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Bioactive compounds by UHPLC-MS/MS and molecular networking from Myrceugenia foveolata
Natural Product Research
Abstract
Myrceugenia foveolata, commonly known as 'guamirim', was analysed using UHPLC-MS/MS and molecular networking. Hydroalcoholic extracts of leaves and stem bark were obtained using ethanol:water (70:30) as solvent. Chemical composition of the extracts was identified using UHPLC-MS/MS and tested for antioxidant activity and growth inhibition against E. coli, S. aureus, L. monocytogenes and S. enterica. Ten compounds were tentatively identified in the extracts including myricitrin, quercitrin, and betulin (in leave extracts), and avicularin, kaemferol-3-O-arabinopyroniside, 2"-O-galloylquercitrin and the acid triterpenes ursolic, sumaresinolic, asiatic and maslinic (in both extracts). Both extracts showed similar antioxidant activities, phenolic composition, and growth inhibition. The most pronounced response was observed against L. monocytogenes, with a growth inhibition rate of 73% to leaves extract and 65% do stem bark extract.
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The species Eugenia involucrata DC. is a plant native to Brazil and is traditionally used for intestinal problems, however, little research has documented about its biological potential and phytochemical profile. Thus, the objective of this study was to carry out preliminary phytochemical prospecting, antimicrobial and antioxidant potential of E. involucrata extracts. Using the E. involucrata leaves, aqueous and organic extracts were obtained using the following solvents (ethanol, methanol, hexane, acetone, dichloromethane and ethyl acetate). The phytochemical prospecting detected the presence of saponins, steroids, flavonoids and tannins in the extracts. Ethanolic and methanolic extracts presented antimicrobial activity for most of the bacterial strains tested, as well as for yeast Candida albicans, with concentrations between 3.12 and 50 mg/mL. The ethanolic and metanolic extract presented high free radical sequestration potential (>90%). The methanol extract showed an IC50 value statistically equal to that found for the commercial antioxidant BHT (p <0.05). The crude extracts obtained with ethanol and methanol were the most promising. These results suggest that methanolic, ethanolic and aqueous extracts are a promising source of natural bioactive.
RESUMO Listeria monocytogenes é o agente causador da listeriose, uma grave doença de origem alimentar que causa severas infecções em humanos com altas taxas de mortalidade. O leite e seus derivados estão entre os produtos alimentícios mais frequentemente envolvidos na transmissão de L. monocytogenes. A listeriose acomete, sobretudo, indivíduos imunodeprimidos, grávidas, recém-nascidos e idosos, o que ressalta o caráter oportunista deste micro-organismo e sua importância para a saúde pública. No presente trabalho, faz-se uma revisão narrativa crítica sobre o risco à saúde humana decorrente da ingestão de leite e derivados contaminados por L. monocytogenes, bem como se discutem os fatores que determinam a contaminação por L. monocytogenes na cadeia de produção e distribuição de leite e derivados. São apresentados e avaliados os dados de ocorrência de L. monocytogenes em leite cru e em produtos lácteos no Brasil, tendo em vista seu potencial de envolvimento em casos de listeriose humana. Adicionalmente, são indicadas as principais áreas de pesquisa e atuação para prevenir a contaminação de L. monocytogenes em produtos lácteos.
Leaves of Eugenia Florida DC. have been used in folk medicine as hypotensive, hypoglycemic, antipyretic and for gastrointestinal disorders, among others. In this study dried leaves were extracted with ethanol and the extract was partitioned with hexane, CHCl3, EtOAc, BuOH and water to afford triterpenoid- and polyphenol-rich fractions which were analyzed by GC-MS and UFLC-DAD-ESI-Ion Trap-MSⁿ. All fractions were tested against the proliferation of leukemic K562 and human melanoma SK-Mel-28 cell lines and for their ability to scavenge DPPH radical. Twenty-nine compounds were fully identified (among triterpenic and phenolic acids, flavonol- and dihydroflavonol-monoglyclosides) based on mass fragmentation patterns and comparison to standards and/or literature data. The ability to scavenge DPPH radical resulted in the following order: BuOH ≈ EtOAc > crude extract ≈ Water >> CHCl3 >> hexane; with the two most active reaching half of the TBHQ control potency (EC50 6.59 ± 0.03 µg mL⁻¹). On testing against the proliferation of K562 and SK-Mel-28 cell lines, the most significant inhibitions were achieved on the former by the crude extract (IC50 12 µg mL⁻¹) and the hexane and EtOAc fractions at 15 µg mL⁻¹.
