.
http://www.scielo.br/scielo.php?pid=S0001-37652013000200487&script=sci_arttext
In the 3JCH gHMBC experiment (Figure 4), H-3 correlated with C3a (δ 104.0), C4 (δ 110.0), C5 (δ 163.0), C7 (δ 158.0), C7a (δ151.0) and C1 (δ 173.0); H-6 correlated with C1, C4, C5, C7 and C7a; H-8 correlated with C3a, C4 and C5 and H-9 correlated with C7.
Figure 4
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Position | Mycophenolic acid | 5-hydroxy-7methoxy-4methylphthalide | ||||
---|---|---|---|---|---|---|
δ 13C | δ 1H (multiplicity, J in Hz) | 1H-13C gHMBC* | δ 13C | δ 1H (multiplicity, J in Hz) | 1H-13C gHMBC * | |
1 | 173.0 | - | 173.0 | - | - | |
3 | 70.0 | 5.18 (2H, br s) | 1; 3a | 68.0 | 5.15 (2H, br s) | 1; 3a; 4; 5; 7; 7a |
3a | 122.1 | - | - | 104.0 | - | - |
4 | 116.7 | - | - | 110.0 | - | - |
5 | 163.7 | - | - | 163.0 | - | - |
6 | 106.4 | - | - | 98.0 | 6.49 (1H, s) | 1; 4; 5; 7; 7a |
7 | 153.7 | - | - | 158.0 | - | - |
7a | 144.0 | - | - | 151.0 | - | - |
8 | 61.0 | 3.74 (3H, s) | 5 | 57.0 | 3.79 (3H, s) | 7 |
9 | 11.5 | 2.13 (3H, s) | 3; 3a; 4; 5 | 11.0 | 1.95 (3H, s) | 3a; 4; 5 |
OH | - | 7.67 (1H, br s) | - | - | 10.59 (1H, br s) | 4; 6; 5 |
1’ | 179.1 | - | - | - | - | - |
2’ | 32.7 | 2.38-2.47 (2H, m) | 1’; 3’; 4’ | - | - | - |
3’ | 34.2 | 2.24-2.32 (2H, m) | 1’; 2’; 4’; 5’; 7’ | - | - | - |
4’ | 133.9 | - | - | - | - | - |
5’ | 123.0 | 5.23-5.28 (1H, m) | 3’; 7’ | - | - | - |
6’ | 22.3 | 3.37 (2H, br d; 6.8) | 5; 7; 5’ | - | - | - |
7’ | 16.1 | 1.78 (3H, s) | 3’; 4’; 5’ | - | - |
Abbreviations: s - singlet, br s - broad singlet, br d - broad doublet, m - multiplet.
*
gHMBC data set: the numbers correspond to the correlated carbons.
The 1H NMR spectrum of the mycophenolic acid (Figure 2)
showed signals for a methyl group at δ 1.78 (H-7', singlet, 3H) and a
methyl group linked to aromatic ring at δ 2.13 (H-9, singlet, 3H), a
signal for a methoxyl group at δ 3.74 (H-8, singlet, 3H), two signals
corresponding to aliphatic methylenes in the region of δ 2.47 to δ 2.38
(H-3a' and H-3b', multiplet 2H), of δ 2.32 to δ 2.24 (H-2', multiplet,
2H), a broad doublet for a methylene group at δ 3.37 (H-6', 2H), a broad
singlet at δ 5.18 (H-3, 2H) referring to an aliphatic methylene bearing
oxygen, and a multiplet for a methyne group of δ 5.23 to δ 5.28
(H-5',1H).http://www.scielo.br/scielo.php?pid=S0001-37652013000200487&script=sci_arttext
Anais da Academia Brasileira de Ciências
Print version ISSN 0001-3765
An. Acad. Bras. Ciênc. vol.85 no.2 Rio de Janeiro Apr./June 2013 Epub June 17, 2013
http://dx.doi.org/10.1590/S0001-37652013005000024
Angela M.M.P. ValenteI, Antonio G. FerreiraII, Cristina DaolioII, Edson Rodrigues FilhoIII, Elisangela F. BoffoIV, Antonia Q.L. SouzaV, Fernanda L.S. SebastianesVI, Itamar S. MeloI
ILaboratório de
Microbiologia Ambiental, Embrapa Meio Ambiente (CNPMA), Via SP 340, Km
127,5, Caixa Postal 69, 13820-000 Jaguariúna, SP, Brasil
IILaboratório
de Ressonância Magnética Nuclear and Laboratório de Microbiologia
Molecular e Espectroscopia de Massas, Departamento de Química,
Universidade Federal de São Carlos (UFSCar), Via Washington Luís, Km
235, Caixa Postal 676, 13565-905 São Carlos, SP, Brasil
IIILaboratório
de Microbiologia Molecular e Espectroscopia de Massas, Departamento de
Química, Universidade Federal de São Carlos (UFSCar), Via Washington
Luís, Km 235, Caixa Postal 676, 13565-905 São Carlos, SP, Brasil
IVDepartamento
de Química Orgânica, Instituto de Química, Universidade Federal da
Bahia (UFBA), Rua Barão de Geremoabo, 147, Campus Universitário de
Ondina, 40170-115 Salvador, BA, Brasil
VLaboratório
de Produtos de Origem Microbiana, Instituto de Ciências Biológicas/
ICB-DFCA, Universidade Federal do Amazonas (UFAM), Av. General Rodrigo
Octávio Jordão Ramos, 3000, Campus Universitário, Coroado I, 69077-000
Manaus, AM, Brasil
VIDepartamento
de Genética, Escola Superior de Agricultura ‘Luiz de Queiroz’,
Universidade de São Paulo (USP), Avenida Pádua Dias, 11, Caixa Postal
83, 13400-970 Piracicaba, SP, Brasil
In the 3JCH gHMBC experiment (Figure 4), H-3 correlated with C3a (δ 104.0), C4 (δ 110.0), C5 (δ 163.0), C7 (δ 158.0), C7a (δ151.0) and C1 (δ 173.0); H-6 correlated with C1, C4, C5, C7 and C7a; H-8 correlated with C3a, C4 and C5 and H-9 correlated with C7.
Figure 4
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