School of Pharmacy, Henan University of Chinese Medicine, Zhengzhou, 450046, China.
Institute for Inheritance-Based Innovation of Chinese Medicine, School of Pharmaceutical Sciences, Health Science Center, Shenzhen University, Shenzhen, 518060, China.
Phytochemistry. 2023 Nov;215:113849. doi: 10.1016/j.phytochem.2023.113849. Epub 2023 Sep 9.
As a widely consumed spice and Traditional Chinese Medicine, Alpinae oxyphylla has been used to treat conditions such as diarrhea, ulcers, dementia, and enuresis. Fruits of A. oxyphylla were phytochemically studied and the bioactive constituents against renal fibrosis were identified. Eight previously undescribed acetylated flavonol glucuronides named oxyphyllvonides A-H (1-7 and 10), two known acetylated flavonol glucuronides (8 and 9), together with seven known flavone glycosides (11-17) were isolated from the fruits of A. oxyphylla. Among them, flavonol glucuronides were discovered in Zingiberaceae for the first time. The planar structures of 1-7 and 10 were determined using HRESIMS and extensive spectroscopic techniques (UV, IR, 1D-NMR, and 2D-NMR). The absolute configurations of the sugar moiety in these compounds were determined by using LC-MS analysis of acid-hydrolyzed derivatized monosaccharides. Biological evaluation showed that 7-10, 13, 14, 16 and 17 inhibit renal fibrosis in TGF-β1-induced kidney proximal tubular cells. In addition, 7, 8 and 14 were superior to nootkatone in inhibiting Fibronectin expression. The finding has significant relevance to our ongoing research on the anti-renal fibrosis activity of A. oxyphylla.
作为一种广泛食用的香料和中药，益智已被用于治疗腹泻、溃疡、痴呆和遗尿等疾病。对益智的果实进行了植物化学研究，鉴定出了具有抗肾纤维化活性的生物活性成分。从益智的果实中分离得到了 8 个以前未描述的乙酰化黄酮醇葡萄糖苷，分别命名为 oxyphyllvonides A-H（1-7 和 10）、2 个已知的乙酰化黄酮醇葡萄糖苷（8 和 9），以及 7 个已知的黄酮苷（11-17）。其中，黄酮醇葡萄糖苷首次在姜科中被发现。通过高分辨率质谱（HRESIMS）和广泛的光谱技术（UV、IR、1D-NMR 和 2D-NMR）确定了 1-7 和 10 的平面结构。通过对酸水解衍生的单糖进行 LC-MS 分析，确定了这些化合物中糖部分的绝对构型。生物评价表明，化合物 7-10、13、14、16 和 17 抑制 TGF-β1 诱导的肾近端小管细胞中的肾纤维化。此外，化合物 7、8 和 14 在抑制纤维连接蛋白表达方面优于诺卡酮。这一发现与我们正在进行的关于益智抗肾纤维化活性的研究具有重要意义。
