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Chemical Constituents Isolated from Bunchosia Glandulifera

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Chemical Constituents Isolated from Bunchosia Glandulifera Chemical constituents isolated from Bunchosia glandulifera Daiane Einhardt Blank, Sara Silvane de Fraga Silva, Gabriel Jorge Sagrera Darelli, Neusa Fernandes de Moura Universidade Federal de Rio Grande Campus Santo Antônio da Patrulha: Barão do Caí, 125 Cidade Alta [email protected] The fruit of the species Bunchosia glandulifera (Malphiguiaceae) is known as false guarana by the population of Santo Antônio da Patrulha, where the fruit is said to have stimulating and nutritive properties. The pulp of the species is rich in phenolic compounds and carotenoids, whereas its seed is rich in caffeine1. Some studies have shown that B. glandulifera presents antimicrobial activities2. The present work aimed to isolate compounds from the pulp and the seed of the species. To date, 12 compounds have been isolated, but only two of them have had their chemical structures determined. Compound 01 was isolated from the chloroform extract of the seed and was found to be a white precipitate, while compound 02 was isolated from the crude ethanolic extract of the pulp, followed by CC separation. After observing by CCD that the compounds were pure, analyses of 1H NMR and 13C, COSY, HMQC and HMBC were carried out. The 1H NMR spectrum of compound 01 showed the presence of four peaks, related to seven hydrogens. In the 7.28 ppm region, a peak referring to hydrogen bonded to NH; at 5.76 ppm, hydrogen referring to double bonds; and at 3.98 ppm, triplet displaced by the presence of a heteroatom. The analyses also showed triplet at 2.91 ppm referring to two hydrogen. The carbon spectrum confirmed the presence of five carbons, with the presence of carbonyl at 170 ppm, at 120 ppm of the double bonds and at between 31 and 43 ppm two peaks of methylene carbons. The 2D spectra allowed us to confirm the structure 01 as a gamma-lactam. In the analysis of compound 02 we observed in the 1H NMR spectrum the presence of multiplet, with displacement between 4.20 and 4.47 ppm and between 3.35 and 3.62 ppm. The 13C spectrum showed six peaks between 40.55 and 71.75 ppm. By comparing the proton and carbon spectra with the literature it was possible to confirm that compound 02 was mannitol3. 01 02 These substances are being isolated for the first time in the species Bunchosia glandulifera. The gamma-lactam is rarely isolated from natural products and presents, along with its derivatives, anti-bacterial activity4. Mannitol is a type of sugar, used in the food and pharmaceutical industry5. The work of isolating the species is at its early stages, but these results are quite promising because, so far, only phenolic compounds, carotenoids and caffeine have been described in the literature on B. glandulifera. References 1. SILVA, S.F.; BLANK, D.E.; PEIXOTO, C.R.; MOREIRA, J.J.S.; MOURA, N.F. Bioactive Compounds and Antioxidant Activity of Bunchosia glandulífera. Int. J. Food Prop. 19:2, 467- 473, 2016. 2. QUEIROZ, G.S.; HELLER,M.; ARRUDA-SILVA, F.; NASCIMENTO, M.V.P.S.; MICKE, G.A.; DALMARCO, E.M.; PIZZOLATTI, M.G.; BRIGHENTE, I.M.C. Antibacterial and Anti- Inflammatory activities of Bunchosia armeniaca (Cav.) DC. (Malpighiaceae) Rec. Nat. Prod. 3 419-431, 2015. 3. TASKOVA, R.M.; KOKUBUN, T.; RYAN, K.G.; GARNOCK-JONES, P.J.; JENSEN, S.R. Iridoid and phenylethanoid glucosides from veronica lavaudiana. J. Nat. Prod. 74, p. 1477- 1483, 2011. 4. LIMBERGER, J. Carbonilação catalítica de alilaminoálcoois: síntese de hidróxi-gama- lactamas e oxazolidinas bicíclicas, UFRGS, 2006. 5. HELANTO, M.; AARNIKUNNA, J.; VON WEYMARN, N.; AIRAKSINEN, U.; PALVA, A.; LEISOLA, M. Improved mannitol production by a random mutant of Leuconostoc pseudomesenteroides. J. Biotechnol. 116, p. 283-294, 2005. .
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