Chemical Diversity of Volatiles of Teucrium orientale L. var. orientale, var. puberulens, and var. glabrescens Determined by Simultaneous GC‐FID and GC/MS Techniques

In the present work, three varieties of Teucrium orientale, var. orientale, var. puberulens, and var. glabrescens, were collected and investigated for chemical composition of the oils. Subsequent gas chromatography (GC‐FID) and gas chromatography coupled to mass spectrometry (GC/MS) revealed high abundance of sesquiterpenes in the essential oils analyzed. All the oils contained β‐caryophyllene (22.6, 8.5, and 6.3%, resp.) and hexadecanoic acid (7.9, 12.8, and 13.1%). Germacrene D (24.6 and 33.4%) and bicyclogermacrene (6.7 and 8.5%) were found to be the main constituents of var. orientale and var. puberulens, respectively. The high percentages of β‐cubebene (26.9%), α‐cubebene (9.0%), and α‐copaene (7.2%) established the diversity of var. glabrescens. The qualitative difference between the essential oils allowed the differentiation between the varieties in agreement with the morphological observations described in Flora of Turkey for each variety studied. In addition, a cluster analysis of twelve Teucrium taxa based on the essential‐oil composition has been carried out. Hovewer, the analysis did not clearly reflect the infrageneric classification of the genus, it largely confirmed the relationships between the infraspecific taxa of Teucrium orientale and T. chamaedrys.

[1]  A. Kandemir,et al.  Chemical Composition of the Essential Oil of Teucrium multicaule Montbret Et Aucher Ex Bentham from Turkey , 2010 .

[2]  Shabana I. Khan,et al.  Gas chromatographic-mass spectrometric analysis of volatiles obtained by four different techniques from Salvia rosifolia Sm., and evaluation for biological activity. , 2010, Journal of chromatography. A.

[3]  B. Demirci,et al.  Compositions of Essential Oils and Trichomes of Teucrium chamaedrys L. subsp. trapezunticum Rech. fil. and subsp. syspirense (C. Koch) Rech. fil. , 2009, Chemistry & biodiversity.

[4]  M. Khouja,et al.  Chemical composition and antimicrobial activity of essential oils of Cupressus arizonica Greene , 2007 .

[5]  M. Gordon,et al.  Light-induced off-flavor development in cloudy apple juice. , 2007, Journal of agricultural and food chemistry.

[6]  C. Quijano,et al.  Changes in volatile compounds of fermented cereza agria [Phyllanthus acidus (L.) Skeels] fruit , 2007 .

[7]  S. V. Dutra,et al.  Essential oil variation among Brazilian accessions of Salvia guaranitica L. , 2007 .

[8]  S. Rosselli,et al.  Chemical composition and antimicrobial activity of the essential oil from aerial parts of Micromeria fruticulosa (Bertol.) Grande (Lamiaceae) growing wild in Southern Italy , 2007 .

[9]  G. B. Oganesyan On a flavone from Teucrium orientale , 2007, Chemistry of Natural Compounds.

[10]  N. Fokialakis,et al.  Essential oil composition of Achillea lingulata and A. umbellata , 2007 .

[11]  H. Zarrouk,et al.  Composition of the essential oil of Teucrium ramosissimum Desf. (Lamiaceae) from Tunisia , 2007 .

[12]  D. Hadjipavlou-Litina,et al.  Composition and antioxidant activity of the essential oil of Teucrium royleanum Wall. ex Benth growing in Pakistan , 2007 .

[13]  R. Adams,et al.  Identification of Essential Oil Components By Gas Chromatography/Mass Spectrometry , 2007 .

[14]  F. Chemat,et al.  Rapid Extraction of Volatile Compounds Using a New Simultaneous Microwave Distillation: Solvent Extraction Device , 2007 .

[15]  M. Aouni,et al.  Chemical composition and in vitro antifungal and antioxidant activity of the essential oil and methanolic extract of Teucrium sauvagei Le Houerou , 2006, Natural product research.

[16]  A. Dönmez Teucrium chasmophyticum Rech. f. (Lamiaceae): A New Record for the Flora of Turkey , 2006 .

[17]  A. Pichette,et al.  The essential oil composition of devil's club, Oplopanax horridus J. E. Smith Miq. , 2006 .

[18]  P. Marin,et al.  Composition and antimicrobial activity of the essential oil of six Hypericum species from Serbia , 2006 .

[19]  M. Faleiro,et al.  Composition of the essential oils of Thymus and Origanum species from Algeria and their antioxidant and antimicrobial activities. , 2006, Journal of agricultural and food chemistry.

