scholarly journals Bioactivity-Guided Separation of Potential D2 Dopamine Receptor Antagonists from Aurantii Fructus based on Molecular Docking Combined with High-Speed Counter-Current Chromatography

Molecules ◽  
2018 ◽  
Vol 23 (12) ◽  
pp. 3135 ◽  
Author(s):  
Yingjie He ◽  
Shihao Zhu ◽  
Changqiao Wu ◽  
Ying Lu ◽  
Qi Tang
Keyword(s):  
Acetic Acid ◽  
Dopamine Receptor ◽  
Crude Extract ◽  
High Speed ◽  
Solvent System ◽  
Published Data ◽  
D2 Dopamine Receptor ◽  
Chemical Structures ◽  
Dopamine Receptor Antagonists ◽  
Counter Current

The typical compounds of Aurantii fructus (AF) reported in previous research were screened for their high antagonistic ability on the D2 dopamine receptor (D2R) in silico, and then bioactivity-guided separation was undertaken on the potential D2R antagonists from AF using high-speed counter-current chromatography (HSCCC). Three flavanones, two polymethoxyflavonoids, and three coumarins were effectively isolated from ethanol extracts of Aurantii fructus (AF) by the use of a two-step HSCCC method, and their chemical structures were identified by mass spectrometry, 1H-NMR, and 13C-NMR and compared with published data. Firstly, crude extract of 70% ethanol eluent (150 mg) was isolated by HSCCC using an n-hexane−ethyl acetate−n-butanol−methanol−0.05% acetic acid (1:3:1.8:1:5, v/v/v/v/v) solvent system, and compounds 1 (naringin, 28 mg), 2 (neohesperidin, 13 mg), 3 (meranzin, 5 mg) and 4 (poncirin, 3 mg) were successfully isolated with 98.5%, 95.1%, 97.7%, and 92.4% purity, respectively. Then, the crude extract of 95% ethanol eluent (120 mg) was isolated by n-hexane−n-butanol−ethanol (methanol)−0.05% acetic acid (2:0.6:1:3, v/v/v/v) solvent system and compounds 3 (meranzin, 3 mg), 5 (meranzin hydrate, 4 mg), 6 (isomeranzin, 6 mg), 7 (nobiletin, 10 mg), and 8 (tangeretin, 7 mg) were successfully isolated with 95.8%, 98.5%, 95.1%, 92.4%, and 97.7% purity, respectively. Naringenin, a parent structure of naringin with the excellent binding score of −9.3 kcal/mol, was completely in conjunction with the active site of D2R, indicating that it is critical for the treatment of gastrointestinal dysfunction. The results indicated that the bioactivity-guided method is practical for the effective separation of active compounds from natural resources.

HSCCC Separation of Three Main Compounds from the Crude Extract of Dracocephalum Tanguticum by Using Dimethyl Sulfoxide as Cosolvent

2020 ◽  
Author(s):  
Xue Yang ◽  
Yongling Liu ◽  
Tao Chen ◽  
Nana Wang ◽  
Hongmei Li ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Ethyl Acetate ◽  
Dimethyl Sulfoxide ◽  
Efficient Method ◽  
Crude Extract ◽  
High Speed ◽  
Glacial Acetic Acid ◽  
Butyl Alcohol ◽  
Preparative Hplc ◽  
Counter Current

Abstract Separation of natural compounds directly from the crude extract is a challenging work for traditional column chromatography. In the present study, an efficient method for separation of three main compounds from the crude extract of Dracocephalum tanguticum has been successfully established by high-speed counter-current chromatography (HSCCC). The crude extract was directly introduced into HSCCC by using dimethyl sulfoxide as cosolvent. Ethyl acetate/n-butyl alcohol/0.3% glacial acetic acid (4: 1: 5, v/v) system was used and three target compounds with purity higher than 80% were obtained. Preparative HPLC was used for further purification and three target compounds with purity higher than 98% were obtained. The compounds were identified as chlorogenic acid, pedaliin and pedaliin-6″-acetate.

scholarly journals Efficient Preparation of Bafilomycin A1 from Marine Streptomyces lohii Fermentation Using Three-Phase Extraction and High-Speed Counter-Current Chromatography

Marine Drugs ◽  
2020 ◽  
Vol 18 (6) ◽  
pp. 332
Author(s):  
Ye Yuan ◽  
Xiaoping He ◽  
Tingting Wang ◽  
Xingwang Zhang ◽  
Zhong Li ◽  
...  
Keyword(s):  
Crude Extract ◽  
High Speed ◽  
Solvent System ◽  
Bafilomycin A1 ◽  
Middle Phase ◽  
Two Phase ◽  
Rapid Separation ◽  
Lower Phase ◽  
Three Phase ◽  
Counter Current

