Cyclocuneatol and Cuneatannin, New Cycloartane Triterpenoid and Ellagitannin Glycoside from <i>Euphorbia cuneata</i>

Elghamdi, Amjad A.; Abdallah, Hossam M.; Shehata, Ibrahim; Mohamed, Gamal A.; Shati, Ali A.; Alfaifi, Mohammad Y.; Elbehairi, Serag Eldin I.; Koshak, Abdulrahman E.; Ibrahim, Sabrin R. M.

doi:10.1002/slct.201901541

Cited by 4 publications

(5 citation statements)

References 38 publications

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“…Thymoquinone was purchased from Sigma-Aldrich Inc. (St. Louis, Broadway, MO, USA). Meanwhile, all other tested compounds were obtained from in-house library of chemical compounds, 2,3′,4,5′,6-pentahydroxybenzophenone, maclurin-6- O -β- d -glucopyranoside, aromadendrin-8- C -β- d -glucopyranoside [ 40 ], 1,3,6,7-tetrahydroxy-8-prenylxanthone [ 41 ], kaempferol-7- O -β- d -glucoside, naringenin [ 42 ], apigenin-7- O -β- d -glucoside [ 43 ], sagitol C [ 44 ], 1-hydroxy-3,4-dihydronorharmane, butyrolactone I [ 45 ], terrenolide S [ 46 ], and ingenine C [ 47 ]…”

Section: Methodsmentioning

confidence: 99%

Repurposing of Some Natural Product Isolates as SARS-COV-2 Main Protease Inhibitors via In Vitro Cell Free and Cell-Based Antiviral Assessments and Molecular Modeling Approaches

et al. 2021

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The emergence of the SARS-CoV-2 pandemic has prompted scientists to search for an efficient antiviral medicine to overcome the rapid spread and the marked increase in the number of patients worldwide. In this regard natural products could be a potential source of substances active against coronavirus infections. A systematic computer-aided virtual screening approach was carried out using commercially available natural products found on the Zinc Database in addition to an in-house compound library to identify potential natural product inhibitors of SARS-CoV-2 main protease (MPRO). The top eighteen hits from the screening were selected for in vitro evaluation on the viral protease (SARS-CoV-2 MPRO). Five compounds (naringenin, 2,3′,4,5′,6-pentahydroxybenzophenone, apigenin-7-O-glucoside, sennoside B, and acetoside) displayed high activity against the viral protein. Acteoside showed similar activity to the positive control GC376. The most potent compounds were tested in vitro on SARS-CoV-2 Egyptian strain where only naringenin showed moderate anti-SARS-CoV-2 activity at non-cytotoxic micromolar concentrations in vitro with a significant selectivity index (CC50/IC50 = 178.748/28.347 = 6.3). Moreover; a common feature pharmacophore model was generated to explain the requirements for enzyme inhibition by this diverse group of active ligands. These results pave a path for future repurposing and development of natural products to aid in the battle against COVID-19.

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Section: Methodsmentioning

confidence: 99%

Repurposing of Some Natural Product Isolates as SARS-COV-2 Main Protease Inhibitors via In Vitro Cell Free and Cell-Based Antiviral Assessments and Molecular Modeling Approaches

et al. 2021

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“…The total methanolic extract (TEC) was standardized for its major phenolic constitutes that were previously isolated [ 20 ]. The results showed the presence of 2 R -naringenin-7- O - β -glucoside ( 1 ), kaempferol-7- O - β -glucoside ( 2 ), cuneatannin ( 3 ), quercetin ( 4 ), and 2 R -naringenin ( 5 ) in concentrations of 6.16, 4.8, 51.05, 13.2, and 50 mg/g of extract, respectively ( Figure 1 ).…”

Section: Resultsmentioning

confidence: 99%

“…Milli-Q water (Merck Millipore Corporation, Billerica, MA, USA) was used for liquid chromatography analysis. 2 R -Naringenin, quercetin, cuneatannin, 2 R -naringenin-7- O - β -glucoside, and kaempferol-7- O - β -glucoside were isolated previously from E. cuneata [ 20 ]. Lipopolysaccharide (LPS; Escherichia coli serotype O111:B4) was bought from Sigma-Aldrich (St. Louis, MO, USA) and freshly prepared in normal saline on the challenge day.…”

Section: Methodsmentioning

confidence: 99%

“…It is also used to treat postpartum hemorrhage, and also reported to have analgesic and anti-inflammatory activities [ 15 , 18 , 19 ]. E. cuneata was recently characterized as containing several phytochemicals, including triterpenes and flavonoids [ 20 ]. The hemostatic activity of the plant juice is attributed to its flavonoid constituents [ 15 , 18 ].…”

Section: Introductionmentioning

confidence: 99%

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Euphorbia cuneata Represses LPS-Induced Acute Lung Injury in Mice via Its Antioxidative and Anti-Inflammatory Activities