[20]  M. Rychlik,et al.  Character impact odorants of fennel fruits and fennel tea. , 2006, Journal of agricultural and food chemistry.

[21]  A. Yildirim,et al.  Antioxidant Activities of the Extracts and Components of Teucrium orientale L. var. orientale , 2006 .

[22]  F. Senatore,et al.  Chemical composition of the essential oil of Salvia microstegia Boiss. et Balansa growing wild in Lebanon. , 2006, Journal of chromatography. A.

[23]  M. Küçük,et al.  Chemical Composition and Antimicrobial Activities of the Essential Oils of Teucrium chamaedrys. subsp. chamaedrys., T. orientale. var. puberulens., and T. chamaedrys. subsp. lydium. , 2006 .

[24]  G. Lee,et al.  Determination of optimum conditions for the analysis of volatile components in pine needles by double-shot pyrolysis-gas chromatography-mass spectrometry. , 2005, Journal of chromatography. A.

[25]  M. Yatagai,et al.  Components of the essential oils of Azadirachta indica A. Juss, Azadirachta siamensis Velton, and Azadirachta excelsa (Jack) Jacobs and their comparison , 2005, Journal of Wood Science.

[26]  Francesco Epifano,et al.  Chemical composition, antimicrobial and antioxidant activity of the essential oil of Teucrium marum (Lamiaceae). , 2005, Journal of ethnopharmacology.

[27]  Y. Ueda,et al.  Volatile components of tea-scented modern roses and ancient Chinese roses , 2005 .

[28]  M. Simmonds,et al.  Neoclerodanes from Teucrium orientale. , 2004, Chemical & pharmaceutical bulletin.

[29]  F. Senatore,et al.  Chemical composition of the essential oil of Salvia multicaulis Vahl. var. simplicifolia Boiss. growing wild in Lebanon. , 2004, Journal of chromatography. A.

[30]  M. Alaiz,et al.  Amino acids composition of Teucrium nutlet proteins and their systematic significance. , 2004, Annals of botany.

[31]  M. Yalçın,et al.  The variation of antioxidant activities and chemical composition of essential oils of Teucrium orientale L. var. orientale during harvesting stages , 2004 .

[32]  A. El-Shazly,et al.  Chemical analysis and biological activities of the essential oil of Teucrium leucocladum Boiss. (Lamiaceae) , 2004 .

[33]  L. Salgueiro,et al.  Micromorphology of trichomes and composition of essential oil of Teucrium capitatum , 2004 .

[34]  Ana C. Soria,et al.  Characterization of artisanal honeys from Madrid (Central Spain) on the basis of their melissopalynological, physicochemical and volatile composition data , 2004 .

[35]  M. Abdollahi,et al.  Stimulation by theophylline and sildenafil of rat submandibular secretion of protein, epidermal growth factor and flow rate. , 2003, Pharmacological research.

[36]  M. Abdollahi,et al.  Antinociceptive effects of Teucrium polium L total extract and essential oil in mouse writhing test. , 2003, Pharmacological research.

[37]  R. Miri,et al.  Composition of the Essential Oil of Teucrium orientate L. ssp. orientate from Iran , 2003 .

[38]  L. Salgueiro,et al.  Composition of the essential oil and micromorphology of trichomes of Teucrium salviastrum, an endemic species from Portugal , 2002 .

[39]  C. Cid,et al.  Profiles of volatile compounds and sensory analysis of three blends of coffee: influence of different proportions of Arabica and Robusta and influence of roasting coffee with sugar , 2002 .

[40]  Masayoshi Sawamura,et al.  Volatile constituents of Vietnamese pummelo, orange, tangerine and lime peel oils , 2002 .

[41]  K. Başer Aromatic biodiversity among the flowering plant taxa of Turkey , 2002 .

[42]  M. Miyazawa,et al.  Comparison of the essential oils of Glehnia littoralis from Northern and Southern Japan. , 2001, Journal of agricultural and food chemistry.

[43]  E. Dellacassa,et al.  Essential oil of Baccharis uncinella DC. from Southern Brazil , 2001 .

[44]  M. Choudhary,et al.  Essential oil constituents of the spice Cinnamomum tamala (Ham.) Nees & Eberm. , 2000 .

[45]  T. Shibamoto,et al.  Volatile chemicals identified in extracts from leaves of Japanese mugwort (Artemisia princeps pamp.). , 2000, Journal of agricultural and food chemistry.

[46]  K. Korány,et al.  Preliminary results of a recognition method visualizing the aroma and fragrance features , 2000 .

