RESUMO
Photoaging is widely regarded as the most significant contributor to skin aging damage. It is triggered by prolonged exposure to ultraviolet (UV) light and typically manifests as dryness and the formation of wrinkles. Nutritional intervention is a viable strategy for preventing and treating skin photoaging. In previous studies, we demonstrated that α-ionone had ameliorating effects on photoaging in both epidermal keratinocytes and dermal fibroblasts. Here, we investigated the potential anti-photoaging effects of dietary α-ionone using a UVB-irradiated male C57BL/6N mouse model. Our findings provided compelling evidence that dietary α-ionone alleviates wrinkle formation, skin dryness, and epidermal thickening in chronic UVB-exposed mice. α-Ionone accumulated in mouse skin after 14 weeks of dietary intake of α-ionone. α-Ionone increased collagen density and boosted the expression of collagen genes, while attenuating the UVB-induced increase of matrix metalloproteinase genes in the skin tissues. Furthermore, α-ionone suppressed the expression of senescence-associated secretory phenotypes and reduced the expression of the senescence marker p21 and DNA damage marker p53 in the skin of UVB-irradiated mice. Transcriptome sequencing results showed that α-ionone modifies gene expression profiles of skin. Multiple pathway enrichment analyses on both the differential genes and the entire genes revealed that α-ionone significantly affects multiple physiological processes and signaling pathways associated with skin health and diseases, of which the p53 signaling pathway may be the key signaling pathway. Taken together, our findings reveal that dietary α-ionone intervention holds promise in reducing the risks of skin photoaging, offering a potential strategy to address skin aging concerns.
Assuntos
Norisoprenoides , Envelhecimento da Pele , Masculino , Camundongos , Animais , Proteína Supressora de Tumor p53/metabolismo , Camundongos Endogâmicos C57BL , Pele , Colágeno/metabolismo , Suplementos Nutricionais , Raios Ultravioleta/efeitos adversos , Camundongos Pelados , FibroblastosRESUMO
Sweet potato provides rich nutrients and bioactive substances for the human diet. In this study, the volatile organic compounds of five pigmented-fleshed sweet potato cultivars were determined, the characteristic aroma compounds were screened, and a correlation analysis was carried out with the aroma precursors. In total, 66 volatile organic compounds were identified. Terpenoids and aldehydes were the main volatile compounds, accounting for 59% and 17%, respectively. Fifteen compounds, including seven aldehydes, six terpenes, one furan, and phenol, were identified as key aromatic compounds for sweet potato using relative odor activity values (ROAVs) and contributed to flower, sweet, and fat flavors. The OR sample exhibited a significant presence of trans-ß-Ionone, while the Y sample showed high levels of benzaldehyde. Starch, soluble sugars, 20 amino acids, and 25 fatty acids were detected as volatile compounds precursors. Among them, total starch (57.2%), phenylalanine (126.82 ± 0.02 g/g), and fatty acids (6.45 µg/mg) were all most abundant in Y, and LY contained the most soluble sugar (14.65%). The results of the correlation analysis revealed the significant correlations were identified between seven carotenoids and trans-ß-Ionone, soluble sugar and nerol, two fatty acids and hexanal, phenylalanine and 10 fatty acids with benzaldehyde, respectively. In general, terpenoids and aldehydes were identified as the main key aromatic compounds in sweet potatoes, and carotenoids had more influence on the aroma of OR than other cultivars. Soluble sugars, amino acids, and fatty acids probably serve as important precursors for some key aroma compounds in sweet potatoes. These findings provide valuable insights for the formation of sweet potato aroma.
