Search Results (556)

Background: Wampee (Clausena lansium (Lour.) Skeels) is an understudied Rutaceae crop native to southern China, whose fruit features a complex aroma profile with simultaneous sour, sweet, bitter and astringent notes. Although bioactive compounds including flavonoids, alkaloids and volatile oils in wampee fruit have been partially characterized, the tissue-specific metabolic and transcriptional basis underlying its distinctive aroma formation remains largely unclear. Methods: We performed an integrated volatile metabolomic and transcriptomic analysis on the pericarp (peel) and flesh of wampee fruit across three cultivars (Shanyellowpi, Heijingang, Bingtangxin). Volatile metabolites were profiled via headspace solid-phase microextraction coupled with gas chromatography-mass spectrometry (HS-SPME-GC-MS), and transcriptome profiles were generated by RNA-Seq. Multi-omics integration was conducted using Procrustes analysis, gene–metabolite correlation network construction and weighted gene co-expression network analysis (WGCNA). Results: A total of 288 volatile metabolites were identified, representing the most comprehensive volatile inventory for C. lansium reported to date. Principal component analysis and partial least squares discriminant analysis revealed distinct volatile profiles between pericarp and flesh; terpenoids were the dominant chemical class, accounting for 71.56–91.48% of total volatiles in pericarp and 61.88–67.22% in flesh. Notably, organoheterocyclic compounds were significantly enriched in Shanyellowpi flesh (40.45%), forming a cultivar-specific metabolic signature absent in the other two cultivars. Transcriptomic analysis showed that phenylpropanoid biosynthesis was the most significantly enriched pathway among differentially expressed genes, followed by monoterpene biosynthesis and sesquiterpenoid biosynthesis. Procrustes analysis demonstrated a strong global concordance between the two omics layers (M² = 0.535, p < 0.001). Gene–metabolite correlation networks identified terpene synthase (TPS) genes (HP075360, HP217350) and oxidoreductase genes (SOD1, GST, 10HGO) as candidate co-regulators of terpenoid biosynthesis. WGCNA further prioritized TPS genes, cytochrome P450 genes and MYB transcription factor genes as key regulators driving volatile metabolic divergence between tissues. Conclusion: This study provides a comprehensive volatile and transcriptomic atlas of wampee fruit, and identifies tissue-specific and cultivar-specific metabolic signatures as well as their candidate regulatory genes. These findings advance our understanding of quality differentiation in Rutaceae fruits and lay a foundation for molecular breeding and flavor improvement of wampee. Full article

Although Atractylodes macrocephala Koidz. (AM) exhibits various pharmacological properties, its molecular effects and active constituents regarding anagen entry and physiological hair cycle progression remain uncharacterized. This study aimed to investigate the hair growth-promoting efficacy of AM and identify its bioactive compounds and underlying molecular mechanisms. We evaluated AM extract using human dermal papilla cells (DPCs) and a synchronized depilation-induced C57BL/6 mouse model, employing RT-PCR, Western blotting, immunofluorescence, and SwissADME-based pharmacokinetic profiling. AM significantly enhanced DPC proliferation and migration while upregulating paracrine factors (HGF, VEGF, and FGF7). Mechanistically, AM activated Akt, ERK, and p38 MAPKs, leading to GSK3β phosphorylation (Ser9) and subsequent β-catenin stabilization. In vivo, oral AM (60 mg/kg) markedly accelerated the telogen-to-anagen transition, increasing dermal thickness, follicle count, and hair shaft quality without systemic toxicity. Furthermore, cell-based screening and SwissADME prioritized atractylenolide I and III as the chief bioactive sesquiterpenoids driving DPC activation. In conclusion, AM and its key atractylenolides promote anagen entry and hair regrowth, in association with GSK3β phosphorylation and β-catenin stabilization, representing promising natural candidates for promoting physiological hair cycle progression. Full article

Curcuma longa is a medicinal plant valued for its diverse phytochemicals and antioxidant properties. However, the effects of thermal processing on its phytochemical composition and antioxidant function remain insufficiently understood. This study investigated heat-induced changes in curcuminoids, sesquiterpenoids, and their degradation products in C. longa extracts heated at 180 °C for 0–90 min under dry, aqueous, olive oil, and corn oil conditions using UHPLC–MS/MS and GC–MS. Curcuminoids progressively decreased during heating, whereas sesquiterpenoids exhibited greater thermal stability, particularly in oil matrices. Antioxidant properties were also better preserved in oil-treated extracts than in those heated under dry or aqueous conditions. However, in an oil-in-water emulsion system exposed to continuous LED illumination (14,600 lux), extracts obtained after dry heating accelerated lipid oxidation, as evidenced by enhanced oxygen depletion, hydroperoxide formation, and conjugated diene accumulation. This pro-oxidative effect was markedly suppressed by EDTA, suggesting the involvement of metal-mediated oxidation pathways. These findings demonstrate that thermal processing differentially alters the phytochemical profile and antioxidant properties of C. longa depending on the heating matrix, while highlighting that preserved antioxidant capacity does not necessarily translate into improved oxidative stability in illuminated emulsion systems. Full article

