Zhang Ying, Shang Kun, Wu Xiaowen, Song Siyu, Li Zebo, Pei Zhichao, Pei Yuxin
Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University Yangling Shaanxi 712100 PR China
RSC Adv. 2018 Jun 13;8(39):21786-21792. doi: 10.1039/c8ra03732a.
A highly efficient synthetic pathway for hypericin (7a) was achieved under mild conditions with an overall yield over two steps of 92% using emodinanthrone as a starting material, where protohypericin, a key precursor of hypericin, was synthesized in water with microwave assistance, which was then photocyclized to hypericin with a high yield 1 h irradiation in a visible light reactor equipped with 575 nm monochromatic lamps. In addition, the method could be used to synthesize hypericin derivatives (7b-d) with similar overall yields. Furthermore, their effects of photodynamic therapy (PDT) were evaluated on A431, HepG-2, and MCF-7 cell lines. The PDT of 7b was better than that of 7a, whereas 7c and 7d were worse. Unlike other cell lines, MCF-7 was not sensitive to any of 7a-d at the same concentrations.
以大黄素蒽酮为起始原料，在温和条件下实现了金丝桃素（7a）的高效合成途径，两步总产率超过92%。其中，金丝桃素的关键前体原金丝桃素在微波辅助下于水中合成，然后在配备575 nm单色灯的可见光反应器中经1小时光照以高产率光环化生成金丝桃素。此外，该方法可用于合成总产率相似的金丝桃素衍生物（7b - d）。此外，还评估了它们对A431、HepG - 2和MCF - 7细胞系的光动力疗法（PDT）效果。7b的PDT效果优于7a，而7c和7d则较差。与其他细胞系不同，MCF - 7在相同浓度下对7a - d均不敏感。
