Chemical Composition of Essential Oil from Italian Populations of Artemisia alba Turra (Asteraceae)
Abstract
:1. Introduction
2. Results and Discussion
Kia | Kib | Component | Ident. | A | B | C | D |
---|---|---|---|---|---|---|---|
Monoterpene Hydrocarbons | |||||||
909 | 1032 | Santolina triene | 1, 2 | 7.3 | 1.2 | ||
931 | 1023 | α-Thujene | 1, 2 | 0.1 | |||
938 | 1032 | α-Pinene | 1, 2, 3 | 1.7 | 0.3 | ||
953 | 1076 | Camphene | 1, 2 | 1.2 | 0.1 | ||
973 | 1132 | Sabinene | 1, 2 | 0.6 | |||
980 | 1118 | β-Pinene | 1, 2, 3 | 0.5 | 2.7 | 0.3 | |
1025 | 1278 | p-Cymene | 1, 2, 3 | 0.5 | 0.2 | ||
1030 | 1203 | Limonene | 1, 2, 3 | 1.0 | |||
1057 | 1256 | γ-Terpinene | 1, 2, 3 | 0.2 | |||
1114 | 1408 | 1,3,8-p-Menthatriene | 1, 2 | 0.1 | |||
Total | 11.3 | 5.8 | 0.9 | - | |||
Oxygenated Monoterpenes | |||||||
1024 | 1402 | Santolina alcohol | 1, 2 | 2.6 | 0.2 | ||
1034 | 1213 | 1,8-Cineole | 1, 2, 3 | 1.6 | 0.7 | 0.1 | |
1063 | 1555 | cis-Sabinene hydrate | 1, 2 | 0.2 | 0.2 | ||
1063 | 1358 | Artemisia ketone | 1, 2 | 4.6 | |||
1085 | 1512 | Artemisia alcohol | 1, 2 | 6.0 | |||
1093 | 1474 | trans-Sabinene hydrate | 1, 2 | 1.1 | 0.3 | t | |
1098 | 1553 | Linalool | 1, 2, 3 | 0.6 | 0.1 | ||
1108 | 1616 | Hotrienol | 3.3 | ||||
1115 | 1451 | β-Thujone | 1, 2 | 0.7 | |||
1117 | 1571 | trans-p-Menth-2-en-1-ol | 1, 2 | 0.3 | |||
1125 | 1540 | Chrysanthenone | 1, 2 | 1.1 | 3.1 | ||
1128 | 1487 | α-Campholenal | 1, 2 | 0.2 | |||
1138 | 1664 | trans-Pinocarveol | 1, 2 | 0.1 | |||
1145 | 1532 | Camphor | 1, 2, 3 | 1.6 | 3.4 | 0.7 | |
1146 | Neolyratol | 1, 2 | 0.3 | ||||
1149 | 1685 | trans-Verbenol | 1, 2 | 0.2 | 1.8 | ||
1164 | 1684 | trans-Chrysanthenol | 1, 2 | 0.4 | |||
1165 | 1587 | Pinocarvone | 1, 2 | 1.6 | |||
1167 | 1719 | Borneol | 1, 2, 3 | 2.1 | 9.3 | 0.7 | |
1174 | 1565 | cis-Pinocamphone | 1, 2 | 14.9 | 1.1 | ||
1176 | 1611 | Terpinen-4-ol | 1, 2, 3 | 1.5 | 0.6 | 1.2 | |
1183 | 1757 | cis-Piperitol | 1, 2 | 0.2 | |||
1185 | 1856 | p-Cymen-8-ol | 1, 2 | 0.3 | 0.1 | ||
1189 | 1706 | α-Terpineol | 1, 2, 3 | 0.5 | 1.2 | 0.7 | |
1193 | 1648 | Myrtenal | 1, 2 | 0.7 | 0.2 | ||
1197 | 1805 | Myrtenol | 1, 2 | 0.6 | 1.2 | 1.4 | 0.5 |
1201 | 1618 | Safranal | 1, 2 | 0.1 | |||
1217 | 1845 | trans-Carveol | 1, 2 | 0.5 | 1.6 | 0.5 | |
1226 | 1878 | cis-Carveol | 1, 2 | 0.7 | 0.3 | 0.4 | |
1238 | 1694 | Neral | 1, 2 | 0.4 | |||
1241 | 1752 | Carvone | 1, 2 | 0.2 | 0.4 | ||
1268 | 1741 | Geranial | 1, 2 | 0.3 | |||
