obtained by rubbing the tops between the hands and beating them on a piece of cloth. Greenish brown soft mass adheres to the cloth and may be purified by pressing it through the clothes. The resin is scrapped off and m ixed with many smoking mixtures, with butter etc. for use

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Ganja Hashish Charas

REFERENCE BOOKS:

REFERENCE BOOKS

REFERENCE BOOKS:

REFERENCE BOOKS

REFERENCE TEXTS :

REFERENCE TEXTS Special thanks to Miss Priyanka Goswami, Lecturer, H. K. College of Pharmacy, Mumbai university Tschirch. A, and L. Stock: Die Harze, Borntraegr, Berlin, Vols. 1 & 2, 1933-36 .

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