<i>Ent</i>-abietane diterpenoids from <i>Suregada zanzibariensis</i> Baill. (Euphorbiaceae), their cytotoxic and anticancer properties

Mangisa, Mandisa; Tembu, Vuyelwa Jacqueline; Fouché, Gerda; Nthambeleni, Rudzani; Peter, X.; Langat, Moses K.

doi:10.1080/14786419.2018.1470628

Cited by 11 publications

(19 citation statements)

References 9 publications

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“…were found to possess anti-cancer properties ( 10 ). Moreover, some plants of the Euphorbiaceae family such as E. bicolor , E. hirta , and S. Baill were analyzed for anti-cancer activity ( 88 – 90 ). In the positive controls, doxorubicin hydrochloride enriched the genes involved in the Cell cycle, p53 signaling pathway, and multiple cancer pathways, including breast cancer, non-small cell lung cancer, small cell lung cancer, bladder, gastric, pancreatic, and prostate cancer.…”

Section: Discussionmentioning

confidence: 99%

“…KEGG analysis results are shown in Supplemental (88)(89)(90). In the positive controls, doxorubicin hydrochloride enriched the genes involved in the Cell cycle, p53 signaling pathway, and multiple cancer pathways, including breast cancer, non-small cell lung cancer, small cell lung cancer, bladder, gastric, pancreatic, and prostate cancer.…”

Section: Analysis Of Kegg Pathway Enrichment In Different Treatmentsmentioning

confidence: 99%

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High-Throughput In Vitro Gene Expression Profile to Screen of Natural Herbals for Breast Cancer Treatment

et al. 2021

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Breast cancer has surpassed lung cancer as the most commonly diagnosed cancer in women worldwide. Some therapeutic drugs and approaches could cause side effects and weaken the immune system. The combination of conventional therapies and traditional Chinese medicine (TCM) significantly improves treatment efficacy in breast cancer. However, the chemical composition and underlying anti-tumor mechanisms of TCM still need to be investigated. The primary aim of this study is to provide unique insights to screen the natural components for breast cancer therapy using high-throughput transcriptome analysis. Differentially expressed genes were identified based on two conditions: single samples and groups were classified according to their pharmaceutical effect. Subsequently, the sample treated with E. cochinchinensis Lour. generated the most significant DEGs set, including 1,459 DEGs, 805 upregulated and 654 downregulated. Similarly, group 3 treatment contained the most DEGs (414 DEGs, 311 upregulated and 103 downregulated). KEGG pathway analyses showed five significant pathways associated with the inflammatory and metastasis processes in cancer, which include the TNF, IL−17, NF-kappa B, MAPK signaling pathways, and transcriptional misregulation in cancer. Samples were classified into 13 groups based on their pharmaceutical effects. The results of the KEGG pathway analyses remained consistent with signal samples; group 3 presents a high significance. A total of 21 genes were significantly regulated in these five pathways, interestingly, IL6, TNFAIP3, and BRIC3 were enriched on at least two pathways, seven genes (FOSL1, S100A9, CXCL12, ID2, PRS6KA3, AREG, and DUSP6) have been reported as the target biomarkers and even the diagnostic tools in cancer therapy. In addition, weighted correlation network analysis (WGCNA) was used to identify 18 modules. Among them, blue and thistle2 were the most relevant modules. A total of 26 hub genes in blue and thistle2 modules were identified as the hub genes. In conclusion, we screened out three new TCM (R. communis L., E. cochinchinensis Lour., and B. fruticosa) that have the potential to develop natural drugs for breast cancer therapy, and obtained the therapeutic targets.

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Section: Discussionmentioning

confidence: 99%

Section: Analysis Of Kegg Pathway Enrichment In Different Treatmentsmentioning

confidence: 99%

High-Throughput In Vitro Gene Expression Profile to Screen of Natural Herbals for Breast Cancer Treatment

et al. 2021

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“…138 Thus, the natural product mangiolide (6f) was more active than 6, showing cytotoxicity against human MCF-7 breast cancer and UACC62 melanoma cells, with IC 50 values of 0.13 and 0.08 μM, respectively. 139 These SAR conclusions suggest that the cancer cell cytotoxicity of JKL B may be improved by modifications at the C-8, C-11−C-14, and C-17 positions, and a conjugated C-14 carbonyl group seems important for the mediation of this type of activity. Removal of the epoxy group at the C-11 and C-12 positions decreases the cytotoxic potency of 6, but introducing a C-14 carbonyl group conjugated with double bonds at C-7(8) and C13(15) positions potentiates the cytotoxicity of 6 (Figure 14).…”

