RT journal article
T1 Oxylipins from the microalgae Chlamydomonas debaryana and Nannochloropsis gaditana and their activity as TNF-α inhibitors
A1 Reyes Jiménez, Carolina de los
A1 Ávila Román, Javier
A1 Ortega Agüera, María Jesús
A1 Jara, Adelina de la
A1 García Mauriño, Sofía
A1 Motilva, Virginia
A1 Zubía Mendoza, Eva
A2 Química Orgánica
K1 Chlamydomonas debaryana
K1 Chlamydomonaceae
K1 Nannochloropsis gaditana
K1 Eustigmataceae
K1 Oxylipins
K1 Polyunsaturated hydroxy acids
K1 Anti-inflammatory activity
K1 TNF-α inhibition
AB chemical study of the microalgae Chlamydomonas debaryana and Nannochloropsis gaditana has led to the isolation of oxylipins. The samples of C. debaryana have yielded the compounds (4Z,7Z,9E,11S,13Z)-11-hydroxyhexadeca-4,7,9,13-tetraenoic acid (1), (4Z,7E,9E,13Z)-11-hydroxyhexadeca-4,7,9,13-tetraenoic acid (2), (4Z,6E,10Z,13Z)-8-hydroxyhexadeca-4,6,10,13-tetraenoic acid (3), (4Z,8E,10Z,13Z)-7-hydroxyhexadeca-4,8,10,13-tetraenoic acid (4), and (5E,7Z,10Z,13Z)-4-hydroxyhexadeca-5,7,10,13-tetraenoic acid (5), which are derived from the fatty acid 16:4Δ4,7,10,13, together with the compound (5Z,9Z,11E,15Z)-13-hydroxyoctadeca-5,9,11,15-tetraenoic acid (7) derived from coniferonic acid (18:4Δ5,9,12,15). In addition, the known polyunsaturated hydroxy acids 11-HHT (6), (5Z,9Z,11E)-13-hydroxyoctadeca-5,9,11-trienoic acid (8), (13S)-HOTE (9), (9E,11E,15Z)-13-hydroxyoctadeca-9,11,15-trienoic acid (10), 9-HOTE (11), 12-HOTE (12), 16-HOTE (13) and (13S)-HODE (14) have also been obtained. The chemical study of N. gaditana has led to the isolation of the hydroxy acid (15S)-HEPE (15) derived from EPA (20:5Δ5,8,11,14,17). The structures of the isolated compounds were established by spectroscopic means. The optical activity displayed by oxylipins 1, 2, 6, 7, 9, 10, 14, and 15 suggests the occurrence of LOX-mediated pathways in C. debaryana and N. gaditana. In anti-inflammatory assays, all the tested compounds inhibited the TNF-α production in LPS-stimulated THP-1 macrophages. The most active oxylipin was the C-16 hydroxy acid 1, which at 25 μM caused a 60% decrease of the TNF-α level.
PB Elsevier
YR 2014
FD 2014-04-01
LK http://hdl.handle.net/10498/34734
UL http://hdl.handle.net/10498/34734
LA eng
DS Repositorio Institucional de la Universidad de Cádiz
RD 07-nov-2026