Cytotoxic Diterpenoids from <i>Euphorbia fischeriana</i>

Meng, Jia; Li, Bo Ting; Sheng, Gang; Zhang, An Ling; Li, Xing Cong; Tian, Jun‐Mian

doi:10.1002/cbdv.202000919

Cited by 10 publications

(9 citation statements)

References 23 publications

(20 reference statements)

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“…Despite abietane diterpenes considered as one of the main metabolites in Euphorbia genus, ent‐abietatriene‐type diterpenes have been reported in few species like E. guyoniana , [67] E. pekinensis , [68] E. fischeriana , [69] E. dracunculoides , [70] and E. usambarica [71] . Here, five ent‐abietatrienes, compounds ( 3 – 7 ), were tentatively identified in the extracts of E. mauritanica that designed these compounds as characteristic chemotaxonomic marker of this species.…”

Section: Resultsmentioning

confidence: 87%

Integration of LC/MS, NMR and Molecular Docking for Profiling of Bioactive Diterpenes from Euphorbia mauritanica L. with in Vitro Anti‐SARS‐CoV‐2 Activity

Essa¹,

El‐Hawary

Kubacy³

et al. 2023

Chemistry & Biodiversity

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In spite of tremendous efforts exerted in the management of COVID-19, the absence of specific treatments and the prevalence of delayed and long-term complications termed post-COVID syndrome still urged all concerned researchers to develop a potent inhibitor of SARS-Cov-2. The hydromethanolic extracts of different parts of E. mauritanica were in vitro screened for anti-SARS-Cov-2 activity. Then, using an integrated strategy of LC/MS/MS, molecular networking and NMR, the chemical profile of the active extract was determined. To determine the optimum target for these compounds, docking experiments of the active extract's identified compounds were conducted at several viral targets. The leaves extract showed the best inhibitory effect with IC 50 8.231 � 0.04 μg/ml. The jatrophane diterpenes were provisionally annotated as the primary metabolites of the bioactive leaves extract based on multiplex of LC/MS/MS, molecular network, and NMR. In silico studies revealed the potentiality of the compounds in the most active extract to 3CLpro, where compound 20 showed the best binding affinity. Further attention should be paid to the isolation of various jatrophane diterpenes from Euphorbia and evaluating their effects on SARS-Cov-2 and its molecular targets.

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Section: Resultsmentioning

confidence: 87%

Integration of LC/MS, NMR and Molecular Docking for Profiling of Bioactive Diterpenes from Euphorbia mauritanica L. with in Vitro Anti‐SARS‐CoV‐2 Activity

Essa¹,

El‐Hawary

Kubacy³

et al. 2023

Chemistry & Biodiversity

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“…The 1 H NMR spectrum of 1 displayed signal for three aliphatic methyl protons at δ H 0.90 (3 H, s), 0.75 (3 H, s) and 0.57 (3 H, s), a methoxy protons at δ H 3.75 (3 H, s), an oxygenated methylene proton at δ H 4.78 (2H, d, J = 9.0 Hz), and oxygenated methine protons at δ H 4.33 (1H, s)]. The 13 C NMR and DEPT 135° spectra of 1 showed 21 carbon resonances, of which the resonances at δ C 191.9, 175.9 and 111.4, together with the HSQC spectrum, indicated the presence of an α,β‐unsaturated ketone.…”

Section: Resultsmentioning

confidence: 97%

“…Diterpenoids in Euphorbia own excellent cytotoxicity to a variety of cancer cell. [ 13‐15 ] In the process of searching for new cancer inhibitors from traditional Chinese medicine, a series of eABDs were isolated from the extract of E. fischeriana , including four new diterpenoids ( 1 — 4 ) and eleven analogues ( 5 — 15 ) (Figure 1). Their structures and absolute configurations were determined based on single‐crystal X‐ray diffraction, Rh 2 (OCOCF 3 ) 4 ‐induced CD spectrum, and calculated ECD spectra.…”

