Chemical constituents from the heartwood of Haematoxylon campechianum as protein tyrosine kinase inhibitors.
In a previous study, we showed that a series of homoisoflavonoids from the stems of Haematoxylon campechianum possess potent protein tyrosine kinase inhibitory activity. In a further chemical investigation of the heartwood of H. campechianum, three new homoisoflavonoids, epihematoxylol B (2), 10-O-methylhematoxylol B (3), and 10-O-methylepihematoxylol B (4), were isolated and identified, together with 15 known compounds, including three homoisoflavonoids, three flavonoids, six lignans, and three unsaturated fatty acids. The structures of the new compounds were established on the basis of 1D- and 2D-NMR and other spectroscopic analyses. Using ELISA method, the new compounds and selected known compounds were tested for protein tyrosine kinase inhibitory activity targeting kinase insert domain receptor. Epihematoxylol B (2) and the known compounds, hematoxylol B (1) and hematoxylin (5), exhibited inhibitory rates of 92.22.3, 71.31.1, and 94.81.6, respectively, at 10 μM concentration.
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu-Chong-Zhi Road, Zhangjiang Hi-tech Park, Shanghai 201203, P. R. China; State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Av. Padre Tomás Pereira, Taipa, Macao, P. R. China, (phone: +853-83974873; fax: +853-28841358). ligenl@umac.mo.
Li-Gen
LG
Lin
Hua
H
Xie
Yi-Tao
YT
Wang
Jian
J
Ding
Yang
Y
Ye
D007887:Fabaceae / Q000737:chemistry*; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D017705:Lignans / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D018547:Plant Stems / Q000737:chemistry; D047428:Protein Kinase Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D011505:Protein-Tyrosine Kinases / Q000037:antagonists & inhibitors* / Q000378:metabolism
D005419:Flavonoids; D017705:Lignans; D047428:Protein Kinase Inhibitors; D011505:Protein-Tyrosine Kinases
Epihematoxylol B; Haematoxylon campechianum; Hematoxylol B, 10-O-methyl-; Homoisoflavonoids; Kinase insert domain receptor (KDR); Protein tyrosine kinases (PTKs)