New Terpenoids from Croton limae (Euphorbiaceae)

Sousa, Antonio H.; Silva Junior, José N.; Guedes, Maria L. S.; Braz-Filho, Raimundo; Costa-Lotufo, Letícia V.; Araújo, Ana J.; Silveira, Edilberto R.; Lima, Mary A. S.

doi:10.5935/0103-5053.20150124

Antonio H. Sousa

Departamento de Química Orgânica e Inorgânica, Centro de Ciências, Universidade Federal do Ceará, CP 12.200, 60021-940 Fortaleza-CE, Brazil

José N. Silva Junior

Departamento de Química Orgânica e Inorgânica, Centro de Ciências, Universidade Federal do Ceará, CP 12.200, 60021-940 Fortaleza-CE, Brazil

Maria L. S. Guedes

Departamento de Botânica, Instituto de Biologia, Universidade Federal da Bahia, Campus Universitário de Ondina, 40170-290 Salvador-BA, Brazil

Raimundo Braz-Filho

Laboratório de Ciências Químicas, Universidade Estadual do Norte Fluminense Darcy Ribeiro, 28013-602 Campos dos Goytacazes-RJ, Brazil

Departamento de Química, Universidade Federal Rural do Rio de Janeiro, 23890-000 Seropédica-RJ, Brazil

Letícia V. Costa-Lotufo

Departamento de Farmacologia e Fisiologia, Centro de Ciências da Saúde, Universidade Federal do Ceará, CP 12.200, 60430-270 Fortaleza-CE, Brazil

Ana J. Araújo

Departamento de Farmacologia e Fisiologia, Centro de Ciências da Saúde, Universidade Federal do Ceará, CP 12.200, 60430-270 Fortaleza-CE, Brazil

Edilberto R. Silveira

Departamento de Química Orgânica e Inorgânica, Centro de Ciências, Universidade Federal do Ceará, CP 12.200, 60021-940 Fortaleza-CE, Brazil

Mary A. S. Lima ^**e-mail: mary@dqoi.ufc.br

Departamento de Química Orgânica e Inorgânica, Centro de Ciências, Universidade Federal do Ceará, CP 12.200, 60021-940 Fortaleza-CE, Brazil

