Chlorinated Guaiane-Type Sesquiterpene Lactones as Cytotoxic Agents against Human Tumor Cells

Estévez-Sarmiento, Francisco; Saavedra, Ester; Ruiz-Estévez, Mercedes; León, Francisco; Quintana, José; Brouard, Ignacio; Estévez, Francisco

doi:10.3390/ijms21249767

Cited by 10 publications

(6 citation statements)

References 30 publications

(43 reference statements)

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“…The effects of guaiane‐type sesquiterpene lactones from genus Centaurea were evaluated against the human leukemia cell lines. Chlorohyssopifolins A, C, and D and linichlorin A showed an IC50 of about 10 μM in all cell lines [60] . In summary, the compounds studied in the current research showed a lower cytotoxic effect in comparison with similar compounds evaluated in the previous study.…”

Section: Resultssupporting

confidence: 48%

“…Chlorohyssopifolins A, C, and D and linichlorin A showed an IC50 of about 10 μM in all cell lines. [60] In summary, the compounds studied in the current research showed a lower cytotoxic effect in comparison with similar compounds evaluated in the previous study. Between these two compounds, compound 2 is more cytotoxic than compound 1 and exhibited a lower toxic effect on normal cells.…”

Section: Cytotoxicity Activitysupporting

confidence: 57%

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Evaluation of Cytotoxic and Antioxidant Effect of Guaianolid Sesquiterpenes fromFerula hindukushensis

Mehrabani,

Iranshahi,

Mehrabani

et al. 2023

ChemistrySelect

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Ferula species have been recognized as crucial medicinal plants that are known for producing a variety of sesquiterpenes, such as sesquiterpene lactones and sesquiterpene coumarins. However, guaianolide sesquiterpenes, which are sesquiterpene lactones that contain an alpha‐methylene‐gamma‐lactone moiety, are rare in Ferula spp. Ferula hindukushensis, an endemic species found in Afghanistan, Pakistan, and Iran, belongs to the Ferula genus. In this study, the normal column chromatography technique was employed to fractionate the dichloromethane extract of F. hindukushensis. The structures of two guaianolide sesquiterpenes were identified using various nuclear magnetic resonance (NMR) spectra, such as 13C NMR, 1H NMR, and heteronuclear multiple bond correlation (HMBC), and were compared with the literature interpretation to confirm their structural characteristics. Moreover, the 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyl‐2H‐tetrazolium bromide (MTT) assay was employed to examine the cytotoxicity of guaianolide compounds on various cell lines, including MCF‐7, 3T3, HT‐29, MCF‐10, PC12, and A549. The antioxidant effects of these compounds were evaluated using ferric reducing antioxidant power (FRAP) and 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH) assays. The findings indicated that the antioxidant activity of the compounds was lower than that of vitamin C at the same concentration. The cytotoxic effects of the compounds varied depending on the cell types. Nevertheless, except for HT‐29, a concentration lower than 125 μg/mL was found to be non‐toxic for all cell lines.

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Section: Resultssupporting

confidence: 48%

Section: Cytotoxicity Activitysupporting

confidence: 57%

Evaluation of Cytotoxic and Antioxidant Effect of Guaianolid Sesquiterpenes fromFerula hindukushensis

Mehrabani,

Iranshahi,

Mehrabani

et al. 2023

ChemistrySelect

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“…To obtain an analogue of chlorine-containing biologically active guaianolides [ 20 , 21 , 22 , 23 ], we studied the interaction of estafiatin 1 with a solution of hydrogen chloride in methanol. This formed a mixture of two substances with R f 0.55 and 0.45.…”

Section: Resultsmentioning

confidence: 99%

Syntheses Based on 3,4α-Epoxy-1,5,7α,6β(H)-guai-10(14),11(13)-dien-6,12-olide

Адекенов¹

2022

Molecules

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The sesquiterpene γ-lactone estafiatin 1, the molecule of which has a structure of 3,4α-epoxy-1,5,7α,6β(H)-guai-10(14),11(13)-dien-6,12-olide, is characteristic of plants of the genera Achillea L. and Artemisia L. of the Asteraceae family. This article presents the results of chemical modification for three reaction centers of the estafiatin molecule 1: epoxy cycle, exomethylene group conjugated with γ-lactone carbonyl, and exomethylene group in position С10=С14; and at the same time 33 new derivatives were synthesized, the structures of which were established based on physicochemical constants, spectral data (IR-, PMR-, 13C-NMR), and X-ray diffraction analysis. The stereo- and regiospecificity, as well as the chemoselectivity of the reaction based on estafiatin molecule 1, are discussed. The reactivity of the substrate is significantly influenced by the stereochemistry of its molecule, the nature of the reagent, and the reaction medium. Based on the results of in silico screening, derivatives of estafiatin with high binding energies for both DNA-topoisomerase I and DNA-topoisomerase II were identified. The values of the inhibitory dose of IC50 for estafiatin 1 and its derivatives were determined on cell lines of eight types of tumors. In vivo experiments of the samples made it possible to establish that estafiatin 1 and its derivatives have pronounced antitumor activity against Pliss lymphosarcoma, Walker’s carcinosarcoma, sarcoma 45, sarcoma-180, alveolar liver cancer PC-1, leukemia P-388 and L-1210, and sarcoma-45 resistant to 5-fluorouracil.

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“…3.4 µM and 3.6 µM (72 h), respectively. Of note, chlorohyssopifolin C and D also showed IC 50 values below 10 µM [108].…”

Section: Other Sesquiterpenoidsmentioning

confidence: 94%

Plant-Derived Terpenoids: A Promising Tool in the Fight against Melanoma

Kłos

Chlubek

2022

Cancers

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Melanoma is responsible for the highest number of skin cancer-caused deaths worldwide. Despite the numerous melanoma-treating options, the fight against it remains challenging, mainly due to its great heterogeneity and plasticity, as well as the high toxicity of standard drugs. Plant-derived terpenoids are a group of plant defense molecules that have been proven effective in killing many different types of cancer cells, both in in vitro experiments and in vivo models. In this review, we focus on recent results in the search for plant terpenoids with anti-melanoma activity. We also report on the synergistic action of combining terpenoids with other plant-derived substances, MAP kinase inhibitors, or radiation. Additionally, we present examples of terpenoid-loaded nanoparticle carriers as anti-melanoma agents that have increased permeation through the cancer tissue.

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Chlorinated Guaiane-Type Sesquiterpene Lactones as Cytotoxic Agents against Human Tumor Cells

Cited by 10 publications

References 30 publications

Evaluation of Cytotoxic and Antioxidant Effect of Guaianolid Sesquiterpenes fromFerula hindukushensis

Evaluation of Cytotoxic and Antioxidant Effect of Guaianolid Sesquiterpenes fromFerula hindukushensis

Syntheses Based on 3,4α-Epoxy-1,5,7α,6β(H)-guai-10(14),11(13)-dien-6,12-olide

Plant-Derived Terpenoids: A Promising Tool in the Fight against Melanoma

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