Hydrastine

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Maosheng Cheng - One of the best experts on this subject based on the ideXlab platform.

Dongmei Zhao - One of the best experts on this subject based on the ideXlab platform.

  • studies on asymmetric total synthesis of β Hydrastine via a chiral epoxide ring opening cascade cyclization strategy
    RSC Advances, 2020
    Co-Authors: Xinjing Song, Dongmei Zhao, Yang Zheng, Jiaxin Meng, Qiaohua Qin, Yongxiang Liu, Maosheng Cheng
    Abstract:

    Herein, facile and enantioselective approaches to synthesize the core phthalide tetrahydroisoquinoline scaffold of (−)-β-Hydrastine via both a CF3COOH-catalyzed (86% ee) and KHMDS-catalyzed (78% ee) epoxide ring-opening/transesterification cascade cyclization from chiral epoxide under very mild conditions are described. The key elements include a highly enantioselective epoxidation using the Shi ketone catalyst and an intramolecular CF3COOH-catalyzed cascade cyclization in one pot, and a late-stage C-3′ epimerization under MeOK/MeOH conditions as the key steps to achieve the first total synthesis of (−)-β-Hydrastine (up to 81% ee).

  • Studies on asymmetric total synthesis of (−)-β-Hydrastine via a chiral epoxide ring-opening cascade cyclization strategy
    RSC Advances, 2020
    Co-Authors: Xinjing Song, Dongmei Zhao, Yang Zheng, Jiaxin Meng, Qiaohua Qin, Yongxiang Liu, Maosheng Cheng
    Abstract:

    Herein, facile and enantioselective approaches to synthesize the core phthalide tetrahydroisoquinoline scaffold of (−)-β-Hydrastine via both a CF3COOH-catalyzed (86% ee) and KHMDS-catalyzed (78% ee) epoxide ring-opening/transesterification cascade cyclization from chiral epoxide under very mild conditions are described. The key elements include a highly enantioselective epoxidation using the Shi ketone catalyst and an intramolecular CF3COOH-catalyzed cascade cyclization in one pot, and a late-stage C-3′ epimerization under MeOK/MeOH conditions as the key steps to achieve the first total synthesis of (−)-β-Hydrastine (up to 81% ee).

  • An Acid-Catalyzed Epoxide Ring-Opening/Transesterification Cascade Cyclization to Diastereoselective Syntheses of (±)-β-Noscapine and (±)-β-Hydrastine.
    Organic letters, 2019
    Co-Authors: Yongxiang Liu, Dongmei Zhao, Xinjing Song, Yang Zheng, Jiaxin Meng, Qiaohua Qin, Maosheng Cheng
    Abstract:

    An acid-catalyzed stereoselective epoxide ring-opening/intramolecular transesterification cascade cyclization reaction and N-Boc deprotection was found to be a successful strategy to construct the phthalide tetrahydroisoquinoline skeleton in one pot. Based on this strategy, the unified and highly diastereoselective routes for the total syntheses of (±)-β-Noscapine and (±)-β-Hydrastine were exploited.

  • an acid catalyzed epoxide ring opening transesterification cascade cyclization to diastereoselective syntheses of β noscapine and β Hydrastine
    Organic Letters, 2019
    Co-Authors: Yongxiang Liu, Dongmei Zhao, Xinjing Song, Yang Zheng, Jiaxin Meng, Qiaohua Qin, Maosheng Cheng
    Abstract:

    An acid-catalyzed stereoselective epoxide ring-opening/intramolecular transesterification cascade cyclization reaction and N-Boc deprotection was found to be a successful strategy to construct the phthalide tetrahydroisoquinoline skeleton in one pot. Based on this strategy, the unified and highly diastereoselective routes for the total syntheses of (±)-β-Noscapine and (±)-β-Hydrastine were exploited.

  • (-)-β-Hydrastine suppresses the proliferation and invasion of human lung adenocarcinoma cells by inhibiting PAK4 kinase activity.
    Oncology reports, 2016
    Co-Authors: Bingyu Guo, Shuai Song, Meng Chen, Cheng Maosheng, Dongmei Zhao
    Abstract:

    Abstract (-)-β-Hydrastine is one of the main active components of the medicinal plant, Hydrastis canadensis, which is used in many dietary supplements intended to enhance the immune system. However, whether (-)-β-Hydrastine affects the tumor signaling pathway remains unexplored. In the present study, we found that (-)-β-Hydrastine inhibited the kinase activity of p21-activated kinase 4 (PAK4), which is involved in the regulation of cytoskeletal reorganization, cell proliferation, gene transcription, oncogenic transformation and cell invasion. In the present study, (-)-β-Hydrastine suppressed lung adenocarcinoma cell proliferation by inhibiting expression of cyclin D1/D3 and CDK2/4/6, leading to cell cycle arrest at the G1 phase, in a PAK4 kinase-dependent manner. Moreover, inhibition of PAK4 kinase activity by (-)-β-Hydrastine also promoted the early apoptosis of lung adenocarcinoma cells through the mitochondrial apoptosis pathway. In addition, (-)-β-Hydrastine significantly suppressed the migration and invasion of human lung adenocarcinoma cells in conjunction with concomitant blockage of the PAK4/LIMK1/cofilin, PAK4/SCG10 and PAK4/MMP2 pathways. All of these data indicate that (-)-β-Hydrastine, as a novel PAK4 inhibitor, suppresses the proliferation and invasion of lung adenocarcinoma cells. Taken together, these results provide novel insight into the development of a PAK4 kinase inhibitor and a potential therapeutic strategy for lung cancer.

Yongxiang Liu - One of the best experts on this subject based on the ideXlab platform.

Xinjing Song - One of the best experts on this subject based on the ideXlab platform.

Yang Zheng - One of the best experts on this subject based on the ideXlab platform.