Chemical constituents from the stem of Brosimum potabile (Moraceae)

Abstract

Three coumarins, 5-methoxypsoralene, xanthyletin, and (-)-marmesin, have been isolated from the ethanolic extract of the stem of the Amazonian plant Brosimum potabile. The structures were determined on the basis of NMR analyses and by comparison with spectroscopic data in the literature. The analysis of the hexane fractions by GC-MS in EIMS mode suggested the presence of (1-methylpentyl)-benzene; α,α-dimethyl-4-(1-methylethyl)-benzenemethanol; 1-methyl-3,5-bis(1-methylethyl)-benzene; urs-12-ene; chola-5,22-dien-3β-ol; cholesta-4,6-dien-3β-ol; sitosteryl 9(Z)-octadecenoate; cholesta-5,22-dien-3β-ol; cholesta-4,6,22-trien-3-one; and cholesta-4,22-dien-3-one. NMR data of other hexane fractions indicated the presence of 3β-acetoxy-lup-12,20(29)-diene; 3β-acetoxy-olean-12-ene; 3β-acetoxy-urs-12-ene; and adian-5-ene. All these compounds are first described in B. potabile.KEYWORDS: Brosimum potabile, coumarins, pentacyclic triterpenes, structural characterization by NMR and GC/MS. Constituintes químicos do cerne de Brosimum potabile (Moraceae) RESUMOTrês cumarinas, 5-metoxipsoraleno, xantiletina e (-)-marmesina, foram isoladas no extrato etanólico do cerne da planta amazônica Brosimum potabile. Suas estruturas foram determinadas a partir das análises por RMN e por comparação com dados espectroscópicos da literatura. As análises das frações hexânicas por CG/EM sugeriram a presença de (1-metilpentil)-benzeno; α,α-dimetil-4-(1-metiletil)-benzenometanol; 1-metil-3,5-bis(1-metiletil)-benzeno; urs-12-eno; cola-5,22-dien-3β-ol; colesta-4,6-dien-3β-ol; (9Z)-octadecenoato de sitosterila; colesta-5,22-dien-3β-ol; colesta-4,6,22-trien-3-ona e colesta-4,22-dien-3-ona. Dados de RMN de outras frações hexânicas indicaram a presença de 3β-acetóxi-lup-12,20(29)-dieno; 3β-acetóxi-olean-12-eno; 3β-acetóxi-urs-12-eno e adian-5-eno. Todos esses compostos foram identificados pela primeira vez em B. potabile. PALAVRAS-CHAVE:Brosimum potabile, cumarinas, triterpenos pentacíclicos, caracterização estrutural por RMN e CG/EM.

α-Amylase and α-glucosidase inhibitory activities of the extracts and constituents of Ferulago blancheana, F. pachyloba and F. trachycarpa roots

“…The active dichloromethane extracts were subjected to column chromatography over silica gel and sephadex LH-20. As the result, eleven coumarins osthole (1) (Sajjadi et al, 2009), imperatorin (2) (Muller et al, 2004), bergapten (3) (Stevenson et al, 2003), prantschimgin (4) (Sajjadi et al, 2015), grandivitinol (5) (Abyshe et al, 1977), suberosin (6) (Tabanca et al, 2016), xanthotoxin (7) (Stevenson et al, 2003), felamidin (8) (Kilic et al, 2006), marmesin (9) (Abreu et al, 2010), umbelliferone (10) (Singh et al, 2010), ulopterol (11) (Doganca et al, 1979) and a sterol mixture consisted of stigmasterol (12), β-sitosterol (13) (Woldeyes et al, 2012) (Figure 1) were isolated and identified.…”