New Monoterpenoids and Polyketides from the Deep-Sea Sediment-Derived Fungus Aspergillus sydowii MCCC 3A00324.

New Monoterpenoids and Polyketides from the Deep-Sea Sediment-Derived Fungus Aspergillus sydowii MCCC 3A00324.
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来自深海沉积物衍生真菌 Aspergillus sydowii MCCC 3A00324 的新单萜和聚酮化合物。

DOI:
10.3390/md18110561
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发表时间:
2020-11-17
期刊:
影响因子:
5.4
通讯作者:
Zhang G
Zhang G
中科院分区:
医学2区
文献类型:
--
作者:
Niu S;Yang L;Chen T;Hong B;Pei S;Shao Z;Zhang G

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通过对深海衍生真菌Aspergillus sydowii MCCC 3A00324次生代谢产物的化学研究,分离出11个化合物(1 - 11),包括1个新化合物(1)和1个新化合物(2),以及2个未描述的多酮化合物(3和4)。代谢产物的结构通过核磁共振和hremsims光谱综合分析,结合13C核磁共振、ECD和构型分配的特定旋转数据的量子化学计算确定。化合物1具有新的单萜类骨架,生物遗传学上可能是由环戊烷环裂解氧化反应后的桂花型单萜类化合物衍生而来。此外,化合物3是α-吡酮衍生物中第一个分别在C-3和C-5上含有两个苯基单元的例子。测定了1-11的抗炎活性。结果表明,化合物6对脂多糖(LPS)激活的BV-2小胶质细胞产生一氧化氮有明显的抑制作用,浓度为10µM时,抑制率为94.4%。此外,还提出了1和2的生物合成途径。
Chemical study of the secondary metabolites of a deep-sea-derived fungus Aspergillus sydowii MCCC 3A00324 led to the isolation of eleven compounds (1–11), including one novel (1) and one new (2) osmane-related monoterpenoids and two undescribed polyketides (3 and 4). The structures of the metabolites were determined by comprehensive analyses of the NMR and HRESIMS spectra, in association with quantum chemical calculations of the 13C NMR, ECD, and specific rotation data for the configurational assignment. Compound 1 possessed a novel monoterpenoid skeleton, biogenetically probably derived from the osmane-type monoperpenoid after the cyclopentane ring cleavage and oxidation reactions. Additionally, compound 3 was the first example of the α-pyrone derivatives bearing two phenyl units at C-3 and C-5, respectively. The anti-inflammatory activities of 1–11 were tested. As a result, compound 6 showed potent inhibitory nitric oxide production in lipopolysaccharide (LPS)-activated BV-2 microglia cells with an inhibition rate of 94.4% at the concentration of 10 µM. In addition, a plausible biosynthetic pathway for 1 and 2 was also proposed.
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