3,5,7-Trimethoxyphenanthrene-1,4-dione: a new biologically relevant natural phenanthrenequinone derivative from Dioscorea prazeriand studies on its single X-ray crystallographic behavior, molecular docking and other physico-chemical properties

A naturally occurring new phenanthrenequinone derivative has been isolated from the yams of Dioscorea prazeriPrain and Burkil (Dioscoreaceae) and identified as 3,5,7-trimethoxyphenanthrene-1,4-dione (1) on the basis of its detailed spectral and single crystal X-ray analyses. The compound crystallize...

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Bibliographic Details
Published in:RSC advances 2016-01, Vol.6 (9), p.7317-7329
Main Authors: Brahmachari, Goutam, Das, Saktipada, Biswas (Sinha), Maya, Kumar, Abhishek, Srivastava, Ambrish Kumar, Misra, Neeraj
Format: Article
Language:English
Subjects:
Derivatives
Docking
Least squares method
Molecular orbitals
Single crystals
Spectra
Vibrational spectra
X-rays
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Summary:A naturally occurring new phenanthrenequinone derivative has been isolated from the yams of Dioscorea prazeriPrain and Burkil (Dioscoreaceae) and identified as 3,5,7-trimethoxyphenanthrene-1,4-dione (1) on the basis of its detailed spectral and single crystal X-ray analyses. The compound crystallizes in the triclinic space group P1&cmb.macr; with the following unit-cell parameters: a= 7.7045(3), b= 8.5088(4), c= 16.3254(7) Aa, alpha = 98.908(2) degree , beta = 96.316(2) degree , gamma = 103.939(2) degree and Z= 2. The crystal structure was solved by direct methods using single-crystal X-ray diffraction data collected at room temperature and refined by full-matrix least-squares procedures to a final R-value of 0.0559 for 2832 observed reflections. Exhaustive theoretical studies on the molecular structure, vibrational spectra, HOMO, LUMO, MESP surfaces, reactivity descriptor and molecular docking of this plant-derived hitherto unknown natural molecule have also been performed. The equilibrium geometry of the title compound has been obtained and analyzed using the DFT-B3LYP/6-31+G(d,p) method. A comparison between the calculated vibrational spectral data with the experimental observations for the phenanthrenequinone molecule has been performed. The reactivity of this molecule is explained using various local as well as global molecular descriptors and reactivity surfaces have also been analyzed. The molecular docking study of the title molecule for predicting its possible anticancer property has also been investigated.
ISSN:2046-2069
DOI:10.1039/c5ra21490d