Volatile Oils Lecture Notes PDF

Volatile oils 1. Hydrocarbon volatile oils  Lemon peel:  Synonym: limon  Origin: yellow outer rind of the fresh ripe fruit of (Citrus limon F: Rutaceace).  Constituents:  Terpene (limonene), aldehyde volatile oil, coumarins, flavonoids (rutin, hesperidin). New research indicated that...

Volatile oils 1. Hydrocarbon volatile oils  Lemon peel:  Synonym: limon  Origin: yellow outer rind of the fresh ripe fruit of (Citrus limon F: Rutaceace).  Constituents:  Terpene (limonene), aldehyde volatile oil, coumarins, flavonoids (rutin, hesperidin). New research indicated that limonene showed significant antioxidant activity and cytotoxic activity against mouse leukemia by specific mechanism including: necrotic cell death and apoptosis to lower extent in cancer cells. Limonene : studies have demonstrated the anti-tumorigenic effects of limonene against pancreatic cancer and breast cancer. Limonene showed antioxidant, and radical scavenging activities in several model systems and cytotoxic against hepatocarcinoma, colon cancer, breast cancer, also have very strong activity as anti-inflammatory, antiproliferative, anti- invasive, and potential anti-angiogenic activities. Humulene :  Is a naturally occurring monocyclic sesquiterpene obtained from Humulus lupulus F: Cannabinaceae Humulene has been found to produce anti- inflammatory effects, and has potential to be a tool in the management of inflammatory disease. It produces similar effects to dexamethasone, and was found to decrease the edema formation caused by histamine injections. Humulene produced inhibitory effects on tumor necrosis factor- (TNF- ) and interleukin-1β. Kaurene: Is diterpene found in Agathis plant showed powerful anti-tumor activity by inhibition of cell proliferation. Oil of Turpentine:  Synonym: spirit of turpentine, rectified oil of turpentine.  Origin: rectified volatile oil distilled from the oleoresin of Pinus palustris F: pinaceae.  Constituents: and β-pinene, camphene  Uses: externally-counterirritant, rubifacient, fragrance, flavoring.  Rectified turpentine oil: Obtained from Humulus lupulus F: Cannabinaceae.  Constituents: β- Myrcene  Uses: local irritant, expectorant, diuretic and urinary antiseptic. 2. Alcoholic volatile oils Alcohols found in volatile oil may be classified into four groups: 1. Acyclic Alcohols: Methyl, ethyl, isobutyl, isoamyl, hexyl and higher aliphatic alcohols are present in volatile oils but they are washed away during the process of steam distillation as they are soluble in water. 2. Monocyclic Alcohols: Among the monocyclic alcohols, the important ones are menthol. 3. Bicyclic alcohols: Borneol is bicyclic terpene. 4. sesquiterpene alcohols: This group includes zingiberol, zingiberol found in the oil of Zingiber officinale. Zingiberol is used as an anti-emetic, carminative drug. It is effective in the control of vomiting and nausea in hyperemesis as well as postoperative nausea and vomiting. The cardiovascular activity shown by zingiberol is mainly due to the inhibition of prostaglandin synthetase. Zingiberol also has antiplatelet aggregation property which is due to the inhibition of thromboxane synthesis, also lowers cholesterol levels by inhibition of cholesterol biosynthesis under the assumption of inhibiting HMG-COA reductase, also posses antitussive, anti-pyretic, and analgesic effects, and has been reported to have fungicidal, antibacterial and anthelmintic properties. Peppermint oil: Origin: dried leaves of Mentha piperita (F:Labiatae) Constituents: menthol, pinene, limonene, resin and tannin Uses: pharmaceutical aid (flavor), carminative, stimulant, counterirritant, antibacterial, antiviral, antispasmodic, and anti-flatulence. Recently Menthol was cytotoxic for murine leukemia cells in a concentration dependent manner, menthol induced cytotoxicity by inhibiting the expression of topoisomerase I,II. Menthol inhibit the proliferation and motility of prostate cancer cells and human bladder cancer cell, also it reduced the invasion potential of oral squamous carcinoma cell lines. Adverse effects: Gallstones, obstructed bile ducts, gall bladder inflammation, sever liver damage. Menthol Used as topical antipruritic in burns and sunburn preparations and in joint pain, counterirritant, antiseptic, stimulant. Internally, depressant effect to the heart. Key step in the biosynthesis of menthol appears to be the dehydration of Terpineol to Terpinolene. NADPH2 is an essential Co-factor in these reduction reaction. Menthol may be levo(-) Menthol (from natural or synthetic) or racemic (+) Menthol produced synthetically. 3. Ketone volatile oils: Either: 1.Monocyclic Terpene Ketone like: Menthone, Carvone, Pulegone. 2. Di or Bicyclic ketone like: Camphor. 3. Non Terpenic Ketone The most important drugs of this category are: Camphor, Spearmint, Caraway. Camphor Obtained from Cinnamomum camphora F:(Lauraceae). Natural camphor occurs as crystalline product in clefts in the wood of plant. Biosynthesis: in biosynthesis, camphor is produced from geranyl pyrophosphate, via cyclisation of linaloyl pyrophosphate to bornyl pyrophosphate, followed by hydrolysis to borneol and oxidation to camphor.  