Suppr超能文献

超高效液相色谱-光电二极管阵列检测器-四极杆飞行时间质谱联用引导下从长圆叶藤黄树叶中分离异戊烯基呫吨酮和苯甲酰基间苯三酚及其迁移抑制活性

UPLC-PDA-QTOFMS-guided isolation of prenylated xanthones and benzoylphloroglucinols from the leaves of Garcinia oblongifolia and their migration-inhibitory activity.

作者信息

Zhang Hong, Zheng Dan, Ding Zhi-Jie, Lao Yuan-Zhi, Tan Hong-Sheng, Xu Hong-Xi

机构信息

School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Shanghai, 201203, P.R. China.

Engineering Research Centre of Shanghai Colleges for TCM New Drug Discovery, Shanghai, 201203, P.R. China.

出版信息

Sci Rep. 2016 Oct 21;6:35789. doi: 10.1038/srep35789.

Abstract

A UPLC-PDA-QTOFMS-guided isolation strategy was employed to screen and track potentially new compounds from Garcinia oblongifolia. As a result, two new prenylated xanthones, oblongixanthones D and E (1-2), six new prenylated benzoylphloroglucinol derivatives, oblongifolins V-Z (3-7) and oblongifolin AA (8), as well as a known compound oblongifolin L (9), were isolated from the EtOAc-soluble fraction of an acetone extract of the leaves of Garcinia oblongifolia guided by UPLC-PDA-QTOFMS analysis. The structures of the new compounds were elucidated by 1D- and 2D-NMR spectroscopic analysis and mass spectrometry. Experimental and calculated ECD spectra were used to determine the absolute configurations. The results of wound healing and transwell migration assay showed that oblongixanthones D (1), E (2), and oblongifolin L (9) have the ability to inhibit cancer cell migration in lower cytotoxic concentrations. Western blotting results showed that these compounds exhibited an anti-metastasis effect mainly through downregulating RAF protein levels. In addition, 2 and 9 could inhibit phospho-MEK and phospho-ERK at downstream. Moreover, 1, 2, and 9 could inhibit snail protein level, suggesting that they could regulate the EMT pathway.

摘要

采用超高效液相色谱-光电二极管阵列-四极杆飞行时间质谱引导的分离策略,从长圆叶藤黄中筛选和追踪潜在的新化合物。结果,在超高效液相色谱-光电二极管阵列-四极杆飞行时间质谱分析的引导下,从长圆叶藤黄叶丙酮提取物的乙酸乙酯可溶部分中分离出两种新的异戊烯基黄酮,长圆叶黄酮D和E(1-2),六种新的异戊烯基苯甲酰基间苯三酚衍生物,长圆叶酚V-Z(3-7)和长圆叶酚AA(8),以及一种已知化合物长圆叶酚L(9)。通过一维和二维核磁共振光谱分析和质谱对新化合物的结构进行了阐明。利用实验和计算的电子圆二色谱确定绝对构型。伤口愈合和Transwell迁移试验结果表明,长圆叶黄酮D(1)、E(2)和长圆叶酚L(9)在较低细胞毒性浓度下具有抑制癌细胞迁移的能力。蛋白质免疫印迹结果表明,这些化合物主要通过下调RAF蛋白水平发挥抗转移作用。此外,2和9可在下游抑制磷酸化MEK和磷酸化ERK。而且,1、2和9可抑制蜗牛蛋白水平,表明它们可调节上皮-间质转化途径。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2ec9/5073302/50e1a8be6655/srep35789-f1.jpg

