Search Results (39)

Helianthemum nummularium (HN) and Helianthemum oelanticum subsp. incanum (HO) are plant species, among Cistaceae, that are highly distributed in the Mediterranean region. In the current study, extracts of the aerial parts from both species have been analyzed phytochemically. The non-polar extract analysis resulted in the identification of 15 compounds in each species, mainly terpene and fatty acid derivatives, through GC–MS. The methanolic extract analysis, conducted through UHPLC–MS/MS, led to the identification of 39 metabolites in HN and 29 in HO, respectively, the majority of which were phenolics. Among the identified compounds, several have also been isolated and structurally determined (from HN: rutin, linoleic acid, gallic acid, and isoquercetin, and from HO: quercetin-3-O-(2″-O-galloyl)-galactopyranoside, methyl gallate, catechin-3-O-glucopyranoside, and astragalin, while hyperoside, and cis- and trans-tiliroside have been determined in both species). Furthermore, the methanolic extracts of HN and HO displayed a high total phenolic content (177.2 mg GA/g extract and 150.6 mg GA/g extract, respectively) and considerable free-radical scavenging activity against the DPPH radical (94.6% and 94.0% DPPH inhibition, respectively). Antimicrobial testing showed stronger inhibition of HN against Gram (+) bacterial strains (MIC values 0.07–0.15 mg/mL), while both extracts exhibited low tyrosinase-inhibitory activity. Considering the lack of studies conducted on the chemistry and biological activities of the genus Helianthemum, the chemical characterization of extracts could contribute to new sources of bioactive metabolites to be explored and exploited for further potential applications such as food and/ or the cosmetic industry. Full article

Native and exotic fruits from the Amazon have varied characteristics, with aroma being a decisive factor in their acceptance for medicinal use as a nutraceutical supplement. This work aimed to analyze the chemical constituents of the volatile concentrates of some Myrtaceous fruit species sampled in the Brazilian Amazon. The fruit’s pulps were subjected to simultaneous distillation–extraction, and gas chromatography–mass spectrometry was used to analyze their volatile chemical composition. In the volatile concentrate of Eugenia stipitata (Araçá-boi) α-pinene (17.5%), citronellyl butanoate (15.6%), and pogostol (13.5%) were identified as primary constituents; Eugenia uniflora (Ginja) concentrate comprised curzerene (30.5%), germacrone (15.4%), atractylone (13.1%), and (E)-β-ocimene (11.1%); in Myrciaria dubia (Camu-Camu), α-pinene (55.8%), (E)-β-ocimene (13.1%), and α-terpineol (10.0%) were present; in Psidium guajava (Goiaba) were (2E)-hexenal (21.7%), hexanal (15.4%), caryophylla-4(12),8(13)-dien-5-β-ol (10.5%), caryophyllene oxide (9.2%), and pogostol (8.3%); and in Psidium guineense (Araçá), limonene (25.2%), ethyl butanoate (12.1%), epi-β-bisabolol (9.8%), and α-pinene (9.2%) were the main constituents. The analyzed volatile concentrates of these fruit species presented a significant diversity of constituents with a predominance of functional groups, such as monoterpenes, sesquiterpenes, and fatty acid derivatives, originating from the plant’s secondary metabolism and playing an important role in their nutritional and medicinal uses. Full article

Piper aduncum L. is widely distributed in tropical regions and the ethnobotanical uses of this species encompass medicinal applications for the treatment of respiratory, antimicrobial, and gynecological diseases. Chemical studies reveal a diverse array of secondary metabolites, including terpenes, flavonoids, and prenylated compounds. Extracts from P. aduncum have shown antibacterial, antifungal, and larvicidal activities. Our study explores the activity of extracts and partitions against Mycobacterium tuberculosis H37Rv, as well as the chemical diversity of the bioactive partition. This marks the first investigation of the bioactive partition of P. aduncum from agroecological cultivation. The ethyl acetate partition from the ethanolic leaf extract (PAEPL) was found to be the most active. PAEPL was subjected to column chromatography using Sephadex LH-20 and the obtained fractions were analyzed using UHPLC-HRMS/MS. The MS/MS data from the fractions were submitted to the online GNPS platform for the generation of the molecular network, which displayed 1714 nodes and 167 clusters. Compounds were identified via manual inspection and different libraries, allowing the annotation of 83 compounds, including flavonoids, benzoic acid derivatives, glycosides, free fatty acids, and glycerol-esterified fatty acids. This study provides the first chemical fingerprint of an antimycobacterial sample from P. aduncum cultivated in an agroecological system. Full article