Camphor is readily absorbed through the skin and produces a feeling of cooling similar to that of menthol, and acts as slight local anesthetic and antimicrobial substance, anti- itch. Camphor is used topically to increase local blood flow and as a “counterirritant”, which reduces pain and swelling by causing irritation. It is important not to apply camphor to broken skin, because it can enter the body quickly and reach concentrations that are high enough to cause poisoning. Some people use camphor topically to treat respiratory tract diseases and to treat heart disease symptoms. Camphor is also used topically as an eardrop, and for treating minor burns. Camphor seems to stimulate nerve endings that relieve symptoms such as pain and itching when applied to the skin. Camphor is also active against fungi that cause infections in the toenails. Spearmint Origin: dried leaves and flowering tops of Mentha spicata (Labiatae). Constituents: (-) carvone, (-) limonene, phellandrene Use: carminative, stimulant, flovoring agent. Dill Origin: dried ripe fruit of Anethum graveolens (Apiaceae) Constituents: carvone, limonene. Use: carminative, flovor, used in infant’s gripe water Antispasmodic, bacteriostatic, calming effect, regulate menstrual cycle. 4. Aldehyde volatile oils  Acyclic : citral  Cyclic: aromatic (cinnamon)  Aldehyde v. oils are calming to the nervous system. They are best known to relieve stress and promote relaxation. cinnamon  Driedbark of cinnamomum lureirii (F:Lauraceae)  Cinnamon oil contain cinnamaldehyde as a major compound Cinnamaldehyde 5. Phenolic volatile oils Thyme Origin: dried leaves and flowering tops of Thymus vulgaris (Labiatae) Constituents: thymol, carvacrol Thymol oil is a powerful antibacterial and antiseptic agent, thymol was effective against a wide range of bacteria including E. coli, Pseudomonus aerogenosa, Staphyllococcus aureus and Bacillus. thymol is found as an active ingredient in a variety of mouth washes and toothpastes, also it has strong anti-fungal activity against wide range of fungi. Thymol helps to reduce bloating spasming of the intestinal tract and improves appetite. Due to the significant anti-bacterial and antifungal properties, thymol helps to treat candida, gastroenteritis and digestive tract. Clove oil Origin: the dried flower buds of Eugenia caryophyllus F: Myrtaceae Constituents: volatile oil contains eugenol, gallotannic acid, oleanolic acid, vanillin, chromone, eugenin Use: flavoring agent, stimulant, aromatic and antiseptic, dental analgesic, antibacterial. 6. Phenolic ether volatile oils: Anise Origin: dried ripe fruits of Pimpinella anisum F: Apiaceae. Constituents: volatile oil contains anethole, methyl chavicol, pinene, linalool and anisaldehyde. Use: flavor, aromatic stimulant, carminative. Anethole is colorless or pale yellow liquid at or above 23°C, at 21°C it solidifies to a crystalline mass that melt at (22-23)°C. it has a sweet taste and aromatic odor of anise, because it is affected by light, anethol should be preserved in tight, light-resistant containers. Anethole Biosynthesis of anethole Nutmeg Origin: dried kernels of Myristica fragrans F: Myristicaceae. Constituents: volatile oil contains myristicin, safrole, eugenol. Use: flavoring agent, carminative, condiment, Indian medicine, used in the treatment of infantile diarrhea. Nutmeg is known for it’s psychoactive and hallucinogenic properties, however the relatively large amount (up to 15gm) that be ingested to cause the desired intoxication also produces flushing of the skin, tachycardia, absence of salivation and other adverse effect. The active principle responsible for the effect of Nutmeg on the C.N.S. have not been identified yet, but elemicin and myristicin are believed to be involved. 7. Oxide volatile oils Eucalyptus Origin: dried leaves of Eucalyptus globulus F: Myrtaceae. Constituents: volatile oil (1,4-Cineole and 1,8- Cineole), resins and tannic acid. Eucalyptus has a fresh camphor like smell and spicy, cooling taste. It is insoluble in water, but miscible with ether, ethanol and chloroform. The boiling point is 176°C. Eucalyptol forms crystalline adduct with hydrohalic acids, and phosphoric acid. Formation of these adducts are useful for purification. Because of it’s pleasant spicy aroma and taste, eucalyptol is used in flavorings, fragrance, and cosmetics. Cineole-based eucalyptus oil is used as a flavoring at low levels (0.002%) in various products. Eucalyptol is an ingredient in many brands of mouth wash and cough suppressant. Use: alleviate symptoms of nasopharyngeal infections, treat coughs and decongestant. Internally: expectorant Externally: treat sore muscles and rheumatism. In higher than normal doses, eucalyptol is hazardous via ingestion, skin contact, or inhalation. It can have acute health effects on behavior, respiratory tract and nervous system. 8. Ester volatile oils  Methylsalicylate  Wintergreen oil  From Gaultheria Wintergreen oil is used topically (diluted) or aroma therapeutically as a folk remedy for muscle and joint discomfort, arthritis, edema, poor circulation, headache rheumatism, inflammation, eczema, psoriasis, gout, ulcer. The liquid salicylate dissolves into tissue and also into capillaries, so overuse is as risky as overuse of aspirin. Wintergreen also is used in some perfumery applications and as a flavoring agent for toothpaste, chewing gum, soft drink.