展萼金丝桃化学成分及其抗氧化活性研究
Study on the Chemical Constituents from Hypericum lancasteri and Their Antioxidant Activities
DOI: 10.12677/HJMCe.2023.113021, PDF,    科研立项经费支持
作者: 张潘潘, 周 英, 梁嘉俊, 梁 婷, 刘 爽, 余 欢, 魏 鑫*：贵州中医药大学药学院，贵州 贵阳
关键词: 展萼金丝桃；抗氧化活性；化学成分；DPPH；Xanthone；Hypericum lancasteri； Antioxidant Activity； Chemical Composition； DPPH； Xanthones
摘要: 目的：对展萼金丝桃(Hypericum lancasteri N. Robson)的化学成分进行分离鉴定；对其单体化合物进行抗氧化活性评价。方法：展萼金丝桃干燥地上部分经粉碎，95%甲醇回流提取得总提取物，使用硅胶、凝胶、MCI、ODS柱色谱、高效液相色谱(HPLC)等多种分离技术对总提取物进行分离纯化，结合核磁共振氢谱(1H NMR)、碳谱(13C NMR)以及质谱(MS)等解析手段，通过文献数据分析确定所得化合物结构。采用DPPH自由基清除法对化合物1-4进行抗氧化活性评价。结果：共分离得到3个xanthone类化合物和2个其他类化合物，分别鉴定为1,7-dihydroxyxanthone (1), 2-hydroxyxanthone (2), 2,3-二甲氧基口山酮(3), hyperdioxanes B (4) 和2-methyl-6-isopropyl-7-hydroxymethyl naphthalene (5)，化合物1-5均为首次从该植物中分离得到。化合物1-4在400 µmol/L浓度下的DPPH自由基清除率分别为11.44%，9.68%，11.04%，9.72%。结论：从展萼金丝桃地上部分分离得到5个单体化合物，均为首次从该植物中分离得到，丰富了该植物的物质基础，同时生物活性研究为展萼金丝桃在抗氧化活性方面的药物应用提供了线索。
Abstract: Objective: To isolate and identify the chemical composition of Hypericum lancasteri N. Robson; evaluate the antioxidant activity of its monomer compounds. Methods: The dried aerial part of H. lancasteri was crushed, and the total extract was extracted by 95% methanol reflux. The total extract was separated and purified by silica gel column chromatography, MCI column chromatography, ODS column chromatography, high performance liquid chromatography (HPLC) and other separation technologies. The structure of the isolated monomers was determined by 1H and 13C nuclear magnetic resonance (NMR) as well as mass spectrometry (MS). The antioxidant activity for compounds 1-4 was evaluated using DPPH radical scavenging method. Results: A total of three xanthones together with two other compounds were isolated and identified as 1,7-dihydroxyxanthone (1), 2-dihydroxyxanthone (2), 2,3-dimethoxyxanthone (3), hyperdioxanes B (4), and 2-methyl-6-iso- propyl-7-hydroxymethyl naphthalene (5) respectively. Compounds 1-5 were isolated from this plant for the first time. The DPPH radical scavenging rates of compounds 1-4 (400 µmol/L) were 11.44%, 9.68%, 11.04% and 9.72%, respectively. Conclusion: Five monomeric compounds were isolated from the aerial part of the H. lancasteri, all of which were the first to be isolated from the plant, enriching the material foundation of the plant. At the same time, biological activity research provided clues for the drug application of the plant in terms of antioxidant activity.
文章引用：张潘潘, 周英, 梁嘉俊, 梁婷, 刘爽, 余欢, 魏鑫. 展萼金丝桃化学成分及其抗氧化活性研究[J]. 药物化学, 2023, 11(3): 167-173. https://doi.org/10.12677/HJMCe.2023.113021

参考文献

[1] 陈玉菡, 刘旭, 慕泽泾, 等. 重庆华蓥山山脉金丝桃属药用植物资源调查[J]. 中国现代中药, 2011, 13(9): 12-14.
[2] 吕洪飞, 初庆刚, 胡正海. 金丝桃属植物的化学成分研究进展[J]. 中草药, 2002, 33(12): 82-85.
[3] 纪圆圆, Adam N., Edward J.K., 等. 星萼金丝桃的化学成分和抗氧化活性研究[J]. 中国中药杂志, 2018, 43(18): 3701-3707.
[4] 肖会泉, 杨子峰, 刘妮, 等. 贯叶金丝桃提取物抗乙型肝炎病毒的体外实验研究[J]. 中药材, 2005, 28(3): 213-214.
[5] 辛义周, 张希成, 唐文照. 地耳草的化学成分及药理作用研究进展[J]. 山东医药工业, 2003, 22(2): 28-29.
[6] 谢孟姣, 郭勇秀, 李芳婵, 等. 元宝草的化学成分、药理作用研究进展和质量标志物分析预测[J]. 中医药学报, 2021, 49(10): 40-44.
