<i>Heliopsis longipes</i>: anti-arthritic activity evaluated in a Freund's adjuvant-induced model in rodents

Escobedo-Martínez, Carolina; Guzmán-Gutiérrez, Silvia Laura; Hernández-Méndez, María de los Milagros; Cassani, Julia; Trujillo-Valdivia, Alfonso; Orozco-Castellanos, Luis Manuel; Enríquez, Raúl G.

doi:10.1016/j.bjp.2016.09.003

Carolina Escobedo-Martínez ^** Corresponding author. E-mail:c.escobedo@ugto.mx (C. Escobedo-Martínez).

Departamento de Farmacia, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Guanajuato, Mexico

Silvia Laura Guzmán-Gutiérrez

Catedrática CONACyT, Departamento de Inmunología, Instituto de Investigaciones Biomédicas, Universidad Nacional Autónoma de México, México, DF, Mexico

María de los Milagros Hernández-Méndez

Departamento de Farmacia, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Guanajuato, Mexico

Julia Cassani

Departamento de Sistemas Biológicos, Universidad Autónoma Metropolitana Unidad Xochimilco, México, DF, Mexico

Alfonso Trujillo-Valdivia

Departamento de Farmacia, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Guanajuato, Mexico

Luis Manuel Orozco-Castellanos

Departamento de Farmacia, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Guanajuato, Mexico

Raúl G. Enríquez

Instituto de Química, Universidad Nacional Autónoma de México, México, DF, Mexico

* Corresponding author. E-mail:c.escobedo@ugto.mx (C. Escobedo-Martínez).

Authors' contributions

CEM designed the study, supervised the laboratory and drafted the paper. SLGG analyzed data and contributed to draft the paper. MMHM evaluated the Anti-arthritic activity, running the laboratory work. JC contributed to record NMR spectra. ATV and LMOC contributed to critical reading of the manuscript. RGE contributed to the chromatographic analysis of plant material and the isolation and identification of affinin. All the authors have read the final manuscript and approved the submission.

Conflicts of interest

The authors declare no conflicts of interest.

Proton^a a Data recorded in CDCl3. Chemical shifts (δ) are expressed in ppm with respect to tetramethylsilane (TMS). Coupling patterns are labeled as: d, doublet; dd, doublet of doublets; dt, doublet of triplets; t, triplet; dc, doublet of quartets; m, multiplet. All assignments were based on the following experiments: 1H-1D, 13C-1D, COSY (correlation spectroscopy), HSQC (heteronuclear single quantum coherence; coupling of 1H-13C to a bond), and HMBC (heteronuclear multiple bond correlation; coupling of 1H-13C to 2 and 3 bonds).	Chemical shift	Multiplicity	Area	Coupling constant (Hz)
CH₃-3' and CH₃-4'	0.92	d	6	J = 6.8
CH₃-10	1.77	d	3	J = 7.2
H-2'	1.80	m	1	J = 6.0
CH₂-4 and CH₂-5	2.24, 2.32	dc	4	J = 18.0, 6.0
CH₂-1'	3.13	t	2	J = 6.9
H-6	5.26	dt	1	J = 12.0, 6.0
H-9	5.69	dc	1	J = 13.7, 6.7
H-2	5.86	d	1	J = 15.0
H-7	5.96	t	1	J = 11.0
H-8	6.28	dd broad signal	1	J = 18.0, 12.0
H-3	6.82	dt	1	J = 15.2, 6.7
N-H	6.0	Broad signal	1

Carbon^a a Data recorded in CDCl3. Chemical shifts (δ) are expressed in ppm with respect to tetramethylsilane (TMS). All assignments were based on the following experiments: 1H-1D, 13C-1D, COSY, HSQC, and HMBC.	Chemical shift
C-10	18.30
C-3' and C-4'	20.16
C-5	26.42
C-2'	28.58
C-4	32.12
C-1'	46.91
C-6	124.26
C-8	126.70
C-7	127.63
C-2	129.43
C-3	129.89
C-9	143.36
C-1	166.17

