A single-step isolation by centrifugal partition chromatography of the potential anti-inflammatory glaucolide B from Lepidaploa chamissonis

Silva, Layzon Antonio Lemos da; Sandjo, Louis P.; Fratoni, Eduarda; Moon, Yeo Jim Kinoshita; Dalmarco, Eduardo Monguilhott; Biavatti, Maique W.

doi:10.1016/j.chroma.2019.460362

Cited by 9 publications

(15 citation statements)

References 60 publications

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“…CPC is able to provide repetitive and selective separation conditions for the purification of single metabolites from plant extracts—also on preparative scale. High selectivity of applied methods, low solvent consumption, high sample loading capacity and lack of solid support that prevents sample loss is conducive to recover sufficient quantities of natural products even from complex plant extracts 25 , 26 . However, the scientific literature on the analysis of essential oils by counter current chromatography is limited.…”

Section: Introductionmentioning

confidence: 99%

The role of centrifugal partition chromatography in the removal of β-asarone from Acorus calamus essential oil

Szczeblewski

Wróblewski

Borzyszkowska-Bukowska

et al. 2022

Sci Rep

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AbstractΒ-asarone is a phenylpropane derivative present in the rhizomes of Acorus calamus, that was proved to exhibit toxic effects in humans. Because of its presence the whole plant that is commonly used in traditional medicine for its sedative, anti-inflammatory, neuroprotective and other properties has limited application nowadays. In the study, qualitative and quantitative analysis of a collection of nine essential oil (EO) samples of European and Asian origin was performed. The final content of β-asarone in the tested samples ranged between 0.265 and 1.885 mg/mL. Having in mind a possible application of the EO as a biopesticide, this research aimed at the development of CPC-based purification protocol that could help remove β-asarone from EO. It was proved that the biphasic solvent system composed of n-hexane/EtOAc/MeOH/water, 9:1:9:1 (v/v/v/v) was capable of the removal of the toxic constituent in the CPC chromatograph operated in the ascending elution mode with 2200 rpm and a flow rate of 5 mL/min. The chromatographic analysis that lasted only 144 min effectively separated β-asarone (purity of 95.5%) and α-asarone (purity of 93.7%) directly from the crude Acorus calamus rhizome EO.

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Section: Introductionmentioning

confidence: 99%

The role of centrifugal partition chromatography in the removal of β-asarone from Acorus calamus essential oil

Szczeblewski

Wróblewski

Borzyszkowska-Bukowska

et al. 2022

Sci Rep

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“…The extraction process based on leaf washing with acetone was previously used to selectively obtain glaucolide B ( 1 ) from Lepidaploa chamissonis (Less.) H. Rob [ 37 ]. The obtained crude extract was purified using single-step centrifugal partition chromatography employing the M HEMWat ( n -hexane/ethyl acetate/methanol/water, 5:6:5:6) biphasic solvent system [ 37 ].…”

Section: Resultsmentioning

confidence: 99%

Semisynthetic Sesquiterpene Lactones Generated by the Sensibility of Glaucolide B to Lewis and Brønsted–Lowry Acids and Bases: Cytotoxicity and Anti-Inflammatory Activities

et al. 2023

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Sesquiterpene lactone (SL) subtypes including hirsutinolide and cadinanolide have a controversial genesis. Metabolites of these classes are either described as natural products or as artifacts produced via the influence of solvents, chromatographic mobile phases, and adsorbents used in phytochemical studies. Based on this divergence, and to better understand the sensibility of these metabolites, different pH conditions were used to prepare semisynthetic SLs and evaluate the anti-inflammatory and antiproliferative activities. Therefore, glaucolide B (1) was treated with various Brønsted–Lowry and Lewis acids and bases—the same approach was applied to some of its derivatives—allowing us to obtain 14 semisynthetic SL derivatives, 10 of which are hereby reported for the first time. Hirsutinolide derivatives 7a (CC50 = 5.0 µM; SI = 2.5) and 7b (CC50 = 11.2 µM; SI = 2.5) and the germacranolide derivative 8a (CC50 = 3.1 µM; SI = 3.0) revealed significant cytotoxic activity and selectivity against human melanoma SK-MEL-28 cells when compared with that against non-tumoral HUVEC cells. Additionally, compounds 7a and 7c.1 showed strongly reduced interleukin-6 (IL-6) and nitrite (NOx) release in pre-treated M1 macrophages J774A.1 when stimulated with lipopolysaccharide. Despite the fact that hirsutinolide and cadinanolide SLs may be produced via plant metabolism, this study shows that acidic and alkaline extraction and solid-phase purification processes can promote their formation.

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“…Molecules 2021, 26, 5269 2 of 10 operation mode, and the choice of a wide range of solvent systems [3][4][5][6][7][8][9][10][11][12], so it can achieve the fractionations with sufficient amount to further in vitro bioactivity tests [11,12]. Lindera strychnifolia Fernandez-Villar (Lauraceae) is an evergreen shrub that is widely distributed in Asia.…”

Section: Isolation Of Active Compounds Using Dual-mode Cpc and Hplcmentioning

confidence: 99%

“…Centrifugal partition chromatography (CPC) is a type of support-free liquid-liquid chromatography technique that uses an immiscible two-phase solvent system to compose stationary and mobile phase. CPC offers many advantages such as a higher sample loading capacity, the absence of sample loss due to irreversible sample absorption to the solid column, a flexible operation mode, and the choice of a wide range of solvent systems [3][4][5][6][7][8][9][10][11][12], so it can achieve the fractionations with sufficient amount to further in vitro bioactivity tests [11,12]. Lindera strychnifolia Fernandez-Villar (Lauraceae) is an evergreen shrub that is widely distributed in Asia.…”

Section: Introductionmentioning

confidence: 99%

Bioassay-Guided Isolation of Two Eudesmane Sesquiterpenes from Lindera strychnifolia Using Centrifugal Partition Chromatography

et al. 2021

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In this study, a centrifugal partition chromatography (CPC) separation was applied to identify antioxidant-responsive element (ARE) induction molecules from the crude extract of Lindera strychnifolia roots. CPC was operated with a two-phase solvent system composed of n-hexane-methanol-water (10:8.5:1.5, v/v/v) in dual mode (descending to ascending), which provided a high recovery rate (>95.5%) with high resolution. Then, ARE induction activity of obtained CPC fractions was examined in ARE-transfected HepG2 cells according to the weight ratios of the obtained fractions. The fraction exhibiting ARE-inducing activity was further purified by preparative HPLC that led to isolation of two eudesmane type sesquiterpenes as active compounds. The chemical structures were elucidated as linderolide U (1) and a new sesquiterpene named as linderolide V (2) by spectroscopic data. Further bioactivity test demonstrated that compounds 1 and 2 enhanced ARE activity by 22.4-fold and 7.6-fold, respectively, at 100 μM concentration while 5 μM of sulforaphane induced ARE activity 24.8-fold compared to the control.

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A single-step isolation by centrifugal partition chromatography of the potential anti-inflammatory glaucolide B from Lepidaploa chamissonis

Cited by 9 publications

References 60 publications

The role of centrifugal partition chromatography in the removal of β-asarone from Acorus calamus essential oil

The role of centrifugal partition chromatography in the removal of β-asarone from Acorus calamus essential oil

Semisynthetic Sesquiterpene Lactones Generated by the Sensibility of Glaucolide B to Lewis and Brønsted–Lowry Acids and Bases: Cytotoxicity and Anti-Inflammatory Activities

Bioassay-Guided Isolation of Two Eudesmane Sesquiterpenes from Lindera strychnifolia Using Centrifugal Partition Chromatography

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