Isolation, spectroscopic characterization, X-ray, theoretical studies as well as in vitro cytotoxicity of Samarcandin

Ghoran, Salar Hafez; Atabaki, Vahideh; Babaei, Esmaeil; Olfatkhah, Seyed Reza; Dušek, Michal; Eigner, Václav; Soltani, Alireza; Khalaji, Aliakbar Dehno

doi:10.1016/j.bioorg.2016.03.005

Cited by 15 publications

(7 citation statements)

References 30 publications

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“…Samarcandin, a natural sesquiterpene coumarin, is another molecule with high antiviral activity against RBD (−7.4 kcal/mol). Spectroscopic data show that samarcandin has strong similarity to badrakemin [ 40 ]. In the present study, badrakemin acetate was also a good inhibitor against RBD (−8.0 kcal/mol).…”

Section: Discussionmentioning

confidence: 99%

In Silico Evaluation of Iranian Medicinal Plant Phytoconstituents as Inhibitors against Main Protease and the Receptor-Binding Domain of SARS-CoV-2

et al. 2021

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The novel coronavirus disease 2019 (COVID-19) is caused by the severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), which initially appeared in Wuhan, China, in December 2019. Elderly individuals and those with comorbid conditions may be more vulnerable to this disease. Consequently, several research laboratories continue to focus on developing drugs to treat this infection because this disease has developed into a global pandemic with an extremely limited number of specific treatments available. Natural herbal remedies have long been used to treat illnesses in a variety of cultures. Modern medicine has achieved success due to the effectiveness of traditional medicines, which are derived from medicinal plants. The objective of this study was to determine whether components of natural origin from Iranian medicinal plants have an antiviral effect that can prevent humans from this coronavirus infection using the most reliable molecular docking method; in our case, we focused on the main protease (Mpro) and a receptor-binding domain (RBD). The results of molecular docking showed that among 169 molecules of natural origin from common Iranian medicinal plants, 20 molecules (chelidimerine, rutin, fumariline, catechin gallate, adlumidine, astragalin, somniferine, etc.) can be proposed as inhibitors against this coronavirus based on the binding free energy and type of interactions between these molecules and the studied proteins. Moreover, a molecular dynamics simulation study revealed that the chelidimerine–Mpro and somniferine–RBD complexes were stable for up to 50 ns below 0.5 nm. Our results provide valuable insights into this mechanism, which sheds light on future structure-based designs of high-potency inhibitors for SARS-CoV-2.

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Section: Discussionmentioning

confidence: 99%

In Silico Evaluation of Iranian Medicinal Plant Phytoconstituents as Inhibitors against Main Protease and the Receptor-Binding Domain of SARS-CoV-2

et al. 2021

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“…Samarcandin (23) Potential aphrodisiac [63], antifungal [54], cytotoxic against AGS (human gastric carcinoma), WEHI-164 (fibrosarcoma) cancer cell lines [106], active in NCI yeast anticancer drug screen assays [107], potential antiviral activity against Ebola virus [108,109].…”

Section: Secondary Metabolite Biological Activitiesmentioning

confidence: 99%

Next Chapter in the Legend of Silphion: Preliminary Morphological, Chemical, Biological and Pharmacological Evaluations, Initial Conservation Studies, and Reassessment of the Regional Extinction Event

Miski

2021

Plants

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Silphion was an ancient medicinal gum-resin; most likely obtained from a Ferula species growing in the Cyrene region of Libya ca. 2500 years ago. Due to its therapeutic properties and culinary value, silphion became the main economic commodity of the Cyrene region. It is generally believed that the source of silphion became extinct in the first century AD. However, there are a few references in the literature about the cultivated silphion plant and its existence up to the fifth century. Recently, a rare and endemic Ferula species that produces a pleasant-smelling gum-resin was found in three locations near formerly Greek villages in Anatolia. Morphologic features of this species closely resemble silphion, as it appears in the numismatic figures of antique Cyrenaic coins, and conform to descriptions by ancient authors. Initial chemical and pharmacological investigations of this species have confirmed the medicinal and spice-like quality of its gum-resin supporting a connection with the long-lost silphion. A preliminary conservation study has been initiated at the growth site of this rare endemic Ferula species. The results of this study and their implications on the regional extinction event, and future development of this species will be discussed.

