FLAVONOIDES DE <i>Piper glandulosissimum</i> Yuncker
                    (Piperaceae)

Santos, Fabiano Pereira; Alves, Harley da Silva; Lima, Edeltrudes de Oliveira; Chaves, Maria Célia de Oliveira

doi:10.5935/0100-4042.20140310

Sumário Anterior Atual Seguinte

Sumário

Artigo • Quím. Nova 38 (2) • Fev 2015 • https://doi.org/10.5935/0100-4042.20140310 linkcopiar

FLAVONOIDES DE Piper glandulosissimum Yuncker (Piperaceae)

FLAVONOIDS FROM Piper glandulosissimum Yuncker (Piperaceae)

Autoria SCIMAGO INSTITUTIONS RANKINGS

Resumo

Three flavanones, two chalcones and one dihydrochalcone were isolated from the branches of Piper glandulosissimum. All isolated compounds were characterized based on IR, UV, ¹H and ¹³C NMR, including 2D NMR analyses (HMQC, HMBC, COSY and NOESY) and comparison with the literature. The compound 7-hydroxy-5,8-dimethoxyflavanone displayed antimicrobial activity against Staphylococcus aureus, S. epidermidis, Trichophyton mentagrophytes and Microsporum canis.

H/C	1				1a
H/C	δ_H	δ_C	² J	³ J	δ_H	δ_C
1’	-	106,69	-	-	-	121,67
2’	-	160,89	-	-	-	142,52
3’	-	130,07	-	-	-	138,37
4’	-	158,14	-	-	-	145,39
5’	6,13 (s, 1H)	91,79	C-4’, C-6’	C-3’, C-1’	6,62 (s, 1H)	104,50
6’	-	159,84	-	-	-	152,73
1	-	136,49	-	-	-	134,42
2	7,74-7,70 (m, 2H)	129,32	-	-	7,75-7,70 (m, 2H)	128,59
3	7,49-7,42 (m, 3H)	129,92	-	C-5, C-1	7,38-7,35 (m, 3H)	128,91
4	7,49-7,42 (m, 3H)	131,11	-	-	7,38-7,35 (m, 3H)	130,71
5	7,49-7,42 (m, 3H)	129,92	-	C-3, C-1	7,38-7,35 (m, 3H)	128,91
6	7,74-7,70 (m, 2H)	129,32	-	-	7,75-7,70 (m, 2H)	128,59
β	8,03 (d, J=15,6 Hz, 1H)	128,51	C-1, C- α	-	7,43 (d, J=16,0 Hz, 1H)	127,31
α	7,78 (d, J=15,6 Hz, 1H)	142,96	-	-	6,92 (d, J=16,0 Hz, 1H)	146,16
β’	-	193,79	-	-	-	191,49
OH-2’	14,40 (s, 1H)	-	C-2’	C-3’, C-1’	-	-
OH-4’	9,17 (sl, 1H)	-	-		-	-
OCH₃-3’	3,76 (s, 3H)	60,69	-	C-3’	3,75 (s, 3H)	61,20
OCH₃-6’	3,98 (s, 3H)	56,58	-	C-6’	3,74 (s, 3H)	56,29
CH₃COO-2’	-	-	-		2,17 (s, 3H)	20,39
CH₃COO-4’	-	-	-		2,34 (s, 3H)	20,77
CH₃COO-2’	-	-	-		-	168,18
CH₃COO-4’	-	-	-		-	168,45

H/C	2				3
H/C	δ_H	δ_C	² J	³ J	δ_H	δ_C	² J	³ J
1’	-	105,59	-	-	-	106,00
2’	-	167,10	-	-	-	168,37
3’	5,92 (d, J=2,0 Hz, 1H)	96,15		C-1’	5,92 (d, J=2,2 Hz, 1H)	97,13	C-2’	C-1’, C-5’
4’		163,21*				166,60
5’	5,88 (d, J=2,0 Hz, 1H)	91,62	C-4’, C-6’	C-1’	5,98 (d, J=2,2 Hz, 1H)	92,25	C-6’	C-1’, C-3’
6’		164,82*				165,08
1		135,49				143,22
2	7,54-7,49 (m, 2H)	128,21		C-4, C-6	7,28-7,23 (m, 4H)	127,07	C-1	C-4, C-6
3	7,34-7,29 (m, 3H)	128,76		C-1	7,28-7,23 (m, 4H)	129,56	C-2, C-4
4	7,34-7,29 (m, 3H)	129,91			7,19-7,17 (m, 1H)	127,07		C-2, C-6
5	7,34-7,29 (m, 3H)	128,76		C-1	7,28-7,23 (m, 4H)	129,56	C-4
6	7,54-7,49 (m, 2H)	128,21	C-1	C-4	7,28-7,23 (m, 4H)	127,07	C-1, C-5	C-2, C-4
β	7,81 (d, J=15,6 Hz, 1H)	127,52	C-1	C- β’	2,95 (t, J=7,5 Hz, 2H)	32,25	C-α, C-1	C- β’
α	7,63 (d, J=15,6 Hz, 1H)	141,92	C- β’	C-1	3,28 (t, J=7,5 Hz, 2H)	47,11	C- β, C- β’	C-1
β’		192,53				205,83
OH-2’	14,35 (s, 1H)		C-2’	C-1’, C-3’
OH-4’
OCH₃-6’	3,83 (s, 3H)	55,71			3,86 (s, 3H)	56,27		C-6’

