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Isolation, Structural Elucidation of Three New Triterpenoids from the Stems and Leaves of Schisandra chinensis (Turcz) Baill.

ABSTRACT: Schisandra chinensis (Turcz) Baill. is sufficiently well known as a medicinal plant worldwide, which modern research shows has many pharmacological activities such as hepatoprotective, anti-inflammatory effect, potent anti-HIV-1 activity, anti-tumor effect, and activity on the central nervous system. With considerable chemical investigation, three new triterpenoids (1?3), together with four known triterpenoids were isolated from the S. chinensis (Turcz) Baill. Their structures were elucidated by 1D- and 2D-NMR spectroscopic analyses, single-crystal X-ray diffraction and high-resolution mass spectroscopy, which were identified as Schisanlactone I (1), Schinalactone D, (2), Schisanlactone J, (3) Kadsuphilactone B (4), Schisanlactone C (5), Schisphendilactone B (6), and Schinchinenlactone A (7). The cytotoxicity of those compounds (1?7) was tested against Hep-G2 cell lines, but no apparent antitumor activity was observed at 50 µg/mL using MTT method.

SUBMITTER: Qiu F

PROVIDER: S-EPMC6099626 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature

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Isolation, Structural Elucidation of Three New Triterpenoids from the Stems and Leaves of Schisandra chinensis (Turcz) Baill.

Qiu Feng F Liu Han H Duan Huan H Chen Pian P Lu Shao-Juan SJ Yang Guang-Zhong GZ Lei Xin-Xiang XX

Molecules (Basel, Switzerland) 20180704 7

Schisandra chinensis (Turcz) Baill. is sufficiently well known as a medicinal plant worldwide, which modern research shows has many pharmacological activities such as hepatoprotective, anti-inflammatory effect, potent anti-HIV-1 activity, anti-tumor effect, and activity on the central nervous system. With considerable chemical investigation, three new triterpenoids (1⁻3), together with four known triterpenoids were isolated from the S. chinensis (Turcz) Baill. Their s ...[more]

PMID: 29973497

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Project description:According to the potential anti-hepatoma therapeutic effect of Schisandra chinensis polysaccharides presented in previous studies, a bioactive constituent, homogeneous Schisandra chinensis polysaccharide-0-1 (SCP-0-1), molecular weight (MW) circa 69.980 kDa, was isolated and purified. We assessed the efficacy of SCP-0-1 against human hepatocellular liver carcinoma (HepG2) cells to investigate the effects of its antitumour activity and molecular mechanisms. Anticancer activity was evaluated using microscopy, 3-[4,5-dimethyl-2-thiazolyl]-2,5-diphenyltetrazolium bromide (MTT) assay, Hoechst 33258 staining, acridine orange (AO) staining, flow cytometry (FCM), and cell-cycle analysis. SCP-0-1 inhibited the HepG2 cells' growth via inducing apoptosis and second gap/mitosis (G2/M) arrest dose-dependently, with a half maximal inhibitory concentration (IC50) value of 479.63 µg/mL. Western blotting of key proteins revealed the apoptotic and autophagic potential of SCP-0-1. Besides, SCP-0-1 upregulated Bcl-2 Associated X Protein (Bax) and downregulated B-cell leukemia/lymphoma 2 (Bcl-2) in the HepG2 cells. The expression of caspase-3, -8, and -9; poly (ADP-ribose) polymerase (PARP); cytochrome c (Cyt C); tumor protein 53 (p53); survivin; sequestosome 1 (p62); microtubule-associated protein 1 light chain-3B (LC3B); mitogen-activated protein kinase p38 (p38); extracellular regulated protein kinases (ERK); c-Jun N-terminal kinase (JNK); protein kinase B (AKT); and heat shock protein 90 (Hsp90) were evaluated using Western blotting. Our findings demonstrate a novel mechanism through which SCP-0-1 exerts its antiproliferative activity and induces mitochondrial apoptosis rather than autophagy. The induction of mitochondrial apoptosis was attributed to the inhibition of the Hsp90/AKT signalling pathway in an extracellular signal-regulated kinase-independent manner. The results also provide initial evidence on a molecular basis that SCP-0-1 can be used as an anti-hepatocellular carcinoma therapeutic agent in the future.

Project description:Schisandra chinensis (Turcz.) Baill (SC) and Lycium chinense Mill. (LC) are widely distributed in Asia, where the fruit has traditionally been used for medicinal herbs. We previously reported that the roasting process improved the antioxidant and their hangover relieving effects. In this study, we assessed the antioxidant and anti-inflammatory effects of water extract of SC, LC, and a mass ratio 1 : 1 mixture (SL), after roasting in RAW264.7 macrophage cells stimulated with lipopolysaccharide (LPS). Roasted SL (RSL) extracts showed greater enhancement potential than the others, based on the inhibition of NO (nitric oxide) and intracellular reactive oxygen species (ROS) production in RAW264.7 cells. RSL also significantly decreased the proinflammatory markers (e.g., iNOS, COX-2, TNF-α, and IL-1β) and NAD(P)H oxidase (NOX) signaling proteins (i.e., NOX (-1, -2, and -4), p22phox, p47phox, and p67phox). The inflammatory cytokine, tumor necrosis factor-alpha, interferon-1 beta levels, NF-kB, and mitogen-activated kinase activations were also significantly inhibited by RSL treatment. Based on the results of cellular levels, we compared the promotion effects of RSL extract on liver injury mediated by alcohol-induced inflammation and oxidative stress in mice. Mice were fed a Lieber-DeCarli regular liquid alcohol diet with or without SL and RSL extracts for six weeks. Alcohol intake caused liver injury, evidenced by an increase in serum alanine aminotransferase and aspartate aminotransferase activities. Consistent with the results in cell levels, RSL treatment remarkably downregulated ROS and inflammatory factors, as well as their signaling molecules, in serum and tissues. These results suggest that the roasting of SC and LC could potentially elevate the inhibition effect on alcohol-induced inflammation and oxidative stress and consequently prevent alcoholic liver damage. Also, the combination of SC and LC may provide a more synergistic effect than either alone.

Dataset Information

Isolation, Structural Elucidation of Three New Triterpenoids from the Stems and Leaves of Schisandra chinensis (Turcz) Baill.

Publications

Isolation, Structural Elucidation of Three New Triterpenoids from the Stems and Leaves of <i>Schisandra chinensis</i> (Turcz) Baill.

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