Search Results (23)

Caigua (Cyclanthera pedata (L.) Schrad.) is a traditional herbal remedy traditionally used in Latin America for its health benefits and to treat metabolic disorders, including diabetes. Despite interest in its herbal use, the phytochemical properties of caigua’s secondary metabolites are poorly known. This study aimed to isolate the main flavone glycosides from the leaves of caigua landrace cultivated in the Camonica Valley (Italy) using flash chromatography and evaluate their potential activity toward peroxisome proliferator-activated receptors (PPARs) and transient receptor potential (TRP) ion channels through luciferase and intracellular calcium assays. We found that the caigua species-specific flavone glycoside, chrysin-6-C-fucopyranoside, showed potent and selective activity toward PPARγ, with no effects on other PPAR subtypes or TRP channels. These findings indicate that the caigua plant could offer a safer alternative to conventional PPARγ agonists, whose use as antidiabetic drugs is limited by severe side effects that currently restrict the clinical use of conventional PPAR agonists. Full article

Tea polyphenols, the primary bioactive constituents responsible for the various health benefits of tea, can be categorized into different subgroups according to their structural characteristics. However, the distinctions in antiviral activity among the diverse types of polyphenolic compounds remain unexplored. In the present study, fifty-eight tea polyphenols with varied structures, including eleven undescribed compounds, were isolated from Rougui Wuyi rock tea. Their molecular structures were elucidated using comprehensive analytical approaches of NMR, HRMS, CD spectroscopic data and acid hydrolysis. The isolated polyphenol analogs could be structurally classified into two main categories: flavan-3-ols, which include catechins, flavoalkaloids, procyanidins and theasinensins, and flavones, encompassing kaempferol, quercetin, myricetin, and their respective glycosides. The inhibitory activities of fifty-eight tea polyphenols against 3CLpro were assessed in vitro, and eighteen phenolic compounds exhibited inhibitory effects on 3CLpro, with IC₅₀ values ranging from 9.8 μM to 61.1 μM. Among them, two types of tea polyphenols, catechin and flavoalkaloid derivatives, demonstrated superior inhibitory effects compared to other categories. The structure-activity relationship was further explored, and molecular docking analysis revealed that the differing inhibitory effects of catechin and flavoalkaloid derivatives were attributed to the variations in the number and positions of the hydrogen bond interactions with 3CLpro. This study provides a valuable understanding of tea polyphenols and supplies potential lead compounds for antiviral drugs. Full article

The genus Ruspolia refers to a small group of plants in the Acanthaceae family, with two dominant species R. decurrens and R. hypocrateriformis essentially distributed in tropical parts of Africa. Decoctions from these plants are used in folk medicine for the treatment of a few human pathologies but the active ingredients at the origin of the bioactivities have been little studied. Here, we give an insight into the main phytochemicals of the Ruspolia species published in the literature so far and their pharmacological properties. The flavone glycosides justicialosides A-B likely serve as antioxidant agents and free radical scavengers. Several pyrrolidine alkaloids have been isolated from these Ruspolia species, notably (nor)ruspolinone and a few related products. These molecules have attracted the interest of medicinal chemists, with different synthetic routes leading to ruspolinone and analogues. There are versatile operating procedures to synthesize (nor)ruspolinone isomers. Despite these chemical efforts, the pharmacology of ruspolinone remains largely unknown. A few other Ruspolia alkaloids have been isolated, notably the rare bispyrrolidine benzodioxin alkaloid hypercratine, possibly acting as a ligand of β2-adrenergic receptors. A phytochemical survey of the Ruspolia species sheds light on the diversity of products in this family to promote further investigations into the mechanism of action of ruspolinone and related natural products. Full article

