Target guided isolation of potential tyrosinase inhibitors from Otholobium pubescens (Poir.) J.W. Grimes by ultrafiltration, high-speed countercurrent chromatography and preparative HPLC

Zuo, Guanglei; Wang, Zhiqiang; Quispe, Yanymee N. Guillen; Hwang, Seung Hwan; Kim, Hyun Yong; Kang, Beom Goo; Lim, Soon Sung

doi:10.1016/j.indcrop.2019.03.045

Cited by 24 publications

(13 citation statements)

References 32 publications

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“…The selection of the polarity gradient solvent systems mainly depended on the suitable partition coefficients ( K value) and settling times the solvent systems offered. The K values were calculated as previously described [ 59 ]. Each solvent system was paired with equal volumes of solvent methanol/water (1:5, v / v ) and individual n -hexane/ethyl acetate (3:5, v / v ), n -hexane/ethyl acetate (2:5, v / v ), n -hexane/ethyl acetate (1:5, v / v ), ethyl acetate, and ethyl acetate/ n -butanol (4:1, v / v ) was partitioned to the upper layer and lower layer.…”

Section: Methodsmentioning

confidence: 99%

Efficient Separation of Phytochemicals from Muehlenbeckia volcanica (Benth.) Endl. by Polarity-Stepwise Elution Counter-Current Chromatography and Their Antioxidant, Antiglycation, and Aldose Reductase Inhibition Potentials

et al. 2021

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Muehlenbeckia volcanica (Benth.) Endl. (M. volcanica), native to South America, is a traditional Peruvian medicinal plant that has multi-therapeutic properties; however, no phytochemicals have been identified from it yet. In this study, a five-step polarity-stepwise elution counter-current chromatography (CCC) was developed using methanol/water (1:5, v/v) as the stationary phase and different ratios of n-hexane, ethyl acetate, and n-butanol as mobile phases to separate the compounds from the 70% methanol extract of M. volcanica, by which six compounds with a wide range of polarities were separated in a single run of CCC and were identified as gallic acid, protocatechuic acid, 4,4′-dihydroxy-3,3′-imino-di-benzoic acid, rutin, quercitrin, and quercetin. Then, two compounds from the fractions of stepwise elution CCC were separated using conventional high-speed CCC, pH-zone-refining CCC, and preparative high-performance liquid chromatography, and identified as shikimic acid and miquelianin. These compounds are reported from M. volcanica for the first time. Notably, except for shikimic acid, all other compounds showed anti-diabetic potentials via antioxidant, antiglycation, and aldose reductase inhibition. The results suggest that the polarity-stepwise elution CCC can be used to efficiently separate or fractionate compounds with a wide range of polarities from natural products. Moreover, M. volcanica and its bioactive compounds are potent anti-diabetic agents.

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Section: Methodsmentioning

confidence: 99%

Efficient Separation of Phytochemicals from Muehlenbeckia volcanica (Benth.) Endl. by Polarity-Stepwise Elution Counter-Current Chromatography and Their Antioxidant, Antiglycation, and Aldose Reductase Inhibition Potentials

et al. 2021

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“…The solvent system was screened via HPLC and evaluated according to the partition coefficient ( K value) of the target compounds on the principle introduced by Ito [ 32 ]. Briefly, four solvent systems comprising EtOAc, n -BuOH, and H 2 O were first acidified by using formic acid to 208 mM or basified by using ammonia solution to 29 mM, and then the corresponding K values of the target compounds under acidic ( K acid ) or basic ( K base ) conditions were determined, as previously described [ 36 ]: each acidified or basified solvent system was partitioned to upper layer and lower layer. Thereafter, the extract (about 1–2 mg) was prepared in a 1.5 mL tube and dissolved by adding equal volumes (each 500 µL) of the upper layer and lower layers, which were mixed by a vortex mixer and centrifuged for about 20 s using a C1301 Mini Centrifuge (Labnet International, South Korea).…”

Section: Methodsmentioning

confidence: 99%

“…In particular, the antioxidants and enzyme inhibitors in extracts can be screened using 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical reaction-based DPPH-high-performance liquid chromatography (HPLC) [ 27 , 28 ] and enzyme–ligand binding affinity-based ultrafiltration-HPLC [ 29 , 30 , 31 ], respectively. Moreover, as a versatile separation chromatography based on a continuous liquid–liquid partition, high-speed counter-current chromatography (HSCCC) with advantages of support matrix-free, no irreversible adsorption, low risk of sample denaturation, and high sample loading capacity has immense potential in separating natural products [ 32 , 33 ], and it is suitable to couple offline DPPH- and ultrafiltration-HPLC in order to achieve efficient screening and separation of bioactive compounds from natural product extracts [ 34 , 35 , 36 ]. Furthermore, pH-zone-refining counter-current chromatography (CCC), developed from conventional HSCCC, can be particularly used for the preparative separation of ionizable target compounds [ 32 , 37 , 38 ].…”

