Acylphloroglucinols-based meroterpenoid enantiomers with antiviral activities from Dryopteris crassirhizoma
Acylphloroglucinols-based meroterpenoid enantiomers with antiviral activities from Dryopteris crassirhizoma
复制标题
来自粗根鳞毛蕨的具有抗病毒活性的基于酰基间苯三酚的类萜对映体
DOI：
10.1016/j.indcrop.2020.112415
复制
发表时间：
2020-08-01
影响因子：
5.9
通讯作者：
Li, Yaolan
中科院分区：
文献类型：
--
作者：
Chen, Nenghua;Wu, Zhongnan;Li, Yaolan
绵马贯众（Dryopteris crassirhizoma Nakai）的根茎是中国药典收载的治疗寄生虫感染和病毒性疾病的重要中药。本工作从山茱萸根茎中分离得到10个新的酰基间苯三酚类萜类化合物，（+/-）-dryocrassoids A-J [（+/-）-1-101，沿着6个已知的酰基间苯三酚类化合物（11-16）。绵马值得注意的是，这些新的对映异构体是由酰基间苯三酚和橙花醇型倍半萜构建的部分萜类化合物的第一个例子，而（+/-）-1a/1b，（+/-）-2a/2b，（+/-）-4a/4b作为酮和烯醇互变异构体的不可分离的互变混合物获得。通过高分辨电子喷雾电离质谱（HRESIMS）、核磁共振（NMR）光谱数据和量子化学电子圆二色性（ECD）计算，确定了新的结构和绝对构型。此外，测定了这些化合物对单纯疱疹病毒1型（HSV-1）、单纯疱疹病毒2型（HSV-2）和呼吸道合胞病毒（RSV）的体外抗病毒活性。结果表明，大部分化合物在100 μ M浓度下均表现出不同程度的抗HSV-1和抗RSV作用。本研究为进一步研究和利用D.药材中的粗茎。
The rhizome of Dryopteris crassirhizoma Nakai is an important traditional Chinese medicine listed in Chinese Pharmacopoeia for the treatment of parasitic infestation and viral diseases. In this work, ten enantiomeric pairs of new acylphloroglucinol meroterpenoids, ( +/- )-dryocrassoids A - J [( +/- )-1 - 101, along with six known acylphloroglucinols (11-16) were isolated from the rhizomes of D. crassirhizoma. Notably, these new enantiomers were the first examples of meroterpenoids constructed by acylphloroglucinols and nerolidol-type sesquiterpenes, while ( +/- )-1a/1b, ( +/- )-2a/2b, ( +/- )-4a/4b were obtained as the inseparable interconverting mixtures of keto and enol tautomers. The new structures and absolute configurations were identified by the interpretation of high resolution electron spray ionization mass spectrum (HRESIMS), nuclear magnetic resonance (NMR) spectroscopic data, and quantum chemical electronic circular dichroism (ECD) calculations. In addition, these compounds were assayed for the in vitro antiviral activities against herpes simplex virus type 1 (HSV-1), herpes simplex virus type 2 (HSV-2), and respiratory syncytial virus (RSV). The results indicated that most of the compounds showed anti-HSV-1 and anti-RSV effects to different extent under the concentration of 100 mu M. This study provided evidences for further study and utilization of D. crassirhizoma in medicinal products.