Chemical constituents of Aristolochia giberti

Abstract

Foram isoladas quatorze substâncias de Aristolochia giberti, entre elas, um novo triterpeno, (-)-onocera-8,8'-diol. Além destas, 3-hidróxipropanoato, acetato e formato foram detectados por técnicas de RMN, o que sugere que estas substâncias sejam derivadas do 2-butinodioato, não detectável por RMN de 1 H. As análises dos óleos essenciais de caules e folhas, por CG-EM e quimiometria, mostraram grande similaridade entre as espécies cultivadas no Brasil e aquelas na Argentina, o que permitiu confirmar a identificação da espécie e diferenciar os óleos de acordo com as partes da planta.Fourteen compounds were isolated from Aristolochia giberti. These included a new triterperne, (-)-onocera-8,8'-diol. In addition, 3-hydroxypropanoate, acetate, and formate were detected by NMR techniques, which suggests that they are derivatives from 2-butynedioate, which is not detected by 1 H NMR. GC-MS and chemometric analyses of essential oils from stems and leaves showed great similarity between this cultivated species in Brazil and that in Argentina, which allowed us to confirm the species identity and to differentiate the oils according to the plant parts. IntroductionAristolochia species (Aristolochiaceae) are generally sold at Brazilian markets under their popular names, particularly as "One Thousand Man", and little distinction has been made among the species. They have been mainly used in Brazilian traditional medicine as abortifacients, stomachics, antiophidians, antiasthmatics, and expectorants, and recently in slimming therapies.1,2 Aristolochic acids constitute a class of compounds that are characteristic of the Aristolochia genus. These acids have been associated with Chinese herb nephropathy, which is a kind of severe kidney disease caused by the intake of excessive aristolochic acids.3 Therefore, it is essential, for health safety and quality control of related Brazilian herbal medicines, to know the chemical composition of these species, among them Aristolochia giberti Hook., and to develop efficient methods for species identification.The chemical constituents of Brazilian Aristolochiaceae species, such as lignans, have shown antiplasmodial, 4 antimycobacterial, 5 insecticidal, 6,7 anti-inflammatory, and analgesic activities. Despite the significant number of Brazilian Aristolochia species (around 100), the volatile compounds they contain are known for only a few species. 9 In our previous studies on essential oils from roots of 10 Aristolochia species, we investigated the oil composition and correlated them to morphological groups by GC-MS and chemometric analyses, which could also help in the identification of these species. 9A total of 64 compounds were identified in the analysed essential oils from stems and leaves of A. giberti collected in Argentina and Paraguay, which corresponded to around 77% to 92% of the constituents in the oils.10,11 Methanolic extracts of A. giberti protected against enzymatic and non-enzymatic lipid peroxidation in microsomal membranes of rat. 12The goals of the present study were to in...

Seasonal Variation, Chemical Composition, and Analgesic and Antimicrobial Activities of the Essential Oil from Leaves of Tetradenia riparia (Hochst.) Codd in Southern Brazil

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Extractives of the tropical wood wallaba (Eperua falcata Aubl.) as natural anti-swelling agents

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Cytotoxicity and the bioconversion strategy of Aristolochia spp.

“…Nearly fifty compounds have been reported to occur in A. triangularis, among which only aristolactam I and aristolochic acids I, II, C and D, all of which are cytotoxic, were detected in leaves of this species (SILVA et al, 2019;MICHL et al, 2016). In contrast, a total of twelve chemical constituents, including the cytotoxic lignans cubebin, (-)-hinokinin, and (-)-kusunokinin, have been isolated from A. gibertii leaves (MARCHESINI et al, 2009). As expected, the fecal extracts were not considered cytotoxic, which supported the hypothesis of this study that bioconversion by B. polydamas larvae would be an efficient way to obtain Aristolochiaceous extracts with minimal to no toxicity.…”