Natural Product Research最新文献

The ecologically and floristically contrasting Brazilian Caatinga and Atlantic Forest biomes have been underexplored phytochemically. Evidence from studies based on univariate and multivariate environmental, phenological, morphometric and palynological data recognised Metternichia macrocalyx and Metternichia principis as two distinct species rather than mere varieties, each inhabiting one of these biomes, a view only revised in 2023, although there is no chemical data to corroborate this information. Therefore, we isolated two major compounds from M. macrocalyx and performed a metabolic profile study of M. macrocalyx and M. principis by LC-ESI-MS/MS. The data were processed in MS-DIAL with libraries from GNPS, Massbank, MassbankEU and Respect, and a molecular network was generated that led to the annotation of 49 compounds from these species. Finally, the data underwent to principal component analysis to show the main differences and similarities between the metabolic profiles, which were relevant only for taxonomic delimitation of the genus.

This research centred on investigation of chemical composition, antimicrobial, and antioxidant potential of essential oil from various parts of Solidago virgaurea L. Essential oils (EOs) were isolated using hydrodistillation method. The yield variation observed in EO were (0.15%-1.1% v/w) highest in flowers (1.1%). GC-FID/GC-MS based metabolite profiling had shown overall 32 metabolites, including monoterpenes, oxygenated monoterpenes, and sesquiterpene hydrocarbons. Major constituents in flowers were α-pinene (33.43 ± 0.13%), limonene (19.33 ± 0.08%), germacrene D (16.48 ± 0.21%), and sabinene (3.72 ± 0.0%). The antibacterial activity, determined through disc diffusion, and MIC assays, flowers EO exhibiting the highest inhibition zone (24.33 ± 1.7 mm) against Micrococcus luteus MTCC 2470, while the leaves EO had the lowest MIC (2.5% v/v) against Pseudomonas aeruginosa MTCC 2453. whereas, EO from leaves showed strong antioxidant activity (IC₅₀ ABTS = 18.98 ± 0.08 μg/mL and IC₅₀ DPPH = 6.59 ± 0.03 μg/mL). Network pharmacological analysis also revealed MAPK1 (Mitogen-Activated Protein Kinase 1) exhibited the highest score of 20.

This study aims to isolate an undescribed eudesmane-type sesquiterpenoid, phyllunone A (1), along with 5 known sesquiterpenoids from n-hexane extract of Aglaia pachyphylla stem bark. The structural elucidation of compound 1 was achieved using NMR, HRMS, ECD, and was further supported by computational calculation (TD-DFT and NMR DP4+). Phyllunone A (1) represented a new eudesmane skeleton bearing a 2,4(11)-dien-1-one moiety. In addition, compounds 1 to 6 were evaluated against MCF-7 breast cancer cells and anti-inflammatory activity (TNF-α production) in RAW 264.7 cells induced by LPS. The results revealed that only compounds 2-3 exhibited weak cytotoxicity (IC₅₀ 343 and 206 µM), while the others were inactive. In anti-inflammatory assay, compound 1 showed the highest inhibition of TNF-α production (49.3%), indicating its potential as a non-cytotoxic anti-inflammatory agent.

A series of nine diphyllin thioether and four ether derivatives were designed and successfully synthesised via epoxide nucleophilic ring-opening reaction. These compounds demonstrated pronounced cytotoxic activity against the human cancer cell lines HepG2, HCT-15, and A549. Notably, thioether derivative 3a exhibited the most potent cytotoxicity, with IC₅₀ values ranging from 0.03 to 0.63 µM. Research on the antitumor mechanism revealed that compound 3a selectively inhibits the expression of glutathione peroxidase GPX4, inducing ferroptosis in A549 cells.

Antibiotic-resistant bacteria are continuously increasing the prevalent level of bacterial infection, making it a serious public health threat. In the search for solutions, natural products have emerged as promising allies that could enhance the efficacy of conventional antibiotics. This study examined the antibacterial interactions between the leaf extracts of Aristotelia chilensis (Mol.) Stuntz (maqui) and the antibiotics ampicillin and chloramphenicol using a checkerboard assay; the test were conducted against the pathogenic bacteria Escherichia coli, Staphylococcus aureus, and Salmonella typhi. The minimum inhibitory concentrations (MIC) of maqui leaf extract were 12.5, 0.04, and 1.56 mg/mL against E. coli, S. aureus, and S. typhi, respectively. Combining the extract with ampicillin or chloramphenicol, the extract reduced the MICs of the antibiotics by up to six-fold. The interaction of maqui leaf extracts with conventional antibiotics was found to significantly enhance antibacterial activity, reducing required antibiotic doses and highlighting their relevance in combating antimicrobial resistance.

