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Variability of Composition of Essential Oil and Coumarin Compounds of Angelica Archangelica L

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Variability of Composition of Essential Oil and Coumarin Compounds of Angelica Archangelica L International journal edited by the Institute of Natural Fibres and Medicinal Plants Vol. 65 No. 4 2019 Received: 2019-11-27 DOI: 10.2478/hepo-2019-0027 Accepted: 2019-12-20 Available online: 2019-12-31 REVIEW PAPER EXPERIMENTAL PAPER Variability of composition of essential oil and coumarin compounds of Angelica archangelica L. ANNA FORYCKA*, WALDEMAR BUCHWALD Department of Botany, Breeding and Agricultural Technology of Medicinal Plants Institute of Natural Fibres and Medicinal Plants Kolejowa 2 62-064 Plewiska *corresponding author: e-mail: [email protected] Summary The medicinal and culinary properties of Angelica archangelica L. have been known and valued since the Middle Ages. Ingredients of essential oil and coumarins found in this plant are to a large degree responsible for its pharmacological activity. This study is a review of the literature of the most important biologically active compounds present in herbal raw materials: root (rhizome with roots) and angelica fruits. Research shows that the content of individual compounds of the essential oil and coumarin fraction is variable, which may point to a large intraspecific variation. Therefore, these compounds may be good markers for identify- ing taxa or chemotypes in chemotaxonomic research valuable for the herbal medicine and pharmaceutical industry. Key words: Angelica archangelica, essential oil, coumarins, furanocoumarins, chemical composi- tion, chemotaxonomy Słowa kluczowe: Angelica archangelica, olejek eteryczny, kumaryny, furanokumaryny, skład chemiczny, chemotaksonomia INTRODUCTION of the quality, safety and biological activity [1, 2]. Despite the limitations of the analytical methods, In modern phytotherapy, the demand for precise the description and chemical characterization of quantitative and qualitative data concerning herbal variability within the species treated and used as a raw material used in the production of medicines medicinal plant should be complemented. Mate- has been rising, mainly due to restrictive control rial from the same species may vary significantly in Herba Pol 2019; 65(4): 62-75 Variability of composition of essential oil and coumarin compounds of Angelica archangelica L. 63 composition of secondary metabolites [3]. that are difficult to notice. In the literature, there The genus Angelica (Apiaceae family) is a large are varieties of A. archangelica subsp. archangelica: and taxonomically complex genus consisting of var. archangelica, var. norvegica (currently included many (90-110) species and varieties, among which in var. archangelica), var. sativa (Mill.) Rikli, var. de- over 60 species are widely recognized as medicinal currens (Lebed.) Weinert [31]. Their morphological plants [4]. It is considered to be a highly polymor- criteria are not always specified. Occurrence of var. phic group due to huge anatomical diversity of fruit archangelica and var. sativa concerns Europe, while and leaf morphology [5]. Due to that fact is very dif- var. decurrens are distinguished in the Asian part of ficult to distinguishing between Angelica taxa [6]. angelica range (eastern Siberia). Pharmacologic and One of the most important representatives of this chemotaxonomic studies as well as phytochemical genus is the Angelica archangelica species, a medici- discoveries are helpful in solving taxonomic prob- nal and aromatic plant native to Europe, with a long lems encountered by taxonomists [32]. They often history of use both for medicinal purposes and as allow not only to differentiate taxa that are difficult a vegetable [7]. Its dried root and essential oil are to mark on the basis of morphological criteria, but used for the production of liqueurs, perfumes and also to identify the chemical phenotypes, which can spice extracts. The medicinal raw material men- be particularly valuable in the case of plants used tioned in Europaean Pharmacopoeia 9.0 [8] is the in herbal and pharmaceutical industries or as food. angelica root (rhizome with roots) containing es- Studies indicate that the level of secondary metabo- sential oil and coumarins. Flavonoids, organic acids, lites, which is influenced by genetic regulation, may steroids, saponins, alkaloids, simple sugars and fats vary within the species depending on geographic are also present in the raw material [9]. It can effec- origin [33-35]. tively regulate digestive system, stimulate immune In this context, the analysis of intraspecific vari- system and improve resistance of the nervous sys- ability of angelica, in terms of main secondary me- tem in anxiety and dementia [10-13]. It also exhibits tabolites, such as essential oils and coumarins accu- bactericidal, fungicidal and anti-inflammatory ef- mulated in great amounts in the roots and fruit of fects [14-16]. The in vitro and in vivo extracts from this species, seems to be interesting. the root of angelica have antitumor potential against It should be taken into account that the chemi- breast cancer cells [17]. The fruits of angelica were cal composition