NOVEL ALKALOID FROM <i>Rauvolfia capixabae</i>(APOCYNACEAE)

Carlos, Lanamar Almeida; Mathias, Leda; Braz-Filho, Raimundo; Vieira, Ivo Jose Curcino

doi:10.5935/0100-4042.20160002

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Artigo • Quím. Nova 39 (2) • Feb 2016 • https://doi.org/10.5935/0100-4042.20160002 copy

NOVEL ALKALOID FROM Rauvolfia capixabae(APOCYNACEAE)

Authorship SCIMAGO INSTITUTIONS RANKINGS

A new sarpagine-type alkaloid, N_a-methylrauflorine (1), was isolated from Rauvolfia capixabaetogether with isoreserpiline (2),N_b-oxide-isoreserpiline (3), ajmalicine (4), perakine (5) and vinorine (6) alkaloids. These compounds were characterized based on their spectral data basis, mainly one- ⁽¹H, ¹³C, APT) and two-dimensional⁽¹H-¹H-COSY, ¹H-¹H-NOESY, HMQC and HMBC) NMR, and mass spectra, also involving comparison with data from the literature.

Keywords:
Apocynaceae; Rauvolfia capixabae; indole alkaloids

C	HMQC		HMBC		¹H-¹H-NOESY
C	δ_C	δ_H	² J _HC	³ J _HC	¹H-¹H-NOESY
2	79.5	2.64 (br s)	H-3	Me-N_a; 2H-6; 2H-14	Me-N-1 H-14β
3	49.5	3.68 (d, 9.9)		H-15; 2H-21
5	53.1	3.18 (m)	H-6a	H-3; H-15; 2H-21	H-21
6	35.3	2.38 (d, 12.1) 1.66 (m)		H-2
7	58.0	-	H-2; 2H-6	H-3; H-5
8	131.0	-		H-12
9	121.3	6.86 (s)
10	147.5	-		H-12; MeO-10
11	112.7	6.80 (dd, 9.2; 3.0)		H-9
12	116.0	6.84 (d, 9.2)
13	141.9	-		H-9; H-11; Me-N_a
14	31.6	1.91 (m) 1.41 (dd, 13.9; 4.4)	H-3	H-2; H-16	H-21α; H-2β
15	28.6	3.17 (m)	2H-14; H-16	H-3; H-19
16	50.3	2.58 (br t, 5.1)		H-6a; H14a	H-5
17	213.6	-	H-16	H-2; H-5; H-6a
18	12.9	1.65 (d, 7.0)	H-19	2H-21
19	115.5	5.30 (m)	3H-18	H-15; 2H-21	H-15
20	137.5	-	H-15; 2H-21	2H-14; 3H-18
21	55.7	3.50 (br s)		H-5; H-19	H-3; H-5; H-14α; 3H-18
MeO-10	56.4	3.80 (s)
MeN-1	36.9	3.06 (s)		H-2	H-2; H-3

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[1] *e-mail: lanamar@ufsj.edu.br