Under certain conditions, ultrasonic treatment of certain foods and ingredients can contribute to the appearance of an extraneous odor, which is not usual for them, especially in fat-containing products. Since the food sector uses high-intensity ultrasound to control the crystallization of fats, the development of foreign smells and secondary fat oxidation products may impact the quality and safety of such items. In this work, we studied the volatile compounds’ profiles of oleogels structured with individual fractions of beeswax using ultrasonic treatment. For this work, six samples of oleogels were obtained. Sunflower oil was used as a fatty base, and three fractions of beeswax were used as gelators: hydrocarbon fraction (>99%), monoester fraction (>95%), and a mixture fraction of wax di- and triesters (10.1%), free fatty acids (40.1%), and free fatty alcohols (49.8%). The influence of ultrasonic treatment on the properties of oleogels was assessed using light microscopy in polarized light, texture analysis, gas chromatography with flame ionization, and mass spectrometric detection. Ultrasonic treatment affected the crystallization of oleogels and led to the formation of smaller crystals. At the same time, sonication led to both an increase and a decrease in the firmness of oleogels, depending on the composition of the gelator. As regards volatile compounds, a total of 121 fragrant substances were identified in all samples, including such groups as alkanes, alkenes, alkadienes, alkynes, alkadiynes, alcohols, ketones, aldehydes, terpenes, alkyl alkane, and alkyl benzene derivatives. Ultrasonic treatment caused formation of new volatile unsaturated compounds. Some of them are known to have an unpleasant odor and thus might be responsible for the extraneous odor formation in studied fatty systems. Those were mainly (E)-2-octene, 1-heptene, 1,3-butadiene, and 1,3-octadiene in all oleogel samples. Sonicated samples B and C additionally had but-1-en-3-yne, pentenyne, and 1,3-butadiyne, whose odor can also be characterized as extraneous and distasteful. Several volatile compounds, supposed to be products of lipid oxidation, were also identified. Here we assume a reasonable approach is needed when selecting sonication conditions to prevent undesirable taste and flavor in oleogels and oleogel-based food products. Full article

The chemical composition of propolis varies between different types, due to the specific vegetation found near the hives and the climatic and soil conditions worldwide. Green propolis is exclusive to Brazil, produced by bees, with the resin of the plant Baccharis dracunculifolia. Brown propolis is a specific variety produced mainly in Northeast Brazil from the plant Hyptis divaricata, also known as “maria miraculosa”. Dark propolis is a variety of propolis produced by bees from the resin of the plant known as Jurema Preta (Mimosa hostilis benth). In this study, the aqueous extracts of green, brown, and dark propolis were analyzed for their antioxidant capacity using ABTS, FRAP, and DPPH, and their chemical profiles were determined using paper spray mass spectrometry. Among the three extracts, green propolis had the highest content of total phenolic compounds (2741.71 ± 49.53 mg GAE. 100 g⁻¹), followed by brown propolis (1191.55 ± 36.79 mg GAE. 100 g⁻¹), and dark propolis had the lowest content (901.79 ± 27.80 mg GAE. 100 g⁻¹). The three types of propolis showed high antioxidant capacity, with green showing the highest antioxidant capacity for the three methods used. Using paper spray mass spectrometry, it was possible to suggest the presence of 116 substances, including flavonoids (56), phenylpropanoids (30), terpenes (25), carboxylic acids (1), benzoic acid derivatives (1), fatty acids (1), amino acids (1) and alkaloids (1). The compounds in the green, brown, and dark propolis extracts reinforce the bioactive potential for application in these tree extracts’ food and pharmaceutical products. Full article

