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Chemical profiling and cytotoxic activity of aqueous extract of Veronica peduncularis M.Bieb.: A chemotaxonomical approach

Year 2021, Volume: 51 Issue: 3, 372 - 377, 29.12.2021

Zeynep Doğan , Yasin Genç , Şebnem Harput , Asuman Karadeniz Pekgöz , İclal Saraçoğlu

Abstract

Background and Aims: Genus Veronica (Plantaginaceae) is represented by 79 species in Turkish flora, 26 of which are endemic. Veronica species have a variety of uses including diuretic, anticancer, and rheumatic pains, wounds, and respiratory problems. According to phytochemical studies, Veronica species contain predominantly iridoid glucosides with some phenylethanoid and flavonoid glycosides. Methods: The aqueous extract of Veronica peduncularis M.Bieb. was tested for its cytotoxic activity on human rhabdomyosarcoma (RD) and human epidermoid carcinoma (HEp-2) cell lines using the MTT method. Chemical profile of the extract was determined by HPLC-DAD, and isolation studies were conducted. Results: The extract was found to show concentration-dependent cytotoxicity against tested cell lines. In addition, a comparison of the iridoid fraction of Veronica peduncularis with previously isolated iridoid glucosides on the HPLC-DAD system, showed the presence of aucubin, amphicoside, veratroyl catalpol, and veronicoside in this fraction. On the other hand, isolation and structure elucidation of plantamajoside and 4'-O-methylisoscutellarein-7-O-2''-O-(6'''-O-acetyl-ß-D-allopyranosyl)- ß-D-glucopyranoside from the phenolic fractions were performed by serial chromatographic and spectroscopic methods. Conclusion: To the best of our knowledge, this is the first cytotoxic activity and phytochemical study on the titled plant. The presence of iridoid glucosides and 8-hydroxyflavone glycosides is important for the chemotaxonomy of the genus Veronica.

Keywords

4 HPLC iridoid glucosides phenolics plantamajoside Veronica

Supporting Institution

The Scientific and Technological Research Council of Turkey (TUBITAK)