RESUMO Realizou-se o estudo morfológico e taxonômico dos táxons de Myrceugenia O. Berg (Myrtaceae) do Parque Nacional do Itatiaia e avaliou-se a utilização dos caracteres vegetativos e elementos florais como informação diagnóstica. O estudo consta de descrições, chave analítica, observações de campo efetuadas durante as coletas e levantamento de herbários. Foram assinalados para a area oito táxons: Myrceugenia alpigena (DC.) Landrum var. alpigena; M bracteosa (DC.) D. Legrand & Kausel; M campestris (DC.) D. Legrand & Kausel; M cucullata D. Legrand; M glaucescens var. latior Burret (Landrum); M miersiana (Gardner) D. Legrand & Kausel, M ovata var. regnelliana (O. Berg) Landrum e M seriatoramosa (Kiaersk.) D. Legrand & Kausel. Os caracteres diagnósticos considerados para os táxons foram forma da inflorescência, do botão floral, dos prófilos e lobos calicinais bem como presença e ausência de nervura intramarginal. Os caracteres vegetativos por si só não constituíram elementos suficientemente diagnósticos para os táxons ocorrentes na área. Foram registradas duas novas ocorrências para o estado do Rio de Janeiro: M campestris e M cucullata.
Myrceugenia euosma, a tree or shrubby species found in South America, particularly in Chile and the southern regions of Brazil, was the subject of investigation in this study. The primary aim was to examine the morphology of its fruit, seed, and seedling, as well as to elucidate the seed germination process. The fruit of M. euosma is identified as a berry, containing between 2 to 13 seeds. The seed exhibits a membranaceous tegument, with a small amount of mucilaginous endosperm, discernible only during germination. The embryo conforms to the typical characteristics observed in the subtribe Myrciinae. The resultant seedling is epigeal and phanerocotylar, with paracotyledons and simple, opposite eophylls. Germination commences within three to five days following the initiation of the test. Nearly all treatments yielded relatively high germination rates (approximately 72%), except for the paper roll substrate at 30°C (43%). Furthermore, it was observed that the species is capable of germinating in the absence of light. These findings suggest that M. euosma demonstrates minimal reproductive restrictions concerning germination.
Keywords: Myrciinae, Mixed Ombrophylous Forest, Araucaria forest
We have counted the currently known, described and accepted number of plant species as ca 374,000, of which approxi-mately 308,312 are vascular plants, with 295,383 flowering plants (angiosperms; monocots: 74,273; eudicots: 210,008). Global numbers of smaller plant groups are as follows: algae ca 44,000, liverworts ca 9,000, hornworts ca 225, mosses 12,700, lycopods 1,290, ferns 10,560 and gymnosperms 1,079. Phytotaxa is currently contributing more than a quarter of the ca 2000 species that are described every year, showing that it has become a major contributor to the dissemination of new species discovery. However, the rate of discovery is slowing down, due to reduction in financial and scientific support for fundamental natural history studies.
As obesity is a global health concern the demand for anti-obesity drugs is high. In this study, we investigated the anti-obesity effect of the dried branches and leaves of murta (Myrceugenia euosma Legrand, Myrtaceae). A methanol extract of the dried branches and leaves of murta inhibited adipogenesis in 3T3-L1 cells. Three known flavanones—cryptostrobin (1), pinocembrin (4), and 5,7-dihydroxy-6,8-dimethylflavanone (6), and three chalcones—2′,6′-dihydroxy-3′-methyl-4′-methoxychalcone (2), pinostrobin chalcone (3), and 2′,6′-dihydroxy-4′-methoxy-3′,5′-dimethylchalcone (5) were isolated from the active fraction. Structures of these compounds were identified using various spectral data. Each of these compounds also inhibited adipogenesis in 3T3-L1 cells. In particular, compound 3 was a more potent inhibitor of triglyceride accumulation than the positive control berberine. Gene expression studies revealed that treatment of 3T3-L1 cells with 3 lowers the expression levels of CCAAT/enhancer-binding protein α and peroxisome proliferator activator γ2 during adipogenesis without affecting cell viability. Treatment of 3T3-L1 cells with 3 reduced the expression levels of mRNAs encoding sterol regulatory element-binding protein 1c and several lipogenic enzymes, including fatty acid synthase and stearoyl CoA desaturase-1. These results indicate that the methanol extract and compounds isolated from the dried branches and leaves of murta exert their anti-obesity effects through the inhibition of adipogenesis.
The Eugenia pyriformis Cambess. species, Myrtaceae, also known by the popular name as uvaia was evaluated for its antimicrobial activity. Broth microdilution method was used to determine the Minimum Inhibitory Concentration (MIC) against selected pathogenic strains of bacteria, and fungi. Checkerboard method was used to evaluate the synergistic interactions of E. pyriformis with Vancomycin and Fluconazole. The leaf and stem crude extract showed for Gram-positive strains MIC values of 125 and 250 µg/ml and for leveduriform fungi MIC values ranging from 7.81 to 62.5 µg/ml. Ethyl acetate, hydroalcoholic fractions, and leaf acetonic extract showed MIC values between 62.5 and 125 µg/ml for Gram-positive strains. The ethyl acetate fraction and leaf acetonic extract showed MIC values ranging from 7.81 to 62.5 µg/ml for leveduriform fungi; the stem acetonic extract MIC value was 62.5 µg/ml against Gram-positive strains and MIC value of 7.81 µg/ml for leveduriform fungi. The combination of E. pyriformis with Vancomycin and Fluconazole showed synergistic activity for strains of Enterococcus faecalis, Candida albicans, Candida krusei and Candida parapsilosis with fractional inhibitory concentration indices (FICI) below of 0.5. The extracts and fractions of this medicinal plant were able to inhibit the growth of bacteria and fungi in vitro.
