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: Salar Hafez Ghoran, Vahideh Atabaki, Esmaeil Babaei, Seyed Reza Olfatkhah, Michal Dusek, Vaclav Eigner, Alireza Soltani, Aliakbar Dehno Khalaji
• Journal: Bioorganic chemistry (Bioorg Chem) Vol. 66 Pg. 27-32 (06 2016) ISSN: 1090-2120 [Electronic] United States
• PMID: 26998943 (Publication Type: Journal Article)
• Copyright: Copyright © 2016 Elsevier Inc. All rights reserved.

Chemical References

• Antineoplastic Agents
• Coumarins
• Sesquiterpenes
• samarcandin

Topics

• Animals
• Antineoplastic Agents (chemistry, isolation & purification, pharmacology)
• Cell Line, Tumor
• Cell Proliferation (drug effects)
• Coumarins (chemistry, isolation & purification, pharmacology)
• Crystallography, X-Ray
• Dose-Response Relationship, Drug
• Humans
• Magnetic Resonance Spectroscopy
• Mice
• Models, Molecular
• Molecular Structure
• Quantum Theory
• Sesquiterpenes (chemistry, isolation & purification, pharmacology)
• Structure-Activity Relationship