ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Bio-activity guided isolation of 1,5-dicaffeoyl quinic acid from Cirsium species and investigation of their therapeutic potency on melanoma through in vitro and in silico approaches

Sila Ozlem Sener, Seyda Kanbolat, Merve Badem, Ufuk Ozgen, Rezzan Aliyazicioglu, Esma Ceylan, Ahmet Ceyhan Goren, Tuncay Dirmenci, Turan Arabaci, Sermet Yildirmis, Seyma Emiroglu, and Gulcin Saltan İscan

Department of Pharmacognosy, Gulhane Faculty of Pharmacy, University of Health Sciences Turkey, Ankara, Turkey

E-mail: silaozlem.sener@sbu.edu.tr

Received: 12 September 2024  Accepted: 6 May 2025

Abstract:

Melanoma exhibits a high fatality rate, and its characteristic of rapid proliferation is progressively increasing. Collagenase inhibitors are pivotal in influencing the invasion of cancer cells in melanoma. The objective of this research is to explore the therapeutic impact of specific Cirsium species on melanoma. A bioactivity-guided fractionation was carried out to identify the effective compound using collagenase inhibitory efficacy. The most potent compound underwent additional examination through in silico methods, and the presence of this compound, along with several phenolic compounds, in the most effective Cirsium species was identified using LC–MS/MS analysis. The cytotoxic effect on SK-Mel cells was assessed using the in vitro MTT technique. The bioactivity-guided fractionation study led to the identification of CTR-E1 from Cirsium trachylepis’s root (CTR), and its structure was determined as 1,5-dicaffeoylquinic acid. In silico analysis revealed that 1,5-dicaffeoylquinic acid exhibited significant potency with a maximum binding affinity of − 8.19 kcal/mol, as well as hydrogen bonds and hydrophobic interactions. 1,5-dicaffeoylquinic acid, fumaric acid, pyrogallol, and epicatechin were detected and quantified in CTR by LC–MS/MS analysis. CTR was found to be effective on SK-Mel cells. Further clinical and toxicological studies, as well as additional in vitro and in vivo studies, are necessary to support the therapeutic efficacy of CTR and 1,5-dicaffeoylquinic acid.

Keywords: 1,5-dicaffeoylquinic acid; Bio-activity-guided fractionation; Cirsium; Collagenase; In silico; LC–MS/MS; Melanoma

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-025-04149-7

Chemical Papers 79 (9) 5733–5746 (2025)