[47]  D. B. Hibbert,et al.  USE OF GAS CHROMATOGRAMS OF ESSENTIAL LEAF OILS TO COMPARE EIGHT TAXA OF GENUS ANGOPHORA (MYRTACEAE) : POSSIBLE RELATIONSHIPS TO THE GENUS EUCALYPTUS , 1999 .

[48]  H. Masuda,et al.  Identification of potent odorants in Japanese green tea (Sen-cha). , 1999, Journal of agricultural and food chemistry.

[49]  G. Buchbauer,et al.  Chemical composition of essential oils of Lantana camara leaves and flowers from Cameroon and Madagascar , 1999 .

[50]  O. Ekundayo,et al.  Essential oil constituents of Aframomum melegueta (Roscoe) K. Schum. seeds (alligator pepper) from Nigeria , 1999 .

[51]  C. Duque,et al.  Studies on the Aroma of Piñuela Fruit Pulp (Bromelia plumieri): Free and Bound Volatile Composition and Characterization of Some Glucoconjugates as Aroma Precursors , 1998 .

[52]  V. Sinnwell,et al.  The essential oil composition of fruits from smyrnium perfoliatum , 1998 .

[53]  C. Olsen,et al.  Aroma changes during black currant (Ribes nigrum L.) nectar processing , 1998 .

[54]  K. Başer,et al.  Composition of the Essential Oils of Three Teucrium Species from Turkey , 1997 .

[55]  M. Y. Combariza,et al.  Volatile secondary metabolites from Spilanthes americana obtained by simultaneous steam distillation-solvent extraction and supercritical fluid extraction , 1996 .

[56]  L. Mondello,et al.  Interactive use of linear retention indices, on polar and apolar columns, with a ms-library for reliable identification of complex mixtures , 1995 .

[57]  S. Nelson,et al.  Hepatotoxicity of germander (Teucrium chamaedrys L.) and one of its constituent neoclerodane diterpenes teucrin A in the mouse. , 1994, Chemical research in toxicology.

[58]  C. Duque,et al.  Volatile constituents of lulo (Solanum vestissimum D.) fruit , 1991 .

[59]  N. Davies,et al.  Gas chromatographic quality control for oil of Melaleuca terpinen-4-ol type (Australian tea tree) , 1989 .

[60]  F. Hammouda,et al.  Iridoids and Flavonoids of Teucrium polium Herb1 , 1986 .

[61]  Y. Nagao,et al.  Antitumor activity of Rabdosia and Teucrium diterpenoids against P 388 lymphocytic leukemia in mice. , 1982, Chemical & pharmaceutical bulletin.

[62]  R. Barneby,et al.  Flora of Turkey and the East Aegean Islands. , 1966 .

[63]  M. Yüksel,et al.  A Ph.D. Thesis , 2014 .

[64]  S. Buxaderas,et al.  Comparative study of different extraction techniques for the analysis of virgin olive oil aroma , 2007 .

[65]  J. Casanova,et al.  Chemical variability of Conyza sumatrensis and Microglossa pyrifolia from Côte d'Ivoire , 2007 .

[66]  J. Rohloff,et al.  Volatile constituents of the roots of Echinops kebericho mesfin , 2007 .

[67]  L. Chekir‐Ghedira,et al.  Chemical composition and antimicrobial activity of essential oils from Tunisian Pituranthos tortuosus (Coss.) Maire , 2006 .

[68]  Q. Su,et al.  Comparative analysis of clary sage (S. sclarea L.) oil volatiles by GC-FTIR and GC-MS , 2006 .

[69]  B. Demirci,et al.  The essential oil of Stachys laetivirens Kotschy & Boiss. ex Rech. fil., endemic in Turkey , 2005 .

[70]  Elizabeth Murillo,et al.  Essential oil composition from twelve varieties of basil (Ocimum spp) grown in Colombia , 2003 .

[71]  A. Ulubelen,et al.  Chemical and biological evaluation of genus teucrium , 2000 .

[72]  B. Demirci,et al.  Composition of the Essential Oil of Teucrium antitauricum T.Ekim , 1999 .

[73]  R. Ciriminna,et al.  Volatile Constituents of Teucrium polium L. from Turkey , 1998 .

[74]  S. Ley,et al.  The antifeedant activity of clerodane diterpenoids from Teucrium , 1989 .

[75]  P. Sandra,et al.  Capillary gas chromatography in essential oil analysis , 1987 .

[76]  L. Boulos Medicinal plants of North Africa , 1983 .

[77]  E. Kováts,et al.  Gas‐chromatographische Charakterisierung organischer Verbindungen. Teil 1: Retentionsindices aliphatischer Halogenide, Alkohole, Aldehyde und Ketone , 1958 .