An efficient strategy was developed for the rapid separation and enrichment of bafilomycin A1 (baf A1) from a crude extract of the marine microorganism Streptomyces lohii fermentation. This strategy comprises liquid−liquid extraction (LLE) with a three-phase solvent system (n-hexane–ethyl acetate–acetonitrile–water = 7:3:5:5, v/v/v/v) followed by separation using high-speed counter-current chromatography (HSCCC). The results showed that a 480.2-mg fraction of baf A1-enriched extract in the middle phase of the three-phase solvent system was prepared from 4.9 g of crude extract after two consecutive one-step operations. Over 99% of soybean oil, the main hydrophobic waste in the crude extract, and the majority of hydrophilic impurities were distributed in the upper and lower phase, respectively. HSCCC was used with a two-phase solvent system composed of n-hexane–acetonitrile–water (15:8:12, v/v/v) to isolate and purify baf A1 from the middle phase fraction, which yielded 77.4 mg of baf A1 with > 95% purity within 90 min. The overall recovery of baf A1 in the process was determined to be 95.7%. The use of a three-phase solvent system represents a novel strategy for the simultaneous removal of hydrophobic oil and hydrophilic impurities from a microbial fermentation extract.

scholarly journals Preparative isolation and purification of seven compounds from Hibiscus mutabilis L. leaves by two-step high-speed counter-current chromatography

2015 ◽  
Vol 21 (2) ◽  
pp. 331-341 ◽  
Author(s):  
Zhuoni Hou ◽  
Xianrui Liang ◽  
Feng Su ◽  
Weike Su
Keyword(s):  
Ethyl Acetate ◽  
High Speed ◽  
Solvent System ◽  
Ionization Mass ◽  
Two Phase ◽  
Purification Method ◽  
Isolation And Purification ◽  
Chemical Structures ◽  
13C Nuclear Magnetic Resonance ◽  
Counter Current

Seven compounds from Hibiscus mutabilis L. leaves were first successfully achieved by two-step high-speed counter-current chromatography with two-phase solvent system composed of n-butanol-ethyl acetate-water (1:6:9, v/v/v) and n-hexane-ethyl acetate-methanol-water (3:5:3:5, v/v/v/v/). The critical experimental parameters of first-step separation were optimized with response surface methodology as follows: flow rate was 1.1 mL/min, revolution speed was 800 rpm and temperature was 30?C. Under the optimal conditions, around 5.0 mg of salicylic acid, 13.6 mg of rutin, 5.5 mg of genistein were obtained in 100 mg crude sample. Then, 9.2 mg of potengriffioside A, 4.7 mg of kaempferol 3-O-rutinoside, 3.0 mg of steppogenin and 2.5 mg of emodin were obtained by second-step separation. The purities of the seven compounds determined by UPLC were 96.2%, 93.8%, 95.4%, 94.3%, 98.0%, 94.1% and 90.8%, respectively. Their chemical structures were identified by electron spray ionization mass spectroscopy (ESI-MS) and 1H, 13C nuclear magnetic resonance (NMR). Furthermore, compound steppogenin and genistein were first reported from Hibiscus mutabilis L. The purification method was simple, efficient and evaded tedious separation process.

scholarly journals Isolation and purification of lignans from Schisandra chinensis by combination of silica gel column and high-speed counter-current chromatography

2013 ◽  
Vol 19 (3) ◽  
pp. 435-440
Author(s):  
Yu Sun ◽  
Shuangshuang Xu ◽  
Yanling Geng ◽  
Xiao Wang ◽  
Tianyou Zhang
Keyword(s):  
Ethyl Acetate ◽  
Petroleum Ether ◽  
Silica Gel ◽  
High Speed ◽  
Solvent System ◽  
Schisandra Chinensis ◽  
Two Phase ◽  
Chemical Structures ◽  
Gomisin A ◽  
Counter Current

Silica gel column combined with high-speed counter-current chromatography separation was successfully applied to the separation of schizandrin (I), angeloylgomisin H (II), gomisin A (III), schisantherin C (IV), deoxyschizandrin (V), ?-schisandrin (VI) and schisandrin C (VII) from the fruits of Schisandra chinensis (Turcz.) Baillon. The petroleum ether extracts of the fruits of S. chinensis were pre-separated first on a silica gel column and divided into two fractions as sample 1 and sample 2. 260 mg of sample 1 was separated by HSCCC using petroleum ether-ethyl acetate-methanol-water (10:8:10:8, v/v) as the two-phase solvent system and 18.2 mg of schizandrin, 15.7 mg of angeloylgomisin H, 16.5 mg of gomisin A and 16.7 mg of schisantherin C were obtained. 230 mg of sample 2 was separated using petroleum ether-ethyl acetate-methanol-water (10:0.5:10:1, v/v) as the two-phase solvent system and 19.7 mg of deoxyschizandrin, 23.4 mg of ?-schisandrin and 18.2 mg of schisandrin C were obtained. The purities of the separated compounds were all over 94% as determined by HPLC. The chemical structures of these compounds were confirmed by ESI-MS and 1H NMR.