Project Number

108T518

References

  • • Albach, D. C., Grayer, R. J., Jensen, S. R., Ozgokce, F., & Veitch, N. C. (2003). Acylated flavone glycosides from Veronica. Phytochemistry, 64(7), 1295-1301. http://dx.doi.org/10.1016/j.phytochem. 2003.08.012
  • • Albach, D. C., Jensen, S. R., Ozgokce, F., & Grayer, R. J. (2005). Veronica: Chemical characters for the support of phylogenetic relationships based on nuclear ribosomal and plastid DNA sequence data. Biochemical Systematics and Ecology, 33(11), 1087-1106. http://dx.doi.org/10.1016/j.bse.2005.06.002
  • • Baytop, T. (1999). Türkiye’de Bitkiler ile Tedavi (Geçmişte ve Bugün) (2nd ed.) [Therapy with medicinal plants in Turkey, Past and Present]. İstanbul, Turkey: Nobel Tıp Kitabevleri.
  • • Fischer, M. A. (1978). 17. Veronica L. In P.H. Davis (Ed.), Flora of Turkey and the East Aegean Islands. Volume Six (pp.489-753), Edinburgh, UK: Edinburgh University Press.
  • • Fujita, T., Sezik, E., Tabata, M., Yesilada, E., Honda, G., Tanaka, T., & Takaishi, Y. (1995). Traditional medicine in Turkey VII. Folk medicine in Middle and West Black Sea Regions. Economic Botany, 49, 406-422. http://dx.doi.org/10.1007/Bf02863092
  • • Graham, J. G., Quinn, M. L., Fabricant, D. S., & Farnsworth, N. R. (2000). Plants used against cancer - an extension of the work of Jonathan Hartwell. Journal of Ethnopharmacology, 73(3), 347-377. http://dx.doi.org/10.1016/S0378-8741(00)00341-X
  • • Harput, U. S., Genc, Y., Khan, N., & Saracoglu, I. (2011). Radical scavenging effects of different Veronica species. Records of Natural Products, 5(2), 100-107.
  • • Harput, U. S., Genc, Y., & Saracoglu, I. (2012). Cytotoxic and antioxidative activities of Plantago lagopus L. and characterization of its bioactive compounds. Food and Chemical Toxicology, 50(5), 1554- 1559. http://dx.doi.org/10.1016/j.fct.2012.01.019
  • • Harput, U. S., Karadeniz, A., Genc, Y., & Saracoglu, I. (2009). Comparative Bioactivity Studies on Four Veronica species. FABAD Journal of Pharmaceutical Science, 34, 67-72.
  • • Harput, U. S., Saracoglu, I., Inoue, M., & Ogihara, Y. (2002). Antiinflammatory and cytotoxic activities of five Veronica species. Biological & Pharmaceutical Bulletin, 25(4), 483-486. http://dx.doi. org/10.1248/bpb.25.483
  • • Jensen, S. R., Albach, D. C., Ohno, T., & Grayer, R. J. (2005). Veronica: Iridoids and cornoside as chemosystematic markers. Biochemical Systematics and Ecology, 33(10), 1031-1047. http://dx.doi. org/10.1016/j.bse.2005.03.001
  • • Jensen, S. R., Opitz, S. E. W., & Gotfredsen, C. H. (2011). A new phenylethanoid triglycoside in Veronica beccabunga L. Biochemical Systematics and Ecology, 39(3), 193-197. http://dx.doi. org/10.1016/j.bse.2011.02.008
  • • Kawada, T., Yoneda, Y., Asano, R., Kan-No, I., & Schmid, W. (2006). Synthesis of plantamajoside, a bioactive dihydroxyphenylethyl glycoside from Plantago major L. Holzforschung, 60(5), 492-497. http://dx.doi.org/10.1515/Hf.2006.081
  • • Lenherr, A., Lahloub, M.F. & Sticher, O. (1984). Three flavonoid glycosides containing acetylated allose from Stachys recta. Phytochemistry, 23(10), 2343-2345.
  • • Mosmann, T. (1983). Rapid colorimetric assay for cellular growth and survival - application to proliferation and cytotoxicity assays. Journal of Immunological Methods, 65(1-2), 55-63. http://dx.doi. org/10.1016/0022-1759(83)90303-4
  • • NCI (National Cancer Institute). (2020, May 8). Antioxidants and Cancer Prevention [online]. Retrieved from https://www.cancer.gov/ about-cancer/causes-prevention/risk/diet/antioxidants-fact-sheet • Olmstead, R. G. (2002). Whatever happened to the Scrophulariaceae? Fremontia, 30(2), 13-22.