*e-mail: mary@dqoi.ufc.br

H	1^a a 1H NMR data were recorded at 500 MHz; ^,^c c solvent CDCl3;	2^b b 1H NMR data were recorded at 300 MHz; ^,^c c solvent CDCl3;	3^a a 1H NMR data were recorded at 500 MHz; ^,^d d solvent MeOD	4^b b 1H NMR data were recorded at 300 MHz; ^,^d d solvent MeOD	5^b b 1H NMR data were recorded at 300 MHz; ^,^d d solvent MeOD
H	δ_H	δ_H	δ_H	δ_H	δ_H
1	0.86 (td, 12.8, 3.30)	1.68 (m)	1.19 (m)	1.33 (m)	1.81 (qd, 13.2, 4.3)
	1.76 (m)	2.22 (m)	1.54 (m)	1.58 (qd, 13.1, 5.2)	2.08 (m)
2	1.63 (m)	2.39 (ddd, 14.2, 4.9, 1.9)	1.18 (m)	1.63 (td, 14.2, 7.3)	2.33 (dq, 14.2, 2.0)
		2.56 (td, 14.2, 4.9)	1.58 (m)	2.03 (ddd, 14.2, 7.3, 1.7)	2.45 (td, 14.2, 6.8)
3	1.60 (m)	-	3.48 (t, 2.5)	3.48 (brs)	-
	1.79 (m)
4	-	-	-	-	-
5	1.77 (m)	-	-	-	-
6	1.25 (m)	1.50 (m)	1.43 (m)	1.34 (td, 13.0, 4.1)	3.95 (dd, 11.6, 3.9)
	1.76 (m)	1.64 (m)		1.67 (dt, 13.0, 3.1)
7	1.24 (m)	1.44 (m)	1.32 (m)	1.35 (m)	1.62 (dd, 13.5, 2.4)
	1.92 (m)	1.42 (m)	1.44 (m)	1.49 (m)	2.04 (m)
8	-	1.70 (m)	1.82 (m)	1.50 (m)	2.05 (m)
9	1.20 (s)	-	-	-	-
10	-	2.51 (dd, 12.4, 2.9)	1.38 (m)	1.87 (m)	2.64 (dd, 13.3, 2.6)
		1.59 (m)
11	1.53 (m)	1.95 (dd, 15.7, 9.0)	1.77 (dd, 15.1, 6.8)	1.40 (d, 15.9)	2.86 (d, 16.1)
			1.92 (dd, 15.1, 6.8)	1.51 (d, 15.7)	2.92 (d, 16.1)
12	1.65 (m)	4.92 (dd, 9.0, 1.5)	4.74 (t, 6.2)	2.05 (m)	-
	1.67 (m)
13	2.48 (m)	_-	_-	_-	_-
	1.30 (d, 13.8)
14	12.43 (d, 13.8)	6.38 (brs)	6.48 (d, 0.9)	5.47 (t, 6.8)	6.78 (br s)
15	-	7.38 (m)	7.46 (t, 1.5)	4.14 (d, 6.8)	7.59 (br s)
16	2.10 (m)	7.38 (m)	7.48 (s)	4.10 (s)	8.02 (br s)
17	1.28 (m)	0.79 (d, 6.7)	0.92 (d, 6.7)	0.80 (d, 6.0)	0.95 (d, 6.6)
	1.94 (m)
18	-	1.37 (s)	1.06 (s)	1.19 (s)	1.45 (s)
19	1.15 (s)	0.81 (s)	1.13 (s)	1.12 (s)	0.97 (s)
20	1.10 (s)	0.74 (s)	0.76 (s)	0.75 (s)	0.87 (s)
1’	2.03 (m)	-	-	-	4.45 (d, 7.7)
2’	-	-	-	-	3.13 (dd, 9.2, 7.9)
3’	5.21 (br s)	-	-	-	3.33 (m)
4’	2.18 (d, 17.4)	-	-	-	3.27 (q, 9.5)
	2.24 (d, 17.4)
5’	2.08 (m)	-	-	-	3.36 (m)
6’	-	-	-	-	3.66 (dd, 11.8, 5.4)
					3.85 (dd, 11.8, 2.2)
7’	1.12 (m)	-	-	-	-
	2.35 (m)
8’	1.26 (s)	-	-	-	-
9’	0.82 (s)	-	-	-	-
10’	1.98 (m)	-	-	-	-
	2.05 (m)

C	1^a a 13C NMR data were recorded at 125 MHz; ^,^c c solvent CDCl3;	2^b b 13C NMR data were recorded at 75 MHz; ^,^c c solvent CDCl3;	3^a a 13C NMR data were recorded at 125 MHz; ^,^d d solvent MeOD.	4^b b 13C NMR data were recorded at 75 MHz; ^,^d d solvent MeOD.	5^b b 13C NMR data were recorded at 75 MHz; ^,^d d solvent MeOD.
C	δ_C	δ_C	δ_C	δ_C	δ_C
1	38.6	23.8	18.1	17.7	24.1
2	18.4	36.4	30.6	31.2	37.7
3	36.9	216.0	77.9	77.1	214.1
4	47.6	81.8	77.3	77.5	83.9
5	49.5	45.4	43.6	42.7	51.0
6	21.9	31.7	34.1	33.7	85.4
7	33.7	26.8	27.9	28.0	35.8
8	53.2	37.3	38.6	37.5	36.7
9	52.3	39.9	40.6	39.9	43.0
10	39.2	42.2	44.4	41.9	43.9
11	17.7	45.9	46.8	38.8	47.8
12	24.8	63.5	63.9	29.5	197.4
13	33.0	131.5	132.0	144.1	130.9
14	37.4	108.4	110.0	127.3	109.4
15	224.1	143.7	144.7	59.0	146.1
16	52.9	138.4	140.4	60.5	149.9
17	23.4	16.0	16.9	16.6	16.6
18	184.9	21.9	23.4	21.3	23.0
19	16.2	15.3	16.6	18.0	11.0
20	18.0	17.9	19.0	19.0	17.9
1’	45.8	-	-	-	106.6
2’	148.0	-	-	-	75.3
3’	116.6	-	-	-	78.1
4’	31.4	-	-	-	71.7
5’	41.0	-	-	-	78.0
6’	38.1	-	-	-	62.8
7’	31.9	-	-	-	-
8’	26.5	-	-	-	-
9’	21.3	-	-	-	-
10’	35.5	-	-	-	-

[1] *e-mail: mary@dqoi.ufc.br

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New Terpenoids from Croton limae (Euphorbiaceae)