Assuntos
Ipomoea batatas , Norisoprenoides , Solanum tuberosum , Compostos Orgânicos Voláteis , Humanos , Compostos Orgânicos Voláteis/análise , Benzaldeídos , Ipomoea batatas/química , Carotenoides , Odorantes/análise , Terpenos , Aldeídos/análise , Açúcares , Ácidos Graxos , Fenilalanina , AmidoRESUMO
The present study aimed to explore the key volatile compounds (VCs) that lead to the formation of characteristic flavors in ripe Pu-erh tea (RIPT) fermented by Monascus purpureus (M. purpureus). Headspace solid-phase microextraction coupled with gas chromatography/mass spectrometry (HS-SPME-GC-MS), orthogonal partial least square-discriminant analysis (OPLS-DA) were employed for a comprehensive analysis of the VCs present in RIPT fermented via different methods and were further identified by odor activity value (OAV). The VCs 1,2-dimethoxybenzene, 1,2,3-trimethoxybenzene, (E)-linalool oxide (pyranoid), methyl salicylate, linalool, ß-ionone, ß-damascenone were the key characteristic VCs of RIPT fermented by M. purpureus. OAV and Gas chromatography-olfactometry (GC-O) further indicated that ß-damascenone was the highest contribution VCs to the characteristic flavor of RIPT fermented by M. purpureus. This study reveals the specificities and contributions of VCs present in RIPT under different fermentation methods, thus providing new insights into the influence of microorganisms on RIPT flavor.
Assuntos
Monascus , Norisoprenoides , Compostos Orgânicos Voláteis , Chá/química , Fermentação , Cromatografia Gasosa-Espectrometria de Massas/métodos , Odorantes/análise , Compostos Orgânicos Voláteis/análiseRESUMO
Four rare compounds (1-4), including one 1,4-epoxy-benzoxepane derivative and one ringed prenylated naphthoquinoid skeleton, as well as one isopimarane-type diterpenoid and one megastigmane-type glycoside, along with three known megastigmane-type glycosides (5-7) were isolated from the ethanol extracts of C. chinense. Their structures were determined on the basis of 1D, 2D NMR, HR-ESI-MS and DP4+ analysis. Meanwhile, the in vitro evaluation indicated that compound 2 and 6 exhibited excellent procoagulant activities, which can significantly shorten prothrombin time (PT) and activated partial thromboplastin time (APTT), respectively.
Assuntos
Lamiaceae , Norisoprenoides , Estrutura Molecular , Lamiaceae/química , Glicosídeos/químicaRESUMO
A new megastigmane glycoside, (1R,5R,6S,7E)-megastigman-3,9-dione-7-en-6,11-diol 11-O-ß-D-glucopyranoside (1), and a new organic acid glycoside, methyl (4 R)-4-O-ß-D-glucopyranosyl-decanoate (2), together with eight known compounds (3-10), were isolated from the aerial parts of Artemisia halodendron Turcz. ex Bess. (Asteraceae). Their chemical structures were elucidated by 1 D and 2 D NMR and HR-ESI-MS spectra and DP4+ probability analysis. Among the identified compounds, compounds 5, 6 and 10 were isolated from the family Asteraceae, and compounds 3, 4 and 7-9 were identified from the genus Artemisia for the first time. All of the compounds were evaluated for their anticomplementary activity against the classical pathway (CP) and the alternative pathway (AP). Compounds 7 and 9 showed anticomplementary activity with the CH50 values of 0.31 ± 0.08 and 0.50 ± 0.09 mM, respectively.