This study is the first report on the chemical composition and antimicrobial activity of Chaerophyllum bulbosum L. sampled from the Armenian flora. Essential oil (EO) and hydrosol were obtained from the aerial parts by hydrodistillation, and their chemical compositions were determined by GC–MS, identifying a total of 48 volatiles. The EO was composed of 60.42% monoterpenes and their oxygenated derivatives and 18.75% sesquiterpenes and their oxygenated derivatives, while the hydrosol was composed of 75% oxygenated monoterpenes, with the remaining 20% and 5% being monoterpenes and sesquiterpenoids respectively. Pulegone (21.55%) was identified as the major constituent. With regard to the non-volatile fraction, the methanolic extract displayed a total phenolic content of 1.17 ± 0.03 mg GAE/g dry weight and a total flavonoid content of 0.62 ± 0.02 mg QE/g, as well as significant antioxidant capacity, with IC₅₀ values of 2.87 ± 0.06 μg Trolox/g dried plant sample for the DPPH^• assay and 46.87 ± 1.2 μmol Fe²⁺/g dried plant sample for the FRAP assay. The evaluation of EO and hydrosol antimicrobial properties revealed notable antibacterial activity against Gram-positive bacteria, with inhibition zones ranging from 13.5 to 20 mm. The respective minimum inhibitory concentration (MIC) values ranged from 0.4 to 6.0 mg/mL for the EO and from 62.5 to 400 μL/mL for hydrosol, while the minimum bactericidal concentration (MBC) values ranged from 0.8 to 10.0 mg/mL and from 125 to 800 μL/mL, respectively. Streptococcus mutans was the most susceptible microorganism (MIC = 0.4 mg/mL), whereas Pseudomonas aeruginosa was the most resistant (MIC = 6.0 mg/mL). Both the EO and hydrosol exhibited antifungal activity against Candida albicans, with inhibition zones of 13.0 ± 1.2 mm and 11.0 ± 0.8 mm, respectively. The MIC and MBC values were 1.0 and 2.0 mg/mL for the EO, while the respective values for the hydrosol were 400 and 800 μL/mL. These findings highlight the C. bulbosum plant as a promising source of bioactive compounds with significant activity against Gram-positive bacteria and moderate antifungal effects that may be associated with the high content of pulegone, a monoterpene known for its membrane-disruptive properties. Full article

Alzheimer’s disease (AD) is characterized by the excessive production and aggregation of β-amyloid (Aβ), which serves as key pathological features of disease progression. Although Humulus japonicus Siebold & Zucc. is a traditional medicinal plant rich in flavonoids and phenolic compounds, its specific anti-amyloidogenic constituents remain to be fully elucidated. This study evaluated the effects of the aerial parts of H. japonicus on Aβ production and aggregation, and identified its active constituents through bioassay-guided isolation. The 80% ethanolic extract of H. japonicus aerial parts significantly reduced soluble amyloid precursor protein β (sAPPβ) levels and BACE1 protein expression in Chinese Hamster Ovary cells stably expressing amyloid precursor protein (APP-CHO cells). Furthermore, it inhibited Aβ aggregation and promoted fibril disaggregation in Thioflavin T assays. Among the solvent-partitioned fractions, the ethyl acetate fraction exhibited the most potent anti-amyloidogenic activity and was subjected to chromatographic isolation, leading to the characterization of fourteen compounds (7 flavonoids, 2 phenolic acids, 2 sesquiterpenoids, and 3 phenylpropanoids). Specifically, luteolin 7-O-β-d-glucopyranoside (2), orientin (3), vitexin (5), vomifoliol (8), abscisic acid (9), and p-hydroxyphenylethyl-p-coumarate (12) significantly decreased sAPPβ levels, as well as BACE1 and Presenilin-1 protein expression. Meanwhile, luteolin 7-O-β-d-glucopyranoside (2), orientin (3), vitexin (5), and quercetin 7-O-β-d-glucopyranoside trimer (7) effectively reduced Aβ aggregation and enhanced the disaggregation of pre-formed Aβ aggregates. Collectively, luteolin 7-O-β-d-glucopyranoside (2), orientin (3), and vitexin (5) exhibited the most consistent dual inhibitory effects on both Aβ production and aggregation, supporting their selection as key marker compounds. Among the extracts prepared with varying ethanol concentrations, the 100% ethanol extract yielded the highest levels of these flavonoid glycosides and exhibited the strongest anti-amyloidogenic activity. These findings suggest that the aerial parts of H. japonicus and its constituent flavonoid glycosides represent promising natural resources for modulating amyloidogenic APP processing and Aβ aggregation in AD. Full article

