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The Chemistry and Pharmacology of Edelweiss: a Review

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The Chemistry and Pharmacology of Edelweiss: a Review Phytochem Rev (2017) 16:295–308 DOI 10.1007/s11101-016-9474-0 The chemistry and pharmacology of Edelweiss: a review Jan Tauchen . Ladislav Kokoska Received: 11 February 2016 / Accepted: 11 July 2016 / Published online: 15 July 2016 Ó Springer Science+Business Media Dordrecht 2016 Abstract Leontopodium nivale ssp. alpinum (syn. preparations and isolated compounds of Edelweiss Leontopodium alpinum) is a perennial herb commonly support the view that these might be used in the known as Edelweiss, which has a long tradition in development of agents with therapeutic benefit in Alpine countries and adjacent regions as a medicinal various human diseases. Some suggestions for further plant. This review discusses current knowledge on the research on chemical characterization and pharmaco- traditional uses, chemistry, biological activities and logical properties are also given in this review. toxicology of this species. Several different classes of compounds such as terpenoids (analogues of Keywords Asteraceae Á Leontopodium alpinum Á sesquiterpenes, bisabolenes), phenylpropanoids (phe- Leontopodium nivale Á Medicinal plant Á Secondary nolic acids, flavonoids, coumarins, lignans), fatty metabolites acids and polyacetylenes were previously isolated from various parts of Edelweiss. Different types of extracts and compounds derived from this plant have been found to possess a broad spectrum of pharma- Introduction cological activities on the cardiovascular and nervous systems. Furthermore, the plant have known anti- Leontopodium nivale ssp. alpinum (Cass.) Greuter inflammatory, antimicrobial, antioxidant and chemo- (family Asteraceae), commonly known as Edelweiss, protective effects. The observed pharmacological is a perennial heliophytic herb growing up to 20 cm activities as well as toxicological profile of high (Fig. 1) native to the Pyrenees, the European Alps, the Tatra and the Balkan Mountains, where it naturally occurs on limy soils, stony meadows and J. Tauchen even on rocks. It is usually found between 1000 and The Department of Quality of Agricultural Products, The 3400 m above sea level (Maugini 1962; Sugar 1971; Faculty of Agrobiology, Food and Natural Resources, The Siljak et al. 1974; Erhardt 1993;Ho¨randl et al. 2011; Czech University of Life Sciences Prague, Kamycka 129, Neblea et al. 2012; Khela 2013; Finkenzeller 2014). 165 21 Prague 6 – Suchdol, The Czech Republic The centre of diversity of the genus Leontopodium is L. Kokoska (&) located in Asia, comprising 41 species including some The Department of Crop Sciences and Agroforestry, The presumed hybrids. Only one species is native to Faculty of Tropical AgriSciences, The Czech University Europe: L. nivale (Ten.) Huet ex Hand.-Mazz (Handl- of Life Sciences Prague, Kamycka 129, 165 21 Prague 6 – Suchdol, The Czech Republic Mazzetti 1928; Lee et al. 2011; Safer et al. 2011a, b). e-mail: [email protected] So far, the relationship between L. nivale and L. 123 296 Phytochem Rev (2017) 16:295–308 applied as a compress (especially in the treatment of breast cancer) (Tabernaemontanus 1993; Dobner et al. 2003b). Today, extracts of the aerial parts of Edel- weiss are used for their antioxidant properties in cosmetic preparations such as sunscreen products (Schwaiger et al. 2005, 2006). Due to intensive collection from its natural habitats for various human needs, populations of this plant have significantly declined. The species is nowadays regarded as rare, however it is listed as Least Concern (LC) in the IUCN Red List of Threatened Species (Khela 2013). The collection of wild individuals of Edelweiss is currently forbidden by law in many countries (Blascakova et al. 2011; Keller and Vittoz 2015), hence the main bulk of its production comes from successful cultivation in Switzerland (Schwaiger et al. 2005, 2006). Besides which, Edelweiss has demonstrated promising results when propagated via cell tissue culture techniques, facilitating even more the commercial availability of this plant for industrial Fig. 1 Flowering individual of Edelweiss (Leontopodium uses (e.g. cosmetics, pharmacology) (Hook 1993; nivale ssp. alpinum (Cass.) Greuter). Photograph by courtesy Trejgell and Tretyn 2010). of Thomas Lichtenberg Because of its wide popularity, well-documented ethno-medicinal uses and scientifically confirmed pharmacological properties, Edelweiss has evoked alpinum has not been entirely resolved. Some authors renewed interest as a promising source material for the treat these as separate species (Blo¨ch et al. 2010), development of plant-derived drugs which might be while others recognize just one species with two used in clinical practice in the treatment of various subspecies (L. nivale ssp. nivale and L. nivale ssp. human diseases. alpinum, respectively) (Greuter 2003). The literature now contains an unfortunate combination of the approaches to two nomenclature, though the original Chemical