Isolation of sesquiterpenoids from Matricaria chamomilla by means of solvent assisted flavor evaporation and centrifugal partition chromatography.
Bioactivity
Countercurrent chromatography
Enrichment
Natural product
Purification
Sesquiterpenes
Journal
Analytical and bioanalytical chemistry
ISSN: 1618-2650
Titre abrégé: Anal Bioanal Chem
Pays: Germany
ID NLM: 101134327
Informations de publication
Date de publication:
Jul 2021
Jul 2021
Historique:
received:
18
03
2021
accepted:
07
05
2021
revised:
26
04
2021
pubmed:
30
5
2021
medline:
11
9
2021
entrez:
29
5
2021
Statut:
ppublish
Résumé
The (semi)volatile fraction of Matricaria chamomilla L., an annual herbal plant from the family of Asteraceae, contains high quantities of sesquiterpenes and sesquiterpenoids. A method was developed to achieve isolation and separation of these compounds, using a combination of solvent assisted flavor evaporation (SAFE) and solid support-free liquid-liquid chromatography. The biphasic liquid solvent system n-heptane/ethyl acetate/methanol/water, 5/2/5/2 v/v/v/v (Arizona S) was elaborated as a suitable solvent system for the simultaneous separation of the target compounds. The lab-scale liquid-liquid chromatography separation performed in a countercurrent chromatography (CCC) column was successfully transferred to a semi-preparative centrifugal partition chromatography (CPC) column, which enabled the isolation of artemisia ketone, artemisia alcohol, α-bisabolone oxide A, and (E)-en-yn-dicycloether. α-Bisabolol oxide A and (Z)-en-yn-dicycloether co-eluted, but were successfully separated by subsequent size-exclusion chromatography (SEC). Similarly, spathulenol and α-bisabolol oxide B were obtained as a mixture, and were separated by means of column chromatography using silica gel as stationary phase. The isolated compounds were characterized by means of nuclear magnetic resonance spectroscopy (NMR) and gas chromatography-mass spectrometry (GC-MS).
Identifiants
pubmed: 34050388
doi: 10.1007/s00216-021-03400-w
pii: 10.1007/s00216-021-03400-w
pmc: PMC8245379
doi:
Substances chimiques
Plant Extracts
0
Sesquiterpenes
0
Solvents
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
4387-4396Subventions
Organisme : Deutsche Forschungsgemeinschaft
ID : BU1351/17-1
Références
Adorjan B, Buchbauer G. Biological properties of essential oils: an updated review. Flavour Frag J. 2010;25(6):407–26. https://doi.org/10.1002/ffj.2024 .
doi: 10.1002/ffj.2024
Niebler J, Zhuravlova K, Minceva M, Buettner A. Fragrant Sesquiterpene ketones as trace constituents in frankincense volatile oil of Boswellia sacra. J Nat Prod. 2016;79(4):1160–4. https://doi.org/10.1021/acs.jnatprod.5b00836 .
doi: 10.1021/acs.jnatprod.5b00836
pubmed: 27010489
Ishida T. Biotransformation of terpenoids by mammals, microorganisms, and plant-cultured cells. Chem Biodivers. 2005;2(5):569–90. https://doi.org/10.1002/cbdv.200590038 .
doi: 10.1002/cbdv.200590038
pubmed: 17192005
Schwab W, Fischer T, Wust M. Terpene glucoside production: improved biocatalytic processes using glycosyltransferases. Eng Life Sci. 2015;15(4):376–86. https://doi.org/10.1002/elsc.201400156 .
doi: 10.1002/elsc.201400156
Pauli GF, Pro SM, Friesen JB. Countercurrent separation of natural products. J Nat Prod. 2008;71(8):1489–508. https://doi.org/10.1021/np800144q .
doi: 10.1021/np800144q
pubmed: 18666799
Friesen JB, McAlpine JB, Chen SN, Pauli GF. Countercurrent separation of natural products: an update. J Nat Prod. 2015;78(7):1765–96. https://doi.org/10.1021/np501065h .
