Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Bioassay-Guided Isolation of 2-[P-(2-Carboxyhydrazino)Phenoxy]-6-(Hydroxymethyl)Tetrahydro-2h-Pyran-3,4,5-Triol From Oroxylum Indicum and Investigation of Its Molecular Mechanism Action of Apoptosis Induction

Version 1 : Received: 12 February 2021 / Approved: 17 February 2021 / Online: 17 February 2021 (12:55:57 CET)

How to cite: Singh, A.R.; Singh, S.A.; Singh, T.D.; Singh, N.T.; Chanu, T.M.; Singh, O.M.; Singh, L.S. Bioassay-Guided Isolation of 2-[P-(2-Carboxyhydrazino)Phenoxy]-6-(Hydroxymethyl)Tetrahydro-2h-Pyran-3,4,5-Triol From Oroxylum Indicum and Investigation of Its Molecular Mechanism Action of Apoptosis Induction. Preprints 2021, 2021020390 (doi: 10.20944/preprints202102.0390.v1). Singh, A.R.; Singh, S.A.; Singh, T.D.; Singh, N.T.; Chanu, T.M.; Singh, O.M.; Singh, L.S. Bioassay-Guided Isolation of 2-[P-(2-Carboxyhydrazino)Phenoxy]-6-(Hydroxymethyl)Tetrahydro-2h-Pyran-3,4,5-Triol From Oroxylum Indicum and Investigation of Its Molecular Mechanism Action of Apoptosis Induction. Preprints 2021, 2021020390 (doi: 10.20944/preprints202102.0390.v1).

Abstract

Leaf crude extract (aqueous) of Oroxylum indicum (L.) Kurz induces genomic DNA fragmentation, comet formation, and inhibition of cell proliferation in prostate cancer cell line, PC3 as assessed by agarose gel electrophoresis, comet assay, and MTT assay respectively. The bioactive compound was purified through bioassay-guided fractionation using preparative HPLC and MTT as-say. The brown and water-soluble compound was characterized using 1H and 13C nuclear magnetic resonance (NMR), fourier transform infrared (FT-IR) and electrospray ionization (ESI) mass spectrometry, and the compound was iden-tified as a glycosylated hydroquinone derivative, 2-[p-(2-Carboxyhydrazino)phenoxy]-6-(hydroxymethyl) tetrahy-dro-2H-pyran-3,4,5-triol (molecular formula, C13H18N2O8; molecular mass = 330). The identified phytocompound has not been reported earlier elsewhere. Therefore, the common name of the novel anticancer phytocompound isolated from oroxylum indicum in this current study is named as oroxyquinone. The half-maximal inhibitory concentration (IC50) of oroxyquinone on PC3 cells was 19.44 µg/ml (95% CI = 17.97 to 21.04). Oroxyquinone induced cell cycle arrest at S phases and inhibition of cell migration on PC3 as assessed by flow cytome-try and wound healing assay respectively. On investigating the molecular mechanism of inducing apoptosis, the results indicated that the oroxyquinone induced apoptosis through the p38 pathway and cell cycle arrest, however, not through caspase-3 and PARP pathways. The present study identifies a novel an-ticancer molecule and provides scientific evidence supporting the therapeutic potency of OI for ethnomedicinal uses.

Subject Areas

Oroxylum indicum; Oroxyquinone; Traditional medicine; Bioassay Guided Fractionation; caspase-independent apoptosis; anti-metastatic

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