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Single Crystal X-Ray Diffraction in Structure Elucidation of Arborinine from Glycosmis pentaphylla

[ Vol. 7 , Issue. 3 ]

Author(s):

Moon Moon Das, Dibakar Chandra Deka and Ranjit Thakuria   Pages 224 - 230 ( 7 )

Abstract:


Background: Arborinine is a naturally found alkaloid with various biological activities. It has been isolated from the leaf extract of Glycosmis pentaphylla, a traditionally used medicinal plant of North East of India. Single crystal X-ray diffraction on arborinine has never been reported earlier.

Objective: The main objective of the present study is to report the isolation and characterization of arborinine and its single crystal X-ray diffraction analysis.

Method: Arborinine was isolated from the leaf extract of Glycosmis pentaphylla by repeated column chromatography. Fine yellow needle-shaped crystals were recovered from a solution of purified arborinine in a mixture of ethyl acetate and petroleum ether (1:5). The purified compound is characterized by IR, NMR, HRMS and single crystal X-ray diffraction.

Results: The crystal structure was solved in orthorhombic Pbca space group with unit cell parameters a = 14.805(3) Å, b = 7.5342(15) Å, c = 23.620(5) Å, α= 90º, β = 90º, γ= 90º, V= 2634.7(9) Ǻ3, Ζ = 8, Dcalc = 1.438 Μgm-3 and F (000) = 1200. The molecules of arborinine with a planar acridine ring with flanking methoxy groups at 2- and 3- position display a 3D framework resulting from weak C-H•••O, π-π stacking and Van der Waal interactions.

Conclusion: Single crystal X-ray diffraction on arborinine is reported for the first time. High field NMR and high resolution mass are also reported for the first time on a sample of arborinine isolated from the plant Glycosmis pentaphylla.

Keywords:

Arborinine, Glycosmis pentaphylla, single crystal X-ray diffraction, column chromatography, Van der Waal interactions, Rutaceae.

Affiliation:

Department of Chemistry, Faculty of Science, Gauhati University, Guwahati-781014, Department of Chemistry, Faculty of Science, Gauhati University, Guwahati 781014, Assam, Department of Chemistry, Faculty of Science, Gauhati University, Guwahati-781014

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