RESINS FROM HERBAL ORIGIN (1).pdf

Parimal et al., IJPSR, 2011; Vol. 2(5): 1077-1085 ISSN: 0975-8232 IJPSR (2011), Vol. 2, Issue 5 (Review Article) Received on 05 January, 2011; received in revised form 26 February, 2011;...

Parimal et al., IJPSR, 2011; Vol. 2(5): 1077-1085 ISSN: 0975-8232 IJPSR (2011), Vol. 2, Issue 5 (Review Article) Received on 05 January, 2011; received in revised form 26 February, 2011; accepted 17 April, 2011 RESINS FROM HERBAL ORIGIN AND A FOCUS ON THEIR APPLICATIONS Kotkar Parimal*1, Anubha Khale 1 and Kadu Pramod 2 Department of Pharmacognosy, H. K. College of Pharmacy, Jogeshwari, Mumbai, Maharashtra, India Department of Biotechnology, Dr. Bhanuben Nanavati College of Pharmacy, Vileparle, Mumbai, Maharashtra, India ABSTRACT Keywords: The present article reveals an important role and wide applications Resins, played by the resins. Herbal system is considered as a Balsams, complimentary and alternative system of medicines plays a Oleo gum resins, significant role in India. Resins being the natural products are the Oleo-resins secondary metabolites which have therapeutic actions in humans and which can be refined to produce the drugs. Humans have been Correspondence to Author: using plant resins for thousands of years. Because wide use of resins they are collected by artificial injury to plants though they Mrs. Parimal Kotkar are secreted by plants in response to protect the plant. Resin is a Lecturer, H. K. College of Pharmacy, viscous compound hardens over time but softens on melting and Near MHADA Complex, does not react with water. This unique property makes the resins Jogeshwari(W), Mumbai, Maharashtra, India as a choice in preparing many excipients in the pharmaceutical dosage forms and even for preparing sustained release medicament formulation. The softer odoriferous oleo-resins and gum resins containing essential oils are more largely used for therapeutic purposes and incense. Thus resins play immense role in today’s pharmaceuticals. Available online on www.ijpsr.com 1077  International Journal of Pharmaceutical Sciences and Research ISSN: 0975-8232 INTRODUCTION: some scientists view resins only as waste products, their protective benefits to the plant are widely Resins and Resin Combination: Resins are amorphous documented. Many resinous products are not formed products of complex nature. These are amorphous by the plant itself unless and until purposeful and mixtures of essential oils, oxygenated products of methodical injuries in the shape of incisions are made terpene and carboxylic acids found as exudations from on them and the secretions or plant exudates are the trunk of various trees. They are transparent or tapped carefully, such as: Balsam of Tolu and Benzoin translucent solids, semi-solids or liquid substances 2. containing large number of carbon atoms. Most of the resins are heavier than water. They are insoluble in The toxic resinous compounds may confine a wide water, but soluble in alcohol, volatile oils, fixed oils, range of herbivores, insects, and pathogens; while the chloral hydrate and non-polar organic solvents like volatile phenolic compounds may attract benefactors benzene or ether. They are hard, electrically non- such as parasitoids or predators of the herbivores that conductive and combustible masses. When heated, attack the plant 3. they soften and ultimately melt. They are usually formed in schizogenous or schizolysigenous cavities or Distribution of Resins in Plants: The resins and ducts as end products of metabolism. resinous substances are more or less extensively distributed throughout the entire plant kingdom, Chemically, they contain organic acids, alcohols, esters specifically the Spermatophyta i.e., the seed plants. and neutral resins. Depending upon the type of the Notably, their presence is almost rare and practically constituents of the resin, they are further classified as: negligible in the Pteridophyta i.e., the ferns and their acid resin, ester resin and resin alcohols. Resins and allies. However, the resins have not been reported in oils in homogenous mixtures are called as oleoresins. the Thallophyta i.e. the sea-weeds, fungi etc. Oleo-gum resins are the homogenous mixtures of Therefore, all these findings and observations lead one volatile oil, gum and resin. If the resin contains benzoic