Lecture № 11

1. Lecture №11 Chemical analysis of MPM containing essential oils. Herbs and MPM that contain monoterpenes and sesquiterpenes

2. Volatile oils (VO) are miscellaneous volatile organic compounds which are produced in plants and cause their specific odour • They differ entirely in both chemical and physical properties from fixed oils. VO can be distilled from their natural sources; they do not consist of glyceryl esters of fatty acids. Hence, they do not leave a permanent grease spot on paper. VO do not become rancid as do the fixed oils, but instead, on exposure to light and air, they oxidize and resinify.

3. VO can be divided into 3 main groups: • monoterpenoids (acyclic, monocyclic and bicyclic); • sesquiterpenoids (acyclic, monocyclic, bicyclic, tricyclic); • aromatic compounds (derivatives of n-cimen, benzol and phenilpropan).

4. Terpene hydrocarbons • Monoterpene hydrocarbons • Sesquiterpenes • Oxygenated compounds • Phenols • Alcohols • Monoterpene alcohols • Sesquiterpene alcohols • Aldehydes • Ketones • Esters • Lactones • Coumarins • Ethers • Oxides

5. Моnoterpenoids (C10H16) • Аcyclic 2,6-Dimethyloctan Linalool Citronellal

6. Monocyclic monoterpenoids N-menthan 1 methyl,4-I sopropilhexan Menthol Carvone 1,4-Cineol 1,8-Cineol

7. Bicyclicmonoterpenes (types of carane, pinane, camphane, thujane) Carane type Carane Carane Carane Pinane type Pinane α-pinane β-pinane Camphane type Camphane Camphene Borneol (-) Camphor Thujane type Thujane Sabinen Thujol Thujone

8. Bornil isovalerianate

9. Sesquiterpenoids (C15H24) • Аcyclic • Monocyclic Farnesane Farnesene Farnesol Bisabolane Bisabolone Bisabolol

10. Bicyclic 1. Alkilnaphthalene type 2. Alkilazulene type Cadinane Cadinene Cadinol Selinane (evdesmane) α-Selinene β-Selinene Guaiane type Chamazulene type Guaiane S-Guaiazylene Se-Guaiazylene Chamazulane Chamazulene

11. Azulane 3. Bicyclic sesquiterpenoids of other structure Akorane

12. Aromadendrane Tricyclicsesquiterpenoids Sesquiterpenelactone Eudesmanolide type Guaianolide type Alantolactone Santonine Mathrycyne

13. Aromatic compounds p-Cymene type p-Cymene Thymol Carvacrol Phenylpropan type Anetole Evgenole Azarone Benzene type Anise aldehyde Vanillin Phenylehylic alcohol

14. Occurrence Essential oils are of wide occurrence in Nature. More than 2500 of plants can accumulate them. Tropical plants are rich in VO. Usually they occur in such families as Lamiaceae, Apiaceae, Asteraceae and Rosaceae. The content may rich up to 20% (Citrus fruits). Ether oils are produced by special exo- and endogenic organs.

15. Essential oil cells (Acoruc calamus) Glands (fam. Asteraceae) Glands (fam. Lamiaceae) Essential oil tubes (ducts) (Foeniculum vulgare) Essential oil reservoir (Eucalyptus globulus)

16. Methods of obtaining of volatile oils • Distillation in water and steam • Scarification and expression (pressing) • Extraction with solvents (Extraction with volatile solvents and the enfleurage) • Enzymatic hydrolysis

17. Clavenger apparatus • (according to Sovet pharmacopeia XI) • A round bottom pyrex distillation • A receiver (trap) • A cork • A condenser (according to WHO, EuPh\ Xylen

20. MP and MPM containing monoterpenoids

21. Menthae piperitae folia Menthapiperita- Peppermint, Lamb mint, American mint, Brandy mintLamiaceae • Constituents. Leaves contain up to 3.5% of ether oil and menthol is the main part- up to 80%; resin, tannins, acetic acid, etc. • Uses. Infusion stimulates the secretion of digestive glands, has sedative, spasmolitic, cholagogue and light pain-killing action. Volatile oil is part of Inhalipt, Corvaldin, Mint tablets, Tooth drops, Urolesan, Pinosol. Menthol is applied externally in solutions for the relief of neuralgic pains, and as antiseptic and cooling agent in certain skin diseases. Internally it is an antiseptic. It is part of Alorom, Boromentol, Gevkamen, Cameton, Camphomen, Zelenin’s Drops, Menovasin, Pectussin.

