Comparison of Standardized Dichloromethane with Aqueous <i>Pterodon pubescens</i> Benth. Fruit Extracts on Antinociceptive and Anti-Inflammatory Activity

Pterodon pubescens Benth., popularly known as "sucupira", is traditionally used as pain healing agent for many inflammatory diseases. The present study evaluated the in vivo antinociceptive and anti-inflammatory properties of sucupira's fruit dicloromethane extract (Pp) compared to the aqueous extract (Ppa) traditionally used in folk medicine. Extracts' chemical characterization was performed by gas chromatography coupled to mass spectra (GC-MS) detection. The standardized extracts were evaluated using antinociceptive and anti-inflammatory experimental models with mice. The results reported herein allowed establishing a relationship between the popular use of Pterodon pubescens fruit for pain relief and the activity of two major compounds isolated from this species which demonstrated antinociceptive activity. The experimental models corroborate activity of aqueous extract antinociceptive and anti-inflammatory activity, with lower potency compared to dichloromethane extract. Nevertheless the resulting data corroborates sucupira's folk use for pain relief.

Keywords:
Pterodon pubescens Benth.; antinociceptive; furanditerpenes; sucupira; biological and pharmacological activities

Authorship

Rogério Grando

Departamento de Ciências Médicas, Faculdade de Ciências Médicas, Universidade Estadual de Campinas, P.O. Box 611, 13083-970 Campinas-SP, BrazilUniversidade Estadual de CampinasBrazilCampinas, SP, BrazilDepartamento de Ciências Médicas, Faculdade de Ciências Médicas, Universidade Estadual de Campinas, P.O. Box 611, 13083-970 Campinas-SP, Brazil

Vanessa H. Souza

Departamento de Ciências Fisiológicas, Faculdade de Odontologia de Piracicaba, Universidade Estadual de Campinas, P.O. Box 52, 13414-903 Piracicaba-SP, BrazilUniversidade Estadual de CampinasBrazilPiracicaba, SP, BrazilDepartamento de Ciências Fisiológicas, Faculdade de Odontologia de Piracicaba, Universidade Estadual de Campinas, P.O. Box 52, 13414-903 Piracicaba-SP, Brazil

Karin M. Monteiro

Departamento de Clínica Médica, Faculdade de Ciências Médicas, Universidade Estadual de Campinas, P.O. Box 611, 13083-970 Campinas-SP, BrazilUniversidade Estadual de CampinasBrazilCampinas, SP, BrazilDepartamento de Clínica Médica, Faculdade de Ciências Médicas, Universidade Estadual de Campinas, P.O. Box 611, 13083-970 Campinas-SP, Brazil

Ilza M. O. Sousa

Nubia C. A. Queiroz

Faculdade de Ciências Farmacêuticas (FCF), Universidade Estadual de Campinas, P.O. Box 6029, 13083-859 Campinas-SP, BrazilUniversidade Estadual de CampinasBrazilCampinas, SP, BrazilFaculdade de Ciências Farmacêuticas (FCF), Universidade Estadual de Campinas, P.O. Box 6029, 13083-859 Campinas-SP, Brazil

João E. Carvalho

Humberto M. Spindola

Mary A. Foglio ^**e-mail: maryann.foglio@fcf.unicamp.br

*e-mail: maryann.foglio@fcf.unicamp.br

SCIMAGO INSTITUTIONS RANKINGS

Figures

Figures (9)

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Figure 1
Abdominal constrictions induced by acetic acid (0.8% in saline) in mice previously treated (60 min) p.o. with control vehicle (10 mL kg^-1), or Pp and Ppa extracts (10, 30, and 100 mg kg^-1 doses; p.o.). Each column represents the mean ± S.E.M. of up to 6 animals for experimental groups (*p ≤ 0.05, **p ≤ 0.01).

