Bio-guided isolation of Centaurea bruguierana subsp. belangerana cytotoxic components

Abstract Centaurea bruguierana subsp. belangerana was extracted by 80% ethanol. The total extract was then partitioned into four fractions including chloroform, ethyl acetate and methanol. Cytotoxic effect of fractions was examined by MTT assay in K562 (chronic myelogenous leukemia), AGS (gastric adenocarcinoma), MCF-7 (breast adenocarcinoma) and SW742 (colon adenocarcinoma) cell lines. The Chloroform fraction, with the lowest LC50 against K-562 cell lines, was partitioned into 14 subfractions and subjected to further purification by reversed-phase (C18) silica gel and sephadex LH-20 column chromatography. Three flavonoids including cirsimaritin, cirsilinelol and eupatilin were isolated for the first time from the species and the structures were confirmed by spectroscopic data. The high selectivity index of the purified flavonoids indicates valuable components with potential few side effects for normal cell lines. However, solubility tests for isolated components indicates the need for novel pharmaceutical dosage forms, in the case for using natural flavonoids as chemotherapeutic agents.

[1]  M. Iranshahi,et al.  Screening of several biological activities induced by different sesquiterpene lactones isolated from Centaurea behen L. and Rhaponticum repens (L.) Hidalgo , 2018, Natural product research.

[2]  D. Hadjipavlou-Litina,et al.  Lignans and indole alkaloids from the seeds of Centaurea vlachorum Hartvig (Asteraceae), growing wild in Albania and their biological activity , 2017, Natural product research.

[3]  S. Ostad,et al.  Cytotoxic Potential of Centaurea bruguierana ssp. belangerana: The MTT Assay. , 2016, Acta medica Iranica.

[4]  S. Ostad,et al.  COMPARISON OF CYTOTOXIC ACTIVITY OF SOME IRANIAN STACHYS SPP. EXTRACTS ON DIFFERENT CANCER CELL LINES , 2014 .

[5]  M. Khairuddean,et al.  Chemical Constituents and Antioxidant Activity of Teucrium barbeyanum Aschers , 2014 .

[6]  F. Estévez,et al.  Cytotoxic sesquiterpene lactones and other constituents of Centaurea omphalotricha , 2012 .

[7]  M. Sharifzadeh,et al.  Pharmacological and histological effects of Centaurea bruguierana ssp. belangerana on indomethacin-induced peptic ulcer in rats , 2012, Journal of Natural Medicines.

[8]  S. Ostad,et al.  Investigation on Cytotoxic activity of Centaurea bruguierana ssp. belangerana , 2009 .

[9]  Y. Kang,et al.  Eupatilin, isolated from Artemisia princeps Pampanini, enhances hepatic glucose metabolism and pancreatic beta-cell function in type 2 diabetic mice. , 2008, Diabetes research and clinical practice.

[10]  L. Nahar,et al.  Bioactivity of two Turkish endemic Centaurea species, and their major constituents , 2007 .

[11]  F. Benayache,et al.  Sesquiterpene lactones from Centaurea musimomum. Antiplasmodial and cytotoxic activities. , 2005, Fitoterapia.

[12]  L. Nahar,et al.  Isolation, structure elucidation and bioactivity of schischkiniin, a unique indole alkaloid from the seeds of Centaurea schischkinii , 2005 .

[13]  Costas Demetzos,et al.  Sesquiterpene lactones from Centaurea spinosa and their antibacterial and cytotoxic activities. , 2005, Journal of natural products.

[14]  Do-Hee Kim,et al.  Eupatilin inhibits proliferation of ras-transformed human breast epithelial (MCF-10A-ras) cells. , 2005, Journal of environmental pathology, toxicology and oncology : official organ of the International Society for Environmental Toxicology and Cancer.

[15]  Min-Jung Kim,et al.  Eupatilin, a pharmacologically active flavone derived from Artemisia plants, induces apoptosis in human gastric cancer (AGS) cells. , 2005, Journal of environmental pathology, toxicology and oncology : official organ of the International Society for Environmental Toxicology and Cancer.

[16]  S. Sarker,et al.  Epoxylignans from the seeds of Centaurea cyanus (Asteraceae) , 2004 .

[17]  Do-Hee Kim,et al.  Eupatilin, a pharmacologically active flavone derived from Artemisia plants, induces cell cycle arrest in ras-transformed human mammary epithelial cells. , 2004, Biochemical pharmacology.

[18]  A. Delazar,et al.  Bioactive lignans from the seeds of Centaurea macrocephala , 2004 .

[19]  L. Walker,et al.  Cytotoxic sesquiterpene lactones from Centaurothamnus maximus and Vicoa pentanema , 2003, Phytotherapy research : PTR.

[20]  C. Demetzos,et al.  Bioactive sesquiterpene lactones from Centaurea species and their cytotoxic/cytostatic activity against human cell lines in vitro. , 2002, Planta medica.

[21]  Y. Surh,et al.  Eupatilin, a pharmacologically active flavone derived from Artemisia plants, induces apoptosis in human promyelocytic leukemia cells. , 2001, Mutation research.

[22]  S. Sarker,et al.  Indole alkaloids from the seeds of Centaurea cyanus (Asteraceae). , 2001, Phytochemistry.

[23]  D. Youssef.  Sesquiterpene lactones of Centaurea scoparia. , 1998, Phytochemistry.

[24]  S. Sarker,et al.  Moschamide: An Unusual Alkaloid from the Seeds of Centaurea moschata. , 1998 .