Complete assignments of NMR data and assessment of trypanocidal activity of new eremantholide C derivatives

SAÚDE-GUIMARÃES, DÊNIA A.; RASLAN, DÉLIO S.; CHIARI, EGLER; OLIVEIRA, ALAÍDE B. DE

doi:10.1590/0001-3765201420140167

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Chemical Sciences • An. Acad. Bras. Ciênc. 86 (4) • Dec 2014 • https://doi.org/10.1590/0001-3765201420140167 copy

Complete assignments of NMR data and assessment of trypanocidal activity of new eremantholide C derivatives

Authorship SCIMAGO INSTITUTIONS RANKINGS

Chemical transformations of eremantholide C (1), a sesquiterpene lactone that was isolated from Lychnophora trichocarpha Spreng. led to five new derivatives: 1′,2′- epoxyeremantholide C (2), 5-n-propylamine-4,5-dihydro-1′,2′-epoxyeremantholide C (3), 5-n-propylammonium-4,5-dihydro-1′,2′-epoxyeremantholide C chloride (4), 5-n-propylammonium-4,5-dihydroeremantolide C chloride (5) and 16-O-ethyleremantholide C (6). The structures of all these derivatives were assigned on the basis of IR, MS, ¹H and ¹³C NMR data by 1D and 2D techniques. Eremantholide C and the derivatives 2, 4 and 5 were evaluated against trypomastigotes Y and CL strains of Trypanosoma cruzi. Eremantholide C completely inhibited the growth of both the parasites strains while all derivatives were partially active against the CL strain and inactive against the Y strain.

Eremantholide C derivatives; Lychnophora trichocarpha ; NMR; sesquiterpene lactones; trypanocidal activity

H	1^* x – Superimposed signal with D2O. ^,1	2^ - 400 MHz, ^,1	3^ - 400 MHz, ^,1	4^ - 400 MHz, ^,2	5^ - 400 MHz, ^,2	6^ - 400 MHz, ^,1
2	5.63 s	5.62 s	5.56 s	5.99 s	5.93 s	5.62 s
4	-	-	2.89 q J _4,15 = 7.2	3.56 q J_4,15 = 7.2	3.45 q J _4,15 = 7.2	-
5	6.04-6.03 m	6.03-6.00 m	2.99 brs	3.97 brs	3.88 brs	6.03-6.01 m
6	5.02-4.98 m	5.02-4.97 m	4.26 d J_6,7 = 6.5	4.74 a	4.73 d J_6,7 = 7.9	4.90-4.86 m
7	2.82 dd J_6,7 = 7.1; J_7,8 = 4.2	2.87 dd J_6,7 = 7.3; J_7,8 = 4.2	2.95 dd J_6,7 = 6.5; J_7,8 = 4.9	3.09 dd J_6,7 = 7.8; J_7,8 = 4.2	3.04 dd J_6,7 = 7.8; J_7,8 = 4.3	2.84 dd J_6,7 = 7.2; J_7,8 = 4.4
8	4.09 ddd J_7,8 = 4.2; J_8,9a = 2.5; J_8,9b = 12.0	4.07 ddd J_7,8 = 4.2; J_8,9a = 2.6; J_8,9b = 11.9	3.91 ddd J_7,8 = 4.9; J_8,9a = 2.3; J_8,9b = 11.9	3.92 m	3.96 ddd J_7,8 = 4.3; J_8,9a = 2.8; J_8,9b = 113	3.85 ddd J_7,8 = 4.4; J_8,9a = 2.4; J_8,9b = 12.0
9a	2.48 dd J_8,9a = 2.5; J_9a,9b = 13.5	2.39 dd J_8,9a = 2.6; J_9a,9b = 13.6	2.39 dd J_8,9a = 2.3; J_9a,9b = 13.5	2.32 dd J_8,9a = 2.3; J_9a,9b = 13.6	2.27 dd J_8,9a = 2.8; J_9a,9b = 13.8	2.41 dd J_8,9a = 2.4; J_9a,9b = 13.6
9b	2.00 dd J_8,9b = 12.0; J_9a,9b = 13.5	1.94 dd J_8,9b = 11.9; J_9a,9b = 13.6	1.90 dd J_8,9b = 11.9; J_9a,9b = 13.5	2.39 J_8,9b = 11.5; J_9a,9b = 13.6	2.34 dd J_8,9b = 11.3; J_9a,9b = 13.8	2.06 dd J_8,9b = 12.0; J_9a,9b = 13.6
13	1.18 s	1.33 s	1.38 s	1.39 s	1.21 s	1.16 s
14	1.45 s	1.48 s	1.43 s	1.50 s	1.45 s	1.50 s
15	2.05 t J_5.15 =_6,15= 1.9	2.05 t J_5,15 =_6,15= 2.0	1.37 d J_4,15 = 7.2	1.52 d J_4,15 = 7.2	1.48 d J_4,15 = 7.2	2.06 dd J_5,15 = 2.0; J_6,15 = 1.6
2′a	5.31 brs	3.11 d J_2′a,2′b = 5.5	3.12 d J_2′a,2′b = 5.5	4.04 d J_2′a,2′b = 11.9	5.22 brs	5.28 d J_2′a,2′b = 1.2
2′b	5.07 t J_2′a,2′b = 1.6	2.70 d J_2′a,2′b = 5.5	2.71 d J_2′a,2′b = 5.5	3.75 d J_2′a,2′b = 11.9	5.13 t J_2′a,2′b = 1.4	5.13 brs
3′	1.91 s	1.55 s	1.57 s	1.50 s	1.77 s	1.79 s
4′a	-	-	2.8 dt J_4′a,4′b = 11.2; J_4′a,5′ = 7.0	3.28 td J_4′a,4′b = 11.2; J_4′a,5′ = 5.8;	3.18 dt J_4′a,4′b = 10.5; J_4′a,5′ = 5.7	3.36 dq J_4′a,4′b = 9.2; J_4′a,5′ =7.2
4′b	-	-	2.53 dt J_4′a,4′b = 11.2; J_4′b,5′ = 6.9;	3.17 td J_4′a,4′b = 11.2; J_4′b,5′ =5.8	3.09 dt J_4′a,4′b = 10.5; J_4′b,5′ =5.7	3.20 m
5′	-	-	1.50 m	1.80 m	1.75 m	1.07 t J_{4′a,5′ =,4′b,5′} = 7.2
6′	-	-	0.93 t J_5′,6′ = 7.3	0.99 t J_5′,6′ = 7.4	0.94 t J_5′,6′ = 7.3	-
OH	3.79 s	3.69 s