of the analyzed raw material is previously used in smaller scale. Nowadays, they are influenced by various parameters, such as genetic considered to be a rich source of coumarin com- and environmental factors, the age of the plant and pounds with potentially wide range of applications the type of organ tested, as well as the harvesting in various therapeutic purposes [3, 18-20]. method, raw material treatment and analytical tech- Currently, two taxa of A. archangelica (Aa) are niques used. distinguished as subspecies: subsp. archangelica (former Archangelica officinalis Hoffm.) and subsp. litoralis (Fies) Thell. (previously Archangelica litora- CHEMICAL CHARACTERISTICS OF lis Fries) [21]. ESSENTIAL OIL OF ANGELICA The natural habitat of the first subspecies is the mountainous areas of Europe, the Arctic, the Cauca- Essential oil is obtained from raw material using sus and the Himalayas [22], while subsp. litoralis is classic and advanced techniques. The most impor- found on the sea coasts and river banks, in moist for- tant and most commonly used methods of oil iso- ests and thickets, as well as in the meadows of north- lation are steam distillation and hydrodistillation, ern Europe and Scandinavia [23]. Angelica is culti- recently also supercritical fluid extraction (SFE). vated as a medicinal and aromatic plant in northern, For qualitative analysis of the oil and isolation of its central and western Europe. This species spreads and compounds gas chromatography coupled with mass as a synanthropic plant, occupies new areas [24-29]. spectrometry (GC-MS) is widely used. The plants of both taxa differ in their smell and taste, Essential oils are multi-compound mixtures of which indicates intraspecific variability in the chem- terpenoid hydrocarbons including mono-, sesqui- ical composition. Aa subsp. litoralis is characterized and diterpene compounds, non‐terpenoid hydro- by sharper smell and taste than Aa subsp. archangel- carbons and their oxygenated derivatives [36]. One ica, some authors consider it to be inedible [30]. oil can contain several dozen different compounds. However, two subspecies are generally not separated In most oils one main ingredient or a mixture of in phytotherapy, due to morphological differences several main ingredients gives the fragrance to the Vol. 65 No. 4 2019 64 A. Forycka, W. Buchwald whole oil. Roots and fruits are particularly rich in in which β-phellandrene, α-pinene, sabinene and oils. The main ingredients found in angelica essen- myrcene are the dominating ones. Essential oil from tial oil are listed in table 1. plant roots growing in Scandinavia usually con- The presence and proportions of individual in- tains β-phellandrene or β-phellandrene as a main gredients determine the aromatic properties of the ingredient along with α-pinene, which constitute oil. For example, high content of β-phellandrene about 50% of the monoterpenes fraction [38, 42, gives the peppery-minty and slightly citrus aroma 46, 49]. The highest values of β-phellandrene were [37]. High concentrations of α- and β-pinen are found in raw material obtained from northern Eu- responsible for the terpene fragrance. The pres- rope (Finland, Norway), where this type of oil is the ence of 15-pentadecanolide in the oil is manifested most common one. As the dominant compound by a characteristic ”musky” aroma [38]. Further- of the root, β-phellandrene was also found in Cen- more, some substances such as oxidized 3-carene, tral and Eastern Europe, but concentrations of this limonene and α-pinene derivatives can cause aller- compound were lower [40]. In most materials from gic symptoms [39] and therefore are not desirable in Central, Southern and Eastern Europe, the main large amounts in medicinal raw material. compound of the oil in angelica root was α-pinene [14, 43, 50-53]. Sabinene was found in large quan- tities in raw material from western and northern Root parts of Finland [45, 54]. In the root of cultivated var. sativa, sabinene was the dominant compound Angelica root contains from 0.2 to 0.5% essential oil of the oil [49]. In one Finnish population, the domi- [40]. More than 62 to 100 compounds were identi- nant compound of the isolated oil was myrcene [45]. fied in the chemical composition of the oil with the A significant substance among main oil compounds use of new analytical methods [41-43]. was also 3-carene. It was often present in high con- The largest fraction of the essential oil from angel- centration as the second or third most important es- ica root are hydrocarbon monoterpens (±60–88% sential oil compound, and in some cases as a main of aromatic compounds of the oil) and oxygenated compound [55]. It has been observed that popula- compounds [38, 44, 45]. A significant fraction of the tions of different origins may differ in the presence oil are sesquiterpene hydrocarbons, which account or absence of 3-carene [54]. Moreover, there is a for 8% in steam distillation [42] and for 10–24.7% in high diversity of chemical oil composition among Soxhlet extracts [46]. This hydrocarbon group con- aforementioned angelica taxa. Forsén [38] assessed sisted of numerous compounds that were detected the composition and content of essential oil of two in small amounts.
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