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      Preparative Separation of Phenylethanoid and Secoiridoid Glycosides from Ligustri Lucidi Fructus by High-Speed Counter-Current Chromatography Coupled with Ultrahigh Pressure Extraction

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          Abstract

          Three phenylethanoid glycosides, echinacoside ( 1), salidroside ( 3), and acteoside ( 6), and three secoiridoid glycosides, isonuezhenide ( 2), nuezhenoside G13 ( 4), and specnuezhenide ( 5), have been extracted and separated by a combined method of ultrahigh pressure extraction (UPE) and high-speed counter-current chromatography (HSCCC) from Ligustri Lucidi Fructus. For the UPE, the optimal extraction was developed with conditions including solvent of 90% ethanol, sample to solvent ratio of 1:20 g/mL, pressure of 200 MPa, and time of 2 min, which rendered the yields of compounds 4 and 5 were 15.0 and 78.0 mg/g, respectively. For the HSCCC separation, the strategy of changing flow rates between 1.0 and 2.0 mL/min allowed the acquisition for 2.7 mg of compound 1, 4.5 mg of compound 2, 6.8 mg of compound 3, 5.9 mg of compound 4, 11.2 mg of compound 5, and 2.2 mg of compound 6 in one separation run under the solvent system of ethyl acetate: n-butanol:water (2:1:3, v/ v) from 200 mg of the UPE extract. The structures of these phenylethanoid and secoiridoid glycosides were elucidated by extensive spectroscopic methods.

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          Ultrasound-assisted extraction of oleanolic acid and ursolic acid from Ligustrum lucidum Ait.

          Oleanolic acid and ursolic acid are the main bioactive compounds in fruit of Ligustrum lucidum Ait, which possess anti-inflammatory, antioxidative, antiprotozoal, antimutagenic and anticancer properties. In this study, the ultrasound-assisted extraction of oleanolic acid and ursolic acid from L. lucidum Ait was investigated with HPLC-photodiode array detection. Effects of several experimental parameters, such as type and concentration of extraction solvent, ratio of liquid to material, extraction temperature and extraction time, on extraction efficiencies of oleanolic acid and ursolic acid from L. lucidum were evaluated. The influence of experimental parameters on extraction efficiency of ursolic acid was more significant than that of oleanolic acid. The optimal extraction conditions were 95% ethanol, the ratio of material to liquid at 1:20, and extraction for 10 min at 40°C under ultrasonic irradiation. Under the optimal conditions, the yields of oleanolic acid and ursolic acid were 6.3 ± 0.25 and 9.8 ± 0.30 mg/g, respectively. The results indicated that the ultrasound-assisted extraction is a very useful method for the extraction of oleanolic acid and ursolic acid from L. lucidum. Copyright © 2011 Elsevier B.V. All rights reserved.
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            Antioxidative glucosides from the fruits of Ligustrum lucidum.

            The ethanol extract of the fruits of Ligustrum lucidum was shown to have inhibitory effects on the hemolysis of red blood cells induced by 2,2'-azo-bis-(2-amidinopropane) dihydrochloride. Bioassay-guided analysis led to the isolation of ten secoiridoid glucosides. Two of them were new, lucidumosides C and D. Their structures were elucidated by spectroscopic methods. The other eight compounds were identified as oleoside dimethyl ester, ligustroside, oleuropein, nuezhenide, isonuezhenide, neonuezhenide, lucidumoside A and lucidumoside B. Five compounds, oleoside dimethyl ester, oleuropein, neonuezhenide, lucidumoside B and lucidumoside C, exhibited strong antioxidant effect against hemolysis of red blood cells induced by free radicals.
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              Ligustrum lucidum Ait. fruit extract induces apoptosis and cell senescence in human hepatocellular carcinoma cells through upregulation of p21.

              Nü-zhen-zi, the fruit of Ligustrum lucidum Ait., is one of the most frequently used liver Yin tonifying Chinese herbs for the treatment of liver cancer. However, the effect of Ligustrum lucidum fruit on hepatocarcinoma cells remains unknown. In the present study, we evaluated the effects of a Ligustrum lucidum fruit extract (LLFE) on human hepatocellular carcinoma Bel-7402 cells. The results showed that LLFE inhibited the proliferation of the Bel-7402 cells in a dose- and time-dependent manner. LLFE induced apoptosis in Bel-7402 cells accompanied by activation of caspase-3, -8 and -9. LLFE-induced apoptosis was completely abrogated by a pan caspase inhibitor, Z-VAD-FMK. LLFE treatment also caused a large and flat morphologic cellular change, positive SA-β-gal staining, and G0/G1 phase cell cycle arrest in the Bel-7402 cells, accompanied by upregulation of p21 and downregulation of RB phosphorylation. Specific knockdown of p21 expression by RNA interference partially abrogated LLFE-induced apoptosis, and significantly abrogated LLFE-induced cell senescence. These observations suggest that Nü-zhen-zi is a potential anticancer herb and support the traditional use of Nü-zhen-zi for hepatocarcinoma treatment.
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                Author and article information

                Journal
                Molecules
                Molecules
                molecules
                Molecules
                MDPI
                1420-3049
                18 December 2018
                December 2018
                : 23
                : 12
                : 3353
                Affiliations
                [1 ]Liaoning Institute of Science and Technology, Benxi 117004, China; hfwdd@ 123456163.com (F.H.); chenlilycharming@ 123456126.com (L.C.)
                [2 ]Shandong Key Laboratory of TCM Quality Control Technology, Shandong Analysis and Test Center, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250014, China; 18765878227@ 123456126.com (Q.L.); wangx@ 123456sdas.org (X.W.)
                [3 ]College of Pharmacy, Shandong University of Traditional Chinese Medicine, Jinan 250355, China
                Author notes
                [* ]Correspondence: ljytl7172@ 123456163.com (J.L.); yujinqian87528@ 123456126.com (J.Y.); Tel.: +86-0531-8962-8081 (J.L.); +86-0531-8260-5319 (J.Y.)
                Article
                molecules-23-03353
                10.3390/molecules23123353
                6321428
                30567348
                1125757d-2a79-4999-a18f-0eeaac7a92f5
                © 2018 by the authors.

                Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license ( http://creativecommons.org/licenses/by/4.0/).

                History
                : 21 November 2018
                : 16 December 2018
                Categories
                Article

                high-speed counter-current chromatography,phenylethanoid glycoside,secoiridoid glycoside ligustri lucidi fructus,ultrahigh pressure extraction

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