Two new substituted polychiral 5, 6-dihydro-α-pyrones from Orthosiphon diffusus and molecular docking studies. (December 2017)

• Record Type: Journal Article
• Authors: Holla, Harish; Sharma, Akanksha; Bhat, Pritesh; Shinde, Dhananjay; Das, Biswanath
• Is Part Of: Phytochemistry letters. Volume 22(2017:Dec.)
• Page Start: 21
• Page End: 26
• Publication Date: 2017-12
• Subjects: TOPO-I-DNA complex Topoisomerase-I - DNA complex -- LRESIMS low resolution electrospray ionization mass spectrometry -- NMR nuclear magnetic resonance -- COSY 1H-1H correlation spectroscopy -- HSQC heteronuclear single-quantum correlation -- NOESY nuclear over hauser effect spectroscopy -- HMBC heteronuclear multiple bond correlation; Orthodiffene -- Polychiral α− pyrones -- In silico -- 2D NMR -- Docking -- TOPO-I-DNA complex; Botanical chemistry -- Periodicals; Chimie végétale -- Périodiques; 572.205
• DOI: 10.1016/j.phytol.2017.08.006
• Languages: English
• ISSNs: 1874-3900

Abstract

Graphical abstract: Highlights: Substituted polychiral 5, 6-dihydro-α-pyrones isolated from Orthosiphon diffusus . Structure elucidation and relative stereochemistry proposed with 1D & 2D NMR. In silico studies displayed a new binding pattern with Topoisomerase 1B-DNA complex. In silico studies found to be coherent with in vitro anticancer activity on Orthosiphon A–C. Abstract: Chemical investigation on Orthosiphon diffusus lead to isolation of two new substituted polychiral 5, 6-dihydro-α-pyrones, orthodiffenes E-F (5-6 ) which were characterized from the detailed studies of their 1D and 2D NMR spectra. Isolated molecules orthodiffenes E-F (5-6 ) along with previously isolated, reported orthodiffene A-D (1-4 ) molecules were subjected to in silico studies and analysed for anticancer target Topoisomerse I-B − DNA complex. Orthodiffene D and E are giving noteworthy observations while all isolated molecules are showing a pattern of binding in active pocket similar to each other however, different from Camptothecin, an anticancer agent. Orthodiffene A-C have comparable cytotoxicity to Camptothecin, which we have earlier reported.