从非洲吊灯树树皮中提取的抗流感三萜皂苷。
Anti-Influenza Triterpene Saponins from the Bark of Burkea africana.
机构信息
Department of Pharmacognosy, Faculty of Life Sciences , University of Vienna , Althanstraße 14 , 1090 Vienna , Austria.
Department of Chemistry , University of the Free State , PO Box 339, 9300 Bloemfontein , South Africa.
出版信息
J Nat Prod. 2018 Mar 23;81(3):515-523. doi: 10.1021/acs.jnatprod.7b00774. Epub 2018 Feb 2.
Abstract
In an in vitro cytopathic effect inhibition assay with the H3N2 influenza virus A/Hong Kong/68 (HK/68), the bark extract of Burkea africana was found to be a promising antiviral lead with an IC value of 5.5 μg/mL without noteworthy cytotoxicity in Madin Darby canine kidney cells. After several chromatographic steps, triterpene saponins of the lupane and oleanane types were identified as the bioactive principles. In total, eight new triterpene saponins (1-8) with four so far undescribed aglycone structures were isolated and characterized via HRESIMS, GC-MS, and 1D and 2D NMR spectroscopy. Their anti-influenza virus activity on HK/68 and the 2009 pandemic H1N1 strain A/Jena/8178/09 revealed the most potent effects by compounds 7 and 8, with IC values between 0.05 and 0.27 μM. This is the first time triterpene saponins have been reported as constituents of the investigated plant material.
摘要
在一项采用 H3N2 流感病毒 A/Hong Kong/68（HK/68）的体外细胞病变抑制试验中，发现非洲吊灯树的树皮提取物是一种有前途的抗病毒先导化合物，在 Madin Darby 犬肾细胞中其 IC 值为 5.5 μg/mL，而细胞毒性不明显。经过多次色谱步骤，鉴定出具有羽扇豆烷和齐墩果烷类型的三萜皂苷为活性成分。总共分离并通过 HRESIMS、GC-MS 以及 1D 和 2D NMR 光谱鉴定出了 8 种新型三萜皂苷（1-8），其中有 4 种是迄今为止尚未描述的苷元结构。它们对 HK/68 和 2009 年大流行的 H1N1 株 A/Jena/8178/09 的抗流感病毒活性显示，化合物 7 和 8 的效果最强，IC 值在 0.05 和 0.27 μM 之间。这是首次报道三萜皂苷是所研究植物材料的成分。
相似文献
1
Anti-Influenza Triterpene Saponins from the Bark of Burkea africana.从非洲吊灯树树皮中提取的抗流感三萜皂苷。
J Nat Prod. 2018 Mar 23;81(3):515-523. doi: 10.1021/acs.jnatprod.7b00774. Epub 2018 Feb 2.
2
Lanostane Triterpenes from Gloeophyllum odoratum and Their Anti-Influenza Effects.来自香拟层孔菌的羊毛甾烷型三萜及其抗流感作用。
Planta Med. 2019 Feb;85(3):195-202. doi: 10.1055/a-0690-9236. Epub 2018 Aug 21.
3
Uralsaponins M-Y, antiviral triterpenoid saponins from the roots of Glycyrrhiza uralensis.乌拉尔皂素 M-Y，一种来自甘草根的抗病毒三萜皂苷。
J Nat Prod. 2014 Jul 25;77(7):1632-43. doi: 10.1021/np500253m. Epub 2014 Jun 24.
4
Synthesis and In Vitro Anti-Influenza Virus Evaluation of Novel Sialic Acid (C-5 and C-9)-Pentacyclic Triterpene Derivatives.新型唾液酸（C-5 和 C-9）-五环三萜衍生物的合成及体外抗流感病毒活性评价。
Molecules. 2017 Jun 22;22(7):1018. doi: 10.3390/molecules22071018.
5
Cytotoxic triterpenoid saponins acylated with monoterpenic acid from Pithecellobium lucidum.来自亮叶猴耳环的单萜酸酰化细胞毒性三萜皂苷。
J Nat Prod. 2008 Jan;71(1):41-6. doi: 10.1021/np0703794. Epub 2007 Dec 21.
6
Design, synthesis and biological evaluation of amino acids-oleanolic acid conjugates as influenza virus inhibitors.设计、合成及生物评价氨基酸-齐墩果酸缀合物作为流感病毒抑制剂。
Bioorg Med Chem. 2019 Dec 1;27(23):115147. doi: 10.1016/j.bmc.2019.115147. Epub 2019 Oct 15.
