Composition, Antioxidant and Anti-inflammatory activities of Hexane and Methanol extracts of <i>Acmella uliginosa</i> from Terai region of Uttarakhand

Gairola, Kanchan; Gururani, Shriya; Kumar, Ravendra; Prakash, Om; Agrawal, Sanjeev; Dubey, Shiv Kumar

doi:10.1590/s2175-97902022e20353

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Brazilian Journal of Pharmaceutical Sciences

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Article • Braz. J. Pharm. Sci. 58 • 2022 • https://doi.org/10.1590/s2175-97902022e20353 copy

Composition, Antioxidant and Anti-inflammatory activities of Hexane and Methanol extracts of Acmella uliginosa from Terai region of Uttarakhand

Authorship SCIMAGO INSTITUTIONS RANKINGS

Abstract

Acmella uliginosa, an edible herb belonging to Asteraceae family, was collected from the Terai region of Uttarakhand, India. Methanol and hexane extracts of the whole plant were prepared using soxhlet apparatus. The GC-MS analysis of plant extracts identifies 22 and 35 major compounds of methanol and hexane extracts which comprises of 74.21% and 73.20% of the total composition of extracts, respectively. The major compound in hexane was 2, 4-heptadienal (7.99%) whereas trans, trans-9, 12-octadecadienoic acid propyl ester (16.96%) was major compound in methanol extract. The extracts were evaluated for antioxidant and anti-inflammatory properties. Methanol extract showed higher free radical scavenging and reducing power activities with IC₅₀ value 153.82±1.69 μg/mL and RP₅₀ value of 152.28±0.41 μg/mL, respectively. The metal chelating activity was higher in hexane extract as compared to methanol extract i.e., 62.08±0.25 μg/mL. The anti-inflammatory activity assessed by its ability to inhibit denaturation was higher in methanol having IB₅₀ value 87.33±0.15 µg/mL. The total phenolic content (TPC), total flavonoid content (TFC) and ortho-dihydric phenol content (ODP) of methanol and hexane extracts were also evaluated. TPC, TFC and ODP was higher in methanol extract having value of 122.23±0.22, 35.01±0.29 and 8±0.86 mg/mL, respectively. Acmella uliginosa, might be considered as a natural source for antioxidant and anti-inflammatory properties.

Keywords:
Acmella uliginosa; Hexane extract; Methanol extract; Antioxidant activity; Anti- inflammatory activity

