Modified Fusicoccane-Type Diterpenoids from Alternaria brassicicola

Modified Fusicoccane-Type Diterpenoids from Alternaria brassicicola
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来自芸苔链格孢的改良 Fusicoccane 型二萜类化合物

DOI:
10.1021/acs.jnatprod.0c00165
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发表时间:
2020-06-26
影响因子:
5.1
通讯作者:
Zhang, Yonghui
Zhang, Yonghui
中科院分区:
生物学2区
文献类型:
--
作者:
Li, Fengli;Lin, Shuang;Zhang, Yonghui

文献摘要

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从芸苔链格孢菌(Alternaria brassicicicola)中分离得到7个新的改性镰刀菌烷型二萜化合物(1-7)和2个已知的同类化合物(8和9)。结合NMR和HRESIMS数据、C-13 NMR计算和DP ~(4+)概率分析确定了它们的结构,并通过ECD计算和单晶X射线衍射(Cu K α)确定了1-5的绝对构型。化合物1-3属于罕见的16-去甲-二环戊二烯并[a,d]-环辛烷二萜类化合物,化合物2和4代表具有两个先前未描述的四环5/6/6/5环系统的fusicoccane-type二萜类化合物的第一个实例,而化合物5具有先前未描述的四环5/8/5/3环系统。化合物7具有中度抗炎性,化合物2、3、5和7具有弱细胞毒性。
Seven new modified fusicoccane-type diterpenoids (1-7), together with two known congeners (8 and 9), were obtained from Alternaria brassicicola. Their structures were elucidated from a combination of NMR and HRESIMS data and C-13 NMR calculation as well as DP4+ probability analyses, and the absolute configurations of 1-5 were determined by ECD calculation and single-crystal X-ray diffraction (Cu K alpha). Compounds 1-3 belong to a rare class of 16-nor-dicyclopenta[a,d]-cyclooctane diterpenoids, and compounds 2 and 4 represent the first examples of fusicoccane-type diterpenoids featuring two previously undescribed tetracyclic 5/6/6/5 ring systems, while compound 5 features a previously undescribed tetracyclic 5/8/5/3 ring system. Compound 7 was moderately anti-inflammatory, and compounds 2, 3, 5, and 7 were weakly cytotoxic.