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      New flavonoids and methylchromone isolated from the aerial parts of Baeckea frutescens and their inhibitory activities against cyclooxygenases-1 and -2

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          Abstract

          In the present study, we carried out a phytochemical investigation of the ethanol extract of the aerial parts of Baeckea frutescens, which resulted in the isolation of two new flavonoid glycosides, myricetin 3- O-(5″- O-galloyl)- α-L-arabinofuranoside ( 1), 6-methylquercetin 7- O- β-D-glucopyranoside ( 2), one new methylchromone glycoside, 7- O-(4′, 6′-digalloyl)- β-D-glucopyranosyl-5-hydroxy-2-methylchromone ( 3), together with three known compounds ( 4–6). The structures of these isolated compounds were established on the basis of 1D and 2D NMR techniques and chemical methods. The anti-inflammatory activities of the compounds 1–6 were evaluated for their inhibitory effects against cyclooxygenases-1 and -2 in vitro. Compounds 1–6 showed potent COX-1 and COX-2 inhibiting activities in vitro with IC 50 values ranging from 1.95 to 5.54 μmol·L −1 and ranging from 1.01 to 2.27 μmol·L −1, respectively.

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          Most cited references 12

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          Baeckeins F-I, four novel C-methylated biflavonoids from the roots of Baeckea frutescens and their anti-inflammatory activities.

          Baeckea frutescens is an aromatic shrub used in South China as an ornamental and as a spice. Four unusual C-methylated biflavonoids named baeckeins F-I (1-4) were isolated from the roots of B. frutescens. The baeckeins F-I possessed a unique carbon skeleton, a flavonol conjugated with a coumaronochromone molecule via the unusual linkages of C-2-C-8 and C-3-O-C-7. Their structures were elucidated by analysis of the 1D ((1)H/(13)C) and 2D NMR (HSQC/HMBC/NOESY) and HR-ESI-MS spectroscopic data, and the absolute stereochemistry for chiral carbons of C-2 and C-3 was established by CD spectrometry combined with quantum chemical calculations. Baeckeins F-I (1-4) were also evaluated for their anti-inflammatory activities by detecting the NO production of LPS-induced RAW264.7 murine macrophage cell line; baeckein I (4) with the β-d-glucose unit and configuration of (2R,3R) exhibited the highest NO inhibitory activity (IC50=15.2 μM), which was similar to that of the positive control indomethacin.
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            Chromones and chromanones from Baeckea frutescens

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              Phloroglucinols from Baeckea frutescens

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                Author and article information

                Journal
                CJNM
                Chinese Journal of Natural Medicines
                Elsevier
                1875-5364
                20 August 2018
                : 16
                : 8
                : 615-620
                Affiliations
                1State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China
                2Jiangsu Key Laboratory of Drug Screening, China Pharmaceutical University, Nanjing 210009, China
                Author notes
                *Corresponding author: WANG Hao, Tel: 86-25-83271328, Fax: 86-25-8530-1528, E-mail: wanghao@ 123456cpu.edu.cn

                These authors have no conflict of interest to declare.

                Article
                S1875-5364(18)30099-2
                10.1016/S1875-5364(18)30099-2
                Copyright © 2018 China Pharmaceutical University. Published by Elsevier B.V. All rights reserved.
                Funding
                Funded by: National Natural Science Foundation of China
                Award ID: 81573309
                This work was supported by the National Natural Science Foundation of China (No. 81573309).

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