Assuntos
Artemisia , Glicosídeos Cardíacos , Glicosídeos/farmacologia , Glicosídeos/química , Artemisia/química , Norisoprenoides/farmacologia , Norisoprenoides/química , Glucosídeos/química , Estrutura MolecularRESUMO
ETHNOPHARMACOLOGICAL RELEVANCE: Ziziphora clinopodioides subsp. bungeana (Juz.) Rech.f. is a subshrub that is widely distributed in China, Kazakhstan, Kyrgyzstan, Mongolia, Russia, Tajikistan, Turkmenistan, and Uzbekistan. The species is used in traditional medicine for the relief of symptoms connected to cardiovascular diseases like coronary heart disease or hypertension. AIM OF THE STUDY: was to validate traditional use of Z. clinopodioides subsp. bungeana for the treatment of coronary hearth diseases using in vivo models and to find active compounds responsible for the activity. MATERIALS AND METHODS: Multiple extracts were obtained from the aerial parts of Z. clinopodioides subsp. bungeana using maceration, liquid-liquid extraction, CO2 extraction and ultrasound-assisted extraction. Preliminary screening studies for the evaluation of the efficacy of Z. clinopodioides subsp. bungeana extracts on the model of hemic hypoxia were performed. The most effective samples were selected and included in the main study. Stage 2 of the study evaluated the cardiotropic activity of the selected extracts on a model of chronic heart failure. Preparations were administered to animals intragastrically once a day for 28 days. For the isolation of individual compounds plant material was extracted with 96% ethanol. The obtained crude extract was sequentially extracted with n-hexane and dichloromethane and separated by chromatography on a Diaion HP-20 column. The obtained fractions were further subjected to Sephadex LH-20 column chromatography and eluted isocratically with 96% ethanol (EtOH) to yield subfractions, which were further separated by preparative HPLC to obtain 13 individual compounds. RESULTS: Extracts obtained from Ziziphora clinopodioides subsp. bungeana (Juz.) Rech.f. herb were subjected to pharmacological screening for the evaluation of their efficacy on hemic hypoxia. Based on the obtained results, out of the sixteen tested extracts two (AR and US 60%) were selected for further evaluation of their cardiotropic activity. Modeling of chronic heart failure was carried out in accordance with the following stages: 1) anesthesia with chloral hydrate at a dose of 450 mg/kg, intraperitoneally, 2) artificial ventilation of the lungs, 3) thoracotomy, 4) modeling of permanent ischemic or ischemic-reperfusion damage. Both extracts effected the indicators of contraction and output, comparable to the reference drug - Monopril. Based on the extraction methods used to obtain RAF and US60 and data from the literature, it can be assumed that they contain compounds with medium polarity, including polyphenols and terpenoids. At the next stage three previously undescribed monoterpenoid derivatives - Ziziphoric acid (1), Ziziphoroside D (2) and 6'-malonylziziphoroside A (3), along with two previously described megastigmane glucosides - blumenol C glucoside (4), blumenol C 9-O-(6'-O-malonyl-beta-D-glucopyranoside (5) and two previously described monoterpenoids 7a-hydroxymintlactone (6), 7-hydroxypiperitone (7) together with six polyphenols - pinocembrine-7-O-rutinoside (8), chrysine-7-O-rutinoside (9), acacetin-7-O-rutinoside (10), luteolin-7-O-rutinoside (11), rutin (12) and rosmarinic acid (13) were isolated from Z. clinopodioides subsp. bungeana extracts. CONCLUSION: Our results support the traditional use of Z. clinopodioides subsp. bungeana for the treatment of coronary diseases. As a result of Z. clinopodioides subsp. bungeana extracts screening in vivo, two extracts were selected as potential cardiotropic agents. Phytochemical analysis of the plant material led to the isolation of five terpenoid derivatives, two megastigmane glycosides, five flavonoids and one cinnamic acid derivative, which could be responsible for the reported biological activity. Future experiments are required to understand the mechanisms of action for the isolated compounds.
Assuntos
Insuficiência Cardíaca , Lamiaceae , Animais , Norisoprenoides , Lamiaceae/química , Extratos Vegetais/farmacologia , Extratos Vegetais/uso terapêutico , Extratos Vegetais/análise , Polifenóis , Monoterpenos , HipóxiaRESUMO
The bulbs of Allium sativum known as garlic are widely used as food or seasoning. In China they have been used as a traditional Chinese medicine (TCM) since ancient times for the treatment of scabies, tuberculosis, pertussis, diarrhea and dysentery. A. sativum has reportedly shown platelet aggregation inhibition and has been used in the treatment of cardiovascular diseases. However, there are only few studies focussing on the aerial parts, which are normally discarded during harvest. In this study, two new ionone glycosides, dasuanxinosides D and E (1, 2: ), are isolated from the aerial parts together with 13 known compounds including alkanes derivatives and alkyl glycosides (3â-â15: ), which are reported for the first time from this plant. Their structures are identified by extensive NMR and HRMS analyses. The isolated compounds are evaluated for their inhibitory effect on adenosine diphosphate (ADP)-induced platelet aggregation in vitro.
