No abstract

We examined the effects of the flavonoids pinocembrin and quercetin on the feeding behavior, survival, and development of the Cucurbitaceae pest Epilachna paenulata (Coleoptera: Coccinellidae). In no-choice experiments, 48 hr-consumption of Cucurbita maxima Duch. leaves treated with pinocembrin at 1, 5, and 50 microg/cm(2) was less than one third of that for leaves treated with 0.1 microg/cm(2) of pinocembrin or untreated leaves. Larvae stopped feeding after 9 days of high doses of pinocembrin (5 and 50 microg/cm(2)), and larval weight and survival were negatively affected by pinocembrin at 1-50 microg/cm(2). Delayed mortality in comparison to food-deprived larvae suggests that the mechanism of action for pinocembrin is chronic intoxication, rather than simple starvation from antifeedant effects. In contrast, leaf consumption and larval weight were not significantly affected by quercetin (at 0.1, 1, 5, and 50 microg/cm(2)) while mortality rates were only slightly increased. The response of E. paenulata larvae in a choice-test to combinations of pinocembrin at antifeedant doses (5 and 50 microg/cm(2)) and quercetin at phagostimulant doses (0.01 and 0.1 microg/cm(2)) indicated that the feeding deterrent activity of the former completely overshadowed the stimulant activity of the latter. These results demonstrate the different responses of one insect species to two widely distributed plant flavonoids. Pinocembrin strongly affected survival of E. paenulata while quercetin had only a weak effect without major consequences on the insect life-cycle.

The antibacterial and cytotoxic effects of metabolites isolated from an antibacterial extract of Flourensia oolepis were evaluated. Bioguided fractionation led to five flavonoids, identified as 2′,4′-dihydroxychalcone (1), isoliquiritigenin (2), pinocembrin (3), 7-hydroxyflavanone (4), and 7,4′-dihydroxy-3′-methoxyflavanone (5). Compound 1 showed the highest antibacterial effect, with minimum inhibitory concentration (MIC) values ranging from 31 to 62 and 62 to 250 μg/mL, against Gram-positive and Gram-negative bacteria, respectively. On further assays, the cytotoxic effect of compounds 1–5 was determined by MTT assay on acute lymphoblastic leukemia (ALL) and chronic myeloid leukemia (CML) cell lines including their multidrug resistant (MDR) phenotypes. Compound 1 induced a remarkable cytotoxic activity toward ALL cells (IC50 = 6.6–9.9 μM) and a lower effect against CML cells (IC50 = 27.5–30.0 μM). Flow cytometry was used to analyze cell cycle distribution and cell death by PI-labeled cells and by Annexin V/PI staining, respectively. Upon treatment, 1 induced cell cycle arrest in the G2/M phase accompanied by a strong induction of apoptosis. These results describe for the first time the antibacterial metabolites of F. oolepis extract, with 1 being the most effective. This chalcone also emerges as a selective cytotoxic agent against sensitive and resistant leukemic cells, highlighting its potential as a lead compound.

Flavonoids function in many aspects of plantinsect interactions, but the responses of insects to these compounds vary greatly. In this study, we determined the effects of two widely distributed flavonoids, pinocembrin and quercetin, on the feeding behavior, survival, and development of the fall armyworm Spodoptera frugiperda J.E. (Smith) (Lepidoptera: Noctuidae). In a choice test, S. frugiperda larvae strongly rejected leaves treated with pinocembrin at concentrations of 10, 50, or 100 lg/cm 2 . Larvae fed normally on leaves treated with quercetin at 10 and 50 lg/cm 2 , but showed 57 % deterrence when fed on leaves treated with 100 lg/cm 2 quercetin. At concentrations of 0.01-1 lg/cm 2 , pinocembrin and quercetin functioned as phagostimulants for S. frugiperda. In a multiplechoice experiment, S. frugiperda larvae preferred to consume untreated leaves or those treated with 0.1 lg/cm 2 pinocembrin, but rejected leaves treated with 5-50 lg/cm 2 pinocembrin. In a no-choice feeding experiment, larvae fed on leaves treated with 5 and 50 lg/cm 2 pinocembrin consumed less than those fed on leaves treated with 0.1 and 1 lg/cm 2 pinocembrin or untreated leaves. Pinocembrin at 1-50 lg/cm 2 negatively affected larval weight and survival, thus showing a toxic effect. In contrast, leaf consumption and larval weight were not significantly affected by quercetin at 0.1, 1, 5, and 50 lg/cm 2 , and mortality rates only slightly increased. Because of its dual activity, pinocembrin could be used for insect control in a stimulo-deterrent diversionary strategy: the same compound could promote both stimulate (low doses) and deter insect activity (high doses).