Background: Polygodial (9), a drimane sesquiterpene dialdehyde from Drimys winteri, has not previously been examined against carbohydrate-hydrolyzing enzymes. Methods: Regioselective Wittig olefination at C12 gave the enoate 10; reduction of the remaining C11 aldehyde with NaBH₄ was followed by spontaneous intramolecular conjugate addition, affording the annellated tetrahydrofuran 12a and the bridged ether 12b. Results: All three derivatives inhibited α-glucosidase and α-amylase more strongly than the parent compound. Compound 12a was the most active α-glucosidase inhibitor (IC₅₀ = 53.98 ± 3.0 µM, against 90.36 ± 4.0 µM for acarbose) and, in docking, the only derivative to occupy the acarbose-binding site of the enzyme (−8.1 kcal/mol). However, this 12a–α-glucosidase pose was not maintained during the 200 ns simulations. The enoate 10 was the most active α-amylase inhibitor (IC₅₀ = 42.32 ± 2.1 µM, against 78.24 ± 3.9 µM for acarbose; −8.5 kcal/mol). Over 200 ns of molecular dynamics, the 10–α-amylase complex remained associated, with binding attributed by MM-GBSA mainly to van der Waals and lipophilic terms. Conclusions: Converting the dialdehyde into an enoate or a cyclic ether increases carbohydrase inhibition and determines which of the two enzymes is preferentially inhibited. Full article

Acute myocardial ischemia (AMI) is a life-threatening cardiovascular disorder characterized by excessive oxidative stress and persistent inflammatory cascades, yet safe multi-target natural therapeutic agents remain scarce. Cinnamomum migao is a well-known Miao ethnic medicine used for cardiovascular conditions, yet its cardioprotective effects and mechanisms remain largely unclear. This study investigated the efficacy and underlying mechanism of C. migao ethyl acetate extract (MGE) against AMI. MGE significantly improved the viability of H9c2 cardiomyocytes subjected to OGD/R injured. UPLC-MS/MS and molecular networking identified 30 constituents in MGE, among which sesquiterpenoids predominated. In ISO-induced AMI rats, MGE dose-dependently mitigated myocardial injury, as reflected by reduced ST-segment elevation, serum CK-MB and LDH levels, and alleviated histopathological damage. MGE enhanced SOD and CAT activities, decreased MDA content, and inhibited the secretion of TNF-α, IL-6 and IL-1β. Mechanistically, MGE downregulated the expression of NOX4, HIF-1α, p38 MAPK and NF-κB p65, while activating the Nrf2/HO-1 pathway. Oxyphyllenone A and magnodelavin C were identified as key active sesquiterpenoids that stably bound to IL-17 and TNF. Collectively, MGE alleviates AMI injury via anti-oxidative, anti-hypoxic, and anti-inflammatory effects through modulation of the HIF-1α/Nrf2/NF-κB/MAPK axis downstream of oxidative stress, with sesquiterpenoids serving as its key bioactive components. This work provides robust experimental evidence supporting C. migao as a promising natural antioxidant candidate for the prevention and treatment of AMI. Full article

Dittrichia viscosa (L.) Greuter is a Mediterranean species widely recognized for its remarkable ecological plasticity and its rich repertoire of secondary metabolites, among which volatile organic compounds (VOCs) play a central role. This review provides an integrative synthesis of current knowledge on D. viscosa, with a primary focus on its VOCs, including their extraction techniques, chemotypic variability, and biological activities, while contextualizing these compounds within the species’ broader phytochemical and ecological framework. Available evidence indicates that VOC profiles are dominated by terpenoids, particularly oxygenated sesquiterpenes and monoterpenes. The composition of volatile fractions is strongly influenced by extraction methodology, plant organ, developmental stage, and geographic origin, resulting in pronounced chemotypic variability across Mediterranean populations. Beyond their direct bioactivity, VOCs are considered in their ecological context, particularly in relation to glandular trichome-mediated secretion, plant–insect interactions, and potential applications in integrated pest management. Non-volatile metabolites are also discussed to provide a comprehensive view of the species’ bioactive potential. Overall, D. viscosa emerges as a multifunctional species in which VOCs are a pivotal, though not isolated, component of a complex phytochemical system with promising applications in agriculture, pharmacology, and environmental management. While the convergence of multiple studies supports the biological potential of D. viscosa and its metabolites, particularly in vitro, the translation of these findings into in vivo efficacy and safety remains an important area for future research. This integrative perspective highlights the need for standardized analytical approaches and chemotype-aware studies to fully exploit the biological and biotechnological potential of this Mediterranean species. Full article