Assuntos
Alho , Alho/química , Norisoprenoides/farmacologia , Glicosídeos/farmacologia , Agregação Plaquetária , Componentes Aéreos da PlantaRESUMO
There is a previously neglected influence of geochemical conditions on plant phytochemistry. In particular, high concentrations of dissolved salts can affect their biosynthesis of natural products. Detoxification is most likely an important aspect for the plant, but additional natural products can also give it an expanded range of bioactivities. During the phytochemical analysis a Palicourea luxurians plant collected in a sulfate-rich environment (near the Río Sucio, Costa Rica) showed an interesting natural product in this regard. The structure of this compound was determined using spectroscopic and computational methods (NMR, MS, UV, IR, CD, optical rotation, quantum chemical calculations) and resulted in a megastigmane sulfate ester possessing a ß-ionone core structure, namely blumenol C sulfate (1, C13H22O5S). The levels of sulfur and sulfate ions in the leaves of the plant were determined using elemental analysis and compared to the corresponding levels in comparable plant leaves from a less sulfate-rich environments. The analyses show the leaves from which we isolated blumenol C sulfate (1) to contain 35% more sulfur and 80% more sulfate than the other samples. Antimicrobial and antioxidant activities of compound 1 were tested against Escherichia coli, E. coli ampR and Bacillus subtilis as well as measured using complementary in vitro FRAP and ATBS assays, respectively. These bioactivities are comparable to those determined for structurally related megastigmanes. The sulfur and sulfate content of the plant leaves from the sulfate-rich environment was significantly higher than that of the other plants. Against this background of salt stress, we discuss a possible biosynthesis of blumenol C sulfate (1). Furthermore, there appears to be no benefit for the plant in terms of extended bioactivities. Hence, the formation of blumenol C sulfate (1) probably primarily serves the plant detoxification process.
Assuntos
Produtos Biológicos , Rubiaceae , Rubiaceae/química , Norisoprenoides/análise , Sulfatos/análise , Escherichia coli , Folhas de Planta/química , Produtos Biológicos/análise , Enxofre/análiseRESUMO
Twelve sesquiterpenoids with seven different carbon skeletons, including four isodaucanes (1-4), an aromadendrane (5), a guaiane (6), a cadalane (7), two eudesmanes (8 and 9), two bisabolanes (10 and 11), and a megastigmane (12), were isolated from the twigs and leaves of Aglaia lawii (Wight) C. J. Saldanha et Ramamorthy. Of these compounds, amouanglienoids A (1) and B (2) are new isodaucane sesquiterpenoids. This is the first report of isodaucanes from the genus Aglaia, and amouanglienoid A (1) represents the first isodaucane containing a Δ7(8) double bond. Their structures were discerned from extensive spectroscopic analyses, single-crystal X-ray diffraction, and comparison of the experimental and calculated ECD data. In in vitro bioassays, compounds 1, 10, and 11 showed potent inhibitory effects against lipopolysaccharide (LPS)-induced inflammation in BV-2 microglial cells, while compound 11 exhibited considerable inhibition of PTP1B with an IC50 value of 16.05 ± 1.09 µM.
Assuntos
Aglaia , Sesquiterpenos de Eudesmano , Sesquiterpenos , Aglaia/química , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Carbono , Lipopolissacarídeos , Estrutura Molecular , Sesquiterpenos Monocíclicos , Norisoprenoides , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Sesquiterpenos de Eudesmano/químicaRESUMO
We determined the allelopathic effects of crude organic (hexane, ethyl acetate, and methanol) extracts of the cyanobacterial Spirulina platensis on barnyardgrass (Echinochloa crus-galli (L.) Beauv.) and Chinese amaranth (Amaranthus tricolor L.). The crude ethyl acetate extract showed the highest inhibitory activity and was subsequently fractionated by column chromatography into 23 fractions based on thin-layer chromatography band pattern similarities. Four concentrations (2000, 1000, 500, and 250 ppm) of each fraction were tested for their allelopathic activity. Fractions E6 and E13 exhibited the most significant inhibitory effects against Chinese amaranth. The constituents of the highly active E6F3-E6F5 fractions determined by GC-MS, chromatography, and spectroscopy included the fatty acids, γ-linolenic acid 15, oleic acid 12, and predominantly palmitic acid 7; minor constituents included 2-ethyl-3-methylmaleimide 9 and C11 norisoprenoids (dihydroactinidiolide 10 and 4-oxo-ß-ionone 13). Isolation of E13 fraction by column chromatography revealed four C13 norisoprenoids: 3-hydroxy-ß-ionone 17, 3-hydroxy-5α,6α-epoxy-ß-ionone 18, 3-hydroxy-5ß,6ß-epoxy-ß-ionone 19, and loliolide 20. Their structures were elucidated by NMR spectroscopy. All six isolated norisoprenoids inhibited seed germination and seedling growth of Chinese amaranth at concentrations of 250-1000 ppm. Allelochemicals from S. platensis could be utilized in the development of novel bioactive herbicides.
