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.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. Medinaa , Ivânia T. A. Schuquela , Armando M. Pominia , Cleuza C. Silvaa , Cecília M. A. Oliveirab , Lucília Katob , Celso V. Nakamurac , 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=enKey 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 online0103-5053-jbchs-27-04-0753-suppl01.pdf
*e-mail: smoliveira@uem.br
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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