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      Novel sesquiterpenoids isolated from Chimonanthus praecox and their antibacterial activities

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          Abstract

          In the present study, four new sesquiterpenoids, chimonols A-D (compounds 1–4), together with four known compounds ( 5–8) were isolated from the EtOAc extract of Chimonanthus praecox Link. The structures of these new compounds were elucidated on the basis of spectroscopic techniques (UV, IR, MS, and 1D and 2D NMR), and their absolute configurations were established by comparing experimental and calculated electronic circular dichroism (ECD) spectra. Compounds 1–8 were evaluated for antimicrobial activities and the minimum inhibitory concentrations (MICs) were determined by the broth microdilution method in 96-well culture plates. Compounds 1, 2, and 7 exhibited weak antibacterial effects for S. aureus (ATCC 6538), E. coli (ATCC 11775), and P. aeruginosa (ATCC 10145) with MIC values being 158–249 μg·mL −1. Compounds 3–7 showed activities against C. glabrata (ATCC 2001) and S. aureus (ATCC 43300) with MIC values being 128–197 μg·mL −1. Compounds 1–4 showed activity against S. aureus (ATCC 25923) with MIC values being 162–254 μg·mL −1. The present study provided a basis for future evaluation of these compounds as antibacterial agents.

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          Most cited references 17

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          Two new tryptamine-derived alkaloids from Chimonanthus praecox f. concolor

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            Stachybotrysins A-G, Phenylspirodrimane Derivatives from the Fungus Stachybotrys chartarum.

            Seven new phenylspirodrimane derivatives named stachybotrysins A-G (2-8), together with five known compounds (1, 9-12), were isolated from Stachybotrys chartarum CGMCC 3.5365. Stachybotrysin D (5) is the first reported example of a naturally occurring alcoholic O-sulfation of a phenylspirodrimane, and stachybotrysins F and G (7 and 8) are the first examples possessing an isobenzotetrahydrofuran ring with an acetonyl moiety attached. The structures of these compounds were elucidated on the basis of extensive spectroscopic data analysis and by comparison with reported data. The absolute configurations of 1-8 were determined by X-ray single-crystal diffraction, electronic circular dichroism (ECD), and calculated ECD. Compounds 1 and 8 displayed anti-HIV activity with IC50 values of 15.6 and 18.1 μM, respectively, and 2, 7, 9, and 11 showed inhibitory effect on influenza A virus with IC50 values ranging from 12.4 to 18.9 μM.
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              Antituberculosis activity of natural and semisynthetic azorellane and mulinane diterpenoids.

              The antituberculosis activity of 14 natural azorellane and mulinane diterpenoids isolated from Azorella compacta, Azorella madreporica, Mulinum crassifolium, and Laretia acaulis, together with eight semisynthetic derivatives, was evaluated against two Mycobacterium tuberculosis strains. The natural azorellanes azorellanol (3) and 17-acetoxy-13-alpha-hydroxyazorellane (6), and the semisynthetic mulinanes 13-hydroxy-mulin-11-en-20-oic-acid methyl ester (13) and mulinenic acid methyl ester (23), showed the strongest activity, with MIC values of 12.5 microg/mL against both strains. The methylated derivatives 13-hydroxy-mulin-11-en-20-oic-acid methyl ester (13), mulin-11,13-dien-20-oic acid methyl ester (15) and mulinenic acid methyl ester (23) proved to be more active than the parent compounds.
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                Author and article information

                Journal
                CJNM
                Chinese Journal of Natural Medicines
                Elsevier
                1875-5364
                20 August 2018
                : 16
                : 8
                : 621-627
                Affiliations
                1Guiyang College of Traditional Chinese Medicine, Guiyang 550002, China
                2State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang 550014, China
                3The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, Guiyang 550014, China
                Author notes
                *Corresponding authors: Pan WD, Tel: 86-851-83805348, Fax: 86-851-8380-5081, E-mail: wdpan@ 123456163.com , jinfengyun01@ 123456163.com

                ΔThese two authors contributed equally to this work.

                These authors have no conflict of interest to declare.

                Article
                S1875-5364(18)30100-6
                10.1016/S1875-5364(18)30100-6
                30197128
                Copyright © 2018 China Pharmaceutical University. Published by Elsevier B.V. All rights reserved.
                Funding
                Funded by: Ministry of Science & Technology on China
                Award ID: 2017YFD0201402
                Funded by: National Natural Science Foundation of China
                Award ID: 81160390
                Award ID: 81660580
                This work was supported by the Ministry of Science & Technology on China (No. 2017YFD0201402), the National Natural Science Foundation of China (Nos. 81160390 and 81660580) and the Science and Technology Department of Guizhou Province, China {Nos. (QKHRCTD [2015]4026), (QKHLHZ [2015] 7400), QKHRC [2016]4037, [2011] LKZ7051, and QKZHJ (2009) 2150}.

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