Solanidane and iminosolanidane alkaloids from Solanum campaniforme.
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.
Departamento de Química Orgânica e Inorgânica, Universidade Federal do Ceará, 12.200, Fortaleza-CE 60.021-970, Brazil.
Maria Conceição M
MC
Torres
Roberta Jeane B
RJ
Jorge
Rafael M
RM
Ximenes
Natacha Teresa Q
NT
Alves
João Victor de A
JV
Santos
Aline D
AD
Marinho
Helena S A
HS
Monteiro
Marcos H
MH
Toyama
Raimundo
R
Braz-Filho
Edilberto R
ER
Silveira
Otília Deusdênia L
OD
Pessoa
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001938:Brazil; D003435:Crotalid Venoms / Q000037:antagonists & inhibitors; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000737:chemistry; D032322:Solanum / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D003435:Crotalid Venoms
Bothrops pauloensis; Iminosolanidane alkaloids; Solanaceae; Solanidane alkaloids; Solanum campaniforme