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Figure 2
Graph demonstrating Ppa extract effects on licking induced by formalin in mice. Animals were treated with vehicle, Ppa (30, 100 and 300 mg kg^{-1 doses}; p.o.) prior to formalin. The total time spent licking the hind paw was measured in the first and second phase after intraplantar injection of formalin. Each column represents the mean ± S.E.M. of up to 6 mice in each group (*p ≤ 0.05, **p ≤ 0.01, ***p ≤ 0.001).

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Figure 3
Graph demonstrating Pp extract effects on licking induced by formalin in mice. Animals were treated with vehicle, Pp (30, 100 and 300 mg kg^-1 doses; p.o.) prior to formalin. The total time spent licking the hindpaw was measured in the first and second phase after intraplantar injection of formalin. Each column represents the mean ± S.E.M. of up to 6 mice in each group (*p ≤ 0.05, **p ≤ 0.01, ***p ≤ 0.001).

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Figure 4
Effects of the p.o. treatment 60 min beforehand with Ppa (A) and Pp (B) extracts on the carrageenan-induced paw edema in mice. Results expressed as increased percentage in paw edema compared to the baseline volume, after inflammation induction. Each point represents the mean ± S.E.M. of up to 6 animals. The significance levels (*p ≤ 0.05 and **p ≤ 0.01) were compared with control groups (only vehicle, 10 mL kg^-1).

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Figure 5
Graphs demonstrating results of vocalization or paw withdrawal related to pressure exerted in the right hind paw in response to the hypernociception caused by injection of carrageenan (2.5%, 0.1 mL) in rats p.o. treated with Ppa (A) and Pp (B) 30, 100 and 300 mg kg^{-1 doses} compared to the control group (vehicle). Results expressed as reduction percentage means ± S.E.M. of up to 6 animals for experimental groups compared to the basal values (considered 100%) (*p ≤ 0.05, **p ≤ 0.01).

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Figure 6
Effects of the daily treatments with vehicle (10 mL kg^-1), positive control dexamethasone (10 mg kg^-1), Pp, and Ppa extracts (30, 100, and 300 mg kg^-1) on the CFA-induced arthritis model in rats. Results expressed as arthritis index percentage decreased, compared to the negative control group vehicle. Each point represents the mean ± S.E.M. of up to 6 animals (**p ≤ 0.01 and ***p ≤ 0.001).

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Figure 7
Effects of daily treatments with vehicle (10 mL kg^-1), positive control dexamethasone (10 mg kg^-1), Pp, and Ppa extracts (30, 100, and 300 mg kg^-1 doses) on CFA-induced arthritis rat model. Results expressed as mechanical allodynia pressure (withdrawal threshold in grams), compared to the negative control group vehicle. Each point represents the mean ± S.E.M. of up to 6 animals (*p ≤ 0.05; **p ≤ 0.01; and ***p ≤ 0.001).

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Figure 8
Chemical structure of (1) 6α,7β-dihydroxyvouacapan-17β-oate methyl ester, (2) isomers 6α-hydroxy-7β-acetoxy-vouacapan-17β-oate methyl ester and 6α-acetoxy-7β-hydroxy-vouacapan-17β-oate methyl ester, and (3) acyclic isoprenoid geranylgeraniol.

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Figure 9
GC-MS (HP6890/HP5975) normalized chromatograms of aqueous (A) and dichloromethane (B) extract. Compounds highlighted are geranylgeraniol (m/z 288), 6α,7β-dihydroxyvouacapan-17β-oate methyl ester (m/z 362) and isomers 6α-hydroxy-7β-acetoxy-vouacapan-17β-oate methyl ester (m/z 404 A) and 6α-acetoxy-7β-hydroxy-vouacapan-17β-oate methyl ester (m/z 404 B).

Figure 1 Abdominal constrictions induced by acetic acid (0.8% in saline) in mice previously treated (60 min) p.o. with control vehicle (10 mL kg^-1), or Pp and Ppa extracts (10, 30, and 100 mg kg^-1 doses; p.o.). Each column represents the mean ± S.E.M. of up to 6 animals for experimental groups (*p ≤ 0.05, **p ≤ 0.01).

