西印度醋栗果实的化学成分研究

	西印度醋栗果实的化学成分研究
	胥佳
导师	张颖君
关键词	大戟科，西印度醋栗，化学成分，生物活性，营养分析 Euphorbiaceae, Phyllanthus acidus (L.) Skeels, Chemical constituents, Biological activity, Nutritional analysis
摘要	西印度醋栗（Phyllanthus acidus（Linn.）Skeel）为大戟科叶下珠属常绿乔木，主要分布于泰国、印度、越南、巴西等热带、亚热带国家和地区，我国云南西双版纳和元江有引种栽培。在泰国传统用药中，西印度醋栗根可退热和治疗皮炎，叶用于高血压，果实具有抗炎、抗氧化、降糖、肝保护等多方面的活性。目前关于根茎和枝叶部位化学成分的报道较多，然而，有关果实化学成分研究却很少。本论文对西印度醋栗的果实进行了化学成分的研究，并对其中部分化合物进行了活性测试。综合运用多种现代分离纯化技术结合波谱分析方法，从中共分离鉴定了40个化合物，包括新化合物9个。其中，黄酮类化合物为其主要成分，共分离鉴定了13个，包括2个少见的与钙离子配位的连磺酸基团的黄酮，它们的化学结构通过X-射线单晶衍射得以确定；其次为木脂素及苯丙素类化合物，共有10个；此外，还得到9个萜类，包括4个闭花木烷型二萜，2个毒鼠子烷型三萜和3个倍半萜；其余8个化合物主要为苯酚衍生物和共轭二炔等。所有化合物均为首次从西印度醋栗果实中分离得到。采用α-葡萄糖苷酶抑制模型，对黄酮类化合物2-11进行了活性评价。其中，部分化合物表现出较强的抑制活性。构效关系分析表明：黄酮C-3位的氧苷化会降低化合物的α-葡萄糖苷酶抑制活性、B环具有邻位二羟基或三羟基取代的槲皮素和杨梅素衍生物，比B环只有一个羟基取代的山奈酚衍生物具有更强的α-葡萄糖苷酶抑制活性。木脂素及苯丙素类化合物显示出一定的清除ABTS+自由基的能力。萜类化合物在40?M的浓度下未显示出明显的细胞毒活性。在化学研究的基础上，本论文还对西印度醋栗果实亦进行了营养成分和广泛代谢组学的分析。结果表明，该植物鲜果含水量较高，达到91.3%；总酸含量为4.09%；矿质元素中，磷元素含量最高，达到了127 mg/kg，其次是钙和镁，分别为64.8和39.2 mg/kg；另外，西印度醋栗果实中还含有多种人体必需氨基酸，如组氨酸、缬氨酸和赖氨酸等。广泛代谢组学分析表明，黄酮类代谢物在该植物果实中的含量最高，占总代谢物的25.67%，其中，又以槲皮苷含量最高，占总代谢物的2.95%，该化合物在上述化学研究过程中也分离得到。较高含量的黄酮类化合物可能是西印度醋栗果实具有较强的α-葡萄糖苷酶抑制活性的物质基础。在脂类化合物中，溶血磷脂酰胆碱（LPC）类物质含量最高，占总代谢物的9.19%，提示该植物果实可能对肝保护有一定作用。此外，西印度醋栗果实中的有机酸类成分主要为柠檬酸和异柠檬酸，该类成分具有较好促进胃酸分泌和食物消化的功能。西印度醋栗果实的营养物质丰富，具有肝保护和降糖等多种生物活性潜力。同时，果实中含有较高含量的有机酸类成分，是很好的天然调味剂。研究结果提示该果实是较好的野生食用植物资源，为该植物资源的进一步开发利用提供了科学依据和基础。; Phyllanthus acidus（Linn.）Skeel, an evergreen shrub or tree in Euphorbiaceae, is mainly distributed in Thailand, Vietnam, Myanmar, Laos, etc. It is also introduced and cultivated in Xishuangbanna and Yuanjiang areas of Yunnan Province, China. In Thai medicine, the roots of P. acidus can reduce fever and treat dermatitis, the leaves are used for hypertension, and the fruits have anti-inflammatory, antioxidant, hypoglycemic, liver protection and other activities. At present, there are many reports on the chemical constituents of leaves, roots and stems, but there are few studies on the chemical constituents of fruits. In this paper, the chemical constituents of the fruits of P. acidus were studied, and the activities of some compounds were tested. A total of 40 compounds were isolated and identified with modern separation and analysis techniques, including 9 new compounds. Among them, 13 flavonoids were isolated and identified, including 2 rare sulfonic flavonoids coordinated with calcium ions. Their structures were determined by X-ray single crystal diffraction. Besides, a total of 10 lignans and phenylpropanoid compounds were isolated from the fruits. In addition, 9 terpenes were isolated from the fruits, including 4 cleistanthane diterpenoids, 2 dichapetalins ,3 sesquiterpenoids. The other 8 compounds were mainly phenol derivatives and conjugate diacetylene. All compounds were isolated from the fruits of P. acidus for the first time. Compounds 2-11 were evaluated for their inhibitory effects on α-glucosidase, some of them show strong inhibitory activity. Structure activity relationship analysis showed that flavonoids belonging to quercetin and myricetin derivatives with ortho-dihydroxy or trihydroxy B-ring structures possessed stronger α-glucosidase inhibitory activity than kaempferol derivatives with only one hydroxy group at B-ring. Some of the lignans and phenylpropanoid compounds showed moderate ABTS+ radical scavenging ability. Terpenoids showed no significant activities at concentrations up to 40 ?M. On the basis of chemical research, Nutrient composition analysis and extensive metabolomics analysis of the fruits of P. acidus were also carried out in this thesis. The result shows that the fresh fruits of this plant have high water content, reaching 91.3%; The total acid content was 4.09%; In mineral elements, the phosphorus content is the highest, reaching 127 mg/kg, followed by calcium and magnesium, 64.8 and 39.2 mg/kg, respectively. In addition, the fruits contain many kinds of essential amino acids, such as histidine, valine and lysine. Extensive metabolomic analysis shows that, the content of flavonoids metabolites in the fruits is the highest, accounting for 25.67% of the total relative content of metabolites, among which the content of quercetin was the first, accounting for 2.95% of the total metabolites, and quercetin was also isolated in the previous experiment. The high content of flavonoids may be responsible for the strong α-g
语种	中文
	2022-05
学位授予单位	中国科学院大学
文献类型	学位论文
条目标识符	http://ir.kib.ac.cn/handle/151853/75103
专题	昆明植物所硕博研究生毕业学位论文
推荐引用方式 GB/T 7714	胥佳. 西印度醋栗果实的化学成分研究[D]. 中国科学院大学,2022.

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