Among the three lineages of bryophytes, liverworts exhibit a wide variety of terpenoid fingerprints. Terpenoids are abundant in the oil bodies of liverworts. Hornworts and mosses are also reported to contain sesqui-, di-, and triterpenoids, although they lack oil bodies. Overall, the abundance of sesquiterpenoids is much greater than that of other types of terpenoid compounds. The occurrence of triterpenoids is very low. Terpenoids found in higher plants are detected in Marchantiophyta in their enantiomeric forms, with a few exceptions. Organic chemists discovered many di- and sesquiterpenoids with interesting carbon skeletons. Bryophytes possess microbial terpene synthase-like enzymes that are different from typical plant terpene synthases. Original research articles and high-quality reviews were extracted from Google Scholar, PubMed, ScienceDirect, and Scopus using the keywords “terpenoid diversity”, “terpenoid and chemosystematics”, “terpenoids of bryophytes”, “oil bodies”, “terpene synthase”, “microbial terpene synthase-like enzymes”, and “genomics and terpenoid research progress” to prepare this review. Only the literature published in the English language was considered. This review focused on the terpenoid diversity of bryophytes, including chemosystematics uses, as well as the varying carbon skeletons of terpenoids. Oil body biogenesis and evolution, along with the terpene biosynthesis pathway and related enzymes, are briefly covered. The emergent area of multi-omics approaches may bridge the gap that exists in this field and will also open up future avenues for the use of Marchantia polymorpha or Physcomitrella patens as an efficient tool for specific and valuable terpenoid production. Full article

Atractylodes chinensis (DC.) Koidz is a pharmacologically significant medicinal plant that produces various bioactive metabolites, including β-eudesmol, which largely determines its medicinal quality and clinical efficacy. Treatment of A. chinensis hairy roots with 5-methoxyindole (5-MI), a chemical homolog of melatonin, revealed that 0.5 mmol·L⁻¹ 5-MI significantly enhanced β-eudesmol production. To investigate the underlying mechanism, we performed integrated transcriptomic and metabolomic analyses. Comprehensive targeted metabolomics identified ten upregulated terpenoids among the differentially expressed metabolites following 5-MI treatment in A. chinensis hairy roots, including β-eudesmol. The 5-MI treatment significantly influenced the expression levels of genes associated with metabolic regulation and secondary metabolite synthesis in A. chinensis hairy roots, particularly promoting the upregulation of genes involved in terpenoid biosynthesis. Notably, a putative sesquiterpene synthase gene, AcTPS1, was significantly upregulated after 5-MI treatment and was a strong candidate gene correlated with β-eudesmol. AcTPS1 belongs to the TPS-a subfamily and exhibits tissue-specific expression, with high transcript levels in root tissues, especially in one-year-old roots of A. chinensis. This study demonstrates that 5-MI serves as an effective elicitor, providing valuable insights for the production of medicinally active compounds and enhancing our understanding of the molecular mechanism by which 5-MI regulates plant secondary metabolism. Full article

Plant volatile organic compounds (VOCs) are crucial for communication, defense, pollination, and environmental adaptation, playing a key role in the survival and interaction of plants within ecosystems. However, as an important tree species rich in VOCs, the variation characteristics and influencing factors of VOCs on Phoebe hui W.C. Cheng ex Yen C. Yang remain unclear. In this study, we identified 106 VOCs across branches and leaves, of which 91 and 56 were detected, respectively, with 41 in both tissues. Sesquiterpenoids, olefins, fatty acids and conjugates dominated the VOC profiles of branches and leaves. Branches showed higher accumulation of sesquiterpenoids, fatty acids and conjugates, whereas leaves were enriched in olefins. The VOCs distribution and accumulation were strongly structured by environmental variation, with mean annual precipitation (MAP) and soil organic carbon (SOC) emerging as the primary drivers. Together, these findings elucidate the variation patterns and environmental determinants of VOCs in P. hui, providing a foundation for resource conservation and utilization while informing studies of VOC diversity across Phoebe species. Full article

