Krystyna NOWAK, Małgorzata JAWORSKA, Jan OGONOWSKI Institute of Chemistry and Organic Technology, Cracow University of Technology, Cracow, Poland
Abstract:
The aim of this study is to present the characteristics of biologically active compounds contained in the rosemary (such as rosemary oil, flavonoids, terpenes, phenolic acids) and their use in pharmaceutical, cosmetic and food industries.
Please cite as: CHEMIK 2013, 67, 2, 133-138
Introduction
Rosemary ( Rosmarinus officinalis L.) is an aromatic, evergreen plant which grows in the wilderness on the coasts of Mediterranean Sea and in the southern part of Crimea. In Poland the only possibility is to grow it in a greenhouse. Rosemary used to be well known and grown in the ancient times. The Romes called it a flower of the sea. Its name derives from Latin from words rosa- rose and marinus ? nautical. The well smelled scent of rosemary on the seas indicated the moment of approaching a shore. The most recognizable herbalist of Middle Ages, Saint Hildgerard from Bingen used to describe rosemary like that ? ?.. It makes a human younger and more attractive. ?..The outer use of sap from it as eardrops cures the ailing hearing? [1, 2]. The priest Sebastian Kneipp claims, that ? It would be a shame if the household?s first aid kit did not store this herb? [3].
Fundamental substances which rosemary contains
Rosemary is rich in compounds which show biological effect. Apart from etherical oil the raw material contains flavonoids (luteolin, genkwanin, diosmetin and their cardiac glycosides), tannin (8%) and di ? and triterpenes, phenol acids, and among them it has a rosemary acid which was separated for the first time from rosemary in the middle of XX century [4, 5].
Rosemary Oil
Rosemary is a part of gland hair, which appears in abundance on the bottom side of leaves and flowers, and in minimal amount on the stalk. Leaves of rosemary and the herb of it are also a raw oil material. Leaves in bloom also contain 1.5% of oil, in the dried leaves the content is different and equals about 1-2.5% , and in the herb 0.4 ? 2% [1, 6].
The oil is acquired in the process of distillation with vapor. The little, one-year-lasting branches are automatically sent to undergo distillation with vapor. The simplest outer distillatory devices allow to obtain an oil with effectiveness of 0.5 %. The efficiency of the oil can be improved (1-1.5%) if it id distilled with the heated vapor [1].
Rosemary oil is acquired also using hydro distillation method and by extraction with carbon dioxide at the critical stage. Such an oil is richer in high boiling air ingredients, its smell is more alike the smell of a plant [1]. The oil is either a colorless or light yellow liquid which may become darker while long storage. The intensive, herbal-wooden smell is characteristic for it and it sometimes smells like camphor. The taste is spicy, bitter and cold on the other hand [1, 6, 7].
The content of the oil, similarly to its properties, depends on the place where it is grown and on the part of the plant (young leaves, old leaves, blooms) from which it is obtained. The climatic conditions, time of harvesting and form of obtaining it can also influence its content. Table 1 shows the physical and chemical properties of a Spanish rosemary oil. Almost half of worldwide production of rosemary oil is obtained in Spain [1].
The rosemary oil was researched and it is proved that there are 200 ingredients. The main ingredient of the oil is 1,8 ?cineole, whose content fluctuates around 20 to 50%. There are also carbohydrates like: camphore, camphene and the dominating one alfa-pinene (about 20%) (Fig. 1). Globally they exist there in the amount of 40 -55%. The are the reason for a intensive smell.
Terpenes
The major terpenes which make the content of rosemary are: bitter diterpene lactine, carnosol (1.2%) and oleanic acid (+/- 1%) and ursolic acid (+/- 3%) (Fig. 2).
Carnosole has an antibiotic effect, oleans acid has antyhepathotoxical, antiinfamation and antiulcer properties, however the urosolic acid has cytotoxical and antyinflamation properties. Moreover it decreases the bad cholesterol concentration in the blood [8, 9].
Flavonoids
Flavonoids are the largest group of phenol compounds which is well-known in the natural world of plants. Because of their ability to seal the blood vessels they were called the vitamins of transmission (vitamin P). The are currently known as bioflavonoids. Luteolin, genkwanina, diosmetin are in the free and glycosidic form in the rosemary (Fig. 3).
More and more people took deeper interest in bioflavonoids in the eighties of XX century when it was discovered that they have other properties than the ones mentioned before. Namely, it was revealed that rosemary is a perfect antioxidant, so it was called a natural antioxidants [10].
Phenolic Acids
Phenolic acids are extremely significant compounds which protect the cells from so called ?oxidatical stress?. They appear in the free and glycosidic form. The most important phenol acids which rosemary contain are the caffeic acid and a rosmarinic acid (Fig. 4).
Caffeic acid (3,4?dihydroxycinnamon) is widely recognized among flowery plants. It appears in the free form or in a form of depside with quinic acid. Depsides are compound of two or more fenoloacids [11]. They have bacteriostatic, anti inflammatory and immunotropic properties [8].
Rosmarinic acid is an ester of coffee and alpha hydroxydihydrocaffeic acid. The latter is called depside. Alike all depsides it is commonly recognized in nature. Its existence is proved in 1 g of the raw material of over than 100 types of plants where it appears in amount of 0.01 mg up to 78 mg. The content of rosemary acid in leaves oscillates about 0.2-4.3%. That acid appears in plants I a free form, which is cestrified, and also as a cohesion of oligomeres. Despite not having abilities to tan a raw skin it belongs to the group of coffeetanoids, its related compounds with dye [11]. Pharmacological activity of the rosmarinic acid is related to its structure, and with the cooperation of two aids which create the molecule. It is also connected with the existence of four free hydro sole groups which are in an orto position towards one another and with the presence of a double compound in the coal chain.
