Chemical Constituents of Psychotria nemorosa Gardner and Antinociceptive Activity

Calixto, Nivea O.; Cordeiro, Millena S.; Giorno, Thais B. S.; Oliveira, Gibson G.; Lopes, Norberto P.; Fernandes, Patricia D.; Pinto, Angelo C.; Rezende, Claudia M.

doi:10.21577/0103-5053.20160219

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Journal of the Brazilian Chemical Society

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Article • J. Braz. Chem. Soc. 28 (5) • May 2017 • https://doi.org/10.21577/0103-5053.20160219 copy

Chemical Constituents of Psychotria nemorosa Gardner and Antinociceptive Activity

Authorship SCIMAGO INSTITUTIONS RANKINGS

Through dereplication strategies using gas chromatography-mass spectrometry (GC-MS) and ultra fast liquid chromatography-tandem mass spectrometry (UFLC-MS/MS), the ethanol extract from Psycotria nemorosa leaves (Rubiaceae) showed to be composed of: cinnamic acid, dihydroactinidiolide, 4-hydroxy-β-ionone, phytol, isophytol, 4,8,12,16-tetramethylheptadecan-4-olide, lupeol, a mixture of α/β-amyrin, the keto and acetylated derivatives, besides stigmast-4-en-3-one, campesterol, stigmasterol and γ-sitosterol by GC-MS. Likewise, by UFLC-MS/MS, the main compounds identified were: butin, resveratrol, rutin, kaempferol 7-O-β-D-glucopyranoside, deacetylasperuloside, epiloganin, hordenine, strictosidine, N-methyl-1,2,3,4-tetrahydro-β-carboline and N-formyl-tryptamine. The antinociceptive activity of the crude extract ant its fractions was reported.

Keywords:
Psychotria nemorosa; hyphenated chromatography-mass spectrometry; antinociceptive activity

Peak	R_t / min	m/z experimental	m/z calculated	Error [ppm]	Protonated molecule [M]⁺	Molecular formula	MS/MS fragments	λ_max / nm	Proposed compound
36	14.8	273.1108	273.1112	-1.5	[M + H]⁺	C₁₅H₁₂O₅	255, 245, 229	274; 318	butin
37	16.8	197.1163	197.1172	4.6	[M + H]⁺	C₁₁H₁₆O₃	179, 164, 112	217	loliolide
38	19.9	385.1259	385.1258	0.4	[M + Na]⁺	C₁₉H₂₂O₇	353, 327, 309	210	gibberellin related compound
39	25.4	316.2820	316.2842	-8.2	[M + H]⁺	C₁₈H₃₇NO₃	298, 280, 250	223	dehydrophytosphingosine
40	26.5	318.2974	318.3003	9.1	[M + H]⁺	C₁₈H₃₉NO₃	300, 282, 265	223	phytosphingosine
41	28.9	412.3161	412.3188	6.4	[M + K]⁺	C₂₂H₄₇NO₃	394, 376, 346	223	2-amino-1,3,4-docosanetriol
42	31.8	353.2645	353.2662	-5.0	[M + Na]⁺	C₁₉H₃₈O₄	335, 262, 248	224	2-palmitoylglycerol
43	34.4	629.3601	629.3601	0	[M + Na]⁺	C₄₁H₅₀O₄	611, 447, 429	223	n.i.

Peak	R_t / min	m/z experimental	m/z calculated	Error [ppm]	Deprotonated molecule [M]^-	Molecular formula	MS/MS fragments	λ_max / nm	Proposed compound
44	6.5	389.1169	389.1175	1.6	[M - H]^-	C₁₇H₂₆O₁₀	357, 227, 169, 151	235	7-epiloganin
45	7.6	227.0646	227.0647	0.1	[M - H]^-	C₁₄H₁₂O₃	185, 183, 159	279; 305	resveratrol
46	9.5	379.0677	379.0671	-1.8	[M - H]^-	C₁₇H₁₆O₁₀	333, 249, 161	208	n.i.
47	12.1	431.1885	431.1896	2.5	[M + Cl]^-	C₂₁H₃₂O₇	385, 223, 161	213	n.i.
48	13.6	371.0950	371.0984	9.1	[M - H]^-	C₁₆H₂₀O₁₀	353, 209, 165, 147	233	deacetylasperuloside
49	14.2	475.1759	475.1762	0.8	[M - H]^-	C₂₈H₂₈O₇	429, 289, 235, 163	218	n.i.
50	15.3	363.0713	363.0722	2.2	[M - H]^-	C₁₇H₁₆O₉	317, 267, 241	220	n.i.
51	15.9	193.0458	193.0506	-25.0	[M - H]^-	C₁₀H₁₀O₄	178, 149, 134	285; 322	ferulic acid
52	17.7	187.0930	187.0976	-24.7	[M - H]^-	C₉H₁₆O₄	169, 143, 125	205	azelaic acid
53	18.9	401.1200	401.1220	-5.0	[M + Cl]^-	C₁₅H₂₆O₁₀	369, 325, 193	220	n.i.
54	32.4	721.3543	721.3526	2.4	[M - H]^-	C₄₁H₅₄O₁₁	675, 397	224	n.i.
55	36.5	559.3058	559.3065	-1.2	[M - H]^-	C₃₅H₄₄O₆	513, 379, 277	230	n.i.