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Section: Resultsmentioning

confidence: 99%

“…In a more recent publication, the stereochemistry of samarcandin ( 14 ) was reinvestigated by computational chemistry methods and X-ray crystallographic analysis. Despite the lack of required specific measurements and calculations for the establishment of absolute stereochemistry of samarcandin ( 14 ), the enantiomer of samarcandin (i.e., ent -samarcandin, 23 ) was proposed as the absolute atomic structure of samarcandin [ 37 ]. Close examination of the reviews of sesquiterpene coumarins in the literature also revealed the presence of similar confusion about the absolute stereochemistries of other sesquiterpene coumarins [ 62 , 63 , 64 , 65 ].…”

Section: Resultsmentioning

confidence: 99%

“…high-performance liquid chromatography (HPLC)). The following 15 sesquiterpene coumarin ethers were isolated from the aforementioned fractions: conferone (1) [26], conferol (2) [27], feselol (3) [27], badrakemone (4) [28], mogoltadone (5) [29], farnesiferol A (6) [30], farnesiferol A acetate (7) [31], gummosin (8) [32], ferukrin (9) [33], ferukrin acetate (10) [33], deacetylkellerin (11) [34], kellerin (12) [35], samarcandone (13) [36], samarcandin (14) [37], and samarcandin acetate (15) (Figure 1). Due to the availability of limited NMR data for the isolated cytotoxic coumarins in the literature, extensive 2D NMR spectroscopic techniques, such as 2D 1 H-1 H correlation spectroscopy (COSY), nuclear Overhauser effect spectroscopy (NOESY), heteronuclear single-quantum coherence (HSQC), heteronuclear multiple-bond connectivity (HMBC), (Supplementary Materials Figures S2-S91) as well as high-resolution mass spectroscopy (HRMS) and optical rotation measurements (Supplementary Materials Table S1), were used for the confirmation of their structures.…”

Section: Bioactivity-directed Isolation and Structure Elucidation Of ...mentioning

confidence: 99%

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Sesquiterpene Coumarin Ethers with Selective Cytotoxic Activities from the Roots of Ferula huber-morathii Peşmen (Apiaceae) and Unequivocal Determination of the Absolute Stereochemistry of Samarcandin

Eruçar,

Kuran,

Altıparmak Ülbegi

et al. 2023

Pharmaceuticals

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Ancient physicians frequently used the resin of Ferula species to treat cancer. Today, some folkloric recipes used for cancer treatment also contain the resin of Ferula species. The dichloromethane extract of the roots of Ferula huber-morathii exhibited cytotoxic activities against COLO 205 (colon), K-562 (lymphoblast), and MCF-7 (breast) cancer cell lines (IC50 = 52 µg/mL, 72 µg/mL, and 20 µg/mL, respectively). Fifteen sesquiterpene coumarin ethers with cytotoxic activity were isolated from the dichloromethane extract of the roots of F. huber-morathii using bioactivity-directed isolation studies. Extensive spectroscopic analyses and chemical transformations have elucidated the structures of these sesquiterpene coumarin ethers as conferone (1), conferol (2), feselol (3), badrakemone (4), mogoltadone (5), farnesiferol A (6), farnesiferol A acetate (7), gummosin (8), ferukrin (9), ferukrin acetate (10), deacetylkellerin (11), kellerin (12), samarcandone (13), samarcandin (14), and samarcandin acetate (15). The absolute configuration of samarcandin (14) was unequivocally determined by the X-ray crystallographic analysis of the semi-synthetic (R)-MTPA ester of samarcandin (24). Conferol (2) and mogoltadone (5) were found to be the most potent cytotoxic compounds against all three cancer cell lines; furthermore, these compounds exhibit low cytotoxic activity against the non-cancerous human umbilical vein epithelial cells (HUVEC) cell line. Investigation of the biological activity mechanisms of mogoltadone (5) revealed that while suppressing the levels of Bcl-XL and procaspase-3 in the COLO 205 cancer cell line, it did not have a significant effect on the Bcl-XL, caspase-3, and β-catenin protein levels of the HUVEC cell line, which may explain the cytotoxic selectivity of mogoltadone (5) on cancer cell lines.

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Isolation, spectroscopic characterization, X-ray, theoretical studies as well as in vitro cytotoxicity of Samarcandin

Cited by 15 publications

References 30 publications

In Silico Evaluation of Iranian Medicinal Plant Phytoconstituents as Inhibitors against Main Protease and the Receptor-Binding Domain of SARS-CoV-2

In Silico Evaluation of Iranian Medicinal Plant Phytoconstituents as Inhibitors against Main Protease and the Receptor-Binding Domain of SARS-CoV-2

Next Chapter in the Legend of Silphion: Preliminary Morphological, Chemical, Biological and Pharmacological Evaluations, Initial Conservation Studies, and Reassessment of the Regional Extinction Event

Sesquiterpene Coumarin Ethers with Selective Cytotoxic Activities from the Roots of Ferula huber-morathii Peşmen (Apiaceae) and Unequivocal Determination of the Absolute Stereochemistry of Samarcandin

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