Lemnalemnanes A-C, Three Rare Rearranged Sesquiterpenoids from the Soft Corals Paralemnalia thyrsoides and Lemnalia sp.
Lemnalemnanes A-C, Three Rare Rearranged Sesquiterpenoids from the Soft Corals Paralemnalia thyrsoides and Lemnalia sp.
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Lemnalemnanes A-C，来自软珊瑚 Paralemnalia thyrsoides 和 Lemnalia sp 的三种罕见重排倍半萜类化合物。
DOI：
10.1021/acs.orglett.1c03386
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发表时间：
2021-12-14
期刊：
影响因子：
5.2
通讯作者：
Li, Guoqiang
中科院分区：
文献类型：
--
作者：
Han, Xiao;Wang, Qi;Li, Guoqiang
从海洋软珊瑚Paralemnalia thyrsoides和Lemnalia sp.中分离得到3个新的倍半萜化合物，命名为Lemnalemnanes A-C（1-3），通过1D/2D NMR、HRESIMS、单晶X射线衍射分析（Cu Ka）、Mosher方法和ECD量子化学计算确定了其结构。Lemnalemnane A（1）具有以螺[双环[3.3.1]壬烷呋喃为核心的篮状结构，而Lemnalemnane B（2）和C（3）分别具有不寻常的6/6/5和6/5/5碳骨架。在所提出的生物合成途径中，1-3被怀疑源自相同的前体4-O-脱乙酰基西葫芦素D（4），该化合物从上述两种物种中共分离。此外，柠檬苦烷C（3）在体内表现出较强的促血管生成活性。
Three novel sesquiterpenoids, lemnalemnanes A-C (1-3), were obtained from marine soft corals Paralemnalia thyrsoides and Lemnalia sp. Their structures were determined by 1D/2D NMR spectroscopy, HRESIMS, single-crystal X-ray diffraction analysis (Cu Ka), Mosher's method, and ECD quantum chemistry calculations. Lemnalemnane A (1) possessed an intriguing basket-like structure with a spiro[bicyclo[3.3.1]nonanefuran core, while lemnalemnanes B (2) and C (3) exhibited unusual 6/6/5 and 6/5/5 carbon skeletons, respectively. In the proposed biosynthesis pathway, 1-3 were suspected to originate from the same precursor, 4-O-deacetylparalemnolin D (4), a compound coisolated from both aforementioned species. Furthermore, lemnalemnane C (3) exhibited strong in vivo promoting-angiogenesis activity.