Neotropical Flora's Contribution to the Development of Biorational Products for Drosophila suzukii Control.

Essential oils (EOs) produced by aromatic plants belonging to different families, such as Asteraceae, Lamiaceae, Lauraceae, Myrtaceae, and Piperaceae, are generally suggested as potential sources of new molecules with insecticidal activity. The EOs are constituted bioactive molecules that may have to control Drosophila suzukii (Matsumura), a serious economic invasive pest of small fruits worldwide. Currently, the control strategy against D. suzukii depends especially on treatment with synthetic insecticides. Due to impacts to human health and the environment, efforts have been made to seek efficient insecticides in chemical pest control. Thus, sixty-five oils extracted from plants were selected to find new alternative types of insecticides active against D. suzukii. The monoterpenes, such as limonene, α-pinene, 1,8-cineole, linalool, menthol, geranial, and neral, were the most representative, which stand out for their insecticidal efficiency. The OEs demonstrated to be used in the management of D. suzukii, thus being an effective strategy to control this pest, ensuring crop protection and agricultural sustainability. Therefore, the substitution by natural products or eco-friendly pesticides instead of synthetic pesticides represents a notable option to mitigate harmful effects on human health and the environment.

NMR and multivariate methods: Identification of chemical markers in extracts of pedra-ume-caá and their antiglycation, antioxidant, and enzymatic inhibition activities.

INTRODUCTION: In Brazil, the plant group popularly known as "pedra-ume-caá" is used in folk medicine for the treatment of diabetes, and its raw material is commonly sold. OBJECTIVE: The aim of the study was to apply a method for chemical identification of extracts of dry pedra-ume-caá leaves using HPLC-high-resolution mass spectrometry (HRMS) and NMR and develop a multivariate model with NMR data to authenticate commercial samples. In addition, to evaluate the biological activities of the extracts. MATERIALS AND METHODS: Dry extracts of Myrcia multiflora, Myrcia amazonica, Myrcia guianensis, Myrcia sylvatica, Eugenia punicifolia leaves, and 15 commercial samples (sold in Manaus and Belém, Brazil) were prepared by infusion. All the extracts were analysed using HPLC-high-resolution mass spectrometry (HRMS), NMR, principal component analysis (PCA), and hierarchical cluster analysis (HCA). The antidiabetic effect of extracts was evaluated according to enzymatic inhibition. Their content of total phenols, cell viability, and antioxidant and antiglycation activities were also determined. RESULTS: HPLC-HRMS and NMR analysis of these extracts permitted the identification of 17 compounds. 1H NMR data combined with multivariate analyses allowed us to conclude that catechin, myricitrin, quercitrin, and gallic and quinic acids are the main chemical markers of pedra-ume-caá species. These markers were identified in 15 commercial samples of pedra-ume-caá. Additionally, only the extracts of M. multiflora and E. punicifolia inhibited α-glucosidase. All the extracts inhibited the formation of advanced glycation end products (AGEs) and showed free-radical-scavenging activity. These extracts did not present cytotoxicity. CONCLUSION: This study revealed the chemical markers of matrices, and it was possible to differentiate the materials marketed as pedra-ume-caá. Moreover, this study corroborates the potential of these species for treating diabetes.

Characterization and bioaccessibility assessment of bioactive compounds from camu-camu (Myrciaria dubia) powders and their food applications.