Several members of Stachys L. (among the largest Lamiaceae genera) have been traditionally used as medicinal plants. With 54 Stachys taxa (species and subspecies) occurring in mainland and/or insular Greece, the present study aimed to investigate the metabolic profiling of four range-restricted local Stachys members: Stachys candida and S. chrysantha (protected and endangered local Greek endemics), S. leucoglossa subsp. leucoglossa (local Balkan endemic), and S. spinulosa (local Balkan subendemic). In this investigation, the infusions of their above-ground parts were characterized using NMR and HPLC-PDA-MS techniques. Thus, 1D- and 2D-NMR spectra were obtained to compare the chemical fingerprints of these plants. Furthermore, previously isolated compounds from Stachys spp. were used to identify specific constituents. NMR screening revealed the presence of: (i) phenylethanoid glycosides, mainly acteoside in S. candida and S. chrysantha (section Candida, Swainsoniana phyloclade), and (ii) flavone 7-O-allosylglucoside (isoscutellarein 7-O-[6‴-O-acetyl-β-D-allopyranosyl]-(1→2)-β-D-glucopyranoside) and iridoids (monomelittoside or/and melittoside) in S. leucoglossa subsp. leucoglossa (section Olisia, Swainsoniana/Olisia phyloclade, Swainsoniana phyloclade) and caffeoylquinic acid (chlorogenic acid) in S. spinulosa (section Campanistrum, Stachys phyloclade). In total, 26 compounds were detected by HPLC-PDA-MS belonging to flavonoids, phenylethanoid glycosides, and phenolic acids. Among them, chlorogenic acid was identified in all samples as one of their main metabolites. The present study complements previous studies with first reports of constituents detected in the studied taxa, reports for the first time on the metabolic characterization of S. spinulosa, and discusses the chemotaxonomic significance of such findings. Full article

Crocus sativus L. is largely cultivated because it is the source of saffron, a well-appreciated and valued spice, not only for its culinary use but also because of its significant biological activities. Stigmas are the main product obtained from flowers, but in addition, tepals, largely considered a waste product, represent a big source of flavonoids and anthocyanins. This study aimed to delve into the phytochemical composition of saffron tepals and investigate whether the composition was influenced by the extraction technique while investigating the main analytical techniques most suitable for the characterization of tepal extracts. The research focuses on flavonoids, a class of secondary metabolites, and their health benefits, including antioxidant, anti-inflammatory, and anticancer properties. Flavonoids occur as aglycones and glycosides and are classified into various classes, such as flavones, flavonols, and flavanones. The most abundant flavonoids in tepals are kaempferol glycosides, followed by quercetin and isorhamnetin glycosides. Overall, this review provides valuable insights into the potential uses of tepals as a source of bioactive compounds and their applications in various fields, promoting a circular and sustainable economy in saffron cultivation and processing. Full article

Stroke is a serious condition that results from an occlusion of blood vessels that leads to brain damage. Globally, it is the second highest cause of death, and deaths from strokes are higher in older people than in the young. There is a higher rate of cases in urban areas compared to rural due to lifestyle, food, and pollution. There is no effective single medicine for the treatment of stroke due to the multiple causes of strokes. Thrombolytic agents, such as alteplase, are the main treatment for thrombolysis, while multiple types of surgeries, such ascraniotomy, thrombectomy, carotid endarterectomy, and hydrocephalus, can be performed for various forms of stroke. In this review, we discuss some promising phytocompounds, such as flavone C-glycoside (apigenin-8-C-β-D-glucopyranoside), eriodictyol, rosamirinic acid, 6″-O-succinylapigenin, and allicin, that show effectiveness against stroke. Future study paths are given, as well as suggestions for expanding the use of medicinal plants and their formulations for stroke prevention. Full article

Plants are the main sources of bioactive compounds (nutraceuticals) that function under different mechanisms of action for the benefit of human health. Mexico ranks fifth in the world in biodiversity, offering opportunities for healthy food. An important variety of crops are produced in the state of Hidalgo, e.g., based on the 2021 production, alfalfa, oats, maguey, and corn. The present review presents the latest findings of these crops, regarding the benefits they provide to health (bioactivity, nutraceuticals), and presents the compounds and mechanisms identified by which the benefit is provided. The knowledge compiled here is for the benefit of the recovery of the crops, the recognition of their bioactivities, in search of identifying the best routes of action for prevention, treatment and possible cure of chronic degenerative diseases (thereby promoting crop valorization). Exhaustive bibliographic research was carried out by means of engines and scientific databases. Articles published between 2001 and 2022 that included specific keywords (Scopus, EMBASE, EBSCO, PubMed, Science Direct, Web of Science, Google Scholar). Outstanding activities have been identified for the compounds in the crops, such as antiinflammatory, anticholesterolemic, antihypertensive, antidiabetic, anticancer, antimicrobial, antioxidant, and chelating. The compounds that provide these properties are total phenols, phenolic acids, tannins, anthocyanins, carotenoids, iso-flavones, phytosterols, saponins, fructans, glycosides, glucans, avenanthramides, and polysaccharides. Full article

