17633-81-7Relevant articles and documents
Anti-tumour activity of two 19-nor-clerodane diterpenes, trans- dehydrocrotonin and trans-crotonin, from Croton cajucara
Grynberg, Noema F.,Echevarria, Aurea,Lima, Juliana E.,Pamplona, Sonia S. R.,Pinto, Angelo C.,Maciel, Maria Aparecida M.
, p. 687 - 689 (1999)
The effects of two nor-diterpenes, trans-dehydrocrotonin (DCTN) and trans-crotonin (CTN) from Croton cajucara (Euphorbiaceae), on the survival of mice bearing Sarcoma 180 and Ehrlich carcinoma ascitic tumours, on the proliferation of cultured Ehrlich cells and TNFα activity were determined. When the mice were treated with 80 and 120 mg/kg of DCTN or 38 mg/kg of 5-FU a significant anti-tumour activity was obtained (%T/C of 128-140). The cytotoxicity against Ehrlich carcinoma was 16 μM for DCTN and CTN whereas the flavonoid quercetin was cytotoxic at 44 μM in 48 h cell culture. No apoptosis was seen on in vitro electrophoresis of DNA extracted from the tumour cells treated with DCTN and CTN. A significant TNFα activity was detected in Ehrlich tumour-bearing mice treated with DCTN suggesting an enhanced immune function.
Synthesis, NMR data and theoretical study of semi-synthetic derivatives from trans-dehydrocrotonin
Soares, Breno Almeida,Medeiros Maciel, Maria Aparecida,Castro, Rosane Nora,Kaiser, Carlos R.,Firme, Caio Lima
, p. 533 - 541 (2016)
In this work, the 19-nor-diterpenoid clerodane-type dehydrocrotonin (t-DCTN) was a primary source for a two-step synthetic procedure. The catalytic hydrogenation of t-DCTN afforded the semi-synthetic trans-crotonin (t-CTN) in a highly stereospecific reaction confirmed by DFT calculations. The unsaturated carbonyl group of t-DCTN was reduced by NaBH4/EtOH providing an epimeric α-OH and β-OH mixture named t-CTN-OL. Both epimeric compound structures t-CTN-α-OL and t-CTN-β-OL were elucidated by 1D and 2D NMR spectral data. Comparison of NMR data from natural source of t-CTN was done to confirm the stereochemical authenticity of semi-synthetic t-CTN. Calculated NMR data for all described derivatives (semi-synthetic t-CTN and its t-CTN-OL epimeric mixture) were performed using B3LYP/6-311G++(d,p) level of theory which validated our previously developed NMR theoretical protocol for structural analyses of organic molecules. Topological data using Quantum Theory of Atoms in Molecules (QTAIM) of t-CTN quantified and qualified intramolecular interactions of its most stable conformer.
