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

doi:10.11978/2024150

热带海洋学报 ›› 2025, Vol. 44 ›› Issue (3): 148-156.doi: 10.11978/2024150CSTR: 32234.14.2024150

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.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 出版日期:2025-05-10 发布日期:2025-06-04
通讯作者: 高程海, 易湘茜
作者简介:
刘建雲(1999—)女, 广西南宁市人, 硕士研究生。email: 1517820954@qq.com
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); 广西中医药大学“桂派中医药传承创新团队”项目(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 investigation of their 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. Faculty of Pharmacy/Institute of Marine Drugs, Guangxi University of Chinese Medicine, Nanning 530200, China
2. Guangxi Key Laboratory of Marine Drugs, Nanning 530200, China

Received:2024-08-02 Revised:2024-10-25 Online:2025-05-10 Published:2025-06-04
Contact: GAO Chenghai, 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); Guangxi University of Chinese Medicine “Guipai Traditional Chinese Medicine Inheritance and Innovation Team” Project(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)

摘要/Abstract

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, 分别使秀丽隐杆线虫寿命延长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%; 并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-6.6、-6.0、-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研究, 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, 结构鉴定, 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 comparison. The anti-aging activity of compounds in Caenorhabditis elegans was investigated using the lifespan, heat stress, pharyngeal pumping capacity, body bending ability and lipofuscin as the indicators. Molecular docking was used in predicting the interaction 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), and 3-methylbutyl β-D-glucopyranoside (5). Compounds 2, 4 and 5 showed an anti-aging activity at 100 μmol·L^-1 concentration significantly, extended the lifespan of C. elegans in normal culture by 15.9%, 15.0% and 22.1% respectively, and significantly prolonged the lifespan under heat stress by 36.3%, 50.6% and 46.3% respectively. They improved the frequency of pharyngeal pumping and the ability of body bending, and reduced the lipofuscin accumulated. Molecular docking showed that compounds 2, 4 and 5 could stably bind to the amino acids of protein DAF-16. The binding energy was -6.6, -6.0 and -4.6 kcal·moL^-1, respectively. This study enriched the material basis of anti-aging activity and provided a basis for the development and utilization of the Sonneratia apetala fruit.

Key words: Sonneratia apetala, glycoside compounds, structural identification, Caenorhabditis elegans, anti-aging

中图分类号:

R284

刘建雲, 夏家朗, 白猛, 李玥瑶, 韦金花, 刘锴, 高程海, 易湘茜. 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[J]. 热带海洋学报, 2025, 44(3): 148-156.

LIU Jianyun, XIA Jialang, BAI Meng, LI Yueyao, WEI Jinhua, LIU Kai, GAO Chenghai, YI Xiangxi. The identification of glycosides from the fruit of mangrove Sonneratia apetala and investigation of their anti-aging activity in Caenorhabditis elegans[J]. Journal of Tropical Oceanography, 2025, 44(3): 148-156.

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药物分组	药物浓度/(μmol·L^-1)	寿命/d			延长比例/%
药物分组	药物浓度/(μmol·L^-1)	平均数	最大寿命	P	延长比例/%
对照组	—	9.897±0.546	19	—	—
阳性药	100	12.246±0.632**	23	0.005	23.9
1	100	9.417±0.604	21	0.790	—
2	100	11.474±0.773*	25	0.016	15.9
3	100	10.689±0.668	22	0.154	8.0
4	100	11.383±0.676*	23	0.041	15.0
5	100	12.085±0.909**	26	0.004	22.1

药物分组	药物浓度/(μmol·L^-1)	寿命/h			延长比例/%
药物分组	药物浓度/(μmol·L^-1)	平均数	最大寿命	P	延长比例/%
对照组	—	12.660±0.825	21	—	—
阳性药	100	21.140±0.732***	29	<0.001	70.0
2	100	17.260±0.738***	27	<0.001	36.3
4	100	19.071±0.799***	28	<0.001	50.6
5	100	18.520±0.974***	30	<0.001	46.3

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

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

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