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液相色谱-质谱联用引导下从博落回中分离出三对对映体生物碱及其对映体拆分、抗增殖活性、诱导凋亡特性

LC-MS guided isolation of three pairs of enantiomeric alkaloids from Macleaya cordata and their enantioseparations, antiproliferative activity, apoptosis-inducing property.

作者信息

Sai Chunmei, Li Dahong, Li Shengge, Han Tong, Guo Yongzhi, Li Zhanlin, Hua Huiming

机构信息

School of Pharmacy, Jining Medical University, Rizhao, 276826, Shandong Province, People's Republic of China.

Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, 110016, Liaoning Province, People's Republic of China.

出版信息

Sci Rep. 2017 Nov 13;7(1):15410. doi: 10.1038/s41598-017-15423-4.

DOI:10.1038/s41598-017-15423-4
PMID:29133815
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5684219/
Abstract

(±)-Macleayins F-H (1-3), three pairs of new enantiomeric alkaloid dimers, along with four known alkaloids (4-7) as their plausible biogenetic precursors, were isolated from the aerial parts of Macleaya cordata. Compounds 1-3 were obtained under the guidance of LC-MS investigation, and their structures were elucidated by analysis of the 1D and 2D NMR spectroscopic data. The racemic mixtures were successfully separated by chiral HPLC, and the absolute configurations of enantiomers were determined by electronic circular dichroism (ECD) spectroscopy. Compounds 1-7 showed antiproliferative activity against HL-60 with IC values of 1.34-41.30 μM, especially compounds 1-2 exhibited the best inhibitory activity against HL-60 cell lines. In addition, the preliminary mechanism investigation for compound 2 using Annexin V/7-AAD double-staining assay, DAPI staining assay and JC-1 staining method, indicated that 2 inhibited cancer cell proliferation potentially through inducing apoptosis via the mitochondria-related pathway and arrested cell cycle of HL-60 cells at S phase.

摘要

从博落回的地上部分分离得到了（±）-血根碱F-H（1-3），三对新的对映体生物碱二聚体，以及四种已知生物碱（4-7）作为其可能的生源合成前体。化合物1-3是在液相色谱-质谱（LC-MS）研究的指导下获得的，其结构通过一维和二维核磁共振（NMR）光谱数据分析得以阐明。通过手性高效液相色谱成功分离了外消旋混合物，并通过电子圆二色（ECD）光谱确定了对映体的绝对构型。化合物1-7对HL-60细胞具有抗增殖活性，IC值为1.34-41.30μM，尤其是化合物1-2对HL-60细胞系表现出最佳抑制活性。此外，使用膜联蛋白V/7-氨基放线菌素D双染法、4',6-二脒基-2-苯基吲哚（DAPI）染色法和JC-1染色法对化合物2进行的初步机制研究表明，化合物2可能通过线粒体相关途径诱导凋亡并使HL-60细胞的细胞周期停滞在S期来抑制癌细胞增殖。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db71/5684219/1069b65055ce/41598_2017_15423_Fig7_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db71/5684219/6ef52149eff0/41598_2017_15423_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db71/5684219/9d60fb80f611/41598_2017_15423_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db71/5684219/a390a9084141/41598_2017_15423_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db71/5684219/bf6db28388a5/41598_2017_15423_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db71/5684219/0ecf063abb08/41598_2017_15423_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db71/5684219/42c1e3ca21ac/41598_2017_15423_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db71/5684219/1069b65055ce/41598_2017_15423_Fig7_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db71/5684219/6ef52149eff0/41598_2017_15423_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db71/5684219/9d60fb80f611/41598_2017_15423_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db71/5684219/a390a9084141/41598_2017_15423_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db71/5684219/bf6db28388a5/41598_2017_15423_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db71/5684219/0ecf063abb08/41598_2017_15423_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db71/5684219/42c1e3ca21ac/41598_2017_15423_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db71/5684219/1069b65055ce/41598_2017_15423_Fig7_HTML.jpg

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