Sarcomililate A, an Unusual Diterpenoid with Tricyclo[11.3.0.02,16]hexadecane Carbon Skeleton, and Its Potential Biogenetic Precursors from the Hainan Soft Coral Sarcophyton mililatensis
Sarcomililate A, an Unusual Diterpenoid with Tricyclo[11.3.0.02,16]hexadecane Carbon Skeleton, and Its Potential Biogenetic Precursors from the Hainan Soft Coral Sarcophyton mililatensis
复制标题
海南软珊瑚肉藻中一种罕见的三环[11.3.0.0(2,16)]十六烷碳骨架二萜化合物肉瘤素A及其潜在的生物遗传前体
DOI：
10.1021/acs.joc.8b03020
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发表时间：
2019-03-01
影响因子：
3.6
通讯作者：
Guo, Yue-Wei
中科院分区：
文献类型：
--
作者：
Yang, Min;Li, Xiao-Lu;Guo, Yue-Wei
从海南软珊瑚Sarcophyton mililatensis中分离得到一种新的二萜类化合物sarcomilate A（1），具有一个以前未描述的三环[11.3.0.0（2，16）]十六烷骨架，沿着两个新的西松烷类化合物sarcomilatol A和B（2和3），以及两个已知的相关二萜类化合物（4和5）。通过基于残余偶极耦合（RDC）的NMR分析、TDDFT-ECD（ECD =电子圆二色性）计算和Snatzkes方法的组合，明确确定了包括1的绝对构型（AC）在内的完整化学结构。通过与用反常X射线衍射法测定的2的AC进行比较，进一步证实了1的AC。进一步提出了1-3的合理的生物遗传关系。所报道的化合物均对刀豆蛋白A诱导的T淋巴细胞和/或脂多糖（LPS）诱导的B淋巴细胞增殖具有明显的抑制作用。
A novel diterpenoid, sarcomililate A (1), possessing a previously undescribed tricyclo[11.3.0.0(2,16)]hexadecane scaffold, along with two new cembranoids, sarcomililatols A and B (2 and 3), and two known related diterpenoids (4 and 5), was isolated from the Hainan soft coral Sarcophyton mililatensis. The complete chemical structure including absolute configuration (AC) of 1 was unambiguously determined by a combination of residual dipolar coupling (RDC)-based NMR analysis, TDDFT-ECD (ECD = electronic circular dichroism) calculation, and Snatzkes method. The AC of 1 was further confirmed by a comparison with 2, whose AC was determined by anomalous X-ray diffraction. A plausible biogenetic relationship of 1-3 was further proposed. All the reported compounds exhibited interesting inhibitory effects on the ConA-induced T lymphocytes and/or lipopolysaccharide (LPS)-induced B lymphocytes proliferation.