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Tricarabrols A–C, three anti-inflammatory sesquiterpene lactone trimers featuring a methylene-tethered linkage from Carpesium faberi

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Abstract

Tricarabrols A–C (1–3), three sesquiterpene lactone trimers, were identified from Carpesium faberi. Tricarabrols A and B are a pair of stereoisomers possessing a novel C44 skeleton featuring a methylene-tethered linkage among the sesquiterpene scaffolds. Besides the unique linkage of the cyclopentane ring, tricarabrol C also manifests a methylene bridge. Their full structures were established on the basis of spectroscopic data and further confirmed by computational methods. The biosynthetic pathways involving the Alder-ene reaction, [3 + 2] cycloaddition, and Michael addition reaction were proposed. Tricarabrols A and B (1–2) significantly inhibited the nitric oxide production on lipopolysaccaride-stimulated RAW264.7 macrophages with IC50 values of 2.90 and 4.52 μM, respectively, compared with the positive control indomethacin. Further studies indicated that the anti-inflammatory effect of tricarabrol A was mediated through inhibiting the phosphorylation and nuclear translocation of nuclear factor-κB.

Graphical abstract: Tricarabrols A–C, three anti-inflammatory sesquiterpene lactone trimers featuring a methylene-tethered linkage from Carpesium faberi

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Article information


Submitted
21 Jan 2020
Accepted
19 Apr 2020
First published
22 Apr 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Tricarabrols A–C, three anti-inflammatory sesquiterpene lactone trimers featuring a methylene-tethered linkage from Carpesium faberi

J. Yuan, X. Wen, C. Ke, T. Zhang, L. Lin, S. Yao, J. D. Goodpaster, C. Tang and Y. Ye, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO00093K

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