Ophiobolin Sesterterpenoids and Farnesylated Phthalide Derivatives from the Deep Sea Cold-Seep-Derived Fungus Aspergillus insuetus SD-512
Ophiobolin Sesterterpenoids and Farnesylated Phthalide Derivatives from the Deep Sea Cold-Seep-Derived Fungus Aspergillus insuetus SD-512
复制标题
DOI：
10.1021/acs.jnatprod.0c00860
复制
发表时间：
2020-12-24
影响因子：
5.1
通讯作者：
Wang, Bin-Gui
中科院分区：
文献类型：
--
作者：
Chi, Lu-Ping;Li, Xiao-Ming;Wang, Bin-Gui
从1331 m深海冷沉沉积物中提取的猪曲霉SD-512培养液中分离鉴定了3个新的蛇烟碱酯萜类化合物(6R)-16,17,21,21- o -四氢蛇烟碱酯G (1), (6R)-16,17-二氢蛇烟碱酯H(2)和(5S,6S)-16,17-二氢蛇烟碱酯H(3)，以及3个新的法尼基邻苯二甲酸衍生物法尼基甲呋喃酮D-F（9-11）和5个已知的蛇烟碱类似物（4-8）。其中，化合物9-11是罕见的通过醚键与法尼基基团相连的邻苯酞衍生物。它们的结构是在详细解释核磁共振光谱和质谱数据的基础上确定的。通过x射线晶体学分析、ECD计算和DP4+概率分析确定了化合物1-4的结构，建立了化合物1-4的相对构型和绝对构型。化合物3和9-11表现出广谱抗菌活性，其药效差异可能与结构修饰有关。这是首次报道从深海冷液衍生的真菌中获得次生代谢物。
Three new ophiobolin sesterterpenoids, (6R)-16,17,21,21-O-tetrahydroophiobolin G (1), (6R)-16,17-dihydroophiobolin H (2), and (5S,6S)-16,17-dihydroophiobolin H (3), and three new farnesylated phthalide derivatives farnesylemefuranones D-F ( 9-11), along with five known ophiobolin analogues (4-8), were isolated and identified from the culture extract of Aspergillus insuetus SD-512, a deep-sea-derived fungus obtained from cold seep sediments collected at a depth of 1331 m. Among them, compounds 9-11 are rare examples of phthalide derivatives linked with farnesyl moieties via ether bonds. Their structures were established on the basis of detailed interpretation of the NMR spectroscopic and mass spectrometric data. X-ray crystallographic analysis, ECD calculations, and DP4+ probability analysis were performed to confirm the structures and establish the relative and absolute configurations of compounds 1-4. Compounds 3 and 9-11 showed broad-spectrum antibacterial activities, and differences in potencies could be assigned to structural modifications. This is the first report of secondary metabolites obtained from a deep sea cold-seep-derived fungus.