Solanidane and iminosolanidane alkaloids from Solanum campaniforme
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Data
2013-09-27
Autores
Torres, Maria Conceição M.
Jorge, Roberta Jeane B.
Ximenes, Rafael M.
Alves, Natacha Teresa Q.
Santos, João Victor de A.
Marinho, Aline D.
Monteiro, Helena S.A.
Toyama, Marcos H.
Braz-Filho, Raimundo
Silveira, Edilberto R.
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Resumo
From the leaves of Solanum campaniforme (Solanaceae), eight solanidane alkaloids were isolated, four of which contain a p-hydroxyphenylethylamine unit. Their structures were established as: 22β,23β-epoxy-solanida-1,4-dien-3-one; 22α,23α-epoxy-10-epi-solanida-1,4,9-trien-3-one; 22α,23α-epoxy-solanida-4-en-3-one; 22β,23β-epoxy-solanida-4-en-3-one; (E)-N-[8′(4-hydroxyphenyl)ethyl]-22α,23α-epoxy-solanida-1,4,9-trien-3-imine; (E)-N-[8′(4-hydroxyphenyl)ethyl]-22α,23α-epoxy-solanida-1,4-dien-3-imine; (Z)-N-[8′(4-hydroxyphenyl)ethyl]-22α,23α-epoxy-solanida-1,4,9-trien-3-imine and (Z)-N-[8′(4-hydroxyphenyl)ethyl]-22α,23α-epoxy-solanida-1,4-dien-3-imine. All structures were determined using spectroscopic techniques, such as 1D and 2D NMR, and HRESIMS. The cytotoxicity and the antiophidic activities of the alkaloids were evaluated. The alkaloids did not show any cytotoxicity, but inhibited the main toxic actions of Bothrops pauloensis venom. © 2013 Elsevier Ltd. All rights reserved.
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Bothrops pauloensis, Iminosolanidane alkaloids, Solanaceae, Solanidane alkaloids, Solanum campaniforme
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Phytochemistry.