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Bioorg Chem. 2018 Dec;81:234-240. doi: 10.1016/j.bioorg.2018.08.029. Epub 2018 Aug 22.

Unusual ent-atisane type diterpenoids with 2-oxopropyl skeleton from the roots of Euphorbia ebracteolata and their antiviral activity against human rhinovirus 3 and enterovirus 71.

Author information

1
College of Pharmacy, Academy of Integrative Medicine, College of Medical Laboratory, The National & Local Joint Engineering Research Center for Drug Development of Neurodegenerative Disease, Dalian Medical University, Dalian 116044, China.
2
The First Affiliated Hospital of Dalian Medical University, No. 222 Zhongshan Road, Dalian 116011, China. Electronic address: lidw87@163.com.
3
College of Pharmacy, Academy of Integrative Medicine, College of Medical Laboratory, The National & Local Joint Engineering Research Center for Drug Development of Neurodegenerative Disease, Dalian Medical University, Dalian 116044, China. Electronic address: maxc1978@163.com.
4
College of Pharmacy, Academy of Integrative Medicine, College of Medical Laboratory, The National & Local Joint Engineering Research Center for Drug Development of Neurodegenerative Disease, Dalian Medical University, Dalian 116044, China. Electronic address: wach_edu@sina.com.

Abstract

Two novel ent-atisane type diterpenoids possessing the extra unusal 2-oxopropyl moiety (1 and 2) and four known analogues have been isolated from the roots of Euphorbia ebracteolata. The structures and absolute configurations of these compounds were determined by extensive spectroscopic data analysis, including 2D NMR, single-crystal X-ray crystallography, 13C NMR calculation, and electronic circular dichroism spectra calculation. Compounds 1 and 2 are the first examples of natural products with ent-atisane type diterpenoids possessing 2-oxopropyl skeleton. Compounds 2, 3, 5, and 6 show antiviral activities against human rhinovirus 3, with IC50 values of 25.27-90.35 μM. Compounds 5 and 6 showed moderate antiviral activities against EV71 at a concentration of 100 μM.

KEYWORDS:

Atisane; Diterpenoids; EV71; Euphorbia ebracteolata; HRV3

PMID:
30153588
DOI:
10.1016/j.bioorg.2018.08.029
[Indexed for MEDLINE]

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