  • • Ozipek, M., Saracoglu, I., Kojima, K., Ogihara, Y., & Calis, I. (1999). Fuhsioside, a new phenylethanoid glucoside from Veronica fuhsii. Chemical & Pharmaceutical Bulletin, 47(4), 561-562.
  • • Ravn, H., Nishibe, S., Sasahara, M., & Li, X. B. (1990). Phenolic compounds from Plantago asiatica. Phytochemistry, 29(11), 3627-3631. http://dx.doi.org/10.1016/0031-9422(90)85289-R
  • • Salehi, B., Shetty, M. S., Kumar, N. V. A., Zivkovic, J., Calina, D., Docea, A. O., . . . Sharifi-Rad, J. (2019). Veronica plants-drifting from farm to traditional healing, food application, and phytopharmacology. Molecules, 24(13). http://dx.doi.org/10.3390/molecules24132454
  • • Saracoglu, I., & Harput, U. S. (2012). In vitro cytotoxic activity and structure activity relationships of iridoid glucosides derived from Veronica species. Phytotherapy Research, 26(1), 148-152. http:// dx.doi.org/10.1002/ptr.3546
  • • Saracoglu, I., Harput, U. S., & Ogihara, Y. (2004). Acylated flavone glycosides from Veronica pectinata var. glandulosa and V. persica. Turkish Journal of Chemistry, 28(6), 751-759.
  • • Saracoglu, I., Inoue, M., Calis, I. & Ogihara, Y. 1995. Studies on constituents with cytotoxic and cytostatic activity of two Turkish medicinal plants, Phlomis armeniaca and Scutellaria salviifolia. Biological & Pharmaceutical Bulletin, 18(10), 1396-1400.
  • • Saracoglu, I., Oztunca, F. H., Nagatsu, A., & Harput, U. S. (2011). Iridoid content and biological activities of Veronica cuneifolia subsp. cuneifolia and V. cymbalaria. Pharmaceutical Biology, 49(11), 1150- 1157. http://dx.doi.org/10.3109/13880209.2011.575790
  • • Saracoglu, I., Varel, M., Harput, U. S., & Nagatsu, A. (2004). Acylated flavonoids and phenol glycosides from Veronica thymoides subsp. pseudocinerea. Phytochemistry, 65(16), 2379-2385. http://dx.doi. org/10.1016/j.phytochem.2004.05.011
  • • Taskova, R. M., Albach, D. C., & Grayer, R. J. (2004). Phylogeny of Veronica - a combination of molecular and chemical evidence. Plant Biology, 6(6), 673-682. http://dx.doi.org/10.1055/s-2004-830330
  • • Tomas-Barberan, F. A., Grayerbarkmeijer, R. J., Gil, M. I., & Harborne, J. B. (1988). Distribution of 6-hydroxyflavone, 6-methoxyflavone and 8-hydroxyflavone glycosides in the Labiatae, the Scrophulariaceae and related families. Phytochemistry, 27(8), 2631-2645. http://dx.doi.org/10.1016/0031-9422(88)87034-1
  • • Wang, C. C., Gong, X., Bo, A., Zhang, L., Zhang, M. X., Zang, E. H., . . . Li, M. H. (2020). Iridoids: Research advances in their phytochemistry, biological activities, and pharmacokinetics. Molecules, 25(2). http://dx.doi.org/10.3390/molecules25020287
  • • Xue, H. B., Chen, K. X., Zhang, L. Q., & Li, Y. M. (2019). Review of the ethnopharmacology, phytochemistry, and pharmacology of the genus Veronica. American Journal of Chinese Medicine, 47(6), 1193- 1221. http://dx.doi.org/10.1142/S0192415x19500617
  • • Yin, L., Lu, Q. X., Tan, S. C., Ding, L. S., Guo, Y. R., Chen, F., & Tang, L. (2016). Bioactivity-guided isolation of antioxidant and anti-hepatocarcinoma constituents from Veronica ciliata. Chemistry Central Journal, 10. http://dx.doi.org/10.1186/s13065-016-0172-1
  • • Zou, L. C., Zhu, T. F., Xiang, H., Yu, L., Yan, Z. H., Gan, S. C., . . . Deng, X. M. (2008). New secoiridoid glycosides from the roots of Picrorhiza scrophulariiflora. Molecules, 13(9), 2049-2057. http://dx.doi. org/10.3390/molecules13092049/