Assuntos
Echinochloa , Spirulina , Alelopatia , Norisoprenoides/química , Extratos Vegetais/químicaRESUMO
INTRODUCTION: Annona muricata is a member of the Annonaceae family. This plant has a high concentration of acetogenin, which gives it excellent therapeutic property. Researchers have tested this miraculous herb in breast cancer cells treatment and observed that it could be a source of anti-cancer agents. The proposed study focused on screening the anticancer biological activity of Annona muricata plant by using the in vitro, in vivo, and in silico methods. METHODS: In in vitro analysis, the IC50 was determined on two-dimensional and three-dimensional breast cancer cells. 2D cells were cultured on flat dishes typically made of plastic, while 3D cells were cultured using the hanging drop method. In in vivo analysis, Drosophila melanogaster was preferred, and the LC50 was determined. In in silico analysis, molecular docking studies have been carried out on the different classes of Annona muricata acetogenins against the target proteins. Nearly, five acetogenins were selected from the literature, and docking was performed against human Bcl-2, Bad and Akt-1 proteins. RESULTS: In vitro and in vivo results revealed the IC50 value of 2D MDA-MB-231 cells as 330 µg.mâ-1, of 2D MCF-7 cells as290 µg.mâ-1, and of 3D MCF-7 and MDA-MB-231 cells about 0.005 g.mâ-1; the LC50 value of Drosophila melanogaster was determined as 0.1 g.mâ-1. In silico results revealed that the docked complex formed by Isoquercetin showed better binding affinity towards target proteins. CONCLUSION: As a result of the analysis, the Annona muricata plant has been observed to be effective against cancer and likely to be a potential drug.
Assuntos
Annona , Neoplasias da Mama , Acetogeninas/química , Acetogeninas/metabolismo , Animais , Annona/química , Annona/metabolismo , Aporfinas , Dioxóis , Drosophila melanogaster , Feminino , Glucosídeos , Humanos , Simulação de Acoplamento Molecular , Norisoprenoides , Extratos Vegetais/química , Plásticos/metabolismo , Proteínas Proto-Oncogênicas c-akt/metabolismo , Proteínas Proto-Oncogênicas c-bcl-2/metabolismo , Quercetina/análogos & derivadosRESUMO
The winemaking by-product grape marc (syn. pomace) contains significant quantities of latent flavour in the form of flavour precursors which can be extracted and used to modulate the volatile composition of wine via chemical hydrolysis. Varietal differences in grapes are widely known with respect to their monoterpene content, and this work aimed to extend this knowledge into differences due to cultivar in volatiles derived from marc precursors following wine-like storage conditions. Marc extracts were produced from floral and non-floral grape lots on a laboratory-scale and from Muscat Gordo Blanco marc on a winery -scale, added to a base white wine for storage over five to six months, before being assessed using a newly developed membrane-assisted solvent extraction gas chromatography-mass spectrometry (GC-MS) method. The geraniol glucoside content of the marc extracts was higher than that of juices produced from each grape lot. In all wines with added marc extract from a floral variety, geraniol glucoside concentration increased by around 150-200%, with increases also observed for non-floral varieties. The relative volatile profile from extracts of the floral varieties was similar but had varied absolute concentrations. In summary, while varietally pure extracts would provide the greatest control over flavour outcomes when used in winemaking, aggregated marc parcels from floral cultivars may provide a mechanism to simplify the production logistics of latent flavour extracts for use in the wine sector.
