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Spiroconyone A, a new phytosterol with a spiro [5,6] ring system from Conyza japonica

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Abstract

Spiroconyone A (1), the first rearranged phytosterol featuring an unusual spiro [5,6] ring system, and nine known compounds (2–10) were isolated from the aerial parts of Conyza japonica. The structure of 1 was elucidated through spectroscopic methods, and its absolute configuration was determined by single-crystal X-ray diffraction analysis. Enzyme-based assay revealed that spiroconyone A showed weak TDP1 inhibition and compounds 7 and 10 showed TDP1 inhibition with IC50 values of 36 μM and 16 μM, respectively. MTT assay indicated that 7 and 10 showed a strong synergistic effect with the clinical TOP1 inhibitor topotecan in MCF-7 cells. Compound 5 displayed the most potent cytotoxicity against MCF-7 cells with a GI50 value of 3.3 μM. Furthermore, a hypothetical biosynthetic pathway for 1 was proposed. This work provides valuable information that the secondary metabolites from Conyza japonica could be developed as anticancer agents.

Graphical abstract: Spiroconyone A, a new phytosterol with a spiro [5,6] ring system from Conyza japonica

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Article information


Submitted
30 Mar 2020
Accepted
30 Apr 2020
First published
30 Apr 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

Spiroconyone A, a new phytosterol with a spiro [5,6] ring system from Conyza japonica

L. Xiao, Y. Zhang, H. Zhang, D. Li, Q. Gu, G. Tang, Q. Yu and L. An, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB00666A

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