Year 2021, Volume: 51 Issue: 3, 372 - 377, 29.12.2021

Zeynep Doğan , Yasin Genç , Şebnem Harput , Asuman Karadeniz Pekgöz , İclal Saraçoğlu

Abstract

Project Number

108T518

References

  • • Albach, D. C., Grayer, R. J., Jensen, S. R., Ozgokce, F., & Veitch, N. C. (2003). Acylated flavone glycosides from Veronica. Phytochemistry, 64(7), 1295-1301. http://dx.doi.org/10.1016/j.phytochem. 2003.08.012
  • • Albach, D. C., Jensen, S. R., Ozgokce, F., & Grayer, R. J. (2005). Veronica: Chemical characters for the support of phylogenetic relationships based on nuclear ribosomal and plastid DNA sequence data. Biochemical Systematics and Ecology, 33(11), 1087-1106. http://dx.doi.org/10.1016/j.bse.2005.06.002
  • • Baytop, T. (1999). Türkiye’de Bitkiler ile Tedavi (Geçmişte ve Bugün) (2nd ed.) [Therapy with medicinal plants in Turkey, Past and Present]. İstanbul, Turkey: Nobel Tıp Kitabevleri.
  • • Fischer, M. A. (1978). 17. Veronica L. In P.H. Davis (Ed.), Flora of Turkey and the East Aegean Islands. Volume Six (pp.489-753), Edinburgh, UK: Edinburgh University Press.
  • • Fujita, T., Sezik, E., Tabata, M., Yesilada, E., Honda, G., Tanaka, T., & Takaishi, Y. (1995). Traditional medicine in Turkey VII. Folk medicine in Middle and West Black Sea Regions. Economic Botany, 49, 406-422. http://dx.doi.org/10.1007/Bf02863092
  • • Graham, J. G., Quinn, M. L., Fabricant, D. S., & Farnsworth, N. R. (2000). Plants used against cancer - an extension of the work of Jonathan Hartwell. Journal of Ethnopharmacology, 73(3), 347-377. http://dx.doi.org/10.1016/S0378-8741(00)00341-X
  • • Harput, U. S., Genc, Y., Khan, N., & Saracoglu, I. (2011). Radical scavenging effects of different Veronica species. Records of Natural Products, 5(2), 100-107.
  • • Harput, U. S., Genc, Y., & Saracoglu, I. (2012). Cytotoxic and antioxidative activities of Plantago lagopus L. and characterization of its bioactive compounds. Food and Chemical Toxicology, 50(5), 1554- 1559. http://dx.doi.org/10.1016/j.fct.2012.01.019
  • • Harput, U. S., Karadeniz, A., Genc, Y., & Saracoglu, I. (2009). Comparative Bioactivity Studies on Four Veronica species. FABAD Journal of Pharmaceutical Science, 34, 67-72.
  • • Harput, U. S., Saracoglu, I., Inoue, M., & Ogihara, Y. (2002). Antiinflammatory and cytotoxic activities of five Veronica species. Biological & Pharmaceutical Bulletin, 25(4), 483-486. http://dx.doi. org/10.1248/bpb.25.483
  • • Jensen, S. R., Albach, D. C., Ohno, T., & Grayer, R. J. (2005). Veronica: Iridoids and cornoside as chemosystematic markers. Biochemical Systematics and Ecology, 33(10), 1031-1047. http://dx.doi. org/10.1016/j.bse.2005.03.001
  • • Jensen, S. R., Opitz, S. E. W., & Gotfredsen, C. H. (2011). A new phenylethanoid triglycoside in Veronica beccabunga L. Biochemical Systematics and Ecology, 39(3), 193-197. http://dx.doi. org/10.1016/j.bse.2011.02.008
  • • Kawada, T., Yoneda, Y., Asano, R., Kan-No, I., & Schmid, W. (2006). Synthesis of plantamajoside, a bioactive dihydroxyphenylethyl glycoside from Plantago major L. Holzforschung, 60(5), 492-497. http://dx.doi.org/10.1515/Hf.2006.081
  • • Lenherr, A., Lahloub, M.F. & Sticher, O. (1984). Three flavonoid glycosides containing acetylated allose from Stachys recta. Phytochemistry, 23(10), 2343-2345.
  • • Mosmann, T. (1983). Rapid colorimetric assay for cellular growth and survival - application to proliferation and cytotoxicity assays. Journal of Immunological Methods, 65(1-2), 55-63. http://dx.doi. org/10.1016/0022-1759(83)90303-4