To extend the application of celery (Apium graveolens L.) seeds, the antioxidant and enzymatic inhibitory activities of different fractions and their main flavones were investigated. The n-butanol fractions possessed the highest total phenolic content (TPC) and total flavonoid content (TFC) values. The n-butanol fractions from Northeast China samples exhibited the strongest free radical scavenging (DPPH IC₅₀ = 20.27 μg/mL, ABTS IC₅₀ = 15.11 μg/mL) and ferric reducing antioxidant power (FRAP 547.93 mg trolox (TE)/g) capacity, while those collected from Hubei China showed the optimal cupric reducing antioxidant capacity (CUPRAC) values (465.78 mg TE/g). In addition, the dichloromethane fractions from Jiangsu samples displayed a maximum Fe²⁺ chelating capacity (20.81 mg ethylene diamine tetraacetic acid (EDTA)/g). Enzyme level experiments indicated polyphenolic compounds might be the main hypoglycemic active components. Subsequently, the enzyme inhibitory activity of nine main flavones was evaluated. Chrysoeriol-7-O-glucoside showed better α-glucosidase inhibitory activity than others. However, apigenin showed the best inhibitory effect on α-amylases, while the presence of glycosides would reduce its inhibitory effect. This study is the first scientific report on the enzymatic inhibitory activity, molecular docking, and antioxidant capacity of celery seed constituents, providing a basis for treating or preventing oxidative stress-related diseases and hyperglycemia. Full article

Tulipa gesneriana has rich cultivars with abundant flower colors; among them, black tulips have become precious cultivars for their rareness in nature. It is of great significance to understand its color formation mechanism for breeding new cultivars with a blackish flower color in the future. In this present study, petals at five developmental stages of Tulipa gesneriana ‘Queen of Night’ (shorted for ‘QN’), a typical black tulip cultivar, were collected to identity the flavonoid composition and compare the accumulation along with the flower development process, aiming to explore the metabolic mechanism of its flower coloration. By using UPLC-Q-TOF-MS, three anthocyanins and nineteen anthoxanthins (including eighteen flavonols and one flavone) were detected in the petals of ‘QN’. The anthocyanins were identified as delphinidin 3-o-rutinoside, cyanidin 3-o-rutinoside and pelargonidin 3-o-rutinoside, respectively. The main flavonols were identified as quercetin, kaempferol, isorhamnetin, naringin and their glycosides. The only one flavone substance was identified as an apigenin derivative. By comparing the content, anthocyanins were the most abundant substance in the petals of ‘QN’, and showed obvious regularity in the development process. With the flower opening, the anthocyanin content accumulated continuously, and reached the highest level at 3575.9 μg·g⁻¹·FW at S5, accounting for 80% of the total flavonoids. Among them, delphinidin 3-o-rutinoside and cyanidin 3-o-rutinoside made the main contribution to the coloration of ‘QN’. The content of anthoxanthins increased first and then decreased, reaching the highest to 1114.8 μg·g⁻¹·FW at S3. Quercetin and its glycosides were the most important flavonol substances in the petals of ‘QN’, accounting for more than 60% of the total anthoxanthins in the five stages. The content of a flavone identified was extremely low, suggesting a limited role in the flower color of ‘QN’. Taken together, the flower color presentation of ‘QN’ was closely related to the composition and accumulation of anthocyanins and flavonols; anthocyanins were the main substances that determine the petal coloration of ‘QN’, and the high content of flavonols played a role of co-pigmentation with these anthocyanins. Full article

