O-Glucoside of natural cleomiscosin-A: An attenuator of pro-inflammatory cytokine production
Graphical abstract
Introduction
Cleomiscosin-A (CA) is a natural coumarinolignan isolated from various plant sources like Cleome viscosa, Hyoscyamus niger, Rhododendron collettianum, Acer nikoense, etc (Begum et al., 2010a). While CA has been screened for several biological activities (Begum et al., 2010a), it encompassed significant hepatoprotective (Yadav et al., 2010a, Yadav et al., 2010b) and anti-inflammatory potential (Begum et al., 2010b). CA is an oxidative coupled product of fraxetin and coniferyl alcohol, found to be insoluble in water and soluble only in a mixture of methanol and chloroform. In view of the cytokine inhibitory potential exhibited by cleomiscosin-A under in-vitro models (Sharma et al., 2012) and its poor solubility issue, polar derivatives were proposed to be synthesized and tested under cellular and animal models.
Section snippets
Results and discussions
As the study was aimed to improve the hydrophilic property, glycosides of CA were designed. So far no report on semisynthesis or synthesis of coumarinolignan glycosides has been published in the literature. However, isolation of a coumarinolignan glucoside i.e. Yinxiancaoside C (cleomiscosin C-4-O-β-d-glucopyranoside) from Chloranthus japonicus S., has been reported in the literature (Kuang et al., 2009). The designed glycoside molecules were first subjected for molecular docking in order to
General
Multi detection reader (Spectramax M4, California, USA), NMR (GSX 400, JEOL, USA), MS (LC–MS-2020, Shimadzu, Japan) instruments were used as per the requirements. MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) was purchased from Himedia Laboratories Pvt. Ltd. Mumbai, India. Mouse macrophages cell line RAW 264.7 was obtained from the Cell Bank of National Center for Cell Sciences, Pune (Maharashtra, India). Silica gel (# 230–400 and 100–200), silica gel for TLC (G and GF254),
Conflict of interest
The authors do not have any conflict of interest.
Acknowledgements
Authors acknowledge Dr. A. Mallika, Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, Hyderabad for docking study. This work was a part of an Extra Mural Grant sponsored by CSIR-New Delhi grant [02(0045)/12/EMR-II]. SK acknowledges BITS-Pilani and KH acknowledges CSIR, New Delhi for granting fellowship.
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