Guaianolide sesquiterpene lactones from Achillea millefolium L

Hongliang Li; Jun Li; Mengqi Liu; Rongrong Xie; Yi Zang; Jia Li; Haji Akber Aisa

doi:10.1016/j.phytochem.2021.112733

Guaianolide sesquiterpene lactones from Achillea millefolium L

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

Authors

Hongliang Li¹, Jun Li², Mengqi Liu³, Rongrong Xie⁴, Yi Zang³, Jia Li⁵, Haji Akber Aisa⁶

Affiliations

¹ 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.
² 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.
³ State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, China; University of Chinese Academy of Sciences, Beijing, 10049, China.
⁴ State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, China.
⁵ State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, China; University of Chinese Academy of Sciences, Beijing, 10049, China; Open Studio for Druggability Research of Marine Natural Products, Pilot National Laboratory for Marine Science and Technology (Qingdao), Qingdao, 266237, China. Electronic address: jli@simm.ac.cn.
⁶ 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. Electronic address: haji@ms.xjb.ac.cn.

PMID: 33761376
DOI: 10.1016/j.phytochem.2021.112733

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 ¹³C 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.

Keywords: Achillea millefolium L.; Anti-inflammatory; Asteraceae; Guaianolide sesquiterpene lactones; Melaogenesis; Millefoliumins A−G.

MeSH terms

Achillea*
Asteraceae*
China
Lactones / pharmacology
Sesquiterpenes* / pharmacology
Sesquiterpenes, Guaiane

Substances

Lactones
Sesquiterpenes
Sesquiterpenes, Guaiane