Isolation of trachelogenin 4-O-β-D-glucoside from the fruits of Carthamus tinctorius L.

Authors

  • Andrzej Patyra Department of Pharmacognosy and Molecular Basis of Phytotherapy, Medical University of Warsaw, Warsaw, Poland; Doctoral School, Medical University of Warsaw, Warsaw, Poland; Institut des Biomolécules Max Mousseron, Université de Montpellier, CNRS, ENSCM, Montpellier, France https://orcid.org/0000-0003-4981-6660
  • Marcin Kołakowski Department of Pharmacognosy and Molecular Basis of Phytotherapy, Medical University of Warsaw, Warsaw, Poland
  • Marta Katarzyna Dudek Structural Studies Department, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Łódź, Poland
  • Anna Karolina Kiss Department of Pharmacognosy and Molecular Basis of Phytotherapy, Medical University of Warsaw, Warsaw, Poland

DOI:

https://doi.org/10.56782/pps.39

Keywords:

Carthamus tinctorius, lignans, isolation, tracheloside, trachelogenin

Abstract

Trachelogenin 4-O-β-D-glucoside or tracheloside is a rare lignan glycoside present mostly in some plants from the Cynarae tribe of the Asteraceae family. As this lignan is also present in small amounts in the human diet, isolation and study of the pharmacological properties of this compound may bring some new insights into the role of lignans. This study aimed to isolate trachelogenin 4-O-β-D-glucoside from the fruits of safflower using chromatographic methods. Briefly, 339 mg of tracheloside was isolated from 500 g of plant material. The yield is sufficient for performing biological studies, thus confirming that safflower fruits are a significant source of this rare compound.

Downloads

Download data is not yet available.

References

Asgarpanah, J.; Kazemivash, N. Phytochemistry, pharmacology and medicinal properties of Carthamus tinctorius L. Chin J Integr Med 2013, 19, 153-159, doi:10.1007/s11655-013-1354-5. DOI: https://doi.org/10.1007/s11655-013-1354-5

Delshad, E.; Yousefi, M.; Sasannezhad, P.; Rakhshandeh, H.; Ayati, Z. Medical uses of Carthamus tinctorius L. (Safflower): a comprehensive review from Traditional Medicine to Modern Medicine. Electron Physician 2018, 10, 6672-6681, doi:10.19082/6672. DOI: https://doi.org/10.19082/6672

Zhang, L.L.; Tian, K.; Tang, Z.H.; Chen, X.J.; Bian, Z.X.; Wang, Y.T.; Lu, J.J. Phytochemistry and Pharmacology of Carthamus tinctorius L. Am J Chin Med 2016, 44, 197-226, doi:10.1142/s0192415x16500130. DOI: https://doi.org/10.1142/S0192415X16500130

Zafari, M.; Ebadi, A.; Jahanbakhsh, S.; Sedghi, M. Safflower (Carthamus tinctorius) Biochemical Properties, Yield, and Oil Con-tent Affected by 24-Epibrassinosteroid and Genotype under Drought Stress. J Agric Food Chem 2020, 68, 6040-6047, doi:10.1021/acs.jafc.9b06860. DOI: https://doi.org/10.1021/acs.jafc.9b06860

Zalesak, F.; Bon, D.J.D.; Pospisil, J. Lignans and Neolignans: Plant secondary metabolites as a reservoir of biologically active substances. Pharmacol Res 2019, 146, 104284, doi:10.1016/j.phrs.2019.104284. DOI: https://doi.org/10.1016/j.phrs.2019.104284

Qian, X.J.; Jin, Y.S.; Chen, H.S.; Xu, Q.Q.; Ren, H.; Zhu, S.Y.; Tang, H.L.; Wang, Y.; Zhao, P.; Qi, Z.T.; et al. Trachelogenin, a novel inhibitor of hepatitis C virus entry through CD81. J Gen Virol 2016, 97, 1134-1144, doi:10.1099/jgv.0.000432. DOI: https://doi.org/10.1099/jgv.0.000432

