Wang Xing, Peng Xia, Tang Chunping, Zhou Shuaizhen, Ke Chang-Qiang, Liu Yueling, Yao Sheng, Ai Jing, Ye Yang
State Key Laboratory of Drug Research and Natural Products Chemistry Department, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, People's Republic of China.
University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China.
J Nat Prod. 2021 May 28;84(5):1626-1637. doi: 10.1021/acs.jnatprod.1c00177. Epub 2021 May 19.
Fourteen new eudesmane sesquiterpenoids (, -, -) and seven known analogues were isolated from the whole plant of . Their structures were elucidated by spectroscopic data analysis and comparison with published NMR data, and their absolute configurations were confirmed by X-ray diffraction experiments and TDDFT ECD calculation. Compounds - were identified as eudesmane acids, which represent a kind of lactone ring-opening eudesmane-type sesquiterpenes with an acetoxyl or a hydroxy group attached to C-9. Compounds and , and , and and are three pairs of epimers isomerized at C-3, C-5, and C-11, respectively. Compounds -, -, -, and could influence the proinflammatory phenotype of the M1 macrophage. Among them, compounds , , , , , and consistently exhibited anti-inflammatory effects, as evidenced by downregulating classic pro-inflammatory cytokines TNF-α, IL-12, IL-6, and IFN-γ in LPS-induced primary bone marrow derived M1 macrophages.
从[植物名称]全草中分离得到14个新的桉叶烷倍半萜([化合物编号1]、[化合物编号2]、[化合物编号3])和7个已知类似物。通过光谱数据分析并与已发表的核磁共振数据进行比较来阐明它们的结构,通过X射线衍射实验和TDDFT ECD计算确定它们的绝对构型。化合物[化合物编号1] - [化合物编号3]被鉴定为桉叶烷酸,它们是一类内酯环开环的桉叶烷型倍半萜,在C - 9位连接有一个乙酰氧基或一个羟基。化合物[化合物编号4]与[化合物编号5]、[化合物编号6]与[化合物编号7]、[化合物编号8]与[化合物编号9]分别是在C - 3、C - 5和C - 11位异构的三对对映异构体。化合物[化合物编号10] - [化合物编号13]、[化合物编号14]、[化合物编号15]和[化合物编号16]可影响M1巨噬细胞的促炎表型。其中,化合物[化合物编号10]、[化合物编号11]、[化合物编号12]、[化合物编号13]、[化合物编号14]和[化合物编号15]持续表现出抗炎作用,这在脂多糖诱导的原代骨髓来源的M1巨噬细胞中下调经典促炎细胞因子TNF -α、IL - 12、IL - 6和IFN -γ得到了证实。