S. No.	Chemical compounds	Chemical formula	R. time	% Area	Method of identification
1.	1-pentadecanol	C₁₅H₃₂O	14.15	3.35	M+: - 228
1.	1-pentadecanol	C₁₅H₃₂O	14.15	3.35	M/Z: - 55,83,97,41
2.	β-sesquiphellandrene	C₁₅H₂₄	14.63	2.42	M+: - 204
2.	β-sesquiphellandrene	C₁₅H₂₄	14.63	2.42	M/Z -69,41,93,120
3.	l-(+)-ascorbic acid 2,6-dihexadecanoate	C₃₈H₆₈O₈	19.49	1.49	M+: - 652
3.	l-(+)-ascorbic acid 2,6-dihexadecanoate	C₃₈H₆₈O₈	19.49	1.49	M/Z- 57,73,43,41,129
4.	linoleic acid, methyl ester	C₁₉H₃₄O₂	20.66	1.18	M+: -294
4.	linoleic acid, methyl ester	C₁₉H₃₄O₂	20.66	1.18	M/Z- 67, 81,55,41
5.	phytol isomer	C₂₀H₄₀O	20.83	4.60	M+: - 296
5.	phytol isomer	C₂₀H₄₀O	20.83	4.60	M/Z-71,57,43,41
6	2,4-heptadienal	C₇H₁₀O	21.73	7.99	M+: - 110
6	2,4-heptadienal	C₇H₁₀O	21.73	7.99	M/Z- 81,41,53,67
7	2,4-heptadienal, (E ,E)	C₇H₁₀O	21.90	2.84	M+: - 110
7	2,4-heptadienal, (E ,E)	C₇H₁₀O	21.90	2.84	M/Z- 81,53,41,
8	(2E,6Z,8E)-N-(2-Phenylethyl)-2,6,8-decatrienamide	C₁₈H₂₃NO	22.63	1.51	M+: -269
8	(2E,6Z,8E)-N-(2-Phenylethyl)-2,6,8-decatrienamide	C₁₈H₂₃NO	22.63	1.51	M/Z- 81,68,53,40
9	tetracontane	C₄₀H₈₂	24.14	2.73	M+: - 562
9	tetracontane	C₄₀H₈₂	24.14	2.73	M/Z- 57,71,43,99
10	cachalot O-8	C₁₈H₃₆O	25.50	1.07	M+- 268 M/Z- 55,82,67,41
11	oleyl alcohol	C₁₈H₃₆O	25.71	6.82	M+- 268
11	oleyl alcohol	C₁₈H₃₆O	25.71	6.82	M/Z- 55,67,82,41
12	squalene	C₃₀H₅₀	26.76	2.55	M+- 410
12	squalene	C₃₀H₅₀	26.76	2.55	M/Z- 69,81,95,41
13	tetracontane	C₄₀H₈₂	27.68	2.42	M+: - 562
13	tetracontane	C₄₀H₈₂	27.68	2.42	M/Z- 57,71,85,43
14	tetrapentacontane	C₅₄H₁₁₀	30.53	3.32	M+: - 758
14	tetrapentacontane	C₅₄H₁₁₀	30.53	3.32	M/Z: - 57,71,85,43
15	γ-tocopherol	C₂₉H₅₀O₂	31.09	1.68	M+: - 430
15	γ-tocopherol	C₂₉H₅₀O₂	31.09	1.68	M/Z- 165,430,205
16	24-epicampesterol	C₂₈H₄₈O	33.12	1.24	M+: - 400
16	24-epicampesterol	C₂₈H₄₈O	33.12	1.24	M/Z: - 43,5741,213
17.	β- sitosterol	C₂₉H₅₀O	35.25	7.75	M+: - 414
17.	β- sitosterol	C₂₉H₅₀O	35.25	7.75	M/Z: - 43,41,57
18.	olean-12-en-3-one	C₃₀H₄₈O	36.23	1.93	M+: - 424
18.	olean-12-en-3-one	C₃₀H₄₈O	36.23	1.93	M/Z: - 218, 203,189,175