The increasing attention on the impact of food on human and environmental health has led to a greater awareness about nutrition, food processing, and food waste. In this perspective, the present work deals with the investigation of the chemical non-volatile and volatile profiles of two Citrus-based products, produced through a conscious process, using Citrus peels as natural gelling agents. Moreover, the total polyphenol content (TPC) and the antioxidant properties were evaluated, as well as their sensorial properties. Chemical and antioxidant results were compared with those of Citrus fresh fruits (C. reticulata, C. sinensis, and C. limon). Concerning the non-volatile fingerprint, the two samples showed a very similar composition, characterized by flavanones (naringenin, hesperetin, and eriodyctiol O-glycosides), flavones (diosmetin and apigenin C-glucosides), and limonoids (limonin, nomilinic acid, and its glucoside). The amount of both flavonoids and limonoids was higher in the Lemon product than in the Mixed Citrus one, as well as the TPC and the antioxidant activity. The aroma composition of the two samples was characterized by monoterpene hydrocarbons as the main chemical class, mainly represented by limonene. The sensorial analysis, finally, evidenced a good quality of both the products. These results showed that the most representative components of Citrus fruits persist even after the transformation process, and the aroma and sensorial properties endow an added value to Citrus preparations. Full article

Several medical plants belonging to the genera Passiflora, Viola, and Crataegus accumulate flavonoid C-glycosides, which likely contribute to their efficacy. Information regarding their phase I and II metabolism in the liver are lacking. Thus, in vitro liver metabolism of orientin, isoorientin, schaftoside, isoschaftoside, vitexin, and isovitexin, all of which accumulated in Passiflora incarnata L., was investigated by incubation in subcellular systems with human liver microsomes and human liver S9 fraction. All metabolite profiles were comprehensively characterized using HPLC-DAD and UHPLC–MS/MS analysis. Mono-glycosylic flavones of the luteolin-type orientin and isoorientin showed a broad range of mono-glucuronidated and mono-sulfated metabolites, whereas for mono-glycosylic flavones of the apigenin-type vitexin and isovitexin, only mono-glucuronidates could be detected. For di-glycosylic flavones of the apigenin-type schaftosid and isoschaftosid, no phase I or II metabolites were identified. The main metabolite of isoorientin was isolated using solid-phase extraction and prep. HPLC-DAD and identified as isoorientin-3′-O-α-glucuronide by NMR analysis. A second isolated glucuronide was assigned as isoorientin 4′-O-α-glucuronide. These findings indicate that vitexin and isovitexin are metabolized preferentially by uridine 5′-diphospho glucuronosyltransferases (UGTs) in the liver. As only orientin and isoorientin showed mono-sulfated and mono-glucuronidated metabolites, the dihydroxy group in 3′,4′-position may be essential for additional sulfation by sulfotransferases (SULTs) in the liver. The diglycosylic flavones schaftoside and isoschaftoside are likely not accepted as substrates of the used liver enzymes under the chosen conditions. Full article

This work presents a green, downstream process, from extraction to phytochemical characterization and bioactivity testing, to obtain and evaluate the functional properties of phenolic compounds from cowpea (Vigna unguiculata (L.) Walp.) seeds and pods. Phenolic-rich extracts were obtained by pressurized liquid extraction (PLE). The main factors affecting the extraction conditions (temperature and solvent) were optimized in order to attain extracts with the highest extraction yield, antioxidant capacity, and total phenolic content. The optimal extraction conditions were 1:1 ethanol:water at 170 °C with one extraction cycle for seeds and three extraction cycles for pods. Phenolic compounds of optimal extract were analyzed by UHPLC-q-TOF-MS/MS (quadrupole-time of flight tandem MS). The obtained PLE-extracts exhibited higher phenolic content and antioxidant activity compared to conventional extraction procedures. The in vitro anti-neurodegenerative potential of extracts was measured through Acetylcholinesterase (AChE) inhibition assay. The results revealed the higher bioactivity observed in cowpea pod samples compared to seed extracts, which might be related to higher levels of quercetin and quercetin glycosides, kaempferol diglucoside, and other tetrahydroxylated flavones and flavonols identified in these samples. These results also provide an added-value benefit to the cultivation of this legume, considering the high potential of cowpea phenolic extracts as nutraceutical and functional ingredients in food formulations. Full article