Camu-camu (Myrciaria dubia) is a tropical fruit known for its content of bioactive compounds. This study aimed to evaluate physicochemically, morphologically, andsensorialpowders from camu-camu obtained by spray-drying at two inlet temperatures (150 °C and 180 °C) with three encapsulating agents (maltodextrin, whey protein and a 50:50 mixture of both) and by freeze-drying of whole fruit. The use of maltodextrin protected bet anthocyanins (cyanidin-3-glucoside (C3G) and delphinidin-3-glucoside (D3G)), but whey protein showed a better protective effect on ascorbic and malic acids. These facts were confirmed during the storage stability test, finding that relative humidity is a critical variable in preserving the bioactive compounds of camu-camu powders. The powders with the highest content of bioactive compounds were added to a yogurt and a white grape juice, and then sensory evaluated. The bioaccessibility studies in gastric and intestinal phases showed better recovery percentages of bioactive compounds in camu-camu powders (up to 60.8 %) and beverages (up to 90 %) for C3G, D3G, ascorbic acid, and malic acid than in the fruit juice. Dehydration of camu-camu (M. dubia) is a strategy to increase the bioactive compounds stability, modulate the fruit sensory properties, and improve their bioavailability after incorporation in food matrices.

Development and characterization of films from Campomanesia xanthocarpa and commercial citrus pectins with different degrees of methyl-esterification.

In this study, pectins from commercial citrus and isolated from gabiroba (Campomanesia xanthocarpa) fruits, were obtained with different degrees of methyl-esterification (DM) and applied in the films. The DM ranged from 0 % to 62.5 % and the gradual de-esterification process was confirmed by mono-dimensional analysis (1H NMR). In order to investigate the influence of DM values in pectin film properties, PCP (DM: 62.5 %); PCP-5 (DM: 37.4 %); PCP-15 (DM: 19.1 %), and a fully de-esterified sample PCP-35 (DM: 0 %) were selected. The functional properties of the films clearly showed that the DM and cross-linking process are necessary to obtain a material with water resistance. Furthermore, pectin isolated from the fruits of gabiroba was purified (GW-Na, DM: 51.9 %) and partially de-esterified (GW-Na-5, DM: 37.1 %). These pectins were used, for the first time, in development of films and the physical and mechanical properties were compared with films made with PCP and PCP-5 samples. GW-Na and GW-Na-5 films presented suitable properties, with reduced solubility reduced (57.1 and 26.2 %), high degree of swelling (2.14 and 2.26), low flexibility (18.05 and 6.11 MPa), respectively. High strength and rigidity (99.36 and 1040.9 MPa), for both films (GW-Na and GW-Na-5) were demonstrated, similar to that obtained by analyzed citrus pectin.

Biotechnological and socio-environmental potential of Campomanesia adamantium (Myrtaceae): an interdisciplinary review.

Guavira (Campomanesia adamantium, Myrtaceae) is a native fruit from the Brazilian Cerrado savanna and is socio-economically important for the indigenous and traditional people living in the Central-West. This is a bibliographic review of the biological properties of guavira and its derivatives, and, after discussing experimental studies, an interdisciplinary approach is conducted highlighting the im-portance of Agroforestry Systems as an ecological restoration tool to leverage the production chain of guavira while providing ecosystem services. Many research groups studied effects of polyphenols and other bioactive compounds and biological properties of this fruit and other plant parts such as antibiotic, antioxidant, anti-inflammatory, anti-hyperlipidemic, anti-diarrheic and antitumoral activities, cardiovascular and hepatic protection and action against neuropathic pain. Besides, guavira by-products benefit poultry intestinal health, similarly to antibiotics added to their feed. Furthermore, several biotechnological products were found, like pulp flour, seasoning from the peel, sunscreen, and seed oil similar to olive oil with pharmaceutical and industrial potential. We conclude by emphasizing the importance of guavira for restoration and preservation of the threatened Brazilian Cerrado, and for the socio-environmental development of family agriculture. The same approach and study are welcome and necessary in other regions and domains worldwide having their native flora as means for a restorative end.

Campomanesia adamantium O Berg. fruit, native to Brazil, can protect against oxidative stress and promote longevity.

