从白花蒿中提取的愈创木薁型倍半萜内酯

Guaianolide sesquiterpene lactones from Achillea millefolium L.

机构信息

State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, And Key Laboratory of Plant Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi, 830011, China; University of Chinese Academy of Sciences, Beijing, 10049, China.

出版信息

Phytochemistry. 2021 Jun;186:112733. doi: 10.1016/j.phytochem.2021.112733. Epub 2021 Mar 21.

DOI:10.1016/j.phytochem.2021.112733

PMID:33761376

Abstract

Seven undescribed guaianolide sesquiterpene lactones, millefoliumins A-G, and five known analogues were isolated from the whole plant of Achillea millefolium L. growing in Xinjiang, China. Their structures were elucidated by analysis of spectroscopic data and comparison with literatures. The absolute configurations of millefoliumins A-G were determined by single-crystal X-ray crystallography, ECD data analysis along with quantum-chemical ECD calculations. The X-ray crystal structures of 8α-angeloxy-1β,2β,4β,5β-diepoxy-10β-hydroxy-6βH,7αH,11βH-12,6α-guaianolide and 8α-angeloxy-4α,10β-dihydroxy-2-oxo-6βH,7αH,11βH-1(5)-guaien-12,6α-olide were reported for the first time, and the full C NMR data of malaphyllidin were attributed for the first time. Millefoliumins F and G, and austricin could improve the melaogenesis by increasing the melanin content and tyrosinase activity of B16 melanoma cells. Millefoliumins A, C and D, and austricin showed anti-inflammatory activity against the NO production in LPS-induced RAW264.7 cells.

摘要

从中国新疆生长的蓍草全草中分离得到了 7 种未描述的愈创木烷型倍半萜内酯，即 milefoliumins A-G，以及 5 种已知类似物。通过分析光谱数据并与文献进行比较，确定了它们的结构。通过单晶 X 射线晶体学、ECD 数据分析和量子化学 ECD 计算确定了 milefoliumins A-G 的绝对构型。首次报道了 8α-当归酰氧基-1β,2β,4β,5β-环氧-10β-羟基-6βH,7αH,11βH-12,6α-愈创木内酯和 8α-当归酰氧基-4α,10β-二羟基-2-氧代-6βH,7αH,11βH-1(5)-愈创木-12,6α-内酯的 X 射线晶体结构，并首次对 malaphyllidin 的全 C NMR 数据进行了归属。 milefoliumins F 和 G 以及 austricin 可以通过增加 B16 黑色素瘤细胞中的黑色素含量和酪氨酸酶活性来改善黑色素生成。 milefoliumins A、C 和 D 以及 austricin 对 LPS 诱导的 RAW264.7 细胞中 NO 产生具有抗炎活性。