Effect of structurally related flavonoids from Zuccagnia punctata Cav. on Caenorhabditis elegans

Abstract

Zuccagnia punctata Cav. (Fabaceae), commonly called jarilla macho or pus-pus, is being used in traditional medicine as an antiseptic, anti-inflammatory and to relieve muscle and bone pain. The aim of this work was to study the anthelmintic effects of three structurally related flavonoids present in aerial parts of Z. punctata Cav. The biological activity of the flavonoids 7-hydroxyflavanone (HF), 3,7-dihydroxyflavone (DHF) and 2´,4´-dihydroxychalcone (DHC) was examined in the free-living nematode Caenorhabditis elegans. Our results showed that among the assayed flavonoids, only DHC showed an anthelmintic effect and alteration of egg hatching and larval development processes in C. elegans. DHC was able to kill 50% of adult nematodes at a concentration of 17 μg/mL. The effect on larval development was observed after 48 h in the presence of 25 and 50 μg/mL DHC, where 33.4 and 73.4% of nematodes remained in the L3 stage or younger. New therapeutic drugs with good efficacy against drug-resistant nematodes are urgently needed. Therefore, DHC, a natural compound present in Z. punctata, is proposed as a potential anthelmintic drug.

Essential oil of Peumus boldus Molina against the nematode Haemonchus contortus (L3) and three stored cereal insect pests

“…This supports the hypothesis that some bioactive compound could cause this ovicidal effect with a sufficiently small size (less than 600 Da) to penetrate and kill the egg in the morula phase (Vargas-Magaña et al, 2014). In addition, the advantage of this size is that compounds can accumulate in effective concentrations in nematodes (D'Almeida et al, 2014…”

Zuccagnia punctata Cav., a Potential Environmentally Friendly and Sustainable Bionematicide for the Control of Argentinean Horticultural Crops

“…From them, only 2′,4′-dihydroxychalcone showed an anthelmintic effect and alteration of egg hatching and larval development processes in C. elegans . Additionally, this chalcone was able to kill 50% of adult nematodes at a concentration of 17 μg/mL [ 37 ].…”

Potent Anthelmintic Activity of Chalcones Synthesized by an Effective Green Approach

“…[36] Also, 4'-dihydroxychalcone (DHC), one of the major constituents present in plant Zuccagnia punctata [37,38] kills C. elegans after a day of exposure showing an LC 50 of 17 μg/ml. [39] The molecular architecture of the chalcone core is based on a chain flavonoid, chemically typified with the 1,3-diaryl-2propen-1-one framework, in which both aromatic rings (rings A and B) are linked by an unsaturated α,β-carbonyl system. It is believed that the diversity of pharmacological activities can be attributed to the conjugation between the unsaturation and the carbonyl group present in its structure.…”

“…It was shown that the chalcone scaffold as well as some organic and ferrocenyl derivatives exert long‐term paralysis [36] . Also, 4'‐dihydroxychalcone (DHC), one of the major constituents present in plant Zuccagnia punctata [37,38] kills C. elegans after a day of exposure showing an LC 50 of 17 μg/ml [39] …”