Carboxylic acids of phenolic complexes from Veronica teucrium L.

А. Р. Osmachko, А. М. Kovaleva, Т. V. Ilyina, О. М. Koshovyi

Abstract


Aim. To compare and study low molecular aliphatic, fatty and aromatic acids of phenolic complexes (PhC) obtained from V. teucrium L. flowers, leaves and rhizomes using chromatography-mass spectrometry.
Materials and methods. Phenolic complexes from flowers, leaves and rhizomes were obtained by the exhaustive circulating extraction method in a Soxhlet apparatus. The analysis of methyl esters of acids was performed on a 5973N/6890N MSD/DS Agilent Technologies (USA) chromatograph using the chromatography-mass spectrometry method. The sample injection in a HP-INNOWAX (0.25 mm × 30 m) chromatographic capillary column was performed by a splitless mode. Identification of methyl esters of acids was performed based on the calculation of the equivalent length of the aliphatic chain (ECL) using data from the mass spectra libraries NIST 05 and Willey 2007 in combination with programs for identifying AMDIS and NIST; the retention time of esters was also compared with the retention time of standard compounds (Sigma). The internal standard method was used for quantitative calculations.
Results and discussion. As the result of our study low molecular aliphatic, fatty and aromatic acids have been identified in phenolic complexes of V. teucrium L. flowers, leaves and rhizomes for the first time, their quantitative content is as follows: 2.34 % – in the complex from flowers, 2.78 % – in the complex from leaves, and 2.10 % – in the complex from rhizomes. In the phenolic complex from flowers low molecular aliphatic acids (malonic, levulinic, succinic, 3-hydroxy-2-methylglutaric); fatty acids (palmitic and linolenic); aromatic acids (vanillic, р-coumaric and phydroxybenzoic) prevail. The dominant compounds in the phenolic complex from leaves are low molecular aliphatic acids (malonic, levulinic, succinic, 3-hydroxy-2-methylglutaric, malic); fatty acids (palmitic, oleic, linoleic, linolenic); and aromatic acid (ferulic). In the phenolic complex from rhizomes low molecular aliphatic acids (levulinic, succinic, malic); fatty acids (palmitic, stearic, oleic, linoleic, linolenic); aromatic acids (veratric, vanillic, syringic, ferulic) dominate.
Conclusions. As the result of our study for the first time the following components have been identified in phenolic complexes: 40 low molecular aliphatic, fatty and aromatic acids – from flowers, 39 – from leaves, 38 – from rhizomes. The content of carboxylic acids in phenolic complexes is 2.34 % – from flowers, 2.78 % – from leaves, 2.10 % – from rhizomes. It has been found that the herbal drug of V. teucrium L. is a source of valuable biologically active acids with different pharmacological effect.


Keywords


Veronica teucrium L.; low molecular aliphatic acids; fatty acids; aromatic acids; phenolic complex from flowers; leaves and rhizomes

Full Text:

PDF

References


Mosyakin, S. L., Fedoronchuk, M. M. (1999). Vascular plants of Ukraine: A nomenclatural checklist. Kiev, 24, 346.

Belenovskaia, L., Korhov, V., Matc, M., Medvedeva, L. (1990). Rastitelnye resursy SSSR. Tcvetkovye rasteniia, ikh khimicheskii sostav,

ispolzovanie. Semeistvo Caprifoliaceae – Plantaginaceae. L.: Nauka, 328.

Mocan, A., Vodnar, D., Vlase, L., Crișan, O., Gheldiu, A.–M., Crișan, G. (2015). Phytochemical Characterization of Veronica officinalis

L., V. teucrium L. and V. orchidea Crantz from Romania and Their Antioxidant and Antimicrobial Properties. International Journal of

Molecular Sciences, 16 (9), 21109–21127. doi: 10.3390/ijms160921109

Beara, I., Zivkovic, J., Lesjak, M., Ristic, J., Savikin, K., Maksimovic, Z., Jankovic, T. (2015). Phenolic profile and anti–inflammatory

activity of three Veronica species. Industrial Crops and Products, 63, 276–280. doi: 10.1016/j.indcrop.2014.09.034

Taskova, R., Albach, D., Grayer, R. (2004) Phylogeny of Veronica L. – a combination of molecular and chemical evidence. Plant Biology,

(6), 673–682. doi: 10.1055/s–2004–830330

Albach, D. C., Grayer, R. J., Jensen, S. R., Ozgokce, F., Veitch, N. C. (2003). Acylated flavone glycosides from Veronica. Phytochemistry,

(7), 1295–1301. doi: 10.1016/j.phytochem.2003.08.012

Оsmachko, А. P., Kovalova, А. М., Кashpur, N. V., Hrudko, I. V. (2016) Ukrainskyi biofarmatsevtychnyi zhurnal, 1 (42), 58–62.

Osmachko, A. P., Kovaleva, A. M., Ilyina, T. V., Kashpur, N. V., Koshovyi, O. M., Komisarenko, A. M. (2017). The study of the chemical

composition and the immunomodulatory activity of polysaccharide complexes from Veronica teucrium L. Vìsnik farmacìï, 2(90),

–42. doi: 10.24959/nphj.17.2170

Zivkovic, J., Cebovic, T., Maksimovic, Z. (2012). In vivo and in vitro antioxidant effects of three Veronica spesies. Open Life Sciences,

(3), 559–568. doi: 10.2478/s11535–012–0041–4

Ilina, T. V., Goryacha, O. V., Kovalyova, A. M., Koshovyi, O. M. (2017). Carboxylic acids and amino acids of Galium pseudomollugo

herb. Der Pharma Chemica, 9 (11), 91–94.

