Sesquiterpene hydrocarbons of the essential oil of Actinolema macrolema Boiss

The essential oils of Actinolema macrolema Boiss. (Apiaceae) were obtained by hydrodistillation in the first 3 (sample A) and the following 3 h (sample B) from crushed fruits and dried leaves (sample C), which were subsequently analyzed by GC and GC-MS. Overall, 64 components were characterized, representing 93% of the leaf oil. Thirty components were characterized from the fruit oil representing 95% of the first fraction and 90% of the second fraction consecutively. Guaia-5,7(11)-diene, selina-3,7(11)-diene, and juniper camphor were isolated from the oils by column chromatography and their structures were elucidated by GC-MS, 1H NMR, and 13C NMR. The occurrence of guaia-5,7(11)-diene in nature is reported for the first time. Guaia-5,7(11)-diene (37% and 30%), germacrene-B (25% and 21%), and selina-3,7(11)-diene (both 12%) were found as major components in the oil of sample A and the following sample B, respectively. In sample C, 1-octadecanol (24%) and hexadecanoic acid (19%) were identified as the major components. Additionally, antimicrobial activities of the fruit oils were determined using broth microdilution. Sample A exhibited relatively good inhibition of Staphylococcus epidermidis (MIC 62.5 m g/mL). The 2 fruit essential oils showed inhibitory (MIC 125 m g/mL) effects equal to those of the standard antifungal agent used against C. albicans.

Sesquiterpene hydrocarbons of the essential oil of Actinolema macrolema Boiss

The essential oils of Actinolema macrolema Boiss. (Apiaceae) were obtained by hydrodistillation in the first 3 (sample A) and the following 3 h (sample B) from crushed fruits and dried leaves (sample C), which were subsequently analyzed by GC and GC-MS. Overall, 64 components were characterized, representing 93% of the leaf oil. Thirty components were characterized from the fruit oil representing 95% of the first fraction and 90% of the second fraction consecutively. Guaia-5,7(11)-diene, selina-3,7(11)-diene, and juniper camphor were isolated from the oils by column chromatography and their structures were elucidated by GC-MS, 1H NMR, and 13C NMR. The occurrence of guaia-5,7(11)-diene in nature is reported for the first time. Guaia-5,7(11)-diene (37% and 30%), germacrene-B (25% and 21%), and selina-3,7(11)-diene (both 12%) were found as major components in the oil of sample A and the following sample B, respectively. In sample C, 1-octadecanol (24%) and hexadecanoic acid (19%) were identified as the major components. Additionally, antimicrobial activities of the fruit oils were determined using broth microdilution. Sample A exhibited relatively good inhibition of Staphylococcus epidermidis (MIC 62.5 m g/mL). The 2 fruit essential oils showed inhibitory (MIC 125 m g/mL) effects equal to those of the standard antifungal agent used against C. albicans.

