Dois novos quinenóides chiritalona A and B, e uma nova neolignina 7'E-4,9-dihidroxi-3,3',5'-trimethoxi-8,4'-oxineolign-7'-en-9'-al, além dos conhecidos (-)-8-hidroxi-α-dunniona, digiferruginol, 2,5-dimetoxi-1,4-benzoquinona e hederagenina, foram isolados do caule de Chirita longgangensis var. hongyao. As estruturas dos novos compostos foram elucidadas por análise detalhada de dados obtidos pela técnicas de NMR (ressonância magnética nuclear) e MS (espectrometria de massas), e a configuração absoluta de chiritalona A foi determinada por análise de difração de raios X de monocristal utilizando o parâmetro Flack. A atividade inibitória dos compostos com relação ao vírus da síndrome respiratória e reprodutiva suína (PRRSV) foi medida pelo método do efeito citopático (CPE). Digiferruginol e hederagenina apresentaram efeito fraco com relação ao PRRSV com valor IC 50 de 80,5 ± 16,9 μmol L -1 (SI = 19,9) e 43,2 ± 7,4 μmol L -1 (SI = 13,1), respectivamente.Two new quinonoids chiritalone A and B, and a new neolignan 7'E-4,9-dihydroxy-3,3',5'-trimethoxy-8,4'-oxyneolign-7'-en-9'-al, along with known (-)-8-hydroxy-α-dunnione, digiferruginol, 2,5-dimethoxy-1,4-benzoquinone and hederagenin, were isolated from the stems of Chirita longgangensis var. hongyao. The structures of the new compounds were elucidated by detailed analysis from NMR (nuclear magnetic resonance) and MS (mass spectrometry) data, and the absolute configuration of chiritalone A was determined by single crystal X-ray diffraction analysis using the Flack parameter. The inhibitory activity of compounds against porcine respiratory and reproductive syndrome virus (PRRSV) was measured by the cytopathic effect (CPE) method. Digiferruginol and hederagenin showed weak effect on PRRSV with an IC 50 value of 80.5 ± 16.9 μmol L -1 (SI = 19.9) and 43.2 ± 7.4 μmol L -1 (SI = 13.1), respectively. Keywords: Gesneriaceae; Chirita longgangensis var. hongyao, quinines, porcine reproductive and respiratory syndrome virus
IntroductionPorcine reproductive and respiratory syndrome (PRRS), caused by porcine reproductive and respiratory syndrome virus (PRRSV), is characterized by respiratory disorders in young pigs and reproductive failure in sows. It is widespread in most major pig-producing areas throughout the world and is one of the most important causes of economic loss to the swine industry. In China, in 2006 only, PRRS spread to more than 10 provinces (or autonomous regions) and affected over 2,000,000 pigs with about 400,000 fatal cases. 1 Although previous studies provided a basis for development of pharmacological agents to inhibit PRRSV replication, so far there are no effective drugs to overcome this problem, 2 and many vaccine strategies developed to control the disease are not yet completely successful. 3,4 Quinones are a widespread group of oxygen-substituted aromatic compounds, and some of them are considered Chemical Constituents from Chirita longgangensis var. hongyao with Inhibitory Activity against PRRSV J. Braz. Chem. Soc. 1926 as inhibitory agents against bo...