Abdallah

El‐Agamy

Ibrahim

et al. 2020

Plants

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Euphorbia cuneata (EC; Euphorbiaceae), which widely grows in Saudi Arabia and Yemen, is used traditionally to treat pain and inflammation. This study aimed to evaluate the protective anti-inflammatory effect of a standardized extract of EC against lipopolysaccharide (LPS)-induced acute lung injury (ALI) in mice and the possible underlying mechanism(s) of this pharmacologic activity. ALI was induced in male Balb/c mice using intraperitoneal injection of LPS. A standardized total methanol extract of EC or dexamethasone was administered 5 days prior to LPS challenge. Bronchoalveolar fluid (BALF) and lung samples were collected for analysis. The results demonstrated the protective anti-inflammatory effect of EC against LPS-induced ALI in mice. Standardized EC contained 2R-naringenin-7-O-β-glucoside (1), kaempferol-7-O-β-glucoside (2), cuneatannin (3), quercetin (4), and 2R-naringenin (5) in concentrations of 6.16, 4.80, 51.05, 13.20, and 50.00 mg/g of extract, respectively. EC showed a protective effect against LPS-induced pulmonary damage. EC reduced lung wet/dry weight (W/D) ratio and total protein content in BALF, indicating attenuation of the pulmonary edema. Total and differential cell counts were decreased in EC-treated animals. Histopathological examination confirmed the protective effect of EC, as indicated by an amelioration of LPS-induced lesions in lung tissue. EC also showed a potent anti-oxidative property as it decreased lipid peroxidation and increased the antioxidants in lung tissue. Finally, the anti-inflammatory activity of EC was obvious through its ability to suppress the activation of nuclear factor-κB (NF-κB), and hence its reduction of the levels of downstream inflammatory mediators. In conclusion, these results demonstrate the protective effects of EC against LPS-induced lung injury in mice, which may be due to its antioxidative and anti-inflammatory activities.

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“…Plants of the genus Euphorbia are widely distributed across temperate, tropical and subtropical regions of South America, Asia and Africa. E. cuneata has been shown to contain a variety of phytochemicals, including triterpenes (cyclocuneatol) and flavonoids (cuneatannin) [ 18 ]; and it does not contain the toxic diterpenes found in other Euphorbiaceae members [ 19 ]. Obesity, food poisoning, and constipation are all treated with stem juice combined with water or milk.…”

Section: Introductionmentioning

confidence: 99%

Pharmacological Activities and Characterization of Phenolic and Flavonoid Compounds in Methanolic Extract of Euphorbia cuneata Vahl Aerial Parts

et al. 2021

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Euphorbia cuneata Vahl. (Euphorbiaceae) is a plant used in folk medicine for the treatment of pain and inflammation, although the biological basis for these effects has not been thoroughly investigated. The goal of this study was to investigate the pharmacological properties and characterization of phenolic and flavonoid compounds present in the aerial parts of E. cuneata. E. cuneata aerial parts were tested for antioxidant activity (DPPH), antibacterial activity, cell viability and cytotoxic effects, and anti-inflammatory activity. Phenolic and flavonoid contents (HPLC), and volatile constituents (GC-MS) were also characterized. The methanol extract had the highest antioxidant activity, while the ether extract had the lowest. The antioxidant activity of E. cuneata extract increased from (21.11%) at a concentration of 10 µg/mL to (95.53%) at a concentration of 1280 µg/mL. S. aureus was the most sensitive organism with the highest zone of inhibition and lowest MIC, with acetone extract; whereas C. tropicalis was the most resistant, with the lowest inhibition zone. MTT assay revealed that the methanol extract of E. cuneata had significant cytotoxic effects on the A549, Caco-2, and MDA-MB-231 cell lines, respectively. Lower concentrations of methanolic extract gave anti-inflammatory activity, and those effects were compared with indomethacin as a positive control. Pyrogallol was the most abundant phenolic acid, followed by caffeic, p-coumaric, ferulic, syringic, and gallic acids, respectively. The 7-hydroxyflavone and rutin flavonoids were also found in the extract. GC-mass analysis showed that aerial parts of E. cuneata were rich in methyl 12-hydroxy-9-octadecenoate. The volatile components were also composed of considerable amounts of hexadecanoic acid, methyl ester, (9E,12E)-octadeca-9,12-dienoyl chloride, and methyl octadeca-9,12-dienoate as well as a little amount of hexanal dimethyl acetal. It can be concluded that methanolic extract of E. cuneata could be used as an available source of natural bioactive constituents with consequent health benefits.

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Cyclocuneatol and Cuneatannin, New Cycloartane Triterpenoid and Ellagitannin Glycoside from Euphorbia cuneata

Cited by 4 publications

References 38 publications

Repurposing of Some Natural Product Isolates as SARS-COV-2 Main Protease Inhibitors via In Vitro Cell Free and Cell-Based Antiviral Assessments and Molecular Modeling Approaches

Repurposing of Some Natural Product Isolates as SARS-COV-2 Main Protease Inhibitors via In Vitro Cell Free and Cell-Based Antiviral Assessments and Molecular Modeling Approaches

Euphorbia cuneata Represses LPS-Induced Acute Lung Injury in Mice via Its Antioxidative and Anti-Inflammatory Activities

Pharmacological Activities and Characterization of Phenolic and Flavonoid Compounds in Methanolic Extract of Euphorbia cuneata Vahl Aerial Parts

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