Assuntos
Vitis , Vinho , Aromatizantes/análise , Cromatografia Gasosa-Espectrometria de Massas , Glucosídeos/análise , Monoterpenos/análise , Norisoprenoides/análise , Extratos Vegetais/análise , Solventes/análise , Vitis/química , Vinho/análiseRESUMO
Phytochemical investigation of a methanolic extract of Sedum sarmentosum collected from Vietnam resulted in the isolation of a new megastigmane glucoside, named sedumoside K (1), together with 17 previously reported compounds (2-18). Structural elucidation of the new compound was achieved by HRFABMS, NMR spectroscopic analysis, acid hydrolysis and quantum ECD calculations. The absolute configuration of compounds 2-6 has been revised. The major isolates were tested for cytotoxic activity against HeLa human cervical cancer cells, and all showed moderate activities.
Assuntos
Antineoplásicos , Medicamentos de Ervas Chinesas , Sedum , Medicamentos de Ervas Chinesas/química , Humanos , Norisoprenoides/química , Compostos Fitoquímicos , Sedum/químicaRESUMO
(1) Background: Solid phase microextraction (SPME)-Arrow is a new extraction technology recently employed in the analysis of volatiles in food materials. Grape volatile organic compounds (VOC) have a crucial role in the winemaking industry due to their sensory characteristics of wine.; (2) Methods: Box-Behnken experimental design and response surface methodology were used to optimise SPME-Arrow conditions (extraction temperature, incubation time, exposure time, desorption time). Analyzed VOCs were free VOCs directly from grape skins and bound VOCs released from grape skins by acid hydrolysis.; (3) Results: The most significant factors were extraction temperature and exposure time for both free and bound VOCs. For both factors, an increase in their values positively affected the extraction efficiency for almost all classes of VOCs. For free VOCs, the optimum extraction conditions are: extraction temperature 60 °C, incubation time 20 min, exposure time 49 min, and desorption time 7 min, while for the bound VOCs are: extraction temperature 60 °C, incubation time 20 min, exposure time 60 min, desorption time 7 min.; (4) Conclusions: Application of the optimized method provides a powerful tool in the analysis of major classes of volatile organic compounds from grape skins, which can be applied to a large number of samples.
Assuntos
Produtos Agrícolas/química , Cromatografia Gasosa-Espectrometria de Massas/normas , Extratos Vegetais/análise , Microextração em Fase Sólida/normas , Vitis/química , Compostos Orgânicos Voláteis/análise , Ácidos/análise , Ácidos/isolamento & purificação , Álcoois/análise , Álcoois/isolamento & purificação , Temperatura Alta , Monoterpenos/análise , Monoterpenos/isolamento & purificação , Norisoprenoides/análise , Norisoprenoides/isolamento & purificação , Extratos Vegetais/isolamento & purificação , Compostos Orgânicos Voláteis/isolamento & purificação , Vinho/análiseRESUMO
Clinacanthus nutans Lindau (Family: Acanthaceae) is a medicinal herb widely distributed in the tropic and subtropic areas of Asia. C. nutans is traditionally consumed as vegetable or herbal tea, as well as a folk medicine for anticancer and antifungal activities. However, to date, chemical constituent responsible for observed health beneficial effects of this medicinal plant is not clear. In the current study, 32 compounds (1-32), including three new megastigmanes (1-3) were isolated from the aerial parts of C. nutans. Their structures were elucidated on the basis of comprehensive NMR, MS, and CD spectroscopic data analysis, as well as chemical hydrolysis. Among the isolates, cycloartane triterpenoids (9, 10, and 12) displayed moderate anti-proliferative effects against HepG2 cell growth with IC50 values ranging from 9.12 to 19.89 µM. Data obtained from flow cytometry analysis and western blotting assays revealed that compounds 9 and 12 induced apoptosis of HepG2 cells by modulating the expression of proteins associated to mitochondrial-mediated apoptotic pathway. Furthermore, megastigmanes 1, 2, 7, and 8 enhanced the anti-Candida albicans activity of amphotericin B (AmB), supporting the synergistic effects between megastigmanes and AmB. This is the first report of anticancer and antifungal potential of cycloartane triterpenoids and megastigmanes in C. nutans, which shed useful insights on the relationship between C. nutans's chemical constituent and its beneficial effects to health. Findings from this study support further development of this medicinal plant for potential pharmaceutical applications.