At the end of XX century the research was carried out on animals. Not only the acid therapeutic potential was analyzed but also its metabolic properties were explained. It was concluded that the rosmarinic acid is absorbed properly from the alimentary canal and from the skin. It was also proved that the acid stabilizes biological membrane, protects from the UV rays and radicals and it is an antioxidant. The activity is a result of accumulation of both radicals which form the structure of the acid. The possibility to catch radicals and to hinder their toxical influence on acid structures, proteins, lipids and fatty acid is a natural factor preventing the cancerogenesis process [12]. It has anti inflammation, antibacterial, antivirus, antihormone properties and possibly calms the central nervous system down. Like others poliphenols it has antimicroorganisms properties and it is active against viruses like HSV-1 (herpes type 1) and other viruses of human immunology deficiency (HIV 1) [12].
The use of rosemary in treatment
Both, rosemary oil and its herb are used in many different disorders? treatment. It is broadly used on the outer part of the body to lessen the rheumatic pain because it works as a painkiller. Widening of the vessels makes the blood circulation more smooth. It is said to be bacteriostatic and antibacterial [13]. The oil is commonly used in aromatherapy as well, especially to massages, baths and inhalations and padding of various skin disorders [1]. The leaves of rosemary not only prevent the cramps of intestines muscles and urinal pipes but also improve the digestion system and intestines activity. Similarly to the rosemary oil the extract of rosemary are advisable to be applied to painful rheumatic disorders and pains in the muscles [14]. Extracts from alcohol and water-alcohol from the herb have a strong antioxygenic and anty immunological properties [1].
The use of rosemary in cosmetic industry
Cosmetic industry, like medical treatment uses the oil and the herb of rosemary in various perfumes and cosmetics. Góra and Lis [1] present the following scent characteristic of rosemary oil (Tab. 2). For perfumery purpose the rosemary oil is applied when it is secluded from the specific types of the plant. Seclusion means that from the oil mono ?and sesquiterpenes hydrocarbon is removed using the method of column chromatography. The received oil has a very delicate, herbal scent with the upper note of scent, and the treebalsamic bottom one.
The rosemary oil and its extracts are widely added to lotions, balms, after shave and liquids and to shampoos and soaps as well. The extracts from rosemary are extremely nutritious, relaxing and make hair shiny, dark and fast growing. Flavonoids, because of their origin, are the group of substances which people take a deep interest in, especially in cosmetic industry. Antioxidant factors are mainly used in cosmetics which prevent skin aging, but it cannot be forgotten that they also prolong the expiry date of cosmetics. For that reason there is a widespread manufacture of cosmetics including herbal extracts and rosemary [15].
The most popular liquid to care which used to be known across Europe was the rosemary perfume called Larendogra. It was applied to face complexion and neck to rinse them. It was also famous to apply it to the whole body to cure various pains and itches. The name of the water derives from the saying L?eau de la reine d?Hongrie. It was invented by the Queen of Hungary, sister of Kazimierz Wielki, Elżbieta Piastówna (1305-1380). It is supposed that the Queen reaching the age 72 was able to cur rheumatism due to the rosemary water. The recipe for the water was the following: three cloves of fresh rosemary and one clove of lavender should be soaked in spirits which up to 5 cm high and should be left for a fortnight in a dark place, then it must be soaked again as it would be to just one use [16].
Rosemary in food industry
Rosemary oil is used as a scent liquid and to product tinned meat and fish. Dried leaves of rosemary are recommended by the food specialists and diabetics advisors of Mediterranean cuisine. There was a special research carried out on the influence of rosemary on endurance of poultry and turkey meat. Poultry is characterized by high content of unsaturated fatty acids and this is why the product made of it is prone to reactions of lipids oxidation. Adding rosemary to meat products slows down the process of oxidation and prevents disadvantageous changes through oxidation. Moreover, it improves the smell of meat products [17, 18]. The herb of rosemary is an ingredient of multiple liquors and alcohols. Rosemary cordial with thyme is obtained when the dried leaves of rosemary and 1 g of thyme are soaked in 0.5 dm3 of 50% pure vodka and it is left to get soaked for two weeks [19].
Summary
Rosemary is rich in biological active compounds. Rosemary acid has been extracted from the herb for the first time and because of its pharmacological activity it arouses interest among scientists and pharmacists.
Literature
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Krystyna NOWAK ? Ph. D., works at the Institute of Organic Chemistry and Technology, Cracow University of Technology. Specialization: heterocyclic chemistry, natural resources.
Małgorzata JAWORSKA ? M.Sc., graduated from the Faculty of Chemical Engineering and Technology of the Cracow University of Technology in 2008. Now she is a doctoral student at the Institute of Organic Chemistry and Technology of the Cracow University of Technology. She specializes in cosmetic technology, especially in nanoemulsions.
e-mail: , phone:
Jan OGONOWSKI ? Professor (Ph. D., Eng) is head of the Department of Technology of Organic and Refinery Processes at the Institute of Organic Chemistry and Technology. Specialization: technology, organic catalysis, technology low tonnage products.