Cytotoxic activity of several ent-kaurane derivatives of atractyligenin. Synthesis of unreported diterpenic skeleton by chemical rearrangement

Badalamenti, Natale; Vaglica, A.; Maggio, Antonella; Bruno, Maurizio; Quassinti, Luana; Bramucci, Massimo; Maggi, Filippo

doi:10.1016/j.phytochem.2022.113435

Cited by 3 publications

(3 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Atractyligenin (1) was extracted from the dried roots of C. gummifer Cass. as previously reported [43].…”

Section: Isolation Of the Atractyligenin (1)supporting

confidence: 80%

“…In 2022 it was demonstrated that synthetic modifications (bromination, reduction, elimination, and oxidation) on the A ring of 1 modulated its antitumor activity, significantly increasing the antiproliferative efficacy in some cases [43].…”

Section: Introductionmentioning

confidence: 99%

“…d, 6.6 Hz, CH-3 ′ ), 0.91 (3H, d, 6.6 Hz, CH 3 -4 ′ ), 0.91 (3H, d, 6.6 Hz, CH 3 -5 ′ ), 1.06 (3H, d, 6.6 Hz, CH 3 -6 ′ ) (Figure S78); 13 C-NMR (CDCl 3 -d 1 , 62.5 MHz) δ 55.45 (C-1), 209.99 (C-2), 43.64 (C-3), 47.38 (C-4), 48.46 (C-5), 24.63 (C-6), 33.04 (C-7), 51.79 (C-8), 50.65 (C-9), 44.49 (C-10), 18.14 (C-11), 31.69 (C-12), 37.85 (C-13), 35 25.15 (C-3 ′ ), 22.65 (C-4 ′ ), 22.49 (C-5 ′ ), 20.54 (C-6 ′ ) (Figure S79); HRESIMS m/z 400.2861 [M + H] + (calcd. for C 25 H 37 NO 3 , 400.2846) (Figure S80).…”

mentioning

confidence: 99%

See 2 more Smart Citations

Synthetic Derivatives of Natural ent-Kaurane Atractyligenin Disclose Anticancer Properties in Colon Cancer Cells, Triggering Apoptotic Cell Demise

Badalamenti,

Maggio,

Fontana

et al. 2024

IJMS

Self Cite

View full text Add to dashboard Cite

The antitumor activity of different ent-kaurane diterpenes has been extensively studied. Several investigations have demonstrated the excellent antitumor activity of synthetic derivatives of the diterpene atractyligenin. In this research, a series of new synthetic amides and their 15,19-di-oxo analogues obtained from atractyligenin by modifying the C-2, C-15, and C-19 positions were designed in order to dispose of a set of derivatives with different substitutions at the amidic nitrogen. Using different concentrations of the obtained compounds (10–300 μM) a reduction in cell viability of HCT116 colon cancer cells was observed at 48 h of treatment. All the di-oxidized compounds were more effective than their alcoholic precursors. The di-oxidized compounds had already reduced the viability of two colon cancer cells (HCT116 and Caco-2) at 24 h when used at low doses (2.5–15 μM), while they turned out to be poorly effective in differentiated Caco-2 cells, a model of polarized enterocytes. The data reported here provide evidence that di-oxidized compounds induced apoptotic cell death, as demonstrated by the appearance of condensed and fragmented DNA in treated cells, as well as the activation of caspase-3 and fragmentation of its target PARP-1.

show abstract

“…Atractyligenin (1) was extracted from the dried roots of C. gummifer Cass. as previously reported [43].…”

Section: Isolation Of the Atractyligenin (1)supporting

confidence: 80%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

See 1 more Smart Citation

Synthetic Derivatives of Natural ent-Kaurane Atractyligenin Disclose Anticancer Properties in Colon Cancer Cells, Triggering Apoptotic Cell Demise

Badalamenti,

Maggio,

Fontana

et al. 2024

IJMS

Self Cite

View full text Add to dashboard Cite

show abstract

Structural characterization of carboxyatractyloside and acaricidal activity of natural ent-kaurene diterpenoids isolated from Chamaeleon gummifer against Tetranychus urticae

Badalamenti,

Bruno,

Pavela

et al. 2023

J Pest Sci

View full text Add to dashboard Cite

Plant-borne secondary metabolites are attracting high interest for their potential use in agricultural applications, with special reference to the control of arthropod pests. In the present work, the structural elucidation of glycosylated diterpenoid carboxyatractyloside (2) isolated from the roots of Chamaeleon gummifer Cass. (Asteraceae) is reported by means of spectroscopic and spectrometric techniques. Complete identification occurred thanks to one- and two-dimensional NMR experiments, assigning the single protons and carbons, and the stereochemistry by the NOESY correlations. Carboxyatractyloside (2), together with two ent-kaurenes atractyloside (1) and atractyligenin (3), extracted from the roots of C. gummifer, have been tested for their acaricidal and oviposition inhibition activity against the two-spotted spider mite, Tetranychus urticae Koch (Acari: Tetranychidae) Notably, compounds 1–3 were toxic to T. urticae, leading to significant mortality, oviposition inhibition, reduced hatchability of eggs, and natality inhibition. However, at the lowest dose (12.5 µg cm−2) compound 2 was the most effective, leading to mortality > 60% after 5 days exposure, inhibiting oviposition by > 70% and egg hatching by 33%; it also reduced natality by 80%. Overall, these compounds represent valuable candidates to develop novel acaricides for crop protection. Further research on how to develop stable formulations for field use, as well as on non-target effects of these compounds on pollinators and mite biocontrol agents, is ongoing.

show abstract

Derivatives of atractyligenin in coffee

Lang

2025

Coffee in Health and Disease Prevention

View full text Add to dashboard Cite

Cytotoxic activity of several ent-kaurane derivatives of atractyligenin. Synthesis of unreported diterpenic skeleton by chemical rearrangement

Cited by 3 publications

References 33 publications

Synthetic Derivatives of Natural ent-Kaurane Atractyligenin Disclose Anticancer Properties in Colon Cancer Cells, Triggering Apoptotic Cell Demise

Synthetic Derivatives of Natural ent-Kaurane Atractyligenin Disclose Anticancer Properties in Colon Cancer Cells, Triggering Apoptotic Cell Demise

Structural characterization of carboxyatractyloside and acaricidal activity of natural ent-kaurene diterpenoids isolated from Chamaeleon gummifer against Tetranychus urticae

Derivatives of atractyligenin in coffee

Contact Info

Product

Resources

About