Cladostephus spongiosus was harvested once a month during its growing season (from May to August) from the Adriatic Sea. Algal volatile organic compounds (VOCs) were obtained by headspace solid-phase microextraction (HS-SPME) and hydrodistillation (HD) and analysed by gas chromatography and mass spectrometry (GC-MS). The effects of air drying and growing season on VOCs were determined. Two different extraction methods (ultrasound-assisted extraction (UAE) and microwave-assisted extraction (MAE)) were used to obtain ethanolic extracts of C. spongiosus. In addition, the seasonal antioxidant potential of the extracts was determined, and non-volatile compounds were identified from the most potent antioxidant extract. Aliphatic compounds (e.g., pentadecane) were predominantly found by HS-SPME/GC-MS. Hydrocarbons were more than twice as abundant in the dry samples (except in May). Aliphatic alcohols (e.g., hexan-1-ol, octan-1-ol, and oct-1-en-3-ol) were present in high percentages and were more abundant in the fresh samples. Hexanal, heptanal, nonanal, and tridecanal were also found. Aliphatic ketones (octan-3-one, 6-methylhept-5-en-2-one, and (E,Z)-octa-3,5-dien-2-one) were more abundant in the fresh samples. Benzene derivatives (e.g., benzyl alcohol and benzaldehyde) were dominant in the fresh samples from May and August. (E)-Verbenol and p-cymen-8-ol were the most abundant in dry samples in May. HD revealed aliphatic compounds (e.g., heptadecane, pentadecanal, (E)-heptadec-8-ene, (Z)-heptadec-3-ene), sesquiterpenes (germacrene D, epi-bicyclosesquiphellandrene, gleenol), diterpenes (phytol, pachydictyol A, (E)-geranyl geraniol, cembra-4,7,11,15-tetraen-3-ol), and others. Among them, terpenes were the most abundant (except for July). Seasonal variations in the antioxidant activity of the ethanolic extracts were evaluated via different assays. MAE extracts showed higher peroxyl radical inhibition activity from 55.1 to 74.2 µM TE (Trolox equivalents). The highest reducing activity (293.8 µM TE) was observed for the May sample. Therefore, the May MAE extract was analysed via high-performance liquid chromatography with high-resolution mass spectrometry and electrospray ionisation (UHPLC-ESI-HRMS). In total, 17 fatty acid derivatives, 9 pigments and derivatives, and 2 steroid derivatives were found. The highest content of pheophorbide a and fucoxanthin, as well as the presence of other pigment derivatives, could be related to the observed antioxidant activity. Full article

Despite ongoing control efforts, the mosquito population and diseases vectored by them continue to thrive worldwide, causing major health concerns. There has been growing interest in the use of botanicals as alternatives to insecticides due to their widespread insecticidal properties, biodegradability, and adaptability to ecological conditions. In this study, we investigated the larvicidal activity and cytotoxicity effects of solvent extracts from three aromatic plants—Curcuma longa (turmeric), Ocimum americanum (hoary basil), and Petroselinum crispum (parsley)—against Aedes albopictus. Subsequently, we examined the phytochemical composition of the extracts through gas chromatography–mass spectrometry (GC–MS) analysis. Results revealed that the hexane extracts of O. americanum and P. crispum exhibited the greatest larvicidal activity with the lowest median lethal concentration (LC₅₀) values (<30 µg/mL) at 24 h post-treatment, with the former found to be significantly less toxic towards African monkey kidney (Vero) cells. The GC–MS analysis of the said extract indicated the presence of different classes of metabolites, including phenylpropanoids, very long-chain alkanes, fatty acids and their derivatives, and terpenes, with the most abundant component being methyl eugenol (55.28%), most of which, have been documented for their larvicidal activities. These findings provide valuable insights into the potential use and development of bioinsecticides, particularly from O. americanum. Full article

