Preparative isolation and purification of cuminaldehyde and p-menta-1,4-dien-7-al from the essential oil of Cuminum cyminum L. by high-speed counter-current chromatography

Chen, Qinqin; Hu, Xuefang; Li, Jingming; Liu, Ping; Yang, Yang; Ni, Yingdong

doi:10.1016/j.aca.2011.01.038

Cited by 39 publications

(31 citation statements)

References 27 publications

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“…HSCCC (TBE‐20A, Tauto Biotech, Shanghai, China) was used to further purify flavanones from citrus peel. The partition coefficients ( K values) of neoeriocitrin, naringin, hesperidin, and neohesperidin were determined by HPLC using a modified method (Chen et al, ; Zhang et al, ). Briefly, 5.0 mL of one phase of the equilibrated two‐phase solvent system was added into a glass tube (50.0 mL) and mixed with 20.0 mg of RCE for 5 min.…”

Section: Methodsmentioning

confidence: 99%

“…The amount of these flavanones in citrus peel is higher than that in other parts of the fruit (Zhang et al, ). However, the separation of neoeriocitrin, naringin, hesperidin, and neohesperidin is considerably challenging due to chemical similarities (Chen et al, ).…”

Section: Introductionmentioning

confidence: 99%

“…However, its application in the extraction of flavanones from C. changshanensis peel has not been reported. High‐speed counter‐current chromatography (HSCCC) has been widely used in the isolation and purification of active components from herbs and natural products because of its shorter time of isolation, wider range of selection of two‐phase solvent systems, and higher recovery rates compared to other liquid–liquid techniques (Chen et al, ; Li, Sun, & Liu, ). In an attempt to reduce environmental pollution and maximize the economic value, we isolated and purified flavanones from C. changshanensis peel.…”

Section: Introductionmentioning

confidence: 99%

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Isolation and purification of four flavanones from peel of Citrus changshanensis

Liu

Han

2017

J Food Process Preserv

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Four flavanone glycosides, i.e., neoeriocitrin, naringin, hesperidin, and neohesperidin, were extracted, separated, and purified from the peel of Citrus changshanensis using homogenate extraction; AB‐8 macroporous resin column chromatography, and high‐speed counter‐current chromatography (HSCCC). Homogenate extraction was effective in the extraction of flavanones (yield: 437 mg g−1), and HSCCC was successful in the separation of flavanones. Ethyl acetate‐butanol‐water (3:2:5, v/v/v) was selected to separate naringin from neohesperidin. Neoeriocitrin and hesperidin were purified with chloroform‐methanol‐n‐butanol‐water (4:3:1:3, v/v/v/v). The compounds purified by HSCCC were analyzed by high‐performance liquid chromatography and liquid chromatography‐mass spectrometry. The purity of neoeriocitrin, hesperidin, naringin, and neohesperidin extracted from C. changshanensis peel was 95.47, 99.62, 99.21, and 98.45%, respectively. Practical applications Homogenate extraction represents an adequate flavanone extraction method. The combination of homogenate extraction and HSCCC is effective for the isolation and purification of flavanone compounds from citrus peel. Our developed method will allow an in‐depth characterization of flavanones from C. changshanensis and the comprehensive utilization of citrus by‐products to reduce environmental pollution and maximize the economic value added.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Isolation and purification of four flavanones from peel of Citrus changshanensis

Liu

Han

2017

J Food Process Preserv

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“…CCC is a support-free liquid-liquid partition method which eliminates irreversible adsorption of samples onto the solid support, providing a wider range of selection of two-phase solvent systems and yielding high purity and recovery [11–15]. Being an amplification mode of analytic HPLC, preparative RP-HPLC has become a powerful tool due to its shorter isolation time, excellent efficiency and high recovery [16–19].…”

Section: Introductionmentioning

confidence: 99%

Comparative Studies on Performance of CCC and Preparative RP-HPLC in Separation and Purification of Steroid Saponins from Dioscorea Zingiberensis C.H.Wright