19.	24-norursa-3,12-diene	C₂₉H₄₆	37.56	2.56	M+: - 394
19.	24-norursa-3,12-diene	C₂₉H₄₆	37.56	2.56	M/Z: - 218,203, 161,
20	hex-3-en-2-one	C₆H₁₀O	6.095	0.98	M+: - 98
20	hex-3-en-2-one	C₆H₁₀O	6.095	0.98	M/Z: - 83,55,98,29
21	cis-9-tetradecen-1-ol	C₁₄H₂₈O	13.91	0.92	M+: - 212
21	cis-9-tetradecen-1-ol	C₁₄H₂₈O	13.91	0.92	M/Z: - 67,55,81,41
22	3,7,11-trim ethyl-2,6,10-dodecatrien -1-ol	C₁₅H₂₆O	14.41	0.57	M+: - 222
22	3,7,11-trim ethyl-2,6,10-dodecatrien -1-ol	C₁₅H₂₆O	14.41	0.57	M/Z: - 69,93,41,119
23	dihydro-aplotaxene	C₁₇H₃₀	16.21	0.81	M+: - 234
23	dihydro-aplotaxene	C₁₇H₃₀	16.21	0.81	M/Z: - 67,81,55.95
24	perhydrofarnesyl acetone	C₁₈H₃₆O	18.17	0.90	M+: - 268
24	perhydrofarnesyl acetone	C₁₈H₃₆O	18.17	0.90	M/Z: -58,43,71,85
25	1,1":1',1"'-bivanadocenium (2+), bis[hexafluorophosphate (1-)]	C₂₀H₁₆V₂	20.37	0.61	M+: - 358
25		C₂₀H₁₆V₂	20.37	0.61	M/Z: - 128,57,77
26	α.-glyceryl linolenate	C₂₁H₃₆O₄	20.71	0.51	M+: - 352
26	α.-glyceryl linolenate	C₂₁H₃₆O₄	20.71	0.51	M/Z: - 79,67,95
27	cyclopropane, 1-bromo-1-(3-methyl-1-pentenylidene)-2,2,3,3-tetramethyl-	C₁₃H₂₁Br	21.14	0.62	M+: - 256
27		C₁₃H₂₁Br	21.14	0.62	M/Z: - 57,55105
28	14-methyl-8-hexadecyn-1-ol	C₁₇H₃₂O	21.27	0.61	M+: - 252
28	14-methyl-8-hexadecyn-1-ol	C₁₇H₃₂O	21.27	0.61	M/Z: - 81,67,55,41
29	2-heptylfuran	C₁₁H₁₈O	21.78	0.73	M+: - 166
29	2-heptylfuran	C₁₁H₁₈O	21.78	0.73	M/Z: - 81, 53,109
30	heneicosane	C₂₂H₄₄	22.50	0.86	M+: - 296
30	heneicosane	C₂₂H₄₄	22.50	0.86	M/Z: - 57,71, 43,85
31	glycerol, 2-palmitate	C₁₉H₃₈O₄	24.28	0.94	M+: - 330
31	glycerol, 2-palmitate	C₁₉H₃₈O₄	24.28	0.94	M/Z: - 98,112,74,84
32	tetracontane	C₄₀H₈₂	26.61	0.51	M+: - 562
32	tetracontane	C₄₀H₈₂	26.61	0.51	M/Z: - 57,71, 85, 43
33	tetracontane	C₄₀H₈₂	28.95	0.90	M+: - 562
33	tetracontane	C₄₀H₈₂	28.95	0.90	M/Z: - 57,71, 85, 43
34	tetracontane	C₄₀H₈₂	34.86	0.87	M+: - 562
34	tetracontane	C₄₀H₈₂	34.86	0.87	M/Z: - 57,71, 85, 43
35	methyl commate D	C₃₁H₅₄O₄	36.68	0.61	M+: - 486
35	methyl commate D	C₃₁H₅₄O₄	36.68	0.61	M/Z: - 218, 203,189, 133
	Total			73.2%