scholarly journals Separation of avermectin components from Streptomyces avemitilis extraction using high-speed counter-current chromatography

2013 ◽  
Vol 19 (4) ◽  
pp. 563-571 ◽  
Author(s):  
Weike Su ◽  
Zhuoni Hou ◽  
Xianrui Liang
Keyword(s):  
High Speed ◽  
Solvent System ◽  
Ionization Mass ◽  
Two Phase ◽  
Preparative Scale ◽  
Chemical Structures ◽  
Peak Resolution ◽  
Ionization Mass Spectroscopy ◽  
13C Nuclear Magnetic Resonance ◽  
Counter Current

Three compounds of antibiotics-avermectins from fertilizing product of Streptomyces avemitilis are achieved by high-speed counter-current chromatography (HSCCC) with a two-phase solvent system composed of n-hexane-ethyl acetate-methanol-water (6:4:5:5, v/v) on a preparative scale. The separation condition was: 1.5 mL/min (0 to 200 min) and 2.0 mL/min (200 to the end), 900 rpm and 20?C based on the peak resolution. About 11.9 mg of avermectin B1a, 1.0 mg of avermectin B1b and 9.6 mg of avermectin B2a from 50 mg of crude extract were obtained by one-step separation. The purities of the three compounds determined by HPLC were 99.7%, 96.2% and 97.6%, respectively. Their chemical structures were identified by electron spray ionization mass spectroscopy (ESI-MS), 1H, 13C nuclear magnetic resonance (NMR).

scholarly journals Preparative Separation of Four Major Bufadienolides from the Chinese Traditional Medicine, Chansu, Using High-Speed Counter-Current Chromatography

2010 ◽  
Vol 5 (7) ◽  
pp. 1934578X1000500 ◽  
Author(s):  
Xiu Lan Xin ◽  
Junying Liu ◽  
Xiao Chi Ma ◽  
Qing Wei ◽  
Li Lv ◽  
...  
Keyword(s):  
High Speed ◽  
Solvent System ◽  
Two Phase ◽  
Isolation And Purification ◽  
H Nmr ◽  
Chemical Structures ◽  
One Step ◽  
Counter Current ◽  
Chloroform Methanol ◽  
C Nmr

A preparative, high-speed, counter-current chromatographic (HSCCC) method for the isolation and purification of bufadienolides from Chansu was successfully developed by using stepwise elution with a two-phase solvent system composed of n-hexane: chloroform: methanol: water (4:1:2.5:5 and 4:1:4:5, v/v). A total of 7.5 mg of cinobufotalin (1), 8.0 mg of bufalin (2), 14.0 mg of cinobufagin (3) and 9.5 mg of resibufogenin (4) were obtained in a one-step separation from 80 mg of the crude extract with purities of 93.2%, 98.7%, 99.2%, and 99.4%, respectively. The chemical structures were determined from 1H NMR and 13C NMR spectroscopic data.

scholarly journals Quick Preparative Separation of Natural Naphthopyranones with Antioxidant Activity by High-Speed Counter-Current Chromatography

2002 ◽  
Vol 57 (11-12) ◽  
pp. 1051-1055 ◽  
Author(s):  
Gilda G. Leitão ◽  
Suzana G. Leitão ◽  
Wagner Vilegas
Keyword(s):  
Antioxidant Activity ◽  
Ethyl Acetate ◽  
High Speed ◽  
Ethanolic Extract ◽  
Solvent System ◽  
Spectrophotometric Assay ◽  
Preparative Separation ◽  
Dpph Radical ◽  
Preparative Scale ◽  
Counter Current

The natural naphthopyranones paepalantine (1), paepalantine-9O-β-ᴅ-glucopyranoside (2) and paepalantine-9-O-β-ᴅ-allopyranosyl-(1→6)-O-β-ᴅ-glucopyranoside (3) were separated in a preparative scale from the ethanolic extract of the capitula of Paepalanthus bromelioides by high-speed counter-current chromatography (HSCCC). The solvent system used was composed of water-ethanol-ethyl acetate-hexane (10:4 : 10:4, v/v/v/v). This technique led to the separation of the three different naphthopyranone glycosides in pure form in approximately 7 hours. Paepalantine showed a good antioxidant activity when assayed by the DPPH radical spectrophotometric assay.

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