PDF(Pubmed)
Abstract：
Ginkgo biloba L. stands as one of the oldest living tree species, exhibiting a diverse range of biological activities, including antioxidant, neuroprotective, anti-inflammatory, and cardiovascular activities. As part of our ongoing discovery of novel bioactive components from natural sources, we directed our focus toward the investigation of potential bioactive compounds from G. biloba fruit. The profiles of its chemical compounds were examined using a Global Natural Products Social (GNPS)-based molecular networking analysis. Guided by this, we successfully isolated and characterized 11 compounds from G. biloba fruit, including (E)-coniferin (1), syringin (2), 4-hydroxybenzoic acid 4-O-β-D-glucopyranoside (3), vanillic acid 4-O-β-D-glucopyranoside (4), syringic acid 4-O-β-D-glucopyranoside (5), (E)-ferulic acid 4-O-β-D-glucoside (6), (E)-sinapic acid 4-O-β-D-glucopyranoside (7), (1\'R,2\'S,5\'R,8\'S,2\'Z,4\'E)-dihydrophaseic acid 3\'-O-β-D-glucopyranoside (8), eucomic acid (9), rutin (10), and laricitrin 3-rutinoside (11). The structural identification was validated through a comprehensive analysis involving nuclear magnetic resonance (NMR) spectroscopic data and LC/MS analyses. All isolated compounds were evaluated using an E-screen assay for their estrogen-like effects in MCF-7 cells. As a result, compounds 2, 3, 4, 8, and 9 promoted cell proliferation in MCF-7 cells, and these effects were mitigated by the ER antagonist, ICI 182,780. In particular, cell proliferation increased most significantly to 140.9 ± 6.5% after treatment with 100 µM of compound 2. The mechanism underlying the estrogen-like effect of syringin (2) was evaluated using a Western blot analysis to determine the expression of estrogen receptor α (ERα). We found that syringin (2) induced an increase in the phosphorylation of ERα. Overall, these experimental results suggest that syringin (2) can potentially aid the control of estrogenic activity during menopause.
摘要：
银杏是最古老的活树种之一，表现出各种各样的生物活性，包括抗氧化剂，神经保护,抗炎,和心血管活动。作为我们不断发现天然来源的新型生物活性成分的一部分，我们的重点是研究银杏叶果实中潜在的生物活性化合物。使用基于全球天然产品社交（GNPS）的分子网络分析检查了其化合物的概况。以此为指导,我们成功地从银杏叶果实中分离并表征了11种化合物，包括(E)-针叶树(1)，注射器(2),4-羟基苯甲酸4-O-β-D-吡喃葡萄糖苷(3)，香草酸4-O-β-D-吡喃葡萄糖苷(4)，丁香酸4-O-β-D-吡喃葡萄糖苷（5），（E）-阿魏酸4-O-β-D-葡萄糖苷（6），（E）-芥子酸4-O-β-D-吡喃葡萄糖苷（7），(1\'R,2\'S,5\'R,8\'S,2\'Z,4\'E)-二氢草酸3\'-O-β-D-吡喃葡萄糖苷(8)，eucomic酸（9），芦丁（10），和laricitrin3-rutinoside（11）。通过涉及核磁共振（NMR）光谱数据和LC/MS分析的综合分析验证了结构鉴定。使用E-screen测定评价所有分离的化合物在MCF-7细胞中的雌激素样作用。因此,化合物2、3、4、8和9促进MCF-7细胞增殖,这些效应被ER拮抗剂缓解，ICI182,780。特别是,用100μM化合物2处理后，细胞增殖最显著增加至140.9±6.5%。使用Western印迹分析来确定雌激素受体α（ERα）的表达，评估了丁香素（2）雌激素样作用的潜在机制。我们发现丁香素(2)诱导ERα磷酸化的增加。总的来说,这些实验结果表明，丁香素（2）可能有助于控制绝经期间的雌激素活性。