1293 | 2198 | Thymol | 1, 2, 3 | 0.4 | |||
1299 | 2239 | Carvacrol | 1, 2, 3 | 0.1 | |||
1343 | 1748 | Piperitone | 1, 2 | 2.2 | 12.6 | 32.8 | |
Total | 12.8 | 37.5 | 37.7 | 41.6 | |||
Sesquiterpene Hydrocarbons | |||||||
1352 | 1466 | α-Cubebene | 1, 2 | 0.2 | |||
1377 | 1497 | α-Copaene | 1, 2 | 0.3 | |||
1385 | 1535 | β-Bourbonene | 1, 2 | 0.3 | 0.1 | ||
1387 | 1594 | β-Elemene | 1, 2 | 1.0 | 0.4 | 0.4 | |
1415 | 1612 | β-Caryophyllene | 1, 2, 3 | 0.9 | 0.3 | 0.6 | |
1437 | 1530 | α-Guaiene | 1, 2 | 0.2 | |||
1453 | 1673 | (E)-β-Farnesene | 1, 2 | 1.2 | |||
1455 | 1689 | α-Humulene | 1, 2 | 1.3 | 0.2 | t | |
1463 | 1667 | allo-Aromadendrene | 1, 2 | 0.9 | 0.5 | ||
1474 | 1682 | γ-Gurjunene | 1, 2 | 6.4 | 1.0 | ||
1477 | 1726 | Germacrene D | 1, 2 | 2.1 | 4.9 | 10.2 | |
1478 | 1704 | γ-Muurolene | 1, 2 | 0.6 | |||
1482 | 1741 | β-Eudesmene (β-Selinene) | 1, 2 | 0.3 | |||
1486 | 1733 | α-Selinene | 1, 2 | 7.6 | 0.5 | ||
1487 | 1679 | α-Amorphene | 1, 2 | 0.4 | |||
1489 | 1729 | (Z,E)-α-Farnesene | 1, 2 | 2.7 | |||
1490 | 1694 | β-Guaiene | 1, 2 | 0.2 | 0.3 | ||
1491 | 1756 | Bicyclogermacrene | 1, 2 | 2.5 | |||
1506 | 1760 | (E,E)-α-Farnesene | 1, 2 | 1.5 | |||
1509 | 1746 | cis-(Z)-α-Bisabolene | 1, 2 | 0.8 | 2.7 | ||
1510 | 1743 | β-Bisabolene | 1, 2 | 0.6 | |||
1515 | 1776 | γ-Cadinene | 1, 2 | 0.5 | |||
1520 | 1839 | 1-S-cis-Calamenene | 1, 2 | 0.1 | |||
1526 | 1773 | δ-Cadinene | 1, 2 | 1.5 | 0.4 | 0.3 | 0.4 |
1554 | 1856 | Germacrene B | 1, 2 | 0.3 | |||
Total | 15.7 | 21.0 | 7.8 | 13.1 | |||
Oxygenated Sesquiterpenes | |||||||
1234 | 1641 | nor-Davanone | 1, 2 | 0.1 | |||
1457 | 1712 | Cabreuva oxide B | 1, 2 | 0.9 | |||
1476 | Davana ether | 1, 2 | 0.3 | ||||
1534 | 1991 | Artedouglasia oxide A | 1, 2 | 0.9 | |||
1559 | 1967 | Davanone B | 1, 2 | 0.8 | |||
1563 | 2065 | Artedouglasia oxide D | 1, 2 | 0.6 | |||
1564 | 2050 | (E)-Nerolidol | 1, 2 | 0.6 | 6.4 | ||
1564 | 2056 | Ledol | 1, 2 | 0.2 | |||
1578 | 2150 | Spathulenol | 1, 2, 3 | 1.6 | 4.2 | 0.4 | 2.1 |
1580 | 2008 | Caryophyllene oxide | 1, 2, 3 | 1.8 | 1.1 | 2.0 | |
1587 | 2108 | Dihydronerolidol | 1,2 | 2.9 | |||
1588 | 2025 | Davanone D | 1, 2 | 10.5 | |||
1591 | 2104 | Viridiflorol | 1, 2 | 0.4 | |||
1598 | 2107 | Guaiol | 1, 2 | 2.8 | |||
1638 | 2223 | Isospathulenol | 1, 2 | 0.7 | 0.1 | ||
1640 | 2185 | T-Cadinol | 1, 2 | 2.8 | |||
1641 | 2209 | T-Muurolol | 1, 2 | 0.9 | |||
1648 | 2399 | Aromadendrene oxide | 1, 2 | 1.0 | |||
