Alcaloides β-indolopiridoquinazolínicos de Esenbeckia grandiflora mart. (Rutaceae)

Abstract

Recebido em 29/7/08; aceito em 29/4/09; publicado na web em 6/10/09 INDOLOPYRIDOQUINAZOLINE ALKALOIDS FROM Esenbeckia grandiflora MART. (RUTACEAE). The chemical composition of two specimens of Esenbeckia grandiflora, collected in the south and northeast regions of Brazil, was investigated. In this study, three β-indolopyridoquinazoline alkaloids from the leaves (rutaecarpine, 1-hydroxyrutaecarpine) and roots (euxylophoricine D) were isolated for the first time in this genus. In addition, the triterpenes a-amyrin, β-amyrin, a-amyrenonol, β-amyrenonol, 3a-hydroxyursan-12-one, and 3a-hydroxy-12,13-epoxy-oleanane, the coumarins auraptene, umbelliferone, pimpinelin, and xanthotoxin, the furoquinoline alkaloids delbine and kokusaginine, and the phytosteroids sitosterol, stigmasterol, campesterol and 3β-O-β-Dglucopyranosylsitosterol were also isolated from the leaves, twigs, roots and stems of this species. Structures of these compounds were established by spectral analysis.

Toxicity of plant extracts from Bahia, Brazil, to Atta sexdens sexdens workers (Hymenoptera: Formicidae)

“…The toxicity of C. sylvestris extracts to leaf cutting ants may be due to its diterpenes, class of substances compounds with biological activities, including antifungal effect (Bento et al, 2013). The alkaloids (Januário et al, 2009) and coumarins from E. grandiflora were toxic to Aedes aegypti larvae (Oliveira et al, 2005). Leaf and branch extracts from Z. rhoifolium presented contact and ingestion toxicity to leaf cutting ants.…”

Quinoline alkaloids and friedelane-type triterpenes isolated from leaves and wood of Esenbeckia alata kunt (Rutaceae)

“…20 HMBC and HMQC spectra confirmed the location of the isoprenyl and carbonyl groups. Information provided by 1 H and 13 C NMR spectra led to determine the presence of a quinoline alkaloid, named as 4-methoxy-3-(3'-methyl-but-2'-enyl)-N-methyl-quinolin-2(1H)-one. H NMR spectra of those compounds showed similar profiles including signals at δ H ca 7.5 (d, J ≈ 2.5 Hz, 1H) and δ H ca 6.9 (d, J ≈ 2.5 Hz, 1H), for vinyl protons at furan ring.…”

“…Differences among them were stablished through NMR spectra according to the presence of a methoxy groups signals, whose location was defined by HMBC experiments. According to the above-mentioned information obtained from 1 H and 13 C NMR (one-and two-dimensional), on comparing spectroscopic data with the literature, 23 compounds 3-6 were identified as furoquinoline alkaloids dictamine, kokusaginine, γ-fagarine, and flindersiamine, respectively, which had been previously isolated from Rutaceae specimens such as Boronia pinnata, Dictamnus (9), whose analyses of both NMR and optical rotation data, in comparison with reported data in literature, 14 allowed establishing the configuration showed in Figure 1 for 7-9. Compounds 7 and 8 have been previously identified in E. litoralis.…”

“…Vacuum column chromatography (VCC) was developed with silica gel 60 G, Merck. 1 H NMR (400 MHz) and 13 C NMR (100 MHz) spectra were recorded on a Bruker Avance 400 using TMS as internal standard, in deuterated chloroform (CDCl 3 ) as solvent. High Resolution Mass spectra (HRMS) were determined on a Shimadzu IT-ToF spectrometer (with an ESI source and in the positive ion mode), and electron impact mass spectra (IEMS) were recorded in a Jeol JMS-SX102A spectrometer.…”

New nitro-benzo[c]phenanthridine and indolopyridoquinazoline alkaloids from Zanthoxylum atchoum

“…The UV spectrum showed absorptions bands at 250, 330 and 380 nm, with a bathochromic shift observed in alkaline medium at 417 nm, suggesting the presence of a phenol group. The All these data readily help us to identify a typical 7, 8-dihydropyridoquinazoline nucleus [10,11]. The 13 C-NMR spectrum of 3 showed 19 carbon signals due to eight quaternary carbons, seven methines, two methylenes, Nmethyl and carbonyl groups.…”