to the fact the resins are the overall and net result of acid and/ or cinnamic acid, it is called as a balsam 1. metabolism in the higher plants, since majority of them belong to the phylum Angiosperm i.e., seed- Resin is a hydrocarbon secretion of many plants, enclosed flowering plants, and Gymnosperm i.e., particularly coniferous trees. It is valued for its naked-seed non-flowering plants 4. chemical constituents and uses, such as varnishes and adhesives, as an important source of raw materials for Occurrence of Resins in plants: In the plants resins organic synthesis, or for incense and perfume. usually occur in different secretory zones or structures. Fossilized resins are the source of amber. Resins are A few typical examples of such plant sources along also a material in nail polish. Resins have a very long with their specific secretary structures are given history and are mentioned by both ancient Greek below: Theophrastus and ancient Roman Pliny the Elder, especially as the forms known as frankincense and i. Resin Cells: Ginger myrrh. They were highly prized substances used for ii. Schizogenous Ducts or Schizolysogenous Ducts many purposes, especially perfumery and as incense in or Cavities: Pine Wood religious rites. There is no consensus on why plants iii. Glandular Hairs: Cannabis secrete resins. However, resins consist primarily of It has been observed evidently that resins are secondary metabolites or compounds that apparently invariably produced in ducts as well as cavities; play no role in the primary physiology of a plant. While sometimes they do not occur in the so called Available online on www.ijpsr.com 1078  International Journal of Pharmaceutical Sciences and Research ISSN: 0975-8232 specialized-secretory structures, but tend to get being the most notable instance of this class; African impregnated in all elements of a tissue, for example: copal and the kauri gum of New Zealand are also Guaiacum Resin- is obtained from the heartwood of procured in a semi-fossil condition 4. Guaiacum officinale Linn. and G. sanctum Linn. i.e., it is found in the vessels, fibers, medullary ray cells and Physical properties: wood parenchyma. In this particular instance, the 1. Resins are hard, transparent or translucent brittle resins occur as tyloses, achieved by chopping off the materials. conduction in these areas so as to enhance the 2. They are invariably heavier than water having the effective usage of root pressure and the capillaries in specific gravity ranging from 0.9-1.25. forcing both the nutritive contents and forcing water 3. Resins are more or less amorphous materials but to reach the top end of these tall trees. rarely crystallizable in nature. Chemistry: The resin produced by most plants is a 4. On being heated at a relatively low temperature viscous liquid, composed mainly of volatile fluid resins first get softened and ultimately melt terpenes, with lesser components of dissolved non- down thereby forming either an adhesive or a volatile solids which make resin thick and sticky. The sticky massive fluid, without undergoing any sort most common terpenes in resin are the bicyclic of decomposition or volatilization. terpenes alpha-pinene, beta-pinene, delta-3 carene 5. On being heated in the air i.e., in the presence of and sabinene, the monocyclic terpenes limonene and oxygen, resins usually burn readily with a smoky terpinolene, and smaller amounts of the tricyclic flame by virtue of the presence of a large number sesquiterpenes, longifolene, caryophyllene and delta- of C-atoms in their structure. cadinene. Some resins also contain a high proportion 6. On being heated in a closed container i.e., in the of resin acids. The individual components of resin can absence of oxygen, they undergo decomposition be separated by fractional distillation. and very often give rise to empyreumatic products i.e., products chiefly comprising of A few plants produce resins with different hydrocarbons. compositions, most notably Jeffrey Pine and Gray Pine, 7. Resins are bad conductors of electricity, but the volatile components of which are largely pure n- when rubbed usually become negatively charged, heptane with little or no terpenes. The exceptional 8. They are practically insoluble in water, but purity of the n-heptane distilled from Jeffrey Pine frequently