The wood of Michelia macclurei Dandy (MD) is an excellent material that is widely used in the furniture, handicraft, and construction industries. However, less research has been conducted on the chemical composition and biological activity of heartwood, which is the main valuable part of the wood. This study aimed to investigate the chemical composition and biological activities of the heartwood of Michelia macclurei Dandy (MDHW) and to confirm the active ingredients. Triple quadrupole gas chromatography–mass spectrometry (GC-MS) was used to characterize the volatile components of MDHW, while ultra-performance liquid chromatography–mass spectrometry was used to analyze the non-volatile components (UPLC-MS). The total reducing power, 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical, and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) radical scavenging assays, acetylcholinesterase and α-glucosidase inhibition assays, and an antimicrobial test of 4 gram bacteria were used to describe the in vitro bioactivities. The GC-MS analysis showed that the volatile components of MDHW were mainly fatty compounds and terpenoids, with sesquiterpenes and their derivatives dominating the terpene composition. β-elemene was the main terpene component in the steam distillation (11.88%) and ultrasonic extraction (8.2%) methods. A total of 67 compounds, comprising 45 alkaloids, 9 flavonoids, 6 lignans, and others, were found by UPLC-MS analysis. The primary structural kinds of the non-volatile components were 35 isoquinoline alkaloids. Alkaloids were the predominant active constituent in all MDHW extracts, including crude extracts, alkaloid fractions, and non-alkaloid fractions. These extracts all demonstrate some biological effects in terms of antioxidant, enzyme inhibition, and bacterial inhibition. The findings of this study show that MDHW is abundant in chemical structure types, has great bioactivity assessment, and has the potential to be used to create natural antioxidants, products that postpone Alzheimer’s disease and lower blood sugar levels and antibacterial agents. Full article

The discovery of heterogeneous catalysts synthesized in easy, sustainable ways for the valorization of olefins derived from renewable biomass is attractive from environmental, sustainability, and economic viewpoints. Here, an organic–inorganic hybrid catalyst formulated as [MoO₃(Hpto)]·H₂O (2), where Hpto = 5-(2-pyridyl-1-oxide)tetrazole, was prepared by a hydrolysis–condensation reaction of the complex [MoO₂Cl₂(Hpto)]∙THF (1). The characterization of 1 and 2 by FT-IR and Raman spectroscopies, as well as ¹³C solid-state NMR, suggests that the bidentate N,O-coordination of Hpto in 1 (forming a six-membered chelate ring, confirmed by X-ray crystallography) is maintained in 2, with the ligand coordinated to a molybdenum oxide substructure. Catalytic studies suggested that 2 is a rare case of a molybdenum oxide/organic hybrid that acts as a stable solid catalyst for olefin epoxidation with tert-butyl hydroperoxide. The catalyst was effective for converting biobased olefins, namely fatty acid methyl esters (methyl oleate, methyl linoleate, methyl linolenate, and methyl ricinoleate) and the terpene limonene, leading predominantly to the corresponding epoxide products with yields in the range of 85–100% after 24 h at 70 °C. The versatility of catalyst 2 was shown by its effectiveness for the oxidation of sulfides into sulfoxides and sulfones, at 35 °C (quantitative yield of sulfoxide plus sulfone, at 24 h; sulfone yields in the range of 77–86%). To the best of our knowledge, 2 is the first molybdenum catalyst reported for methyl linolenate epoxidation, and the first of the family [MoO₃(L)_x] studied for methyl ricinoleate epoxidation. Full article

This study aimed to establish the phytochemical profile of Glochidion velutinum and its cytotoxic activity against prostate cancer (PC-3) and breast cancer (MCF-7) cell lines. The phytochemical composition of G. velutinum leaf extract and its fractions was established with the help of total phenolic and flavonoid contents and LC-MS/MS-based metabolomics analysis. The crude methanolic extract and its fractions were studied for pharmacological activity against PC-3 and MCF-7 cell lines using the MTT assay. The total phenolic content of the crude extract and its fractions ranged from 44 to 859 µg GAE/mg of sample whereas total flavonoid contents ranged from 20 to 315 µg QE/mg of sample. A total of forty-eight compounds were tentatively dereplicated in the extract and its fractions. These phytochemicals included benzoic acid derivatives, flavans, flavones, O-methylated flavonoids, flavonoid O- and C-glycosides, pyranocoumarins, hydrolysable tannins, carbohydrate conjugates, fatty acids, coumarin glycosides, monoterpenoids, diterpenoids, and terpene glycosides. The crude extract (IC₅₀ = 89 µg/mL), the chloroform fraction (IC₅₀ = 27 µg/mL), and the water fraction (IC₅₀ = 36 µg/mL) were found to be active against the PC-3 cell line. However, the crude extract (IC₅₀ = 431 µg/mL), the chloroform fraction (IC₅₀ = 222 µg/mL), and the ethyl acetate fraction (IC₅₀ = 226 µg/mL) have shown prominent activity against breast cancer cells. Moreover, G. velutinum extract and its fractions presented negligible toxicity to normal macrophages at the maximum tested dose (600 µg/mL). Among the compounds identified through LC-MS/MS-based metabolomics analysis, epigallocatechin gallate, ellagic acid, isovitexin, and rutin were reported to have anticancer activity against both prostate and breast cancer cell lines and might be responsible for the cytotoxic activities of G. velutinum extract and its bioactive fractions. Full article

