Further sesquiterpenoids and phenolics from two species of Taraxacum F.H. Wigg. and cytotoxic activity of taraxinic acid and its derivatives

Klaudia Michalska , Agnieszka Galanty , Oskar Michalski , Anna Stojakowska

Abstract

From roots of Taraxacum flavostylum and Taraxacum lucidum, the species included in the section Taraxacum F. H. Wigg. of the genus Taraxacum F. H. Wigg., eight sesquiterpene lactones, including taraxinic acid (1) and 11β,13-dihydrotaraxinic acid (2), taraxinic acid β-glucopyranosyl ester (3) and its 11β,13-dihydroderivative (4), ainslioside (5), deacetylmatricarin (6), 3-epi-11β,13-dihydrodeacylcynaropicrin (7) and ixerin D (8) together with six phenolic metabolites (9‒14) were isolated. 3-Epi-11β,13-dihydrodeacylcynaropicrin (7), 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (9) and 5-methoxy-eugenyl-4-O-β-glucopyranoside (11) were found for the first time in Taraxacum spp. Compounds 1‒14 were isolated from T. flavostylum roots, whereas only three germacranolides (3‒5), a guaianolide (8) and dihydrosyringin (13) were present in the extract from T. lucidum. Structures of the compounds were elucidated based on spectroscopic data. In vitro cytotoxic activity of taraxinic acid (1) and its derivatives (2‒4) against three human melanoma cell lines (A375, HTB140 and WM793), human normal keratinocytes (HaCaT), human normal prostate epithelial cells (PNT-2), and human prostate carcinoma cell line (DU145) was also examined in this study.
Author Klaudia Michalska
Klaudia Michalska,,
-
, Agnieszka Galanty - [Uniwersytet Jagielloński Collegium Medicum]
Agnieszka Galanty,,
-
- Uniwersytet Jagielloński Collegium Medicum
, Oskar Michalski (FoFT / DoCh)
Oskar Michalski,,
- Department of Chemistry
, Anna Stojakowska
Anna Stojakowska,,
-
Journal seriesPhytochemistry Letters, ISSN 1874-3900, e-ISSN 1876-7486, (N/A 70 pkt)
Issue year2019
Vol30
Pages296-301
Publication size in sheets0.5
Keywords in EnglishAsteraceae, Taraxacum flavostylum, Taraxacum lucidum, Sesquiterpene lactones, Phenolic compounds, Cytotoxic activity
ASJC Classification1102 Agronomy and Crop Science; 1110 Plant Science; 1303 Biochemistry; 1305 Biotechnology
DOIDOI:10.1016/j.phytol.2019.02.010
URL https://www.sciencedirect.com/science/article/pii/S1874390018305962
Languageen angielski
Score (nominal)70
Score sourcejournalList
Publication indicators WoS Citations = 1; Scopus SNIP (Source Normalised Impact per Paper): 2017 = 0.922; WoS Impact Factor: 2018 = 1.338 (2) - 2018=1.506 (5)
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