1653 | 2252 | α-Eudesmol | 1, 2 | 42.2 | |||
1655 | a C15H22O | 1, 2 | 1.1 | ||||
1657 | 2217 | α-Bisabolone oxide A | 1, 2 | 16.4 | |||
1658 | 2156 | α-Bisabolol oxide B | 1, 2 | 2.2 | |||
1675 | 2213 | (Z)-α-Bisabolene epoxide | 1, 2 | 0.5 | |||
1682 | 2246 | Bisabolone oxide | 1, 2 | 9.0 | |||
1682 | 2232 | α-Bisabolol | 1, 2 | 0.8 | 1.7 | 4.5 | |
1687 | 1896 | allo-Aromadendrene oxide | 1, 2 | 0.4 | 0.2 | 0.8 | |
1689 | 2359 | 8-Cedren-13-ol | 1, 2 | 10.3 | |||
1692 | 2342 | (2Z,6E)-Farnesol | 1, 2 | 1.9 | |||
1692 | 2245 | epi-α-Bisabolol | 1, 2 | 0.8 | 4.7 | ||
1738 | 2162 | α-Bisabolol oxide A | 1, 2 | 1.4 | |||
1765 | 2518 | cis-Lanceol | 1, 2 | 0.4 | 0.2 | ||
Total | 47.0 | 23.2 | 44.5 | 30.9 | |||
Others | |||||||
977 | 1452 | 1-Octen-3-ol | 1, 2 | 0.2 | |||
1123 | 1570 | Isophorone | 1, 2 | t | |||
1206 | 1510 | Decanal | 1, 2 | 0.2 | |||
1397 | 1959 | cis-Jasmone | 1, 2 | 0.1 | |||
1405 | 2031 | Methyleugenol | 1, 2 | 0.6 | 0.3 | ||
Total | 0.7 | 0.5 | 0.2 | - | |||
Esters | |||||||
1235 | 1583 | trans-Chrysanthenyl acetate | 1, 2 | 1.4 | 2.1 | 1.6 | |
1241 | Linalyl formate | 1, 2 | 0.1 | ||||
1264 | 1561 | cis-Chrysanthenyl acetate | 1, 2 | 0.6 | t | 1.5 | |
1286 | 1567 | Bornyl acetate | 1, 2, 3 | 0.5 | 0.2 | ||
1325 | 1678 | Myrtenyl acetate | 1, 2 | 0.3 | |||
1362 | 1729 | Neryl acetate | 1, 2 | 0.5 | |||
1818 | 1716 | (2Z,6E)-Farnesyl acetate | 1, 2 | t | |||
Total | 2.5 | 2.2 | 0.5 | 3.6 | |||
Oxygenated diterpenes | |||||||
2135 | 2625 | (E)-Phytol | 1, 2 | 1.1 | |||
Total compounds | 47 | 57 | 41 | 38 | |||
TOTAL | 90.0 | 90.2 | 91.6 | 90.3 |
3. Experimental
3.1. Plant Material
3.2. Isolation of the Essential Oil
3.3. Gas Chromatography-Mass Spectrometry
3.4. Identification of Components
4. Conclusions
Acknowledgments
References
- Oberprieler, C.; Himmelreich, S.; Vogt, R. A new subtribal classification of the tribe Anthemideae (Compositae). Willdenowia 2007, 37, 89–114. [Google Scholar]
- Bremer, K.; Humphries, C.J. Generic monograph of the Asteraceae-Anthemideae. Bull. Nat. His. Mus. 1993, 23, 71–177. [Google Scholar]
- Ling, Y.R. The genera Artemisia L. and Seriphidium (Bess.) Poljak. in the world. Compositae Newsl. 1994, 25, 39–45. [Google Scholar]
- McArthur, E.D.; Plummer, A.P. Biogeography and management of native Western shrubs: A case study, section Tridentatae of Artemisia. Great Basin Nat. Mem. 1978, 2, 229–243. [Google Scholar]