Campomanesia adamantium O. Berg. is a fruit tree species native to the Brazilian Cerrado biome whose fruits are consumed raw by the population. The present study determined the chemical composition of the C. adamantium fruit pulp (FPCA) and investigated its in vitro antioxidant potential and its biological effects in a Caenorhabditis elegans model. The chemical profile obtained by LC-DAD-MS identified 27 compounds, including phenolic compounds, flavonoids, and organic carboxylic acids, in addition to antioxidant lipophilic pigments and ascorbic acid. The in vitro antioxidant activity was analysed by the radical scavenging method. In vivo, FPCA showed no acute reproductive or locomotor toxicity. It promoted protection against thermal and oxidative stress and increased the lifespan of C. elegans. It also upregulated the antioxidant enzymes superoxide dismutase and glutathione S-transferase and activated the transcription factor DAF-16. These results provide unprecedented in vitro and in vivo evidence for the potential functional use of FPCA in the prevention of oxidative stress and promotion of longevity.

Neither lysigenous nor just oil: Demystifying myrtaceous secretory cavities.

PREMISE: Leaf subepidermal secretory cavities are a notable trait in Myrtaceae, but their formation is still controversial because of the lack of consensus on their ontogeny among authors. Knowledge about the compounds present in these cavities has grown over the last few years, demonstrating that terpenoid-rich oils are not their unique content. These two points are the focus of this study on the ontogeny, structure, and contents of secretory cavities in neotropical Myrtaceae. METHODS: We used histochemical tests and Raman analysis to verify the basic chemical composition of the cavity contents of nine species. We studied the ontogeny of glands in one species, comparing aldehyde-fixed tissues and fresh sections mounted in an inert medium. RESULTS: We observed schizogenous development and appearance of the secretory cavities and found that sample processing may induce cell breakdown, which can be misinterpreted as lysigeny. The content of these cavities contains putative terpenes, resins, carbonyl groups, and flavonoids. CONCLUSIONS: Our findings support the hypothesis that the lysigenous appearance of the oil glands is a technical artifact. These tissue distortions must be considered when interpreting the development of this type of secretory structure. Moreover, the basic analyses of chemical constituents show for the first time that the glands of neotropical Myrtaceae are potential reservoirs of some compounds such as flavonoids previously reported as novelties for a few other myrtaceous species. Because some of them are non-lipid compounds, the idea that the glands are just oil repositories is no longer applicable.

Chemical composition, seasonal variation and antiaging activities of essential oil from Callistemon subulatus leaves growing in Egypt.

Callistemon is an aromatic genus of flowering plants belonging to family Myrtaceae. The essential oils of C. subulatus leaves were collected in four seasons and analyzed using GC/MS. The oils demonstrated monoterpenes as the predominant class. Eucalyptol was the main component in all seasons; summer (66.87%), autumn (58.33%), winter (46.74%) and spring (44.63%), followed by α-pinene; spring (31.41%), winter (28.69%), summer (26.34%) and autumn (24.68%). Winter oil, the highest yield (0.53 mL/100g), was further investigated for its inhibitory activity against enzymes associated with ageing; elastase and acetylcholinesterase. It remarkably inhibited elastase and acetylcholinesterase with IC50 values of 1.05 and 0.20 µg/ml, respectively. A molecular docking study was conducted for the major oil components on the active sites of target enzymes. Eucalyptol revealed the best binding affinity for both enzymes. C. subualtus oil could be used as supplement for management of ageing disorders like skin wrinkles and dementia.

Comparative Bioactivity Evaluation of Chemically Characterized Essential Oils Obtained from Different Aerial Parts of Eucalyptus gunnii Hook. f. (Myrtaceae).

Essential oils (EOs) obtained by hydro-distillation from different parts of twigs (EOT), leaves (EOL), and fruits (EOF) of Eucalyptus gunnii Hook. f. were screened for their chemical composition, insecticidal, repellence, and antibacterial properties. Based on GC and GC/MS analysis, 23 constituents were identified across the twigs, leaves, and fruits, with 23, 23, and 21 components, respectively. The primary significant class was oxygenated monoterpenes (82.2-95.5%). The main components were 1,8-cineole (65.6-86.1%), α-terpinyl acetate (2.5-7.6%), o-cymene (3.3-7.5%), and α-terpineol (3.3-3.5%). All three EOs exhibited moderate antibacterial activities. EOL was found to have higher antibacterial activity against all tested strains except Dickeya solani (CFBP 8199), for which EOT showed more potency. Globally, Dickeya solani (CFBP 8199) was the most sensitive (MIC ≤ 2 mg/mL), while the most resistant bacteria were Dickeya dadantii (CFBP 3855) and Pectobacterium carotovorum subsp. carotovorum (CFBP 5387). Fumigant, contact toxicity, and repellent bioassays showed different potential depending on plant extracts, particularly EOT and EOL as moderate repellents and EOT as a medium toxicant.

