Issue 16, 2019

Isolation, structure elucidation, and synthesis of (±)-millpuline A with a suppressive effect in miR-144 expression

Abstract

The isolation, characterization, and total synthesis of (−)-millpuline A and (+)-millpuline A were described here. Their structures were identified by spectral analyses and single-crystal X-ray diffraction. The total synthesis was carried out using 2,4-dihydroxybenzaldehyde in five key steps, including an important [2 + 2] photocycloaddition. The inhibitory activity on miR-144-3p expression of (±)-millpuline A was firstly revealed by western blot and RT-qPCR methods. Through the docking study based on the construction of the pre-miR-144 3D structure and the in vitro model of A549 cells transfected with pre-miR-144, the effects of (−)-millpuline A and (+)-millpuline A were examined, respectively. The results showed that only (−)-millpuline A could interfere with the pre-miR-144 dicing, and thereby modulated the down-stream Nrf2 and γ-Gcsm expression accordingly. Our findings provided a stereo-selective skeleton targeting miR-144, and thereby, will find significance in the context of miR-144/oxidative stress-related diseases.

Graphical abstract: Isolation, structure elucidation, and synthesis of (±)-millpuline A with a suppressive effect in miR-144 expression

Supplementary files

Article information

Article type
Research Article
Submitted
23 May 2019
Accepted
24 Jun 2019
First published
25 Jun 2019

Org. Chem. Front., 2019,6, 2850-2859

Isolation, structure elucidation, and synthesis of (±)-millpuline A with a suppressive effect in miR-144 expression

W. Wang, Y. Tang, Y. Liu, L. Yuan, J. Wang, B. Lin, D. Zhou, L. Sun, R. Huang, G. Chen and N. Li, Org. Chem. Front., 2019, 6, 2850 DOI: 10.1039/C9QO00678H

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