Secondary Metabolites with Anti-Inflammatory Activity from Laurencia majuscula Collected in the Red Sea
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Secondary Metabolites with Anti-Inflammatory Activity from Laurencia majuscula Collected in the Red Sea. / Tammam, Mohamed A.; Daskalaki, Maria G. G.; Tsoureas, Nikolaos; Kolliniati, Ourania; Mahdy, Aldoushy; Kampranis, Sotirios C.; Tsatsanis, Christos; Roussis, Vassilios; Ioannou, Efstathia.
I: Marine Drugs, Bind 21, Nr. 2, 79, 2023.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
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T1 - Secondary Metabolites with Anti-Inflammatory Activity from Laurencia majuscula Collected in the Red Sea
AU - Tammam, Mohamed A.
AU - Daskalaki, Maria G. G.
AU - Tsoureas, Nikolaos
AU - Kolliniati, Ourania
AU - Mahdy, Aldoushy
AU - Kampranis, Sotirios C.
AU - Tsatsanis, Christos
AU - Roussis, Vassilios
AU - Ioannou, Efstathia
PY - 2023
Y1 - 2023
N2 - The chemical investigation of the organic extract of the red alga Laurencia majuscula collected from Hurghada reef in the Red Sea resulted in the isolation of five C-15 acetogenins, including four tricyclic ones of the maneonene type (1-4) and a 5-membered one (5), 15 sesquiterpenes, including seven lauranes (6-12), one cuparane (13), one seco-laurane (14), one snyderane (15), two chamigranes (16, 17), two rearranged chamigranes (18, 19) and one aristolane (20), as well as a tricyclic diterpene (21) and a chlorinated fatty acid derivative (22). Among them, compounds 1-3, 5, 7, 8, 10, 11 and 14 are new natural products. The structures and the relative configurations of the isolated natural products have been established based on extensive analysis of their NMR and MS data, while the absolute configuration of maneonenes F (1) and G (2) was determined on the basis of single-crystal X-ray diffraction analysis. The anti-inflammatory activity of compounds 1, 2, 4-8, 10, 12-16, 18 and 20-22 was evaluated by measuring suppression of nitric oxide (NO) release in TLR4-activated RAW 264.7 macrophages in culture. All compounds, except 6, exhibited significant anti-inflammatory activity. Among them, metabolites 1, 4 and 18 did not exhibit any cytostatic activity at the tested concentrations. The most prominent anti-inflammatory activity, accompanied by absence of cytostatic activity at the same concentration, was exerted by compounds 5 and 18, with IC50 values of 3.69 mu M and 3.55 mu M, respectively.
AB - The chemical investigation of the organic extract of the red alga Laurencia majuscula collected from Hurghada reef in the Red Sea resulted in the isolation of five C-15 acetogenins, including four tricyclic ones of the maneonene type (1-4) and a 5-membered one (5), 15 sesquiterpenes, including seven lauranes (6-12), one cuparane (13), one seco-laurane (14), one snyderane (15), two chamigranes (16, 17), two rearranged chamigranes (18, 19) and one aristolane (20), as well as a tricyclic diterpene (21) and a chlorinated fatty acid derivative (22). Among them, compounds 1-3, 5, 7, 8, 10, 11 and 14 are new natural products. The structures and the relative configurations of the isolated natural products have been established based on extensive analysis of their NMR and MS data, while the absolute configuration of maneonenes F (1) and G (2) was determined on the basis of single-crystal X-ray diffraction analysis. The anti-inflammatory activity of compounds 1, 2, 4-8, 10, 12-16, 18 and 20-22 was evaluated by measuring suppression of nitric oxide (NO) release in TLR4-activated RAW 264.7 macrophages in culture. All compounds, except 6, exhibited significant anti-inflammatory activity. Among them, metabolites 1, 4 and 18 did not exhibit any cytostatic activity at the tested concentrations. The most prominent anti-inflammatory activity, accompanied by absence of cytostatic activity at the same concentration, was exerted by compounds 5 and 18, with IC50 values of 3.69 mu M and 3.55 mu M, respectively.
KW - Laurencia majuscula
KW - Red Sea
KW - acetogenins
KW - sesquiterpenes
KW - anti-inflammatory activity
KW - nitric oxide
KW - macrophages
KW - SESQUITERPENES
U2 - 10.3390/md21020079
DO - 10.3390/md21020079
M3 - Journal article
C2 - 36827120
VL - 21
JO - Marine Drugs
JF - Marine Drugs
SN - 1660-3397
IS - 2
M1 - 79
ER -
ID: 340694499