soluble in ethanol, volatile oils, fixed resin, unmixed with other isomers of heptane, led to oils, chloral hydrate and non- polar organic its being used as the defining zero point on the octane solvents e.g., benzene, n-hexane and petroleum rating scale of petrol quality. Because heptane is highly ether 5. flammable, distillation of resins containing it is very dangerous. Some resins when soft are known as 'oleo- Chemical properties: resins', and when containing benzoic acid or cinnamic 1. Resins, in general, are enriched with carbon, acid they are called balsams. Other resinous products deprived of nitrogen and contain little oxygen in their natural condition are a mix with gum or in their respective molecules. mucilaginous substances and known as gum resins. 2. Majority of them undergo slow atmospheric oxidation whereby there color gets darkened Many compound resins have distinct and characteristic with impaired solubility. odors, from their admixture with essential oils. Certain resins are obtained in a fossilized condition, amber Available online on www.ijpsr.com 1079  International Journal of Pharmaceutical Sciences and Research ISSN: 0975-8232 3. Resins are found to be a mixture of numerous Derivatives: Solidified resin from which the volatile compounds rather than a single pure chemical terpene components have been removed by entity. distillation is known as rosin. Typical resin is a 4. Their chemical properties are exclusively based transparent or translucent mass, with a vitreous upon the functional groups present in these fracture and a faintly yellow or brown color, non- substances. odorous or having only a slight turpentine odor and 5. Consequently, the resins are broadly divided taste. It is insoluble in water, mostly soluble in alcohol, into resin alcohols, resin acids, resin esters, essential oils, ether and hot fatty oils, and softens and glycosidal resins and resene (i.e., inert neutral melts under the influence of heat, is not capable of compounds). sublimation, and burns with a bright but smoky flame. 6. Resins are regarded as complex mixtures of a variety of substances, such as: resinotannols, This comprises a complex mixture of different resin acids, resin esters, resin alcohols and substances including organic acids named the resin resene. acids. These are closely related to the terpenes, and 7. Resins are nothing but oxidative products of derive from them through partial oxidation. Resin acids terpenes. can be dissolved in alkalis to form resin soaps, from 8. They may also be regarded as the end products which the purified resin acids are regenerated by of destructive metabolism. treatment with acids. Examples of resin acids are 9. The acidic resins when treated with alkaline abietic acid (sylvic acid), C20H30O2, plicatic acid solutions they yield soaps (or resin-soaps) 6. contained in cedar, and pimaric acid, C20H35O2, a constituent of galipot resin. Abietic acid can also be Solubility: extracted from rosin by means of hot alcohol; it crystallizes in leaflets, and on oxidation yields 1. Majority of resins are water- insoluble and trimellitic acid, isophthalic acid and terebic acid. hence they have practically little taste. Pimaric acid closely resembles abietic acid into which it 2. They are usually insoluble in petroleum ether (a passes when distilled in a vacuum; it has been non-polar solvent) but with a few exceptions. supposed to consist of three isomers 8. Such as: Colophony (freshly powdered) and mastic. Classification of Resins: The resins are broadly 3. Resins mostly got completely dissolved in a classified under three major categories, namely: number of polar organic solvents, for instance: ethanol, ether and chloroform, there by Taxonomical Classification: The resins are grouped forming their respective solutions which on according to their botanical origin exclusively, such as: evaporation, leaves behind a thin-varnish-like film deposit.  