Phenolic compounds of the liquid extract from cleavers herb (galium aparine l.)

I. L. Shynkovenko, T. V. Ilyina, O. V. Goryacha, A. M. Kovalyova, A. М. Komissarenko, N. S. Shemchuk, O. I. Golembiovska

Abstract


Aim. To study the qualitative composition and the quantitative content of phenolic compounds of the liquid extract obtained from cleavers (Galium aparine L.) herb.

Materials and methods. The extract of cleavers herb was obtained by triple extraction of the raw material with 60% ethanol when heating, followed by the concentration of the combined extracts to the ratio of the raw material: finished product of 1:1. The content of extractives was determined by the gravimetric method. Phenolic compounds were studied by the methods of high-performance liquid chromatography (HPLC) and UV-spectrophotometry.

Results. In the chromatographic study of the extract from cleavers herb 11 compounds of phenolic nature were reliably identified, including 5 hydroxycinnamic acids – caffeic, сhlorogenic, neoсhlorogenic, 3,5- and 4,5-dicaffeoylquinic acids; and 6 flavonoids – catechin, quercetin, quercitrin, isoquercitrin, rutin and hyperoside. Rutin (1.89 mg/ml) and сhlorogenic acid (0.78 mg/ml) were predominant compounds. In the spectrophotometric determination of total content of phenolic compounds it was found that the amount for hydroxycinnamic acids calculated with reference to сhlorogenic acid was 1.9 %, for flavonoids calculated with reference to rutin – 0.25 %, for polyphenolic compounds calculated with reference to gallic acid – 1.35 %. The dry residue was 24.63 %.

Conclusions. The significant content of extractive substances, flavonoids and у hydroxycinnamic acids with predominance of rutin and сhlorogenic acid in alcohol-water extract from cleavers herb indicate the feasibility of its further pharmacological study.


Keywords


Galium aparine L.; liquid extract; phenolic compounds.

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References


Tobyn, G., Denham, A., Whitelegg, M., Rowling, M. (2016). The Western herbal tradition : 2000 years of medicinal plant knowledge. Singing Dragon, 379.

Deliorman, D., Çalis, I., Ergun, F. (2001). Iridoids from Galium aparine. Pharmaceutical Biology, 39 (3), 234–235. https://doi.org/10.1076/phbi.39.3.234.5928

Sener, B., Ergun, F. (1988). Isolation and structural studies on the alkaloids of Galium aparine L.. Guede J. Fac. Pharm. Gazi, 5, 33–40.

Tzakou, O., Couladi, M. M., Philianos, S. (1990). Fatty acids and sterols in spring and winter samples of Galium aparine. Fitoterapia, 61, 93.

Moubasher, H., Abd El–Ghani, M., Al–Wakeel, S., Bahoor, A. (2016). Chemotaxonomic significance of flavonoids in some species of Galium (Rubiaceae) from Libya. Austin J. Plant Biol., 2, 1014–1021.

Vlase, L., Mocan, A., Hanganu, D. et al. (2014). Comparative study of polyphenolic content, antioxidant and antimicrobial activity of four Galium species (Rubiaceae). Dig. J. Nanomater. Biostructures, 9, 1085–1094.

Mocan, A., Crişan, G., Vlase, L. et al. (2016). Phytochemical investigations on four Galium species (Rubiaceae) from Romania. Farmacia, 64, 95–99.

Aslantürk, Ö., Çelik, T., Karabey, B., Karabey, F. (2017). Active Phytochemical Detecting, Antioxidant, Cytotoxic, Apoptotic Activities of Ethyl Acetate and Methanol Extracts of Galium aparine L. British Journal of Pharmaceutical Research, 15 (6), 1–16. https://doi.org/10.9734/bjpr/2017/32762

Goryacha, O. V., Ilyina, T. V., Kovalyova, A. M., Kashpur, N. V. (2014). Phytochemical research of Galium aparine L. lipophilic complex and study of its antibacterial activity. Pharma Innov. J., 3, 7–10.

Derzhavna Farmakopeia Ukrainy, 1–e vyd., 1–e dop. (2004). Kharkiv: RIREG, 494.

Yezerska, O., Kalynyuk, T., Vronska, L. (2013). Quantitative determination of hydroxycinnamic acids in Chicory root. Chemistry and chemical technology, 7 (3), 247–250.

Spagnol, C. M., Oliveira, Th. S., Lucia Borges, V. I. et al. (2015). Validation of Caffeic Acid in Emulsion by UV–Spectrophotometric Method. Physical Chemistry, 5 (1), 16–22.

Derzhavna Farmakopeia Ukrainy, 1–e vyd., 2–e dop. (2008). Kharkiv: Ukrainskyi naukovyi farmakopeinyi tsentr yakosti likarskykh zasobiv, 620.

Kovalova, A. M., Heorhievskii, H. V., Kovalov, V. M. et al. (2002). Farmakom, 2, 92–97.

Koshevoi, O. N., Zagayko, A. L., Kolychev, I. A. et al. (2016). Azərbaycan əczaçiliq və farmakoterapiya jurnali, 1, 18–23.

