A new class of deep eutectic solvents (DES) was used in the extraction of levodopa (L-dopa) present in Mucuna cinerea, which has been termed “green” or “designer” solvents, with notable productive and economic/environmental benefits. The seeds of Mucuna cinerea were prepared and submitted to extraction with heating and agitation in a solvent mixture of DES with citric acid, urea, or glycerol. The extracts were analyzed by high performance liquid chromatography (HPLC) which confirmed the efficiency of DES in extracting L-dopa. These extractions were carried out to determine the L-dopa extracts in DES with regard to the induction of cellular response activity, demonstrating the synergy between L-dopa and DES. The DES-glycerol extract exhibited a higher proliferative activity than commercial L-dopa after 24 h of treatment. The human glandular kallikrein-1 gene (hGK3) demonstrated higher expression in the treatment with the DES-urea, while the G protein-coupled receptor kinase-6 gene (GRK6) showed higher expression for all extracts compared to commercial L-dopa, with a higher value obtained for DES glycerol, followed by DES urea extract. The DES extraction method is therefore promising and unprecedented, confirming its possible use in the replacement of expensive solvents, supporting the use of ecologically viable DES in the extractions of other plant species.

Abstract The aim of this study is to investigate the application of ultrasound in the extraction of betanin from beets (Beta vulgaris) using Deep eutectic solvents (DES). The extraction process was optimized using response surface methodology. The time variable was found to be correlated with the extraction performance. Three DES (choline chloride: urea (CC:U), choline chloride: glycerol (CC:G), and choline chloride: citric acid (CC:Ac)) were studied. The concentration of betanin extracted with CC:U, CC:G, and CC:Ac was 41.27-67.51, 82.46-104.45, and 50.06-111.93 mg/100 g. The maximum betanin extraction of 111.193 mg/100 g was achieved with CC:Ac in 38 min using 44% DES in water in an ultrasonic bath. These results demonstrate that DESs are excellent solvents for the extraction of betanin with superior efficiency to conventional extraction solvents. Ultrasound significantly improved the efficiency of betanin extraction from beets. However, a higher betanin content in the extracts did not translate into greater active antioxidant capacity, which may be related to the synergistic effects of other compounds present in the beet extracts. This study is the first attempt to optimize the parameters for ultrasound extraction of betanin from B. vulgaris using eutectic solvents.

Crotalaria ochroleuca (Fabaceae) is rich in bioactive compounds used for nematode control. Transformed root culture allows the production of a large amount of hairy root biomass, conditioned by auxin biosynthesis-related genes integrated via the process of Agrobacterium rhizogenes infection, which is known to cause a hairy root phenotype. We transformed A. rhizogenes to increase the biomass of hairy roots and optimized the process of production of bioactive compounds. The transformed nature of hairy roots was confirmed by polymerase chain reaction, which confers kanamycin resistance. The transformed roots were cultured in full-strength in liquid media to realize the growth of hairy roots and the production of bioactive compounds. The transformed roots were grown in a culture medium supplemented with elicitors to produce total phenols, and flavonoids. Chromatographic analysis of transformed roots revealed the presence of flavonoids apigenin-6,8-C-diglucoside and luteolin-6-C-glucoside. The results were obtained by conducting physiological and biochemical studies with the Flavonoids and studying the pathways that led to the production of large amounts of bioactive compounds from the hairy roots of C. ochroleuca. It was observed that the extraction of the compounds significantly affected nematodes and insect larvae, resulting in significantly high levels of economic damage to crops.

Bicyclo[2.2.1]hepta-2,5-diene or norbornadiene (NBD) is a bicyclic hydrocarbon molecule used in many fields of chemistry since its first synthesis in 1950. NBD is the precursor of Aldrin, an agrochemical that was commonly used as an insecticide until the end of the XX century. Norbornadiene is capable of interconverting into its isomer, quadricyclane (QC), by the incidence of ultraviolet light. After that, the QC can release heat to return to the initial stage of NBD. To increase the energy efficiency and to enable the reaction to occur at the solar light, chemists have synthesized a wide variety of NBD derivatives. Papers in more than seventy years have studied and reported the physical and chemical properties of those compounds and their applications as rocket fuel, solar energy cell, homogeneous catalysis, and agrochemicals published between 1950 and 2021. Even computational chemistry has been used to investigate the NBD derivatives synthetic routes, elucidation, and application. In addition, this review describes other applications of norbornadiene.