doi: 10.1021/np501065h
pubmed: 26177360
pmcid: 4517501
Ito Y. Golden rules and pitfalls in selecting optimum conditions for high-speed counter-current chromatography. J Chromatogr A. 2005;1065(2):145–68. https://doi.org/10.1016/j.chroma.2004.12.044 .
doi: 10.1016/j.chroma.2004.12.044
pubmed: 15782961
Sutherland IA, Fisher D. Role of counter-current chromatography in the modernisation of Chinese herbal medicines. J Chromatogr A. 2009;1216(4):740–53. https://doi.org/10.1016/j.chroma.2008.11.095 .
doi: 10.1016/j.chroma.2008.11.095
pubmed: 19108842
Skalicka-Wozniak K, Garrard I. Counter-current chromatography for the separation of terpenoids: a comprehensive review with respect to the solvent systems employed. Phytochem Rev. 2014;13:547–72. https://doi.org/10.1007/s11101-014-9348-2 .
doi: 10.1007/s11101-014-9348-2
pubmed: 24899873
pmcid: 4032468
Mischko W, Hirte M, Roehrer S, Engelhardt H, Mehlmer N, Minceva M, et al. Modular biomanufacturing for a sustainable production of terpenoid-based insect deterrents. Green Chem. 2018;20(11):2637–50. https://doi.org/10.1039/c8gc00434j .
doi: 10.1039/c8gc00434j
Hirte M, Mischko W, Kemper K, Rohrer S, Huber C, Fuchs M, et al. From microbial upcycling to biology-oriented synthesis: combining whole-cell production and chemo-enzymatic functionalization for sustainable taxanoid delivery. Green Chem. 2018;20(23):5374–84. https://doi.org/10.1039/c8gc03126f .
doi: 10.1039/c8gc03126f
Kessler A, Sahin-Nadeem H, Lummis SC, Weigel I, Pischetsrieder M, Buettner A, et al. GABA(A) receptor modulation by terpenoids from Sideritis extracts. Mol Nutr Food Res. 2014;58(4):851–62. https://doi.org/10.1002/mnfr.201300420 .
doi: 10.1002/mnfr.201300420
pubmed: 24273211
Schlicher H. Die Kamille - Handbuch für Ärzte, Apotheker und andere Naturwissenschaftler. Stuttgart: Wissenschaftliche Verlagsgesellschaft mbH; 1987.
Heuskin S, Godin B, Leroy P, Capella Q, Wathelet JP, Verheggen F, et al. Fast gas chromatography characterisation of purified semiochemicals from essential oils of Matricaria chamomilla L. (Asteraceae) and Nepeta cataria L. (Lamiaceae). J Chromatogr A. 2009;1216(14):2768–75. https://doi.org/10.1016/j.chroma.2008.09.109 .
doi: 10.1016/j.chroma.2008.09.109
pubmed: 18952218
Stanojevic LP, Marjanovic-Balaban ZR, Kalaba VD, Stanojevic JS, Cvetkovic DJ. Chemical composition, antioxidant and antimicrobial activity of chamomile flowers essential oil (Matricaria chamomilla L.). J Essent Oil Bear Plants. 2016;19(8):2017–28. https://doi.org/10.1080/0972060x.2016.1224689 .
doi: 10.1080/0972060x.2016.1224689
Tschiggerl C, Bucar F. Guaianolides and volatile compounds in chamomile tea. Plant Foods Hum Nutr. 2012;67(2):129–35. https://doi.org/10.1007/s11130-012-0277-1 .
doi: 10.1007/s11130-012-0277-1
pubmed: 22410959
Orav A, Raal A, Arak E. Content and composition of the essential oil of Chamomilla recutita (L.) Rauschert from some European countries. Nat Prod Res. 2010;24(1):48–55. https://doi.org/10.1080/14786410802560690 .
doi: 10.1080/14786410802560690
pubmed: 20013472
Engel W, Bahr W, Schieberle P. Solvent assisted flavour evaporation - a new and versatile technique for the careful and direct isolation of aroma compounds from complex food matrices. Eur Food Res Technol. 1999;209(3–4):237–41. https://doi.org/10.1007/s002170050486 .
doi: 10.1007/s002170050486
Bemelmans JMH. Review of isolation and concentration techniques. In: Progress in Flavour Research. London: Applied Science Publisher; 1979. p. 79–98.