Xanchryones I-N, Six Unusual Phloroglucinol-Amino Acid Hybrids from the Leaves of Xanthostemon chrysanthus.

Six new phloroglucinol derivatives, xanchryones I-N (1-6), were isolated from the leaves of Xanthostemon chrysanthus. Compounds 1-6 are unusual phloroglucinol-amino acid hybrids constructed through C2 -N and O-C1 ' bonds forming a peculiar oxazole ring. The structures and absolute configurations of compounds 1-6 were determined by MS, NMR, and single-crystal X-ray diffraction. Moreover, the anti-inflammatory and antibacterial activities of these compounds were evaluated.

Campomanesia lineatifolia Ruiz & Pavón (Myrtaceae): Isolation of major and minor compounds of phenolic-rich extract by high-speed countercurrent chromatography and anti-inflammatory evaluation.

ETHNOPHARMACOLOGICAL RELEVANCE: Campomanesia lineatifolia Ruiz & Pavón (Myrtaceae), an edible species found in Brazilian Forest, possesses leaves that are traditionally used for the treatment of gastrointestinal disorders in Brazil. Extracts of C. lineatifolia are rich in phenolics and exhibit antioxidant, and gastric antiulcer properties. Furthermore, Campomanesia spp. have been described to possess anti-inflammatory properties, but studies related to chemical constituents of C. lineatifolia are scarce in the literature. AIM OF THE STUDY: This work aims to identify the chemical composition of the phenolic-rich ethanol extract (PEE) from C. lineatifolia leaves and evaluate the anti-inflammatory activity that could be related to its ethnopharmacological use. MATERIALS AND METHODS: The high-speed countercurrent chromatography (HSCCC), using an isocratic and a step gradient elution method, and NMR, HPLC-ESI-QTOF-MS/MS were used to isolate and identify the chemicals of PEE, respectively. Lipopolysaccharide-(LPS)-stimulated THP-1 cells were used to evaluate the anti-inflammatory activities from PEE and the two majority flavonoids isolated by measure TNF-α and NF-κB inhibition assays. RESULTS: Fourteen compounds were isolated from the PEE, further identified by NMR and HPLC-ESI-QTOF-MS/MS, twelve of them are new compounds, and two others are already known for the species. The PEE, quercitrin and myricitrin promoted a concentration-dependent inhibition of TNF-α, and PEE promoted an inhibition of NF-κB pathway. CONCLUSIONS: PEE from C. lineatifolia leaves demonstrated significant anti-inflammatory activity that may be related to the traditional use to treat gastrointestinal disorders.

Efficiency of Different Solvents in the Extraction of Bioactive Compounds from Plinia cauliflora and Syzygium cumini Fruits as Evaluated by Paper Spray Mass Spectrometry.