Carpotroche brasiliensis is a tree native to Brazil, belonging to the family Flacurtiaceae, whose seeds contain a group of cyclopentenyl fatty acids: gorlic (12%), chaulmugric (27%), and hydnocarpic (48.7%). These compounds are considered the main therapeutic agents in the treatment of leprosy. In the present study, a series of novel triazole compounds were obtained by conjugation between hydnocarpic acid and functionalized azides via copper(I)-catalyzed azide-alkyne cycloaddition reaction (CuAAC). Hydnocarpic acid and its derivatives were tested against estrogen-positive breast carcinoma (MCF-7), hepatocellular carcinoma (HepG2), and non-small cell lung cancer (A549) cell lines. The (R)-(1-(pyridin-2-ylmethyl)-1H-1,2,3-triazol-4-yl)methyl-11-(cyclopent-2-en-1-yl)undecanoate (8) displayed promising antiproliferative activity against A549 cells. We demonstrated that this compound selectively inhibited the viability of A549 cell cultures. Furthermore, compound 8 inhibited the clonogenic capacity of A549 cells, and this effect was associated to its ability to inhibit cell cycle progression at G1 phase. These findings indicate that 8 is a promising antitumor agent on A549 cells and support further studies to evaluate the molecular mechanisms underlying its antiproliferative activity. In addition, hydnocarpic acid should be considered as a promising chemical prototype to obtain novel antineoplastic agents.

Nematode is a major problem in agriculture, the effective way to control this pest is through chemical control, but the efficient molecules present in the market have great toxicity to mammals and birds. Thus, there is a constant demand for the development of new nematicide molecules. This study describes the synthesis of 21 novel esters derived from norbornadiene and evaluation of their potential activity against Meloidogyne javanica. The esters 5-25 presented 50% mortality of the nematodes. The acid 3 and the ester 4 caused 96 and 93% mortality of the nematodes, respectively. The lethal concentration to kill 50% of the nematodes (LD50) were determined as being 11.8 µg mL-1 for the acid 3 and 99.4 µg mL-1 for the ester 4. According to the results obtained it is believed that polarity seems to be a key factor for the higher activity of compound 3 compared to structurally similar ester derivatives.

ABSTRACT: The demand for effective insecticides in pest control with low toxicity to the non-target organisms, such as natural enemies and pollinators, is increasing steadily. A good alternative for synthetic insecticides is natural compounds, including essential oils (EO). This work assessed toxicity of essential oils extracted from Artemisia annua, A. absinthium, A. camphorata, A. dracunculus and A. vulgaris against the melonworm Diaphania hyalinata (Linnaeus, 1758) (Lepidoptera: Crambidae) larvae, a pest of Cucurbitaceae, and their selectivity for fire ant Solenopsis saevissima (Smith) (Hymenoptera: Formicidae) and jataí bee Tetragonisca angustula (Latreille) (Meliponinae). The plants were grown in a greenhouse with mineral fertilization and were used for EO extraction. The insects in the bioassay belonged to the second instar of D. hyalinata and adult forms of S. saevissima and T. angustula. Essential oil from A. annua induced a high mortality rate in D. hyalinata (96 %) over a 48 h period. The same essential oil was selective for predator S. saevissima (42 % mortality) and pollinator T. angustula (74 % mortality), while causing high mortality in D. hyalinata. The insecticidal activity of A. annua oil was attributed to the synergism of its constituents viz., camphor and 1,8-cineole. Therefore, this essential oil contains constituents that are promising for effective use as insecticide due to its high toxicity and rapid action against D. hyalinata as well as low toxicity for predator and pollinator.

Dipteryx odorata (Aubl.) Willd. is a tall arboreal species native to Central and Northern South America. This paper describes the chemical characterization and phytotoxic potential of polar and non-polar extracts from D. odorata seeds. Structural determinations were accomplished by chemical derivatization and analyzed by GC/MS. The chemical composition of the non-polar fraction (hexane and dichloromethane) presented fatty acids as major constituent. Medium polar and polar fractions (ethyl acetate and ethanol: water) contained carboxylic acid and high 6,7-Dyhidroxycoumarin-β-D-glucopyranoside content, not previously reported for seeds of D. odorata. Extracts showed a significant level of phytotoxic activity, correlated to the content of coumarin derivatives, predominantly in the polar fraction.

Anatomical and histochemical investigations of Sphagneticola trilobata (L.) Pruski, Asteraceae, secretory structures in leaves and stems and the seasonal variation of essential oils were carried out. Histochemical techniques enabled the specific location of the essential oil accumulation in the internal (canals) and external structures (trichomes). Histochemical analysis showed that the secretory trichomes produced steroids. The highest yield was obtained from plants collected in winter, when it was registered low temperature and precipitation. The essential oil was characterized by high percentage of hydrocarbon sesquiterpenes, hydrocarbon monoterpenes and low levels of oxygenated sesquiterpenes. The major components were germacrene D (11.9-35.8%), α-phellandrene (1.4-28.5%), α-pinene (7.3-23.8%), E-caryophyllene (4.6-19.0%), bicyclogermacrene (6.0-17.0%), limonene (1.8-15.1%) and α-humulene (4.0-11.6%). The percentage of most of the individual constituents present in S. trilobata essential oil changed significantly during the months.