7
Rhodamine B-based fluorescent probes for molecular mechanism study of the anti-influenza activity of pentacyclic triterpenes.基于罗丹明 B 的荧光探针用于研究五环三萜类化合物抗流感活性的分子机制。
Eur J Med Chem. 2020 Nov 1;205:112664. doi: 10.1016/j.ejmech.2020.112664. Epub 2020 Jul 26.
8
Zebiriosides A-L, oleanane saponins from the roots of Dendrobangia boliviana.泽比里奥斯苷A-L，来自玻利维亚石斛根的齐墩果烷型皂苷。
Phytochemistry. 2016 Oct;130:262-72. doi: 10.1016/j.phytochem.2016.06.006. Epub 2016 Jun 26.
9
Anti-influenza triterpenoid saponins (saikosaponins) from the roots of Bupleurum marginatum var. stenophyllum.狭叶柴胡根中的抗流感三萜皂苷（柴胡皂苷）
Bioorg Med Chem Lett. 2017 Apr 15;27(8):1654-1659. doi: 10.1016/j.bmcl.2017.03.015. Epub 2017 Mar 7.
10
Triterpene saponins with α-glucosidase inhibition and cytotoxic activity from the leaves of Schefflera sessiliflora.来自无柄鹅掌柴叶的具有α-葡萄糖苷酶抑制和细胞毒性活性的三萜皂苷。
J Asian Nat Prod Res. 2016 Jun;18(6):542-9. doi: 10.1080/10286020.2015.1121999. Epub 2015 Dec 21.
引用本文的文献
1
Anti-Viral Activity of Conessine Against Influenza A Virus.锥丝碱对甲型流感病毒的抗病毒活性。
Int J Mol Sci. 2025 Aug 5;26(15):7572. doi: 10.3390/ijms26157572.
2
Antiviral Activity of Berbamine Against Influenza A Virus Infection.小檗胺对甲型流感病毒感染的抗病毒活性
Int J Mol Sci. 2025 Mar 20;26(6):2819. doi: 10.3390/ijms26062819.
3
Oleraceins from leaves: Quali-quantitative determination and antioxidant potential.来自叶片的马齿苋素：定性定量测定及抗氧化潜力
Curr Res Food Sci. 2025 Jan 30;10:100992. doi: 10.1016/j.crfs.2025.100992. eCollection 2025.
4
Current View on Major Natural Compounds Endowed with Antibacterial and Antiviral Effects.对具有抗菌和抗病毒作用的主要天然化合物的当前观点。
Antibiotics (Basel). 2024 Jun 28;13(7):603. doi: 10.3390/antibiotics13070603.
5
Medicinal Uses of the Fabaceae Family in Zimbabwe: A Review.津巴布韦豆科植物的药用价值：综述
Plants (Basel). 2023 Mar 10;12(6):1255. doi: 10.3390/plants12061255.
6
Phytoestrogen -Sitosterol Exhibits Potent In Vitro Antiviral Activity against Influenza A Viruses.植物雌激素-谷甾醇对甲型流感病毒具有强大的体外抗病毒活性。
Vaccines (Basel). 2023 Jan 19;11(2):228. doi: 10.3390/vaccines11020228.
7
Primary Structure of Glycans by NMR Spectroscopy.通过 NMR 光谱学研究聚糖的一级结构。
Chem Rev. 2023 Feb 8;123(3):1040-1102. doi: 10.1021/acs.chemrev.2c00580. Epub 2023 Jan 9.
8
Medicinal plants used for the management of respiratory diseases in Zimbabwe: Review and perspectives potential management of COVID-19.津巴布韦用于治疗呼吸道疾病的药用植物：综述及对 COVID-19 的潜在治疗前景
Phys Chem Earth (2002). 2022 Dec;128:103232. doi: 10.1016/j.pce.2022.103232. Epub 2022 Sep 21.
9
Evaluation of Melongosides as Potential Inhibitors of NS2B-NS3 Activator-Protease of Dengue Virus (Serotype 2) by Using Molecular Docking and Dynamics Simulation Approach.利用分子对接和动力学模拟方法评估甜瓜皂苷作为登革病毒（血清型2）NS2B-NS3激活蛋白酶潜在抑制剂的作用
J Trop Med. 2022 Aug 23;2022:7111786. doi: 10.1155/2022/7111786. eCollection 2022.
