Pharmacognosy Laboratory, College of Pharmacy, Chungnam National University, Daejeon 34134, Republic of Korea.
Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States.
J Nat Prod. 2021 Feb 26;84(2):310-326. doi: 10.1021/acs.jnatprod.0c00978. Epub 2021 Jan 19.
Paratrimerins J-Y (- and -, new dimeric coumarins, were obtained from the EtOH(aq) extract of the stems of (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 () and B () 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 (-) 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 - highlighted a diversity in stereochemical outcomes following a Diels-Alder biosynthesis in . With regard to being a recently emerging medicinal resource for liver cancer, the dimers - were evaluated for cytotoxicity against a wide panel of human cancer cell lines. Paratrimerin W () was cytotoxic toward Huh7 hepatocellular carcinoma, HT1080 fibrosarcoma, and HT29 colorectal cancer cells with IC values of 14.9, 18.4, and 22.5 μM, respectively.
Para 二甲素 J-Y(-和-,新的二聚体香豆素,从 Rutaceae 属植物茎的 EtOH(aq)提取物中利用 LC/MS 引导分离得到。二聚体香豆素的结构基于 1D/2D NMR 光谱和 HR-ESIMS 数据分析进行阐明。基于实验和模拟 ECD 数据,确定了 para 二甲素 J-Y 以及两个已知二聚体 para 二甲素 A()和 B()的绝对构型。此外,通过 l-半胱氨酸甲酯和苯异硫氰酸酯衍生物的 LC/MS 分析,确定了 para 二甲素 A、B 和 J-V(-)的糖单元的绝对构型。二聚体非对映异构体的绝对构型的多样性-突出了 Diels-Alder 生物合成中立体化学结果的多样性。由于是肝癌的新兴药用资源,对 -进行了针对广泛的人类癌细胞系的细胞毒性评估。Para 二甲素 W()对 Huh7 肝癌、HT1080 纤维肉瘤和 HT29 结肠直肠癌细胞具有细胞毒性,IC 值分别为 14.9、18.4 和 22.5 μM。