Issue 7, 2018

Tagalide A and tagalol A, naturally occurring 5/6/6/6- and 5/6/6-fused cyclic dolabrane-type diterpenes: a new insight into the anti-breast cancer activity of the dolabrane scaffold

Abstract

Tagalide A (1) and tagalol A (2), representing dolabrane-type diterpenes with unprecedented ring-A/B/C/D- and ring-A/B/C-fused cores (vii–viii), respectively, were isolated from the Chinese mangrove, Ceriops tagal. The relative and absolute configurations of these dolabranes were unambiguously established by HRESIMS, extensive NMR investigations, and quantum-chemical 13C NMR and ECD calculations. Most notably, 1 exhibited cytotoxicities against triple-negative breast cancer (TNBC) cell lines, MD-MBA-453 (IC50 = 1.73 μM) and MD-MBA-231 (IC50 = 8.12 μM). Investigation of the mechanisms on MD-MBA-453 cells revealed that 1 induces ROS-mediated apoptosis and cell-cycle arrest in the G2/M phase. It suppresses the phosphorylation of JAK2 and STAT3, but enhances that of AKT and ERK. The 5,6-dihydrobenzofuran-2(4H)-one-7-carbaldehyde moiety of 1 is hitherto the most potent anticancer pharmacophore for the ring-A-centred western part of the dolabrane scaffold against the above-mentioned TNBC cells.

Graphical abstract: Tagalide A and tagalol A, naturally occurring 5/6/6/6- and 5/6/6-fused cyclic dolabrane-type diterpenes: a new insight into the anti-breast cancer activity of the dolabrane scaffold

Supplementary files

Article information

Article type
Research Article
Submitted
05 Jan 2018
Accepted
27 Jan 2018
First published
29 Jan 2018

Org. Chem. Front., 2018,5, 1176-1183

Tagalide A and tagalol A, naturally occurring 5/6/6/6- and 5/6/6-fused cyclic dolabrane-type diterpenes: a new insight into the anti-breast cancer activity of the dolabrane scaffold

X. Zhang, Y. Yang, J. Liu, L. Shen, Z. Shi and J. Wu, Org. Chem. Front., 2018, 5, 1176 DOI: 10.1039/C8QO00010G

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