RT journal article
T1 Isolation and Identification of 12-Deoxyphorbol Esters from Euphorbia resinifera Berg Latex: Targeted and Biased Non-Targeted Identification of 12-Deoxyphorbol Esters by UHPLC-HRMSE
A1 Ezzanad, Abdellah
A1 Reyes Jiménez, Carolina de los
A1 Macías Sánchez, Antonio José
A1 Hernández Galán, Rosario
A2 Química Orgánica
K1 Euphorbiaceae
K1 Euphorbia resinifera Berg
K1 diterpenes
K1 12-deoxyphorbols
K1 absolute configuration
K1 UHPLC
K1 HRMS
AB Diterpenes from the Euphorbia genus are known for their ability to regulate the proteinkinase C (PKC) family, which mediates their ability to promote the proliferation of neural precursorcells (NPCs) or neuroblast differentiation into neurons. In this work, we describe the isolationfrom E. resinifera Berg latex of fifteen 12-deoxyphorbol esters (1–15). A triester of 12-deoxy-16-hydroxyphorbol (4) and a 12-deoxyphorbol 13,20-diester (13) are described here for the first time.Additionally, detailed structural elucidation is provided for compounds 3, 5, 6, 14 and 15. Theabsolute configuration for compounds 3, 4, 6, 13, 14 and 15 was established by the comparisonof their theoretical and experimental electronic circular dichroism (ECD) spectra. Access to theabove-described collection of 12-deoxyphorbol derivatives, with several substitution patterns andattached acyl moieties, allowed for the study of their fragmentation patterns in the collision-induceddissociation of multiple ions, without precursor ion isolation mass spectra experiments (HRMSE),which, in turn, revealed a correlation between specific substitution patterns and the fragmentationpathways in their HRMSE spectra. In turn, this allowed for a targeted UHPLC-HRMSE analysis and abiased non-targeted UHPLC-HRMSE analysis of 12-deoxyphorbols in E. resinifera latex which yieldedthe detection and identification of four additional 12-deoxyphorbols not previously isolated in theinitial column fractionation work. One of them, identified as 12-deoxy-16-hydroxyphorbol 20-acetate13-phenylacetate 16-propionate (20), has not been described before.
PB Multidisciplinary Digital Publishing Institute (MDPI)
SN 2223-7747
YR 2023
FD 2023
LK http://hdl.handle.net/10498/31950
UL http://hdl.handle.net/10498/31950
LA eng
DS Repositorio Institucional de la Universidad de Cádiz
RD 21-sep-2026