Anti-viral and cytotoxic norbisabolane sesquiterpenoid glycosides from Phyllanthus emblica and their absolute configurations. (September 2015)

• Record Type: Journal Article
• Authors: Lv, Jun-Jiang; Yu, Shan; Xin, Ying; Cheng, Rong-Rong; Zhu, Hong-Tao; Wang, Dong; Yang, Chong-Ren; Xu, Min; Zhang, Ying-Jun
• Is Part Of: Phytochemistry. Volume 117(2015:Sep.)
• Page Start: 123
• Page End: 134
• Publication Date: 2015-09
• Subjects: Yu Gan Zi -- Phyllanthus emblica -- Euphorbiaceae -- ECD calculation -- Antiviral -- Norbisabolane sesquiterpenoid glycosides -- Phyllaemblicins; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2015.06.001
• Languages: English
• ISSNs: 0031-9422

Abstract

Graphical abstract: Pre-column derivative/chiral separation/DAD detection and theoretical calculations of ECD spectra using TDDFT were used to determine the absolute configurations of phyllaemblicins H1–H14, with antiviral activities, isolated from P. emblica . Highlights: 14 norbisabolane sesquiterpenoid glycosides were isolated from Phyllanthus emblica. Their structures comprised of sesquiterpenoid aglycones and 14 saccharide moieties. The absolute configurations of the aglycones were established by calculated ECD without hydrolysis. The absolute configurations of saccharides were determined by chiral HPLC analysis. Effects of anti CVB3, EV71, H3N2, HSV-1, and five cancer cell lines were evaluated. 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.