Isolation of diterpenes and flavonoids from a new type of propolis from Saudi Arabia
Graphical abstract
Introduction
Propolis is used in traditional medicine in many countries (Popova et al., 2010). Recently it has become popular as a component of health food and an alternative medicine (da Silva Frozza et al., 1997, Petrova et al., 2010). Honey bees (Apis mellifera) collect exudates from various buds and flora in order to seal the walls of the hive and protect it from micro-organisms (Piccinelli et al., 2011). Propolis composition varies according to geographic region (Bertelli et al., 2012, Salatino et al., 2011, Watson et al., 2006). Propolis has antimicrobial, antimycotic, anti-inflammatory, antioxidant, antitumor, anti-neurodegenerative, antituberculosis, antiviral, cytotoxic, anti-inflammatory, and immunomodulatory activities (Falcao et al., 2010, Yildirim et al., 2004). It contains many chemical constituents and to date more than 300 compounds have been identified as constituents including polyphenols, flavanones, flavonols, flavones, dihydroflavonols, chalcones, phenolic acids and their esters, monoterpenes, sesquiterpenes, diterpenes and triterpenes, steroids, aromatic aldehydes, alcohols, naphthalene and stilbene derivatives (Abu-Mellal et al., 2012, da Silva Frozza et al., 1997). This study reports the characterisation of a new type of propolis from Saudi Arabia and its activity on Trypanosoma brucei brucei the causative organism of African sleeping sickness. A new diterpene propsiadin ((ent)-2-oxo-kaur-16-en-6,18-diol) (3) along with the flavonoids 3,4-dihydro-2-(3,4-dihydroxyphenyl)-2H-chromene-3,7-diol (1), psiadiarabin (2) and the diterpene psiadin (4). The likely sources of the propolis are Psiadia arabica and Psiadia punctulata and it represents a new type of propolis not described before.
Section snippets
Results and discussion
The isolated compounds (Fig. 1) were obtained from an ethanol extract of the Saudi Arabian propolis. Compounds 3 and 4 were obtained by column chromatography followed by medium pressure flash chromatography on silica gel. The elemental compositions for the compounds were obtained from LC–MS analysis using an Orbitrap mass spectrometer. The structures were identified by 1D and 2D NMR analysis as summarised in Table 1, Table 2.
Compound 1 gave a molecular ion [M+H]+ at m/z 275.0910 HR-ESIMS
General methods
Optical rotation: optical rotations were measured on a Perkin–Elmer 431 polarimeter at 20 °C.
The NMR spectra [1H and 13C NMR, DEPT 135; 2D H, H-COSY, heteronuclear single quantum correlation (HSQC, HMBC, NOESY)] were obtained using Bruker Avance 600 and JEOL-LA 400 FT-NMR spectrometer systems with CDCl3 and d6-DMSO as solvents and referencing to the signal for the residual protons. Chemical shifts are given in ppm, and coupling constants are in Hz. MestReNova 8.1.2 was used for processing the
Acknowledgement
S. Almutairi is grateful to the Saudi government for a Ph.D. scholarship.
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Experimental study and modeling on supercritical CO<inf>2</inf> extraction of Indonesian raw propolis using response surface method: Influence of pressure, temperature and CO<inf>2</inf> mass flowrate on extraction yield
2020, Chemical Engineering Research and DesignCitation Excerpt :Mediterranean raw propolis is rich with terpenes such as isocupressic acid, pimaric, imbricatoloic acid, agathadiol, totarol, 13-epi-torulosal, communic acid, 13-epi-cupressic acid, abietic acid and ferruginolon (Graikou et al., 2016). Saudi Arabian raw propolis is also rich with diterpenes such as diterpene propsiadin and diterpene psiadin (Almutairi et al., 2014). These differences can be definitely caused by the origin of propolis, the season when the propolis is collected, the kind of bee species and the feed of bee.
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2018, PhytochemistryCitation Excerpt :This information along with the 13C NMR data, which sorted 20 carbons into two methyls; eight methylenes, one of which had an sp2 carbon; three methines; four quaternary carbons, one of which was an sp2 carbon; two hydroxymethines; and one hydroxymethylene, led to the determination of five indices of hydrogen deficiency and a ent-kaurane nucleus for 3. The 1H and 13C NMR data (Table 1) were quite similar to those reported for ent-kaur-16(17)-en-6,19-dihydroxy-2-one (14) (Almutairi et al., 2014); the point of difference was the chemical shift of protons and carbons of ring A. The structure of 3 differed from propsiadin at C-2, where the oxo group was replaced by an oxymethine group (δC 64.3; δH 3.83).
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2018, PhytochemistryChemical compositions and characteristics of organic compounds in propolis from Yemen
2017, Saudi Journal of Biological SciencesCitation Excerpt :The typical bulk composition of propolis is vegetation resin and balsam (gum) (50%), wax (30%), essential and aromatic oils (10%), pollen (5%) and other substances (5%) (Cirasino et al., 1987; Monti et al., 1983). The majority of the chemical compositions and bio-activity effects of propolis were described for samples from Europe and Latin America (e.g. Bankova et al., 1992, 2000; Daugsch et al., 2008; Barros et al., 2007; Monti et al., 1983; Márquez Hernández et al., 2010), whereas few studies have been reported on propolis from the Arabian Peninsula (Abd El-Mawla and Osman, 2011; Almutairi et al., 2014; Fahmi et al., 2001; Jerz et al., 2014; Popova et al., 2013; Alqarni et al., 2015), with none from Yemen. Yemen is located in south of the Arabian Peninsula with different climatic and physiographic conditions that endow the country with about 3700 species belonging to 140 families of plants (Alhammadi, 2010).
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