10
Plant-Derived Natural Products as Lead Agents against Common Respiratory Diseases.植物源天然产物作为治疗常见呼吸道疾病的先导药物。
Molecules. 2022 May 10;27(10):3054. doi: 10.3390/molecules27103054.
本文引用的文献
1
Structure-activity relationships of 3-O-β-chacotriosyl oleanic acid derivatives as entry inhibitors for highly pathogenic H5N1 influenza virus.3 - O - β - 查考三糖基齐墩果酸衍生物作为高致病性H5N1流感病毒进入抑制剂的构效关系
Bioorg Med Chem. 2017 Aug 15;25(16):4384-4396. doi: 10.1016/j.bmc.2017.06.025. Epub 2017 Jun 15.
2
Structure-activity relationships of 3-O-β-chacotriosyl oleanane-type triterpenoids as potential H5N1 entry inhibitors.3-O-β-岩藻糖基齐墩果烷型三萜类化合物作为潜在的 H5N1 进入抑制剂的构效关系。
Eur J Med Chem. 2016 Aug 25;119:109-21. doi: 10.1016/j.ejmech.2016.04.061. Epub 2016 Apr 25.
3
hERG Channel Blocking Ipecac Alkaloids Identified by Combined In Silico - In Vitro Screening.通过计算机辅助与体外筛选相结合鉴定出的人醚 - 去极化激活钾通道（hERG）阻断吐根生物碱
Planta Med. 2016 Jul;82(11-12):1009-15. doi: 10.1055/s-0042-105572. Epub 2016 May 4.
4
Dual Acting Neuraminidase Inhibitors Open New Opportunities to Disrupt the Lethal Synergism between Streptococcus pneumoniae and Influenza Virus.双效神经氨酸酶抑制剂为打破肺炎链球菌与流感病毒之间的致命协同作用带来了新机遇。
Front Microbiol. 2016 Mar 21;7:357. doi: 10.3389/fmicb.2016.00357. eCollection 2016.
5
Saikosaponin A inhibits influenza A virus replication and lung immunopathology.柴胡皂苷A抑制甲型流感病毒复制及肺部免疫病理学变化。
Oncotarget. 2015 Dec 15;6(40):42541-56. doi: 10.18632/oncotarget.6448.
6
The preventive and therapeutic potential of natural polyphenols on influenza.天然多酚对流感的预防和治疗潜力
Expert Rev Anti Infect Ther. 2016;14(1):57-80. doi: 10.1586/14787210.2016.1120670. Epub 2015 Dec 7.
7
Structure-activity relationships of 3-O-β-chacotriosyl ursolic acid derivatives as novel H5N1 entry inhibitors.新型H5N1进入抑制剂3 - O-β - 查科三糖基熊果酸衍生物的构效关系
Eur J Med Chem. 2015 Mar 26;93:431-42. doi: 10.1016/j.ejmech.2015.02.029. Epub 2015 Feb 20.
8
Hyaluronidase, phospholipase A2 and protease inhibitory activity of plants used in traditional treatment of snakebite-induced tissue necrosis in Mali, DR Congo and South Africa.马里、刚果民主共和国和南非用于传统治疗蛇咬所致组织坏死的植物的透明质酸酶、磷脂酶A2和蛋白酶抑制活性。
J Ethnopharmacol. 2014 Nov 18;157:171-80. doi: 10.1016/j.jep.2014.09.027. Epub 2014 Sep 23.
9
Uralsaponins M-Y, antiviral triterpenoid saponins from the roots of Glycyrrhiza uralensis.乌拉尔皂素 M-Y，一种来自甘草根的抗病毒三萜皂苷。
J Nat Prod. 2014 Jul 25;77(7):1632-43. doi: 10.1021/np500253m. Epub 2014 Jun 24.
10
Tannins from Hamamelis virginiana bark extract: characterization and improvement of the antiviral efficacy against influenza A virus and human papillomavirus.金缕梅树皮提取物中的单宁：对甲型流感病毒和人乳头瘤病毒抗病毒功效的改善及鉴定。
PLoS One. 2014 Jan 31;9(1):e88062. doi: 10.1371/journal.pone.0088062. eCollection 2014.
Zotero 插件