Moura, A.F.; Lima, K.S.B.; Sousa, T.S.; Marinho-Filho, J.D.B.; Pessoa, C.; Silveira, E.R.; Pessoa, O.D.L.; Costa-Lotufo, L.V.; Moraes, M.O.; Araújo, A.J. In vitro antitumor effect of a lignan isolated from Combretum fruticosum, trachelogenin, in HCT-116 human colon cancer cells. Toxicol In Vitro 2018, 47, 129-136, doi:10.1016/j.tiv.2017.11.014. DOI: https://doi.org/10.1016/j.tiv.2017.11.014

Yoo, H.H.; Park, J.H.; Kwon, S.W. An anti-estrogenic lignan glycoside, tracheloside, from seeds of Carthamus tinctorius. Biosci Biotechnol Biochem 2006, 70, 2783-2785, doi:10.1271/bbb.60290. DOI: https://doi.org/10.1271/bbb.60290

Jo, A.r.; Han, H.-s.; Seo, S.; Shin, J.-S.; Lee, J.Y.; Kim, H.J.; Lee, K.-T. Inhibitory effect of moschamine isolated from Carthamus tinctorius on LPS-induced inflammatory mediators via AP-1 and STAT1/3 inactivation in RAW 264.7 macrophages. Bioorganic & Me-dicinal Chemistry Letters 2017, 27, 5245-5251, doi:https://doi.org/10.1016/j.bmcl.2017.10.035. DOI: https://doi.org/10.1016/j.bmcl.2017.10.035

Tan, X.Q.; Chen, H.S.; Liu, R.H.; Tan, C.H.; Xu, C.L.; Xuan, W.D.; Zhang, W.D. Lignans from Trachelospermum jasminoides. Planta Med 2005, 71, 93-95, doi:10.1055/s-2005-837761. DOI: https://doi.org/10.1055/s-2005-837761

Boldizsár, I.; Kraszni, M.; Tóth, F.; Noszál, B.; Molnár-Perl, I. Complementary fragmentation pattern analysis by gas chromatog-raphy-mass spectrometry and liquid chromatography tandem mass spectrometry confirmed the precious lignan content of Cirsium weeds. J Chromatogr A 2010, 1217, 6281-6289, doi:10.1016/j.chroma.2010.08.018. DOI: https://doi.org/10.1016/j.chroma.2010.08.018

Graikou, K.; Kourti, P.M.; Zengin, G.; Gortzi, O.; Danalatos, N.; Chinou, I. Chemical Characterisation-Biological Evaluation of Greek Cultivar Cardoon Seeds (Cynara cardunculus). A By-product with Potential High Added Value. Planta Med 2021, 87, 1025-1031, doi:10.1055/a-1472-6336. DOI: https://doi.org/10.1055/a-1472-6336

Kuehnl, S.; Schroecksnadel, S.; Temml, V.; Gostner, J.M.; Schennach, H.; Schuster, D.; Schwaiger, S.; Rollinger, J.M.; Fuchs, D.; Stuppner, H. Lignans from Carthamus tinctorius suppress tryptophan breakdown via indoleamine 2,3-dioxygenase. Phytomedicine 2013, 20, 1190-1195, doi:10.1016/j.phymed.2013.06.006. DOI: https://doi.org/10.1016/j.phymed.2013.06.006

Szokol-Borsodi, L.; Sólyomváry, A.; Molnár-Perl, I.; Boldizsár, I. Optimum yields of dibenzylbutyrolactone-type lignans from Cynareae fruits, during their ripening, germination and enzymatic hydrolysis processes, determined by on-line chromatographic methods. Phytochem Anal 2012, 23, 598-603, doi:10.1002/pca.2360. DOI: https://doi.org/10.1002/pca.2360

Downloads

Published

2022-08-18

Issue

Section

Articles

How to Cite

Isolation of trachelogenin 4-O-β-D-glucoside from the fruits of Carthamus tinctorius L. (2022). Prospects in Pharmaceutical Sciences, 20(2), 24-30. https://doi.org/10.56782/pps.39