Cytotoxic evaluation and LC-MS/MS analysis of aerial parts of <i>Eryngium kotschyi</i> Boiss. grown in Turkey

Arslan, Ayşe Kübra Karaboğa; Paşayeva, Leyla; Tugay, Osman

doi:10.1590/s2175-97902022e19194

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Brazilian Journal of Pharmaceutical Sciences

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Article • Braz. J. Pharm. Sci. 58 • 2022 • https://doi.org/10.1590/s2175-97902022e19194 copy

Cytotoxic evaluation and LC-MS/MS analysis of aerial parts of Eryngium kotschyi Boiss. grown in Turkey

Authorship SCIMAGO INSTITUTIONS RANKINGS

Abstract

Increasing biological activity and phytochemical investigations on Eryngium species showed its potential as pharmaceutical approach. Eryngium kotschyi Boiss. is one of the species of Eryngium genus and is endemic to Turkey. It is known that this plant is traditionally used in the South-western part of Turkey for the treatment of various diseases. This study focuses on cytotoxic activities of methanol extract and ethyl acetate, n-butanol and water sub-extracts from E. kotschyi in A549, COLO 205 and MDA-MB-231 cell lines by Sulforhodamin B assay and qualitative and quantitative determination of phytochemical constituents in active extract by LC-MS/MS. From the result of the study, it was seen that E. kotschyi ethyl acetate (EKE) sub-extract showed the strongest cytotoxic effect with the low IC₅₀ values (50.00; 31.96 and 22.26 μg/mL in A549; COLO 205 and MDA-MB-231 cells at 48 h, respectively). Preliminary examination of the mass spectrums revealed the presence of 15 phytochemical compounds in active sub-extract and 7 of them was quantiﬁed. According to quantitative analyses the main compounds of EKE sub-extract were rosmarinic acid (485.603 µg/mg_extract), chlorogenic acid (62.355 µg/mg_extract) and caffeic acid (59.266 µg/mg_extract). Moreover, this preliminary study on inhibitory activity of EKE sub-extract suggests further toxicologic investigations and detailed investigation on cytotoxic effect of various combinations of determined compounds.

Keywords:
Eryngium kotschyi; LC-MS/MS; A549; COLO 205; MDA-MB-231; SRB

Extracts	Extract code	Yields (%)
Methanol	EKM	10
Ethyl acetate	EKE	25
n-butanol	EKB	30
Water	EKW	30

Cell line	Extract code	24 h IC50 (µg/mL)	48 h IC50 (µg/mL)
A549	EKB	N.D.	N.D.
	EKE	N.D.	50.00±0.061
	EKM	N.D.	308.80±0.042
	EKW	N.D.	N.D.
COLO 205	EKB	N.D.	N.D.
	EKE	86.93±0.041	31.96±0.023
	EKM	N.D.	138.00±0.134
	EKW	N.D.	N.D.
MDA-MB-231	EKB	N.D.	N.D.
	EKE	15.35±0.112	22.26±0.120
	EKM	249.90±124	34.59±0.041
	EKW	N.D.	N.D.