Golembiovska, O. I. (2014). Simultaneous determination of flavonoids and phenolic acids in different parts of Prunella vulgaris L. by high–performance liquid chromatography with photodiode array detection. Int. J. Pharmacog. Phytochem., 29 (1), 1248–1255.

Holembiovska, O. I. (2012). Visnyk stomatolohii, 7 (80), 26–27.

Gudzenko, A. (2013). Development and Validation of a RP–HPLC Method for The Simultaneous Determination of Luteolin and Apigenin in Herb of Achillea millefolium L.. Pharma Innov. J., 2 (7), 7–14.


GOST Style Citations


1. The Western herbal tradition : 2000 years of medicinal plant knowledge / G. Tobyn, A. Denham, M. Whitelegg, M. Rowling. – Singing Dragon, 2016. – 379 р.

2. Deliorman, D. Iridoids from Galium aparine / D. Deliorman, I. Çalıs, F. Ergun // Pharmac. Biol. – 2001. – Vol. 39, Issue 3. – Р. 234–235. doi: 10.1076/phbi.39.3.234.5928

3. Sener, B. Isolation and structural studies on the alkaloids of Galium aparine L. / B. Sener, F. Ergun // Guede J. Fac. Pharm. Gazi. – 1988. – Vol. 5. – Р. 33–40.

4. Tzakou, O. Fatty acids and sterols in spring and winter samples of Galium aparine / O. Tzakou, M. M. Couladi, S. Philianos // Fitoterapia. – 1990. – Vol. 61. – 93 p.

5. Chemotaxonomic significance of flavonoids in some species of Galium (Rubiaceae) from Libya / H. Moubasher, M. Abd El–Ghani,
S. Al–Wakeel, A. Bahoor // Austin J. Plant Biol. – 2016. – Vol. 2. – P. 1014–1021.

6. Comparative study of polyphenolic content, antioxidant and antimicrobial activity of four Galium species (Rubiaceae) / L. Vlase,
A. Mocan, D. Hanganu et al. // Dig. J. Nanomater. Biostructures. – 2014. – Vol. 9. – Р. 1085–1094.

7. Phytochemical investigations on four Galium species (Rubiaceae) from Romania / A. Mocan, G. Crişan, L. Vlase et al. // Farmacia. –
2016. – Vol. 64. – Р. 95–99.

8. Active Phytochemical Detecting, Antioxidant, Cytotoxic, Apoptotic Activities of Ethyl Acetate and Methanol Extracts of Galium
aparine L. / Ö. Aslantürk, T. Çelik, B. Karabey, F. Karabey // Br. J. Pharm. Res. – 2017. – Vol. 15, Issue 6. – Р. 1–16. doi: 10.9734/
bjpr/2017/32762

9. Phytochemical research of Galium aparine L. lipophilic complex and study of its antibacterial activity / O. V. Goryacha, T. V. Ilyina,
A. M. Kovalyova, N. V. Kashpur // Pharma Innov. J. – 2014. – Vol. 3. – Р. 7–10.

10. Державна фармакопея України / Державне підприємство «Науково–експертний фармакопейний центр». – 1–е вид., 1 доп. – Х. : РІРЕГ, 2004. – 494 с.

11. Yezerska, O. Quantitative determination of hydroxycinnamic acids in Chicory root / O. Yezerska, T. Kalynyuk, L. Vronska // Chemistry and Chemical Technol. – 2013. – Vol. 7, Issue 3. – Р. 247–250.

12. Validation of Caffeic Acid in Emulsion by UV–Spectrophotometric Method / C. M. Spagnol, Th. S. Oliveira, V. I. Lucia Borges et al. // Physical Chem. – 2015. – Vol. 5, Issue 1. – Р. 16–22.

13. Державна фармакопея України / Державне підприємство «Науково–експертний фармакопейний центр». – 1–е вид., 2 доп. – Х. : Науково–експертний фармакопейний центр, 2008. – 620 с.

14. Розробка методів стандартизації нового лікарського засобу піфламін / А. М. Ковальова, Г. В. Георгієвський, В. М. Ковальов та ін. // Фармаком. – 2002. – № 2. – С. 92–97.

15. Фитохимическое изучение сухого экстракта из листьев черники обыкновенной / О. Н. Кошевой, А. Л. Загайко, И. А. Колычев и др. // Azərbaycan əczaçiliq və farmakoterapiya jurnali. – 2016. – № 1. – Р. 18–23.

16. Golembiovska, O. I. Simultaneous determination of flavonoids and phenolic acids in different parts of Prunella vulgaris L. by high–performance liquid chromatography with photodiode array detection / O. I. Golembiovska // Int. J. Pharmacog. Phytochem. – 2014. – Vol. 29, Issue 1. – Р. 1248–1255.

17. Голембіовська, O. I. Розділення та ідентифікація поліфенолів суцвітть Prunella vulgaris L. методом ВЕРХ / O. I. Голембіовська // Вісник стоматол. – 2012. – № 7 (80). – С. 26–27.

18. Gudzenko, A. Development and Validation of a RP–HPLC Method for The Simultaneous Determination of Luteolin and Apigenin in Herb of Achillea millefolium L. / A. Gudzenko // Pharma Innov. J. – 2013. – Vol. 2, Issue 7. – P. 7–14.





DOI: https://doi.org/10.24959/nphj.18.2213

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