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

Remeur, Camille; Borgne, Erell Le; Gauthier, L.; Grougnet, Raphaë͏l; Deguin, Brigitte; Poullain, Cyril; Litaudon, Marc

doi:10.1002/pca.2667

Cited by 5 publications

(3 citation statements)

References 24 publications

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“…Fractions were collected every 10 and 20 mL during elution and extrusion respectively, and pooled when their TLC profile were similar. These chromatographic conditions were adapted from previous investigations [27,28].…”

Section: Cpc Experimentsmentioning

confidence: 99%

Updated pigment composition of Tisochrysis lutea and purification of fucoxanthin using centrifugal partition chromatography coupled to flash chromatography for the chemosensitization of melanoma cells

et al. 2020

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Tisochrysis lutea (T. lutea, ex T. Isochrysis galbana or T-Iso) is a marine haptophyte that was first isolated from Tahiti seawater. Because of its high content in lipids, this tropical species is commonly used in aquaculture to feed fishes, crustaceans and molluscs larvae. It is also a rich source of fucoxanthin with a high potential for nutraceutical, cosmetic and pharmaceutical applications. The purpose of the present study was to detail the pigment composition of T. lutea and to develop an efficient process to recover highly purified fucoxanthin. Using ultra performant liquid chromatography coupled to diode arrays and high-resolution mass spectrometry detectors (UPLC-DAD-MS/MS), we demonstrated for the first time the presence of echinenone, 3-hydroxy-echinenone and chlorophyll c2-monogalactosyldiacylglycerol [18:4/14:0] in unstressed cultures of T. lutea. The chemotaxonomic relevance of this updated pigment composition was discussed in relation to the Haptophyta phylum. A two-step purification of fucoxanthin was then optimized using centrifugal partition chromatography coupled to flash chromatography. This process allowed the efficient isolation of fucoxanthin (purity > 99%), that was further assessed as a lowtoxicity antineoplastic and chemosensitizing natural product in human chemoresistant melanoma cells. This carotenoid exerted an antiproliferative activity in A2058 melanoma cells and reversed in vitro their chemoresistance to dacarbazine, a DNA-alkylating agent clinically used for the treatment of metastatic melanoma.Please note that this is an author-produced PDF of an article accepted for publication following peer review. The definitive publisher-authenticated version is available on the publisher Web site.

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Section: Cpc Experimentsmentioning

confidence: 99%

Updated pigment composition of Tisochrysis lutea and purification of fucoxanthin using centrifugal partition chromatography coupled to flash chromatography for the chemosensitization of melanoma cells

et al. 2020

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“…In Lemus et al (2015), two new (3-hydroxymyopchlorin and 5-hydroxyglutinoside) and five known C-9 iridoids (caprarioside, macfadyenoside, 8-O-acetylharpagide, catalpol and 6-b-hydroxyantirrhide) were separated from Capraria biflora L. The methanolic extract of aerial parts was submitted to CPC, first with tetrahydrofuran-ethyl acetate-water (4:9:12) and second with ethyl acetate-n- propanol-water (8:4:12). Adjusting the solvent ratios to ethyl acetate-npropanol-water (3:2:5) allowed the purification of 8-O-acetylharpagide from the aqueous leaf extract of Oxera coronata Kok in one run (Remeur et al 2017). Replacing n-propanol with its isomer, as in ethyl acetate-2-propanol-water (3:2:5), led to the isolation of C-10 iridoid geniposide from Gardenia jasminoides Ellis (Kim and Kim 2007).…”

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

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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.

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“…It is important to consider a drug's pharmacokinetic qualities as well as its potency and side effects when assessing its potential uses. TLC (thin-layer chromatography) [24], HPLC-UV [25], HPLC-ELSD (evaporative light scattering detection) [26], LC-MS/MS [27], and several high-performance liquid chromatography methods with UV detection have been used to analyze iridoid glycosides.…”

Section: Introductionmentioning

confidence: 99%

Simultaneous Determination of Five Iridoids of Picrorhiza scrophulariiflora in Rat Plasma Using UHPLC-ESI-MS/MS

Wang,

Shi,

Jiang

et al. 2023

Molecules

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In this study, we developed an ultra-performance liquid chromatography-electrospray tandem quadrupole mass spectrometry (UHPLC-ESI-MS/MS) method to simultaneously determine Picroside-I, Picroside-II, Picroside-III, minecoside, and sweroside in rat plasma. The chromatographic column was an ACQUITY UHPLC® BEH Amide Column (2.1 × 100 mm, 1.7 µm; Waters, MA, USA), column temperature 40 °C. The mobile phase was 0.1% formic acid aqueous solution–0.1% formic acid acetonitrile solution. The flow rate was 0.4 mL/min. Multiple reaction monitoring (MRM) and negative ion modes were adopted. The results showed that the calibration curves of five compounds in plasma showed good linearity (r > 0.9911) over the studied dose range. The lower limits of quantification (LLOQ) for Picroside-I, Picroside-II, Picroside-III, minecoside, and sweroside were 6.876, 5.193, 5.040, 1.260, and 4.527 ng/mL, respectively. The intra-day and inter-day precision were <15%. The matrix effects ranged from 95.77 to 101.9%. The Tmax were 1.1 ± 0.2, 1.1 ± 0.1, 0.8 ± 0.1, 1.0 ± 0.2, and 2.1 ± 0.1 h. This study will be useful in understanding the behavior of drugs in the body and the body’s effect on drugs. It also offers theoretical underpinnings and highlights the importance of clinical applications and creating novel drugs.

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

Abstract: HPLC-ELSD has proven to be a well-adapted detection and quantification method for iridoid glycosides, while CPC confirmed to be an efficient technique for the isolation of polar compounds. Copyright © 2016 John Wiley & Sons, Ltd.

Cited by 5 publications

References 24 publications

Updated pigment composition of Tisochrysis lutea and purification of fucoxanthin using centrifugal partition chromatography coupled to flash chromatography for the chemosensitization of melanoma cells

Updated pigment composition of Tisochrysis lutea and purification of fucoxanthin using centrifugal partition chromatography coupled to flash chromatography for the chemosensitization of melanoma cells

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

Simultaneous Determination of Five Iridoids of Picrorhiza scrophulariiflora in Rat Plasma Using UHPLC-ESI-MS/MS

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