A New Aromatic Nitrosulfone from Cardiospermum corindum

Abstract

Dried leaves of Cardiospermum corindum yielded two, novel-type aromatic nitrosulfones [1,2]. The structures were established by spectroscopic analyses and synthesis.Compounds 1 and 2 were assigned the structures, 1-methyl-4-{ [2-(4-nitrophenyl) ethenyl } sulfonyl benzene and 1-{ [2-methoxy-2-(4-nitrophenyl) ethyl] sulfonyl } 4-methyl benzene, respectively.Morphologically, the climber Cardiospermum corindum L. (Sapindaceae) reflects spectacular adaptive diversities of development of yellow-tinged petals with supra basal scales presumably designed to favor cross pollination. The inflated fruit and worm-like seed with cordate hylum are advantageous for seed dispersal (1,2). Recently, this plant has attracted the attention of phytochemists (3-7). The present study is an attempt to discover new chemical compounds to match the relatively advanced morphology of the genus.Dried leaves of C. corindum collected near Tirupati, Chittoor District, Andhra Pradesh, India, were successively extracted with petrol, C6H6, and Me2CO. Five subsequent MeOH extracts each deposited a solid on cooling, which resulted in the isolation (see Experimental) of 3' ,4 '-di-0-methylluteolin-7^-D-gIucuronide (8), an orange compound [1], and, finally, a light yellow, crystalline product [2].The orange compound, according to eims, possessed the composition C15H13N04S. The compound had no optical activity. The ir spectrum displayed strong bands at 1340 and 1510 cm-1, as well as at 1140 and 1320 cm"1, indicative of the presence of -N02 and -S02 groupings, respectively. The 'H-nmr and 13C-nmr spectra suggested that the compound 1 was l-methyl-4-{ [2-(4 nitrophenyl) ethenyl} sulfonyl } benzene. This formulation was supported by the base peak fragment at m!z 139 (Me.C6H4.SO+) in the ms. On electron impact,/>-tolyl vinyl sulfones are known to undergo predominantly vinyl migration to oxygen with subsequent cleavage of the sulfur oxygen bond (9).

Identificação de alguns constituintes químicos de Indigofera hirsuta Linn. (Fabaceae) por CLAE-IES-EM (TOF) e avaliação da atividade antirradicalar

“…[23][24][25] Para avaliar a atividade sequestradora de radicais livres foi utilizada uma solução 0,04 mg mL -1 de DPPH em metanol. Foram adicionados 2 mL desta solução a 1 mL da solução de cada amostra em diferentes concentrações (5,10,20,40, 80 e 160 μg mL -1 ). Após 30 min foram medidas as absorbâncias das soluções resultantes em 517 nm.…”

Chemical constituents of Cardiospermum corindum L. and their distribution in Sapindaceae

“…Previous phytochemical studies of C. corindum revealed the presence of 3 0 ,4 0 -di-O-methyl luteolin-7-b-D-glucuronide (Adinarayana and Sarada, 1989;Rao et al, 1992), myo-inositol (Adinarayana and Sarada, 1989), 1-methyl 4-{[2-(4-nitrophenyl) ethenyl] sulfonyl}benzene, 1-{[2-methoxy-2 (4-nitrophenyl) ethyl] sulfonyl} 4-methyl-benzene (Adinarayana et al, 1987), b-sitosterol and stigmasterol (Adinarayana and Sarada, 1989).…”