Jabuticaba (Plinia cauliflora) and jambolan (Syzygium cumini) fruits are rich in phenolic compounds with antioxidant properties, mostly concentrated in the peel, pulp, and seeds. Among the techniques for identifying these constituents, paper spray mass spectrometry (PS-MS) stands out as a method of ambient ionization of samples for the direct analysis of raw materials. This study aimed to determine the chemical profiles of the peel, pulp, and seeds of jabuticaba and jambolan fruits, as well as to assess the efficiency of using different solvents (water and methanol) in obtaining metabolite fingerprints of different parts of the fruits. Overall, 63 compounds were tentatively identified in the aqueous and methanolic extracts of jabuticaba and jambolan, 28 being in the positive ionization mode and 35 in the negative ionization mode. Flavonoids (40%), followed by benzoic acid derivatives (13%), fatty acids (13%), carotenoids (6%), phenylpropanoids (6%), and tannins (5%) were the groups of substances found in greater numbers, producing different fingerprints according to the parts of the fruit and the different extracting solvents used. Therefore, compounds present in jabuticaba and jambolan reinforce the nutritional and bioactive potential attributed to these fruits, due to the potentially positive effects performed by these metabolites in human health and nutrition.

Hybrids of ß-triketone and monoterpenoids from the peels of Callistemon viminalis.

Phytoconstituents of the peels of Callistemon viminalis has been investigated for the first time. As a result, two pair of diastereomers of hybrids of ß-triketone and α-phellandrene, named viminalisones A-B (1-2) and viminalisones CD (3-4), and three known analogues were obtained. Their structures and absolute configurations were elucidated through a combination of the analysis of their MS data, NMR spectra, single-crystal X-ray diffraction, and their experimental and calculated electronic circular dichroism (ECD) spectra. All isolates were evaluated for their antimicrobial activities against Botrytis cinerea and Cutibacterium acnes. Meroterpenoid 7 exhibited antibacterial activity against Botrytis cinerea with a MIC value of 0.256 mg/mL.

Myrcia paivae O.Berg (Myrtaceae) Essential Oil, First Study of the Chemical Composition and Antioxidant Potential.

The Myrtaceae family is one of the most representative in the Amazon. Several species have high added-value pharmacological potential. In order to contribute to the knowledge of the aromatic profile of Myrtaceae species from the Amazon, the present study presents the first report on the productivity, chemical composition, and antioxidant profile of the essential oil (EO) of Myrcia paivae. Dry leaves of the species were submitted to hydrodistillation to obtain their EO. The EO performance was calculated on a moisture-free basis and the analysis of the chemical profile was carried out by GC/MS. The determination of the antioxidant capacity was assessed by means of the antioxidant capacity equivalent to the inhibition Trolox of the ABTS•+ and DPPH• radicals. The results indicate that EO performance was equivalent to 1.69%. As for the chemical composition, hydrocarbon monoterpenes were predominant in the sample (>77%); terpinolene (14.70%), α-phellandrene (14.69%), γ-terpinene (9.64%), sylvestrene (7.62%), α-thujene (6.46%), and α-pinene (6.39%) were the constituents with higher content. Regarding the antioxidant capacity, the results show that the EO presented good results in the inhibition of ABTS•+ (0.886 ± 0.226 mM L−1) and DPPH• (2.90 ± 0.083 mM L−1), which can be attributed to the high monoterpene content in the sample.

Chemical Composition, Antioxidant, Antibacterial, and Antibiofilm Activities of Backhousia citriodora Essential Oil.

The essential oil of Backhousia citriodora, commonly known as lemon myrtle oil, possesses various beneficial properties due to its richness in bioactive compounds. This study aimed to characterize the chemical profile of the essential oil isolated from leaves of Backhousia citriodora (BCEO) and its biological properties, including antioxidant, antibacterial, and antibiofilm activities. Using gas chromatography-mass spectrometry, 21 compounds were identified in BCEO, representing 98.50% of the total oil content. The isomers of citral, geranial (52.13%), and neral (37.65%) were detected as the main constituents. The evaluation of DPPH radical scavenging activity and ferric reducing antioxidant power showed that BCEO exhibited strong antioxidant activity at IC50 of 42.57 µg/mL and EC50 of 20.03 µg/mL, respectively. The antibacterial activity results showed that BCEO exhibited stronger antibacterial activity against Gram-positive bacteria (Staphylococcus aureus and Staphylococcus epidermidis) than against Gram-negative bacteria (Escherichia coli and Klebsiella pneumoniae). For the agar disk diffusion method, S. epidermidis was the most sensitive to BCEO with an inhibition zone diameter of 50.17 mm, followed by S. aureus (31.13 mm), E. coli (20.33 mm), and K. pneumoniae (12.67 mm). The results from the microdilution method showed that BCEO exhibited the highest activity against S. epidermidis and S. aureus, with the minimal inhibitory concentration (MIC) value of 6.25 µL/mL. BCEO acts as a potent antibiofilm agent with dual actions, inhibiting (85.10% to 96.44%) and eradicating (70.92% to 90.73%) of the biofilms formed by the four tested bacteria strains, compared with streptomycin (biofilm inhibition, 67.65% to 94.29% and biofilm eradication, 49.97% to 89.73%). This study highlights that BCEO can potentially be a natural antioxidant agent, antibacterial agent, and antibiofilm agent that could be applied in the pharmaceutical and food industries. To the best of the authors' knowledge, this is the first report, on the antibiofilm activity of BCEO against four common nosocomial pathogens.