Coniferous Resins: e.g., Colophony, Sandarac; 4. They are also freely soluble in many other  Berderidaceae Resins: e.g., Podopyllum and organic solvents, namely: acetone, carbon  Zygophyllaceae Resins: e.g., Guaiacum disulphide, as well as in fixed oils and volatile In this particular instance, it has been observed that oils. the resins that usually occur in plants of the same 5. Resins dissolve in chloral hydrate solution, natural order, may exhibit more or less related normally employed for clarification of certain characteristics features. sections of plant organs 7. Available online on www.ijpsr.com 1080  International Journal of Pharmaceutical Sciences and Research ISSN: 0975-8232 Chemical Classification: The resins may also be B. Isolation of Resins: Pharmaceutical resins are classified as per the presence of the predominating obtained from the plants and animals by one of the chemical constituents for instance: following methods 2.  Acid Resins: e.g., Colophony (Abietic acid); 1. By extraction with alcohol and precipitation Sandarac (Sandracolic acid); Shellac (Alleuritic with water, e.g. Jalap, Podophyllum, Ipomoea, acid); Myrrh (Commiphoric acid); etc.  Ester resins: e.g., Benzoin (Benzyl benzoate), 2. By distillation for separation of oil, e.g. Copaiba, Storax (Cinnamyl cinnamate); Colophony, etc.  Resin Alcohols: e.g., Balsam of Peru 3. By heating the plant part, e.g. Guaiacum. (Peruresinotannol), Guaiacum resins 4. As plant exudates by incisions, e.g. Myrrh, (Guaicresinol); Gurjun balsam (Gurjuresinol); Asafoetida, Balsams, etc.  Resene Resins: e.g., Dragon’s Blood 5. By collecting fossil resins, e.g. copal, kauri, etc. (Dracoresene); Gutta-percha (Fluavil); 6. By processing the encrustations i.e. shellac.  Glycoresins: e.g., Jalap resin from jalap i.e, Ipomea purga Haynel; (Family: Conrulvulaceae) Resins: The various resins are as follows: Podophylloresin from the dried roots and 1. Colophony: Colophony is the residue left after rhizomesof Podophyllum hexandrum (P.emodi) the distillation of the oil of turpentine from the Royle. (Family Berberidae) crude-oleo-resin obtained from various species of A. Constituents of resin: Invariably, to maintain the Pinus belonging to family Pinaceae. Colophony simplicity, resins may also be classified according to contains 90% resin acids known as abietic acid. the major constituents present either in the resin The remaining 10% as resene is an inert or resin combination e.g., Resins; Oleo-resins; substance and is a ester of fatty acids. It also Oleo-gum resins; Balsams. contains a mixture of dihydroabietic acid (C20H30O2) and dehydroabietic acid (C20H28O2). On After having been exposed to the various aspects of being heated at 300oC, abietic acid undergoes resins with regard to their physical and chemical further molecular rearrangement to produce properties, occurrence and distribution, preparation, neo-abietic acid. chemical composition and classification, it would be worthwhile to gain some in-depth knowledge about Uses: certain typical examples belonging to resins; Oleo- 1. Colophony is a stimulant and diuretic. resins; Oleo-gum-resins; Balsams; and Glycoresins 2. 2. Colophony is used in pharmacy for the preparation of zinc oxide plasters, ointments Uses: The hard transparent resins, such as the copals, and other adhesive plasters. dammars, mastic and sandarac, are principally used for 3. It is widely used in the manufacture of printing varnishes and cement, while the softer odoriferous inks, rubber, dark varnishes, sealing wax, oleo-resins (frankincense, elemi, turpentine, copaiba) linoleum and thermoplastic floor tiles. and gum resins containing essential oils (ammoniacum, 4. It also finds application as varnish and paint asafoetida, gamboge, myrrh, and scammony) are more dries, cements, soaps, wood polishes, paper, largely used for therapeutic purposes and incense. plastics, fireworks, tree wax, sizes, rosin oil. 5. It is used for waterproofing cardboard, walls etc 6. Available online on www.ijpsr.com 1081  International Journal of Pharmaceutical Sciences and Research ISSN: 0975-8232 2. Lac: Stick lac contains 70-80% of resin, sugars, 3. It is invariably prescribed with other proteins, coloring matter (1-2%), wax (4-6%), purgatives, henbane or belladonna to extraneous matter (8-10%), and volatile oil in prevent gripping in infants. traces. Lac resin consists of hydroxy fatty acid derivatives. Aleuritic acid is the main constituent 4. Tar: Tar contains many chemical constituents in 35% of resin, while shelloic acid and its isomer various proportions depending upon the along with kerrolic acid and butolic contain particular species of Pinus and its geographic laccaic acid which is water soluble. location, such as: hydrocarbons, resin acid, resinous matter, and includes phenols, phenolic Uses: ethers, cresols, catechol, methyl cresols, guaiacol, 1. It is extensively used for coating tablets and benzene, toluene, xylene and styrene. confections. 