Time (h)	Sample	Dose (mg/kg)	% Inhibition ± SEM
8	Phenylbutazone	80	46.5 ± 6.8^* * Data were analized by ANOVA followed by Tuke's test. p < 0.05.
8	Hl-A	2	18.9 ± 7.5
8	Hl-A	6.6	14.5 ± 8.1
8	Hl-A	20	17.5 ± 8.6
24	Phenylbutazone	80	47.8 ± 5.6*
24	Hl-A	2	42.3 ± 4.2*
24	Hl-A	6.6	29.7 ± 11.3
24	Hl-A	20	31.7 ± 10.3

Time (days)	Sample	Dose (mg/kg)	% Inhibition ± SEM
16	Phenylbutazone	80	23.8 ± 3.0
16	Hl-A	2	25.8 ± 3.0
16	Hl-A	6.6	17.9 ± 6.8
16	Hl-A	20	29.6 ± 5.9
17	Phenylbutazone	80	20.5 ± 0.8
17	Hl-A	2	15.8 ± 2.7
17	Hl-A	6.6	16.8 ± 4.8
17	Hl-A	20	25.2 ± 6.2
18	Phenylbutazone	80	22.4 ± 3.4
18	Hl-A	2	26.0 ± 2.9
18	Hl-A	6.6	13.5 ± 3.5
18	Hl-A	20	30.3 ± 5.3
19	Phenylbutazone	80	20.6 ± 3.2^* * Data were analized by ANOVA followed by Tuke's test. p < 0.05.
19	Hl-A	2	31.9 ± 4.0^* * Data were analized by ANOVA followed by Tuke's test. p < 0.05.
19	Hl-A	6.6	17.39 ± 2.5
19	Hl-A	20	31.1 ± 6.3^* * Data were analized by ANOVA followed by Tuke's test. p < 0.05.
20	Phenylbutazone	80	25.8 ± 3.2
20	Hl-A	2	27.8 ± 5.5
20	Hl-A	6.6	29.9 ± 3.9
20	Hl-A	20	36.8 ± 7.2^* * Data were analized by ANOVA followed by Tuke's test. p < 0.05.
21	Phenylbutazone	80	23.8 ± 4.4
21	Hl-A	2	20.5 ± 2.1
21	Hl-A	6.6	21.0 ± 5.1
21	Hl-A	20	30.9 ± 2.7
22	Phenylbutazone	80	27.41 ± 4.5
22	Hl-A	2	8.6 ± 3.1
22	Hl-A	6.6	19.0 ± 3.4
22	Hl-A	20	27.2 ± 5.4
23	Phenylbutazone	80	27.9 ± 4.6
23	Hl-A	2	21.5 ± 3.4
23	Hl-A	6.6	26.9 ± 3.6
23	Hl-A	20	34.2 ± 4.1^* * Data were analized by ANOVA followed by Tuke's test. p < 0.05.
24	Phenylbutazone	80	25.5 ± 6.1
24	Hl-A	2	19.2 ± 4.9
24	Hl-A	6.6	25.3 ± 4.9
24	Hl-A	20	30.1 ± 3.7
25	Phenylbutazone	80	26.0 ± 5.7^* * Data were analized by ANOVA followed by Tuke's test. p < 0.05.
25	Hl-A	2	18.3 ± 3.8
25	Hl-A	6.6	25.0 ± 3.8
25	Hl-A	20	31.3 ± 3.2^* * Data were analized by ANOVA followed by Tuke's test. p < 0.05.

[1] * Corresponding author. E-mail:c.escobedo@ugto.mx (C. Escobedo-Martínez).

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Heliopsis longipes: anti-arthritic activity evaluated in a Freund's adjuvant-induced model in rodents

ABSTRACT