Anti-inflammatory tirucallane triterpenoids from Anopyxis klaineana Pierre (Engl.), (Rhizophoraceae)

• Three new tirucallane triterpenes (1–3) were isolated from the stem bark of Anopyxis klaineana.
• Nine known compounds were also isolated.
• The compounds were tested for various activities.
• Compound 1 exhibited remarkable anti-inflammatory activity

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 (HRMSn), 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.

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