Two new sesquiterpene lactone glycosides from <i>Cnicus benedictus</i>

Peng, Ying; Jian, Yuqing; Ali, Zulfiqar; Li, Bin; Zhang, Kaiqiang; Long, Fei; Peng, Chao; Cai, Xiong; Khan, Ikhlas A.; Wang, Wei

doi:10.1080/14786419.2017.1295239

Cited by 6 publications

(3 citation statements)

References 22 publications

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“…Apigenin 7- O -glucoside, astragalin, arctiin, nortracheloside, luteolin, sitogluside, and cnicin were isolated from the CBE according to the previous protocols [ 14 , 15 , 16 , 17 , 18 ]. All of the aforementioned compounds were purchased (Sigma Aldrich, Santacruz Biotech, USA and BioCrick, Sichuan Province, P. R. China) to ensure the antiviral’s maximum possible purity for the in vitro testing.…”

Section: Methodsmentioning

confidence: 99%

Cnicin as an Anti-SARS-CoV-2: An Integrated In Silico and In Vitro Approach for the Rapid Identification of Potential COVID-19 Therapeutics

et al. 2021

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Since the emergence of the SARS-CoV-2 pandemic in 2019, it has remained a significant global threat, especially with the newly evolved variants. Despite the presence of different COVID-19 vaccines, the discovery of proper antiviral therapeutics is an urgent necessity. Nature is considered as a historical trove for drug discovery, especially in global crises. During our efforts to discover potential anti-SARS CoV-2 natural therapeutics, screening our in-house natural products and plant crude extracts library led to the identification of C. benedictus extract as a promising candidate. To find out the main chemical constituents responsible for the extract’s antiviral activity, we utilized recently reported SARS CoV-2 structural information in comprehensive in silico investigations (e.g., ensemble docking and physics-based molecular modeling). As a result, we constructed protein–protein and protein–compound interaction networks that suggest cnicin as the most promising anti-SARS CoV-2 hit that might inhibit viral multi-targets. The subsequent in vitro validation confirmed that cnicin could impede the viral replication of SARS CoV-2 in a dose-dependent manner, with an IC50 value of 1.18 µg/mL. Furthermore, drug-like property calculations strongly recommended cnicin for further in vivo and clinical experiments. The present investigation highlighted natural products as crucial and readily available sources for developing antiviral therapeutics. Additionally, it revealed the key contributions of bioinformatics and computer-aided modeling tools in accelerating the discovery rate of potential therapeutics, particularly in emergency times like the current COVID-19 pandemic.

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Section: Methodsmentioning

confidence: 99%

Cnicin as an Anti-SARS-CoV-2: An Integrated In Silico and In Vitro Approach for the Rapid Identification of Potential COVID-19 Therapeutics

et al. 2021

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“…The phytochemistry of C. benedicta preparations has been relatively well reported. The plant is relatively rich in sesquiterpenoid glycosides, particularly cnicin (0.2-0.7%), polyacetylen and absinthin, 52 as well as lower relative amounts of salonitenolide and artemisiifolin. These compounds are believed to be largely responsible for the bitter flavour of C. benedicta extracts.…”

Section: Phytochemistrymentioning

confidence: 99%

“…59 A recent study has also identified two new sesquiterpene lactone glycosides, melitensin 15-O-β-D-glucoside (Figure 2d) and 11β,13dihydrosalonitenolide 15-O-β-D-glucoside (Figure 2e). 52 Interestingly, dried C. benedicta plant material, volatile oil produced from the leaves, and isolated cnicin all have potent antibacterial activity against multiple pathogenic species (Newall et al, 1996). 54 The sesquiterpene lactone structure of cnicin allows it to form covalent bonds with bacterial proteins, thereby disrupting the bacterial membrane structure and function.…”

Section: Sesquiterpene Lactonesmentioning

confidence: 99%

A Review of the Traditional Uses, Medicinal Properties and Phytochemistry of Centaurea benedicta L.