Zhang

Liang

Zhang

et al. 2015

J Steroids Hormon Sci

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Steroid saponins from Dioscorea zingiberensis C.H.Wright were separated for the first time using two chromatographic methods for comparison: counter-current chromatography (CCC) coupled with evaporative light scattering detector (ELSD) and preparative reversed phase high-performance liquid chromatography (RP-HPLC) with an ultraviolet detector. Ethyl acetate-n-butanol-methanol-water (4:1:2:4, v/v) was chosen as the two-phase solvent system for CCC, while the acetonitrile-water (25:75 for the first step and15:85 for the second step, v/v) was used as the mobile phase in the preparative RP-HPLC. The following five steroid saponins were purified by theses two chromatographic methods, in one-step operation by CCC and by two-step operation in preparative RP-HPLC: 1) 26-O-β-D- glucopyranosyl-(25R)-furost-5-en-3β, 22ζ, 26-triol-3-O-[β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (compound A), 2) 26-O-β-D-glucopyranosyl-(25R)-furost-5-en-3β, 22ζ, 4) 26-triol-3-O-[β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (compound B), 3) 26-O-β-D-glucopyranosyl-(25R)-furost-5-en-3β, 22ζ, 26-triol-3-O-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranoside (compound C), 4) 26-O-β-D-glucopyranosyl-(25R)-furost-5, 20(22)-diene-3β, 26-diol-3-O-{α-L-rhamnopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→2)]}-β-D-glucopyranoside (compound D) and 5) 26-O-β-D-glucopyranosyl-(25R)-furost-5, 20(22)-diene-3β, 26-diol-3-O-[β-D-glucopyranosyl-(1→4)-α-L-rhamnopyranosy-(1→2)]-β-D-glucopyranoside (compound E). The purities of these five steroid saponins separated by both methods were over 95%, and structural identification of these compounds was performed by ESI-MS, and 13C NMR. Comparison of these two established approaches revealed that CCC required a longer separation time but with less solvent consumption, whereas preparative RP-HPLC gave a shorter separation time but with higher solvent consumption. These results demonstrated that either of these two methods of different separation mechanism is feasible, economical and efficient for rapid preparative isolation and purification of steroid saponins from Dioscorea zingiberensis C.H.Wright.

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“…The essential oil obtained from cumin seeds is light brownish yellow, with a slightly bitter, spicy and aromatic flavor and a somewhat disagreeable odor [2] originating from cumin aldehyde, the main compound in the oil [3]. Cumin essential oil has a wide range of application, such as anti-nociceptive [4], antiinflammatory [5], antimicrobial [2; 6] and antioxidative [7].…”

Section: Introductionmentioning

confidence: 99%

The analysis of cumin seeds essential oil and total polyphenols from postdestillation waste material

Aćimović¹,

Tešević²,

Mara³

et al. 2016

Adv techn

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The essential oil content in cumin samples from Serbian market ranged between 2.0 and 4.0%, with 22 identified compounds, among which the most abundant were cumin aldehyde, β-pinene, γ-terpinene, γ-terpinene-7-al and p-cymene. Postdistillation cumin seeds waste material that remained after the essential oil extraction contains total polyphenols of between 30.1 and 47.5 mg GAE/g dry extract, as estimated by the Folin-Ciocalteu method. Hydroxybenzoic and hydroxycinnamic acids, as well as glycosides of flavonones and flavonoles, are the dominant polyphenols. However, according to DPPH method, the antioxidative potential of cumin postdistillation seeds waste was poor and it ranged between 0.02 and 0.04 mM TE/g. Further research will be focused on agro-food implementation of postdistillation waste material of cumin and other plants which are used for the essential oil production.

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Preparative isolation and purification of cuminaldehyde and p-menta-1,4-dien-7-al from the essential oil of Cuminum cyminum L. by high-speed counter-current chromatography

Cited by 39 publications

References 27 publications

Isolation and purification of four flavanones from peel of Citrus changshanensis

Isolation and purification of four flavanones from peel of Citrus changshanensis

Comparative Studies on Performance of CCC and Preparative RP-HPLC in Separation and Purification of Steroid Saponins from Dioscorea Zingiberensis C.H.Wright

The analysis of cumin seeds essential oil and total polyphenols from postdestillation waste material

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