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Molecules 2018, 23(2), 334; https://doi.org/10.3390/molecules23020334

Mexican Propolis: A Source of Antioxidants and Anti-Inflammatory Compounds, and Isolation of a Novel Chalcone and ε-Caprolactone Derivative

1
Departamento de Inmunología, Catedrática CONACyT-Instituto de Investigaciones Biomédicas, Universidad Nacional Autónoma de México, Ciudad Universitaria, Coyoacán 04510, Ciudad de México, Mexico
2
Departamento de Productos Naturales, Instituto de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, Coyoacán 04510, Ciudad de México, Mexico
3
Departamento de Farmacobiología, CINVESTAV-SUR, Instituto Politécnico Nacional, Calzada de los Tenorios 235, Col. Granjas Coapa C.P. 14330, Ciudad de México, Mexico
4
El Colegio de la Frontera Sur, Ecosur-San Cristóbal, Carretera Panamericana y Periférico Sur s/n Barrio María Auxiliadora, San Cristóbal de Las Casas C.P. 29290, Chiapas, Mexico
5
Catedrático CONACyT—Unidad de Investigación Médica en Epidemiología Clínica, Hospital de Pediatría, Centro Médico Nacional Siglo XXI, Instituto Mexicano del Seguro Social (IMSS). Av. Cuauhtémoc No. 330. Colonia Doctores, Delegación Cuauhtémoc C.P. 06720, Ciudad de México, Mexico
6
Departamento de Inmunología, Instituto de Investigaciones Biomédicas, Universidad Nacional Autónoma de México, Ciudad Universitaria, Coyoacán 04510, Ciudad de México, Mexico
*
Authors to whom correspondence should be addressed.
Received: 19 December 2017 / Revised: 16 January 2018 / Accepted: 16 January 2018 / Published: 6 February 2018
(This article belongs to the Section Natural Products Chemistry)
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Abstract

The propolis produced by bees are used in alternative medicine for treating inflammation, and infections, presumably due to its antioxidant properties. In this context, five propolis from México were investigated to determine their inhibitory lipid peroxidation properties. The ethyl acetate extract from a red propolis from Chiapas State (4-EAEP) was the most potent (IC50 = 1.42 ± 0.07 μg/mL) in the TBARS assay, and selected for further studies. This extract afforded two new compounds, epoxypinocembrin chalcone (6), and an ε-caprolactone derivative (10), as well as pinostrobin (1), izalpinin (2), cinnamic acid (3), pinocembrin (4), kaempherol (5), 3,3-dimethylallyl caffeate in mixture with isopent-3-enyl caffeate (7a + 7b), 3,4-dimethoxycinnamic acid (8), rhamnetin (9) and caffeic acid (11). The HPLC profile, anti-mycobacterial, and antioxidant properties of this extract was also determined. Most of the isolated compounds were also tested by inhibition of reactive oxygen species (ROS) in challenged mouse bone marrow-derived mast cells (BMMCs), and DPPH. Their anti-inflammatory activity was evaluated by TPA, and MPO (myeloperoxidase) activity by ear edema test in mice. The most potent compounds were 7a + 7b in the TBARS assay (IC50 = 0.49 ± 0.06 μM), and 2 which restored the ROS baseline (3.5 μM). Our results indicate that 4-EAEP has anti-oxidant, and anti-inflammatory properties due to its active compounds, suggesting it has anti-allergy and anti-asthma potential. View Full-Text
Keywords: Mexican propolis; red propolis; epoxypinocembrin chalcone; ε-lactone; antioxidant activity; anti-inflammatory activity Mexican propolis; red propolis; epoxypinocembrin chalcone; ε-lactone; antioxidant activity; anti-inflammatory activity
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Guzmán-Gutiérrez, S.L.; Nieto-Camacho, A.; Castillo-Arellano, J.I.; Huerta-Salazar, E.; Hernández-Pasteur, G.; Silva-Miranda, M.; Argüello-Nájera, O.; Sepúlveda-Robles, O.; Espitia, C.I.; Reyes-Chilpa, R. Mexican Propolis: A Source of Antioxidants and Anti-Inflammatory Compounds, and Isolation of a Novel Chalcone and ε-Caprolactone Derivative. Molecules 2018, 23, 334.

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