Unprecedented nor-seco-diterpene lactones inhibited osteogenic differentiation of valve interstitial cells.

Bioorg Chem

The First Affiliated Hospital of Shenzhen University, Shenzhen Second People's Hospital, Shenzhen 518035, China; Wu Zhengzhi Academician Workstation, Ningbo College of Health Sciences, Ningbo 315800, China. Electronic address:

Published: December 2024

AI Article Synopsis

  • - The study identifies two new diterpene lactones, eufislactones A and B, isolated from the roots of Euphorbia fischeriana, alongside a new compound and fifteen known derivatives.
  • - The structural analysis of these compounds was performed using various methods including spectroscopy and X-ray diffraction, revealing their unique chemical configurations.
  • - Eufislactone A has shown a significant effect on inhibiting the differentiation of human valvular interstitial cells, indicating its potential to help prevent calcific aortic valve disease.

Article Abstract

The first examples of ent-atisane and ent-isopimarane diterpene lactones with an unusual 2,3-seco-2-nor-tetrahydro-2H-pyran-2-one nucleus, eufislactones A (1) and B (2), were isolated from the roots of Euphorbia fischeriana, together with a new (3) and fifteen known biosynthetic congeners (4-18). Their structures incorporating absolute configurations were elucidated via the comprehensive spectroscopic analyses, electronic circular dichroism (ECD) calculation, and single-crystal X-ray diffraction analyses. Biogenetically, compounds 1 and 2 were constructed by the plausible monomeric precursors, ent-atis-16-ene-3,14-dione (6) and ent-isopimara-8(14),15-dien-3-one (17), respectively, via key Baeyer-Villiger oxidation, decarboxylation, and semi-acetalization reactions to create a unique 2,3-seco-2-nor-tetrahydro-2H-pyran-2-one core. Our bioassays have revealed that eufislactone A (EFA, 1) displayed significant inhibitory effect on the osteogenic differentiation of human valvular interstitial cells (VICs), highlighting its potential as a preventive agent against the progression of human calcific aortic valve disease (CAVD).

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Source
http://dx.doi.org/10.1016/j.bioorg.2024.107837DOI Listing

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