The volatile organic compounds (VOCs) of fresh (FrCC) and air-dried (DrCC) Cystoseria corniculata and fresh (FrEA) and air-dried (DrEA) Ericaria amentacea from the Adriatic Sea were investigated by headspace solid-phase microextraction (HS-SPME) and hydrodistillation (HD) and analysed by gas chromatography and mass spectrometry (GC-MS). In HS-FrCC and HS-DrCC, aliphatic compounds were dominant, with decan-5-ol as the most abundant in HS-FrCC, but in HS-DrCC pentadecane dominated. Monoterpenes (β-cyclocitral, β-citral, and β-cyclohomocitral) and sesquiterpenes (cubenol) were abundant in HS-FrCC. Notable differences between fresh and air-dried samples were found for benzene derivatives. Fatty acids and their derivatives were the most abundant in HD-FrCC and HD-DrCC. In HS-FrEA and HS-DrEA, saturated aliphatic compounds as well as unsaturated aliphatic compounds (particularly hexan-1-ol and (Z)-hex-3-en-1-ol) predominantly showed decrements after drying. Pentadecane, heptadecane, pentadecanal, and hexan-1-ol were predominant in HD-FrEA, and their percentage decreased in HD-DrEA. The percentage of monoterpenes decreased after drying, but the percentages of diterpenes and especially sesquiterpenes increased. δ-Selinene was the major terpene and the most abundant in HD-DrEA. A significant increment after drying could be noticed for fatty acids and their derivatives. The great diversity of identified VOCs among these two macroalgae supports their different botanical classifications. Full article

Xinyang Maojian (XYMJ) is one of the premium green teas and originates from Xinyang, which is the northernmost green tea production area in China. The special geographic location, environmental conditions, and manufacturing process contribute to the unique flavor and rich nutrition of XYMJ green tea. Aroma is an important quality indicator in XYMJ green tea. In order to illustrate the aroma of XYMJ green tea, the key odorants in XYMJ green tea and their dynamic changes during the manufacturing processes were analyzed by headspace solid-phase microextraction (HS-SPME) combined with gas chromatography-mass spectrometry (GC-MS). A total of 73 volatile compounds of six different chemical classes were identified in the processed XYMJ green tea samples, and the manufacturing processes resulted in the losses of total volatile compounds. Among the identified volatile compounds, twenty-four aroma-active compounds, such as trans-nerolidol, geranylacetone, nonanal, (+)-δ-cadinene, linalool, (Z)-jasmone, cis-3-hexenyl butyrate, cis-3-hexenyl hexanoate, methyl jasmonate, and β-ocimene, were identified as the key odorants of XYMJ green tea based on odor activity value (OAV). The key odorants are mainly volatile terpenes (VTs) and fatty acid-derived volatiles (FADVs). Except for (+)-δ-cadinene, copaene, cis-β-farnesene, (Z,E)-α-farnesene and phytol acetate, the key odorants significantly decreased after fixing. The principal coordinate analysis (PCoA) and the hierarchical cluster analysis (HCA) analyses suggested that fixing was the most important manufacturing process for the aroma formation of XYMJ green tea. These findings of this study provide meaningful information for the manufacturing and quality control of XYMJ green tea. Full article

The aim of this study was to investigate the effects of crude extracts of β-glucosidase from Issatchenkia terricola SLY-4, Pichia kudriavzevii F2-24 and Metschnikowia pulcherrima HX-13 (termed as SLY-4E, F2-24E and HX-13E) on the flavor complexity and typicality of Cabernet Sauvignon wines. The grape must was fermented using Saccharomyces cerevisiae with single or mixed SLY-4E, F2-24E and HX-13E. The physicochemical characteristics, volatile aroma compounds, total anthocyanins and sensory attributes of the wines were determined. Adding SLY-4E, F2-24E and HX-13E in wines resulted in a decrease in the anthocyanin content, total acids and volatile acids in wines but an increase in the content of terpenes, benzene derivatives, higher alcohols and esters, which may enhance wine sensory qualities and result in loss of wine color. Different adding strategies of β-glucosidase led to a variety of effects on wine aroma. S/H/F-Ew significantly increased the content of benzene derivatives, higher alcohols and long-chain fatty acid esters, which enhanced the fruity and floral flavor of wines. F2-24E significantly increased the content of short- and medium-chain fatty acid esters, acetate esters and carbonyl compounds. The results indicated that the mixed addition of non-Saccharomyces crude extracts and co-fermentation with S. cerevisiae could further improve wine flavor quality. Full article

