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[来自雪山杜鹃的杂萜类化合物]

[Meroterpenoids from Rhododendron nivale].

作者信息

Zeng Xi, Zhao Xi, Liu Wei, Yuan Tao

机构信息

College of Life Science, Jiangxi Normal University Nanchang 330022, China.

University and College Key Lab of Natural Product Chemistry and Application in Xinjiang, School of Chemistry and Environmental Science, Yili Normal University Yining 835000, China.

出版信息

Zhongguo Zhong Yao Za Zhi. 2023 Mar;48(5):1273-1279. doi: 10.19540/j.cnki.cjcmm.20221226.201.

Abstract

To elucidate the chemical material basis of Rhododendron nivale, this study comprehensively used various chromatographic techniques to isolate and obtain five new meroterpenoid enantiomers(1a/1b-5a/5b) from the ethyl acetate extract of R. nivale. A variety of spectral analytical methods, such as high-resolution mass spectrometry(HRMS), nuclear magnetic resonance spectroscopy(NMR), and infrared(IR) spectrum, were used to evaluate the structure, combined with the measurement and calculation of electronic circular dichroism(ECD). The new compounds 1a/1b-4a/4b were named as(±)-nivalones A-B(1a/1b-2a/2b) and(±)-nivalnoids C-D(3a/3b-4a/4b), along with one known enantiomer(±)-anthoponoid G(5a/5b). Human neuroblastoma cells(SH-SY5Y cells) induced by hydrogen peroxide(H_2O_2) were used as oxidative stress models to evaluate the protective activity of the isolated compounds against oxidative damage to nerve cells. It was found that compounds 2a and 3a had a certain protective effect on nerve cells against H_2O_2-induced oxidative damage at concentrations of 50 μmol·L~(-1), which increased the cell survival rate from 44.02%±2.30% to 67.82%±1.12% and 62.20%±1.87%, respectively. Other compounds did not show a significant ability to protect cells from oxidative damage. These findings enrich the chemical constituents of R. nivale and provide valuable information for identifying the structure of its meroterpenoids.

摘要

为阐明雪层杜鹃的化学物质基础,本研究综合运用多种色谱技术,从雪层杜鹃的乙酸乙酯提取物中分离并获得了5种新的半萜对映体(1a/1b - 5a/5b)。采用多种光谱分析方法,如高分辨质谱(HRMS)、核磁共振光谱(NMR)和红外光谱(IR)对结构进行鉴定,并结合电子圆二色光谱(ECD)的测定与计算。新化合物1a/1b - 4a/4b分别命名为(±)-雪层杜鹃酮A - B(1a/1b - 2a/2b)和(±)-雪层杜鹃素C - D(3a/3b - 4a/4b),还有一种已知对映体(±)-花类皂苷G(5a/5b)。以过氧化氢(H₂O₂)诱导的人神经母细胞瘤细胞(SH - SY5Y细胞)作为氧化应激模型,评估分离得到的化合物对神经细胞氧化损伤的保护活性。研究发现,化合物2a和3a在浓度为50 μmol·L⁻¹时对神经细胞免受H₂O₂诱导的氧化损伤具有一定的保护作用,细胞存活率分别从44.02%±2.30%提高到67.82%±1.12%和62.20%±1.87%。其他化合物未显示出显著的保护细胞免受氧化损伤的能力。这些研究结果丰富了雪层杜鹃的化学成分,并为其半萜类化合物的结构鉴定提供了有价值的信息。

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