Isolation, spectroscopic and density functional theory studies of 7-(4-methoxyphenyl)-9H-furo[2,3-f]chromen-9-one: a new flavonoid from the bark of Millettia ovalifolia

Taj Ur Rahman; Mohammad Arfan; Tariq Mahmood; Wajiha Liaqat; Mazhar Amjad Gilani; Ghias Uddin; Ralf Ludwig; Khair Zaman; M Iqbal Choudhary; Khanzadi Fatima Khattak; Khurshid Ayub

doi:10.1016/j.saa.2015.03.061

Isolation, spectroscopic and density functional theory studies of 7-(4-methoxyphenyl)-9H-furo[2,3-f]chromen-9-one: a new flavonoid from the bark of Millettia ovalifolia

Spectrochim Acta A Mol Biomol Spectrosc. 2015 Jul 5:146:24-32. doi: 10.1016/j.saa.2015.03.061. Epub 2015 Mar 9.

Authors

Affiliations

¹ Department of Chemistry, Abdul Wali Khan University, Mardan, Pakistan; Institute of Chemical Sciences, University of Peshwar-25120, Pakistan. Electronic address: taj_urrehman81@yahoo.co.uk.
² Institute of Chemical Sciences, University of Peshwar-25120, Pakistan.
³ Department of Chemistry, COMSATS Institute of Information Technology, Abbottabad 22060, Pakistan.
⁴ Department of Chemical Engineering, COMSATS Institute of Information Technology, Lahore, Pakistan.
⁵ Institut für Chemie, Physikalische und Theoretische Chemie, Universität Rostock, Dr.-Lorenz-Weg 1, 18059 Rostock, Germany; Leibniz-Institut für Katalyse an der Universität Rostock e. V. Alebert-Einstein-Strasse 29a, 18059 Rostock, Germany.
⁶ Department of Chemistry, Abdul Wali Khan University, Mardan, Pakistan.
⁷ International Center for Chemical and Biological Sciences, H.E.J. Research Institute of Chemistry, University of Karachi, Karachi 75270, Pakistan.
⁸ Department of Chemistry, COMSATS Institute of Information Technology, Abbottabad 22060, Pakistan; Department of Chemistry, College of Science, King Faisal University, Al Ahsa 31982, Saudi Arabia. Electronic address: khurshid@ciit.net.pk.

PMID: 25804510
DOI: 10.1016/j.saa.2015.03.061

Abstract

The phytochemical examination of chloroform soluble fraction (FX2) of methanolic extract of bark of Millettia ovalifolia yielded a new flavonoid; 7-(4-methoxyphenyl)-9H-furo [2,3-f]chromen-9-one (1). Compound 1 is characterized by spectroscopic analytical techniques such as UV, IR, 1D, 2D NMR spectroscopy, and mass spectrometry. A theoretical model is also developed for obtaining geometric, electronic and spectroscopic properties of 1. The geometry optimization and harmonic vibration simulations have been carried out at B3LYP/6-31G(d,p). The vibrational spectrum of compound 1 shows nice correlation with the experimental IR spectrum, through a scaling factor of 0.9613. (1)H and (13)C NMR chemical shifts are simulated using Cramer's re-parameterized function WP04 at 6-31G(d,p) basis set, and correlate nicely with the experimental chemical shifts.

Keywords: B3LYP/6-31G(d,p); Density functional theory; IR; Millettia ovalifolia bark; New flavonoid; TD-DFT.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Flavonoids / chemistry*
Flavonoids / isolation & purification*
Magnetic Resonance Spectroscopy
Molecular Structure
Plant Bark / chemistry*
Trees / chemistry*

Substances

Flavonoids