Records of Natural Products Articles

Aconitaimine A, a new hetidine-type C20-diterpenoid alkaloid (1), and three known aconitine-type C19-diterpenoid alkaloids (2-4) were isolated from the roots of Aconitum taipeicum. The structures of all isolates were identified by spectroscopic methods and comparison with literature data. Compounds 1 and 2 showed inhibition of nitric oxide production in RAW 264.7 macrophages stimulated by lipopolysaccharide with IC50 values of 30.5 and 4.7 μM compared to positive control (dexamethasone, IC50 = 12.9 μM).

Filamentous fungi are very well known for producing a wide variety of secondary metabolites with important biological effects. In our study chemical exploration of the Nicotiana tabacum symbiotic fungus Aspergillus japonicus TE-739D led to the discovery of a new polyketide derivative, namely (3S,4E,6E,9S)-9-hydroxy-3,7-dimethyldeca-4,6-dienoic acid (1), along with three previously reported compounds 2−4. The structures of these compounds were elucidated by using HRESIMS, NMR spectroscopic analyses, and quantum chemical calculations. Compounds 3 and 4 showed strong antibacterial activity against four representative bacterial strains including two Gram-negative species (Agrobacterium tumefaciens and Xanthomonas oryzae) and two Gram-positive Bacillus species (B. cereus and B. subtilis), with MIC values range from 1 to 16 μg/mL, respectively.

This study involved the extraction, isolation, structural elucidation of a new analogue of zhepiresionol, as well as five lignans previously identified, from the plant Ailanthus altissima (Mill.) Swingle. The structural elucidation was accomplished through comprehensive analyses of various spectroscopic data, which included HRESIMS, UV, IR, and NMR, along with a comparison of ECD curves. At a concentration of 15 µM, Compound 1 showed the capacity to suppress IL-1β and IL-6 expression in RAW 264.7 cells that were Lipopolysaccharide-stimulated.

A new dammarane triterpenoid glycoside cyclocarioside Z14 (1) and four known compounds (2-5) were isolated from the dichloromethane extract of the leaves of Cyclocarya paliurus. The chemical structures were elucidated by the extensive spectroscopic data analysis of NMR, HR-ESI-MS, and acid hydrolysis. All isolated compounds were assayed on the cytotoxicity against seven human cancer cell lines. The compounds 1 and 3 showed moderate cytotoxicity against MCF-7 cells with an IC50 value of 29.51 μM and 33.88 μM.

In this study, chemical investigation of the aerial parts of the medicinal plant Tinospora sinensis yielded five compounds (1-5), including a new acyclic compound (1) and four known compounds (2-5). Their structures were determined by extensive analysis of the spectroscopic data, including 1D (1H and 13C NMR) and 2D NMR data (HSQC, COSY, and HMBC). Compounds 3-5 were identified to be stearic acid (3), abscisic acid (4), and blumenol A (5) based on comparisons of the NMR data with those reported in the literature. The NMR data for 2-hydroxy methyl stearate (2) were reported for the first time in CDCl3 in this study. The compounds were evaluated for their antitumor potential against A549 cell line, while all were inactive (25 mM). Besides, compound 1 demonstrated marginal inhibition (19.35%) of LPS-induced NO production in RAW 264.7 cells (50 mM).

Bioassay-guided fractionation of extracts of aerial parts from Lippia callicarpifolia usingvia chromatographic techniques led to the isolation of two D:C-friedours-7-ene compounds, namely D:C-3-oxo-friedours-7-en-28-oic acid (1) and a new callicarpifolic acid (2). Furthermore, additional known compounds, β-sitosterol glucoside (3) and genkwanin (4) were also identified. The structures of the natural products were established by 1D and 2D NMR, IR, and spectrometric analysisanalyses. In the antifungal assays, Fusarium sporotrichioides NRLL was sensitive to compounds 1 and 4 in the concentration range of 0.250-–1 mg/mL. The docking investigation revealed high inhibition of the trichodiene synthase enzyme by compound 4.

Phytochemical investigation of 70% ethanol extract of Euphorbia helioscopia led to eight diterpenoids, including four jatrophane-type (1–4), three abietane-type (5–7) and one lathyrane-type (8). Among them, (5E,11E)-3β-benzoyloxy-7β,14α,15β-trihydroxyjatropha-9-one (1) was a new jatrophane diterpenoid. An extensive array of spectral analyses, including HR-ESI-MS, IR, UV, 1D and 2D NMR, as well as quantum chemical calculations of ECD curve, were utilized for their structural elucidation. Bioassay results showed that compounds 2–3 and 6–8 could significantly inhibit NO release on LPS-induced RAW 264.7 cells, especially for jatrophane diterpenoid 3 and abietane diterpenoid 8 that showed stronger activities with the IC50 values of 9.16 ± 0.70 and 5.74 ± 0.27 μM.

NNotopterygium incisum is widely used in clinical practice because of its complex chemical composition and remarkable pharmacological effects. In this study, a previously undescribed lignan (1) was isolated from N. incisum. Its structure was evaluated through examinations of the NMR, HREIMS data and ECD calculation. Compound 1 demonstrated significant anti-inflammatory potential by inhibiting the secretion of nitric oxide (NO) in lipopolysaccharide (LPS)-induced macrophages, with an IC50 value of 3.57 μM.