2. It has also been used for preparing sustained Uses: release medicament formulation. 1. It serves as an expectorant when used in 3. It is used chiefly in lacquers and varnishes. the form of syrup. 4. It is also employed in the manufacture of 2. Pine tar is frequently employed as buttons, sealing wax, cements, inks, grinding antipruritic and antibacterial. wheels, photograph records, paper. 3. It is used largely in ointments externally for 5. It also finds its use in electrical machines and the treatment of chronic skin diseases and for stiffening hats. It has also used for eczema 9. finishing leather 9. Oleoresins: A few important oleoresins are as follows, 3. Podophyllum: The composition of resin is made of lignans which contain at least 40% of 1. Capsaicin: podophyllotoxin. American podophyllum resin Chemical Constituents: The capsicum contains 8-12% contains only 10% of podophyllotoxin. of an oleoresin capsaicin and a red coloring principle Podophyllotoxin is teranhydronapthalene known as capsanthin. The pungency of capsaicin is not derivative with OH and lactone group in trans affected by dilute alkali, but is destroyed almost position which is essential for anti-mitotic completely by subjecting it to oxidation with either activity. In cis position, it possesses only KMnO4 or K2Cr2O7. purgative activity. Apart from podophyllotoxin, picropodophyllin, quercetin, astragalin and Uses: resinous substances are also found in 1. It is used as a tool in neurobiological podophyllin. research. 2. Pretreatment with capsaicin induces long- Uses: lasting desensitization of airway mucosa to 1. Podophyllotoxin possesses anti-tumor various mechanical and chemical irritants 8. (antineoplastic) properties and may be used in the treatment of cancer. 2. Male Fern: The main active constituents of male 2. It is used as a drastic but slow-acting fern are derivatives of phloroglucinol and butyric purgative. acid. It has been observed that two or more molecules of simple monocyclic derivatives, such as: aspidinol, filicinic acid and acylfilicinic acid Available online on www.ijpsr.com 1082  International Journal of Pharmaceutical Sciences and Research ISSN: 0975-8232 may get condensed to give rise to bicyclic Oleo-Gum-Resins: The oleo-gum-resins are the derivatives. naturally occurring mixture of resin, gum, volatile oil, and mostly small quantities of other substances. There Uses: are some potent oleo-gum-resins which exhibit 1. Male fern oleoresin is an antihelmentic, remarkable medicinal values. A few drugs containing specifically a taeniafuge. oleo-gum-resins are as follows. 2. It is also used as its extract for the expulsion of tapeworms 10. 1. Asafoetida: Asafoetida contains volatile oil (8- 16oC), gum (25%) and resin (40-60%).The volatile 3. Ginger: Ginger contains volatile oil (1-3%), which oil essentially consists of some organic sulphides comprises of zingiberene, α-curcumene, β- solely responsible for attributing the sesquiphellandrene and β-bisabolene. characteristic garlic-like odor. The resin consists Zingiberene has two chiral centers. The acyclic of notannol, asaresinotannol i,e., the resin chiral center has been steriochemically related to alcohols, which are present partially in the free that in (+)-citronellal, and the cyclic chiral center state and partially in the combined form with to that in (-)-zingiberene has the absolute ferulic acid. It also contains umbellic acid and configuration. The oleoresin contains the umbelliferone; the latter is found combined with pungent gingerols and shogaols. ferulic acid, but it gets generated on being treated with dilute HCl. Uses: 1. It is used as flavoring agent, carminative, Uses: aromatic and stimulant to gastrointestinal 1. It is abundantly used in India and Iran as a tract. common condiment and flavoring agent in 2. Ginger finds its wide applications in soft food products. drinks, beverages, ginger beer and wine. 2. It is also an important ingredient in 3. It is extensively used for culinary purposes Worcestershire Sauce. in ginger-bread, biscuits, puddings, cakes, 3. It is used as a repellant [2% (w/v) soups and pickles 10. suspension] against dogs, cats, deer, rabbits etc. 4. Turpentine: The gum- turpentine when subjected 4. It is used seldomly as an antispasmodic, to steam-distillation yields15-30% of a volatile oil carminative, expedorant and laxative. known in the trade as “turpentine oil”. It contains 5. It is still employed in veterinary externally mainly the terpenes, such as: dextra-and laevo-α- to prevent bandage chewing by dogs. pinene, β-pinene and camphene. 