Figure 2 Graph demonstrating Ppa extract effects on licking induced by formalin in mice. Animals were treated with vehicle, Ppa (30, 100 and 300 mg kg^{-1 doses}; p.o.) prior to formalin. The total time spent licking the hind paw was measured in the first and second phase after intraplantar injection of formalin. Each column represents the mean ± S.E.M. of up to 6 mice in each group (p ≤ 0.05, p ≤ 0.01, p ≤ 0.001).

Figure 3 Graph demonstrating Pp extract effects on licking induced by formalin in mice. Animals were treated with vehicle, Pp (30, 100 and 300 mg kg^-1 doses; p.o.) prior to formalin. The total time spent licking the hindpaw was measured in the first and second phase after intraplantar injection of formalin. Each column represents the mean ± S.E.M. of up to 6 mice in each group (p ≤ 0.05, p ≤ 0.01, p ≤ 0.001).

Figure 4 Effects of the p.o. treatment 60 min beforehand with Ppa (A) and Pp (B) extracts on the carrageenan-induced paw edema in mice. Results expressed as increased percentage in paw edema compared to the baseline volume, after inflammation induction. Each point represents the mean ± S.E.M. of up to 6 animals. The significance levels (*p ≤ 0.05 and **p ≤ 0.01) were compared with control groups (only vehicle, 10 mL kg^-1).

Figure 5 Graphs demonstrating results of vocalization or paw withdrawal related to pressure exerted in the right hind paw in response to the hypernociception caused by injection of carrageenan (2.5%, 0.1 mL) in rats p.o. treated with Ppa (A) and Pp (B) 30, 100 and 300 mg kg^{-1 doses} compared to the control group (vehicle). Results expressed as reduction percentage means ± S.E.M. of up to 6 animals for experimental groups compared to the basal values (considered 100%) (*p ≤ 0.05, **p ≤ 0.01).

Figure 6 Effects of the daily treatments with vehicle (10 mL kg^-1), positive control dexamethasone (10 mg kg^-1), Pp, and Ppa extracts (30, 100, and 300 mg kg^-1) on the CFA-induced arthritis model in rats. Results expressed as arthritis index percentage decreased, compared to the negative control group vehicle. Each point represents the mean ± S.E.M. of up to 6 animals (p ≤ 0.01 and *p ≤ 0.001).

Figure 7 Effects of daily treatments with vehicle (10 mL kg^-1), positive control dexamethasone (10 mg kg^-1), Pp, and Ppa extracts (30, 100, and 300 mg kg^-1 doses) on CFA-induced arthritis rat model. Results expressed as mechanical allodynia pressure (withdrawal threshold in grams), compared to the negative control group vehicle. Each point represents the mean ± S.E.M. of up to 6 animals (p ≤ 0.05; p ≤ 0.01; and p ≤ 0.001).

Figure 8 Chemical structure of (1) 6α,7β-dihydroxyvouacapan-17β-oate methyl ester, (2) isomers 6α-hydroxy-7β-acetoxy-vouacapan-17β-oate methyl ester and 6α-acetoxy-7β-hydroxy-vouacapan-17β-oate methyl ester, and (3) acyclic isoprenoid geranylgeraniol.

Figure 9 GC-MS (HP6890/HP5975) normalized chromatograms of aqueous (A) and dichloromethane (B) extract. Compounds highlighted are geranylgeraniol (m/z 288), 6α,7β-dihydroxyvouacapan-17β-oate methyl ester (m/z 362) and isomers 6α-hydroxy-7β-acetoxy-vouacapan-17β-oate methyl ester (m/z 404 A) and 6α-acetoxy-7β-hydroxy-vouacapan-17β-oate methyl ester (m/z 404 B).

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Comparison of Standardized Dichloromethane with Aqueous <i>Pterodon pubescens</i> Benth. Fruit Extracts on Antinociceptive and Anti-Inflammatory Activity

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[1] *e-mail: maryann.foglio@fcf.unicamp.br