Tiwana¹,

Fua²,

Lu³

et al. 2021

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Centaurea benedicta L. is an annual herbaceous plant which belongs to the Asteraceae family. It is native to the Mediterranean region and western Asia and is commonly known as blessed thistle, holy thistle, St Benedict's thistle or spotted thistle. Traditionally, it has been used to treat bubonic plague and possesses diuretic, galactagogue, liver-strengthening and wound healing properties. Recent research studies have investigated its anticancer, antiinflammatory, antioxidant and other therapeutic properties. Several studies have also reported its antimicrobial activity against a range of bacterial pathogens. However, most of these studies were preliminary and only tested relatively high concentrations of the extracts. Additionally, most studies screened a limited number of pathogens. Cnicin is the main chemical compound present in C. benedicta and it has been widely investigated. However, few other compounds from this plant have been identified and/or investigated, and further phytochemical studies are warranted. Interestingly, pure cnicin has good anticancer activity, whilst the crude extracts lack cytotoxic properties. Phytochemical analyses of C. benedicta extracts reveal the presence of multiple flavonoids, tannins, terpenoids and lactones, although few specific phytochemicals within these phytochemical classes have been identified. A limited number of research studies have determined the toxicity profile of C. benedicta in order to evaluate its safety for human use. Substantially more detailed studies are required to rigorously investigate the therapeutic properties and phytochemistry of C. benedicta, which may ultimately lead to the development of new plant-based therapeutic medicines.

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HPLC/ESI‐MS Characterization of Phenolic Compounds from Cnicus benedictus L. Roots: A Study of Antioxidant, Antibacterial, Anti‐Inflammatory, and Anti‐Alzheimer's Activity

Rezig,

Benkaci‐Ali,

Fauconnier

et al. 2023

Chemistry & Biodiversity

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The phenolic composition of Cnicus benedictus roots from four Algerian regions was investigated. Extractions were performed in both hydro‐methanolic (30 : 70, v/v) and hydro‐ethanolic (30 : 70, v/v) solvents. Their efficiency was determined in terms of the qualitative and quantitative composition in phenolic compounds by HPLC‐LC/MS of the different extracts isolated from C. Benedictus roots. Cnicus benedictus roots extract have been characterized by high content of phenolic compounds, where the trans chalcone, 2,3‐dihydro flavone, 3‐hydroxy flavone and cinnamic acid constitute the major components, in addition to fourteen minor acidic compounds and flavonoids as rutin. The hydro‐methanolic extract was the richest in phenolic compounds yield from C benedictus. On the other hand, hydro methanolic (30 : 70, v/v) and hydro ethanolic (30 : 70, v/v) extracts exhibited a high anti‐inflammatory activity by in vitro 5‐lipoxygenase inhibitory activity (IC50: 6.05±94.16 μg/mL) as well as by in silico docking according two methods. Likewise, anti‐Alzheimer activity of extracts was confirmed by this last technique taking into account the major compounds identified. Antibacterial tests revealed interesting results compared to amoxicillin for the different regions studied with a high content in trans chalcone and 3‐hydroxy Flavone.

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Two new sesquiterpene lactone glycosides from Cnicus benedictus

Cited by 6 publications

References 22 publications

Cnicin as an Anti-SARS-CoV-2: An Integrated In Silico and In Vitro Approach for the Rapid Identification of Potential COVID-19 Therapeutics

Cnicin as an Anti-SARS-CoV-2: An Integrated In Silico and In Vitro Approach for the Rapid Identification of Potential COVID-19 Therapeutics

A Review of the Traditional Uses, Medicinal Properties and Phytochemistry of Centaurea benedicta L.

HPLC/ESI‐MS Characterization of Phenolic Compounds from Cnicus benedictus L. Roots: A Study of Antioxidant, Antibacterial, Anti‐Inflammatory, and Anti‐Alzheimer's Activity

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