Activities of extracts and compounds from Spiranthera odoratissima St. Hil. (Rutaceae) in leaf-cutting ants and their symbiotic fungus

Abstract

O estudo dos extratos dos galhos da planta Spiranthera odoratissima St. Hil. (Rutaceae) levou ao isolamento de alcalóides furoquinolínicos (dictamina, g-fagarina e esquimianina) e 2-arilquinolin-4-ona (2-fenil-1-metilquinolin-4-ona) e limonóides (ácido limonéxico e limonina). Os compostos 2-fenil-1-metilquinolin-4-ona e ácido limonéxico foram isolados pela primeira vez no gênero Spiranthera. Os alcalóides furoquinolínicos, 2-arilquinolin-4-ona e os limonóides mostraram atividade inseticida e/ou fungicida no ninho da formiga Atta sexdens rubropilosa.The study of the Spiranthera odoratissima St. Hil (Rutaceae) branches extracts led to the isolation of the furoquinoline (dictamine, g-fagarine and skimmianine) and 2-arylquinoli-4-one (1-methyl-2-phenylquinolin-4-one) alkaloids and limonoids (limonexic acid and limonin). The compounds 1-methyl-2-phenylquinolin-4-one and limonexic acid were isolated for the first time from the Spiranthera. These furoquinoline and 2-arylquinoli-4-one alkaloids and limonoids showed insecticidal and/or fungicidal activity in the nest of the Atta sexdens rubropilosa. Keywords: Spiranthera odoratissima, furoquinoline alkaloids, limonoids, Atta sexdens rubropilosa, Leucoagaricus gongylophorus IntroductionSpiranthera odoratissima St. Hil. (Rutaceae), popularly know as Manacá, is a shrub found in the savannah and forest of Central Brazil, and in Bolivia.1 In folk medicine is used in the treatment of rheumatism, gout, kidney infections, urinary retention, abdominal pains, acne and boil.2 According to Matos et al.,3 the ethanolic extract of the S. odoratissima roots contain compounds with analgesic and anti-inflammatory activity.In previous phytochemical studies of S. odoratissima roots and leaves were reported to contain furoquinoline and b-indoloquinazoline alkaloids, coumarin, terpene, steroid and limonoids. [4][5] Leaf-cutting ants (Hymenoptera) are dominant herbivores in the tropics and can be found from the United States Southern to Northern Argentina countries.6 They cultivate a symbiotic fungus for feeding using leaf fragments as substrate, thus they are considering plague.7 Therefore, the biological control of these insects has been the aim of many studies.In this work was determined the toxicity of crude extract and compounds isolated from S. odoratissima branches in nest of the Atta sexdens rubropilosa. Experimental General experimental proceduresThe 1 H NMR, 13 C NMR and 2D correlations spectra were obtained using Bruker DRX-400 spectrometer, with CDCl 3 and acetone-d 6 using TMS as internal standard. Terezan et al. 883 Vol. 21, No. 5, 2010 For ESIMS analysis, low resolution, was used on triple quadrupole Micromass Quattro LC instrument. GC/MS (EI) analysis was used a QP5000 Shimadzu, capillary column DB 5MS (30 m, 0.25 mm id, film 0.25 mm). The temperature was programmed initially at 70 °C for 4 min, them increased with a rate of 10 °C min -1 to 280 °C respectively, injection volume was 1 mL in a split mode and temperatures of the detector/ injector were 300 /280 °C. The mass...

Melanogenesis‐Inhibitory and Cytotoxic Activities of Limonoids, Alkaloids, and Phenolic Compounds from Phellodendron amurense Bark

“…7.5% based on the amount isolated. [37] The structure of a new compound, 13, was elucidated on the basis of spectroscopic analysis and comparison with a known compound, 12, [39] as described below. Occurrence of these compounds has been reported in the other Rutaceae plants.…”

Screening of native plants from central Argentina against the leaf-cutting ant Acromyrmex lundi (Guérin) and its symbiotic fungus

“…However, very few studies have simultaneously addressed the effects of plant extracts on ants and fungi, and they have generally dealt with a single plant extract. Thus, deleterious effects of Ricinus communis (Euphorbiaceae), Simarouba versicolor (Simaroubaceae) and Spiranthera odoratissima (Rutaceae) on the leaf-cutting ant Atta sexdens L. and its symbiotic fungus, have been recorded (Bigi et al, 2004;Peñaflor et al, 2009;Terezan et al, 2010) with other authors testing seed oil from three citrus species on a similar ant-fungus system (Fernandes et al, 2002).…”

Estudo farmacognóstico de folhas e raízes da Spiranthera odoratissima A. St.-Hil. (Rutaceae)

“…Ribeiro et al (2005) isolaram das raízes de Spiranthera odoratissima, além da limonina, dois novos limonoides, três alcaloides furoquinolínicos (dictamina, γ-fagarina e esquimianina), três alcaloides β-indoloquinazolínicos (rutaecarpina, evodiamina e 1-hidroxirutaecarpina), a cumarina aurapteno e o β-sitosterol. Terezan et al (2010) isolaram dos galhos de S. odoratissima os alcaloides furoquinolínicos (dictamina, γ-fagarina e esquimianina) e 2-arilquinolin-4-ona (2-fenil-1-metilquinolin-4-ona) e limonoides (ácido limonéxico e limonina). Os alcaloides furoquinolínicos, 2-arilquinolin-4-ona e os limonoides mostraram atividade inseticida e/ou fungicida para o ninho da formiga Atta sexdens rubropilosa (Terezan et al, 2010).…”

“…Terezan et al (2010) isolaram dos galhos de S. odoratissima os alcaloides furoquinolínicos (dictamina, γ-fagarina e esquimianina) e 2-arilquinolin-4-ona (2-fenil-1-metilquinolin-4-ona) e limonoides (ácido limonéxico e limonina). Os alcaloides furoquinolínicos, 2-arilquinolin-4-ona e os limonoides mostraram atividade inseticida e/ou fungicida para o ninho da formiga Atta sexdens rubropilosa (Terezan et al, 2010).…”