Anti-Inflammatory Meroterpenoids of Cordia glazioviana (Boraginaceae)

Journal of the Brazilian Chemical Society

article

Silva, Ana Karine O.¹  Pinto, Francisco C. L.¹  Canuto, Kirley M.²  Braz-Filho, Raimundo³  Silva, Rose Anny C.⁴  Santos, Flávia A.⁵  Monteiro, Norberto K. V.⁶  Silveira, Edilberto R.¹  Pessoa, Otília D. L.¹ 

[1] Departamento de Química Orgânica e Inorgânica, Universidade Federal do Ceará;Embrapa Agroindústria Tropical;Departamento de Química, Universidade Estadual do Norte Fluminense Darcy Ribeiro;Departamento de Medicina Clínica, Universidade Federal do Ceará;Departamento de Fisiologia e Farmacologia, Universidade Federal do Ceará;Departamento de Química Analítica e Fisico-Química, Universidade Federal do Ceará

关键词: Cordia glazioviana;    Boraginaceae;    hydroquinones;    naphthoquinones;    antiinflammatory activity;   

DOI  :  10.21577/0103-5053.20210041

学科分类：内科医学

来源: SciELO

【 摘 要 】

The phytochemical reinvestigation from the heartwood of the extracts of Cordia glazioviana led to the isolation of four still undescribed hydroquinones derivatives designated as cordiaquinol D ( 1 ), cordiaquinol E ( 2 ), (10 R )-10,11-dihydrofuran-1,4-dihydroxy-globiferin ( 3 ) and 2-[(1’ E ,6’ E )-3’,8’- dihydroxy-3’,7’-dimethylocta-1’,6’-dienyl]-benzene-1,4-diol ( 4 ), along with the naphthoquinone 6-[(2’ R )-2’-hydroxy-3’,6’-dihydro-2 H -pyran-5’-yl]-2-methoxy-7-methylnaphthalene-1,4-dione ( 5 ). Additionally, six previously known compounds were also isolated: rel -1,4-dihydroxy-8(,11(;9(,11(-diepoxy-2-methoxy-8a(-methyl-5,6,7,8,8a,9,10,10a-octahydro-10-antracenone ( 6 ), didehydroconicol ( 7 ), 1(,6(-dihydroxy-7- epi -eudesm-3-ene ( 8 ), 1(,6(-dihydroxy-7- epi -eudesm-4(15)-ene ( 9 ), 10,11-dihydroxybisabolol ( 10 ), and hamanasal-A ( 11 ). The structures of the new compounds were assigned by high-resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR) analyses. The relative stereochemistry of 3, 4 , and 5 was improved by quantum mechanical calculations. Eight, out of the eleven isolated compounds ( 2-9 ), were tested through cellular viability and lipopolysaccharide (LPS)-induced inflammation assays against RAW 264.7 macrophage-like cells. Compounds 3-5 exhibited a stronger effect on LPS-induced NO production (half-maximal inhibitory concentration (IC 50 ) 50.34, 105.83, and 66.73 µM, respectively).

【 授权许可】

CC BY