Chemical Profile and Cytotoxic Activity of Leaf Extracts from Senna spp. from Northeast of Brazil

Silva, Juliana G. A.; Silva, Alexander A.; Coutinho, Isabel D.; Pessoa, Claudia O.; Cavalheiro, Alberto J.; Silva, Maria G. V.

doi:10.5935/0103-5053.20160073

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Articles • J. Braz. Chem. Soc. 27 (10) • Oct 2016 • https://doi.org/10.5935/0103-5053.20160073 copy

Chemical Profile and Cytotoxic Activity of Leaf Extracts from Senna spp. from Northeast of Brazil

Authorship SCIMAGO INSTITUTIONS RANKINGS

Methanolic, diethyl ether and n-hexane extracts of leaves of four species of Senna (S. gardneri, S. macranthera, S. splendida and S. trachypus) were analyzed by gas chromatography coupled to mass spectrometry (GC-MS). Using linear retention indices and mass spectral data, 34 compounds were identified, including fatty acids, flavonoids, terpenoids and steroids that were not reported previously for these species. Additionally, the cytotoxicity of the extracts against different tumor cell lines was determined. The cytotoxicity was then correlated with the chemical composition of the extracts by partial least squares-discriminant analysis (PLS-DA). The n-hexane extract of S. gardneri and the ethyl ether extract of S. splendida were the most active against human colon (59.75 and 31.37%, respectively) and human glioblastoma (52.85 and 48.28%, respectively) cell lines.

Keywords:
Senna spp.; GC-MS; dereplication; cytotoxicity; multivariate analysis

Compound	Rt^a a Rt = retention time; bRIexp = experimental retention index; / min	RI_exp^b b RIexp = experimental retention index;	RI_lit^c c RIlit = retention index from literature;	MS^d d similarity based on NIST MS database; / %	Compound name	Representative ions (m/z)^e e representative ions in decreasing order of abundance;	Senna spp. extract^f f Sennassp.: SgH = S. gardneri hexane, SgE = S. gardneri ether, SgM = S. gardneri methanol, SmH = S. macranthera hexane, SmE = Senna macranthera ether, SmM = S. macranthera methanol, SsH = S. splendida hexane, SsE = S. splendida ether, SsM = S. splendidamethanol, StH = S. trachypus hexane, StE = S. trachypus ether, StM = S. trachypus methanol;
1	6.080	1301	1289	97	succinic acid^* * compounds identified as TMS derivatives.	147 (BP)^g g BP = base peak; , 73, 247	SgM, StM, SsE, SsM, SmM
2	6.268	1314	1336	91	glyceric acid^* * compounds identified as TMS derivatives.	73 (BP), 147, 189, 103, 292	SgM, SsM
3	8.615	1397	1404	92	pentanedioic acid^* * compounds identified as TMS derivatives.	147 (BP), 73, 261, 158	SsE
4	8.989	1420	1420	93	b-caryophyllene	69 (BP), 93, 133, 79, 91	SgM, SmM
5	10.980	1482	1499	96	malic acid^* * compounds identified as TMS derivatives.	73 (BP), 147, 233	SgM, SmH, SmM
6	11.731	1511	1521	96	pyroglutamic acid^* * compounds identified as TMS derivatives.	156 (BP), 73, 147	SgM, SmM, SsM
7	14.946	1600	1613	82	3-hydroxy-3-methylglutaric acid^* * compounds identified as TMS derivatives.	73 (BP), 103, 147, 219, 247	SsE, SgE
8	21.879	1815	1828	90	benzoic acid, 3,4-dihydroxy^* * compounds identified as TMS derivatives.	73 (BP), 193, 370, 355, 311	SgM
9	21.987	1818	1838	92	citric acid^* * compounds identified as TMS derivatives.	73 (BP), 193, 370, 355, 311	SgM
10	22.788	1837	1837	94	neophytadiene	66 (BP), 95, 82, 57, 123, 278 [M^+•]^h h [M+.] = molecular ion;	SgE, SgM, StE, StM
11	27.789	1990	1992	91	galactonic acid^* * compounds identified as TMS derivatives.	73 (BP), 147, 292, 319, 217	SsE, SsM, StM
12	27.963	1994	1997	92	gluconic acid^* * compounds identified as TMS derivatives.	73 (BP), 147, 333, 292, 217	SgH, SgM, SsH, SsE, StH, StM
13	29.571	2046	2047	97	hexadecanoic acid^* * compounds identified as TMS derivatives.	117 (BP), 73, 313, 132,145, 328 [M^+•]	SgH, SgE, SgM, SmH, SmE, SmM, SsH, SsM, SsE, StE, StM
14	31.199	2094	2092	93	linolenic acid methyl ester	79 (BP), 67, 95, 93, 108	SsH, SgH
15	33.242	2162	2164	93	linolenic acid ethyl ester	79 (BP), 67, 95, 93, 108	StE
16	33.393	2172	2183	94	phytol^* * compounds identified as TMS derivatives.	143 (BP), 73, 75, 123	SgH, SmH, SsH, SsE, SsM, StH, StM
17	34.403	2207	2212	97	linoleic acid^* * compounds identified as TMS derivatives.	73 (BP), 75, 81, 337, 95, 352 [M^+•]	SgH, SgE, SgM, SmH, SmE, SsH, SsE, SsM, StH, StE, StM
18	34.574	2212	2218	96	a-linolenic acid^* * compounds identified as TMS derivatives.	75 (BP), 73, 95, 108, 129, 335, 350 [M^+•]	SgH, SgE, SgM, SmH, SmE, SsH, SsE, SsM, StH, StE, StM
19	35.459	2243	2248	96	stearic acid^* * compounds identified as TMS derivatives.	117 (BP), 73, 341, 132, 129, 356 [M^+•]	SgH, SgE, SgM, SmH, SmE, SsH, SsE, SsM, StH, StE, StM
20	40.831	2441	2447	92	eicosanoic acid^* * compounds identified as TMS derivatives.	117 (BP), 73, 369, 132, 145, 384 (M^.+)	SgH, SmH, StH, StM
21	45.898	2639	2638	92	docosanoic acid^* * compounds identified as TMS derivatives.	117 (BP), 73, 397, 132, 145, 412 [M^+•]	SgH, SmH, SsH, StM
22	46.710	2663	2705	73	chrysin^* * compounds identified as TMS derivatives. or isomer	383 (BP), 384, 73	SmE
23	49.998	2807	2812	98	squalene	69 (BP), 81, 121, 137, 410 [M^+•]	SgH, SgE, SmH, SsH, SsE, StH, StE, StM
24	50.716	2837	2836	90	tetracosanoic acid^* * compounds identified as TMS derivatives.	117 (BP), 73, 425, 132, 145, 440 [M^+•]	SgH, SgE, SsH, SsE, StE, StM
25	53.176	2939	2943	75	trans-catechine^* * compounds identified as TMS derivatives. or isomer	368 (BP), 73, 283, 578	SmE
26	54.152	2983	3004	76	b-tocoferol^* * compounds identified as TMS derivatives.	488 (BP and [M^+•]), 223, 73	SmH
27	56.925	3120	3149	76	a-tocopherol^* * compounds identified as TMS derivatives.	542 (BP and [M^+•]), 237, 73	SgH, SgE, SmH, SsH, SsE, StE, StM
28	57.501	3164	3171	87	quercetin^* * compounds identified as TMS derivatives.	575 (BP), 73, 497	SgH, SmH, SsH, StH, StM
29	59.460	3242	3262	90	stigmasterol^* * compounds identified as TMS derivatives.	83 (BP), 129, 255, 394, 484 [M^+•]	SgH, SgE, SmH, SmM, SsH, SsE, StH, StE, StM
30	60.668	3302	3296	90	b-sitosterol^* * compounds identified as TMS derivatives.	129 (BP), 357, 396, 486 [M^+•]	SgH, SgE, SgM, SmH, SmE, SmM, SsH, SsE, SsM, StH, StE, StM
31	60.895	3314	3312	86	b-amyrin^* * compounds identified as TMS derivatives.	218 (BP), 203, 498 [M^+•]	SmH, SsH, SsE, SsM, StH
32	61.418	3340	3334	96	1-triacontanol^* * compounds identified as TMS derivatives.	495 (BP), 75, 97	SgH, SgE, SgM, SmH, SmE, SsH, SsE, SsM, StH, StM
33	61.885	3355	3354	82	a-amyrin^* * compounds identified as TMS derivatives.	218 (BP), 189, 498 [M^+•]	SmH, SsH
34	63.136	3434	3445	–	triacontanoic acid^* * compounds identified as TMS derivatives.	117 (BP), 73, 145, 509, 524 [M^+•]	StH, StM