The results suggest that drimanic compounds have potential as new agents against S. frugiperda and E. paenulata. A quantitative structure-activity relationship (QSAR) analysis of the whole series, supported by electronic studies, suggested that drimanic compounds have structural features necessary for increasing antifeedant activity, namely a C-9 carbonyl group and an epoxide at C-8 and C-9. © 2018 Society of Chemical Industry.

The aim of this study was to isolate the active principles of Flourensia oolepis S.F.Blake (Asteraceae), which completely inhibited the germination of Raphanus sativus seeds at 10 mg/ml. Flavanone pinocembrin and sesquiterpene ilicol, were isolated by bioassay-guided fractionation. They were active both against monocot and dicot seeds. Pinocembrin was the most active compound, with an IC50 (germination) value of 0.24, 3.40, 3.28, and 3.55 mM against Panicum miliaceum, Avena sativa, Lactuca sativa, and R. sativus, respectively; ilicol, however, exhibited IC50 (germination) values of 0.67, 2.73, 5.25, and 9.66 mM for the same species, respectively. Pinocembrin and ilicol inhibited root growth and showed IC50 (root growth) values of 0.199, 14.68, 8.05, 7.69 mM, and 1.22, 2.90, 7.35, 8.07 mM, against P. miliaceum, A. sativa, L. sativa, and R. sativus, respectively. Pinocembrin and ilicol reduced Allium cepa cell division without chromosome aberrations.

The enzyme 4-hydroxyphenylpyruvate dioxygenase catalyzes the second step in the tyrosine degradation pathway. In mammals, this enzyme is the molecular target of drugs used for the treatment of metabolic disorders associated with defects in the tyrosine catabolism, mainly the fatal hereditary disease tyrosinemia type 1. This study evaluated the inhibitory effect of 91 extracts on 4-hydroxyphenylpyruvate dioxygenase from mostly native plants from central Argentina. Flourensia oolepis ethanol extract showed itself to be the most effective, and bioguided fractionation yielded pinocembrin (1) as its active principle. This flavanone, with an IC50 value of 73.1 µM and a KI of 13.7 µM, behaved as a reversible inhibitor of the enzyme and as a noncompetitive inhibitor. Molecular modeling studies confirmed the inhibitory potency of 1 and explained its activity by means of in silico determination of its binding mode in comparison to inhibitors of known activity, cocrystallized with 4-hydroxyphenylpyruvate dioxygenase. The main structural determinants that confer its potency are discussed. Analysis of the binding mode of the flavanone 1 with 4-hydroxyphenylpyruvate dioxygenase revealed the basis of the noncompetitive reversible mechanism of inhibition at the molecular level, which seems to be a common feature in this ubiquitous family of natural compounds. The resulting information may establish the basis for obtaining novel 4-hydroxyphenylpyruvate dioxygenase inhibitors for the treatment of tyrosinemia type 1 and other disorders associated with tyrosinase catabolism.

The aim of this study was to evaluate whether foraging decisions of Acromyrmex lundi in the field are affected by the extract of Aristolochia argentina. A free choice test was performed using Rosa x hybrida leaves treated with the extract and control with acetone. Two leaves (treated and control) were presented on either side of a foraging trail. The percentage of removed material was recorded for 90 minutes of observation on two consecutive days. Dry weight and repellency index were calculated. Ant activity, the percentage of carried leaves and weight data were analyzed using a "t"-test for paired data, and a General Linear Mixed Model test was used to evaluate the different variables and their interactions. A. argentina extract (1%) did not affect the foraging activity of A. lundi, whereas the 5% dose caused significant differences in foraging activity as well as between the factors and the interactions. A repellency index of above 95% was obtained at the 5% dose. The extract of A. argentina could be considered for future management of this insect.