Two new compounds from endemic Centaurea paphlagonica (Bornm.) Wagenitz and their cytotoxic activities

• Published in: Chemical biology & drug design 2024-01, Vol.103 (1), p.e14409-n/a
• Main Authors: Tüfekçi, Ali Rıza, Demirtaş, İbrahim, Akşit, Hüseyin, Arslan, Şevki, Kocabıyık, Kübra, Zeybek, Sibel, Ozen, Tevfik, Köksal, Ekrem
• Format: Article
• Language: English
• Subjects: Antineoplastic Agents - chemistry; antiproliferative activity; Asteraceae; Caco-2 Cells; Centaurea - chemistry; Centaurea paphlagonica; Chlorogenic Acid; HEK293 Cells; Humans; isolation; Methyl Ethers; MTT; Plant Extracts - chemistry; Plant Extracts - pharmacology
• ISSN: 1747-0277; 1747-0285
• DOI: 10.1111/cbdd.14409

Centaurea paphlagonica (Bornm.) Wagenitz is an endemic plant in Turkey. Pyrocatechol, vanillic acid, 3,4‐dihydroxy benzoic acid, 5‐O‐caffeoylshikimic acid, tamarixetin, chlorogenic acid methyl ester, quercetin, 1,3‐dicaffeoylquinic acid, tamarixetin‐7‐O‐β‐D‐glucopyranoside, quercimetrin, daucosterin, paphlagonicanin B, tamarixetin‐7‐O‐β‐rutinoside, rutin, chlorogenic acid, isoorientin, orientin, 3‐O‐feruloylquinic acid, quercetagetin‐3‐methyl ether 6‐O‐β‐glucopyranoside, diosmetin 6‐C‐β‐glucopyranoside, quercetagetin 4′‐methyl ether 7‐O‐β‐glucopyranoside, paphlagonicanin A, nepetin, cirsiliol, desacylcynaropicrin, and 8α‐O‐(2′,3′‐dihydroxyisobutyryl) desacylcynaropicrin were isolated from both flower and aerial parts of C. paphlagonica. These compounds were identified using 1D and 2D NMR methods and ESI‐MS. The MTT assay assessed the antiproliferative activities of all isolated (known and new compounds) compounds on Caco‐2, LNCaP, A549, HeLa, and HEK‐293 cell lines. The 8α‐O‐(2′,3′‐dihydroxyisobutyryl) desacylcynaropicrin demonstrated the highest activity against CaCo‐2 and HeLa cancer cell lines. An undescribed pyrrole alkaloid, Paphlagonicanin B and an undescribed flavonoid glycoside, Paphlagonicanin A. The most cytotoxic compound is 8α‐O‐(2′,3′‐dihydroxyisobutyryl) desacylcynaropicrin.