来自箭叶橐吾的具有多样骨架的埃里莫菲烷型倍半萜。

Eremophilane-type sesquiterpenoids with diverse skeletons from Ligularia sagitta.

机构信息

State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University , Tian-shui Road 222, Lanzhou 730000, People's Republic of China.

出版信息

J Nat Prod. 2014 Jun 27;77(6):1329-35. doi: 10.1021/np5003302. Epub 2014 Jun 10.

DOI:10.1021/np5003302

PMID:24913558

Abstract

Five new highly oxygenated eremophilane-type sesquiterpenoids, possessing C19 (1 and 2), C15 (3 and 4), and C14 (8) skeletons, along with eight known eremophilenolides were obtained from the aerial parts of Ligularia sagitta. The absolute configuration of 1 was assigned by X-ray diffraction analysis and that of 3 by ECD spectroscopy. Compounds 1-10 were evaluated for their antibacterial activities against Staphyloccocus aureus, Bacillus subtilis, Escherichia coli, Bacillus cereus, and Erwinia carotovora. Compounds 4 and 5 displayed broad-spectrum inhibitory activity against these bacteria with MIC values of approximately 7.25 μg/mL, followed by 3 and 6 with MIC values in the range of 23.0-125.0 μg/mL. Compounds 3 and 8 showed mild activity against three human tumor cell lines (IC50 ≈ 13 μM). Preliminary structure-activity relationships for these eremophilenolides are reported.

摘要

从箭叶橐吾的地上部分分离得到了 5 个新的高度氧化的半日花烷型倍半萜，具有 C19（1 和 2）、C15（3 和 4）和 C14（8）骨架，以及 8 个已知的埃雷莫芬内酯。通过 X 射线衍射分析确定了 1 的绝对构型，通过 ECD 光谱确定了 3 的绝对构型。对化合物 1-10 进行了抗金黄色葡萄球菌、枯草芽孢杆菌、大肠杆菌、蜡状芽孢杆菌和胡萝卜软腐欧文氏菌的抗菌活性评价。化合物 4 和 5 对这些细菌表现出广谱抑制活性，MIC 值约为 7.25μg/mL，其次是 3 和 6，MIC 值在 23.0-125.0μg/mL 范围内。化合物 3 和 8 对三种人肿瘤细胞系表现出轻微的活性（IC50≈13μM）。报道了这些半日花烷型倍半萜的初步构效关系。