1. Synthesis and biological activity evaluation of lignan lactones derived from (-)-cubebin
- Author
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Vanessa Aparecida Feijó de Souza, Vanesa de A. Royo, Ana Lúcia Santos de Matos Araújo, Márcio Luis Andrade e Silva, Ademar Alves da Silva, Rosangela da Silva, Paulo Marcos Donate, Jairo Kenupp Bastos, Ana C. Pereira, José Carlos Tavares Carvalho, and Gustavo Henrique Bianco de Souza
- Subjects
Pain Threshold ,Stereochemistry ,Clinical Biochemistry ,Nitro compound ,Anti-Inflammatory Agents ,Pharmaceutical Science ,Pharmacology ,Biochemistry ,Chemical synthesis ,Lignans ,chemistry.chemical_compound ,Lactones ,Edema ,Drug Discovery ,medicine ,Animals ,Hot plate test ,Molecular Biology ,Lignan ,chemistry.chemical_classification ,Analgesics ,Dose-Response Relationship, Drug ,Organic Chemistry ,Biological activity ,Rats ,Dose–response relationship ,chemistry ,Molecular Medicine ,medicine.symptom ,Lactone - Abstract
The anti-inflammatory and analgesic effects of three dibenzylbutyrolactone lignans, (-)-hinokinin (2), (-)-6,6'-dinitrohinokinin (3), and (-)-6,6'-diaminohinokinin (4), obtained by partial synthesis from (-)-cubebin (1), were investigated using different animal models. It was observed that compounds (1) and (2) inhibited the edema formation in the rat paw edema assay at the same level and that all responses were dose dependent. Also, at the dose of 30 mg/kg, compounds 1, 2, 3, and 4 inhibited the edema formation by 53%, 63%, 54%, and 82%, respectively, at the third hour of the experiment. In the acetic acid-induced writhing test in mice, compounds 2 and 4 produced inhibition levels of 97% and 92%, respectively, while 3 displayed lower effect (75%), which was still higher than 1. The assayed compounds neither displayed activity in the cell migration test nor in the hot plate test.
- Published
- 2004