The 2,3-epoxy naphthoquinol produced by endophyte <i>Arthrinium marii</i> M-211

The 2,3-epoxy naphthoquinol produced by endophyte <i>Arthrinium marii</i> M-211
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内生菌<i>Arthrinium marii</i> M-211产生的2,3-环氧萘醌

DOI:
10.1080/14786419.2021.1998899
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发表时间:
2021
影响因子:
2.2
通讯作者:
Shiono Yoshihito
Shiono Yoshihito
中科院分区:
化学3区
文献类型:
--
作者:
Sofian Ferry Ferdiansyah;Suzuki Takuma;Supratman Unang;Harneti Desi;Maharani Rani;Salam Supriatno;Abdullah Fajar Fauzi;Yoshida Jun;Ito Yoshiaki;Koseki Takuya;Shiono Yoshihito

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从一株分离自红树林植物的内生真菌ArthriniummariM-211中分离得到一个新的2,3-环氧萘醌,命名为(6 R,7 R,8 R)-茶烯酮A(1),它具有一个氧杂三环[5.4.0.03,5]十一碳三烯-2-酮骨架,另外还有两个已知化合物(6S,7 R,8 R)-茶烯酮(2)和关节霉素酮(3)。通过核磁共振(NMR)和质谱(MS)数据分析以及电子圆二色性(ECD)谱的含时密度泛函理论(TDDFT)计算,确定了化合物1的结构,包括绝对立体化学。此外,通过ECD光谱数据分析,推测2的绝对结构为1的非对映异构体。化合物1、2和3对H4 IIE大鼠肝癌细胞具有细胞毒活性,IC 50值分别为67.5、46.6和13.4 μM。
A novel 2,3-epoxy naphthoquinol, named (6R,7R,8R)-theissenone A (1), possessing an oxatricyclo[5.4.0.03,5]undeca-trien-2-one skeleton, together with two known compounds, (6S,7R,8R)-theissenone (2) and arthrinone (3), were produced by an endophytic fungus,Arthrinium mariiM-211, which was isolated from mangrove plants. The structure of1, including the absolute stereochemistry, was elucidated by analysis of nuclear magnetic resonance (NMR) and mass spectrometry (MS) data and time-dependent density functional theory (TDDFT) calculations of electronic circular dichroism (ECD) spectra. Additionally, the absolute structure of2was deduced as a diastereomer of1using ECD spectral data analysis. Compounds1,2and3exhibited cytotoxic activity against the H4IIE rat hepatoma cells, with IC50values of 67.5, 46.6 and 13.4 µM, respectively.
DOI: 10.1021/acs.jnatprod.0c01307
发表时间: 2021-06-29
影响因子: 5.1
作者:
Hsieh, Meng-Hsuan;Hsiao, George;Lee, Tzong-Huei
通讯作者: Lee, Tzong-Huei