Terpenoids, essential oil composition, fatty acid profile, and biological activities of Anatolian Salvia fruticosa Mill.
The hexane and dichloromethane extracts, obtained by re-extraction of the methanol extract of Salvia fruticosa Mill., afforded 7 diterpenoids (carnosol, carnosic acid, carnosic acid 12-methyl ether, rosmadial, isorosmanol, ferruginol, and manool), 4 triterpenoids (a -amyryltetracosanoate, oleanolic acid, ursolic acid, and erythrodiol), a steroid (3-acetylsitosterol), and a flavone (salvigenin). The galls (apples) of the collected plant were separately extracted with hexane to afford fatty acids composed mainly of oleic acid (29%), palmitoleic acid (29%), and stearic acid (23.20%), which exhibited high anticholinesterase activity, particularly against BChE. The essential oil, obtained from the aerial parts of the plant, exhibited high AChE inhibitory activity, consisting of mainly 1,8-cineol (58.89%). The antioxidant activity according to 6 complementary tests and anticholinesterase potential of the methanol extracts and triterpenoids a-amyryltetracosanoate, oleanolic acid, ursolic acid, and sitosterol acetate were also investigated, and methanol extract exhibited the highest antioxidant and anticholinesterase activity, surpassing the other tested extracts and pure compounds.
Terpenoids, essential oil composition, fatty acid profile, and biological activities of Anatolian Salvia fruticosa Mill
The hexane and dichloromethane extracts, obtained by re-extraction of the methanol extract of Salvia fruticosa Mill., afforded 7 diterpenoids (carnosol, carnosic acid, carnosic acid 12-methyl ether, rosmadial, isorosmanol, ferruginol, and manool), 4 triterpenoids (a -amyryltetracosanoate, oleanolic acid, ursolic acid, and erythrodiol), a steroid (3-acetylsitosterol), and a flavone (salvigenin). The galls (apples) of the collected plant were separately extracted with hexane to afford fatty acids composed mainly of oleic acid (29%), palmitoleic acid (29%), and stearic acid (23.20%), which exhibited high anticholinesterase activity, particularly against BChE. The essential oil, obtained from the aerial parts of the plant, exhibited high AChE inhibitory activity, consisting of mainly 1,8-cineol (58.89%). The antioxidant activity according to 6 complementary tests and anticholinesterase potential of the methanol extracts and triterpenoids a-amyryltetracosanoate, oleanolic acid, ursolic acid, and sitosterol acetate were also investigated, and methanol extract exhibited the highest antioxidant and anticholinesterase activity, surpassing the other tested extracts and pure compounds.
___
- Wu, Y. B.; Ni, Z. Y.; Shi, Q. W.; Dong, M.; Kiyota, H.; Gu, Y. C.; Cong, B. Chem. Rev. 2012, 112, 5967–6026. Ulubelen, A.; Top¸ cu, G.; S¨ onmez, U.; Eri¸s, C.; ¨ Ozgen, U. Phytochemistry 1996, 43, 431–434.
- Aydo˘ gmu¸s, Z.; Ye¸silyurt, V.; Top¸ cu, G. Nat. Prod. Res. 2006, 20, 775–781.
- Top¸ cu, G.; Ulubelen, A.; Tam, T. C. M.; Che, C. T. Phytochemistry 1996, 42, 1089–1092.
- Rustaiyan, A.; Masoudi, S.; Tabatabaei-Anaraki, M. Nat. Prod. Commun. 2007, 2, 1031–1042.
- Moghaddam, F. M.; Farimani, M. M.; Seirafi, M.; Taheri, S.; Khavasi, H. R. J. Nat. Prod. 2010, 73, 1601–1605. Ulubelen, A. Phytochemistry 2003, 64, 395–399.
- Zhou, L. M.; Zuo, Z.; Chow, M. S. S. J. Clin. Pharmacol. 2005, 45, 1345–1359.
- Top¸ cu, G.; T¨ urkmen, Z.; Schilling, J. K.; Kingston, D. G. I.; Pezzuto, J. M.; Ulubelen, A. Pharm. Biol. 2008, 46, 180–184.
- Kolak, U.; Ari, S.; Birman, H.; Hasan¸ cebi, S; Ulubelen, A. Planta Med. 2001, 67, 761–763.
- Scholey, A. B.; Tildesley, N. T. J.; Ballard, C. G.; Wesnes, K. A.; Tasker, A.; Perry, E. K.; Kennedy, D. O. Psychopharmacology 2008, 198, 127–139
- C ¸ ulhao˘ glu, B.; Yapar, G.; Dirmenci, T.; Top¸ cu, G. Nat. Prod. Res. 2012, 27, 438–447.