- Valles, J.; Torrell, M.; Garnatje, T.; Garcia-Jacas, N.; Vilatersana, R.; Susanna, A. The genus Artemisia and its allies: Phylogeny of the subtribe Artemisiinae (Asteraceae, Anthemideae) based on nucleotide sequences of nuclear ribosomal DNA internal transcribed spacers (ITS). Plant Biol. 2003, 5, 274–284. [Google Scholar] [CrossRef]
- Tutin, T.G.; Persson, K.; Guttermann, W.; Artemisia, L. Flora Europaea; Tutin, T.G., Heywood, V.H., Burges, N.A., Valentine, D.H., Walters, S.M., Webb, D.A., Eds.; Cambridge University Press: Cambridge, UK, 1976; Volume 4, pp. 178–186. [Google Scholar]
- Besser, W.S. Synopsis Absinthiorum. Bull. Soc. Imp. Natl. Mosc. 1829, 1, 219–265. [Google Scholar]
- Pignatti, S. Flora d’Italia; Edagricole: Bologna, Italy, 1982; Volume 3, p. 107. [Google Scholar]
- Fiori, A. Nuova Flora Analitica d’Italia; Ricci: Firenze, Italy, 1927; Volume 2, pp. 631–639. [Google Scholar]
- Greger, H.; Haslinger, E.; Hofer, O. Naturally occurring sesquiterpene-coumarin ethers. Part 2. Albartin, a new sesquiterpene-coumarin ether from Artemisia alba. Monatsh. Chem. 1982, 113, 375–379. [Google Scholar] [CrossRef]
- Lojacono Pojero, M. Flora sicula, o Descrizione Delle Piante Vascolari Spontanee o Indigenate in Sicilia; Tip. Boccone Del Povero: Palermo, Italy, 1903; Volume 2, p. 72. [Google Scholar]
- Tan, R.X.; Zheng, W.F.; Tang, H.Q. Biologically active substances from the genus Artemisia. Planta Med. 1998, 64, 295–302. [Google Scholar] [CrossRef]
- Bora, K.S.; Sharma, A. Evaluation of antioxidant and free-radical scavenging potential of Artemisia absinthium. Pharm. Biol. 2011, 49, 101–109. [Google Scholar] [CrossRef]
- Gorunovic, M.S.; Bogavac, P.M.; Chalchat, J.C.; Garry, R.P. Analysis of the essential oil of Artemisia lobelii All. Pharmazie 1992, 47, 803–804. [Google Scholar]
- Stojanovic, G.; Palic, R.; Mitrovic, J.; Djokovic, D. Chemical composition and antimicrobial activity of the essential oil of Artemisia lobelii All. J. Essent. Oil Res. 2000, 12, 621–624. [Google Scholar]
- Blagojevic, P.D.; Jovanovic, M.M.; Palic, R.M.; Stojanovic, G.S. Changes in the volatile profile of the Artemisia lobelii All. during prolonged plant material storage. J. Essent. Oil Res. 2009, 21, 497–500. [Google Scholar] [CrossRef]
- Flora Europaea Search Results Home Page. Available online: http://rbg-web2.rbge.org.uk/cgi-bin/nph-readbtree.pl/feout?FAMILY_XREF=&GENUS_XREF=Artemisia&SPECIES_XREF=&TAXON_NAME_XREF=&RANK= (accessed on 31 July 2012).
