Role of substituents in cyclodextrin derivatives for enantioselective gas chromatographic separation of chiral terpenoids in the essential oils of Mentha spicata

作者: VS Pragadheesh , Anju Yadav , Chandan Singh Chanotiya , None

DOI: 10.1016/J.JCHROMB.2015.07.034

关键词:

摘要: Enantioselective GC-FID and enantioselective GC-MS have been utilized under temperature gradient mode with differently substituted heptakis- octakis-cyclodextrins to achieve the resolution of chiral terpenoids in essential oil indigenously grown cultivars Mentha spicata. Modified cyclodextrins were derivatized GC column for separation terpenoids. A 2,3-diethyl-6-tert-butyldimethylsilyl-β-cyclodextrin doped into 14% cyanopropylphenyl/86%dimethylpolysiloxane (TBDE-β-CD) showed good enantioselectivity all studied compounds excluding carvone. Carvone enantiomers well resolved 2,3-diacetoxy-6-tert-butyldimethylsilyl-β-cyclodextrin (TBDA-β-CD) enantioseparation (Es) 1.006. TBDE-β-CD provides maximum enantiomeric β-pinene (Es 1.038), sabinene 1.051), limonene 1.045), isomenthone 1.029) α-terpineol 1.014). Furthermore, enantiomer elution order reversal was observed sabinene, menthone, terpinen-4-ol menthol while changing from β- γ-cyclodextrin phase. exhibits by substituents i.e., methyl acetyl at 2- & 3- position cyclodextrin derivative. Chiral constituents such as (+)-isomenthone, (-)-menthone, (1R,2S,5R)-(-)-menthol (4S)-(+)-piperitone exist a single >99% excess. Existence (R)-(+)-limonene (S)-(+)-carvone has proven first time M. spicata oils can be used marker Indian origin.

参考文章(29)
Carmen Barba, Rosa M. Martínez, Marta M. Calvo, Guillermo Santa-María, Marta Herraiz, Chiral analysis by online coupling of reversed-phase liquid chromatography to gas chromatography and mass spectrometry. Chirality. ,vol. 24, pp. 420- 426 ,(2012) , 10.1002/CHIR.22036
C DECARVALHO, M DAFONSECA, Carvone: Why and how should one bother to produce this terpene Food Chemistry. ,vol. 95, pp. 413- 422 ,(2006) , 10.1016/J.FOODCHEM.2005.01.003
Constantina P. Kapnissi-Christodoulou, Ioannis J. Stavrou, Maria C. Mavroudi, Chiral ionic liquids in chromatographic and electrophoretic separations. Journal of Chromatography A. ,vol. 1363, pp. 2- 10 ,(2014) , 10.1016/J.CHROMA.2014.05.059
Alessandro Giuffrida, Giuseppe Maccarrone, Vincenzo Cucinotta, Serena Orlandini, Annalinda Contino, Recent advances in chiral separation of amino acids using capillary electromigration techniques. Journal of Chromatography A. ,vol. 1363, pp. 41- 50 ,(2014) , 10.1016/J.CHROMA.2014.08.041
V.S. Pragadheesh, Arvind Saroj, Anju Yadav, C.S. Chanotiya, M. Alam, A. Samad, Chemical characterization and antifungal activity of Cinnamomum camphora essential oil Industrial Crops and Products. ,vol. 49, pp. 628- 633 ,(2013) , 10.1016/J.INDCROP.2013.06.023
Giuseppe Sicoli, Diana Kreidler, Harri Czesla, Henning Hopf, Volker Schurig, Gas chromatographic enantioseparation of unfunctionalized chiral alkanes: a challenge in separation science (overview, state of the art, and perspectives). Chirality. ,vol. 21, pp. 183- 198 ,(2009) , 10.1002/CHIR.20638
Valtcho D. Zheljazkov, Charles L. Cantrell, Tess Astatkie, Alex Hristov, Yield, content, and composition of peppermint and spearmints as a function of harvesting time and drying. Journal of Agricultural and Food Chemistry. ,vol. 58, pp. 11400- 11407 ,(2010) , 10.1021/JF1022077