Compostos polifenólicos do kino de Eucalyptus citriodora

Freitas, Marinalva Oliveira; Lima, Mary Anne Sousa; Silveira, Edilberto R.

doi:10.1590/s0100-40422007000800025

Cited by 8 publications

(1 citation statement)

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“…13,14 The isolation of sakuranetin (4), kaempferol 7-methyl ether (5), and aromadendrin 7-methyl ether (7) in both the nest and E. citriodora exudates, clearly evidenced their chemical relationship.…”

Section: -O-cinnamoyl-6-o-(p-coumaroyl)--d-glucopyranoside 7-methylmentioning

confidence: 96%

Flavonoids and triterpenes from the nest of the stingless bee Trigona spinipes

Freitas

Ponte

Lima

et al. 2008

J. Braz. Chem. Soc.

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No nordeste do Brasil, a abelha-sem-ferrão Trigona spinipes perfura o tronco de espécimens cultivados de Eucalyptus citriodora para a produção de exudatos. A investigação química do extrato etanólico do ninho de T. spinipes permitiu o isolamento dos triterpenos cicloartanos ácido magniferólico e ácido 3 -hidroxi-24-metilenocicloartan-26-óico, além dos flavonóides 3'-metilquercetina, sakuranetina, éter 7-metil campferol, tricetina e éter 7-metil aromadendrina como compostos majoritários. O isolamento de sakuranetina, éter 7-metil campferol e éter 7-metil aromadendrina do ninho de T. spinipes e do exudato de Eucalyptus citriodora, sugere esta espécie como origem botânica dos constituintes do ninho destas abelhas-sem-ferrão no nordeste do Brasil. A caracterização estrutural dos compostos isolados foi realizada utilizando-se métodos espectrométricos e comparação com dados da literatura.In the Northeast of Brazil the stingless bee Trigona spinipes Fabricius injures the tree bark of cultivated Eucalyptus citriodora specimens in order to make them exudate. The chemical investigation of the ethanol extract of an entire nest of T. spinipes allowed the isolation of the cycloartane triterpene magniferolic acid and 3 -hydroxy-24-methylenecicloartan-26-oic acid, besides the flavonoids 3'-methyl quercetin, sakuranetin, kaempferol 7-methyl ether, tricetin and aromadendrin 7-methyl ether as the main compounds. The isolation of sakuranetin, kaempferol 7-methyl ether, and aromadendrin 7-methyl ether from both Trigonas spinipes´nest and the exudate from Eucalyptus, may suggest this species as a botanical origin of the nest constituents of these stingless bee in the Northeast of Brazil. The structural characterization of the isolated compounds was accomplished by spectrometric means and comparison with the literature data. Keywords:Trigona spinipes nest, cycloartane triterpenes, flavonoids, Eucalyptus citriodora exudate IntroductionMore than 500 species stingless bees of subfamily Meliponinae are of pantropical distribution, however, the great diversity of species from the tribe Trigonini and all from the trib e Meliponini are found in the Neotropics. Indigenous stingless bee species from South America collect resinous material from plants and mix it with beewax and soil to form "geopropolis" or "divine elixir", terms suggested for the Meliponinae honeys.2,3 In a general way, they build more complex nests than Apis mellifera, although there are a great variety of forms, size and place of construction. The majority of species use closed cavities to build their nests, but some species of the genus Trigona build completely exposed aerial nests with an entrance normally build of wax and mud, and a passage way generally built with geopropolis ending at the storage pots. 4 Until now, chemical reports are concentrated to the honey bee Apis mellifera and only a few information is known about the chemistry of stingless bees, in spite of the estimated number of over 500 Neotropical species. 5Beekeeping of stingless bees or "meliponiculture" ...

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Section: -O-cinnamoyl-6-o-(p-coumaroyl)--d-glucopyranoside 7-methylmentioning

confidence: 96%

Flavonoids and triterpenes from the nest of the stingless bee Trigona spinipes

Freitas

Ponte

Lima

et al. 2008

J. Braz. Chem. Soc.

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Phytochemical, Antiplasmodial, Cytotoxic and Antimicrobial Evaluation of a Southeast Brazilian Brown Propolis Produced by Apis mellifera Bees

Ribeiro

Arruda

Mejía

et al. 2021

Chemistry & Biodiversity

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Seven phenolic compounds (ferulic acid, caffeic acid, 4‐methoxycinnamic acid, 3,4‐dimethoxycinnamic acid, 3‐hydroxy‐4‐methoxybenzaldehyde, 3‐methoxy‐4‐hydroxypropiophenone and 1‐O,2‐O‐digalloyl‐6‐O‐trans‐p‐coumaroyl‐β‐D‐glucopyranoside), a flavanonol (7‐O‐methylaromadendrin), two lignans (pinoresinol and matairesinol) and six diterpenic acids/alcohol (19‐acetoxy‐13‐hydroxyabda‐8(17),14‐diene, totarol, 7‐oxodehydroabietic acid, dehydroabietic acid, communic acid and isopimaric acid) were isolated from the hydroalcoholic extract of a Brazilian Brown Propolis and characterized by NMR spectral data analysis. The volatile fraction of brown propolis was characterized by CG‐MS, composed mainly of monoterpenes and sesquiterpenes, being the major α‐pinene (18.4 %) and β‐pinene (10.3 %). This propolis chemical profile indicates that Pinus spp., Eucalyptus spp. and Araucaria angustifolia might be its primary plants source. The brown propolis displayed significant activity against Plasmodium falciparum D6 and W2 strains with IC50 of 5.3 and 9.7 μg/mL, respectively. The volatile fraction was also active with IC50 of 22.5 and 41.8 μg/mL, respectively. Among the compounds, 1‐O,2‐O‐digalloyl‐6‐O‐trans‐p‐coumaroyl‐β‐D‐glucopyranoside showed IC50 of 3.1 and 1.0 μg/mL against D6 and W2 strains, respectively, while communic acid showed an IC50 of 4.0 μg/mL against W2 strain. Cytotoxicity was determined on four tumor cell lines (SK‐MEL, KB, BT‐549, and SK‐OV‐3) and two normal renal cell lines (LLC‐PK1 and VERO). Matairesinol, 7‐O‐methylaromadendrin, and isopimaric acid showed an IC50 range of 1.8–0.78 μg/mL, 7.3–100 μg/mL, and 17–18 μg/mL, respectively, against the tumor cell lines but they were not cytotoxic against normal cell lines. The crude extract of brown propolis displayed antimicrobial activity against C. neoformans, methicillin‐resistant Staphylococcus aureus, and P. aeruginosa at 29.9 μg/mL, 178.9 μg/mL, and 160.7 μg/mL, respectively. The volatile fraction inhibited the growth of C. neoformans at 53.0 μg/mL. The compounds 3‐hydroxy‐4‐methoxybenzaldehyde, 3‐methoxy‐4‐hydroxypropiophenone and 7‐oxodehydroabietic acid were active against C. neoformans, and caffeic and communic acids were active against methicillin‐resistant Staphylococcus aureus.

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