期刊
JOURNAL OF NATURAL PRODUCTS
卷 84, 期 2, 页码 310-326出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.0c00978
关键词
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资金
- Ministry of Oceans and Fisheries, Korea [15250103, PM20030]
- National Research Foundation of Korea (NRF) - Korean Government [NRF2020R1A2B5B01002415]
In this study, new dimeric coumarins Paratrimerins J-Y (1-13 and 16-18) were isolated from the stems of Paramignya trimera using LC/MS guided isolation, and their structures and absolute configurations were determined. The cytotoxicity of the dimers against various human cancer cell lines was evaluated, with Paratrimerin W (16) showing cytotoxicity against Huh7 hepatocellular carcinoma, HT1080 fibrosarcoma, and HT29 colorectal cancer cells.
Paratrimerins J-Y (1-13 and 16-18), new dimeric coumarins, were obtained from the EtOH(aq) extract of the stems of Paramignya trimera (Rutaceae) utilizing LC/MS guided isolation. The structures of the dimeric coumarins were elucidated based on 1D/2D NMR spectroscopic and HR-ESIMS data analyses. The absolute configurations of paratrimerins J-Y along with those of two known dimers paratrimerins A (14) and B (15) were established on the basis of the experimental and simulated ECD data. In addition, the absolute configurations of the sugar units of paratrimerins A, B, and J-V (1-15) were confirmed by LC/MS analysis on L-cysteine methyl ester and phenyl isothiocyanate derivatives. The variety of the absolute configurations of the dimeric diastereomers 1-15 highlighted a diversity in stereochemical outcomes following a Diels-Alder biosynthesis in P. trimera. With regard to P. trimera being a recently emerging medicinal resource for liver cancer, the dimers 1-18 were evaluated for cytotoxicity against a wide panel of human cancer cell lines. Paratrimerin W (16) was cytotoxic toward Huh7 hepatocellular carcinoma, HT1080 fibrosarcoma, and HT29 colorectal cancer cells with IC50 values of 14.9, 18.4, and 22.5 mu M, respectively.
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