Chemical Constituents of Echinops spinosus from Tunisia

Bouattour, Emna; Fakhfakh, Jawhar; Affes, Marwa; Chawech, Rachid; Damak, Mohamed; Jarraya, Raoudha

doi:10.1007/s10600-017-2179-9

Cited by 8 publications

(10 citation statements)

References 12 publications

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“…The negative ion LC-MS metabolite profiles highlighted the presence of 45 peaks corresponding to 45 compounds, 10 of which are unidentified. Interestingly, only five of the identified compounds were previously reported from E. spinosus, namely, campesterol (22), stigmasterol (24), apigenin-7-β-O-(4"-O-trans-p-coumaroyl-glucoside (25), cholesterol (29), and brassicasterol (30) [15,[29][30][31]. Eleven compounds were previously reported in other Echinops species and were identified here for the first time in E. spinosus as quinic acid (2), neochlorogenic acid (3-O-caffeoylquinic acid) (6), chlorogenic acid (5-Ocaffeoylquinic acid) (7), 3,5-dicaffeoylquinic acid (cynarin) ( 9), apigenin-6-O-arabinoside-8-O-galactoside (13), 3,4-dicaffeoylquinic acid ( 14), apigenin-6-O-arabinoside-8-O-glucoside (15), 3,5-dicaffeoylquinic acid (16), 4,5-dicaffeoylquinic acid (17), luteolin-7-O-glucoside (18), and rutin (21) [32][33][34][35][36].…”

Section: Lc-esi-orbitrap-ms and (Hr) Lc-esi-orbitrap-ms/ms And Lc-dad...mentioning

confidence: 99%

“…Eleven compounds were previously reported in other Echinops species and were identified here for the first time in E. spinosus as quinic acid (2), neochlorogenic acid (3-O-caffeoylquinic acid) (6), chlorogenic acid (5-Ocaffeoylquinic acid) (7), 3,5-dicaffeoylquinic acid (cynarin) ( 9), apigenin-6-O-arabinoside-8-O-galactoside (13), 3,4-dicaffeoylquinic acid ( 14), apigenin-6-O-arabinoside-8-O-glucoside (15), 3,5-dicaffeoylquinic acid (16), 4,5-dicaffeoylquinic acid (17), luteolin-7-O-glucoside (18), and rutin (21) [32][33][34][35][36]. However, seven compounds were previously reported in plants of the Asteraceae family, but not from the Echinops species, and have been identified as protocatechuic acid hexoside (4), dicaffeoyl altraric acid (8), dicaffeoyl altraric acid isomer (12), tricaffeoylaltraricric acid (19), shimobashiraside C (23), trihydroxy-octadecadienoic (9,12,13trihydroxy-10,15-octadecadienoic acid, (9,12,13,TriHODE(10,15)) acid (28), and trihydroxyoctadecenoic acid (9,12,13-trihydroxy-10-octadecenoic acid, 9,12,13-TriHOME(10), pinellic acid) (33) [32,[37][38][39][40]. However, five compounds were identified for the first time in the genus Echinops and in the family Asteraceae.…”

Section: Lc-esi-orbitrap-ms and (Hr) Lc-esi-orbitrap-ms/ms And Lc-dad...mentioning

confidence: 99%

“…It is also used for stomach pain, indigestion, and lack of appetite; for diabetes as a diuretic or depurative; and to cure liver diseases [14]. These activities are strongly correlated with the abundance of secondary metabolites belonging to diverse classes such as alkaloids, sesquiterpenes, flavonoids, and polyphenolic compounds in different organs of E. spinosus [15].…”

Section: Introductionmentioning

confidence: 99%

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HR-LC-ESI-Orbitrap-MS-Based Metabolic Profiling Coupled with Chemometrics for the Discrimination of Different Echinops spinosus Organs and Evaluation of Their Antioxidant Activity

et al. 2022

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This study aimed to assess and correlate the phenolic content and the antioxidant activity of the methanol extracts of the stems, roots, flowers, and leaves of Echinops spinosus L. from north-eastern Algeria. Qualitative analysis was performed by high-resolution mass spectrometry (HR) LC-ESI-Orbitrap-MS and (HR) LC-ESI-Orbitrap-MS/MS). Forty-five compounds were identified in the methanol extracts; some are described for the first time in E. spinosus. Targeted phenolic compounds were quantified by HPLC-DAD and it was shown that caffeoyl quinic derivatives were the most abundant compounds. Chemometric analysis was performed using principal component analysis (PCA) and hierarchical cluster analysis (HCA) based on the qualitative and quantitative LC data. The score plot discriminates different Echinopsis spinosus organs into three distinct clusters, with the stems and flowers allocated in the same cluster, reflecting their resemblance in their secondary metabolites. The antioxidant activities of the methanol extracts were assessed using cupric reducing antioxidant capacity (CUPRAC), ferric reducing antioxidant assay (FRAP), diphenyl picryl hydrazyl radical-scavenging capacity assay (DPPH●), and 2,2’-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid (ABTS●+). The root extract exhibited the highest antioxidant activity, evidenced by 3.26 and 1.61 mmol Fe2+/g dried residue for CUPRAC and FRAP, respectively, and great free radical-scavenging activities estimated by 0.53 and 0.82 mmol TEAC/g dried residue for DPPH● and ABTS●+, respectively. The methanol extract of the roots demonstrated a significant level of total phenolics (TP: 125.16 mg GAE/g dried residue) and flavonoids (TFI: 25.40 QE/g dried residue TFII: 140 CE/g dried residue). Molecular docking revealed that tricaffeoyl-altraric acid and dicaffeoyl-altraric acid exhibited the best fit within the active sites of NADPH oxidase (NO) and myeloperoxidase (MP). From ADME/TOPAKT analyses, it can be concluded that tricaffeoyl-altraric acid and dicaffeoyl-altraric acid also revealed reasonable pharmacokinetic and pharmacodynamic characteristics with a significant safety profile.

