Anti-inflammatory tirucallane triterpenoids from Anopyxis klaineana Pierre (Engl.), (Rhizophoraceae).
Phytochemical investigation of the stem bark extract of Anopyxis klaineana was carried out by various chromatographic techniques resulting in the isolation and characterization of three new tirucallane triterpenoids, namely 3,23-dioxotirucalla-7,24-dien-21-oic acid (1), 3,4-secotirucalla-23-oxo-4(28)7,24-trien-3,21-dioic acid (2) and 3,4-secotirucalla-4-hydroxy-23-oxo-7,24-diene-3,21-dioic acid-21-methyl ester (3), along with nine known compounds (4-12). The structural elucidation of the compounds was performed by means of high-resolution mass spectrometry (HRMS(n)), nuclear magnetic resonance (NMR), and by comparison to literature data. Although none of the isolated compounds showed antibacterial efficacy against selected environmental and clinically important pathogenic Gram-positive and -negative bacteria, they demonstrated moderate DPPH free radical scavenging properties. Furthermore, compounds 1 and 7 exhibited remarkable anti-inflammatory potential in a prostaglandin E2 (PGE2) competitive enzyme immunoassay with IC50 values of 3.63 μM and 10.23 μM, respectively.
Department of Pharmacognosy, Faculty of Pharmacy and Pharmaceutical Sciences, Kwame Nkrumah University of Science and Technology, Kumasi, Ghana; Institute of Environmental Research (INFU), Department of Chemistry and Chemical Biology, Chair of Environmental Chemistry and Analytical Chemistry, TU Dortmund, Otto-Hahn-Straße 6, 44221 Dortmund, Germany.
Evelyn Afua
EA
Mireku
Institute of Environmental Research (INFU), Department of Chemistry and Chemical Biology, Chair of Environmental Chemistry and Analytical Chemistry, TU Dortmund, Otto-Hahn-Straße 6, 44221 Dortmund, Germany.
Souvik
S
Kusari
Institute of Environmental Research (INFU), Department of Chemistry and Chemical Biology, Chair of Environmental Chemistry and Analytical Chemistry, TU Dortmund, Otto-Hahn-Straße 6, 44221 Dortmund, Germany.
Dennis
D
Eckelmann
Department of Pharmacognosy, Faculty of Pharmacy and Pharmaceutical Sciences, Kwame Nkrumah University of Science and Technology, Kumasi, Ghana.
Abraham Yeboah
AY
Mensah
Institute of Environmental Research (INFU), Department of Chemistry and Chemical Biology, Chair of Environmental Chemistry and Analytical Chemistry, TU Dortmund, Otto-Hahn-Straße 6, 44221 Dortmund, Germany.
Ferdinand M
FM
Talontsi
Institute of Environmental Research (INFU), Department of Chemistry and Chemical Biology, Chair of Environmental Chemistry and Analytical Chemistry, TU Dortmund, Otto-Hahn-Straße 6, 44221 Dortmund, Germany. Electronic address: m.spiteller@infu.tu-dortmund.de.
Michael
M
Spiteller
D000893:Anti-Inflammatory Agents / Q000302:isolation & purification*; D001419:Bacteria / Q000187:drug effects; D016166:Free Radical Scavengers / Q000302:isolation & purification; D015394:Molecular Structure; D024301:Plant Bark / Q000737:chemistry; D010936:Plant Extracts / Q000737:chemistry*; D043982:Rhizophoraceae / Q000737:chemistry*; D014315:Triterpenes / Q000302:isolation & purification*
D000893:Anti-Inflammatory Agents; D016166:Free Radical Scavengers; D010936:Plant Extracts; D014315:Triterpenes; C514393:tirucallane
Anopyxis klaineana; Anti-inflammatory; Antioxidant; Limonoids; Rhizophoraceae; Tirucallane triterpenes