Section: Background and Originality Contentmentioning

confidence: 99%

Discovery of Highly Oxidized Abietane Diterpenoids from the Roots of Euphorbia fischeriana with Anti‐tumor Activities

et al. 2021

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Main observation and conclusion Four previously undescribed ent‐abietane diterpenoids (1—4), along with eleven known analogues (5—15), were isolated from the roots of wild Euphorbia fischeriana. Their gross structures were determined via extensive spectroscopic data, and the absolute configurations were elucidated by means of single‐crystal X‐ray diffraction analysis, Rh2(OCOCF3)4‐induced CD spectrum and ECD calculations. Their cervical carcinoma inhibition activities counteract HeLa cells were screened by MTT assay, and the structure‐activity relationships were further examined. The results demonstrated that 2 (IC50 value at 3.75 μmol/L) was more potent than cisplatin. The underlying mechanism study revealed that 2 could distinctly induce apoptosis accompanied by increasing reactive oxygen species (ROS) production, Ca2+ influx and decreasing mitochondrial membrane potential. Furthermore, signal pathways including MAPKs/AKT might play a significant role in 2‐induced cervical cancer cells death.

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“…A set of characteristic product ions were attributed to skeleton residues, which were obtained by the cleavage of rings. Then, diterpenoids from 70% ethanol fraction were identified by comparing formulas and fragmentation patterns with accurate target diterpenoids searching from the literature [ 4 , 19 – 44 ].…”

Section: Resultsmentioning

confidence: 99%

Integrated Strategy of UHPLC-Q-TOF-MS and Molecular Networking for Identification of Diterpenoids from Euphorbia fischeriana Steud. and Prediction of the Anti-Breast-Cancer Mechanism by the Network Pharmacological Method

Zhang

et al. 2021

Evidence-Based Complementary and Alternative Medicine

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Breast cancer is one of the most common malignancies in women worldwide. Traditional Chinese medicine has been used as adjunctive or complementary therapy for breast cancer. Diterpenoids from Euphorbia fischeriana Steud. have been demonstrated to possess anti-breast-cancer activity. This research was aimed to systematically explore the diterpenoids from E. fischeriana and study the multiple mechanisms on breast cancer. The structures of diterpenoids were identified by the integrated strategy of UHPLC-Q-TOF-MS and molecular networking. A total of 177 diterpenoids belonging to 13 types were collected. In silico ADME analysis was performed on these compounds. It indicated that 130 of 177 diterpenoids completely adjusted to Lipinski’s rule. The targets of compounds were obtained from PharmMapper. The targets of breast cancer were collected from GeneCards. Then, 197 compounds-related targets and 544 breast cancer-related targets were identified. After the intersection process, 58 overlapping targets between compounds-related targets and breast cancer-related targets were acquired. The STRING database was applied to predict the protein-protein interactions. The GO and KEGG pathway enrichment analysis were performed by using the KOBAS database. It indicated that these predicted pathways were closely related to breast cancer. The treatment effect of E. fischeriana on breast cancer might be performed through signaling pathways, such as IL-17 signaling pathway, MAPK signaling pathway, and PI3K-Akt signaling pathway. The predicted top genes such as EGFR, ESR, MAPK, SRC, CASP3, CDK2, and KDR were involved in cell proliferation, gene transcription, apoptosis, signal transduction, DNA damage and repair, tumor differentiation, metastasis, and cell cycle, which indicated that E. fischeriana might treat breast cancer comprehensively. A compounds-KEGG pathways-related targets network was built by using cytoHubba to analyze the hub compounds and targets. It concluded that E. fischeriana treated breast cancer not only by the main components but also by the microconstituents, which reflected the overall regulatory role of multicomponents treating breast cancer. To estimate the binding affinities, binding sites, and binding postures, molecular docking simulations between 177 diterpenoids and top 19 targets were carried out. The results are basically in line with expectations. In conclusion, these results can serve as references for researchers studying potential targets of diterpenoids from E. fischeriana on breast cancer in the future.

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Cytotoxic Diterpenoids from Euphorbia fischeriana

Cited by 10 publications

References 23 publications

Integration of LC/MS, NMR and Molecular Docking for Profiling of Bioactive Diterpenes from Euphorbia mauritanica L. with in Vitro Anti‐SARS‐CoV‐2 Activity

Integration of LC/MS, NMR and Molecular Docking for Profiling of Bioactive Diterpenes from Euphorbia mauritanica L. with in Vitro Anti‐SARS‐CoV‐2 Activity

Discovery of Highly Oxidized Abietane Diterpenoids from the Roots of Euphorbia fischeriana with Anti‐tumor Activities

Integrated Strategy of UHPLC-Q-TOF-MS and Molecular Networking for Identification of Diterpenoids from Euphorbia fischeriana Steud. and Prediction of the Anti-Breast-Cancer Mechanism by the Network Pharmacological Method

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