C	1^* * - 75 MHz; ^,1	2^** 1 - CDCl3; 2 - D2O. ^,1	3^** 1 - CDCl3; 2 - D2O. ^,1	4^** 1 - CDCl3; 2 - D2O. ^,2	5^** 1 - CDCl3; 2 - D2O. ^,2	6^** 1 - CDCl3; 2 - D2O. ^,1
C-1	205.89	205.23	204.53	209.06	209.34	205.24
C-2	104.54	104.50	104.03	105.93	106.08	104.45
C-3	187.27	186.64	192.93	192.39	192.53	186.91
C-4	130.00	130.15	38.14	33.44	33.68	139.10
C-5	134.77	134.28	57.18	58.65	57.30	134.75
C-6	81.46	81.34	82.42	80.77	81.00	81.75
C-7	62.53	63.06	65.24	63.79	63.99	63.10
C-8	78.37	78.38	77.45	76.47	77.05	78.43
C-9	43.46	43.25	43.84	42.38	42.60	43.89
C-10	90.24	89.95	89.88	91.88	91.99	89.98
C-11	59.88	58.43	58.51	61.65	60.61	60.00
C-12	175.72	174.70	175.09	177.21	178.19	175.76
C-13	21.94	20.64	21.16	21.52	20.83	21.66
C-14	20.48	20.39	20.51	20.16	20.22	20.64
C-15	20.30	20.33	16.70	15.06	15.17	20.49
C-16	106.09	104.57	104.94	107.06	107.27	109.59
C-1′	142.22	59.60	59.71	76.67	141.39	139.28
C-2′	115.80	53.59	53.80	50.06	116.63	117.61
C-3′	19.00	11.44	17.55	20.07	19.19	18.46
C-4′	-	-	50.51	49.11	49.22	57.26
C-5′	-	-	17.52	19.04	18.70	15.29
C-6′	-	-	11.65	10.52	10.62	-

Compound	Y Strain (µg/mL)	CL Strain (µg/mL)
1	3600 (100%)	1800 (100%)
2	3290 (NI)	823 (50%)
4	4155 (NI)	1039 (50%)
5	4009 (NI)	1002 (50%)

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[1] Correspondence to: Dênia Antunes Saúde-Guimarães E-mails: saude@ef.ufop.br/ saudeguima@gmail.com