Secondary metabolites from Spirotropis longifolia (DC) Baill and their antifungal activity against human pathogenic fungi

A phytochemical study of the ethyl acetate extract of the roots and adventitious roots of Spirotropis longifolia, a monodominant tree species of the Guianan rainforest, has allowed the isolation of three compounds: 2- hydroxy-8,9-methylenedioxy-2',2'-dimethylpyrano-[5',6':4,3]-6a-prenyl-[6aS,11aS]-pterocarpan (spirotropin A), 2-hydroxy-8,9-methylenedioxy-2',2'-dimethy1-3',4'-dihydropyrano-[5',6':4,3]-6a-prenyl-(6aS,11aS]-pterocarpan (spirotropin B), and 5,7-dihydroxy-6.8-dipreny1-2 ''''.2 ''''-dimethylpyrano[5 '''',6 '''': 3',4]-isoflavone (spirotropone). In addition, 10 known compounds, trans-oxyresveratrol, trans-resveratrol, piceatannol, daidzein, genistein, isoprunetin, lupeol, latifolol, gnetin D and gnetin E, were also isolated. These compounds were evaluated for their antifungal activity and their cytotoxicity, and their structures were established by 1D and 2D NMR, HRMS, CD and optical rotation measurements. (C) 2011 Elsevier Ltd. All rights reserved.CNRS (France)CAPESCNPqFAPESPFAPDF (Brazil

Clusiaxanthone and tocotrienol Series from Clusia pernambucensis and their antileishmanial activity

Phytochemical analysis of the ethyl acetate extract from the stem bark of Clusia pernambucensis G. Mariz, Clusiaceae, a Brazilian Cerrado species, led to the isolation and full characterization of a new xanthone, 1,7-dihydroxy-2-(3-methyl-2-butenyl)-6',6'-dimethylpyrano(2',3':3,4)xanthone, namely clusiaxanthone. Four previously unreported tocotrienols from this species were also isolated. A derivative was obtained from clusiaxanthone, 1-hydroxy,7-methoxy-2-(3-methyl2-butenyl)-6',6'-dimethylpyrano(2',3':3,4)xanthone (7-O-methylclusiaxanthone), and an additional derivative was obtained from Z- δ -tocotrienoloic acid. The structures of these compounds were established based on data from ¹H and 13C nuclear magnetic resonance (1D and 2D NMR), high resolution electrospray ionization mass spectrometry (HRESIMS) and infrared spectroscopy. The clusiaxanthone and its derivative were able to control macrophage infection by Leishmania (Leishmania) amazonensis amastigotes (IC50 = 66.9 and 57.4 µM, respectively). The cytotoxicity of the compounds was assessed in BALB/c mouse peritoneal macrophages.A análise fitoquímica do extrato acetato de etila da casca do caule de Clusia pernambucensis G. Mariz, Clusiaceae, uma espécie do Cerrado brasileiro, conduziu ao isolamento e caracterização completa de uma nova xantona, 1,7-dihidróxi-2-(3-metil-2-butenil)-6',6'-dimetilpirano(2',3':3,4) xantona, denominada clusiaxantona. Quatro tocotrienóis ainda não relatados nesta espécie também foram isolados. Um derivado foi obtido a partir da clusiaxantona, 1-hidróxi,7-metóxi-2-(3-metil2-butenil)-6',6'-dimetilpirano(2',3':3,4)xantona (7-O-metil-clusiaxantona), e um segundo derivado foi obtido a partir do ácido Z- δ -tocotrienolóico. As estruturas foram estabelecidas com base em dados de ressonância magnética nuclear de ¹H e 13C (NMR 1D e 2D), espectrometria de massa com ionização por electrospray de alta resolução (HRESIMS) e espectroscopia no infravermelho. No controle da infecção de macrófagos com amastigotas de Leishmania (Leishmania) amazonensis, os compostos ativos foram clusiaxantona e seu derivado (CI50 = 66,9 e 57,4 µM, respectivamente). A citotoxicidade dos compostos foi determinada em macrófagos peritoneais de camundongos BALB/c

Residual Larvicidal Activity of Quinones against Aedes aegypti

The number of documented dengue cases has increased dramatically in recent years due to transmission through the Aedes aegypti mosquito bite. Vector control remains the most effective measure to protect against this and other arboviral diseases including Zika, chikungunya and (urban) yellow fever, with an established vaccine only available for yellow fever. Although the quinone class shows potential as leading compounds for larvicide development, limited information restricts the development of optimized structures and/or formulations. Thus, in this contribution we investigated the larvicidal and pupicidal activity of three quinone compounds isolated from a Connarus suberosus root wood ethyl acetate extract together with 28 quinones from other sources. Eight quinones demonstrated larvicidal activity, of which tectoquinone (4) proved to be the most active (LC50 1.1 µg/mL). The essential residual effect parameter of four of these quinones was evaluated in laboratory trials, with tectoquinone (4) and 2-ethylanthraquinone (7) presenting the most prolonged activity. In small-scale field residual tests, tectoquinone (4) caused 100% larvae mortality over 5 days, supporting its selection for formulation trials to develop a prototype larvicide to control Ae. aegypti

Development of gel with Matricaria recutita L. extract for topic application and evaluation of physical-chemical stability and toxicity

Matricaria recutita L. (Asteraceae), better known as chamomile, has been used due to its pharmacological properties. Laboratory-manufactured gels with chamomile extract were developed with the evaluation of the physical-chemical stability, as well as the study of its toxicity. The extractive solution was prepared by maceration with ethyl alcohol 95%. Part of the chamomile extractive ethanolic solution (CEES) was concentrated in rotoevaporator, obtaining a raw chamomile extract (RCE). For the preparation of gels, carbopol 940P, hydroxyethyl cellulose and hydroxypropyl methylcellulose were used with the addition of 3% and 5% chamomile extracts. The stability tests applied to the gels were as such: thermal stress, pH evaluation, viscosity and storage at different temperatures. In the end of the tests it was observed that the carbopol gel was the most stable. The Draize Test was employed as the toxicity test, with no irritation observed; however, on skin that underwent abrasion, some gels caused a little irritation.Colegio de Farmacéuticos de la Provincia de Buenos Aire

The wood preservative potential of long-lasting Amazonian wood extracts

Investigations were carried out on the efficacy of extracts from seven Amazonian woods (Bagassa guianensis, Manilkara huberi, Sextonia rubra, Vouacapoua americana, Andira surinamensis, Handroanthus serratifolius, and Qualea rosea) with varying natural durability to reduce soft-rot degradation in a 6-wk soil-bed test. Six of the wood extracts had shown efficacy against soft-rot fungi. In particular, the preservation efficacies of B. guianensis, H. serratifolius, and S. rubra extracts were highly significant up to retention levels of 23, 25, and 12 kg m?3, respectively. Three extracts (A. surinamensis, H. serratifolius, and Q. rosea) were then tested against Gloeophyllum trabeum (brown rot) and Trametes versicolor (white rot), in an agar-block test. H. serratifolius wood extract was very efficient at protecting P. sylvestris samples at 5.1 kg m?3 against the brown rot. This extract could be used as a basis for new wood protectant formulations. (Résumé d'auteur