- Janot, M.M.; Gautier, J. Some Artemisia species from Persia and their santonine content. Bull. Sci. Pharmacol. 1935, 42, 404–408. [Google Scholar]
- Appendino, G.; Gariboldi, P.; Menichini, F. Oxygenated nerolidol derivatives from Artemisia alba. Phytochemistry 1985, 24, 1729–1733. [Google Scholar]
- Peruzzi, L.; Gargano, D.; Cesca, G. Karyological observations on Artemisia alba Turra (Asteraceae). Caryologia 2005, 58, 78–82. [Google Scholar]
- Maggio, A.; Rosselli, S.; Brancazio, C.L.; Safder, M.; Spadaro, V.; Bruno, M. Artalbic acid, a sesquiterpene with an unusual skeleton from Artemisia alba (Asteraceae) from Sicily. Tetrahedron Lett. 2011, 52, 4543–4545. [Google Scholar]
- Raimondo, F.M.; Rossitto, M.; Ottonello, D. Numeri cromosomici per la flora Italiana: 967–976. Inform. Bot. Ital. 1984, 15, 58–65. [Google Scholar]
- Mucciarelli, M.; Caramiello, R.; Maffei, M. Essential oils from some Artemisia species growing spontaneously in north-west Italy. Flav. Frag. J. 1995, 10, 25–32. [Google Scholar] [CrossRef]
- Ronse, A.C.; De Pooter, H.L. Essential oil production by Belgian Artemisia alba (Turra) before and after micropropagation. J. Essent. Oil Res. 1990, 2, 237. [Google Scholar] [CrossRef]
- Radulovic, N.; Blagojevic, P. Volatile profiles of Artemisia alba from contrasting serpentine and calcareous habitats. Nat. Prod. Commun. 2010, 5, 1117–1122. [Google Scholar]
- Council of Europe, European Pharmacopoeia, 5th ed; Council of Europe: Strasbourg Cedex, France, 2004; Volume I, pp. 217–218.
- Davies, N.W. Gas Chromatographic retention indexes of monoterpenes and sesquiterpenes on methyl silicone and Carbowax 20M phases. J. Chromatogr. A 1990, 503, 1–24. [Google Scholar]
- Jennings, W.; Shibamoto, T. Qualitative Analysis of Flavour and Fragrance Volatiles by Glass Capillary Gas Chromatography; Academic Press: New York, NY, USA, 1980. [Google Scholar]
- Adams, R.P. Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry, 4th ed; Allured Publishing Co.: Carol Stream, IL, USA, 2007. [Google Scholar]
- Sample Availability: Samples of the oils are available from the authors.
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Maggio, A.; Rosselli, S.; Bruno, M.; Spadaro, V.; Raimondo, F.M.; Senatore, F. Chemical Composition of Essential Oil from Italian Populations of Artemisia alba Turra (Asteraceae). Molecules 2012, 17, 10232-10241. https://doi.org/10.3390/molecules170910232
Maggio A, Rosselli S, Bruno M, Spadaro V, Raimondo FM, Senatore F. Chemical Composition of Essential Oil from Italian Populations of Artemisia alba Turra (Asteraceae). Molecules. 2012; 17(9):10232-10241. https://doi.org/10.3390/molecules170910232
Chicago/Turabian StyleMaggio, Antonella, Sergio Rosselli, Maurizio Bruno, Vivienne Spadaro, Francesco Maria Raimondo, and Felice Senatore. 2012. "Chemical Composition of Essential Oil from Italian Populations of Artemisia alba Turra (Asteraceae)" Molecules 17, no. 9: 10232-10241. https://doi.org/10.3390/molecules170910232