S. No.	Chemical compounds	Molecular formula	Retention time	% Area	Method of identification
1.	(Z)-3-hexadecene	C₁₆H₃₂	14.155	1.10	M+: - 224
1.	(Z)-3-hexadecene	C₁₆H₃₂	14.155	1.10	M/Z: - 69, 55,41
2.	pentadecanoic acid, methyl ester	C₁₆H₃₂O₂	19.01	1.24	M+: -256
2.	pentadecanoic acid, methyl ester	C₁₆H₃₂O₂	19.01	1.24	M/Z: - 87,74,57, 41
3.	octadecanoic acid	C₁₈H₃₆O₂	19.470	6.22	M+: -284
3.	octadecanoic acid	C₁₈H₃₆O₂	19.470	6.22	M/Z: - 73,60,41,43
4.	9,12-octadecadienoic	C₁₉H₃₄O₂	20.657	3.34	M+: -294
4.	9,12-octadecadienoic	C₁₉H₃₄O₂	20.657	3.34	M/Z: - 81,67,41,55
5.	methyl 11,14,17-eicosatrienoate	C₂₁H₃₆O₂	20.714	1.59	M+: - 320
5.	methyl 11,14,17-eicosatrienoate	C₂₁H₃₆O₂	20.714	1.59	M/Z: - 79, 67,108,55
6.	2-hexadecen -1-ol, 3,7,11,15-tetramethyl -, (2E,7R,11R)-	C₂₀H₄₀O	20.822	4.42	M+: -296
6.	2-hexadecen -1-ol, 3,7,11,15-tetramethyl -, (2E,7R,11R)-	C₂₀H₄₀O	20.822	4.42	M/Z: - 71,57,43,95
7.	1-tetradecyne	C₁₄H₂₆	21.125	1.71	M+: -194
7.	1-tetradecyne	C₁₄H₂₆	21.125	1.71	M/Z: - 81, 67,41
8.	2,4-heptadienal, (E,E)	C₇H₁₀O	21.66	10.38	M+: - 110
8.	2,4-heptadienal, (E,E)	C₇H₁₀O	21.66	10.38	M/Z: - 81, 67, 41,53
9.	5,8,11eicosatriynoic acid, methyl ester	C₂₁H₃₀O₂	22.23	2.82	M+: - 314
9.	5,8,11eicosatriynoic acid, methyl ester	C₂₁H₃₀O₂	22.23	2.82	M/Z: - 129, 91, 41
10.	N-(2-methylbutyl) (2E,4E,8Z,10E)-dodecatetraenamide	C₁₇H₂₇NO	22.60	2.50	M+: - 261
10.	N-(2-methylbutyl) (2E,4E,8Z,10E)-dodecatetraenamide	C₁₇H₂₇NO	22.60	2.50	M/Z: - 81,41,95
11.	stearic acid 1-monoglyceride	C₂₁H₄₂O₄	24.27	3.77	M+: - 358
11.	stearic acid 1-monoglyceride	C₂₁H₄₂O₄	24.27	3.77	M/Z: - 98,84,74, 57
12.	bis(2-ethylhexyl) phthalate	C₂₄H₃₈O₄	24.413	3.45	M+: -390
12.	bis(2-ethylhexyl) phthalate	C₂₄H₃₈O₄	24.413	3.45	M/Z: - 149,167,57,43
13.	trans, trans-9,12-octadecadienoic acid, propyl ester	C₂₁H₃₈O₂	25.702	16.96	M+: -322
13.	trans, trans-9,12-octadecadienoic acid, propyl ester	C₂₁H₃₈O₂	25.702	16.96	M/Z: - 81,67,95,55
14.	stigmast-5-en-3-ol, (3β)	C₂₉H₅₀O	35.154	5.68	M+: - 414
14.	stigmast-5-en-3-ol, (3β)	C₂₉H₅₀O	35.154	5.68	M/Z: -43,81,95,41
15.	methyl commate c	C₃₁H₅₀O₄	36.190	1.35	M+: -486
15.	methyl commate c	C₃₁H₅₀O₄	36.190	1.35	M/Z: -218,203,189,175
16.	24-norursa-3,12-diene	C₂₉H₄₆	37.505	2.28	M+: - 394
16.	24-norursa-3,12-diene	C₂₉H₄₆	37.505	2.28	M/Z: - 218,203,55,41
17.	γ.-tocopherol, methyl ether	C₂₉H₅₀O₂	38.923	1.69	M+: - 430
17.	γ.-tocopherol, methyl ether	C₂₉H₅₀O₂	38.923	1.69	M/Z: - 165,43,151,57
18	sesquisabinene isomer	C₁₅H₂₄	14.629	0.72	M+: - 204
18	sesquisabinene isomer	C₁₅H₂₄	14.629	0.72	M/Z: - 69, 77,55,41
19	perhydrofarnesyl acetone	C₁₈H₃₆O	18.169	0.71	M+: - 268
19	perhydrofarnesyl acetone	C₁₈H₃₆O	18.169	0.71	M/Z: - 58,43,71,41
20	(5-methylhepta-1,3-dienyl) benzene	C₁₄H₁₈	20.368	0.88	M+: - 186
20	(5-methylhepta-1,3-dienyl) benzene	C₁₄H₁₈	20.368	0.88	M/Z: - 129,115,91,77
21	4-butylbenzoic acid	C₁₅H₂₃NO₂	23.836	0.55	M+: - 249
21	4-butylbenzoic acid	C₁₅H₂₃NO₂	23.836	0.55	M/Z: - 58,71,91,103
22	δ- 5-24-isoergosten -3β-ol (campesterol )	C₂₈H₄₈O	33.092	0.85	M+: - 400
22	δ- 5-24-isoergosten -3β-ol (campesterol )	C₂₈H₄₈O	33.092	0.85	M/Z: - 213,107,159,145
	Total			74.21%