相似文献

2
Prenylated benzoylphloroglucinols and xanthones from the leaves of Garcinia oblongifolia with antienteroviral activity.
J Nat Prod. 2014 Apr 25;77(4):1037-46. doi: 10.1021/np500124e. Epub 2014 Mar 28.
3
Cytotoxic and anti-inflammatory prenylated benzoylphloroglucinols and xanthones from the twigs of Garcinia esculenta.
J Nat Prod. 2014 Jul 25;77(7):1700-7. doi: 10.1021/np5003498. Epub 2014 Jun 24.
6
Bioassay-Guided Isolation of Prenylated Xanthone Derivatives from the Leaves of Garcinia oligantha.
J Nat Prod. 2016 Jul 22;79(7):1752-61. doi: 10.1021/acs.jnatprod.6b00137. Epub 2016 Jun 22.
7
Tetrandraxanthones A-I, Prenylated and Geranylated Xanthones from the Stem Bark of Garcinia tetrandra.
J Nat Prod. 2019 May 24;82(5):1312-1318. doi: 10.1021/acs.jnatprod.9b00046. Epub 2019 Apr 12.
8
Antimicrobial prenylated benzoylphloroglucinol derivatives and xanthones from the leaves of Garcinia goudotiana.
Phytochemistry. 2014 Jun;102:162-8. doi: 10.1016/j.phytochem.2014.03.006. Epub 2014 Mar 29.
9
Xanthone derivatives from the leaves of Garcinia oligantha.
Eur J Med Chem. 2019 Nov 1;181:111536. doi: 10.1016/j.ejmech.2019.07.039. Epub 2019 Jul 15.
10
Scalemic Caged Xanthones Isolated from the Stem Bark Extract of Garcinia propinqua.
J Nat Prod. 2017 May 26;80(5):1658-1667. doi: 10.1021/acs.jnatprod.7b00240. Epub 2017 May 10.

引用本文的文献

1
Biphenyls in Clusiaceae: Isolation, structure diversity, synthesis and bioactivity.
Front Chem. 2022 Dec 1;10:987009. doi: 10.3389/fchem.2022.987009. eCollection 2022.
2
An Update on the Anticancer Activity of Xanthone Derivatives: A Review.
Pharmaceuticals (Basel). 2021 Nov 11;14(11):1144. doi: 10.3390/ph14111144.
3
Polyprenylated Acylphloroglucinols With Different Carbon Skeletons From the Fruits of .
Front Chem. 2021 Oct 26;9:756452. doi: 10.3389/fchem.2021.756452. eCollection 2021.
4
Anticancer Properties and Mechanism of Action of Oblongifolin C, Guttiferone K and Related Polyprenylated Acylphloroglucinols.
Nat Prod Bioprospect. 2021 Dec;11(6):629-641. doi: 10.1007/s13659-021-00320-1. Epub 2021 Sep 29.

本文引用的文献

4
Oblongifolin C inhibits metastasis by up-regulating keratin 18 and tubulins.
Sci Rep. 2015 May 14;5:10293. doi: 10.1038/srep10293.
5
Inhibitory effect of oblongifolin C on allergic inflammation through the suppression of mast cell activation.
Mol Cell Biochem. 2015 Aug;406(1-2):263-71. doi: 10.1007/s11010-015-2444-9. Epub 2015 May 13.
6
Snail promotes epithelial mesenchymal transition in breast cancer cells in part via activation of nuclear ERK2.
PLoS One. 2014 Aug 14;9(8):e104987. doi: 10.1371/journal.pone.0104987. eCollection 2014.
7
Prenylated benzoylphloroglucinols and xanthones from the leaves of Garcinia oblongifolia with antienteroviral activity.
J Nat Prod. 2014 Apr 25;77(4):1037-46. doi: 10.1021/np500124e. Epub 2014 Mar 28.
9
A new bixanthone derivative from the bark of Garcinia oblongifolia.
Nat Prod Res. 2014;28(2):81-5. doi: 10.1080/14786419.2013.841686. Epub 2013 Oct 1.

文献AI研究员

20分钟写一篇综述,助力文献阅读效率提升50倍。

立即体验

用中文搜PubMed

大模型驱动的PubMed中文搜索引擎

马上搜索

文档翻译

学术文献翻译模型,支持多种主流文档格式。

立即体验