Three new trixane glycosides obtained from the leaves of Jungia sellowii Less. using centrifugal partition chromatography

Jungia sellowii (Asteraceae) is a shrub that grows in Southern Brazil and polar extract of its leaves presents anti-inflammatory properties. Cyperane, guaiane, nortrixane, and trixane sesquiterpene types were reported as the main metabolites in Jungia species. This work aims to describe the isolation and identification of sesquiterpenes in the leaves of J. sellowii using liquid–liquid partition and centrifugal partition chromatography. Thus, the crude extract of fresh leaves of J. sellowii was partitioned with hexane, dichloromethane, ethyl acetate and butanol, respectively. The butanol fraction was then subjected to a selected ternary system optimized for the CPC (centrifugal partition chromatography): ethyl acetate–ethanol–water (9:2:10, v/v/v). The separation was carried out isocratically at a flow rate of 25 mL/min at 1200 rpm, affording seven fractions A to G. TLC of fractions B, C and F displayed a single spot corresponding to three new glycosylated sesquiterpenoids. Their structures were established by using spectroscopic data in comparison to those reported in the literature. Furthermore, the isolates were evaluated for their leishmanicidal and cytotoxic effects. No cytotoxic effect was observed against the three cancer cell lines (HL60, JURKAT and REH), but compound 1 showed a weak antiprotozoal activity. Liquid–liquid partition and CPC turned to be a versatile technique of glycoside purification which is environmentally friendly and requires a limited amount of organic solvents.

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Isolation and identification of antiplasmodial N-alkylamides from Spilanthes acmella flowers using centrifugal partition chromatography and ESI-IT-TOF-MS

Journal of Chromatography B ◽

10.1016/j.jchromb.2011.05.013 ◽

2011 ◽

Vol 879 (21) ◽

pp. 1886-1892 ◽

Cited By ~ 26

Author(s):

Flaubert Mbeunkui ◽

Mary H. Grace ◽

Carmen Lategan ◽

Peter J. Smith ◽

Ilya Raskin ◽

...

Keyword(s):

Partition Chromatography ◽

Centrifugal Partition Chromatography ◽

Isolation And Identification ◽

Spilanthes Acmella ◽

Tof Ms

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ISOLATION AND IDENTIFICATION OF ANANIXANTHONE FROM ETHYL ACETATE EXTRACT OF ROOT BARK OF SLATRI (Calophyllum soulattri) (CLUSIACEAE))

ALCHEMY Jurnal Penelitian Kimia ◽

10.20961/alchemy.10.2.56.130-136 ◽

2016 ◽

Vol 10 (2) ◽

pp. 130

Author(s):

Dindha Ramah Mulia ◽

Nestri Wulandari ◽

Muhammad Widyo Wartono

Keyword(s):

Ethyl Acetate ◽

Spectroscopic Data ◽

Ethyl Acetate Extract ◽

Root Bark ◽

Isolation And Identification

<p><em></em>A xanthone, named ananixanthone (1) has been isolated and identified from the ethyl acetate extract of the root barks of Calophyllum soulattri. Structure of the compound was determined based on spectroscopic data, including UV, IR, NMR 1D, NMR 2D and by comparison with references.</p>

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Application of Linear Gradient Solvent System in Centrifugal Partition Chromatography Facilitating Bioassay-Guided Fractionation of Yongdamsagan-Tang, Traditional Oriental Decoction

Evidence-based Complementary and Alternative Medicine ◽

10.1155/2021/7552169 ◽

2021 ◽

Vol 2021 ◽

pp. 1-11

Author(s):

Ji Hoon Kim ◽

Eun Ju Jung ◽

Yun Jung Lee ◽

Chul Young Kim ◽

Je-Seung Jeon

Keyword(s):

Natural Products ◽

Crude Extract ◽

Solvent System ◽

Bioactive Molecules ◽

Partition Chromatography ◽

Centrifugal Partition Chromatography ◽

Isolation And Identification ◽

Time Saving ◽

K Value ◽

Linear Gradient

As important pharmaceutical resources, traditional herbal medicines retain continuous attention. To do that, isolation and identification of bioactive molecules from traditional herbal decoction are important. However, conventional fractionation through octadecyl silica column faces irreversible sample adsorption that causes a bias in bioactivity assessment. However, liquid-liquid chromatographic system suffers tedious K value calculation as well as insufficient capacity in separation power when crude extract composed of widely ranging polarities. Here, we developed a comprehensive linear gradient solvent system for centrifugal partition chromatography (CPC) to aid bioassay-guided isolation. The lower aqueous phase of the n-hexane-acetonitrile-water (10:2:8, v/v) was used as the stationary, whereas its upper organic phase followed by the upper phase of ethyl acetate-acetonitrile-water and water-saturated n-butanol-acetonitrile-water in the same ratio were eluted in a linear gradient mode, thereby increasing polarity in the mobile phase. The HPLC profiling of CPC fraction showed that proposed gradient CPC was suitable to separate metabolites from Yongdamsagan-Tang, a traditional medicinal decoction made of ten herbal plants. Exhibiting a high recovery yield of 98.3%, antioxidant response element (ARE) luciferase-inducing assay in HepG2 cells indicated that the fractions composed of baicalein and wogonin, the marker natural products of Scutellaria baicalensis, were to be the most effective molecules from Yongdamsagan-Tang. The presented results demonstrated that bioassay-guided separation that assisted with a linear gradient CPC is an incomparable alternative to HPLC and biphasic CPC in terms of higher yield rate and redundant K value calculation, respectively, which led to an unbiased/time-saving separation and identification of bioactive molecules from the complex crude extract of natural products.