Assuntos
Acanthaceae/química , Antifúngicos/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Norisoprenoides/farmacologia , Triterpenos/farmacologia , Antifúngicos/isolamento & purificação , Antineoplásicos Fitogênicos/isolamento & purificação , Apoptose/efeitos dos fármacos , Candida albicans/efeitos dos fármacos , China , Células Hep G2 , Humanos , Estrutura Molecular , Norisoprenoides/isolamento & purificação , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Componentes Aéreos da Planta/química , Plantas Medicinais/química , Triterpenos/isolamento & purificaçãoRESUMO
Dee are a unique and rapidly growing part of the global snack food market and are recognised as having distinct sensory properties (taste and texture). In this study, the development of important volatile aroma compounds over storage was evaluated and their chemical origin explained. Sweet potatoes were batch fried in high oleic sunflower oil (HOSO) and subjected to accelerated shelf life testing. Headspace volatiles were analysed using SPME GC-MS and correlated with sensory perception. All the components (sweet potatoes, oil and ß-carotene) showed significant degradation after 3 weeks of storage at accelerated conditions (equivalent to 12 weeks in real-time at 25 °C). Marker volatiles associated with lipid oxidation such as hexanal, octanal, pentanal were identified, in addition to norisoprenoids from ß-carotene degradation such as ß-ionon, 5,6-epoxy-ß-ionone, dihydroactinidiolide (DHA) and ß-cyclocitral. The most prominent marker of lipid oxidation (hexanal) rapidly increased at week 1, whereas the carotene degradation makers did not rapidly increase until week 3 suggesting a delayed response. The frying temperature during the batch frying process of SPC was also shown to play a significant role in the sensory perception of the product over the shelf life. Overall, the results suggest that tight control of process variables and raw material design may enable extended shelf life and potentially enhanced health credentials for the product. These findings are unique to SPC, but also of value to the wider food industry.
Assuntos
Ipomoea batatas/anatomia & histologia , Metabolismo dos Lipídeos , Lipídeos , Paladar , beta Caroteno/metabolismo , Aldeídos/análise , Benzofuranos/análise , Culinária , Diterpenos , Indústria Alimentícia , Cromatografia Gasosa-Espectrometria de Massas , Temperatura Alta , Norisoprenoides/análise , Odorantes , Oxirredução , Sensação , Óleo de Girassol , Compostos Orgânicos Voláteis/análise , beta Caroteno/análiseRESUMO
Perovskones and hydrangenones are a family of structurally complex triterpenoids that were mainly isolated from the genus Salvia medicinal plants. These isoprenoids exhibit a broad range of biological activities, such as antitumor and antiplasmodial activities. Here, we report the collective total synthesis of perovskone, perovskones C, D, F, hydrangenone, and hydrangenone B. The key strategies in this work include the following: (1) an asymmetric photoenolization/Diels-Alder reaction was developed to construct a tricyclic ring bearing three contiguous quaternary centers, which was used to build the core icetexane skeleton; (2) a bioinspired Diels-Alder reaction of perovskatone D with trans-α-ocimene was applied to stereospecifically generate perovskones; (3) late-stage oxidations and ring forming steps were developed to synthesize perovskones and hydrangenones. Our synthetic work suggests that (1) perovskatone D may serve as the precursor of the biosynthesis of perovskones and (2) the formation of hydrangenone and hydrangenone B, containing a five-membered D ring, may involve an oxidative ring cleavage and ring regeneration process.
