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水飞蓟宾的化学。

Chemistry of silybin.

机构信息

Institute of Microbiology AS CR, Centre of Biocatalysis and Biotransformation, Vídeňská 1083, Prague 4, CZ 14220, Czech Republic.

出版信息

Nat Prod Rep. 2014 Sep;31(9):1138-57. doi: 10.1039/c3np70122k.

DOI:10.1039/c3np70122k
PMID:24977260
Abstract

Silybin, a secondary metabolite isolated from the seeds of the blessed milk thistle (Silybum marianum) was discovered as the first member of a new family of natural compounds called flavonolignans in 1959. Over the years it has received the research attention of many organic chemists. This research has resulted in a number of semisynthetic derivatives prepared in an effort to modulate and better target the biological activities of silybin or to improve its physical properties, such as its solubility. A fundamental breakthrough in silybin chemistry was the determination of the absolute configurations of silybin A and silybin B, and the development of methods for their separation. This review covers articles dealing with silybin chemistry and also summarizes all the derivatives prepared.

摘要

水飞蓟宾,一种从奶蓟草(水飞蓟)种子中分离出来的次生代谢产物,于 1959 年被发现,是一类新型天然化合物——类黄酮木脂素的第一个成员。多年来,它受到了许多有机化学家的研究关注。这些研究产生了许多半合成衍生物,旨在调节和更好地针对水飞蓟宾的生物活性,或改善其物理性质,如溶解度。水飞蓟宾化学的一个重大突破是确定了水飞蓟宾 A 和水飞蓟宾 B 的绝对构型,并开发了它们的分离方法。本综述涵盖了有关水飞蓟宾化学的文章,并对所有制备的衍生物进行了总结。

相似文献

1
Chemistry of silybin.水飞蓟宾的化学。
Nat Prod Rep. 2014 Sep;31(9):1138-57. doi: 10.1039/c3np70122k.
2
Molecular structure and stereochemistry of silybin A, silybin B, isosilybin A, and isosilybin B, Isolated from Silybum marianum (milk thistle).从水飞蓟(奶蓟)中分离得到的水飞蓟宾A、水飞蓟宾B、异水飞蓟宾A和异水飞蓟宾B的分子结构和立体化学
J Nat Prod. 2003 Sep;66(9):1171-4. doi: 10.1021/np030163b.
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Silybin, a Major Bioactive Component of Milk Thistle (Silybum marianum L. Gaernt.)-Chemistry, Bioavailability, and Metabolism.水飞蓟宾,奶蓟草(水飞蓟)的主要生物活性成分-化学、生物利用度和代谢。
Molecules. 2017 Nov 10;22(11):1942. doi: 10.3390/molecules22111942.
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Flavonolignans from Aspergillus iizukae, a fungal endophyte of milk thistle (Silybum marianum).奶蓟(水飞蓟)内生真菌 Aspergillus iizukae 的类黄酮木脂素。
J Nat Prod. 2014 Feb 28;77(2):193-9. doi: 10.1021/np400955q. Epub 2014 Jan 23.
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Chemotaxonomic and biosynthetic relationships between flavonolignans produced by Silybum marianum populations.水飞蓟种群产生的黄酮木脂素之间的化学分类学和生物合成关系。
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The study of flavonolignan association patterns in fruits of diverging Silybum marianum (L.) Gaertn. chemotypes provides new insights into the silymarin biosynthetic pathway.对不同化学型水飞蓟果实中黄酮木脂素缔合模式的研究为水飞蓟素生物合成途径提供了新见解。
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The effect of milk thistle (Silybum marianum) and its main flavonolignans on CYP2C8 enzyme activity in human liver microsomes.水飞蓟(奶蓟)及其主要黄酮木脂素对人肝微粒体中CYP2C8酶活性的影响。
Chem Biol Interact. 2017 Jun 1;271:24-29. doi: 10.1016/j.cbi.2017.04.025. Epub 2017 Apr 27.
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Silybin and its congeners: from traditional medicine to molecular effects.水飞蓟宾及其同系物:从传统医学到分子作用。
Nat Prod Rep. 2022 Jun 22;39(6):1264-1281. doi: 10.1039/d2np00013j.
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Simplified procedure of silymarin extraction from Silybum marianum L. Gaertner.水飞蓟宾从水飞蓟中提取的简化工艺
J Chromatogr Sci. 2015 Feb;53(2):366-72. doi: 10.1093/chromsci/bmu049. Epub 2014 Jun 3.
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Two flavonolignans from milk thistle (Silybum marianum) inhibit CYP2C9-mediated warfarin metabolism at clinically achievable concentrations.水飞蓟素(奶蓟草)中的两种类黄酮木质素可在临床可达到的浓度下抑制 CYP2C9 介导的华法林代谢。
J Pharmacol Exp Ther. 2010 Mar;332(3):1081-7. doi: 10.1124/jpet.109.161927. Epub 2009 Nov 24.

引用本文的文献

1
Phytochemical analysis and antimicrobial activity of Silybum marianum L. via multi-solvent extraction.水飞蓟通过多溶剂萃取的植物化学分析及抗菌活性
AMB Express. 2025 Aug 20;15(1):122. doi: 10.1186/s13568-025-01925-2.
2
Leishmanicidal Effect of Silibinin: Disrupting Redox Balance via Trypanothione Reductase Inhibition.水飞蓟宾的杀利什曼原虫作用:通过抑制锥虫硫醇还原酶破坏氧化还原平衡。
ACS Omega. 2025 Jun 18;10(25):27262-27271. doi: 10.1021/acsomega.5c02606. eCollection 2025 Jul 1.
3
Silybin A from reprograms lipid metabolism to induce a cell fate-dependent class switch from triglycerides to phospholipids.
来自水飞蓟宾A可重编程脂质代谢,以诱导细胞命运依赖性的类别转换,从甘油三酯转换为磷脂。
Theranostics. 2025 Jan 6;15(5):2006-2034. doi: 10.7150/thno.99562. eCollection 2025.
4
Novel Strategies Enhancing Bioavailability and Therapeutical Potential of Silibinin for Treatment of Liver Disorders.新型策略增强水飞蓟宾生物利用度及其治疗肝脏疾病的治疗潜力。
Drug Des Devel Ther. 2024 Oct 19;18:4629-4659. doi: 10.2147/DDDT.S483140. eCollection 2024.
5
Physiological and biochemical characteristics of milk thistle ( (L.) Gaertn) as affected by some plant growth regulators.某些植物生长调节剂对水飞蓟((L.) Gaertn)生理生化特性的影响
Food Sci Nutr. 2024 Jun 11;12(8):6022-6033. doi: 10.1002/fsn3.4233. eCollection 2024 Aug.
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Silybin attenuates avermectin-induced oxidative damage in carp respiration by modulating the cGAS-STING pathway and endoplasmic reticulum stress.水飞蓟宾通过调控 cGAS-STING 通路和内质网应激减轻阿维菌素诱导的鲤鱼呼吸氧化损伤。
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Synthesis, characterization, and in vitro-in ovo toxicological screening of silibinin fatty acids conjugates as prodrugs with potential biomedical applications.水飞蓟宾脂肪酸酯类前药的合成、表征及体内外毒理学筛选及其在生物医药中的潜在应用
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The Effects and Safety of Silymarin on β-thalassemia in Children and Adolescents: A Systematic Review based on Clinical Trial Studies.水飞蓟素对儿童和青少年β-地中海贫血的影响和安全性:基于临床试验研究的系统评价。
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