Parthenolide from the aerial parts of Tanacetum larvatum
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Subject and source
The genus Tanacetum L. comprises ca 150 species that commonly occur in Europe from the Mediterranean to Persia. Tanacetum larvatum (Gris.) Kanitz, the examination of which is reported, is distributed on elevated rocky terrains in Albania, Serbia (Kosovo) and Montenegro (Gajić, 1975).
Aerial parts of T. larvatum were collected in Montenegro on two locations: crop a on mountain Komovi (altitutude 1800 m, 12 July 1998) and crop b on mountain Babji Zub (altitude ca 1500 m, 30 June 1999). Voucher
Previous work
Previous phytochemical investigations of the genus Tanacetum, wild-growing in Serbia involving T. parthenium, T. serotinum, T. vulgare, T. macrophyllum and T. corymbosum revealed several sesquiterpene lactones of the eudesmanolide, germacranolide and guaianolide type (Ristić, 1983; Milosavljević et al., 1999 and references therein). T. larvatum has not been studied before.
Present study
The extract (MeOH/Et2O/Petrol, 1:1:1) of ground air-dried aerial parts of the crop a (270 g), prepared according to the usual procedure for isolation of sesquiterpene lactones (Bohlmann et al., 1984) was subjected to a combination of dry-column flash chromatography, MPLC and silica gel CC to yield two sesquiterpene lactones, the germacranolide parthenolide (1, 35 mg) (Govindachari et al., 1965; El-Feraly et al., 1979) and the eudesmanolide, douglanine (2, 21 mg) (Matsueda and Geissman, 1967).
Chemotaxonomic and ecological significance
Sesquiterpene lactones are among the major constituents in species belonging to the genus Tanacetum. As reported (Duke database, 2000) the species with highest contents of 1 are T. parthenium (feverfew) and T. vulgare (tansy). The richest source of 1 so far has been in cultivated variety of feverfew from UK, whose leaves have been used for centuries as a treatment for migraine and to relieve painful periods. Feverfew contains 1 up to 1.38% in flower tops, 0.95% in leaves and 0.08% in stalks (
Uncited Reference
Phytochemical and Ethnobotanical Databases, 2000.
Acknowledgements
Financial support from the Ministry of Science and Technology of Republic of Serbia is gratefully acknowledged. We are also very grateful to Daniel Vincek, Botanical garden, Kolašin (Montenegro) for the immense help in identification and collection of the plant.
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2015, Industrial Crops and ProductsCitation Excerpt :Many studies have been reported on the essential oil composition of various Tanacetum species (El-Shazly et al., 2002; Goren et al., 2001; Greche et al., 2000; Judzentiene and Mockute, 2005; Kandemir et al., 2008; Majed-Jabari et al., 2002; Marongiu et al., 2009; Mockute and Judzentiene, 2004; Monfared et al., 2002; Piras et al., 2014; Polatoğlu et al., 2011; Rohloff et al., 2004; Weyerstahl et al., 1999) and camphor, 1,8-cineole, α-thujone, carvone, thymol, trans-sabinyl acetate, borneol, caryophyllene oxide, (E)-myroxide, sabinene, bornyl acetate, isopulegone and artemisia ketone were identified as the major constituents. This genus is also found to contain sesquiterpene lactones (Aljancic et al., 2001; Mahmood et al., 2002), a large group of molecules with several biological activities (Chaturvedi, 2011; Ghantous et al., 2010; Kreuger et al., 2012; Lesiak et al., 2010; Merfort, 2011; Wagner et al., 2008; Zhang et al., 2005). The genus Tanacetum is represented in Italy by 9 taxa (Conti et al., 2005) and in Sardinia there is only one spontaneous species, Tanacetum audibertii (Req.)
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