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热带海洋学报

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红树无瓣海桑果实中糖苷鉴定及其延缓线虫衰老活性研究

刘建雲1, 2, 夏家朗1, 2, 白猛1, 2, 李玥瑶1, 2, 韦金花1, 2, 刘锴1, 2, 高程海1, 2, 易湘茜1, 2   

  1. 1. 广西中医药大学药学院/海洋药物研究院, 广西 南宁 530200;

    2. 广西海洋药物重点实验室, 广西 南宁 530200

  • 收稿日期:2024-08-02 修回日期:2024-10-25 接受日期:2024-10-31
  • 通讯作者: 易湘茜
  • 基金资助:

    国家自然科学基金项目(42466005); 广西中医药大学岐黄工程高层次人才团队培育项目资助(202404); 广西中医药大学“桂派中医药传承创新团队”项目(2022A007；2022B005); 广西中医药大学桂派杏林拔尖人才资助项目 (2022C008); 广西中医药大学广西一流学科建设开放课题一般项目(2018XK044)

The identification of glycosides from the fruit of mangrove Sonneratia apetala and anti-aging activity in Caenorhabditis elegans

LIU Jianyun1, 2, XIA Jialang1, 2, BAI Meng1, 2, LI Yueyao1, 2, WEI Jinhua1, 2, Liu Kai1, 2, GAO Chenghai1, 2, YI Xiangxi1, 2   

  1. 1 Faculty of Pharmacy/Institute of Marine Drugs, Guangxi University of Chinese Medicine, Nanning, 530200, People’s Republic of China

    2 Guangxi Key Laboratory of Marine Drugs, Nanning, 530200, People’s Republic of China

  • Received:2024-08-02 Revised:2024-10-25 Accepted:2024-10-31
  • Contact: YI, Xiangxi
  • Supported by:

    National Natural Science Foundation of China (42466005); The Development Program of High-level Talent Team under the Qihuang Project of Guangxi University of Chinese Medicine (202404); Guangxi University of Chinese Medicine “Guipai Traditional Chinese Medicine Inheritance and Innovation Team” Project (2022A007;2022B005); High-level Talent of Guangxi Traditional Chinese Medicine (2022C008); General Project of Guangxi University of Chinese Medicine for the Construction of First-Class Disciplines in Guangxi (2018XK044)

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摘要： 为获得无瓣海桑果实中具有延缓衰老活性的化合物, 对其正丁醇部位开展成分分离及活性研究。运用反相硅胶色谱、凝胶色谱、高压液相色谱手段对其进行分离纯化, 通过波谱分析及文献对照鉴定结构。以寿命、热应激、咽泵频率、弯曲能力、脂褐素为指标, 考察化合物延缓秀丽隐杆线虫衰老活性, 并通过分子对接预测化合物与DAF-16蛋白的作用方式。从正丁醇部位首次分离得到5个化合物, 鉴定为1, 2, 3, 6-四-O-没食子酰基-β-D-吡喃葡萄糖 (1)、hovetrichoside C (2)、(6R,9S)-3-氧代-α-紫罗兰醇-β-D-葡萄糖苷 (3)、山柰酚-3-O-β-D葡萄糖苷 (4)、3-甲基丁基β-D-吡喃葡萄糖 (5)。化合物2、4、5在100μmol·L-1浓度下具有显著的延缓衰老活性, 分别延长秀丽隐杆线虫寿命的15.9%、15.0%、22.1%, 极显著延长热应激条件下线虫寿命的36.3%、50.6%、46.3%。可提升线虫的咽泵频次、身体弯曲能力以及降低脂褐素的累积。分子对接表明, 化合物2、4、5能与DAF-16蛋白氨基酸稳定结合, 结合能分别为-6.6kcal·moL-1、-6.0kcal·moL-1、-4.6kcal·moL-1。本研究丰富了无瓣海桑果实中延缓衰老的活性物质基础, 为无瓣海桑果实的开发利用提供理论依据。

关键词: 无瓣海桑果实, 糖苷类化合物, 秀丽隐杆线虫, 延缓衰老

Abstract: In order to obtain compounds with anti-aging activity in the fruit of Sonneratia apetala, the chemical constituents of n-butanol alcohol extract were separated and their bioactivities were studied. Compounds were isolated and purified by reverse silica column, gel chromatography and high pressure liquid chromatography. The structure of compounds was identified by modern spectral analysis and literature contrast. The anti-aging activity of compounds were investigated based on Caenorhabditis elegans used the lifespan, heat stress, pharyngeal pumping capacity, body bending ability and lipofuscin as indicator. Molecular docking was used in predicted the interacted mode of compounds with protein DAF-16. Five compounds were isolated from the n-butanol alcohol extract for the first time, identified as 1, 2, 3, 6-tetra-O-galloyl -β-D-glucopyranose (1), hovetrichoside C (2), (6R, 9S)-3-oxo-α-ionol-β-D-glucoside (3), kaempferol-3-O-β-D glucoside (4), 3-methylbutyl β-D-glucopyranoside (5). Compounds 2, 4 and 5 showed an anti-aging activity at 100μmol·L-1 concentration significantly, extended the lifespan of C. elegans in normal culture by 15.9%, 15.0% and 22.1% respectively, significantly prolong the lifespan under heat stress by 36.3%, 50.6% and 46.3% respectively. Improved the frequency of pharyngeal pumping, ability of body bending, and reduced lipofuscin accumulated. Molecular docking showed that compounds 2, 4 and 5 can stably bind to the amino acids of DAF‐16 protein. The binding energy were -6.6kcal·moL-1, -6.0kcal·moL-1, -4.6kcal·moL-1 respectively. This study enriched the material basis of anti-aging activity and provided a basis for the development and utilization in the Sonneratia apetala fruit.

Key words: sonneratia apetala, glycoside compounds, caenorhabditis elegans, anti-aging