6. It is also used as a powerful nerve stimulant especially in nervous disorders related to Uses: hysteria 11. 1. It is employed externally as a counterirritant and rubefacient. 2. Turmeric: It contains volatile oil (5-6%), resin and 2. It is used as a constituent of stimulating substantial quantity of zinzgiberaceous starch ointments. grains. The marked and pronounced yellow color 3. It is employed industrially as an insecticide. in turmeric is due to the presence of 4. It is used as a solvent for waxes. curcuminoids which essentially contains 5. It is utilized extensively in the production of curcumin. The volatile oil contains a host of synthetic camphor. Available online on www.ijpsr.com 1083  International Journal of Pharmaceutical Sciences and Research ISSN: 0975-8232 chemical substances, such as: d-α-phellandene, 2. It is frequently employed as an antiseptic d-sabinene, cineol, borneol, zingiberene, and and stimulant. sesquiterpenes. Turmeric also contains some 3. Myrrh acts as an astringent to the mucous other chemical constituents, namely: p,p- membrane and hence it finds its dihydroxy dicinnamoylmethane; p-α-dimethyl application in oral hygiene formulations, benzyl alcohol; p-hydroxy- such as: gargles, mouth-washes. cinnmoylferuloylmethane; 1-methyl-4-acetyl-1- 4. It is also used as carminative 13. cyclohexene; and caprylic acid. 4. Ammoniacum: Ammoniacum the oleo-gum-resin Uses: consists of volatile oil (0.1-1.0%), resin (65-70%), 1. It is exclusively used across the globe as a gum (20%), moisture (2-12%), insoluble residue condiment as curry powder. (3.5%) and ash (1%). Ammoresinol, a phenolic 2. It is employed as coloring agent for substance is the main constituent of the resin, ointments. which is a colorless crystal, mp 110oC. It also 3. It is used medicinally as a tonic, as a blood contains traces of salicylic acid. purifier, as an anthelmintic and finally as an aid to digestion. Uses: 4. It is used medicinally in the form of a facial 1. It is an important ingredient of porcelain cream to improve complexion and get rid of cements. pimples. 2. It is a stimulant, and secreted by the 5. A small quantity of turmeric when boiled bronchial mucous surface, thereby with milk and sugar, it helps to cure disinfecting the secretions. common cold and cough symptoms 12. 3. It is used in plaster-of-paris (POP) plasters as a stimulant to the skin. 3. Myrrh: Myrrh contains volatile oil (7-17 %), resin 4. It is also used as a disinfectant expectorant (20-25 %), gum (57-61 %), and bitter principle (3- in chronic bronchitis amalgamated with 4 %). The volatile consists of eugenol, m-cresol excessive discharge (Ashutosh Kar, 2007). and cuminaldehyde. The resin is found to consist of a mixture of α-, β-, and γ- commiphoric acids Thus, variety in compositions of resins makes them (resin acids). It also containstwo phenolic resins pharmaceutically useful and its contribution can not be α- and β- herrabomyrrholic acids which are ether ignored. insoluble. The oleo-gum-resin yields alchol- soluble extract not less than 30%. It also contains REFERENCES: phenolic compound such as: pyrocatechin and 1. Jean Langenheim, 2004, "Plant Resins: Chemistry, evolution, protocatechuic acid. The crude alcohol-insoluble ecology, and ethnobotany", Ann Bot , 93 (6): 784-785 2. Ashutosh Kar, 2007, “Pharmacognosy and fraction i.e., gum, comprises of protein (18%) and Pharmacoboitechnology”, Second Edition, New Age carbohydrate (64%) made up of arabinose, International Publishers, 306-338 galactose and glucuronic acid. However, the gum 3. C K Kokate, A P Purohit, S B Gokhale , 2007,“Pharmacognosy”, Thirty ninth Edition, Nirali Prakashan, 405-442 is found to be associated with an oxidase 4. T E Wallis ,2005 “Textbook of Pharmacognosy”, Fifth Edition, enzyme. 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