New 30-ketophragmalins with anti-breast cancer activity against MDA-MB-453 cells from the Godavari mangrove, Xylocarpus moluccensis (Lam.) M. Roem
2018
Zhang, Min | Shi, Zhi | Liu, Junjun | Shen, Li | Wu, Jun
30-Ketophragmalins are a small group of limonoids. To date, only 21 ones have been exclusively reported from the mangrove, Xylocarpus moluccensis (Lam.) M. Roem. In this paper, three new 30-ketophragmalins, named godavarins L-N (1-3), were obtained from the seeds of X. moluccensis, collected in the mangrove swamp of Godavari estuary, Andhra Pradesh, India, together with a mexicanolide, named godavarin O (4). The structures of these compounds, including absolute configurations of godavarins L-M (1-2), were determined on the basis of HRESIMS, extensive 1D and 2D NMR spectroscopic data, and electronic circular dichroism (ECD) quantum-chemical calculations. Compounds 1, 2, and 4 contain a Δ⁸,¹⁴ double bond, whereas 3 possesses Δ⁸,⁹, Δ¹⁴,¹⁵ conjugated double bonds. Two 30-ketophragmalins, viz.1 and 3, exhibited antitumor activities against the triple-negative breast cancer MDA-MB-453 cells with IC₅₀ values of 2.1 ± 0.06 and 9.0 ± 1.0 μM, respectively. This is the first report of the anti-breast cancer activity of 30-ketophragmalins.
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