Structure elucidation and absolute configuration determination of nortriterpenoids from Picramnia glazioviana
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Structure elucidation and absolute configuration determination of nortriterpenoids from Picramnia glazioviana. / Gimenes, Leila; Luna-Dulcey, Liany; Batista Junior, Joao Marcos; dos Santos Junior, Fernando Martins; Popolin, Cecilia P.; Cominetti, Marcia Regina; Fernandes, Joao Bastita; Stærk, Dan.
I: Journal of Natural Products, Bind 83, 2020, s. 1859-1876.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
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TY - JOUR
T1 - Structure elucidation and absolute configuration determination of nortriterpenoids from Picramnia glazioviana
AU - Gimenes, Leila
AU - Luna-Dulcey, Liany
AU - Batista Junior, Joao Marcos
AU - dos Santos Junior, Fernando Martins
AU - Popolin, Cecilia P.
AU - Cominetti, Marcia Regina
AU - Fernandes, Joao Bastita
AU - Stærk, Dan
PY - 2020
Y1 - 2020
N2 - In this study, HPLC-PDA-HRMS-SPE-NMR data were used for initial analysis of the CH2Cl2 fraction of an EtOH extract of the leaves of Picramnia glazioviana. The HRMS, UV, and NMR data obtained from the HPLC-PDA-HRMS-SPE-NMR analysis were used to direct semipreparative HPLC isolation towards nortriterpenoids, which resulted in isolation of 18 new and highly oxygenated nortriterpenoids (1-3, 5-10, 12-19, and 21), named picravianes C-T. Their structures were determined on the basis of analysis of UV, HRMS, and 2D NMR spectroscopic data, including determination of the relative configuration on the basis of coupling pattern analysis and nuclear Overhauser effect correlations. The absolute configurations of compounds 7, 9, 10, 14, 15, 17, 18, 19, and 21 were assigned using electronic circular dichroism (ECD) data, and the cytotoxicity of compounds 6, 10, 14, 16, 17, 18, 19, and 21 was evaluated against MDA-MB-231 triple negative breast cancer, SKBR-3 Her2-overexpressing breast cancer, and A549 lung cancer cells lines. The isolated compounds contain a hitherto undescribed modification of the terminal backbone and/or E-ring, and a possible biosynthetic pathway for their formation is proposed.
AB - In this study, HPLC-PDA-HRMS-SPE-NMR data were used for initial analysis of the CH2Cl2 fraction of an EtOH extract of the leaves of Picramnia glazioviana. The HRMS, UV, and NMR data obtained from the HPLC-PDA-HRMS-SPE-NMR analysis were used to direct semipreparative HPLC isolation towards nortriterpenoids, which resulted in isolation of 18 new and highly oxygenated nortriterpenoids (1-3, 5-10, 12-19, and 21), named picravianes C-T. Their structures were determined on the basis of analysis of UV, HRMS, and 2D NMR spectroscopic data, including determination of the relative configuration on the basis of coupling pattern analysis and nuclear Overhauser effect correlations. The absolute configurations of compounds 7, 9, 10, 14, 15, 17, 18, 19, and 21 were assigned using electronic circular dichroism (ECD) data, and the cytotoxicity of compounds 6, 10, 14, 16, 17, 18, 19, and 21 was evaluated against MDA-MB-231 triple negative breast cancer, SKBR-3 Her2-overexpressing breast cancer, and A549 lung cancer cells lines. The isolated compounds contain a hitherto undescribed modification of the terminal backbone and/or E-ring, and a possible biosynthetic pathway for their formation is proposed.
U2 - 10.1021/acs.jnatprod.0c00045
DO - 10.1021/acs.jnatprod.0c00045
M3 - Journal article
C2 - 32530627
VL - 83
SP - 1859
EP - 1876
JO - Journal of Natural Products
JF - Journal of Natural Products
SN - 0163-3864
ER -
ID: 241226201