  • • NCI (National Cancer Institute). (2020, May 8). Antioxidants and Cancer Prevention [online]. Retrieved from https://www.cancer.gov/ about-cancer/causes-prevention/risk/diet/antioxidants-fact-sheet • Olmstead, R. G. (2002). Whatever happened to the Scrophulariaceae? Fremontia, 30(2), 13-22.
  • • Ozipek, M., Saracoglu, I., Kojima, K., Ogihara, Y., & Calis, I. (1999). Fuhsioside, a new phenylethanoid glucoside from Veronica fuhsii. Chemical & Pharmaceutical Bulletin, 47(4), 561-562.
  • • Ravn, H., Nishibe, S., Sasahara, M., & Li, X. B. (1990). Phenolic compounds from Plantago asiatica. Phytochemistry, 29(11), 3627-3631. http://dx.doi.org/10.1016/0031-9422(90)85289-R
  • • Salehi, B., Shetty, M. S., Kumar, N. V. A., Zivkovic, J., Calina, D., Docea, A. O., . . . Sharifi-Rad, J. (2019). Veronica plants-drifting from farm to traditional healing, food application, and phytopharmacology. Molecules, 24(13). http://dx.doi.org/10.3390/molecules24132454
  • • Saracoglu, I., & Harput, U. S. (2012). In vitro cytotoxic activity and structure activity relationships of iridoid glucosides derived from Veronica species. Phytotherapy Research, 26(1), 148-152. http:// dx.doi.org/10.1002/ptr.3546
  • • Saracoglu, I., Harput, U. S., & Ogihara, Y. (2004). Acylated flavone glycosides from Veronica pectinata var. glandulosa and V. persica. Turkish Journal of Chemistry, 28(6), 751-759.
  • • Saracoglu, I., Inoue, M., Calis, I. & Ogihara, Y. 1995. Studies on constituents with cytotoxic and cytostatic activity of two Turkish medicinal plants, Phlomis armeniaca and Scutellaria salviifolia. Biological & Pharmaceutical Bulletin, 18(10), 1396-1400.
  • • Saracoglu, I., Oztunca, F. H., Nagatsu, A., & Harput, U. S. (2011). Iridoid content and biological activities of Veronica cuneifolia subsp. cuneifolia and V. cymbalaria. Pharmaceutical Biology, 49(11), 1150- 1157. http://dx.doi.org/10.3109/13880209.2011.575790
  • • Saracoglu, I., Varel, M., Harput, U. S., & Nagatsu, A. (2004). Acylated flavonoids and phenol glycosides from Veronica thymoides subsp. pseudocinerea. Phytochemistry, 65(16), 2379-2385. http://dx.doi. org/10.1016/j.phytochem.2004.05.011
  • • Taskova, R. M., Albach, D. C., & Grayer, R. J. (2004). Phylogeny of Veronica - a combination of molecular and chemical evidence. Plant Biology, 6(6), 673-682. http://dx.doi.org/10.1055/s-2004-830330
  • • Tomas-Barberan, F. A., Grayerbarkmeijer, R. J., Gil, M. I., & Harborne, J. B. (1988). Distribution of 6-hydroxyflavone, 6-methoxyflavone and 8-hydroxyflavone glycosides in the Labiatae, the Scrophulariaceae and related families. Phytochemistry, 27(8), 2631-2645. http://dx.doi.org/10.1016/0031-9422(88)87034-1
  • • Wang, C. C., Gong, X., Bo, A., Zhang, L., Zhang, M. X., Zang, E. H., . . . Li, M. H. (2020). Iridoids: Research advances in their phytochemistry, biological activities, and pharmacokinetics. Molecules, 25(2). http://dx.doi.org/10.3390/molecules25020287
  • • Xue, H. B., Chen, K. X., Zhang, L. Q., & Li, Y. M. (2019). Review of the ethnopharmacology, phytochemistry, and pharmacology of the genus Veronica. American Journal of Chinese Medicine, 47(6), 1193- 1221. http://dx.doi.org/10.1142/S0192415x19500617
  • • Yin, L., Lu, Q. X., Tan, S. C., Ding, L. S., Guo, Y. R., Chen, F., & Tang, L. (2016). Bioactivity-guided isolation of antioxidant and anti-hepatocarcinoma constituents from Veronica ciliata. Chemistry Central Journal, 10. http://dx.doi.org/10.1186/s13065-016-0172-1
  • • Zou, L. C., Zhu, T. F., Xiang, H., Yu, L., Yan, Z. H., Gan, S. C., . . . Deng, X. M. (2008). New secoiridoid glycosides from the roots of Picrorhiza scrophulariiflora. Molecules, 13(9), 2049-2057. http://dx.doi. org/10.3390/molecules13092049/
There are 30 citations in total.

