New flavone from the leaves of Neea theifera (Nyctaginaceae)

Abstract

Neea theifera Oerst. (Nyctaginaceae) é amplamente utilizada na medicina popular brasileira para tratamento de úlceras gástricas e inflamação. A investigação fitoquímica das folhas de Neea theifera permitiu o isolamento e identificação da nova flavona luteolina-7-O-[2''-O-(5'''-O-feruloil)-β-D-apiofuranosil]-β-D-glucopiranosídeo(1) além dos oito compostos conhecidos vitexina, isovitexina, isoorientina, orientina, vicenina-2, crisoeriol, apigenina e luteolina. A identificação química foi realizada por métodos espectroscópicos incluindo RMN-2D, bem como análises no UV e IES-EM.Neea theifera Oerst. (Nyctaginaceae) is widely used in Brazilian folk medicine for the treatment of gastric ulcers and inflammation. Phytochemical investigation of the leaves of Neea theifera afforded the isolation of the new flavone luteolin-(1) besides the eight-known compounds vitexin, isovitexin, isoorientin, orientin, vicenin-2, chrysoeriol, apigenin and luteolin. Their chemical identification was established by NMR spectroscopic methods including 2D-NMR, as well as UV and ESI-MS analyses. IntroductionThe Nyctaginaceae family comprises around 300 species in 30 genera. 1 Phytochemical investigation with plants from this family is still scarce. Previous phytochemical studies of Boerhavia coccinea and B. erecta led to the isolation of tannins and saponins, 2 while B. diffusa yielded dihydroisofuranoxanthone, 3 rotenoids 4 and lignans. 5 Betacianins and flavonoids were isolated from Bougainvillea glabra, 6 already flavonoids and phenolic compounds were isolated from B. spectabillis. 7,8 Saponins were isolated from Colignonia scandens Benth. 9 and from Pisonia umbellifera. 10 In our search for bioactive natural products from São Paulo State, Brazil, we have examined the leaves of Neea theifera Oerst. This species is popularly known as 'Caparosa-do-campo' that grow wild in cerrado lands of Brazil. 1 They are used in folk medicine for the treatment of gastric ulcers and inflammation. 11 To the best of our knowledge, we could not find any previous phytochemical investigation with plants belonging to this genus.The present paper describes the isolation, purification and structure elucidation of the nine compounds from the leaves of N. theifera. Experimental Extraction and isolationThe dried leaves of N. theifera (953.5 g) were powdered and extracted successively with CHCl 3 and MeOH. The methanolic extract (3.0 g) was subjected to RP-C18 CC (40.0 cm × 2.5 i.d.) eluted with H 2 O:MeOH (9:1), H 2 O:MeOH (1:1) and MeOH giving 3 fractions: fr. 9:1 (1.8 g), fr. 1:1 (0.86 g) and fr. MeOH (0.34 g), 1133 Rinaldo et al. Vol. 18, No. 6, 2007 respectively. The fr. -58, 59-61, 66-68, 162-170, 190-206, 233-254 and 284-301 were identified as vitexin (12 mg), isovitexin (26 mg), orientin (16 mg), vicenin-2 (8 mg), chrysoeriol (5 mg), apigenin (4 mg) and luteolin (4 mg), respectively. Fraction 74-82 (60 mg) was further purified by semi-preparative HPLC and afforded to obtain pure isoorientin (6 mg) and pure compound (1) (8 mg). General experimental proce...

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