The chemical composition and antimicrobial activity of propolis from a semi-arid region of Morocco were investigated. Fifteen compounds, including triterpenoids (, , -), macrocyclic diterpenes of ingol type (-) and aromatic derivatives (-), were isolated by various chromatographic methods. Their structures were elucidated by a combination of spectroscopic and chiroptical methods. Compounds and are new natural compounds, and , -, and - are newly isolated from propolis. Moreover, the full nuclear magnetic resonance (NMR) assignments of three of the known compounds (, and ) were reported for the first time. Most of the compounds tested, especially the diterpenes , , and , exhibited very good activity against different strains of bacteria and fungi. Compound 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 spp., and subsp. could be suggested as a probable and new plant source of propolis.
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http://dx.doi.org/10.3390/molecules27072206 | DOI Listing |
Molecules
October 2022
Faculdade de Ciências e Tecnologia, Campus de Gambelas, Universidade do Algarve, 8005-139 Faro, Portugal.
L. is a Moroccan endemic plant known as "Tikiout" and "Daghmus" that can also be found in Mauritania, Western Sahara, and Algeria. In the present review, "", "metabolites" "hemisynthesis" were the keywords used for the research in the Web search engine Google Scholar and in the database Web of Science.
View Article and Find Full Text PDFMolecules
March 2022
Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev Str., Bl. 9, 1113 Sofia, Bulgaria.
The chemical composition and antimicrobial activity of propolis from a semi-arid region of Morocco were investigated. Fifteen compounds, including triterpenoids (, , -), macrocyclic diterpenes of ingol type (-) and aromatic derivatives (-), were isolated by various chromatographic methods. Their structures were elucidated by a combination of spectroscopic and chiroptical methods.
View Article and Find Full Text PDFNat Prod Res
April 2023
School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, China.
Phytochemical investigation on the 95% EtOH extract of the Traditional Chinese Medicine (TCM) (Ba-wang-bian in Chinese) led to the isolation of 11 diterpenoids (-) and two triterpenoids ( and ). Among them, compounds and were new ingenane and ingol diterpenoids, respectively. Their structures were elucidated by a combination of spectroscopic analyses (1 D and 2 D NMR, HRMS, ECD, UV, and IR data) and chemical methods.
View Article and Find Full Text PDFPlanta Med
August 2012
Graduate School of Pharmaceutical Sciences, Chiba University, Chiba, Japan.
In our screening program for natural products that increase death-receptor 5 expression, seven new cycloartane triterpenes, euphonerins A-G (1-7), and 3-O-acetyl-8-O-tigloylingol (8), a new ingol diterpene, were isolated from the MeOH extract of Euphorbia neriifolia leaves, together with 3,12-di-O-acetyl-8-O-tigloylingol (9), (24R)-cycloartane-3β,24,25-triol (10), and three known flavonols (11-13). The structures of 1-8 were elucidated by spectroscopic analysis. Among these compounds, 1-11 showed death-receptor 5 expression enhancing activity.
View Article and Find Full Text PDFBioorg Med Chem
July 2007
Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, Apdo. 40, 11510 Puerto Real, Cádiz, Spain.
Three new, highly functionalized ingol diterpenes, ingol 7,8,12-triacetate 3-phenylacetate (1), ingol 7,8,12-triacetate 3-(4-methoxyphenyl)acetate (2) and 8-methoxyingol 7,12-diacetate 3-phenylacetate (3), together with the novel spirotriterpene, 3S,4S,5R,7S,9R,14R-3,7-dihydroxy-4,14-dimethyl-7[8-->9]-Abeo-cholestan-8-one (4), have been isolated from Euphorbia officinarum latex. Structures were established on the basis of their spectroscopic data, including two-dimensional NMR analysis and NOE experiments. The biological effects of 1-3 on cell cycle and HIV-1 gene transcription were analysed in the Jurkat T cell line.
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