composition name L. alpinum is most often employed. Edelweiss is a very important part of the cultural In a period of almost 50 years, several different classes heritage for people living in its native areas. This fact of secondary metabolites were isolated from various can be illustrated by various reports of its traditional plant parts of Edelweiss, with the main group being uses in folk medicine (Matthioli 1931). Extracts of terpenoids, phenylpropanoid derivatives and various different plant parts of Edelweiss were applied in the aliphatic compounds. A list of known Edelweiss treatment of several human and livestock diseases for constituents, including plant part(s) where particular conditions such as abdominal disorders, angina pec- compounds were detected is given in Table 1. toris and other heart diseases, bronchitis, diarrhoea, One of the first phytochemical investigations deal- dysentery, fever, pneumonitis, rheumatic pain, tonsil- ing with the terpenoid compounds of Edelweiss litis, and various types of cancers (Tabernaemontanus revealed that the roots are comprised of approximately 1993; Stuppner et al. 2002; Dobner et al. 2003a, b; 0.6–2 % essential oil, containing more than 30 com- Speroni et al. 2006; Hornick et al. 2008; Daniela et al. pounds, of which 20 were detected in concentrations 2012). Historical literature records Edelweiss being above 1 % with 2 compounds representing nearly applied either orally—i.e. the herb was boiled in wine 60 % of the oil (Bicchi et al. 1975; Comey et al. 1992a; and mixed with milk; or topically, where the material Hook 1994). Further detailed investigation into this was boiled in water and the extract so acquired was essential oil, as obtained by steam distillation from 123 Phytochem Rev (2017) 16:295–308 297 Table 1 Secondary metabolites of Edelweiss (Leontopodium nivale ssp. alpinum (Cass.) Greuter) Structure Compound* Plant part(s)a References number Terpenoids 1 isocomene Hairy root cultures, roots Grey et al. (1999), Hornick et al. (2008) 2 14-acetoxyisocomene Hairy root cultures, roots Grey et al. (1999), Hornick et al. (2008) 3 methyl isocomen-14-oate Hairy root cultures, roots (Grey et al. 1999) 4 b-isocomene Roots Schwaiger et al. (2002), Dobner et al. (2003b), Hornick et al. (2008) 5 silphinene Roots Schwaiger et al. (2002), Dobner et al. (2003b), Hornick et al. (2008) 6 silphiperfolene acetate Roots Schwaiger et al. (2002), Dobner et al. (2003b), Hornick et al. (2008) 7 modhephene Hairy root cultures, roots Grey et al. (1999), Schwaiger et al. (2002), Dobner et al. (2003b), Hornick et al. (2008) 8 15-acetoxymodhephene Hairy root cultures, roots Grey et al. (1999), Dobner et al. (2003a), Hornick et al. (2008) 9 6-acetoxy-3(15),7(14)-caryo-phylladiene Hairy root cultures, roots Grey et al. (1999) 10 T-cadinol (cedrelanol) Roots Schwaiger et al. (2004) 11 (1R*,3S*,4R*,6S*)-4,9-bis(acetoxy)-1- Roots Stuppner et al. (2002) [(2Z)-2-methylbut-2-enoyloxy]bisabol- 10(11)-eneb 12 (1R*,4S*,6R*)-4,9-bis(acetoxy)-1-[(2Z)- Roots Stuppner et al. (2002) 2-methylbut-2-enoyloxy]bisabol- 2(3),10(11)-dienec 13 (1R*,4R*,5R,6R*)-1,4,5-tris(acetoxy)-9- Roots Stuppner et al. (2002) [(2Z)-2-methylbut-2-enoyloxy]bisabol- 2(3),10(11)-diened 14 (1R*,3S*,4R*,6S*)-9-(acetoxy)-4- Roots Schwaiger et al. (2004) hydroxy-1-[(2Z)-2-methylbut-2- enoyloxy]bisabol-10(11)-ene 15 sitosterol Cell suspension cultures, roots and Hennessy et al. (1989) leaves obtained by micropropagation 16 ent-kaur-16-en-19-oate Roots Schwaiger et al. (2004) 17 methyl ent-7a,9a-dihydroxy-15b-[(2Z)-2- Roots Schwaiger et al. (2004) methyl-but-2-enoyloxy]kaur-16-en-19- oate Phenylpropanoid derivatives 18 luteolin Aerial parts Tira et al. (1970), Schwaiger et al. (2006) 19 apigenin Aerial parts Schwaiger et al. (2006) 123 298 Phytochem Rev (2017) 16:295–308 Table 1 continued Structure Compound* Plant part(s)a References number 20 luteolin-7,40-di-O-b-D-glucoside Aerial parts Schwaiger et al. (2006) 21 luteolin-7-O-b-D-glucoside Aerial parts Tira et al. (1970), Schwaiger et al. (2006) 22 luteolin-40-O-b-D-glucoside Aerial parts Tira et al. (1970), Schwaiger et al. (2006) 23 luteolin-30-O-b-D-glucoside Aerial parts Schwaiger et al. (2006) 24 6-hydroxy-luteolin-7-O-b-D-glucoside Aerial parts Schwaiger et al. (2006) 25 quercetin-3-O-b-D-glucoside Aerial parts Schwaiger et al. (2006) 26 apigenin-7-O-b-D-glucoside Aerial parts Schwaiger et al. (2006) 27 chrysoeriol-7-O-b-D-glucoside Aerial parts Schwaiger et al. (2006) 28 (S)-2,6-dimethylchroman-4-one Hairy root cultures, roots Comey et al. (1997) 29 1-{(2R*,3S*)-2-[1- Roots Dobner et al. (2003a) (hydroxymethyl)vinyl]-3-[b-D- glucosyloxy]-2,3-dihydro-1-benzofuran- 5-yl}-ethanone 30 obliquin Roots Dobner et al. (2003a) 31 5-hydroxyobliquin Roots Dobner et al. (2003a) 32 5-methoxyobliquin Roots Dobner et al. (2003a) 33 chlorogenic acid Cell suspension cultures, roots and Hennessy et al. (1989), Schwaiger leaves obtained by et al. (2006) micropropagation, roots, aerial parts 34 3,4-di-O-caffeoylquinic acid Cell suspension cultures, roots and Hennessy et al.
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