Details

Primary Language English
Subjects Pharmacology and Pharmaceutical Sciences
Journal Section Original Article
Authors

Zeynep Doğan 0000-0002-0108-6040

Yasin Genç 0000-0002-5408-7565

Şebnem Harput 0000-0002-2641-3263

Asuman Karadeniz Pekgöz 0000-0002-8141-7849

İclal Saraçoğlu 0000-0002-8141-7849

Project Number 108T518
Publication Date December 29, 2021
Submission Date December 25, 2020
Published in Issue Year 2021 Volume: 51 Issue: 3

Cite

APA Doğan, Z., Genç, Y., Harput, Ş., Karadeniz Pekgöz, A., et al. (2021). Chemical profiling and cytotoxic activity of aqueous extract of Veronica peduncularis M.Bieb.: A chemotaxonomical approach. İstanbul Journal of Pharmacy, 51(3), 372-377.
AMA Doğan Z, Genç Y, Harput Ş, Karadeniz Pekgöz A, Saraçoğlu İ. Chemical profiling and cytotoxic activity of aqueous extract of Veronica peduncularis M.Bieb.: A chemotaxonomical approach. iujp. December 2021;51(3):372-377.
Chicago Doğan, Zeynep, Yasin Genç, Şebnem Harput, Asuman Karadeniz Pekgöz, and İclal Saraçoğlu. “Chemical Profiling and Cytotoxic Activity of Aqueous Extract of Veronica Peduncularis M.Bieb.: A Chemotaxonomical Approach”. İstanbul Journal of Pharmacy 51, no. 3 (December 2021): 372-77.
EndNote Doğan Z, Genç Y, Harput Ş, Karadeniz Pekgöz A, Saraçoğlu İ (December 1, 2021) Chemical profiling and cytotoxic activity of aqueous extract of Veronica peduncularis M.Bieb.: A chemotaxonomical approach. İstanbul Journal of Pharmacy 51 3 372–377.
IEEE Z. Doğan, Y. Genç, Ş. Harput, A. Karadeniz Pekgöz, and İ. Saraçoğlu, “Chemical profiling and cytotoxic activity of aqueous extract of Veronica peduncularis M.Bieb.: A chemotaxonomical approach”, iujp, vol. 51, no. 3, pp. 372–377, 2021.
ISNAD Doğan, Zeynep et al. “Chemical Profiling and Cytotoxic Activity of Aqueous Extract of Veronica Peduncularis M.Bieb.: A Chemotaxonomical Approach”. İstanbul Journal of Pharmacy 51/3 (December 2021), 372-377.
JAMA Doğan Z, Genç Y, Harput Ş, Karadeniz Pekgöz A, Saraçoğlu İ. Chemical profiling and cytotoxic activity of aqueous extract of Veronica peduncularis M.Bieb.: A chemotaxonomical approach. iujp. 2021;51:372–377.
MLA Doğan, Zeynep et al. “Chemical Profiling and Cytotoxic Activity of Aqueous Extract of Veronica Peduncularis M.Bieb.: A Chemotaxonomical Approach”. İstanbul Journal of Pharmacy, vol. 51, no. 3, 2021, pp. 372-7.
Vancouver Doğan Z, Genç Y, Harput Ş, Karadeniz Pekgöz A, Saraçoğlu İ. Chemical profiling and cytotoxic activity of aqueous extract of Veronica peduncularis M.Bieb.: A chemotaxonomical approach. iujp. 2021;51(3):372-7.
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