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Cichorins D-F: Three New Compounds from Cichorium intybus and Their Biological Effects.

ABSTRACT: Cichorium intybus L., (chicory) is employed in various traditional medicines to treat a wide range of diseases and disorders. In the current investigation, two new naphthalane derivatives viz., cichorins D (1) and E (2), along with one new anthraquinone cichorin F (3), were isolated from Cichorium intybus. In addition, three previously reported compounds viz., ?-sitosterol (4), ?-sitosterol ?-glucopyranoside (5), and stigmasterol (6) were also isolated from Cichorium intybus. Their structures were established via extensive spectroscopic data, including 1D (1H and 13C) and 2D NMR (COSY, HSQC and HMBC), and ESIMS. Cichorin E (2) has a weak cytotoxic effect on breast cancer cells (MDA-MB-468: IC50: 85.9 µM) and Ewing's sarcoma cells (SK-N-MC: IC50: 71.1 µM); cichorin F (3) also illustrated weak cytotoxic effects on breast cancer cells (MDA-MB-468: IC50: 41.0 µM and MDA-MB-231: IC50: 45.6 µM), and SK-N-MC cells (IC50: 71.9 µM). Moreover compounds 1-3 did not show any promising anthelmintic effects.

SUBMITTER: Khan MF

PROVIDER: S-EPMC7570803 | biostudies-literature | 2020 Sep

REPOSITORIES: biostudies-literature

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Cichorins D-F: Three New Compounds from Cichorium intybus and Their Biological Effects.

Khan Muhammad Farooq MF Nasr Fahd A FA Noman Omar M OM Alyhya Nouf Abdulaziz NA Ali Iftikhar I Saoud Mohamad M Rennert Robert R Dube Mthandazo M Hussain Wahid W Green Ivan R IR Basudan Omer Ahmed M OAM Ullah Riaz R Anazi Shamsa Hilal SH Hussain Hidayat H

Molecules (Basel, Switzerland) 20200911 18

Cichorium intybus L., (chicory) is employed in various traditional medicines to treat a wide range of diseases and disorders. In the current investigation, two new naphthalane derivatives viz., cichorins D (1) and E (2), along with one new anthraquinone cichorin F (3), were isolated from Cichorium intybus. In addition, three previously reported compounds viz., β-sitosterol (4), β-sitosterol β-glucopyranoside (5), and stigmasterol (6) were a ...[more]

PMID: 32932909

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Project description:The present study aimed to determine the bioactive profile of various extracts of Cichorium intybus L. “hairy” roots. In particular, the total content of flavonoids as well as the reducing power, antioxidant and anti-inflammatory activity of the aqueous and ethanolic (70%) extracts were evaluated. The total content of flavonoids the ethanolic extract of the dry “hairy” root reached up to 121.3 mg (RE)/g, which was twofold greater than in the aqueous one. A total of 33 diverse polyphenols were identified by the LC-HRMS method. The experimental results showed a high amount of gallic (6.103 ± 0.008 mg/g) and caffeic (7.001 ± 0.068 mg/g) acids. In the “hairy” roots, the presence of rutin, apigenin, kaempferol, quercetin, and its derivatives was found in concentrations of 0.201±0.003 – 6.710±0.052 mg/g. The broad spectrum of pharmacological activities (antioxidant, anti-inflammatory, antimutagenic, anticarcinogenic, etc.) of the key flavonoids identified in the chicory “hairy” root extract was predicted by the General Unrestricted Structure-Activity Relationships algorithm based on in the substances detected in the extract. The evaluation of the antioxidant activity showed that the EC50 values of the ethanol and the aqueous extracts were 0.174 and 0.346 mg, respectively. Thus, the higher ability of the ethanol extract to scavenge the DPPH radical was observed. The calculated Michaelis and inhibition constants indicated that the ethanolic extract of C. intybus “hairy” roots is an efficient inhibitor of soybean 15-Lipoxygenase activity (IC50 = 84.13 ± 7.22 μM) in a mixed mechanism. Therefore, the obtained extracts could be the basis of herbal pharmaceuticals for the therapy of human diseases accompanied by oxidative stress and inflammation, including the pandemic coronavirus disease COVID-19. Graphical abstract Image 1 Highlights • Bioactive profile of Cichorium intybus L. ‘hairy’ roots extracts was determined.• Totally, ethanol extract contained flavonoids up to 121.3 mg (RE)/g.• 33 polyphenol compounds in the ethanol extract were identified.• Gallic and coffeic acids, routine, apigenin were quantified up to 7.0 mg/g.• High antioxidant and anti-inflammatory activities of the extract was predicted.

Dataset Information

Cichorins D-F: Three New Compounds from Cichorium intybus and Their Biological Effects.

Publications

Cichorins D-F: Three New Compounds from <i>Cichorium intybus</i> and Their Biological Effects.

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