Bicchi, C., Brunelli, C., Cordero, C., Rubiolo, P., Galli, M., Sironi, A. (2004). Direct resistively heated column gas chromatography

(Ultrafast module–GC) for high–speed analysis of essential oils of differing complexities. J. Chromatogr. A., 1024 (1–2), 195–207.

doi: 10.1016/j.chroma.2003.10.018

Christie, W. W. (1989). Gas chromatography and lipids: a practical guide. The Oily Press, Ayr., 307.

Diakov, A. A., Perfilova, V. N., Tiurenkov, I. N. (2005). Vestnik aritmologii, 39, 49–52.

Sharma, P. (2011). Cinnamic acid derivatives: a new chapter of various pharmacological activities. Journal of Chemical and Pharmaceutical

Research, 3 (2), 403–423.


GOST Style Citations


1. Mosyakin, S. L. Vascular plants of Ukraine : A nomenclatural checklist / S. L. Mosyakin, M. M. Fedoronchuk. – K., 1999. – Vol. 24. – 346 p.

2. Растительные ресурсы СССР. Цветковые растения, их химический состав, использование. Семейство Caprifoliaceae – Plantaginaceae /
ред. Л. Беленовская, В. Корхов, М. Мац, Л. Медведева. – Л. : Наука, 1990. – 328 с.

3. Phytochemical characterization of Veronica officinalis L., V. teucrium L. and V. orchidea Crantz from Romania and their antioxidant
and antimicrobial properties / A. Mocan, D. C. Vodnar, L. Vlase et al. // Intern. J. of Molecular Sci. – 2015. – Vol. 16, Issue 9. –
P. 21109–21127. doi: 10.3390/ijms160921109

4. Phenolic profile and anti–inflammatory activity of three Veronica species / I. Beara, J. Zivkovic, M. Lesjak et al. // Industrial Crops and
Products. – 2015. – Vol. 63. – Р. 276–280. doi: 10.1016/j.indcrop.2014.09.034

5. Taskova, R. Phylogeny of Veronica L. – a combination of molecular and chemical evidence / R. Taskova, D. Albach, R. Grayer // Plant
Biology. – 2004. – Vol. 6, Issue 6. – P. 673–682. doi: 10.1055/s–2004–830330

6. Acylated flavone glycosides from Veronica L. / D. C. Albach, R. J. Grayer, S. R. Jensen et al. // Phytochem. – 2003. – Vol. 64, Issue 7. –
P. 1295–1301. doi: 10.1016/j.phytochem.2003.08.012

7. Антибактеріальна активність комплексів з трави вероніки довголистої / А. П. Осьмачко, А. М. Ковальова, Н. В. Кашпур,
І. В. Грудько // Укр. біофармац. журн. – 2016. – № 1 (42). – С. 58–62.

8. The study of the chemical composition and the immunomodulatory activity of polysaccharide complexes from Veronica teucrium L.
/ А. P. Оsmachko, А. М. Kovaleva, Т. V. Ilyina et al. // Вісник фармації. – 2017. – № 2 (90). – С. 37–42. doi: 10.24959/nphj.17.2170

9. Zivkovic, J. In vivo and in vitro antioxidant effects of three Veronica spesies / J. Zivkovic, T. Cebovic, Z. Maksimovic // Open Life Sci. –
2012. – Vol. 7, Issue 3. – P. 559–568. doi: 10.2478/s11535–012–0041–4

10. Carboxylic acids and amino acids of Galium pseudomollugo herb / T. V. Ilina, O. V. Goryacha, A. M. Kovalyova, O. M. Koshovyi // Der
Pharma Chemica. – 2017. – Vol. 9, Issue 11. – Р. 91–94.

11. Direct resistively heated column gas chromatography (Ultrafast module–GC) for high–speed analysis of essential oils of differing complexities
/ C. Brunelli, C. Cordero, P. Rubiolo et al. // J. Chromatogr. A. – 2004. – Vol. 1024, Issue 1–2. – Р. 195–207. doi: 10.1016/j.
chroma.2003.10.018

12. Christie, W. W. Gas chromatography and lipids : a practical guide / W. W. Christie // The Oily Press, Ayr.–1989. – 307 p.

13. Дъяков, А. А. Противоаритмическое действие феруловой кислоты / А. А. Дъяков, В. Н. Перфилова, И. Н. Тюренков // Вестник
аритмол. – 2005. – № 39. – С. 49–52.

14. Sharma, P. Cinnamic acid derivatives : a new chapter of various pharmacological activities / P. Sharma // J. of Chem. and Pharmac.
Res. – 2011. – Vol. 3, Issue 2. – P. 403–423.





DOI: https://doi.org/10.24959/nphj.17.2179

Abbreviated key title: Vìsn. farm.

ISSN 2415-8844 (Online), ISSN 1562-7241 (Print)