Pik No	RT (min)	[M−H]⁻ (m/z)	*MS/MS (m/z)*	Compounds	References
1	4.31	359	133,161,179	Rosmarinic acid	(*Tang, et al., 2016*Tang CB, Zhang WG, Wang YS, Xing LJ, Xu XL, Zhou GH. Identiﬁcation of rosmarinic acid-adducted sites in meat proteins in a gel model under oxidative stress by triple TOF MS/MS. J Agric Food Chem . 2016;64(33):6466-6476.)
2	4.42	377	341, 215, 179, 161,119	Caffeic acid derivative-I	(*Riethmüller, et al.,* 2013**Riethmüller E, Alberti Á, Tóth G, Béni S, Ortolano F, Kéry Á. Characterisation of diarylheptanoid- and flavonoid-type phenolics in Corylus avellana L. leaves and bark by HPLC/ DAD-ESI/MS. Phytochem Anal. 2013;24(5):493-503.)
3	5.15	191	191, 93, 85	Quinic acid	(*Clifford, et al.,* 2003**Clifford MN, Johnston KL, Knight S, Kuhnert N. Hierarchical scheme for LC-MS n identiﬁcation of chlorogenic acids. J Agric Food Chem . 2003;51(10):2900-2911.)
4	5.16	353	191	Cholorogenic acid	(*Lin, et al.,* 2000**Lin LZ, He XG, Lindenmaier M, Yang J, Cleary M, Qiu SX, et al. LC-ESI-MS study of the flavonoid glycoside malonates of red clover (Trifolium pratense). J Agric Food Chem . 2000;48(2):354-365.)
5	5.21	341	179,135	Caffeic acid-3-glucoside	(*Gardana, et al.,* 2007**Gardana C, Scaglianti M, Pietta P, Simonetti P. Analysis of the polyphenolic fraction of propolis from different sources by liquid chromatography-tandem mass spectrometry. J Pharm Biomed Anal . 2007;45(3):390-399.)
6	5.61	179	135, 87	Caffeic acid	(*Horai, et al.,* 2010**Horai H, Arita M, Kanaya S, Nihei Y, Ikeda T, Suwa K, Ojima Y, Tanaka K, Tanaka S, Aoshima K. MassBank: a public repository for sharing mass spectral data for life sciences. J Mass Spectrom. 2010;45(7):703-714.)
7	7.23	133	115	Malic acid	(*Gonzalez, et al.,* 2011**Gonzalez O, Alonso RM, Ferreirós N, Weinmann W, Zimmermann R, Dresen S. Development of an LC-MS/ MS method for the quantitation of 55 compounds prescribed in combined cardiovascular therapy. J Chromatogr B. 2011;879(3-4):243-252.)
8	8.10	609	301	Rutin	(*Karaçelik, et al., 2015*Karaçelik AA, Küçük M, İskeﬁyeli Z, Aydemir S, De Smet S, Miserez B, Sandra P. Antioxidant components of Viburnum opulus L. determined by on-line HPLC-UV-ABTS radical scavenging and LC-UV-ESI-MS methods. Food Chem . 2015;175:106-114.)
9	10.22	623	315	Isorhamnetine 3-O-rutinoside	(*Lin, et al.,* 2000**Lin LZ, He XG, Lindenmaier M, Yang J, Cleary M, Qiu SX, et al. LC-ESI-MS study of the flavonoid glycoside malonates of red clover (Trifolium pratense). J Agric Food Chem . 2000;48(2):354-365.)
10	13.91	593	285, 255	Kaempferol cumaroil hexoside	(Simirgiotis, Schmeda- Hirschmann,2010Simirgiotis MJ, Schmeda-Hirschmann G. Determination of phenolic composition and antioxidant activity in fruits, rhizomes and leaves of the white strawberry (Fragaria chiloensis spp. chiloensis form chiloensis) using HPLC-DAD-ESI-MS and free radical quenching techniques. J Food Compost Anal. 2010;23(6):545-553.)
11	14.22	387	223,191,179	5-cynapoil quinic acid	(*Lin, et al.,* 2000**Lin LZ, He XG, Lindenmaier M, Yang J, Cleary M, Qiu SX, et al. LC-ESI-MS study of the flavonoid glycoside malonates of red clover (Trifolium pratense). J Agric Food Chem . 2000;48(2):354-365.)
12	16.31	447	273, 285, 257, 151	Kaempferol-3-O-glucoside	(*Ribeiro, et al.,* 2008**Ribeiro S, Barbosa L, Queiroz J, Knödler M, Schieber A. Phenolic compounds and antioxidant capacity of Brazilian mango (Mangifera indica L.) varieties. Food Chem . 2008;110(3):620-626.)
13	29.3	577	269	Apigenin-7-O-rutinoside	(Lin, et al., 2000Lin LZ, He XG, Lindenmaier M, Yang J, Cleary M, Qiu SX, et al. LC-ESI-MS study of the flavonoid glycoside malonates of red clover (Trifolium pratense). J Agric Food Chem . 2000;48(2):354-365.)
14	32.12	455	289,183	Epicatechin-3-O-(4-O-methyl) gallat	(Kelebek, 2016Kelebek H. LC-DAD-ESI-MS/MS characterization of phenolic constituents in Turkish black tea: Effect of infusion time and temperature. Food Chem . 2016;204:227-238.)
15	34.79	735	191,193,367	Ferulic acid dimer	(Bravo, Goya, Lecumberri, 2007Bravo L, Goya L, Lecumberri R. LC/MS characterization of phenolic constituents of mate (Ilex paraguariensis, St. Hil.) and its antioxidant activity compared to commonly consumed beverages. Food Res Int. 2007;40(3):393-405.)

Constituent	Content (µg/mgextract)
Constituent	EKM	EKB	EKE	EKW
Malic acid	33.604±1.646	N.D.	N.D.	51.551±1.580
Caffeic acid	1.294±0.857	N.D.	59.266±2.838	2.018±0.542
Quinic acid	1.747±0.216	1.072±0.387	N.D.	1.753±0.566
Chlorogenic acid	36.850±0.340	30.717±0.188	62.355±0.270	17.735±0.240
Rutin	3.538±0.091	5.297±3.896	3.654±0.033	1.325±0.14
Isorhamnetin 3-O-rutinoside	34.957±3.468	92.559±1.030	2.770±0.676	N.D.
Rosmarinic acid	64.690±0.123	14.092±0.630	485.603±0.809	N.D.

Universidade de São Paulo, Faculdade de Ciências Farmacêuticas Av. Prof. Lineu Prestes, n. 580, 05508-000 S. Paulo/SP Brasil, Tel.: (55 11) 3091-3824 - São Paulo - SP - Brazil
E-mail: bjps@usp.br

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[1] *Correspondence: L. Paşayeva. Department of Pharmacognosy. Faculty of Pharmacy. Erciyes University. Zip code: 38039, Kayseri, Turkey. Phone: +903522076666/28277. E-mail: leylapasayeva@hotmail.com.