Background/Objectives: Bursera bipinnata (DC.) Engl. resin (locally known as “copal blanco”) is traditionally used in Mexican ethnomedicine to treat infected wounds and skin inflammation, but the bioactive constituents underlying these effects remain largely uncharacterized. This study aimed to identify the compounds responsible for the wound-healing properties of the resin through bioactivity-guided fractionation and to evaluate their anti-inflammatory and antibacterial activities as complementary mechanisms supporting tissue repair. Methods: Crude resin (1.2–5.0 mg/mL) was assayed for anti-inflammatory activity in the TPA-induced ear-edema model in BALB/c mice, for antibacterial activity (MIC) against six clinically relevant strains, and for wound-healing activity in a murine excisional model with pirfenidone (PFD) as the reference drug (n = 5 per group). Bioactivity-guided fractionation followed by spectroscopic elucidation (¹H- and ¹³C-NMR, IR, EI-MS) led to the isolation of five constituents. Stigmasterol, the most active compound, was subsequently evaluated in an LPS-induced systemic inflammation model (oral administration, 20 mg/kg/day × 3 days) to characterize its immunomodulatory profile (TNF-α, IL-1β, IL-6, IFN-γ, IL-10) and in the wound-healing model to quantify local IL-6, IL-10 and TGF-β1 in skin homogenates. Results: The crude resin (5.0 mg/mL) achieved 99.63% wound closure at day 12 and a 49.08% reduction in TPA-induced ear edema, comparable to indomethacin (55.76%). The resin displayed selective antibacterial activity against Streptococcus pyogenes (MIC 125 µg/mL) and Salmonella typhimurium (MIC 250 µg/mL). Bioactivity-guided fractionation yielded the phytosterol stigmasterol (1), three lupane-type triterpenoids (lupeol acetate (2), lupenone (3), 3-epilupeol (5)), and the sesquiterpenoid caryophyllene oxide (4). At an equimolar 1 µM concentration, stigmasterol (1) shortened the mean wound-healing time to 10.3 ± 0.4 days, comparable to pirfenidone, and was associated with attenuation of systemic TNF-α, IL-1β and IL-6 peaks and with sustained local IL-10 and TGF-β1 expression. Histological assessment confirmed accelerated re-epithelialization and improved collagen organization. The resin was non-irritant in the OECD 404 acute dermal test (Primary Irritation Index = 0.00). Conclusions: These findings provide pharmacological evidence supporting the traditional use of B. bipinnata resin for wound healing. Stigmasterol (1), together with the lupane-type triterpenoids lupenone (3) and 3-epilupeol (5), were identified as key bioactive constituents. The data are consistent with a coordinated immunomodulation, in which stigmasterol is associated with reduced systemic pro-inflammatory signalling and increased local IL-10/TGF-β1 expression, an interpretation that should be confirmed in chronic and impaired wound-healing models. Full article

This study aimed to analyze the phytochemical composition of hexane extracts from Bixa orellana L. leaves using multivariate analysis and to evaluate their antimicrobial and antioxidant activities. A total of 74 compounds were identified by Gas chromatography–mass spectrometry (GC-MS) from three cultivars, Peruvian red (PR), Peruvian green (PG), and Criolla (Cr), collected in distinct regions of Campeche, Mexico: Bécal (Be), Calkiní (Ca), and Bacabchén (Ba). The chemical classes identified included sesquiterpenes, sesquiterpenoids, alkanes, quinones, tocopherols, and sterols. Principal component analysis (PCA) indicated a clear separation of PRCa, PRBa, and CrBe from the other samples, with 86% of the total variation explained by 22 components. In PRCa (+)-ledol, (E)-β-farnesene, germacrene D, cis-β-santalene, and α-bisabolol were found abundantly. PRBa showed an abundance of β-elemene and moderate levels of caryophyllene oxide, guaiol, and γ-sitosterol. CrBe contained abundant (−)-spathulenol and phytol. The antimicrobial activity against Staphylococcus aureus showed that PRCa extracts exhibited the largest inhibition zones (23.5 ± 2.12 mm), statistically influenced by geographic origin (p = 0.0005). Conversely, PRBe and PRBa showed higher total polyphenol content and antioxidant activity, with the geographic origin × variety interaction significantly influencing these traits (p < 0.001). The findings highlight the importance of B. orellana, particularly the Peruvian red variety, as a valuable source of bioactive secondary metabolites and underscore the influence of cultivar phenotype and geographic origin on phytochemical variability and its antimicrobial and antioxidant properties. Full article