Ixorine, a New Cyclopeptide Alkaloid from the Branches of Ixora brevifolia

Figure 2 Selected key HMBC (¹H ¹³C) and NOESY (¹H ¹H) correlations for ixorine (1). 

Figure 1 Structures of compounds 1-4 isolated from the branches of I. brevifolia. 

Ixorine (1)

HRESIMS m/z, calcd.: C₃₀H₄₀N₄O₄ [M + H]⁺: 521.3044; found: 521.3049; [α]_D²⁰ = -292.3 (c 0.001, CHCl₃); ¹H NMR (300 MHz, CDCl₃) and ¹³C NMR (75 MHz, CDCl₃), see Table 1.

Table 1 NMR spectroscopic data (300 MHz, CDCl3) for ixorine (1) 

Position	δC	δH (mult., J in Hz)	HMBC	COSY
1	156.3	−	H-14, H-16	−
2	−	−	−	−
3	81.7	4.91 (dd, 8.0, 2.1)	H-4, H-18, H-19	H-4
4	55.6	4.44 (dd, 9.0, 8.0)	−	H-20 (NH)
5	171.6	−	H-6 (NH)	−
6	−	5.94 (d, 6.3, NH)	−	−
7	55.2	4.30 (m)	H-28	H-28
8	167.2	−	H-28	−
9	−	6.20 (sl, NH)	−	−
10	125.7	6.56 (m)	−	−
11	118.4	6.40 (d, 6.6)	H-13	−
12	131.8	−	H-14	−
13	131.7	7.03 (m)	−	H-14
14	121.9	7.15 (m)	−	−
15	122.7	7.03 (m)	−	H-16
16	130.2	6.92 (m)	−	−
17	29.3	2.00 (m)	H-18, H-19	H-18, H-19
18	20.4	1.25 (d, 7.2)	H-17, H-19	−
19	15.2	1.00 (d, 6.6)	H-17	−
20	−	6.94 (m, NH)	−	−
21	172.4	−	H-22, H-23	−
22	75.2	2.40 (d, 4.2)	H-24, H-25, H-26, H-27	H-26, H-27
23	27.8	2.05 (m)	H-24, H-25	H-24, H-25
24	21.0	1.05 (d, 6.9)	−	−
25	17.6	0.93 (d, 6.6)	−	−
26	43.1	2.14 (s)	H-27	−
27	43.1	2.14 (s)	−	−
28	37.1	2.76 (dd, 13.8, 4.5)/3.07 (m)	H-30, H-30’	H-28
29	135.7	−	H-7, H-28, H-31, H-31’	−
30, 30’	129.6	7.15 (m)	−	H-31, H-31’
31, 31’	129.0	7.34 (m)	−	−
32	127.4	7.24 (m)	−	H-30, H-30’

Journal of the Brazilian Chemical Society

On-line version ISSN 1678-4790

J. Braz. Chem. Soc. vol.27 no.4 São Paulo Apr. 2016

http://dx.doi.org/10.5935/0103-5053.20150326

ARTICLES

Ixorine, a New Cyclopeptide Alkaloid from the Branches of Ixora brevifolia

Rebeca P. Medina^a  , Ivânia T. A. Schuquel^a  , Armando M. Pomini^a  , Cleuza C. Silva^a  , Cecília M. A. Oliveira^b  , Lucília Kato^b  , Celso V. Nakamura^c  , Silvana M. O. Santin^{*  a} 

^aDepartamento de Química, Universidade Estadual de Maringá, Av. Colombo 5790, 87020-900 Maringá-PR, Brazil

^bInstituto de Química, Universidade Federal de Goiás, Campus II, Samambaia, 74001-970 Goiânia-GO, Brazil

^cDepartamento de Análises Clínicas e Biomedicina, Universidade Estadual de Maringá, Av. Colombo 5790, 87020-900 Maringá-PR, Brazil

ABSTRACT

The isolation and structure determination of new cyclic peptide alkaloid ixorine, along with five known constituents frangulanine, syringaresinol, cinnamtannin B-1, daucosterol and mannitol from the branches of Ixora brevifolia are described. The cyclic peptide frangulanine is being described for the first time in the Rubiaceae family. The structures were elucidated on their spectral data basis, mainly one- (¹H, ¹³C, DEPT) and two-dimensional (COSY, NOESY, HSQC and HMBC) nuclear magnetic resonance (NMR) and by comparison with data from the literature. The mixture of two cyclopeptide alkaloids showed weak activity against Leishmania amazonensis........http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016000400753&lng=en&nrm=iso&tlng=en


Key words: Ixora brevifolia,  Rubiaceae,  cyclopeptide alkaloids,  Leishmania
see..........http://www.scielo.br/pdf/jbchs/v27n4/0103-5053-jbchs-27-04-0753-suppl01.pdf

SUPPLEMENTARY INFORMATION

1D and 2D NMR spectra for compounds 1-2 are available free of charge online
0103-5053-jbchs-27-04-0753-suppl01.pdf
^*e-mail: smoliveira@uem.br

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 Palolem Beach, South Goa, India. goa

Palolem Beach

Village in India

Palolem is a beach village situated in Canacona in southern Goa, India. Wikipedia

 
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