[7] Yang, X.W., Grossman, R.B. and Xu, G. (2018) Research Progress of Polycyclic Polyprenylated Acylphloroglucinols. Chemical Reviews, 118, 3508-3558. [Google Scholar] [CrossRef] [PubMed]
[8] 殷志琦, 王英, 张冬梅, 等. 金丝桃属植物化学成分研究进展[J]. 中国野生植物资源, 2004, 23(1): 6-7+11.
[9] 宋萍, 郝吉, 王岩, 等. 金丝桃属植物中多环多异戊烯基间苯三酚类成分和生物活性的研究进展[J]. 中国中药杂志, 2021, 46(19): 4881-4890.
[10] 谢婷婷, 孙隆儒, 娄红祥, 等. 金丝桃属植物抗菌作用的研究进展[J]. 中药材, 2010, 33(1): 146-149.
[11] Sarris, J., Panossian, A., Schweitzer, I., et al. (2011) Herbal Medicine for Depression, Anxiety and Insomnia: A Review of Psychopharmacology and Clinical Evidence. European Neuropsychopharmacology, 21, 841-860. [Google Scholar] [CrossRef] [PubMed]
[12] Barnes, J., Anderson, L.A. and Phillipson, J.D. (2001) St John’s Wort (Hypericum perforatum L.): A Review of Its Chemistry, Pharmacology and Clinical Properties. Journal of Pharmacy and Pharmacology, 53, 583-600. [Google Scholar] [CrossRef] [PubMed]
[13] Fobofou, S.A.T., Franke, K., Brandt, W., et al. (2023) Bichro-monol, a Dimeric Coumarin with Anti-HIV Activity from the Stem Bark of Hypericum roeperianum. Natural Product Research, 37, 1947-1953. [Google Scholar] [CrossRef] [PubMed]
[14] Zirak, N., Shafiee, M., Soltani, G., et al. (2019) Hypericum perforatum in the Treatment of Psychiatric and Neurodegenerative Disorders: Current Evidence and Potential Mecha-nisms of Action. Journal of Cellular Physiology, 234, 8496-8508. [Google Scholar] [CrossRef] [PubMed]
[15] 唐锋, 田元新, 黎旭, 等. 基于网络药理学的贯叶连翘抗抑郁活性成分作用机制研究[J]. 时珍国医国药, 2019, 30(8): 1844-1847.
[16] 郑清明, 秦路平, 郑汉臣, 等. 金丝桃属植物的HPLC指纹谱研究[J]. 中草药, 2003, 36(4): 80-85.
[17] 屠万倩, 张留记, 夏曼玉, 等. 杜仲叶清除DPPH自由基动力学特性及抗氧化活性成分筛选[J]. 中国药学杂志, 2022, 57(4): 264-268.
[18] 连双双. 氧杂蒽酮类化合物的研究进展[J]. 广东化工, 2014, 41(2): 46-47.
[19] 席天伦, 李晓秀, 刘波. 山竹果皮的化学成分及其药理活性研究进展[J]. 天然产物研究与开发, 2018, 30(5): 888-899.
[20] 肖志勇, 穆青. 金丝桃属植物化学成分研究进展[J]. 天然产物研究与开发, 2007, 19(2): 344-355.
[21] 刘健, 肖朝江, 崔淑君, 等. 匙萼金丝桃化学成分及镇痛与抗疟活性研究[J]. 中国药学杂志, 2019, 54(8): 614-619.
[22] Frahm, A.W. and Chaudhuri, R.K. (1979) 13C NMR Spectroscopy of Substituted Xanthones-II. 13C NMR Spectral Study of Polyhydroxy Xanthones. Tetrahedron, 35, 2035-2038. [Google Scholar] [CrossRef] 
[23] 罗蕾, 李祖强, 马国义. 近无柄金丝桃中的口山酮类成分[J]. 云南大学学报(自然科学版), 2004, 26(1): 56-60.
[24] Niwa, K., Tanaka, N., Kim, S.Y., et al. (2018) Hyperdiox-ane A, a Conjugate of Dibenzo-1,4-dioxane and Sesquiterpene from Hypericum ascyron. Organic Letters, 20, 5977-5980. [Google Scholar] [CrossRef] [PubMed]
[25] Hou, L., Ding, G., Guo, B., et al. (2015) New Ses-quiterpenoids and a Diterpenoid from Alpinia oxyphylla. Molecules (Basel, Switzerland), 20, 1551-1559. [Google Scholar] [CrossRef] [PubMed]
[26] Facchinetti, F., Dawson, V.L. and Dawson, T.M. (1998) Free Radicals as Mediators of Neuronal Injury. Cellular and Molecular Neurobiology, 18, 667-682. [Google Scholar] [CrossRef] 
[27] Peuchen, S., Bolaños, J.P., Heales, S.J., et al. (1997) Interrelation-ships between Astrocyte Function, Oxidative Stress and Antioxidant Status within the Central Nervous System. Progress in Neurobiology, 52, 261-281. [Google Scholar] [CrossRef] 
[28] Wang, S.N., Li, Q., Jing, M.H., et al. (2016) Natural Xan-thones from Garcinia mangostana with Multifunctional Activities for the Therapy of Alzheimer’s Disease. Neurochem-ical Research, 41, 1806-1817. [Google Scholar] [CrossRef] [PubMed]