Searches for substances with antimicrobial activity are frequent and medicinal plants have been considered interesting by some researchers since they are frequently used in popular medicine as remedies for many infectious diseases. The aim of this study was to verify the antibacterial effect of ethanol extracts of 13 plants (Artemisia Herba Alba, Lavandula officinalis L., Matricaria Chamomilla, Eugenia caryophylata , Cistus salvifolius, Mentha suaveolens subsp. Timija, Thymus serpyllum L., Lippia citriodora, Cinnamomum Zeylanicum, Rosa centifolia, Thymus vulgaris L, Rosmarinus officinalis and Pelargonium graveolens) against Listeria monocytogenes and other pathogenic strains. These plants are used more for their therapeutic effects in the aromatization of the traditionally fermented dairy products. For this purpose, the agar well diffusion method was the antimicrobial susceptibility performed test. The major components of extracts tested were identified by gas chromatography coupled with mass spectrometry (GC/MS) analysis. The obtained results revealed in vitro anti-Listeria monocytogenes activities of all the extracts. Also, the extracts of clove, mint timija, cinnamon, cistus, rose, thyme, wild thyme, artemisia, rosemary, geranium and camomile presented in this order promises inhibitory capacity with MIC value between 0.25 mg/mL for clove extract and 6.75 mg/mL for camomile extract. On the other hand, the antimicrobial activity was mainly a function of their chemical composition, in particular in the nature of their major volatile compounds. This study thus confirmed the possibility of using these plants or some of their components in food systems to prevent the growth of foodborne bacteria and to extend the shelf-life of processed foods.
A b s t r a c t: The aim of this study was to assess the phytotoxic potential of leaves of Myrcia tomentosa, as well as to isolate and identify the main bioactive compounds. The results for the coleoptile and phytotoxicity bioassays indicated the ethyl acetate extract for the phyto-chemistry study, owing to the high activity and the maintenance of the activity at lower concentrations. This extract was chromatographed and subjected to 1 H NMR and 13 C NMR. Two major active compounds were isolated from the ethyl acetate extract of leaves of M. tomentosa: avicularin and juglanin. The fractions where these compounds were isolated showed potent inhibition of coleoptile growth. This paper is the first report on the pres-ence of the flavonoids avicularin and juglanin in species of Myrtaceae from Neotropical savanna and provides a basis for future studies on the bioprospecting of M. tomentosa.
Since Myrtaceae is considered a complex family concerning the taxonomic classification due to the elevated number of components, difficult morphologic differentiation, and relatively low amount of studies in area, this article describes the potentiality of classification using chemometrics applied to UPLC-qToF/MS-MS dataset for chemotaxonomy investigation of leaves of fifteen species from the genus Psidium, Plinia, Myrciaria, and Eugenia into the Myrtaceae family. The use of a multivariate tool was indispensable to detect marker compounds since an elevated number of information on chromatograms did not provide conclusive data. The results offered an adequate classification among genus and species, principally based on ellagic acid, catechin, epicatechin, isoquercitrin, quercitrin, reynoutrin, madecassic acid, asiatic acid, and morin, used as marker compounds. Therefore, the method was useful and permitted the satisfactory chemotaxonomic distinction among the genus.
Essential oils from Myrceugenia euosma, M. foveolata, M. pilotantha, M. myrtoides and M. oxysepala, collected in Southern Brazil, were analysed by GC and GC–MS. Seventy compounds were identified, representing 86–99% of the oil content of the investigated species. The oils from M. foveolata, M. pilotantha and M. myrtoides were characterized by cyclic sesquiterpenes (67–90%), mainly those from the germacrene cyclization pathway. M. foveolata showed a predominance of globulol (21.3%) and epi-globulol (17.8%), while in the oils from M. pilotantha and M. myrtoides, spathulenol (18.7% and 23.8%, respectively) was the most representative. The oil from M. oxysepala and M. euosma were found to be quite distinct from the other species. The oil of M. eousma showed a predominance of nerolidol (46.7%) and epi-globulol (33.4%), and that of M. oxysepala was made up mainly by oxygenated compounds (80.4%), being 29% terpenes and 51.4% aliphatic compounds, such as aldehydes (nonadecanal, 20.6%; dodecanal, 6.8%); methyl-ketones (2-tridecanone, 5.0%) and alcohols (n-undecanol, 4.5%). Copyright © 2002 John Wiley & Sons, Ltd.
A família das Myrtaceae no Rio Grande do Sul
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Exotic fruits and nuts of the new world
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