Section: Introductionmentioning

confidence: 99%

Valeriana rigida Ruiz & Pav. Root Extract: A New Source of Caffeoylquinic Acids with Antioxidant and Aldose Reductase Inhibitory Activities

Zuo

Kim

Quispe

et al. 2021

Foods

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Valeriana rigida Ruiz & Pav. (V. rigida) has long been used as a herbal medicine in Peru; however, its phytochemicals and pharmacology need to be scientifically explored. In this study, we combined the offline 2,2-diphenyl-1-picryl-hydrazyl-hydrate (DPPH)-/ultrafiltration-high-performance liquid chromatography (HPLC) and high-speed counter-current chromatography (HSCCC)/pH-zone-refining counter-current chromatography (pH-zone-refining CCC) to screen and separate the antioxidants and aldose reductase (AR) inhibitors from the 70% MeOH extract of V. rigida, which exhibited remarkable antioxidant and AR inhibitory activities. Seven compounds were initially screened as target compounds exhibiting dual antioxidant and AR inhibitory activities using DPPH-/ultrafiltration-HPLC, which guided the subsequent pH-zone-refining CCC and HSCCC separations of these target compounds, namely 3-O-caffeoylquinic acid, 4-O-caffeoylquinic acid, 5-O-caffeoylquinic acid, 3,4-O-di-caffeoylquinic acid, 3,5-O-di-caffeoylquinic acid, 4,5-O-di-caffeoylquinic acid, and 3,4,5-O-tri-caffeoylquinic acid. These compounds are identified for the first time in V. rigida and exhibited remarkable antioxidant and AR inhibitory activities. The results demonstrate that the method established in this study can be used to efficiently screen and separate the antioxidants and AR inhibitors from natural products and, particularly, the root extract of V. rigida is a new source of caffeoylquinic acids with antioxidant and AR inhibitory activities, and it can be used as a potential functional food ingredient for diabetes.

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“…Countercurrent chromatography is a type of liquid–liquid partition chromatography that has been widely used for the separation of components of natural plants [29], preparation of reference standards, and discovery of new compounds [30]. The pH‐peak‐focusing countercurrent chromatography technique was developed from an accidental finding that a thyroxine analog produced an unusually sharp elution peak.…”

Section: Introductionmentioning

confidence: 99%

Retention mechanism of pH‐peak‐focusing in countercurrent chromatographic separation of baicalin and wogonoside from Scutellaria baicalensis Georgi

Wang

Zuo

Wang

et al. 2020

J of Separation Science

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An efficient and target-oriented pH-peak-focusing countercurrent chromatographic method was established for large-scale separation of baicalin and wogonoside from the crude exact of traditional Chinese medicinal herb Scutellaria baicalensis Georgi. An optimized two-phase solvent system composed of n-butanol-ethyl acetate-methanol-water (1:4:0.5:5, v/v) was selected. Trifluoroacetic acid (10 mmol/L) was added to the upper organic phase, used as the stationary phase. One liter of the aqueous lower phase was used as the mobile phase for 0-350 min, and then 10 mmol/L ammonia was added to remaining 1 L of the aqueous lower phase and used as the mobile phase for 350-600 min. In total, 493.2 mg of baicalin with 98.6% purity and 88.6 mg of wogonoside with 98.9% purity were obtained from 1.0 g of crude exact of S. baicalensis by countercurrent chromatography in a single run. The acid dissociation constant (pKa) and oil-water partition coefficient values of two components were measured to better understand the mechanism of separation. Results showed that pH-peakfocusing countercurrent chromatography with a polar solvent system added with trifluoroacetic acid could be an efficient method for large-scale isolation of organic acids, which are difficult to separate with conventional countercurrent chromatography due to their poor solubility in non-polar solvents.

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Target guided isolation of potential tyrosinase inhibitors from Otholobium pubescens (Poir.) J.W. Grimes by ultrafiltration, high-speed countercurrent chromatography and preparative HPLC

Cited by 24 publications

References 32 publications

Efficient Separation of Phytochemicals from Muehlenbeckia volcanica (Benth.) Endl. by Polarity-Stepwise Elution Counter-Current Chromatography and Their Antioxidant, Antiglycation, and Aldose Reductase Inhibition Potentials

Efficient Separation of Phytochemicals from Muehlenbeckia volcanica (Benth.) Endl. by Polarity-Stepwise Elution Counter-Current Chromatography and Their Antioxidant, Antiglycation, and Aldose Reductase Inhibition Potentials

Valeriana rigida Ruiz & Pav. Root Extract: A New Source of Caffeoylquinic Acids with Antioxidant and Aldose Reductase Inhibitory Activities

Retention mechanism of pH‐peak‐focusing in countercurrent chromatographic separation of baicalin and wogonoside from Scutellaria baicalensis Georgi

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