Assuntos
Norisoprenoides/síntese química , Norisoprenoides/metabolismo , Triterpenos/síntese química , Triterpenos/metabolismo , Reação de Cicloadição , Salvia/metabolismo , EstereoisomerismoRESUMO
Roasting, an important process to refine Wuyi Rock tea, could impart different types of aroma to the final products. This study focuses on the differences in aroma characteristics among three kinds of refined teas, named light fire (LF), moderate fire (MF), and high fire (HF). A combination of solid phase microextraction (SPME) and a switchable system between GC-O-MS and GC × GC-O-MS was utilized to identify the odorants. In total, 97 aroma-active compounds could be smelled at the sniffing port, comprising alcohols, aldehydes, ketones, esters, heterocycles, and terpenes. However, only 52 obtained r-OAV >1. Significant differences were uncovered by the application of principal component analysis (PCA) and partial least squares regression (PLSR). Thereby, MF and HF had a more similar aroma profile, while in LF samples, alcohols, aliphatic aldehydes and some ketones were responsible for the aroma profile, such as (E,E)-2,4-hexadienal, octanal, hexanal, (E,Z)-2,6-nonadienal, (E)-ß-ionone, 3-octen-2-one etc. Strecker aldehydes had a great impact on the aroma of MF, including 2-methylpropanal, 2-methylbutanal, 3-methylbutanal etc. Some N-heterocyclic compounds also affected the overall aroma, for instance, 6-methyl-2-ethylpyrazine. In HF, the majority of aroma compounds increased with increasing roasting temperature, especially N-heterocyclic compounds as well as furfural and 5-methyl-2-furancarboxaldehyde, which are all closely related to the Maillard reaction. Besides, 5-methyl-2-(1-methylethenyl)-4-hexen-1-ol, trans-linalooloxide and 2-nonanone also remarkably influenced the aroma of HF. In addition, it was supposed that most amino acids that participated in the Maillard reaction during roasting were decomposed from the compounds that combined with tea polyphenols and amino acids.
Assuntos
Cromatografia Gasosa-Espectrometria de Massas/métodos , Odorantes/análise , Folhas de Planta/química , Chá/química , Temperatura , Compostos Orgânicos Voláteis/análise , Álcoois , Aldeídos , Norisoprenoides , Polifenóis/análise , Olfato , Microextração em Fase SólidaRESUMO
As a worldwide popular drink, black tea has always been one of the main focuses of tea studies. However, few studies have addressed the flavor profiles and related components, and most researches were based on a single factor. This study investigated the effects of multiple brewing conditions (temperature, time, water/tea ratio, and particle size) on the phytochemicals (non-volatile and volatile compounds) and sensory profiles of black tea infusions through response surface methodology. The regression models describing the brewing of detected indexes were significant (p ≤ 0.01) and reliable (R2 ≥ 0.902). The particle size led to the greatest variation of non-volatile compounds and presented negative correlations, while the water/tea ratio affected the composition of volatile compounds the most. Meanwhile, through the addition of the selected aroma compounds (geraniol and ß-ionone), an enhancement of black tea infusion sweetness was observed, proved the existence of odor-taste interaction in black tea infusions.
Assuntos
Monoterpenos Acíclicos/química , Norisoprenoides/química , Percepção Gustatória , Chá/química , Cromatografia Líquida de Alta Pressão , Flavonoides/análise , Humanos , Fenóis/análise , Análise de Componente Principal , Chá/metabolismo , Temperatura , Compostos Orgânicos Voláteis/química , Água/químicaRESUMO
UV-C treatment is a commonly known technique to inactivate microorganisms. The objective of this work was to investigate the impact of UV-C treatment of grape must on the sensory characteristics of the resulting wine and on the profile of volatile compounds of grape must and wine. Different UV-C doses were applied to Riesling must and compared with thermal pasteurization. The sensory off-flavor "ATA" and a content of 0.5 µg/L 2-aminoacetophenone were determined in the grape must and in the resulting wine after UV-C treatment with a high dose of 21 kJ/L. Sensory off-flavors did neither occur after thermal pasteurization nor after UV-C treatment with a dose of 2 kJ/L, which is sufficient for the inactivation of microorganisms. Minor changes in the volatiles' profiles of grape must and wine, involving e.g. terpenes and C13-norisoprenoids, occurred in musts treated with thermal pasteurization as well as with a UV-C dose of 2 kJ/L.