title: Chemical Composition, Antiprotozoal and Cytotoxic Activities of Indole Alkaloids and Benzofuran Neolignan of Aristolochia cordigera.
abstract: This is a comparative study on the intraspecific chemical variability ofAristolochia cordigeraspecies, 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, thein vitrosusceptibility of intracellular amastigote and promastigote forms ofLeishmania amazonensisto 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 againstPlasmodium falciparum, with an IC50value of 5 µM and a selectivity index higher than 50.
authors.affiliation: Instituto de Química, Universidade Estadual Paulista, Araraquara - SP, Brasil.
authors.forename: Marcos D P
authors.initials: MDP
authors.lastname: Pereira
authors.affiliation: Centro de Ciências Sociais, Saúde e Tecnologia, Universidade Federal do Maranhão, Imperatriz - MA, Brasil.
authors.forename: Tito
authors.initials: T
authors.lastname: da Silva
authors.affiliation: Instituto de Física de São Carlos, Universidade de São Paulo, São Carlos - SP, Brasil.
authors.forename: Anna Caroline C
authors.initials: ACC
authors.lastname: Aguiar
authors.affiliation: Instituto de Física de São Carlos, Universidade de São Paulo, São Carlos - SP, Brasil.
authors.forename: Glaucius
authors.initials: G
authors.lastname: Oliva
authors.affiliation: Instituto de Física de São Carlos, Universidade de São Paulo, São Carlos - SP, Brasil.
authors.forename: Rafael V C
authors.initials: RVC
authors.lastname: Guido
authors.affiliation: Instituto de Ciências Biomédicas, Universidade de São Paulo, São Paulo - SP, Brasil.
authors.forename: Jenicer K U
authors.initials: JKU
authors.lastname: Yokoyama-Yasunaka
authors.affiliation: Instituto de Ciências Biomédicas, Universidade de São Paulo, São Paulo - SP, Brasil.
authors.forename: Silvia R B
authors.initials: SRB
authors.lastname: Uliana
authors.affiliation: Instituto de Química, Universidade Estadual Paulista, Araraquara - SP, Brasil.
authors.forename: Lucia M X
authors.initials: LMX
authors.lastname: Lopes
mesh_terms: D000981:Antiprotozoal Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D030022:Aristolochia / Q000737:chemistry*; D001938:Brazil; D045744:Cell Line, Tumor; D003603:Cytotoxins / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D008401:Gas Chromatography-Mass Spectrometry; D006801:Humans; D026121:Indole Alkaloids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D007891:Leishmania / Q000187:drug effects; D017705:Lignans / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D010963:Plasmodium falciparum / Q000187:drug effects
chemical_list: D000981:Antiprotozoal Agents; D003603:Cytotoxins; D026121:Indole Alkaloids; D017705:Lignans; D010936:Plant Extracts