Sample^b b sample:SgH = S. gardneri hexane, SgE = S. gardneri ether, SgM = S. gardneri methanol, SmH = S. macranthera hexane, SmE =Senna macranthera ether, SmM = S. macranthera methanol, SsH = S. splendida hexane, SsE = S. splendida ether, SsM = S. splendidamethanol, StH = S. trachypus hexane, StE = S. trachypus ether, StM = S. trachypus methanol;	HTC-116^c c HTC-116 = human colon;	SF-295^d d OVACAR-8 = ovarian carcinoma;	OVCAR-8^e e SF-295 = human glioblastoma;
SgH	59.75 ± 0.60	52.85 ± 5.21	24.61 ± 13.82
SgE	11.63 ± 2.53	24.29 ± 6.13	0.01 ± 0.00
SgM	6.56 ± 10.65	5.77 ± 2.80	0.01 ± 0.00
SmH	28.27 ± 3.05	39.27 ± 7.14	0.01 ± 0.01
SmE	5.59 ± 6.05	20.54 ± 6.22	0.01 ± 0.00
SmM	1.37 ± 3.82	18.56 ± 5.55	44.64 ± 0.99
SsH	13.85 ± 1.29	36.92 ± 0.14	10.43 ± 41.62
SsE	31.37 ± 6.65	48.28 ± 10.04	21.92 ± 1.67
SsM	19.65 ± 5.28	28.66 ± 11.53	0.01 ± 0.00
StH	27.39 ± 3.52	21.19 ± 3.96	0.01 ± 0.00
StE	20.19 ± 1.67	37.12 ± 5.65	9.41 ± 45.94
StM	7.23 ± 1.29	32.38 ± 2.32	35.4 ± 23.31
DOX, IC₅₀ [µmol L^–1]^f f DOX = doxorubicin was the positive control. IC50 is the drug concentration that caused 50% inhibition of cell growth, with the corresponding 95% confidence interval (CI 95%) shown below.	0.12 (0.09-0.17)	0.22 (0.16-0.24)	0.34 (0.31-0.36)

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