One-step multiple component isolation from the oil of Crinitaria tatarica (Less) Sojak by preparative capillary gas chromatography with characterization by spectroscopic and spectrometric techniques

Authors: OZEK, GULMIRAA - Anadolu Universtiy; ISHMURATOVA, M - Zhezkazghan Botanical Garden; Tabanca, Nurhayat; RADWAN, MOHAMED - Anadolu Universtiy; GOGER, FATIH - Anadolu Universtiy; OZEK, TEMEL - Anadolu Universtiy; Wedge, David; Becnel, James; CUTLER, STEPHEN - University Of Mississippi; BASER, KEMAL HUSNU CAN - King Saud University

Submitted to: Journal of Separation Science
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 12/11/2011
Publication Date: 2/14/2012
Citation: Ozek, G., Ishmuratova, M., Tabanca, N., Radwan, M.M., Goger, F., Ozek, T., Wedge, D.E., Becnel, J.J., Cutler, S.J., Baser, K. 2012. One-step multiple component isolation from the oil of Crinitaria tatarica (Less) Sojak by preparative capillary gas chromatography with characterization by spectroscopic and spectrometric techniques. Journal of Separation Science. 35:650-660.

Interpretive Summary: Further knowledge of the chemical composition of the plant Crinitaria tatarica from Kazakhstan, as well as of its biological properties is provided. Essential oil of C. tatarica was analyzed by gas chromatography and mass spectrometry, and the oil was rich in monoterpenes and isocoumarins. The isocoumarims were isolated by preparative capillary gas chromatography and identified as, Z-artemidin and E-artemidin by spectroscopic analysis for the first time in the Crinitaria genus. Z-Artemidin possessed weak activity against the plant pathogen Botrytis cinerea and larvicidal activity against the mosquito Aedes aegypti. The oil and pure compounds also possessed weak antioxidant activity.

Technical Abstract: In the present work multiple component isolation from the oil of Crinitaria tatarica (Less.) Sojak. by Preparative Capillary Gas Chromatography (PCGC) with characterization by mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopy have been carried out. Gas chromatography (GC-FID) and gas chromatography coupled to mass spectrometry (GC/MS) revealed that the oil was rich in sabinene (32.1%), B-pinene (8.8%) and two unknown (M+200) compounds (I and II) (21.4% and 3.4%). One step fractionation of the oil and separation of unknown constituents were performed using automated PCGC connected to Preparative Fraction Collector (PFC) to separate and recover sufficient quantities of the individual target compounds. Two unknown constituents have been isolated from the oil with 95.0% purity. Structure determination was accomplished by spectral analysis, including UV, 1H-NMR (in CDCl3), 13C-NMR (in CDCl3) and HR-ESI-MS. Z- (I) and E-artemidin (II) were isolated for the first time for this species. The oil and cis-artemidin were evaluated for antifungal and insecticidal activities. Crinitaria tatarica oil and Z- (I) and E-artemidin (II) showed anatifungal activity against the strawberry anthracnose-causing fungal plant pathogens Colletotrichum acutatum, C. fragariae and C. gloeosporioides using the direct overlay bioautography assay. Isolated pure compounds were sebsequeltly tested for growth inhibition of several plant pathogenic fungi from the genera Colletotrichum, Botrytis, Fusarium and Phomopsis. Compound I demonstrated selective activity against the Botrytis, Fusarium and Phomopsis species and the other compounds were inactive. In addition, C. tatarica oil and Z-artemidin (I) were also investigated against Aedes aegypti first instar larvae in a high throughput bioassays. The oil and compound I showed 100% mortality at the highest comcentartion on Ae. aegypti larvae. The oil and compound I showed weak activity against adult Ae. aegypti. The oil demonstrated weak antioxidant activity (AOA) in B-carotene bleaching, Trolox equivalent and DPPH tests. To the best of our knowledge, the present work is the first contribution into the chemistry and activity of Crinitaria tatarica oil.