A new hexacyclic triterpene acid from the roots of Euscaphis japonica and its inhibitory activity on triglyceride accumulation
Graphical abstract
Introduction
Euscaphis japonica is a deciduous small arbor or shrub that is mainly distributed in the south of the Yangtze River in China, Japan and Korea; the leaves, flowers, fruits and roots have been used as a traditional Chinese medicine for the relieve rheumatism, detumescence and analgesia properties, respectively [1], [2]. Previous pharmacological research reported that the methanol extract of E. japonica possesses anti-inflammatory [3], anti-hepatic fibrotic activity [4] and downregulating lip genesis properties [5]. A variety of compounds, such as flavonoid glucosides [6], triterpenes [7], [8], lactones [9], ellagitannin and tetraketide [10] have been reported from the acrial part of this plant. To date, however, there have been no reports focused on the roots of this herb. Therefore, we attempted to investigate the active constituents and a new hexacyclic triterpene acid named (12R,13S)-3-methoxy-12,13-cyclo-taraxerene-2,14-diene-1-one-28-oic acid (1), together with a known compound 3,7-dihydroxy-5-octanolide (2) (Fig. 1), was isolated from the roots of this herb. Triterpene compounds showed multiple pharmacological activities, such as anti-hepatic fibrotic activity [4] and inhibitory activity on triglyceride accumulation [11]. Based on the exact lipid-lowering effects as selective antagonistic properties on LXRa of E. japonica [5], the lipid-decreasing effect of the new compound 1 in HepG2 cells was evaluated. Herein, we reported the isolation and structure elucidation of the new compound 1. In addition, it exhibited promising inhibitory activity on oleic acid induced triglyceride accumulation in HepG2 cells.
Section snippets
General experimental procedures
Melting points were measured using an X-5 micro melting point apparatus. Optical rotations were determined with an autopol IV-T automatic polarimeter. UV spectra were measured on a Macy UV-1500 ultraviolet and visible spectrophotometer. IR spectra were recorded on a perkin elmer spectrum one as KBr pellets and the absorption frequencies are expressed in reciprocal centimeters (cm− 1).1D and 2D NMR spectra were performed on a Bruker ultrashield™ 400 plus spectrometer at 400 MHz (1H NMR) and 100 MHz
Results and discussion
Compound 1 was crystallized as colorless needles from PE/EtOAc, It showed positive to Liebermann-Burchardt reaction. The UV spectrum indicated absorption maxima at 206 and 249 nm in MeOH. The IR spectrum indicated the presence of carboxyl group (3392, 1724, 1196 cm− 1) and methyl group (2940, 2858, 1454, 1339). The molecular formula was deduced to be C31H44O4 based on the pseudo-molecular ion peak at m/z 479.3149 ([M − H]−, calcd for C31H43O4, 479.3167) in the HR-ESIMS, indicating ten degrees of
Disclosure statement
No potential conflict of interest was reported by the authors.
Acknowledgements
This work was supported by the Program for National Natural Science Foundation of China (No. 81560703).
References (17)
- et al.
Selective LXRalpha inhibitory effects observed in plant extracts of MEH184 (Parthenocissua tricuspidata) and MEH185 (Euscaphis japonica)
Biochem. Biophys. Res. Commun.
(2006) - et al.
Four new triterpenes and triterpene glycosides from the leaves of Ilex latifolia and their inhibitory activity on triglyceride accumulation
Fitoterapia
(2015) - et al.
Triterpenoids from Salvia przewalskii
Phytochemistry
(1988) - et al.
Acidic triterpenoids from Lithocarpus attenuata
Phytochemistry
(1975) Flora of China Editorial Committee of Chinese Academy of Sciences
(1981)- (2004)
- et al.
Inhibitory constituents of Euscaphis japonica on lipopolysaccharide-induced nitric oxide production in BV2 microglia
Planta Med.
(2007) - et al.
Antifibrotic activity of triterpenoids from the aerial parts of Euscaphis japonica on hepatic stellate cells
J. Enzyme Inhib. Med. Chem.
(2009)
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2021, Studies in Natural Products ChemistryCitation Excerpt :Kadlongilactone A and B inhibit human tumor cells. However, euscaphic acid C and D molecule were found to be cytotoxic against cancer cell lines [44,46,47]. A taraxerene-type hexacyclic triterpenoid (12R,13S)-3-methoxy-12,13-cyclotaraxerene-2,14-diene-1-one-28-oic acid of Euscaphis japonica showed inhibitory effect on oleic acid-induced triglyceride accumulation in HepG2 cells [47].
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