High-pressure pre-treatment followed by supercritical carbon dioxide (ScCO₂) extraction (300 bar, 40 °C) was applied for the attainment of the lipophilic fraction of microalga Tetradesmus obliquus. The chemical profile of supercritical extracts of T. obliquus was analyzed by ultra-high-performance liquid chromatography–high-resolution mass spectrometry with electrospray ionization (UHPLC-ESI-HRMS). Moreover, the impact of ScCO₂ on the microbiological and metal profile of the biomass was monitored. The application of the pre-treatment increased the extraction yield approximately three-fold compared to the control. In the obtained extracts (control and pre-treated extracts), the identified components belonged to triacylglyceroles, fatty acid derivatives, diacylglycerophosphocholines and diacylglycerophosphoserines, pigments, terpenes, and steroids. Triacylglycerols (65%) were the most dominant group of compounds in the control extract. The pre-treatment decreased the percentage of triacylglycerols to 2%, while the abundance of fatty acid derivatives was significantly increased (82%). In addition, the pre-treatment led to an increase in the percentages of carotenoids, terpenoids, and steroids. Furthermore, it was determined that ScCO₂ extraction reduced the number of microorganisms in the biomass. Considering its microbiological and metal profiles, the biomass after ScCO₂ can potentially be used as a safe and important source of organic compounds. Full article

The present research is a comprehensive investigation of Dasycladus vermicularis (Scopoli) Krasser 1898 from the Adriatic Sea (Croatia) regarding volatilome–volatile organic compounds (VOCs, mostly nonpolar compounds) and less polar nonvolatile compounds for the first time. Headspace solid-phase microextraction (HS-SPME) and hydrodistillation (HD) were used showing the great volatilome variability among fresh (HS-FrDV and HD-FrDV) and dried (HS-DrDV and HD-DrDV) samples after GC–MS analysis. Aromatic aldehydes were dominant in both fresh and air-dried HS samples with benzaldehyde as the most abundant in fresh samples and decreasing 2.7–3.7 times after drying together with 2-phenylbut-2-enal that was not present after drying. Aliphatic compounds (unsaturated hydrocarbons in HS-FrDV; saturated hydrocarbons in HS-DrDV) were also present. C₁₁-hydrocarbons (dictyopterpene C’ and dictyopterpene D’) were detected in HS-FrDV. (E)-Phytol was the most dominant compound in HD-FrDV and HD-DrDV. Diterpene alcohols (cembra-4,7,11,15-tetraen-3-ol and (Z)-falcarinol) and sesquiterpene alcohol, cubenol, were dominant in HD-FrDV, and their abundance decreased after drying. C₁₃-norisoprenoides (α-ionone and β-ionone) increased after drying. Aliphatic compounds were present in both HD-FrDV and HD-DrDV samples. The less polar nonvolatile compounds in the obtained fractions F3 and F4 were analysed and identified by UHPLC-ESI(+)-HRMS. Identified compounds belonged to a group of pigments (7 compounds), fatty acid derivatives (13 compounds), as well as steroids and terpenes (10 compounds). Porphyrin-based compounds (C₅₅H₇₄N₄O_5–7), xanthophylls, sphingolipid compounds, fatty acid amides, and phytosterols represented the majority of identified compounds. By implementing both in vitro and in vivo assays for antioxidant activity determination, F3 showed a higher activity than F4. Inhibitory concentrations (IC₅₀) for F3 and F4 were 498.00 ± 0.01 µg/mL and 798.00 ± 0.81 µg/mL, respectively, while a 1.5-fold reduction in the ROS level was observed after pre-treatment of zebrafish larvae with 45 µg/mL of F3. Full article