23. Salviae Folia Salvia officinalis- SageLamiaceae • Constituents. Up to 2.5% of a greyish-yellow volatile oil containing borneol, pinene, thujone and cineol, bitter principles, resin and tannins. • Uses. Sage is used chiefly as a condiment but is also employed as a carminative in dyspepsia, also has antiseptic, astringent action. Salvin works as plant antibiotic due to the content of diterpenes; is used in treatment of gingivitis and stomatitis.

24. Eucalypti Folia Folia Eucalypti viminalisOleum EucalyptiEucalyptus globulus, Eucalyptus cinerea, Eucalyptus viminalisEnglish names: Eucalyptus, Blue Gum leaves, Australian Fever Tree, Iron Bark TreeMyrtaceae

26. CoriandriFructusCoriandrumsativum- CorianderApiaceae • Constituents. Up to 1% of volatile oil containing coriandrol (d-linalool) and d-pinene, etc.; fixed oil, calcium oxalate, tannins. • Uses. Aromatic stimulant, has spasmolitic and antibacterial properties. It is part of appetising, cholagogue, expectorant and anti-haemorrhoidal species, infusion- part of Flora, ether oil is part of Espol (anti-inflammation and pain-killing drug).

27. CarviFructusCarumcarvi L. CarawayApiaceae • Constituents. Volatile oil (5-7%), fixed oils, tannins, etc. The volatile oil contains carvone, limonene, dihydrocarvone, caryeol, and a small quantity of a base having a narcotic odour. • Uses. Stimulant, carminative, condiment, diuretic, diaphoretic and flavouring agent; source of oil of caraway. It is used in the food industry for flavouring bread, cheese and candy.

28. JuniperiFructusJuniperuscommunis- Juniper, Horse Savin BerriesCupressaceae • Constituents. From 0.3 to 1.5% of a VO containing the terpenes camphene and x-pinene, a sesquiterpene called cadinene; terpene alcohols borneol, one of which is terpineol; resin, fixed oils, up to 30% of dextrose, etc. A crystalline substance deposits in the oil at low temperatures known as juniper camphor. • Uses. Juniper berries are used for the preparation of juniper oil. The juniper oil has diuretic, antireumatic and antiseptic properties. Used as stimulating diuretic in chronic genito-urinary disorders.

29. Valerianae radix Valerianaofficinalis- Valerian, Wild, Great Wild, Cat’s ValerianValerianaceae • Constituents. Volatile oil (up to 2%) containing bornyl isovalerianate, bornyl formiate, bornyl acetate and bornyl butyrate, camphene, borneol and pinene; two alkaloids- chatinine and valerianine, a glucoside, resin, α-methylpyrryl ketone, stated to be narcotic, valeric, formic and acetic acids, tannins, sugar, etc. • Uses. Valerian is used as a calmative in nervousness and hysteria and as a carminative. Preparations- Valerian fluid extract, Valerian tincture, Valocordinum, Corvalolum, as ingredient of Species Sedativae.

30. Lavandulae Flores Lavandulaangustifolia L. Lamiaceae • Constituents. Up to 3% of VO containing esters, also linalool, geraniol, limonene and sesquiterpene; resin, tannins, etc. • Uses. Lavender flowers are chiefly used as a perfume. Livian has anti-inflammatory and pain-killing action and used to treat burns.

31. MP and MPM containing sesquiterpenoids

32. CalamiRhizomataAcoruscalamus- Sweet Flag, Sweet RootAraceae • Constituents. Vo (1.5to 3.5%) containing asaryl aldehyde, eugenol and asarone; a bitter glucoside called acorin; soft resin, starch, inulin, etc. • Uses. Carminative, aromatic bitter and stimulant; flavouring agent. Used in atonic dyspepsia and colic. Vicalin, Vicair and Herbogastrin are used for the treatment of ulcers.

33. BetulaeGemmaeBetulae Folia Betulapendula, BetulapubescensEnglish name- BirchBetulaceae • Constituents. VO 5-8% with balsamic odour, contained bicyclical sesquiterpenoid betulen and alcohol betulenol. • Uses. Medicines have diuretic, diaphoretic, cholagogue, spasmolytic, anti-inflammation, anti-viral, wound-heeling and antihelmintic actions. Medicines- infusion, tincture, Propobesan.