Centrifugal partition chromatography: an efficient tool to access highly polar and unstable synthetic compounds on a large scale

Marković, Dean; Barboux, Cédric; Chou, Y Salle de; Bettach, Judith; Grougnet, Raphaë͏l; Deguin, Brigitte

doi:10.1039/c4ra12141d

Cited by 3 publications

(3 citation statements)

References 50 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Nevertheless, no glycosylated sesquiterpenes (and sesquiterpene lactones) were previously found in this genus. CPC has been used in a semi-empirical mode [ 20 ] as a replacement of vacuum liquid chromatography (VLC) or reversed-phase medium pressure liquid chromatography (MPLC), permitting specially the isolation of several terpene glycosides [ 27 ], such as a geranyl disaccharide [ 28 ], natural [ 29 – 30 ], semisynthetic iridoid derivatives [ 31 ], and diterpene glycosides [ 32 ]. This technique was for the first time used with Jungia extracts.…”

Section: Resultsmentioning

confidence: 99%

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

Azevedo

Faqueti

Kritsanida

et al. 2016

Beilstein J. Org. Chem.

Self Cite

View full text Add to dashboard Cite

Summary 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.

show abstract

Section: Resultsmentioning

confidence: 99%

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

Azevedo

Faqueti

Kritsanida

et al. 2016

Beilstein J. Org. Chem.

Self Cite

View full text Add to dashboard Cite

show abstract

“…This latter appeared to be the most efficient and fast way to purify AH. Indeed, counter‐current chromatography (CCC) techniques, such as CPC, are efficient for the separation of polar extracts (Wang et al, ) and were already successfully applied to the isolation of iridoids (Kim and Kim, ; Marković et al, ; Tong et al, ). Moreover, scale‐up procedure with CPC is considered as quasi‐linear and therefore is suitable for large amount of extracts as pilot and industrial scale instruments are available.…”

Section: Resultsmentioning

confidence: 99%

HPLC‐ELSD Quantification and Centrifugal Partition Chromatography Isolation of 8‐O‐Acetylharpagide from Oxera coronata (Lamiaceae)

Remeur

Borgne

Gauthier

et al. 2016

Phytochemical Analysis

Self Cite

View full text Add to dashboard Cite

show abstract

“…In the study of Markovic et al (2014), 23.9 g of aucubin was purified from 105 g of leaf extract from Aucuba japonica Thunb. using ethyl acetate-npropanol-water (7:3:10) in three repetitive runs.…”

Section: Ccs and Iridoids' Isolationmentioning

confidence: 99%

An overview of the two-phase solvent systems used in the countercurrent separation of phenylethanoid glycosides and iridoids and their biological relevance

2019

View full text Add to dashboard Cite

Phenylethanoid glycosides (PhGs) and iridoids are two vast groups of water soluble secondary metabolites widely distributed in plant kingdom and well known for their important biological activities. Their purification by conventional chromatography is time consuming, uses large amounts of organic solvents and requires repeated steps. Moreover, the sample recovery is low, because the hydroxyl groups of PhGs and iridoids make them strongly adsorbed onto the solid support (silica gel, Sephadex LH-20) during separation. Being a liquid-liquid based technology, countercurrent separation (CCS) comes as an alternative tool to overcome the issues associated with solid-phase adsorbents. It has been successfully used for the separation of many groups of specialized plant metabolites. This is the first extensive review describing the application of CCS for purification of iridoids and PhGs, based on the research papers from the last 20 years (1998-2018) that used countercurrent chromatography and centrifugal partition chromatography technologies. In total, 65 papers described the isolation of 84 different phytochemicals (28 PhGs and 56 iridoids) from 42 plant species belonging to 16 distinct families that were separated with 59 different biphasic solvent systems. Since PhGs and iridoids are highly polar molecules, more than half of the employed systems (56%) were composed of various ratios of ethyl acetate-alcohol-water, as well as binary systems, such as ethyl acetate-water and n-butanolwater. The current review may be used as starting point for CCS users on their sinuous road of isolating known or waiting to be discovered PhGs and iridoids.

show abstract

Centrifugal partition chromatography: an efficient tool to access highly polar and unstable synthetic compounds on a large scale

Cited by 3 publications

References 50 publications

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

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

HPLC‐ELSD Quantification and Centrifugal Partition Chromatography Isolation of 8‐O‐Acetylharpagide from Oxera coronata (Lamiaceae)

An overview of the two-phase solvent systems used in the countercurrent separation of phenylethanoid glycosides and iridoids and their biological relevance

Contact Info

Product

Resources

About