H/C	4				5	6
H/C	δ_H	δ_C	² J	³ J	δ_H	δ_C	δ_H	δ_C
2	5,55 (dd, J=12,7 e 3,0 Hz, 1H)	80,16			5,58 (dd, J=12,0 e 3,0 Hz, 1H)	78,31	5,54 (dd, J=12,4 e 3,0 Hz, 1H)	79,91
3	2,97 (dd, J=12,7 e 16,38 Hz); 2,71 (dd, J=16,38 e 3,0 Hz, 1H)	46,44	C-4, C-2	C-1’	3,26 (dd, J=17,1 e 12,0 Hz); 2,86 (dd, J=17,1 e 3,0 Hz, 1H)	42,46	2,98 (dd, J=12,4 e 16,4 Hz); 2,74 (dd, J=16,4 e 3,0 Hz, 1H)	46,46
4		188,12				196,66		188,33
5		158,85				155,75		159,72
6	6,21 (s, 1H)	94,02	C-7, C-5	C-8, C-10	6,22 (s, 1H)	92,58	6,40 (s, 1H)	91,25
7		157,35			-	157,23		158,74
8		130,29			-	126,65		131,98
9		157,47			-	148,02		157,14
10		106,55			-	102,34		107,16
1’		140,69			-	138,87		140,73
2’	7,62-7,61 (m, 2H)	127,14		C-4’, C-2, C-6’	7,57-7,55 (m, 2H)	126,58	7,61-7,58 (m, 2H)	127,14
3’	7,59-7,36 (m, 3H)	129,56	C-2’	C-5’, C-1’	7,46-7,37 (m, 3H)	128,43	7,48-7,36 (m, 3H)	129,54
4’	7,59-7,36 (m, 3H)	129,28		C-6’, C-2’	7,46-7,37 (m, 3H)	128,36	7,48-7,36 (m, 3H)	129,23
5’	7,59-7,36 (m, 3H)	129,56	C-6’	C-3’, C-1’	7,46-7,37 (m, 3H)	128,43	7,48-7,36 (m, 3H)	129,54
6’	7,62-7,61 (m, 2H)	127,14		C-4’, C-2, C-2’	7,57-7,55 (m, 2H)	126,58	7,61-7,58 (m, 2H)	127,14
OCH₃-5	3,79 (s, 3H)	56,22		C-5	-	-	3,94 (s, 3H)	56,59
OCH₃-7		-			3,84 (s, 3H)	56,12	3,86 (s, 3H)	56,45
OCH₃-8	3,76 (s, 3H)	61,32		C-8	-	-	3,71 (s, 3H)	60,99
OH-5		-			11,80 (s, 1H)	155,75
OH-7	9,03 (sl, 1H)	-			-
OH-8		-			8,18 (s, 1H)	126,65

Microrganismo e cepa testada	400 μg/mL	200 μg/mL	100 μg/mL	50 μg/mL	Controle: Cloranfenicol (30 μg/mL)	Controle: Cetoconazol (100 μg/mL)
Staphylococcus aureus - ATCC 6528	12	10	7	0	20	_
Staphylococcus epidermidis - ATCC 12.228	10	0	0	0	21	_
Trichophyton mentagrophytes - LM 06	20	16	12	8	_	22
Microsporum caniis - LM 828	22	18	13	10	_	23

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Sociedade Brasileira de Química Instituto de Química, Universidade Estadual de Campinas (Unicamp), CP6154, 13083-0970 - Campinas - SP - Brazil
E-mail: quimicanova@sbq.org.br

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