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Section: Lc-esi-orbitrap-ms and (Hr) Lc-esi-orbitrap-ms/ms And Lc-dad...mentioning

confidence: 99%

Section: Lc-esi-orbitrap-ms and (Hr) Lc-esi-orbitrap-ms/ms And Lc-dad...mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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HR-LC-ESI-Orbitrap-MS-Based Metabolic Profiling Coupled with Chemometrics for the Discrimination of Different Echinops spinosus Organs and Evaluation of Their Antioxidant Activity

et al. 2022

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“…Twenty-three flavonoids were isolated [12,23]. One year later, Bouattour et al, isolated a new derivative of apigenin named apigenin-7-O-ß-D-glucoside-(4"-O-trans-p-coumaroyl) [27].…”

Section: Phytochemistrymentioning

confidence: 99%

Ethnopharmacognosy of Echinops spinosus L. in North Africa: A Mini Review

Bouzabata¹,

Mahomoodally²,

Tuberoso³

2018

J Complement Med Res

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Background: The genus Echinops (Asteraceae family, Echinopeae class) consists of ca. 120 species and is native to Africa, the Middle East, Europe, and Asia. In Algeria, this genus is represented by the very common species Echinops spinosus L. also known as "tesskra," which is used as a diuretic, hypoglycemic, for stomachic effects, liver disorders, and post-partum care. Objective: The aim of this presentation is to provide an overview of the ethnopharmacognosy studies conducted on E. spinosus in North Africa. Data on ethnomedicinal uses, chemical constituents, and pharmacological activity were systematically compiled. Methods: Several popular search databases, including PubMed, ScienceDirect, Scopus, Web of Science, and Stanford libraries were scrutinised to extract relevant information. The research focused only on English-written papers published between 1980 and 2017. Results: Echinops spinosus L. is traditionally used in North Africa, and it was found that the most ethnomedicinal use reports were from Morocco and Algeria. Promising results have been reported regarding its phytochemistry and pharmacological activity. Fortythree compounds were isolated from different parts of this species. No studies have been conducted to highlight the toxicity and clinical safety of this species. Conclusion: This review highlights the therapeutic potential of E. spinosus used in traditional medicine. Furthermore, clinical trials on standardized preparations are necessary to explore the full safety and efficacy of E. spinosus in North Africa.

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“…The aerial parts contain 23 different flavonoids, which are known for their antioxidant activity [ 17 , 21 , 22 ]. A new apigenin derivative, named apigenin-7- O -ß-D-glucoside-(4″- O - trans - p -coumaroyl), was identified [ 23 ]. Another two new sesquiterpenoids were identified and named echinopine A and echinopine B [ 19 ].…”

Section: Introductionmentioning

confidence: 99%

In Vivo Efficacy of Echinops spinosus Decoction as a Therapeutic for Cows at Risk of Clinical Endometritis

Boudelal

Adnane

Niar

et al. 2022

Animals

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Clinical endometritis (CE) is a multifactorial disease of dairy animals. Retained fetal membranes (RFM) and metritis are the major risk factors of CE in dairy cows. Because uterine inflammation affects the profitability of the dairy industry, antibiotics and hormonal therapies are commonly used to mitigate against the disease. However, the One-Health concept aims to reduce antibiotic use in food animals to avoid the emergence of drug resistance or residues in milk or meat. Thus, phytotherapy may represent a good alternative to antibiotics in food animals. Echinops spinosus (E. spinosus) is a natural plant known to have therapeutic, anti-inflammatory, antimicrobial, and wound-healing properties in vitro. The aim of the present study was to investigate the efficacy of E. spinosus as a preventive strategy for CE in dairy cows with other postpartum complications. Holstein–Friesian cows (n = 36) diagnosed with RFM or metritis enrolled in the study were allocated into three groups. One group received antibiotic treatment. Another group received prostaglandin injection (PG). The experimental group received E. spinosus decoction orally. As a control group, eutocic cows (n = 36), without RFM and metritis were included in the study. The efficiency of the treatment was based on the occurrence of CE and improved reproductive outcomes. At 30 ± 2 DPP, CE was diagnosed in 25%, 58.34%, and 75% in antibiotic, PG, and E. spinosus groups, respectively (p < 0.05). There were no differences between the groups at 55 ± 5 DPP (16.67%, 33.44%, and 41.67% in antibiotic, PG and E. spinosus groups, respectively, p > 0.05). The E. spinosus group had the longest open days, lowest conception rate at 150 DPP, and highest number of services per conception. Oral E. spinosus extract is ineffective as a therapeutic for cows at risk of CE. These findings may pave the way for future innovative strategies employing E. spinosus to protect cattle against endometritis.

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Chemical Constituents of Echinops spinosus from Tunisia

Cited by 8 publications

References 12 publications

HR-LC-ESI-Orbitrap-MS-Based Metabolic Profiling Coupled with Chemometrics for the Discrimination of Different Echinops spinosus Organs and Evaluation of Their Antioxidant Activity

HR-LC-ESI-Orbitrap-MS-Based Metabolic Profiling Coupled with Chemometrics for the Discrimination of Different Echinops spinosus Organs and Evaluation of Their Antioxidant Activity

Ethnopharmacognosy of Echinops spinosus L. in North Africa: A Mini Review

In Vivo Efficacy of Echinops spinosus Decoction as a Therapeutic for Cows at Risk of Clinical Endometritis

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