Klamt A. Conductor-like screening model for real solvents - a new approach to the quantitative calculation of solvation phenomena. J Phys Chem. 1995;99(7):2224–35. https://doi.org/10.1021/j100007a062 .
doi: 10.1021/j100007a062
Hopmann E, Frey A, Minceva M. A priori selection of the mobile and stationary phase in centrifugal partition chromatography and counter-current chromatography. J Chromatogr A. 2012;1238:68–76. https://doi.org/10.1016/j.chroma.2012.03.035 .
doi: 10.1016/j.chroma.2012.03.035
pubmed: 22503586
Frey A, Hopmann E, Minceva M. Selection of biphasic liquid systems in liquid-liquid chromatography using predictive thermodynamic models. Chem Eng Technol. 2014;37(10):1663–74. https://doi.org/10.1002/ceat.201400234 .
doi: 10.1002/ceat.201400234
Luca SV, Roehrer S, Kleigrewe K, Minceva M. Approach for simultaneous cannabidiol isolation and pesticide removal from hemp extracts with liquid-liquid chromatography. Ind Crop Prod. 2020;155. https://doi.org/10.1016/j.indcrop.2020.112726 .
Martin AJ, Synge RL. A new form of chromatogram employing two liquid phases: a theory of chromatography. 2. Application to the micro-determination of the higher monoamino-acids in proteins. Biochem J. 1941;35(12):1358–68. https://doi.org/10.1042/bj0351358 .
doi: 10.1042/bj0351358
pubmed: 16747422
pmcid: 1265645
Volkl J, Arlt W, Minceva M. Theoretical study of sequential centrifugal partition chromatography. AICHE J. 2013;59(1):241–9. https://doi.org/10.1002/aic.13812 .
doi: 10.1002/aic.13812
Hopmann E, Minceva M. Separation of a binary mixture by sequential centrifugal partition chromatography. J Chromatogr A. 2012;1229:140–7. https://doi.org/10.1016/j.chroma.2011.12.102 .
doi: 10.1016/j.chroma.2011.12.102
pubmed: 22307154
Goll J, Frey A, Minceva M. Study of the separation limits of continuous solid support free liquid-liquid chromatography: separation of capsaicin and dihydrocapsaicin by centrifugal partition chromatography. J Chromatogr A. 2013;1284:59–68. https://doi.org/10.1016/j.chroma.2013.01.116 .
doi: 10.1016/j.chroma.2013.01.116
pubmed: 23466203
Roehrer S, Minceva M. Evaluation of inter-apparatus separation method transferability in countercurrent chromatography and centrifugal partition chromatography. Separations. 2019;6(3). https://doi.org/10.3390/separations6030036 .
Adams RP. Identification of essential oil components by gas chromatography/mass spectrometry. 4th ed. Allured Business Media: Carol Stream; 2012.
Friesen JB, Pauli GF. GUESS - a generally useful estimate of solvent systems in CCC. J Liq Chromatogr Relat Technol. 2005;28(17):2777–806. https://doi.org/10.1080/10826070500225234 .
doi: 10.1080/10826070500225234
Chanotiya CS, Sammal SS, Mathela CS. Composition of a new chemotype of Tanacetum nubigenum. Indian J Chem B. 2005;44(9):1922–6.
Sanz JF, Falco E, Marco JA. New acetylenes from Chrysanthemum-coronarium Indian J Chem Sect B-Org Chem Incl Med Chem 1990;3:303–5. https://doi.org/10.1002/jlac.199019900156 .
Avonto C, Wang M, Chittiboyina AG, Avula B, Zhao J, Khan IA. Hydroxylated bisabolol oxides: evidence for secondary oxidative metabolism in Matricaria chamomilla. J Nat Prod. 2013;76(10):1848–53. https://doi.org/10.1021/np4003349 .
doi: 10.1021/np4003349
pubmed: 24070008