Cardanols detected in non-polar propolis extracts from Scaptotrigona aff. postica (Hymenoptera, Apidae, Meliponini)

Abstract

The propolis produced by stingless bees of the tribe Meliponini is a viscous product that contains the resin collected from buds, leaves and plant exudates, mixed with salivary secretions, wax and soil. The species Scaptotrigona aff. postica (Latreille, 1807), (Hymenoptera, Apidae, Meliponinae) popularly known as “tubi” in Maranhão State, Brazil, does not mix soil to produce its propolis. The propolis from S. postica harvested in Barra do Corda, Maranhão State, is popularly used in the treatment of wounds and respiratory illnesses. The hydroalcoholic extract of this propolis, rich in flavone-6,8-di-C-glycosides (vicenin-2 and schaftoside), pyrrolizidine alkaloids derived from retronecine, catechin and caffeoylquinic acid derivatives exhibited antiviral activity against the herpes simplex and rubella viruses. The aim of this study was to increase knowledge about the chemical composition of the S. postica propolis by analyzing non-polar extracts obtained using hexane and chloroform as the solvents, by GC-EI-MS. A total of 15 constituents were identified comparing their respective mass spectral data with those available in the NIST data bases and those reported in the literature. The main constituents detected were the phenolic lipids, known as cardanols, 3-(4,7-heptadecadienyl) phenol (5), 3-(10-heptadecenyl) phenol (7), 3-heptadecylphenol (9) and 3-pentadecyl phenol or hydrocardanol (13), which predominated in the hexane extract, while the predominant constituents in the chloroform extract were 3-pentadecyl phenol or hydrocardanol (13) and 3-(8-pentadecenyl) phenol (12). The antioxidant, antitumoral, antifeedant, cytotoxic, anticarcinogenic, antiproliferative, antimicrobial, antileishmanial and larvicidal activities of the cardanols have been demonstrated in many studies.

A highly complex stingless bee propolis: Composition and influence of the period of collection

“…The mass spectra of compound 76 (Figure 1e) and 88 in positive ionization mode, exhibited base peak ion at m/z 111 produced by simple benzylic cleavage, while the resorcinols 72, 82, and 89 exhibited base peak ions at m/z 123, corresponding to the dihydroxytropylium ion also originated by simple benzylic cleavage. 16,[53][54][55]…”

“…postica from Barra do Corda. 16 Mango fruits are suggested as important resin source also for honeybee propolis in tropical habitats. 54 Differences in cycloartane-type triterpenoids may occur in meliponine propolis from distinct tropical regions, which has been attributed to differences in the varieties of mango fruit trees cultivated in one country or locality and another.…”

“…11 Meliponine and honeybee propolis may have similar composition and share the same botanical origin. 8,12 Classes of secondary metabolites reported for meliponine propolis include phenolic acids, hydrolysable tannins, 13 pentacyclic and cycloartane-type triterpenes, 14 diand triterpenic acids, 15 alkylphenols, 16 alkylresorcinols, 17 fatty acids, galloyl glucosides, ellagic acid, acyl-hexosides, acyl-galloyl-hexosides, 18 glycosylated phenolic acids, 19,20 flavonoids, 9,13,21 cinnamoyloxy-mammeisin, 10 steroids and saponins, 22 flavonoids, and phenylpropanoids. 23 Meliponine propolis exert biological activities, such as antioxidant, 24 anti-viral, 5,8,25 antibacterial, 26 anti-protozoal, 27 antiinflammatory, 10 and anticancer.…”

Mangifera indica as propolis source: what exactly do bees collect?

“…Studying propolis, some authors have found the abovementioned cycloartanes (but not any phenolic lipids), and based on these findings they concluded that Mangifera indica L. was the main plant source of the studied samples [ 1 , 8 , 13 , 14 ]. Others have identified only the cardols, no cycloartane acids, and made the same conclusion [ 4 , 15 ]. In these cases, the respective compounds have been isolated, purified and identified by spectral methods.…”

Brown propolis bioactive compounds as a natural antimicrobial in alginate films applied to Piper nigrum L.

“…These are phenols that are unsubstituted at the 4-position (NCBI, 2021c). NEGRI et al (2019), reported this compound among the main constituents identified as unsaturated cardanols, in hexane extract from the Scaptotrigona aff. postica geopropolis.…”