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Novel neuroprotective hydroquinones with a vinyl alkyne from the fungus, Pestalotiopsis microspora.
The Journal of Antibiotics ( IF 2.1 ) Pub Date : 2019-07-24 , DOI: 10.1038/s41429-019-0213-9 Kazuki Kanno 1 , Yukine Tsurukawa 1 , Shinji Kamisuki 1 , Hisanobu Shibasaki 1 , Keita Iguchi 1 , Hironobu Murakami 1 , Jumpei Uchiyama 1 , Kouji Kuramochi 2
The Journal of Antibiotics ( IF 2.1 ) Pub Date : 2019-07-24 , DOI: 10.1038/s41429-019-0213-9 Kazuki Kanno 1 , Yukine Tsurukawa 1 , Shinji Kamisuki 1 , Hisanobu Shibasaki 1 , Keita Iguchi 1 , Hironobu Murakami 1 , Jumpei Uchiyama 1 , Kouji Kuramochi 2
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New hydroquinone derivatives bearing a vinyl alkyne, pestalotioquinols A and B, were isolated from a fungal culture broth of Pestalotiopsis microspora. The structures of these novel compounds were determined by interpretation of spectroscopic data (1D/2D NMR, MS, and IR), and the absolute configuration of the stereogenic center of pestalotioquinol A was assigned using the modified Mosher's method. Nerve growth factor-differentiated neuronal PC12 cells were pretreated with pestalotioquinols A and B and removed from the medium, and then treated with a generator of peroxynitrite (ONOO-), a reactive nitrogen species, to induce cell death. The cytotoxicity of the treated cells was assessed by measuring lactate dehydrogenase leakage. As a result, 1-3 μM pretreatment of pestalotioquinols A and B rescued neuronal PC12 cells from peroxynitrite-induced cytotoxicity and the protective activity was sustained after removing each compound from the medium. These results demonstrate that pestalotioquinol derivatives are a new class of hydroquinones possessing a vinyl alkyne and exhibiting relatively high neuroprotective effects.
中文翻译：
新型神经保护性氢醌与真菌（Pestalotiopsis microspora）中的乙烯基炔烃。
从小孢粉孢菌的真菌培养液中分离出带有乙烯基炔的新对苯二酚衍生物，瘟疫喹啉醇A和B。通过解释光谱数据（1D / 2D NMR，MS和IR）确定了这些新型化合物的结构，并使用改良的Mosher方法确定了鼠疫噻喹诺A立体异构中心的绝对构型。将神经生长因子分化的神经元PC12细胞用鼠疫噻喹啉A和B预处理并从培养基中移出，然后用过氧亚硝酸盐（ONOO-）（一种活性氮物质）进行处理，以诱导细胞死亡。通过测量乳酸脱氢酶渗漏来评估处理过的细胞的细胞毒性。因此，1-3μM的瘟疫喹诺醇A和B预处理可从过氧亚硝酸盐诱导的细胞毒性中拯救神经元PC12细胞，并且从培养基中去除每种化合物后，其保护活性得以维持。这些结果表明，瘟疫噻喹诺尔衍生物是一类新型的对苯二酚，其具有乙烯基炔烃并表现出较高的神经保护作用。
更新日期：2019-11-18
中文翻译：
新型神经保护性氢醌与真菌（Pestalotiopsis microspora）中的乙烯基炔烃。
从小孢粉孢菌的真菌培养液中分离出带有乙烯基炔的新对苯二酚衍生物，瘟疫喹啉醇A和B。通过解释光谱数据（1D / 2D NMR，MS和IR）确定了这些新型化合物的结构，并使用改良的Mosher方法确定了鼠疫噻喹诺A立体异构中心的绝对构型。将神经生长因子分化的神经元PC12细胞用鼠疫噻喹啉A和B预处理并从培养基中移出，然后用过氧亚硝酸盐（ONOO-）（一种活性氮物质）进行处理，以诱导细胞死亡。通过测量乳酸脱氢酶渗漏来评估处理过的细胞的细胞毒性。因此，1-3μM的瘟疫喹诺醇A和B预处理可从过氧亚硝酸盐诱导的细胞毒性中拯救神经元PC12细胞，并且从培养基中去除每种化合物后，其保护活性得以维持。这些结果表明，瘟疫噻喹诺尔衍生物是一类新型的对苯二酚，其具有乙烯基炔烃并表现出较高的神经保护作用。
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