S. No.	Samples	IC₅₀ values in triplicate			Mean IC₅₀ values (µg/mL)
S. No.	Samples	1^st	2^nd	3^rd	Mean IC₅₀ values (µg/mL)
1.	AUME	153.72	153.13	153.56	153.82±1.69 µg/mL
2.	AUHE	204.83	204.28	204.06	204.37±0.41 µg/mL
3.	AA	51.11	51.99	51.58	51.56±0.44 µg/mL

S. No.	Sample Name	IC₅₀ values (µg/mL) in triplicate			Mean IC₅₀ values with standard deviation (µg/mL)
S. No.	Sample Name	1^st	2^nd	3^rd	Mean IC₅₀ values with standard deviation (µg/mL)
1.	AUME	83.02	83.13	83.62	83.26± 0.07
2.	AUHE	61.65	62.01	62.58	62.08±0.25
3.	EDTA	45.39	45.32	46.51	45.74±0.67

S. No.	Sample Name	RP₅₀ values (µg/mL) in triplicate			Mean RP₅₀ values (µg/mL)
S. No.	Sample Name	1^st	2^nd	3^rd	Mean RP₅₀ values (µg/mL)
1.	AUME	152.31	151.85	152.69	152.28 ±0.41 µg/mL
2.	AUHE	156.16	157.33	161.77	158.42 ± 2.96 µg/mL
3.	Gallic acid	78.37	79.77	81.56	79.90 ± 1.60 µg/mL

Plant extracts	IC₅₀ of various antioxidant activities
Plant extracts	DPPH radical scavenging activity	Metal chelating activity of Fe⁺²	Reducing power activity of Fe⁺³	TPC (Total Phenolics Content)
AUME	153.82±5.34	83.26±0.07	152.28±0.41	122.23±0.22 mg/gm GAE
AUHE	204.37±0.41	62.08±0.25	158.42±2.96	83.66±0.33 mg/gm GAE

Parameter	DPPH radical scavenging activity	Metal chelating activity of Fe²⁺	Reducing power of Fe³⁺
TPC (Total phenolic content)	-0.99959	0.999307	-0.90292

S. No.	Sample Name	IB₅₀ values in triplicate			Mean IC₅₀ values
S. No.	Sample Name	1^st	2^nd	3^rd	Mean IC₅₀ values
1.	AUME	87.24	87.24	87.51	87.33± 0.154 µg/mL
2.	AUHE	140.30	138.33	139.68	139.44± 1.012 µg/mL
3.	Diclofenac sodium	22.74	22.12	22.88	22.58±0.404 µg/mL

Universidade de São Paulo, Faculdade de Ciências Farmacêuticas Av. Prof. Lineu Prestes, n. 580, 05508-000 S. Paulo/SP Brasil, Tel.: (55 11) 3091-3824 - São Paulo - SP - Brazil
E-mail: bjps@usp.br

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[1] *Correspondence: S. K. Dubey. Department of Biochemistry. C.B.S.H..G. B. Pant University of Agriculture and Technology. Pantnagar-263145, Uttarakhand, India. Email: shivdub@gmail.com.