Section: ■ Diterpene Lactonesmentioning

confidence: 93%

“…De-epoxylation at the C-11 and C-12 positions resulted in the cytotoxic potency being decreased, as shown for fischeriabietane E ( 6a ), which did not display any activity toward human Bel-7402 lung, HT-29 colon, and Panc-28 pancreatic cancer cells, and jolkinolide A ( 6d ) that was much less active than 6 . , Further hydroxylation at C-17 of 6d increased its activity, as indicated by caudicifolin ( 6e ) (Figure ), , and introducing a conjugated system over C-8 and C-13–C-15 and a C-17 hydroxy group enhanced the cytotoxicity of JKL B against ANA-1 murine macrophages and Jurkat human T lymphoma cells . Thus, the natural product mangiolide ( 6f ) was more active than 6 , showing cytotoxicity against human MCF-7 breast cancer and UACC62 melanoma cells, with IC 50 values of 0.13 and 0.08 μM, respectively . These SAR conclusions suggest that the cancer cell cytotoxicity of JKL B may be improved by modifications at the C-8, C-11–C-14, and C-17 positions, and a conjugated C-14 carbonyl group seems important for the mediation of this type of activity.…”

Section: Diterpene Lactonesmentioning

confidence: 95%

Development of Potential Antitumor Agents from the Scaffolds of Plant-Derived Terpenoid Lactones

Ren

Kinghorn

2020

J. Med. Chem.

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Naturally occurring terpenoid lactones and their synthetic derivatives have attracted increasing interest for their promising antitumor activity and potential utilization in the discovery and design of new antitumor agents. In the present perspective article, selected plant-derived five-membered γ-lactones and six-membered δ-lactones that occur with terpenoid scaffolds are reviewed, with their structures, cancer cell line cytotoxicity and in vivo antitumor activity, structure–activity relationships, mechanism of action, and the potential for developing cancer chemotherapeutic agents discussed in each case. The compounds presented include artemisinin (ART, 1), parthenolide (PTL, 2), thapsigargin (TPG, 3), andrographolide (AGL, 4), ginkgolide B (GKL B, 5), jolkinolide B (JKL B, 6), nagilactone E (NGL E, 7), triptolide (TPL, 8), bruceantin (BRC, 9), dichapetalin A (DCT A, 10), and limonin (LMN, 11), and their naturally occurring analogues and synthetic derivatives. It is hoped that this contribution will be supportive of the future development of additional efficacious anticancer agents derived from natural products.

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“…The isolated diterpenoids were identified as 2-acetoxyljolkinolide A (1), jolkinolide A (2) [15], jolkinolide B (3) [16], 17-hydroxyljolkinolide A (4) [17], 17-hydroxyljolkinolide B (5) [17], 17-acetyljolkinolide A (6) [17], 17-acetyljolkinolide B (7) [18], jolkinolide E (8) [19], euphopilolide (9) [20], ent-abieta-8,11,13-triene-7-one (10) [21], 6β-hydroxy-ent-abieta-8,11,13-triene (11) [22] according to the literature. The spectra were shown in the Supplementary Materials.…”

Section: Structure-activity Relationshipmentioning

confidence: 99%

Chemical Composition, Anti-Breast Cancer Activity and Extraction Techniques of Ent-Abietane Diterpenoids from Euphorbia fischeriana Steud

Chen

et al. 2022

Molecules

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Ent-abietane diterpenoids are the main active constituents of Euphorbia fischeriana. In the continuing search for new anti-breast cancer drugs, 11 ent-abietane diterpenoids (1–11) were isolated from E. fischeriana. The structures of these compounds were clearly elucidated on the basis of 1D and 2D NMR spectra as well as HRESIMS data. Among them, compound 1 was a novel compound, compound 10 was isolated from Euphorbia genus for the first time, compound 11 was firstly discovered from E. fischeriana. These compounds exhibited varying degrees of growth inhibition against the MCF-10A, MCF-7, ZR-75-1 and MDA-MB-231 cell lines in vitro. The experimental data obtained permit us to identify the roles of the epoxy group, hydroxyl group and acetoxyl group on their cytotoxic activities. Extraction is an important means for the isolation, identification, and application of valuable compounds from natural plants. To maximize yields of ent-abietane diterpenoids of E. fischeriana, 17-hydroxyjolkinolide B, jolkinolide B, 17-hydroxyjolkinolide A and jolkinolide A were selected as quality controls to optimize the salting-out-assisted liquid–liquid extraction (SALLE) by response surface methodology (RSM). The optimized conditions for SALLE were 0.47 g sodium dihydrogen phosphate, 5.5 mL acetonitrile and 4.5 mL water at pH 7.5. The experimental values of 17-hydroxyjolkinolide B, jolkinolide B, 17-hydroxyjolkinolide A and jolkinolide A (2.134, 0.529, 0.396, and 0.148 mg/g, respectively) were in agreement with the predicted values, thus demonstrating the appropriateness of the model.

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Ent-abietane diterpenoids from Suregada zanzibariensis Baill. (Euphorbiaceae), their cytotoxic and anticancer properties

Cited by 11 publications

References 9 publications

High-Throughput In Vitro Gene Expression Profile to Screen of Natural Herbals for Breast Cancer Treatment

High-Throughput In Vitro Gene Expression Profile to Screen of Natural Herbals for Breast Cancer Treatment

Development of Potential Antitumor Agents from the Scaffolds of Plant-Derived Terpenoid Lactones

Chemical Composition, Anti-Breast Cancer Activity and Extraction Techniques of Ent-Abietane Diterpenoids from Euphorbia fischeriana Steud

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