A new benzofuranside compound (eupbenzofuranside C) was isolated from the n-butanol fraction of ethanol extract of Eupatorium chinense L. along with three known compounds. The structures of the isolated compounds were elucidated by 1D and 2D NMR techniques, mass spectrometry and circular dichromism (CD). The isolated compounds were investigated for their α-glucosidase and PTP1B inhibitory activities by p-nitrophenyl-β-galactopyranoside method and p-nitrophenyl phosphate method, respectively. Although eupbenzofuranside C showed potential dual inhibitory activity against α-glucosidase and PTP1B with IC50 values of 40.07±0.38 μg/mL and 39.37±0.36 μg/mL, respectively, these values were determined to be far from the data of the positive control acarbose. In contrast, compound 2 showed inhibitory activities against both α-glucosidase and PTP1B with IC50 (μg/mL) values of 4.83±0.29 and 17.29±0.17, which were closer to acarbose. Compounds 3 and 4 showed no inhibition in both tests (IC50 > 50 μg/mL). In addition, the interactions of compound 1 with α-glucosidase and PTP1B were analyzed using the active site analysis for computer-aided drug design.

Nine known compounds were isolated from the fruitless bunches of Washingtonia filifera, an underutilized agricultural waste, using NMR and mass spectrometry. The identified compounds included β-sitosteryl oleate (1), oleic acid (2), β-sitosterol (3), threo-2,3-bis-(4-hydroxy-3-methoxyphenyl)-3-methoxypropanol (4), syringaresinol (5), diosmetin (6), tricin (7), daucosterol (8), and luteolin-7-O-β-D-glucoside (cynaroside) (9). In vitro acetylcholinesterase (AChE) inhibition assays revealed that compound 5 exhibited the strongest activity (IC50 = 29.75 µM), followed by compounds 4 and 6. Docking studies indicated significant interactions of the active compounds with key AChE residues, particularly Trp86 and Tyr341. ADME predictions further supported the drug-likeness of compounds 4 and 5. These results highlight the significance of W. filifera agricultural waste as a source of bioactive compounds, particularly with neuroprotective effects.

Fusarium solani 2024f-xx, an endophytic fungus derived from the marine brown algae Sargassum thunbergii, was chemically studied. As a result, two polyhydroxy compounds, namely fusasolpolyol A (1) and (4E,8E,12E)-2,3,7,11-tetrahydroxy-2,4,6,8,10,12-hexamethyltetradeca-4,8,12-trienoic acid (2), as well as two known drimane-type sesquiterpenoids (3 and 4) were isolated and identified. The structures of the isolated compounds were ascertained by means of specific spectroscopic methods (mainly determined by HRESIMS and 1D/2D NMR data). Compound 1 was identified as a new compound. In the cytotoxic assays, compound 2 revealed moderate activity against the human gastric carcinoma cell MKN-45 and the human pancreatic cancer cell PATU8988T, with the respective IC50 values of 19.6 ± 1.2 μM and 26.3 ± 0.9 μM.

This paper mainly provides a systematic review of the chemical constituents and biological activities of Fomes fomentarius. As a widely distributed medicinal fungus, F. fomentarius has a long history of application in traditional medicine. Rich in chemical constituents, it contains over a hundred compounds such as steroids, triterpenes, and fatty acids. Pharmacological studies have demonstrated that this fungus exhibits multiple activities, including antitumor, immunomodulatory, antioxidant, antibacterial, anti-inflammatory and analgesic, antidiabetic, anti-hypoxic, and hepatoprotective effects. However, our current understanding of its action mechanisms and the synergistic effect among components remains limited. This review provides crucial references for further research and development of F. fomentarius.

Fusarinene A (1), a previously undescribed trichothecene sesquiterpene, and three known compounds, 4β-hydroxytrichotheca-9,12-diene (2), trichodermol (3), and trichodermin (4), were isolated from the extract of Fusarium sp. XPW68. Their structures and relative configurations were identified by detailed analysis of nuclear magnetic resonance (NMR) and high-resolution electrospray ionization mass spectrometry (HRESIMS) data. In the cytotoxic assay, compounds 1-4 exhibited selective or potent inhibition against five human osteosarcoma cell lines including 143B, MG-63, SaOS-2, SW1353, and U2OS, with IC50 values ranging from 0.8 to 48.2 μM.

The consumption of raspberry (Rubus idaeus L.) leaves has a long tradition, especially as a "general pregnancy tea", although the scientific data are insufficient and contradictory. Phytochemical comparation of extracts from cultivated and wild raspberry leaves, in silico prediction of their biological activities and acute toxicity followed by in vitro antiradical activity and effects on the viability/proliferation of HeLa cells and isolated rat uterus were performed. Leaves from cultured (v. Polka) and wild individuals were extracted with distilled water, 70% v/v ethanol or 70% v/v methanol. All samples exhibited high polyphenol content and antiradical activity, with the 70% v/v ethanol extract of wild R. idaeus showing the strongest free radical scavenging ability. In silico analyzes predicted that raspberry leaves possess numerous compounds with anti-inflammatory, apoptosis-agonistic, antinociceptive and NO signaling-related activities. Potentially toxic levels of the tested compounds could not be achieved with regular tea drinking. The tested extracts have no noticeable effects on the viability/proliferation of HeLa cells. The effects on spontaneous contraction of the isolated rat uterus were modest. Although safety is not a concern, further studies are needed to justify or deny the efficacy of raspberry leaf tea in folk medicine for healthy pregnancy and easy delivery.