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白族传统食物的植物化学剖析:从厚叶杜鹃花朵中分离出的8种具有细胞毒性潜力的新的杂萜类衍生物。

Phytochemical profiling of Bai traditional food: Eight previously undescribed meroterpenoids derivatives with cytotoxic potential from the flowers of Rhododendron pachypodum.

作者信息

Wang Ying, Luan Jie, Wang Ji-Ai, Chen Xiu, Ren Fu-Cai, Chen Bing, Jia Jing, Zhang Gao-Hong, Li Yong, He Jiang-Bo

机构信息

School of Medicine, Kunming University, Kunming, 650214, PR China.

Center for Physical and Chemical Testing, Yunnan Center for Disease Control and Prevention, Kunming, 650022, PR China.

出版信息

Phytochemistry. 2025 Jul 16;240:114623. doi: 10.1016/j.phytochem.2025.114623.

Abstract

The flowers of Rhododendron pachypodum (Ericaceae), a traditional edible vegetable of the Bai ethnic group in Yunnan Province, China, are widely used both as food and medicine. A systematic phytochemical survey was conducted to fill the knowledge gap regarding its bioactive constituents. Fourteen meroterpenoids, including eight previously undescribed meroterpenoid compounds, rubiginosin I-J (1-2), (±)-rubiginosin K (3), (±)-rubiginosin L (4), (±)-rubiginosin N (5), and six known analogues (6-11), were structurally elucidated using a combination of spectroscopic techniques (1D/2D NMR, HRESIMS, UV, IR). The absolute configurations were unambiguously established by X-ray crystallography and ECD calculations. ‌Selected compounds were assessed for their cytotoxicity, α-glucosidase inhibition, and DPPH radical scavenging activities. Compound 6 demonstrated cytotoxic effects against‌ HepG2 and HeLa cell lines, with IC values of 40.56 μM and 57.43 μM, respectively. Compound 7 exhibited a slight cytotoxic activity against A549 cell lines, with an inhibition rate of 60 %, while compound 8 demonstrated mild activity against both A549 and MDA-MB-468 cells, with inhibition rates of 70 % and 65 %, respectively, at a concentration of 100 μM. In the α-glucosidase inhibition assay, compounds 2-11 showed weak activity at 100 μg/mL. Similarly, in the DPPH assay, these compounds exhibited poor free radical scavenging activity at 100 μg/mL. This study not only expands the chemical diversity of meroterpenoids in Rhododendron pachypodum, but also provides the first evidence of their cytotoxic potential, although structural optimization is required to enhance bioactivity.

摘要

马缨杜鹃(杜鹃花科)的花是中国云南省白族的一种传统可食用蔬菜,被广泛用作食物和药物。为填补其生物活性成分方面的知识空白,开展了一项系统的植物化学研究。利用多种光谱技术(一维/二维核磁共振、高分辨电喷雾电离质谱、紫外光谱、红外光谱)对14种杂萜类化合物进行了结构解析,其中包括8种此前未被描述的杂萜类化合物,即铁锈菌素I-J(1-2)、(±)-铁锈菌素K(3)、(±)-铁锈菌素L(4)、(±)-铁锈菌素N(5),以及6种已知类似物(6-11)。通过X射线晶体学和电子圆二色光谱计算明确了其绝对构型。对部分化合物进行了细胞毒性、α-葡萄糖苷酶抑制活性和二苯基苦味酰基自由基清除活性的评估。化合物6对肝癌细胞系HepG2和宫颈癌细胞系HeLa表现出细胞毒性,IC值分别为40.56 μM和57.43 μM。化合物7对肺癌细胞系A549表现出轻微的细胞毒性活性,抑制率为60%,而化合物8在浓度为100 μM时对A549和人乳腺癌细胞系MDA-MB-468均表现出温和活性,抑制率分别为70%和65%。在α-葡萄糖苷酶抑制试验中,化合物2-11在100 μg/mL时表现出较弱的活性。同样,在二苯基苦味酰基自由基清除试验中,这些化合物在100 μg/mL时表现出较差的自由基清除活性。本研究不仅扩展了马缨杜鹃中杂萜类化合物的化学多样性,还首次证明了它们的细胞毒性潜力,不过需要进行结构优化以增强生物活性。

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