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黑木层孔菌中具有神经保护活性的 5 对萘醌衍生物 Xylarinaps A-E

Xylarinaps A-E, five pairs of naphthalenone derivatives with neuroprotective activities from Xylaria nigripes.

机构信息

Department of Pharmacy, Xiangya Hospital, Central South University, Changsha, Hunan, 410008, PR China.

School of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan, 430074, PR China.

出版信息

Phytochemistry. 2021 Jun;186:112729. doi: 10.1016/j.phytochem.2021.112729. Epub 2021 Mar 13.

DOI:10.1016/j.phytochem.2021.112729
PMID:33721798
Abstract

Five pairs of undescribed naphthalenone derivative enantiomers, xylarinaps A-E, including one pair of indole naphthalenones and four pairs of naphthalene-naphthalenone dimers, were isolated from the ethyl acetate extracts of the solid fermentation of Xylaria nigripes, which has been used as a traditional Chinese medicinal fungus for the treatment of insomnia, trauma, and depression. The structures of these enantiomers were elucidated based on comprehensive spectroscopic analysis, including NMR and HRESIMS. Their absolute configurations were assigned by the experimental and calculated ECD data. The neuroprotective effects of all the compounds against damage to PC12 cells by oxygen and glucose deprivation (OGD) were evaluated by an in vitro bioassay. The results revealed that xylarinaps A, B, D, and E significantly enhanced cell viability, decreased the levels of malondialdehyde (MDA), increased the levels of superoxide dismutase (SOD) and glutathione peroxidase (GSH-Px), as well as further markedly inhibiting apoptosis, which indicated that these results could be the mode of action of their neuroprotective effect.

摘要

从黑木层孔菌固体发酵的乙酸乙酯提取物中分离得到了 5 对未描述的萘醌衍生物对映体,包括一对吲哚萘醌和 4 对对映体萘醌-萘醌二聚体,黑木层孔菌被用作治疗失眠、创伤和抑郁症的传统中药。基于包括 NMR 和 HRESIMS 在内的综合光谱分析,阐明了这些对映异构体的结构。通过实验和计算 ECD 数据确定了它们的绝对构型。通过体外生物测定评估了所有化合物对 PC12 细胞因缺氧和葡萄糖剥夺 (OGD) 而受损的神经保护作用。结果表明,木霉素 A、B、D 和 E 显著提高了细胞活力,降低了丙二醛 (MDA) 水平,增加了超氧化物歧化酶 (SOD) 和谷胱甘肽过氧化物酶 (GSH-Px) 的水平,并且进一步显著抑制了细胞凋亡,这表明这些结果可能是其神经保护作用的作用模式。

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