Volatile oils from the leaves of Verbenaceae species Aloysia virgata, Lantana camara, Lantana trifolia, Lantana montevidensis, Lippia brasiliensis and Lippia sericea were investigated for its chemical composition and antibacterial activity. The volatile oils were characterized by a high content of sesquiterpenes of which (E)-caryophyllene (10-35%), germacrene-D (5-46%) and bicyclogermacrene (7-17%) were the major components for all studied species. For the flowers, a higher concentration of monoterpenes was observed for the species L. camara, L. trifolia and L. brasiliensis. These compounds probably act as attractive to specific pollinators. The volatile oils from A. virgata was the most active, exhibiting moderate antimicrobial activity against the bacteria Staphylococcus aureus, Bacillus cereus and Escherichia coli.

The essential oils of seven Myrtaceae species were investigated for its chemical composition and antibacterial activity. The volatile oils were characterized by a high content of monoterpenoids of which 1,8-cineole (88.0, 65.0 and 77.0% for Melaleuca hypericifolia, Callistemon viminalis and Callistemon citrinus respectively), terpinen-4-ol (47.0 and 49.8% for Melaleuca thymifolia and Callistemon polandii respectively) and α-pinene (54.5% for Kunzea ericoides) were the major components. The oil from M. linariifolia was characterized by a high concentration of methyleugenol (87.2%). The oil from Melaleuca thymifolia was the most active, exhibiting high antimicrobial activity against all tested bacteria.

The root exudates produced by sorghum contain a biologically active constituent known as sorgoleone. The behavior of sorgoleone in a Red-Yellow Latosol was studied. The sorption model of sorgoleone in soil was better adjusted to the Freundlich equation, through the coefficients Kf (capacity of sorption) and 1/n (linearity of the isotherm). The persistence of sorgoleone in soil and its possible degradation were also evaluated by monitoring their residues in the soil along the time. Recovery rate of sorgoleone from the soil reached 93% after 24h. It was verified that sorgoleone is strongly sorbed in the soil and its half-life is 10 days, under the experimental conditions. The presence of sorgoleone or its metabolites was not detected in the soil after 60 days.

Phytochemical investigation of the aerial parts and roots of Mucuna cinerea led to the isolation of a mixture of fatty acids, triacylglicerols, beta-sitosterol, stigmasterol, stigmasterol glucoside, daucosterol, asperglaucide (4) and the isoflavonoids prunetin (1), genistein (2), medicarpin (3), daidzein (5), 7-O-alpha-glycopiranosyl daidzein (6). An in vitro bioassay was carried out with compounds 1-4, at the concentration of 50 and 5 mug mL-1 against the phytonematodes M. incognita and H. glycines. Although the four compounds showed some nematocidal property, the most active was (1), causing 70% mortality of M. incognita at the concentration of 50 mug mL-1.

3,5-Dimethoxybenzylic alcohol was converted into the 2-acetoxy-5-methoxy-3-(pent-1-yl)-1,4-benzoquinone (12), in seven steps, with an overall yield of 14.6%. The natural quinone sorgoleone (1) was isolated from Sorghum bicolor and converted into the corresponding quinone (13) having a saturated side chain. The selective effects of these compounds (1, 12 and 13), at the dose of 5.6 mug of a.i./ g of substrate, on the growth of Cucumis sativus, Lactuca sativa, Desmodium tortuosum, Hyptis suaveolens and Euphorbia heterophylla were evaluated. All three compounds caused some inhibition on the root growth of the test plants (0.0-69.19%) with the aerial parts less affected. The results showed that the triene unit of the sorgoleone side chain is not essential for the phytotoxicity and also the synthetic quinone was as active as the natural product.

O estudo químico das cascas de Ochroma lagopus Swartz levou ao isolamento e ou, identificação de uma mistura de ácidos graxos e triacilglicerídeos, de b-sitosterol (1), estigmasterol (2), daucosterol (3), estigmasterol-3-O-b-D-glicosídeo (4) e manitol (5).

Phytochemical investigation of the bark from Ochroma lagopus Swartz led to the isolation and or identification of a mixture of fatty acids and triacylglycerides, sitosterol (1), stigmasterol (2), daucosterol (3), stigmasterol-3-O-b-D-glycoside and mannitol (5).