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Phytochemistry. 2015 Sep;117:123-134. doi: 10.1016/j.phytochem.2015.06.001. Epub 2015 Jun 12.

Anti-viral and cytotoxic norbisabolane sesquiterpenoid glycosides from Phyllanthus emblica and their absolute configurations.

Author information

1
State Key Laboratory of Phytochemistry & Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Lanhei Road 132#, Kunming 650201, People's Republic of China; Chemistry and Chemical Engineering College, Chongqing University, Chongqing 400030, People's Republic of China.
2
State Key Laboratory of Phytochemistry & Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Lanhei Road 132#, Kunming 650201, People's Republic of China; University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China.
3
State Key Laboratory of Phytochemistry & Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Lanhei Road 132#, Kunming 650201, People's Republic of China.
4
State Key Laboratory of Phytochemistry & Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Lanhei Road 132#, Kunming 650201, People's Republic of China. Electronic address: xumin@mail.kib.ac.cn.
5
State Key Laboratory of Phytochemistry & Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Lanhei Road 132#, Kunming 650201, People's Republic of China. Electronic address: zhangyj@mail.kib.ac.cn.

Abstract

In an effort to identify anti-viral and cytotoxic compounds from Phyllanthus spp., 14 highly oxygenated norbisabolane sesquiterpenoids, phyllaemblicins H1-H14, were isolated from the roots of Phyllanthus emblica Linn, along with phyllaemblicins B and C and glochicoccinoside D. Their structures were determined on the basis of detailed spectroscopic analysis and chemical methods. Determination of absolute configurations of these compounds was facilitated by theoretical calculations of electronic circular dichroism (ECD) spectra using time-dependent density functional theory (TDDFT) for the aglycone components, and pre-column derivative/chiral HPLC analysis for the monosaccharides. The known glochicoccinoside D displayed potent activity against influenza A virus strain H3N2 and hand, foot and mouth virus EV71, with IC50 values of 4.5±0.6 and 2.6±0.7 μg/ml, respectively. Phyllaemblicin H1 showed moderate cytotoxicity against human cancer cell lines A-549 and SMMC-7721, with IC50 values of 4.7±0.7 and 9.9±1.3 μM, respectively.

KEYWORDS:

Antiviral; ECD calculation; Euphorbiaceae; Norbisabolane sesquiterpenoid glycosides; Phyllaemblicins; Phyllanthus emblica; Yu Gan Zi

PMID:
26074492
DOI:
10.1016/j.phytochem.2015.06.001
[Indexed for MEDLINE]

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