Phenolic compounds from <i>Virola venosa</i> (Myristicaceae) and evaluation of their antioxidant and enzyme inhibition potential

FERNANDES, Kamila Rangel Primo; BITTERCOURT, Paulo Senna; SOUZA, Afonso Duarte Leão de; SOUZA, Antonia Queiroz Lima de; SILVA, Felipe Moura Araújo da; LIMA, Emerson Silva; ACHO, Leonard Domingo Rosales; NUNOMURA, Rita de Cássia Saraiva; TEIXEIRA, Ana Frazão; KOOLEN, Hector Henrique Ferreira

doi:10.1590/1809-4392201800832

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Chemistry and Pharmacology • Acta Amaz. 49 (1) • Jan-Mar 2019 • https://doi.org/10.1590/1809-4392201800832 linkcopy

Phenolic compounds from Virola venosa (Myristicaceae) and evaluation of their antioxidant and enzyme inhibition potential

Compostos fenólicos de Virola venosa (Myristicaceae) e avaliação de seu potencial antioxidante e de inibição enzimática

Authorship SCIMAGO INSTITUTIONS RANKINGS

ABSTRACT

Virola venosa, popularly known in Brazil as ucuuba-da-mata, occurs naturally in the Amazon region and has potential to provide useful natural compounds, as already known for other Virola species. Therefore, the objective of this study was to determine the chemical composition of bark and leaf extracts of V. venosa, and to test the antioxidant capacity and α-glucosidase inhibition potential of their compounds. Polar extracts showed to be more active in both assays, therefore a bioactivity-guided fractionation was performed to identify the compounds that were responsible for the recorded activities. Using a combination of LC-MS/MS analysis and isolation with NMR identification, eight phenolic compounds were identified. Assays with pure compounds of the active fraction revealed that ferulic acid was the main contributor compound to the observed bioactivity in the crude extracts.

Keywords:
α-glucosidase inhibition; antioxidant compounds; ferulic acid; Amazon

Samples	TPC^a (GAE g^-1)	DPPH^b (%)	DPPH (EC₅₀, µg mL^-1)^c	α-glucosidase^d (%)	α-glucosidase (EC₅₀, µg mL^-1 and mM)^e
HLE	4.28 ± 0.22	na	na	na
HTE	5.36 ± 0.27	na	na	na
ALE	6.14 ± 0.41	na	na	76.1 ± 1.27	50.2 ± 2.47
ATE	4.98 ± 0.29	88.3 ± 1.15	34.7 ± 2.31	98.4 ± 2.04	1.92 ± 0.04
MTE	7.13 ± 0.35	99.4 ± 2.03	13.4 ± 1.12	99.8 ± 2.11	1.64 ± 0.05
MLE	9.74 ± 0.58	87.1 ± 1.88	30.1 ± 1.99	99.9 ± 1.99	1.93 ± 0.09
MTFr.2	22.13 ± 1.55	99.9 ± 1.93	15.1 ± 1.20	79.2 ± 1.45	42.0 ± 2.67
MTFr.3	34.65 ± 1.74	99.3 ± 1.90	18.6± 1.20	96.6 ± 2.00	15.0 ± 1.06
MTFr.4	17.10 ± 1.11	86.7± 1.47	27.1± 1.38	98.5 ± 1.85	12.3 ± 1.31
MLFr.7	41.80 ± 2.09	86. 2 ± 1.99	29.1± 1.27	99.9 ± 2.01	11.0 ± 0.97
Compound 2		nd		na
Compound 4		nd		99.9 ± 1.88	1.63 ± 0.11
Compound 5		nd		na
Compound 6		nd		na
Gallic acid^f		95.6 ± 0.85	3.25 ± 0.25	nd
Acarbose^g		nd		99.9 ± 1.35	6.05 ± 0.06

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Instituto Nacional de Pesquisas da Amazônia Av. André Araujo, 2936 Aleixo, 69060-001 Manaus AM Brasil, Tel.: +55 92 3643-3030, Fax: +55 92 643-3223 - Manaus - AM - Brazil
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[TFN1] ^a
Total phenolic content expressed as gallic acid equivalents (GAE) per gram of crude extract or fraction.

[TFN2] ^b
Antioxidant capacity (AC) expressed in % of inhibition of the 2,2-diphenyl-1-picrylhydrazyl radical (DPPH)

[TFN3] ^c
Antioxidant capacity (AC) expressed as μg mL^-1 (EC₅₀) of crude extract or fraction

[TFN4] ^d
Enzyme inhibition capacity expressed in % of inhibition of α-glucosidase

[TFN5] ^e
Enzyme inhibition capacity expressed as μg mL^-1 (EC₅₀) of crude extract or fraction and as mM for pure compounds

[TFN6] ^f
Positive control for the antioxidant assay.

[TFN7] ^g
Positive control for the enzyme inhibition assay

[TFN8] na = not active; nd = not determined