Chemical constituents from Chirita longgangensis var. hongyao with inhibitory activity against porcine respiratory and reproductive syndrome virus

Abstract

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...

Chemical constituents of Chirita halongensis Kiew & T.H.Nguyen collected in Ha Long Bay, Quang Ninh province, Viet Nam

“…The spectroscopic data suggested that 2 belong to the urs-12-en-28-oic acid series. This suggestion confirmed by 1 The α configuration of hydroxy group at C-3 was identified by the chemical shift and multiplicity of hydroxy-methine proton. Consequently, 2 was determined as 3 ,24-dihydroxy-urs-12-en-28-oic acid by comparison with spectroscopic data in literature.…”

“…Chirita is the oldest genus of the Gesneriaceae family, distributed in Malaysia, Southeast Asia and south of China. Some Chirita species are used in folk medicine as poultice, hemostasis agents or for treatment of hypertension, .... [1] There are about 20 Chirita species in Vietnam. [2] Until now, there have been only a few studies on chemical and biological activities of the Chirita species, but they revealed interesting results.…”

Chemical Constituents of Chirita drakei

“…Supplementary data: 1 H and 13 C NMR spectra and HR-MS spectra of all isolated compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14), 2D NMR spectra of the new compounds 1 and 2, NMR data of the acetylated derivative 2a.…”

“…Based on molecular phylogenetic investigations Chirita was recently recognized as an artificial, polyphyletic genus and therefore reorganized transferring parts of the genus to Primulina [2]. In the folk medicine, some Chirita species are used for the treatment of bone fractures, wounds, pains, arthritis and anemia [3]. Previous phytochemical studies on other Chirita species revealed mainly phenylethanoid glycosides, flavonoids and quinines [4][5][6][7][8].…”