___

  • Davis, P. H. In: Flora of Turkey and the East Aegean Islands, Vol. 4; Davis P. H., Ed.; University Press, Edinburgh, 19 Kleiman, R.; Spencer, G. F. Journal of American Oil Chemists’ Society 1982, 59, 29.
  • Barclay, A. S.; Earle, F. R. Economic Botany 1974, 28, 178–236.
  • Council of Europe; European Pharmacopoeia, Vol. 1; 5th Ed.; Strasbourg, 2005.
  • McLafferty, F. W.; Stauffer, D. B. The Wiley/NBS Registry of Mass Spectral Data, J Wiley and Sons, New York, 19 K¨ onig, W. A.; Joulain, D.; Hochmuth, D. H. Terpenoids and Related Constituents of Essential Oils. Library of MassFinder 3, Hamburg, Germany, 2004.
  • Ba¸ser, K. H. C.; Demirci, F. Chemistry of Essential Oils, In: Flavours and Fragrances: Chemistry, Bioprocessing and Sustainability, Berger; R. G.; Ed. Springer, Berlin, 2007.
  • Jennings, W. G.; Shibamoto, T. Quantitative Analysis of Flavor and Fragrance Volatiles by Glass Capillary GC, Academic Press, New York, 1980.
  • Joulain, D.; K¨ onig, W. A. The Atlas of Spectra Data of Sesquiterpene Hydrocarbons. EB-Verlag, Hamburg, 1998. ESO 2000. The Complete Database of Essential Oils. Boelens Aroma Chemical Information Service, The Netherlands, 1999.
  • Koneman, E. W.; Allen, S. D.; Janda, W. M.; Schreckenberger, P. C.; Winn, W. C. Color Atlas and Textbook of Diagnostic Microbiology. Lippincott-Raven, Philadelphia, PA, 1997.
  • ˙I¸scan, G.; Kırımer, N.; K¨urk¸c¨uo˘glu, M.; Ba¸ser, K. H. C.; Demirci, F.; J. Agric. Food Chem. 2002, 50, 394–3946. R¨ ucker, G.; Hefendehl, F. W. Phytochem. 1978, 17, 809–810.
  • Ferreira, M. J. P.; Oliveira, F. C.; Rodrigues, G. V.; Emerenciano, V. P. Internet Electronic Journal of Molecular Design 2004, 3, 737–749.
  • Beek, T. A. V.; Kleis, R.; Posthumus, M. A.; Veldhuizen, A. V. Phytochem. 1989, 28, 1909–1911.
  • Joulain, D.; K¨ onig, W. A. Selina-3, 7(11)-dien. In: The Atlas of Spectral Data of Sesquiterpene Hydrocarbons, E.B. Verlag, Hamburg, 1998.
  • Bakhtiar, A.; Sargent, M. V.; Skelton, B. W.; White, A. H. Acta Crystallographica C 2004, 60, 503–504.
  • Zhao, Y.; Yue, J.; Lin, Z.; Ding, J.; Sun, H. Phytochem. 1997, 44, 459–464.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

N-functionalized benzimidazol-2-ylidene silver complexes: synthesis, characterization, and antimicrobial studies

Yetkin GÖK, Senem AKKOÇ, Özlem Özeroğlu ÇELİKAL, İlknur ÖZDEMİR, Selami GÜNAL, Elif SAYIN

Synthesis of tetrakis(carboxyphenyl)porphyrin coated paramagnetic iron oxide nanoparticles via amino acid for photodegradation of methylene blue

Rahmatolah RAHIMI, Azadeh TADJARODI, Mina IMANI, Mahboubeh RABBANI, Samaneh Safalou MOGHADDAM, Hamed KERDARI

Synthesis, characterization, and DFT calculation of a Pd(II) Schiff base complex

Alireza AKBARI, Zahra ALINIA

Comparative study of microwave-assisted and conventional synthesis of ibuprofen-based acyl hydrazone derivatives

Ayşe Uzgören BARAN

Sesquiterpene hydrocarbons of the essential oil of Actinolema macrolema Boiss

Betül DEMİRCİ, Gülden Koltuksuz YASDIKCIOĞLU, Kemal Hüsnü Can BAŞER

Synthesis of new N-[3-(Benzo[d]thiazol-2-yl)-4-methylthiazol-2(3H)-ylidene] substituted benzamides

Aamer SAEED, Hummera RAFIQUE

Asymmetric Henry reaction catalyzed by Cu(I)-based chiral amino alcohol complex

Tianhua SHEN, Quan QIN, Hang NI, Ting XIA, Xiaocong ZHOU, Funa CUI, Junqi LI, Deqiang RAN, Qingbao SONG

Synthesis, characterization, and biological activity of coordination polymers derived from pyromellitic dianhydride

Yogesh Shantilal PATEL, Ritu Bharat DIXIT, Hasmukh Shanubhai PATEL

Electrochemical determination of Sudan IV in food samples by using graphene-modified glassy carbon electrodes

Meifeng CHEN, Xinying MA, Xia LI

Synthesis, characterization, and luminescence of zinc(II) and cadmium(II) coordination complexes: [Zn(phen)2(CH3COO)](ClO4), [Zn(bpy)2(ClO4)](ClO4), and [Cd(phen)2(NO3)2]

İbrahim KANİ, Mehmet KURTÇA