- Howes, M. J. R.; Perry, N. S. L.; Houghton, P. J. Phytother. Res. 2003, 17, 1–18.
- Top¸ cu, G.; Erta¸s, A.; Kolak, U.; ¨ Ozt¨ urk, M.; Ulubelen, A . Arkivoc. 2007, 7, 195–208.
- Kabouche, A.; Kabouche, Z.; ¨ Ozt¨ urk, M.; Kolak, U.; Top¸ cu, G. Food Chem. 2007, 102, 1281–1287.
- Tel, G.; ¨ Ozt¨ urk, M.; Duru, M. E.; Harmandar, M.; Top¸ cu, G. Food Chem. Toxicol. 2010, 48, 3189–3193.
- World Checklist of Selected Plant Families, Kew Royal Botanic Gardens. apps.kew.org/wcsp Baytop, T. Therapy with Medicinal Plants in Turkey (Past and Present), Publications of the ˙Istanbul University, ˙Istanbul, 1984.
- Figueredo, G.; ¨ Unver, A.; Chalchat, J.C.; Arslan, D.; ¨ Ozcan, M. M. J. Food Biochem. 2012, 36, 334–343.
- Ulubelen, A.; ¨ Ozt¨ urk, S.; I¸sıldatıcı, S. J. Pharm. Sci. 1968, 57, 1037–1038.
- Ulubelen A. Planta Med. 1990, 56, 82–83.
- Ko¸sar, M.; Tunalıer, Z.; ¨ Ozek, T.; K¨ urk¸ c¨ u˘ glu, M.; Ba¸ser, K. H. C. Z. Naturforsch C. 2005, 60, 501–504.
- Papageorgiou, V.; Gardeli, C.; Mallouchos, A.; Papaioannou, M.; Komaitis, M. J. Agric. Food Chem. 2008, 56, 7254–7264.
- Pitarokili, D.; Tzakou, O.; Loukis, A; Harvala, C. J. Agric. Food Chem. 2003, 51, 3294–3301.
- Skoula, M.; Abbes, J.; Johnson, C. Biochem. Syst. Ecol. 2000, 28, 551–561.
- Al-Kalaldeh, J. Z.; Abu-Dahab, R.; Afifi, F. U. Nutrition Res. 2010, 30, 271–278.
- Longaray Delamare, A. P.; Moschen-Pistorello, I. T.; Artico, L.; Atti-Serafini, L.; Echeverrigaray, S. Food Chem. 2007, 100, 603–608.
- Pierozan, M. K.; Pauletti, G. F.; Cristina, A.; Lerin, L. A.; Luccio, M. D. I.; Mossi, A. J.; Atti-serafini, L.; Cansian, L.; Vladimir, J. Analysis 2009, 29, 764–770.
- Schwarz, K.; Ternesarin, W. Z Lebensm Unters Forsch. 1992, 195, 99–103.
- Pukalskas, A.; Van Beek, T. A.; De Waard, P. J. Chromatogr. A. 2005, 1074, 81–88.
- Djarmati, Z.; Jankov, R. M.; Djordjevic, A.; Ribar, B.; Lazar, D.; Engel, P. Phytochemistry 1992, 31, 1307–1309. Nakatani, N.; Inatani, R. Agric. Biol. Chem. 1983, 47, 353–358.
- Nakatani, N.; Inatani, R. Agric. Biol. Chem. 1984, 48, 2081–2085.
- De Carvalho, M. S.; Babtistella, L. H. B.; Imamura, P. M. Magn. Reson. Chem. 2008, 46, 381–386.
- Pereira, A. S.; Carbonell, S. A.; Neto, F. R. A.; Amaral, A. C.F.; Barnes, R. A. J. Chromatogr. A. 2002, 947, 255–265.
- Luis, J. G.; Quinones, W.; Grillo, T. A.; Kishi, M. P. Phytochemistry 1994, 35, 1373–1374.
- Miura K.; Kikuzaki, H.; Nakatani, N. J. Agr. Food Chem. 2002, 50, 1845–1851.
- Ulubelen, A.; Miski, M.; Mabry, T. J. Nat. Prod. 1981, 44, 119–124.
- Adams, R. P. Identification of Essential Oil by Ion Trap Mass Spectroscopy. Academic Press: New York, 1989.
- ¨ Ozt¨ urk, M.; Duru, M. E.; Kıvrak, S ¸.; Mercan-Do˘ gan, N.; T¨ urko˘ glu, A.; ¨ Ozler, M. A. Food Chem. Toxicol. 2011, 49, 1353–1360.
- Ellman, G. L.; Courtney, K. D.; Andres, V.; Featherstone, R. M. Biochem. Pharmacol. 1961, 7, 88–95.