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A new sesquineolignan and four new neolignans isolated from the leaves of Piper betle, a traditional medicinal plant in Myanmar
Bioorganic & Medicinal Chemistry Letters ( IF 2.5 ) Pub Date : 2020-11-15 , DOI: 10.1016/j.bmcl.2020.127682
Thae Thae San 1 , Yue-Hu Wang 2 , Dong-Bao Hu 3 , Jun Yang 2 , Dong-Dong Zhang 2 , Meng-Yuan Xia 4 , Xue-Fei Yang 2 , Yong-Ping Yang 5
Affiliation  

One new sesquineolignan, piperneolignan A (1), four new neolignans, piperneolignans B–E (25), and eight known compounds were isolated from the leaves of Piper betle (Piperaceae) collected from Myanmar. These new structures were determined by analysis of MS and NMR data, and the absolute configuration of piperneolignan A was elucidated by electronic circular dichroism (ECD) calculations. Piperneolignan A (1), piperneolignan B (2), hydroxychavicol (6), p-hydroxycinnamaldehyde (10), and diallylcatechol (13) possessed anti-inflammatory activity against nitric oxide (NO) production in lipopolysaccharide (LPS)-activated murine macrophage RAW 264.7 cells with IC50 values of 9.87, 45.94, 4.80, 26.40, and 40.45 μM, respectively, compared with the positive control NG-monomethyl-l-arginine (L-NMMA, IC50 = 33.84 μM). The two hydroxy groups in the structure of hydroxychavicol are essential for activity, and dimerization or trimerization of hydroxychavicol decreases activity.



中文翻译:

从缅甸传统药用植物Piper betle的叶子中分离出一个新的sesquineolignan和四个新的neolignans

从缅甸采集到的吹笛道贝(Piperaceae)的叶子中分离出一种新的sesquineolignan,piperneolignan A(1),四种新的neolignans,pipeneolignans B–E(25)和八种已知化合物。通过分析MS和NMR数据确定了这些新结构,并通过电子圆二色性(ECD)计算阐明了胡椒木聚糖A的绝对构型。胡椒木聚糖A(1),胡椒木聚糖B(2),羟基查韦尔(6),羟基肉桂醛(10)和二烯丙基儿茶酚(13))在脂多糖(LPS)激活的鼠巨噬细胞RAW 264.7细胞中具有抗一氧化氮(NO)产生的抗炎活性,与阳性对照NG相比,IC 50值分别为9.87、45.94、4.80、26.40和40.45μM -单甲基-1-精氨酸(L-NMMA,IC 50=33.84μM)。羟基chavicol结构中的两个羟基对活性至关重要,羟基chavicol的二聚或三聚会降低活性。

更新日期:2020-11-15
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