Antiproliferative Constituents of Geopropolis from the Bee Melipona scutellaris

Abstract

Fractionation of geopropolis from Melipona scutellaris, guided by antiproliferative activity against two colon cancer cell lines (COLO205 and KM12), led to the isolation of two new cinnamic acid esters, mammea-type coumarins 5,7-dihydroxy-6-(3-methyl-2-butenyl)-8-(4-cinnamoyl-3-methyl-1-oxobutyl)-4-propyl-coumarin (1) and 5,7-dihydroxy-6-(4-cinnamoyl-3-methyl-1-oxobutyl)-4-phenylcoumarin (2), along with five known coumarins, mammeigin (3), hydroxymammeigin (4), mammeisin (5), cinnamoyloxy-mammeisin (6), and mammein (7), and the prenylated benzophenone ent-nemorosone (8). Among the isolated compounds, 5 and 7 showed the highest cell growth inhibition against COLO205 (GI50 9.7 and 10.7 μM, respectively) and KM12 (GI50 12.0 and 10.9 μM, respectively). The presence of these compounds suggests that plants of Clusiaceae family, especially the genera Kielmeyera and Clusia, are likely to be major sources of geopropolis produced by M. scutellaris.

The Chemical Composition of Brazilian Green Propolis and Its Protective Effects on Mouse Aortic Endothelial Cells against Inflammatory Injury

“…The main plant sources of propolis are Populus spp. ( Salicaceae ) [ 4 ], Baccharis dracunculifolia [ 5 ], Dalbergia ecastaphyllum [ 6 ], Clusia ( Clusiaceae ) [ 7 ] and Azadirachta indica [ 8 ], resulting in the propolis composition being particularly complex. Among these, Baccharis dracunculifolia is the plant source of Brazilian green propolis, which contains isopentenylated phenylpropanoids and their derivatives, caffeoylquinic acids and some terpenes [ 9 , 10 , 11 ].…”

Serial-omics characterization of equine urine

“…[ 63 ]. Mammeigin is another common fruit and vegetable specific neoflavinoid compound and may have antiproliferative activity in some cancer cells [ 64 ]. Buntansin A is a coumerin compound commonly found in plants [ 65 ].…”

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

“…Flavonoids, derivatives of glycosylated phenolic acids and terpenoids were detected in the geopropolis from the stingless bee Melipona orbignyi (Santos et al, 2017b). Prenylated benzophenone and cinnamic acid esters were detected in the geopropolis from Melipona scutellaris Latreille, indicating that a genus of the Clusiaceae family, especially Kielmeyera and Clusia, could be the resin sources of this geopropolis (Cunha et al, 2016). The phenylpropanoids, 6-O-p-coumaroyl-D-galactopyranose and 6-O-cinnamoyl-1-O-p-coumaroylβ -D-glucopyranose, and flavonoids were detected in the geopropolis from Melipona subnitida Ducke (jandaíra), a stingless bee native to northeastern Brazil (Souza et al, 2013(Souza et al, , 2018.…”

“…The geopropolis produced by Melipona fasciculata Smith exhibited antimicrobial activity against Streptococcus mutans and Candida albicans (Liberio et al, 2011). The geopropolis from Melipona scutellaris Latreille exhibited antimicrobial, antioxidant, anti-inflammatory, antinociceptive (Franchin et al, 2012;Silva et al, 2014) and antiproliferative activities (Cunha et al, 2013b(Cunha et al, , 2016. The geopropolis from Melipona orbignyi exhibited antioxidant, anti-inflammatory, antimutagenic and antimicrobial activities (Santos et al, 2017b), while the geopropolis from Melipona mondury exhibited therapeutic potential against inflammatory and oxidative infectious and neoplastic diseases (Santos et al, 2017c).…”