Rutin is a flavone glycoside contained in many plants, and exhibits antioxidant, anti-inflammatory, anticancer, and wound-healing properties. The main disadvantage related to the use of this molecule for pharmaceutical application is its poor bioavailability, due to its low solubility in aqueous media. Poloxamer 407-hydrogels show interesting thermo-sensitive properties that make them attractive candidates as pharmaceutical formulations. The hydrophobic domains in the chemical structure of the copolymer, a polymer made up of two or more monomer species, are useful for retaining poorly water-soluble compounds. In this investigation various poloxamer 407-based hydrogels containing rutin were developed and characterized as a function of the drug concentration. In detail, the Turbiscan stability index, the micro- and dynamic rheological profiles and in vitro drug release were investigated and discussed. Rutin (either as a free powder or solubilized in ethanol) did not modify the stability or the rheological properties of these poloxamer 407-based hydrogels. The drug leakage was constant and prolonged for up to 72 h. The formulations described are expected to represent suitable systems for the in situ application of the bioactive as a consequence of their peculiar versatility. Full article

Citrus spp. are among the most widespread plants cultivated worldwide and every year millions of tons of fruit, juices, or processed compounds are produced and consumed, representing one of the main sources of nutrients in human diet. Among these, the flavonoids play a key role in providing a wide range of health beneficial effects. Apigenin, diosmetin, luteolin, acacetin, chrysoeriol, and their respective glycosides, that occur in concentrations up to 60 mg/L, are the most common flavones found in Citrus fruits and juices. The unique characteristics of their basic skeleton and the nature and position of the substituents have attracted and stimulated vigorous investigations as a consequence of an enormous biological potential, that manifests itself as (among other properties) antioxidant, anti-inflammatory, antiviral, antimicrobial, and anticancer activities. This review analyzes the biochemical, pharmacological, and biological properties of Citrus flavones, emphasizing their occurrence in Citrus spp. fruits and juices, on their bioavailability, and their ability to modulate signal cascades and key metabolic enzymes both in vitro and in vivo. Electronic databases including PubMed, Scopus, Web of Science, and SciFinder were used to investigate recent published articles on Citrus spp. in terms of components and bioactivity potentials. Full article

Anoectochilus roxburghii is a traditional Chinese herb with high medicinal value, with main bioactive constituents which are flavonoids. It commonly associates with mycorrhizal fungi for its growth and development. Moreover, mycorrhizal fungi can induce changes in the internal metabolism of host plants. However, its role in the flavonoid accumulation in A. roxburghii at different growth stages is not well studied. In this study, combined metabolome and transcriptome analyses were performed to investigate the metabolic and transcriptional profiling in mycorrhizal A. roxburghii (M) and non-mycorrhizal A. roxburghii (NM) growth for six months. An association analysis revealed that flavonoid biosynthetic pathway presented significant differences between the M and NM. Additionally, the structural genes related to flavonoid synthesis and different flavonoid metabolites in both groups over a period of six months were validated using quantitative real-time polymerase chain reaction (qRT-PCR) and high-performance liquid chromatography coupled with tandem mass spectrometry (HPLC-MS/MS). The results showed that Ceratobasidium sp. AR2 could increase the accumulation of five flavonol-glycosides (i.e., narcissin, rutin, isorhamnetin-3-O-beta-d-glucoside, quercetin-7-O-glucoside, and kaempferol-3-O-glucoside), two flavonols (i.e., quercetin and isorhamnetin), and two flavones (i.e., nobiletin and tangeretin) to some degrees. The qRT-PCR showed that the flavonoid biosynthetic genes (PAL, 4CL, CHS, GT, and RT) were significantly differentially expressed between the M and NM. Overall, our findings indicate that AR2 induces flavonoid metabolism in A. roxburghii during different growth stages, especially in the third month. This shows great potential of Ceratobasidium sp. AR2 for the quality improvement of A. roxburghii. Full article