Phloroglucinols with hAChE and α-glucosidase inhibitory activities from the leaves of tropic Rhodomyrtus tomentosa.

Four undescribed phloroglucinol meroterpenoids, rhodotomentodiones A-D, and one undescribed phloroglucinol dimer, rhodotomentodimer A, were obtained and structurally established from tropic Rhodomyrtus tomentosa leaves. Their structures were unambiguously elucidated based on the comprehensive analyses of the NMR and MS spectroscopic data, electronic circular dichroism (ECD) calculation, and single-crystal X-ray diffraction. In particular, rhodotomentodiones A and B represent the first examples of phloroglucinol meroterpenoids featuring a unique γ-pyranoid moiety. More importantly, rhodotomentodimer A exhibited the most potential human acetylcholinesterase (hAChE) and α-glucosidase inhibitory effects with IC50 values of 7.5 µM and 5.6 µM, respectively. The possible interaction sites of the above potential hAChE and α-glucosidase inhibitor were achieved by molecular docking studies. These findings greatly enrich the diversity of natural products from Myrtaceae species, and provide potential candidates for the further development of anti-Alzheimer and antidiabetic diseases.

Optimization of Phenolic Compounds Extraction of Different Parts of Camu-camu Fruit from Different Geographic Regions.

Phenolic compounds in camu-camu (Myrciaria dubia) have received interest due to their health-promoting effects. However, these compounds have been poorly investigated in the different parts of the camu-camu fruit (pulp, peel, and seeds). This study aimed to optimize the solvent composition for extraction of phenolic compounds from pulp, peels, and seeds of camu-camu through a simplex-centroid mixture design. Then, the profile of phenolic compounds in samples of camu-camu pulp, peels, and seeds from different regions in Brazil and South America was determined by UPLC-ESI-MS/MS. Aqueous ethanol (80%, v/v) yielded the highest extraction for the pulp and peel, while aqueous methanol (50%, v/v) was selected for the seed. Camu-camu parts had p-coumaric acid, catechin, epicatechin, luteolin, rutin, and quercetin, with catechin as the major compound in the pulp, peels, and seeds of all the evaluated samples. The peel showed lower concentrations of these compounds compared with the pulp and the seed; the content of phenolic compounds also differed according to the geographic region. These results broaden the knowledge on phytochemical extraction and composition of camu-camu pulp, peel, and seed and may guide future applications of their extracts in the food industry.

Phytochemical Profile and Herbicidal (Phytotoxic), Antioxidants Potential of Essential Oils from Calycolpus goetheanus (Myrtaceae) Specimens, and in Silico Study.

