Jeong Se Yun, Lee Kwang Ho, Kim Seon Hee, Yang Min Hye, Lee Gakyung, Kim Ki Hyun
School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea.
Research Institute, Sungkyun Biotech Co., Ltd., Anyang 14118, Republic of Korea.
Plants (Basel). 2025 Jan 17;14(2):261. doi: 10.3390/plants14020261.
The leaves of have been used in treating freckles and effectively reducing cough and sputum in folk medicines. Recently, investigations into the correlation between ginkgo leaves and the proliferative activity of osteogenic differentiation have been conducted. However, bioactive compounds that enhance osteogenesis or exhibit osteoporosis prevention from have not been fully identified. Phytochemical investigation of the MeOH extract of leaves led to the isolation and identification of a new biflavonoid glycoside, ()-glucosciadopitysin (), along with five flavonoids (-), through LC/MS-guided isolation approach. The structure of the new compound was elucidated by the spectroscopic methods, including 1D and 2D NMR analysis, as well as HR-ESIMS. The absolute configuration of sugar moiety was established through acid hydrolysis, followed by chemical derivatization reaction and the axial chirality arising from the biaryl system with substituents was determined by electronic circular dichroism (ECD) calculations. The isolated flavonoids (-) were tested for their effects on mesenchymal stem cell (MSC) differentiation at 20 μM using Oil Red O and alkaline phosphatase (ALP) staining. Ginkgetin () was further evaluated for osteogenic activity on C3H10T1/2 cells at concentrations of 1, 2.5, 5, and 10 μM for 10 days. ALP staining and RT-PCR assessed the gene expression of osteogenic markers ALP and osteopontin (OPN). Ginkgetin () demonstrated the strongest osteogenic activity, significantly increasing the expression of ALP (12.5-fold) and OPN (4.0-fold) at 10 μM, comparable to the positive control, oryzativol A. Ginkgetin () shows potential as a therapeutic agent for osteopenia by promoting osteogenesis in MSCs, suggesting its promising role in treating osteoporosis.
银杏叶在民间药物中已被用于治疗雀斑，并能有效减轻咳嗽和祛痰。最近，人们对银杏叶与成骨分化增殖活性之间的相关性进行了研究。然而，来自银杏叶的增强成骨或预防骨质疏松的生物活性化合物尚未完全确定。通过液相色谱/质谱引导的分离方法，对银杏叶甲醇提取物进行植物化学研究，分离并鉴定出一种新的双黄酮苷，（）-葡糖银松素（），以及五种黄酮类化合物（-）。通过包括一维和二维核磁共振分析以及高分辨电喷雾电离质谱在内的光谱方法阐明了新化合物的结构。通过酸水解，然后进行化学衍生化反应确定糖部分的绝对构型，并通过电子圆二色性（ECD）计算确定具有取代基的联芳基系统产生的轴手性。使用油红O和碱性磷酸酶（ALP）染色，测试分离出的黄酮类化合物（-）在20μM时对间充质干细胞（MSC）分化的影响。进一步评估银杏黄素（）在1、2.5、5和10μM浓度下对C3H⑽T1/2细胞进行10天的成骨活性。ALP染色和逆转录聚合酶链反应评估成骨标志物ALP和骨桥蛋白（OPN）的基因表达。银杏黄素（）表现出最强的成骨活性，在10μM时显著增加ALP（12.5倍）和OPN（4.0倍）的表达，与阳性对照oryzativol A相当。银杏黄素（）通过促进间充质干细胞成骨显示出作为骨质减少治疗剂的潜力，表明其在治疗骨质疏松症方面具有广阔前景。
