Antimicrobial Triterpenoids and Ingol Diterpenes from Propolis of Semi-Arid Region of Morocco

Abstract

The chemical composition and antimicrobial activity of propolis from a semi-arid region of Morocco were investigated. Fifteen compounds, including triterpenoids (1, 2, 7–12), macrocyclic diterpenes of ingol type (3–6) and aromatic derivatives (13–15), were isolated by various chromatographic methods. Their structures were elucidated by a combination of spectroscopic and chiroptical methods. Compounds 1 and 3 are new natural compounds, and 2, 4–6, and 9–11 are newly isolated from propolis. Moreover, the full nuclear magnetic resonance (NMR) assignments of three of the known compounds (2, 4 and 5) were reported for the first time. Most of the compounds tested, especially the diterpenes 3, 4, and 6, exhibited very good activity against different strains of bacteria and fungi. Compound 3 showed the strongest activity with minimum inhibitory concentrations (MICs) in the range of 4–64 µg/mL. The combination of isolated triterpenoids and ingol diterpenes was found to be characteristic for Euphorbia spp., and Euphorbia officinarum subsp. echinus could be suggested as a probable and new plant source of propolis.

Antimicrobial Activity of Propolis from the Brazilian Stingless Bees Melipona quadrifasciata anthidioides and Scaptotrigona depilis (Hymenoptera, Apidae, Meliponini)

“…Lipophilic compounds such as terpenes, present in EEP-M and EEP-S, are described in the literature because they present antimicrobial action [ 28 , 29 ].…”

Chemical Composition and Evaluation of Antibacterial, Antibiofilm, and Mutagenic Potentials of a Propolis Sample from the Atlantic Forest of Midwest Brazil

“…This indicates that the combination of compounds 17 and 22 did not provide an additional increment in antibiofilm activity compared to the flavonoid alone. In the case of P. aeruginosa , despite the well‐documented antimicrobial properties of various terpenoids, including a few found in propolis samples, [52,53] the triterpenoids 1 – 14 and 16 , which were found to be a significant group of compounds isolated from the hexane phase, proved inactive at the concentrations tested, whether in pure form or as a mixture (Figure 3 ‐B and D ). It is important to emphasize that several factors should be considered based on the foregoing results.…”

Biological Properties of Latex, Aqueous Extracts and Bee Products of Euphorbia officinarum L.: A Short Review

“…Another beeproduct is propolis, a plant-derived product that bees collect from resins and exudates from diverse parts of the plants, and subsequently transport to the hive, mixing it with beeswax. Bees use propolis to protect the hive against intruders and pathogenic microorganisms [ 72 ]. The detailed chemical composition and antimicrobial activity of propolis from a semi-arid region of Morocco were evaluated by Chimshirova et al [ 72 ].…”

“…Bees use propolis to protect the hive against intruders and pathogenic microorganisms [ 72 ]. The detailed chemical composition and antimicrobial activity of propolis from a semi-arid region of Morocco were evaluated by Chimshirova et al [ 72 ]. Fifteen compounds were isolated and identified, some of them being already reported as constituents of plants in the genus Euphorbia , particularly the macrocyclic diterpenes and triterpenoids, as well as other groups of known compounds (e.g., coumarins, phenolic acids) and new ones (e.g., 29-norlanost-3β-hydroxy-8-ene-7,11-dione).…”