title: Isolation, spectroscopic characterization, X-ray, theoretical studies as well as in vitro cytotoxicity of Samarcandin.
abstract: Samarcandin 1, a natural sesquiterpene-coumarin, was isolated as well as elucidated from F. assa-foetida which has significant effect in Iranian traditional medicine because of its medicinal attitudes. The crystal structure of samarcandin was determined by single-crystal X-ray structure analysis. It is orthorhombic, with unit cell parameters a=10.8204 (5)Å, b=12.9894 (7)Å, c=15.2467 (9)Å, V=2142.9 (2)Å(3), space group P212121 and four symmetry equivalent molecules in the unit cell. Samarcandin was isolated in order to study for its theoretical studies as well as its cellular toxicity as anti-cancer drug against two cancerous cells. In comparison with controls, our microscopic and MTT assay data showed that samarcandin suppresses cancer cell proliferation in a dose-dependent manner with IC50=11μM and 13 for AGS and WEHI-164 cell lines, respectively. Density functional theory (DFT) and time-dependent density functional theory (TD-DFT) of the structure was computed by three functional methods and 6-311++G(∗∗) standard basis set. The optimized molecular geometry and theoretical analysis agree closely to that obtained from the single crystal X-ray crystallography. To sum up, the good correlations between experimental and theoretical studies by UV, NMR, and IR spectra were found.
authors.affiliation: Young Researchers and Elite Club, Maragheh Branch, Islamic Azad University, Maragheh, Iran. Electronic address: S_Hafezghoran@yahoo.com.
authors.forename: Salar Hafez
authors.initials: SH
authors.lastname: Ghoran
authors.affiliation: Department of Chemistry, Faculty of Sciences, Golestan University, Gorgan, Iran.
authors.forename: Vahideh
authors.initials: V
authors.lastname: Atabaki
authors.affiliation: Department of Animal Biology, School of Natural Sciences, University of Tabriz, Tabriz, Iran.
authors.forename: Esmaeil
authors.initials: E
authors.lastname: Babaei
authors.affiliation: Young Researchers and Elite Club, Maragheh Branch, Islamic Azad University, Maragheh, Iran.
authors.forename: Seyed Reza
authors.initials: SR
authors.lastname: Olfatkhah
authors.affiliation: Institute of Physics AS CR, v.v.i., Na Slovance 2, 182 21 Prague 8, Czech Republic.
authors.forename: Michal
authors.initials: M
authors.lastname: Dusek
authors.affiliation: Institute of Physics AS CR, v.v.i., Na Slovance 2, 182 21 Prague 8, Czech Republic.
authors.forename: Vaclav
authors.initials: V
authors.lastname: Eigner
authors.affiliation: Joints, Bones and Connective Tissue Research Centre, Golestan University of Medical Science, Gorgan, Iran.
authors.forename: Alireza
authors.initials: A
authors.lastname: Soltani
authors.affiliation: Department of Chemistry, Faculty of Sciences, Golestan University, Gorgan, Iran. Electronic address: Alidkhalaji@yahoo.com.
authors.forename: Aliakbar Dehno
authors.initials: AD
authors.lastname: Khalaji
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D003374:Coumarins / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D004305:Dose-Response Relationship, Drug; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008958:Models, Molecular; D015394:Molecular Structure; D011789:Quantum Theory; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D003374:Coumarins; D012717:Sesquiterpenes; C000609680:samarcandin
keywords: Cytotoxicity; NMR; Sesquiterpene coumarin; TD-DFT; Theoretical study; X-ray