Guaianolide sesquiterpene lactones from Achillea millefolium L.

Mar 25, 2021

Contributor: Hongliang Li,Jun Li,Mengqi Liu,Rongrong Xie,Yi Zang,Jia Li,Haji Akber Aisa

Guaianolide sesquiterpene lactones from Achillea millefolium L.

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.
Copyright © 2021 Elsevier Ltd. All rights reserved.

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About The Expert

Hongliang Li

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.

Jun Li

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.

Mengqi Liu

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.

Rongrong Xie

State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, China.

Yi Zang

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.

Jia Li

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.

Haji Akber Aisa

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.

References

PubMed