Publication: Centaurea saligna (K. Koch) wagenitz bitkisinden antiproliferatif aktivite yönlendirmeli etken madde izolasyonu
Abstract
Amaç: Bu çalışmada, Centaurea saligna (K.Koch) Wagenitz (Asteraceae) bitkisinden antiproliferatif aktivite yönlendirmeli aktif bileşiklerin izolasyonu ve yapılarının tayini amaçlanmıştır. Gereç ve Yöntem: C. saligna bitkisinin kloroform fraksiyonundan sitotoksik etkili bileşikleri saflaştırmak için kolon kromatografisi ve preparatif ince tabaka kromatografisi kullanılmıştır. Saflaştırılan bileşiklerin yapıları NMR ve APT spektroskopisi yöntemleriyle aydınlatılmıştır. Fraksiyonların sitotoksik aktiviteleri HT29, MCF-7, HeLa, A549 ve PC3 hücre hatlarında MTT yöntemiyle incelenmiştir. Bulgular: C. saligna bitkisinin kloroform fraksiyonundan 3 tanesi flavonoit (öpatorin, 3ʹ-O-metilöpatorin, viskozin), 5 tanesi lignan (arktigenin, lappaol B, konikaol A, dihidrodehidrodikoniferil alkol, matairesinozit), 8 tanesi seskiterpen lakton (liniklorin B, aguerin B, desaçilaguerin A, sinaropikrin, (2ʹS)-17,18-dihidroksi-aguerin A, 4β,15-dihidro-3-dehidrosolstitialin A, sinarinin A, sinaratriol) 2 tanesi fenolik bileşik (p-hidroksi benzoik asit, (S)-metoksi-(3ʹ,5ʹ-dimetoksi-4ʹ- hidroksifenil) etandiol) olmak üzere toplam 18 adet bileşik izole edilmiştir. İzole edilen bu bileşiklerden Liniklorin B, Sinaropikrin ve Sinarinin A maddeleri orta derecede, Aguerin B ise seçici güçlü aktivite göstermiştir. Sonuç: C. saligna türünün antiproliferatif aktivite gösteren kloroform fraksiyonunun sorumlu bileşikleri ilk kez bu çalışmayla bulunmuştur. Lappaol B, Konikaol A ve (S)-metoksi-(3ʹ,5ʹ-dimetoksi-4ʹ-hidroksifenil)etandiol bileşikleri Centaurea cinsinden ilk kez bu çalışmayla izole edilmiştir. Liniklorin B, Lappaol B, Konikaol A ve 4β,15-dihidro-3-dehidrosolstitialin A bileşiklerinin antikanser aktivitelerine ilk defa bu çalışmayla bakılmıştır.
Objective: In this study, it was aimed to isolate antiproliferative activity-guided active compounds and determine their structures from Centaurea saligna (K.Koch) Wagenitz (Asteraceae). Materials and Methods: Column chromatography and preparative thin layer chromatography were used to purify cytotoxic compounds from the chloroform fraction of C. saligna. The structures of the purified compounds were elucidated by NMR and APT spectroscopy methods. The cytotoxic activities of the extracts were investigated by MTT method on HT-29, MCF-7, HeLa, A549 and PC-3 cell lines. Results: A total of 18 compounds, including 3 flavonoids (eupatorin, 3ʹ-O-methyleupatorin, viscosine), 5 lignans (arctigenin, lappaol B, conicaol A, dihydrodehydrodiconiferyl alcohol, matairesinoside), 8 sesquiterpene lactones (linichlorin B, aguerin B, desacylaguerin A, cynaropicrin, (2ʹS)-17,18-dihydroxy-aguerin A, 4β,15-dihydro-3-dehydrosolstitialin A, cynarinin A, cynaratriol), and 2 phenolic compounds (p-hydroxy benzoic acid, (S)-methoxy-(3ʹ,5ʹ-dimethoxy-4ʹ- hydroxyphenyl) ethanediol), were isolated from the chloroform fraction of C. saligna. Among these isolated compounds, Linichlorin B, Cynaropicrin and Cynarinin A showed moderate activity, while Aguerin B showed strong activity. Conclusion: Responsible compounds of the chloroform fraction of C. saligna species showing antiproliferative activity were found for the first time in this study. At the same time, Lappaol B, Conicaol A and (S)-methoxy-(3ʹ,5ʹ-dimethoxy-4ʹ- hydroxyphenyl) ethanediol compounds were isolated from the genus Centaurea for the first time in this study. The anticancer activities of linichlorin B, Lappaol B, Conicaol A and 4β,15-dihydro-3-dehydrosolstitialin A compounds were investigated for the first time in this study.
Objective: In this study, it was aimed to isolate antiproliferative activity-guided active compounds and determine their structures from Centaurea saligna (K.Koch) Wagenitz (Asteraceae). Materials and Methods: Column chromatography and preparative thin layer chromatography were used to purify cytotoxic compounds from the chloroform fraction of C. saligna. The structures of the purified compounds were elucidated by NMR and APT spectroscopy methods. The cytotoxic activities of the extracts were investigated by MTT method on HT-29, MCF-7, HeLa, A549 and PC-3 cell lines. Results: A total of 18 compounds, including 3 flavonoids (eupatorin, 3ʹ-O-methyleupatorin, viscosine), 5 lignans (arctigenin, lappaol B, conicaol A, dihydrodehydrodiconiferyl alcohol, matairesinoside), 8 sesquiterpene lactones (linichlorin B, aguerin B, desacylaguerin A, cynaropicrin, (2ʹS)-17,18-dihydroxy-aguerin A, 4β,15-dihydro-3-dehydrosolstitialin A, cynarinin A, cynaratriol), and 2 phenolic compounds (p-hydroxy benzoic acid, (S)-methoxy-(3ʹ,5ʹ-dimethoxy-4ʹ- hydroxyphenyl) ethanediol), were isolated from the chloroform fraction of C. saligna. Among these isolated compounds, Linichlorin B, Cynaropicrin and Cynarinin A showed moderate activity, while Aguerin B showed strong activity. Conclusion: Responsible compounds of the chloroform fraction of C. saligna species showing antiproliferative activity were found for the first time in this study. At the same time, Lappaol B, Conicaol A and (S)-methoxy-(3ʹ,5ʹ-dimethoxy-4ʹ- hydroxyphenyl) ethanediol compounds were isolated from the genus Centaurea for the first time in this study. The anticancer activities of linichlorin B, Lappaol B, Conicaol A and 4β,15-dihydro-3-dehydrosolstitialin A compounds were investigated for the first time in this study.