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Bioassay-Guided Separation of Centipeda minima Using Comprehensive Linear Gradient Centrifugal Partition Chromatography

Molecules ◽

10.3390/molecules25133077 ◽

2020 ◽

Vol 25 (13) ◽

pp. 3077

Author(s):

Ji Hoon Kim ◽

Eun Ju Jung ◽

Yun Jung Lee ◽

En Mei Gao ◽

Ahmed Shah Syed ◽

...

Keyword(s):

Ethyl Acetate ◽

Gradient Elution ◽

Solvent System ◽

Luciferase Assay ◽

Partition Chromatography ◽

Centrifugal Partition Chromatography ◽

Lower Phase ◽

Linear Gradient ◽

Centipeda Minima ◽

Water Saturated

A comprehensive linear gradient solvent system for centrifugal partition chromatography (CPC) was developed for the bioassay-guided isolation of natural compounds. The gradient solvent system consisted of three different ternary biphasic solvents types: n-hexane–acetonitrile–water (10:2:8, v/v), ethyl acetate–acetonitrile–water (10:2:8, v/v), and water-saturated n-butanol–acetonitrile–water (10:2:8, v/v). The lower phase of the n-hexane–acetonitrile–water (10:2:8, v/v) was used as the stationary phase, while its upper phase, as well as ethyl acetate–acetonitrile–water (10:2:8), and water-saturated n-butanol–acetonitrile–water (10:2:8, v/v) were pumped to generate a linear gradient elution, increasing the mobile phase polarity. We used the gradient CPC to identify antioxidant response elements (AREs), inducing compounds from Centipeda minima, using an ARE-luciferase assay in HepG2 cells, which led to the purification of the active molecules 3-methoxyquercetin and brevilin A. The developed CPC solvent systems allow the separation and isolation of compounds with a wide polarity range, allowing active molecule identification in the complex crude extract of natural products.

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Cytotoxic Test of Extract and Fraction of Dendrophtoe Pentandra (L) Miq on T47D Cell

Jurnal Kimia Sains dan Aplikasi ◽

10.14710/jksa.22.3.73-78 ◽

2019 ◽

Vol 22 (3) ◽

pp. 73-78

Author(s):

Masayu Farah Diba ◽

Salni Salni ◽

Subandrate Subandrate

Keyword(s):

Ethyl Acetate ◽

Cytotoxic Effect ◽

Linear Equations ◽

Ethanol Extract ◽

Ethyl Acetate Fraction ◽

T47d Cell ◽

Assay Method ◽

Cytotoxic Effects ◽

Ic50 Value ◽

Ethanol Fraction

Indonesia has a variety of plants that have the potential for medicine. One of the plants used by the community as a drug with anticancer effects is Dendrophtoe petandra (L.) Miq. This study aims to determine the cytotoxic effect of ethanol extract, ethyl acetate fraction and water ethanol fraction of Dendrophtoe petandra (L.) Miq on T47D breast cancer cells. The cytotoxic effects of ethanol extract, ethyl acetate fraction and water ethanol fraction were carried out by MTT assay method using series concentration. Cytotoxic effects were assessed by calculating IC50 values using linear equations. Phytochemical test showed that Dendrophtoe petandra (L.) Miq contained saponins, terpenoids, flavonoids and tannins. The IC50 value of the ethanol extract, ethyl acetate fraction and water ethanol fraction were 417.506 μg/mL, 233.617 μg/mL, and 2748.357 μg/mL, respectively. The smaller the IC50 value means that the compound is more active. Water ethanol fraction of Dendrophtoe petandra (L.) Miq does not have a cytotoxic effect, whereas ethanol extract and ethyl acetate fraction of Dendrophtoe petandra (L.) Miq have cytotoxic effects in the medium strength category. The content of flavonoids and saponins in ethanol extract and ethyl acetate fraction of Dendrophtoe petandra (L.) Miq is thought to play role in causing T47D cell death. Cytotoxic effects of ethyl acetate fraction are stronger than ethanol extracts.

