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Planta Med 2017; 83(11): 912-920
DOI: 10.1055/s-0043-104776
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Chemical Composition, Antiprotozoal and Cytotoxic Activities of Indole Alkaloids and Benzofuran Neolignan of Aristolochia cordigera

Marcos D. P. Pereira
1   Instituto de Química, Universidade Estadual Paulista, Araraquara – SP, Brasil
,
Tito da Silva
2   Centro de Ciências Sociais, Saúde e Tecnologia, Universidade Federal do Maranhão, Imperatriz – MA, Brasil
,
Anna Caroline C. Aguiar
3   Instituto de Física de São Carlos, Universidade de São Paulo, São Carlos – SP, Brasil
,
Glaucius Oliva
3   Instituto de Física de São Carlos, Universidade de São Paulo, São Carlos – SP, Brasil
,
Rafael V. C. Guido
3   Instituto de Física de São Carlos, Universidade de São Paulo, São Carlos – SP, Brasil
,
Jenicer K. U. Yokoyama-Yasunaka
4   Instituto de Ciências Biomédicas, Universidade de São Paulo, São Paulo – SP, Brasil
,
Silvia R. B. Uliana
4   Instituto de Ciências Biomédicas, Universidade de São Paulo, São Paulo – SP, Brasil
,
Lucia M. X. Lopes
1   Instituto de Química, Universidade Estadual Paulista, Araraquara – SP, Brasil
› Author Affiliations
Further Information

Publication History

received 17 November 2016
revised 08 February 2017

accepted 19 February 2017

Publication Date:
06 March 2017 (online)

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Abstract

This is a comparative study on the intraspecific chemical variability of Aristolochia cordigera species, collected in two different regions of Brazil, Biome Cerrado (semiarid) and Biome Amazônia (coastal). The use of GC-MS and statistical methods led to the identification of 56 compounds. A higher percentage of palmitone and germacrene-D in the hexanes extracts of the leaves of plants from these respective biomes was observed. Phytochemical studies on the extracts led to the isolation and identification of 19 known compounds, including lignans, neolignans, aristolochic acids, indole-β-carboline, and indole alkaloids. In addition, two new indole alkaloids, 3,4-dihydro-hyrtiosulawesine and 6-O-(β-glucopyranosyl)hyrtiosulawesine, were isolated and a new neolignan, cis-eupomatenoid-7, was obtained in a mixture with its known isomer eupomatenoid-7. Their structures were determined by spectroscopic methods, mainly by 1D- and 2D-NMR. The occurrence of indole alkaloids is being described for the first time in the Aristolochiaceae family. Moreover, the in vitro susceptibility of intracellular amastigote and promastigote forms of Leishmania amazonensis to the alkaloids and eupomatenoid-7 were evaluated. This neolignan exhibited low activity against promastigotes (IC50 = 46 µM), while the alkaloids did not show inhibitory activity. The new alkaloid 6-O-(β-glucopyranosyl)hyrtiosulawesine exhibited activity in the low micromolar range against Plasmodium falciparum, with an IC50 value of 5 µM and a selectivity index higher than 50.

Key words

Aristolochia cordigera - Aristolochiaceae - neolignans - indole alkaloids - antiplasmodial - antileishmanial

Supporting Information

Data of scores and loading for principal components (PCs) and yields of the hexane extracts, IR, UV, HRMS, 1D and 2D NMR spectra of 20 and 21, and 1H NMR spectra of 1 and 22, along with the dose-response curves of compounds 19 and 21 against P. falciparum, and of compound 1 against promastigotes of L. amazonensis, are available as Supporting Information.

 

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