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Highly functionalized cyclohexanone-monocyclic polyprenylated acylphloroglucinols from Hypericum perforatum induce leukemia cell apoptosis

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Abstract

Spirohypolactones A (1) and B (2) and hyperhexanones C–E (3–5), five degraded cyclohexanone-monocyclic polyprenylated acylphloroglucinol (C-MPAP) derivatives were isolated from the stems and leaves of Hypericum perforatum. The structures of these compounds were established by extensive spectroscopic analyses and electronic circular dichroism (ECD) calculations. Compounds 1 and 2 are the first examples of naturally occurring C-MPAPs possessing 2-oxaspiro[4.5]decane spirocyclic skeletons. Compound 5 featured an unusual dodecahydro-4H-oxocino[4,3-g]benzofuran ring system. Notably, compounds 3 and 4 induce apoptosis in the acute myeloid leukemia cell lines NB4 and HL-60 by the activation of caspase-3, and degradation of PARP. The proposed biosynthetic pathways and biological activities are also discussed.

Graphical abstract: Highly functionalized cyclohexanone-monocyclic polyprenylated acylphloroglucinols from Hypericum perforatum induce leukemia cell apoptosis

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Publication details

The article was received on 22 Nov 2018, accepted on 25 Jan 2019 and first published on 31 Jan 2019


Article type: Research Article
DOI: 10.1039/C8QO01268G
Citation: Org. Chem. Front., 2019, Advance Article

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    Highly functionalized cyclohexanone-monocyclic polyprenylated acylphloroglucinols from Hypericum perforatum induce leukemia cell apoptosis

    Y. Guo, Q. Tong, N. Zhang, X. Duan, Y. Cao, H. Zhu, S. Xie, J. Yang, J. Zhang, Y. Liu, Y. Xue and Y. Zhang, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C8QO01268G

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