The essential oil (EO) of Calycolpus goetheanus (Myrtaceae) specimens (A, B, and C) were obtained through hydrodistillation. The analysis of the chemical composition of the EOs was by gas chromatography coupled with mass spectrometry CG-MS, and gas chromatography coupled with a flame ionization detector CG-FID. The phytotoxic activity of those EOs was evaluated against two weed species from common pasture areas in the Amazon region: Mimosa pudica L. and Senna obtusifolia (L.) The antioxidant capacity of the EOs was determined by (DPPH•) and (ABTS•+). Using molecular docking, we evaluated the interaction mode of the major EO compounds with the molecular binding protein 4-hydroxyphenylpyruvate dioxygenase (HPPD). The EO of specimen A was characterized by ß-eudesmol (22.83%), (E)-caryophyllene (14.61%), and γ-eudesmol (13.87%), while compounds 1,8-cineole (8.64%), (E)-caryophyllene (5.86%), δ-cadinene (5.78%), and palustrol (4.97%) characterize the chemical profile of specimen B's EOs, and specimen C had α-cadinol (9.03%), δ-cadinene (8.01%), and (E)-caryophyllene (6.74%) as the majority. The phytotoxic potential of the EOs was observed in the receptor species M. pudica with percentages of inhibition of 30%, and 33.33% for specimens B and C, respectively. The EOs' antioxidant in DPPH• was 0.79 ± 0.08 and 0.83 ± 0.02 mM for specimens A and B, respectively. In the TEAC, was 0.07 ± 0.02 mM for specimen A and 0.12 ± 0.06 mM for specimen B. In the results of the in silico study, we observed that the van der Waals and hydrophobic interactions of the alkyl and pi-alkyl types were the main interactions responsible for the formation of the receptor-ligand complex.

Antioxidant capacity of Myrciaria cauliflora seed extracts by spectrophotometric, biochemical, and electrochemical methods and its protective effect against oxidative damage in erythrocytes.

This study aimed to investigate the antioxidant activity of extracts obtained from jabuticaba (Myrciaria cauliflora) seeds. Ethanolic (ETJS), methanolic (MEJS), aqueous (AQJS), and propanone (PRJS) extracts was assessed by measuring spectrophotometrically their ability to scavenge DPPH· , ABTS·+ , HOCl, and O2 ·- radicals. Electrochemical methods were employed, and the obtained data presented a good correlation with the radical scavenging results. The extracts were also able to attenuate lipid peroxidation induced by Fe2+ ions in phospholipids due to their chelation ability. The extracts protected human erythrocytes against oxidative cellular damage caused by AAPH, which was confirmed by using FESEM analysis. PRJS extract demonstrated the highest effect in all assays used in this work. Our findings prove that jabuticaba seeds are an important source of antioxidants which act by different mechanisms. This study opens new frontiers regarding the use of this fruit byproduct as a food additive. PRACTICAL APPLICATIONS: Jabuticaba seeds are usually discarded as waste by food industries, but they are rich in bioactive products and present interesting biological properties. Herein, we demonstrated that their extracts show remarkable antioxidant power against different reactive oxygen species, which are involved in several human pathologies. In this way, this by-product can be further used in the development of products to protect the human body against diseases related to oxidative stress.

(+)- and (-)-Xanthostones A-D: Four Pairs of Enantiomeric Cinnamoyl-ß-Triketone Derivatives from Xanthostemon chrysanthus.

Four pairs of cinnamoyl-ß-triketone derivative enantiomers, (+)- and (-)-xanthostones A-D ((+)- and (-)-1-4), were isolated from Xanthostemon chrysanthus. Compounds 1 and 2 feature a new rearranged cinnamoyl-phloroglucinol scaffold fused with a cinnamyl-ß-triketone framework. Compounds 1, 3, and 4 are the first examples of natural products with a peculiar phenethyl-pyranone acid unit. Their structures with absolute configurations were determined by spectroscopic data, X-ray diffraction analysis and electronic circular dichroism (ECD) calculation. Interestingly, these novel compounds showed a tautomeric behavior in solution, which was revealed by NMR spectroscopy and density functional theory calculation. A plausible biosynthetic pathway toward xanthostones A-D was proposed. Additionally, the anti-inflammatory and antibacterial activities of xanthostones A-D were evaluated.