In the present study, we aimed to report the identified chemical composition of methanol and n-butanol extracts obtained from the aerial parts of the Algerian Pardoglossum cheirifolium (L.) Barbier & Mathez. Heliosupine N-oxide (1) was isolated from the n-butanol extract and structurally characterised by extensive NMR and ESI-MS/MS data. LC-DAD-ESI/MS analysis on methanol extract aimed at determining pyrrolizidine alkaloids of which the Pardoglossum genus is a rich source, led to the proposed identification of lycopsamine N-oxide (2), echinatine N-oxide (3), dihydrolycopsamine (4), dihydroechinatine (5), 7-acetyl dihydrolycopsamine (6), 7-acetyllycopsamine N-oxide (7), 3'-acetylviridiflorine (8), vulgarine (10), and heliosupine (16). The glycosylated flavonols quercetin 3-O-rhamnopyranoside-(1→2)-glucopyranosyl-(1→6)-rhamnopyranoside (9), kaempferol 3-O-L-rhamnopyranosyl-(1→2)-rhamnopyranosyl-(1→6)-glucopyranoside (11), rutin (12), kaempferol 3-O-rutinoside (13), in addition to 3,4,5-trihydroxycinnamic acid glucopyranoside (14) and 3,5-dihydroxycinnamic acid-O-diglucopyranoside (15), were also identified. For the first time, we report the known metabolites 2 - 11 and 13 - 15 in the studied plant, both reported as Pardoglossum cheirifolium and Cynoglossum cheirifolium.

This work investigated the efficacy of rosemary essential oil (REO) and Boswellia serrata extracts (BSE) against Anisakis larvae for possible industrial applications. In-vitro assays exposed Anisakis type I larvae to various media containing REO (1-5%) or BSE (1-5%) with spermidine and ferulic acid at different temperatures and times. Ex-vivo trials in experimentally infested anchovy fillets were carried out only for REO. REO demonstrated significant anisakicidal activity, achieving the fastest efficacy in oil (15h at 4 °C with 5% REO). Lower concentrations (1%) showed limited effectiveness. BSE achieved a maximum 92% larval devitalisation at 5%. Ex-vivo experiments revealed initial devitalisation after 72h, reaching 100% by 168h in anchovy fillets with 5% REO-oil at 20 °C. REO exhibited substantial anisakicidal effects in marinated anchovies under refrigeration and lipid conditions. These findings highlight REO as a promising natural additive for enhancing marinated fish product safety, offering an alternative or complement to freezing for Anisakis risk management.

In the past few decades, there has been a growing interest in fish oils because of their significant health benefits. Marine Polynemus paradiseus fish locally named as topse fish are indigenous source which thrives in West Bengal's marine areas, India. Furthermore, there is a limitation of current study on P. paradiseus FO. The present study aimed to investigate P. paradiseus FO's chemical index and antibacterial effectiveness against the pathogenic microorganisms. The quality indexes of oil were conformed to Codex Alimentarius Standard. The broth microdilution method was used to assess the antibacterial properties of P. paradiseus FO and its interaction with antibiotics. Inhibition zones and MIC value of P. paradiseus FO against bacterial strains ranged from 13 to 18 mm and from 15 to 55 μg/mL, respectively. Our findings indicated P. paradiseus FO may be regarded as a viable antibacterial agent for enhancing food safety through the management of foodborne infections.

From the culture of the Antarctic psychrophilic fungus Cadophora malorum, a partially acetylated 3,5-dihydroxydecanoic acid dimer (1) was isolated and identified. The absolute configuration of the stereogenic centres of the 3,5-dihydroxydecanoic acid moiety was chemically determined through the formation of a dioxane derivative of the methyl ester. Compound 1 displayed very good antifungal activity against several phytopathogenic fungi, with MIC values between 6.25 and 25 µg/mL. A lipidomics approach was carried out to assess the effect of compound 1 on a culture of a phytopathogenic strain of Fusarium solani, which led to an increase of diglycerides in the extract of the mycelium.

Salvia veneris Hedge (Krythean sage), an endemic species of Cyprus, was investigated for its phenolic compounds and wound healing through the development of an ointment. Phenolic constituents of S. veneris ethanol extract (SVEE) were characterised by LC-MS/MS, and total phenolic content was determined using the Folin-Ciocalteu method. Twenty-two phenolic compounds were identified, with caffeic acid as the major compound and a total phenolic content of 144.6 mg GAE/g. SVEE enhanced fibroblast proliferation in the MTT assay (IC₅₀ = 56.01 ± 1.34 μg/mL) while exhibiting low cytotoxicity. In vivo evaluation of SVEE-based ointment using an excision wound model demonstrated significant, dose-dependent healing activity, with increased re-epithelialization and accelerated wound contraction (91.17 ± 1.84% by day 15) compared with control groups. These findings indicate that the rich phenolic composition of S. veneris contributes to its potent wound-healing activity, supporting the potential of SVEE-based formulations as promising natural therapeutics for wound healing.