Peak	R_t / min	m/z experimental	m/z calculated	Error [ppm]	Protonated molecule [M]+	Molecular formula	MS/MS fragments	λ_max / nm	Proposed compound
56	3.2	166.1215	166.1226	-7.2	[M + H]⁺	C₁₀H₁₅NO	121, 103, 91	278	hordenine
57	4.4	328.1719	328.1731	-3.6	[M + Na]⁺	C₁₄H₂₇NO₆	166, 121	-	n.i.
58	6.0	164.1054	164.1046	4.7	[M + H]⁺	C₁₀H₁₃NO	147, 119, 91	260	eusterol
59	6.4	310.1254	310.1261	2.3	[M + Na]⁺	C₁₃H₂₁NO₆	292, 264, 166	206	n.i.
60	6.8	210.1111	210.1101	-4.9	[M + Na]⁺	C₉H₁₇NO₃	192, 166	215	8-amino-7-oxononanoic acid
61	8.0	244.0309	244.0330	8.5	[M + K]⁺	C₆H₁₁N₃O₅	205, 202	202	sugar containing azide
62	8.5	360.1757	360.1765	2.3	[M + H]⁺	C₁₅H₂₅N₃O₇	315, 297, 191	202	n.i.
63	11.2	177.0533	177.0546	7.2	[M + Na]⁺	C₈H₁₀O₃	145, 159	229; 282	syringol/vanillic alcohol/ hydroxytyrosol
64	11.5	207.1367	207.1356	-5.4	[M + Na]⁺	C₁₁H₂₀O₂	190, 152, 139	209	n.i.
65	11.8	374.1917	374.1922	-1.1	[M + H]⁺	C₁₆H₂₇N₃O₇	329, 297, 209, 173	214	n.i.
66	14.1	531.2283	531.2313	5.7	[M + H]⁺	C₂₇H₃₄N₂O₉	514, 369	217	stryctosidine
67	16.6	261.1085	261.1081	1.7	[M + H]⁺	C₁₀H₁₆N₂O₆	243, 201, 177	219	n.i.
68	17.5	461.1913	461.1918	-1.1	[M + H]⁺	C₂₃H₂₈N₂O₈	371, 299, 158	219	n.i.
69	18.6	187.1226	187.1233	2.2	[M + H]⁺	C₁₂H₁₄N₂	158, 144	219	N-methyl-1,2,3,4-tetrahydro- β-carboline
70	20.4	149.0207	149.0209	1.8	[M + Na]⁺	C₆H₆O₃	132, 131	275	pyrogallol related compound

Peak	R_t / min	m/z experimental	m/z calculated	Error [ppm]	Deprotonated molecule [M]-	Molecular formula	MS-MS fragments	λ_max / nm	Proposed compound
71	3.1	361.0893	361.0907	3.9	[M + Cl]^-	C₁₂H₂₂O₁₀	325, 265, 163	-	n.i.
72	5.4	385.1311	385.1293	-4.8	[M - H]^-	C₂₁H₂₂O₇	339, 307	-	n.i.
73	6.6	435.1216	435.1216	-0.1	[M + Cl]^-	C₂₂H₂₄O₇	389	205	n.i.
44	7.0	389.1175	389.1168	-3.5	[M - H]^-	C₁₇H₂₆O₁₀	357, 227, 169, 151	235	7-epiloganin
74	9.0	609.1453	609.1469	-2.1	[M - H]^-	C₂₇H₃₀O₁₆	301, 271, 179	258; 357	rutin
75	9.5	447.1827	447.1832	-0.9	[M - H]^-	C₂₁H₂₀O₁₁	325, 285, 284	228; 284; 349	kaempferol 7-O-β-D-glucopyranoside
76	12.1	501.1568	501.1573	-1.0	[M - H]^-	C₁₇H₃₀N₂O₁₅	483, 441, 307, 217	205	n.i.
77	12.5	449.1985	449.1988	0.8	[M - H]^-	C₁₅H₃₄N₂O₁₃	403, 319, 283	212	n.i.
78	13.4	695.2114	695.2134	-2.9	[M - H]^-	C₃₉H₃₆O₁₂	635, 532, 429, 387, 325, 235	216	n.i.
79	15.5	387.1059	387.1045	3.5	[M - H]^-	C₁₅H₂₀N₂O₁₀	369, 343, 284, 193	217	n.i.
80	18.1	187.0934	187.0949	7.9	[M - H]^-	C₁₁H₁₂N₂O	159, 130	230; 290	N-formyl-tryptamine
81	20.7	401.1213	401.1202	1.9	[M - H]^-	C₁₆H22N₂O₁₀	369, 325, 282	220	n.i.

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