New Δ-tocotrienol derivatives from Colombian propolis

Abstract

Two new δ-tocotrienol derivatives with oxidized terminal chain: 5,6-dioxogarcinoic acid (trans-13'-carboxy-5,6-dioxo-δ-tocotrienol) (2) and 5-hydroxy-8b-oxo garcinoic acid (trans-13'-carboxy-5-hydroxy-8b-oxo-δ-tocotrienol) (3), together with one known derivative garcinoic acid (trans-13'-carboxy-δ-tocotrienol) (1) were isolated from a Colombian propolis. Garcinoic acid was found as a propolis constituent for the first time. The isolated compounds and crude ethanolic extract demonstrated high antimicrobial activity against Staphylococcus aureus and Candida albicans (MICs range: 10-39 μg/ml) as well as promising antioxidant potential in DPPH assay. Compound 3 displayed highest radical scavenging activity, even higher than that of dl-α-tocopherol, used as a positive control.

Propolis: An update on its chemistry and pharmacological applications

“…Colombian Trans-13'-carboxy-5-hydroxy-8b-oxo-δ-tocotrienol, trans-13'-carboxy-5,6-dioxo-δ-tocotrienol, trans-13'-carboxy-δtocotrienol d-Tocotrienol [427] Central Chilean Matorral Prenyletin, trans-3,5-dihydroxy- Chile (E)-3-Hydroxy-1,7-diphenylhept-1-ene-5-acetate, (E)-5-hydroxy-1,7-diphenylhept-1-ene-3-acetate Diarylheptanoid [435] extracts of propolis [7]. The antioxidant activity of a water extract of propolis from Brazil was evaluated using the superoxide scavenging ability assay, the DPPH assay, and the hydroxyl radical scavenging abilit assay.…”

Apoptosis-related gene expression induced by Colombian propolis samples in canine osteosarcoma cell line

“…In Colombia, propolis samples collected in different regions have been chemically characterized, presenting similar components to those found in samples from the Clusia plant, which is native in other tropical countries, such as Cuba and Venezuela [ 10 ]. However, Colombian propolis contains diterpenes and triterpenes, which are still currently poorly known, and components such as eicosyl coumarate and garcinoic acid, which are not observed in other propolis types [ 11 , 12 ]. Propolis may affect both the intrinsic and extrinsic apoptosis pathways [ 13 , 14 ].…”

Chemical analysis, antibacterial, and antioxidant activities of flavonoid‐rich extracts from four Moroccan propolis

“…Indeed, the chemical composition of propolis varies according to the vegetation of the collection site, bee species, and other factors such as the method of extraction and date of collection. More than 1,000 compounds have been identified in propolis worldwide, and nowadays new molecules are being discovered (Anjum et al, 2019;Banzato et al, 2020;Fernández-Calderón et al, 2020;Mahamat et al, 2020;Popova et al, 2020). In recent decades, Brazilian propolis was the most studied.…”