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Anti-bacterial Activity of Prenylated Xanthone from The Bark of Garcinia lowa

Jurnal Kimia VALENSI ◽

10.15408/jkv.v2i2.4057 ◽

2016 ◽

Vol 2 (2) ◽

pp. 81-84

Author(s):

Darwati Darwati ◽

Elisabeth Krismayanti ◽

Supriyatna Supriyatna ◽

Unang Supratman

Keyword(s):

Ethyl Acetate ◽

Spectroscopic Data ◽

Ethyl Acetate Extract ◽

Bacterial Activity ◽

Isolation And Identification ◽

Prenylated Xanthone ◽

Mic Value

Bioactivity-guided fractionation of a ethyl acetate extract of Garcinia lowa bark has led to the isolation and identification of a known prenylated xanthone, mangosharin, (2,6-dihydroxy-8-methoxy-5-(3-methylbut-2-enyl)-xanthone (1, 15.4 mg) The structure of the compound was identified from analysis of their spectroscopic data and by comparison with previous studies.Compound 1 showed anti-bacterial activity against Sreptococcus mutans with MIC value of 7.25 mg/mL. DOI : http://dx.doi.org/10.15408/jkv.v0i0.4057

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Preparative Separation of Three Monoterpenes from Perilla frutescens var. crispa Using Centrifugal Partition Chromatography

International Journal of Analytical Chemistry ◽

10.1155/2019/8751345 ◽

2019 ◽

Vol 2019 ◽

pp. 1-7

Author(s):

Bomi Nam ◽

Sunil Babu Paudel ◽

Jin-Baek Kim ◽

Chang Hyun Jin ◽

Dongho Lee ◽

...

Keyword(s):

Ethyl Acetate ◽

Mobile Phase ◽

Solvent System ◽

Perilla Frutescens ◽

Partition Chromatography ◽

Centrifugal Partition Chromatography ◽

Drying Process ◽

Two Phase ◽

C Nmr

Three monoterpenes, namely, 9-hydroxy isoegomaketone (1), isoegomaketone (2), and perilla ketone (3), were successfully separated from the supercritical carbon dioxide (SC-CO2) extract of the leaves of Perilla frutescens var. crispa (cv. Antisperill; Lamiaceae) by centrifugal partition chromatography (CPC). To obtain large quantities of these materials required for studies on their mechanism of action and in vivo effectiveness in inflammation, we used CPC because of its high loading capacity and reproducibility to purify the three compounds. Compound 1 (2.60 mg, 96.7% purity at 254 nm) was purified from 500 mg of the SC-CO2 extract of P. frutescens var. crispa (cv. Antisperill), using a two-phase solvent system comprising n-hexane/ethyl acetate/ethanol/water (5:5:5:5 v/v) in a descending mode. As compounds 2 (56.1 mg, 97.6% purity at 254 nm) and 3 (78.6 mg, 96.1% purity at 254 nm) are highly volatile and difficult to recover from an aqueous mobile phase after purification during the drying process, they were obtained from the same amount of the processed extract in an ascending mode using the upper organic phase as the mobile phase (n-hexane/ethyl acetate/ethanol/water, 8:2:8:2 v/v). The structures of compounds 1–3 were confirmed by 1H- and 13C-NMR analysis. Thus, based on our findings, we recommend centrifugal partition chromatography as a powerful technique for purifying the active principal compounds 1 and 2 from the leaves of P. frutescens var. crispa.

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Preparative Purification of Delphinidin 3-0-sambubioside from Roselle (Hibiscus sabdariffa L.) Petals by fast Centrifugation Partition Chromatography

JOURNAL OF ADVANCES IN CHEMISTRY ◽

10.24297/jac.v6i2.2628 ◽

2010 ◽

Vol 6 (2) ◽

pp. 999-1004

Author(s):

Hilaire Tanoh Kouakou ◽

Laurent Kouakou Kouakou ◽

Alain Decendit ◽

Alain Badoc ◽

Gregory Da-Costa ◽

...

Keyword(s):

Ethyl Acetate ◽

Amyloid Fibrils ◽

Hibiscus Sabdariffa ◽

Partition Chromatography ◽

Centrifugal Partition Chromatography ◽

Preparative Scale ◽

Mobile Phases ◽

Chromatographic Procedure ◽

Solvent Systems ◽

Liquid Chromatographic

Delphinidin 3-0-sambubioside, a Hibiscus anthocyanin, was isolated from MeOH/TFA dried flower of H. sabdariffa. Its purification on preparative scale was obtained by centrifugal partition chromatography (CPC) using the ternary biphasic solvent systems composed of ethyl acetate/1-butanol/water, acidified by 0.1% of TFA. Stationary phase was ethyl acetate/1-butanol/water (5:5:90; v/v). We tested 4 mobile phases and found that the system acetate/1-butanol/water (40:46:14; v/v) was the best to separate anthocyanin mentioned above. This support-free liquid-liquid chromatographic procedure made it possible to isolate delphinidin 3-0-sambubioside from flower of H. sabdariffa. The antiamyloidogenic activity of the isolated stilbenes was evaluated versus b-amyloid fibrils. delphinidin 3-0-sambubioside was found to be active with 67% inhibition at 10 mM.

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