Search Results (11)

Two monoterpenoid lactones, loliolide (1) and epi-loliolide (2), were isolated from the crude dichloromethane extract of a microalga, Thalassiosira sp.). The structures of loliolide (1) and epi-loliolide (2) were elucidated by 1D and 2D NMR analysis, as well as a comparison of their ¹H or/and ¹³C NMR data with those reported in the literature. In the case of loliolide (1), the absolute configurations of its stereogenic carbons were confirmed by X-ray analysis, whereas those of epi-loliolide (2) were determined by NOESY correlations. Loliolide (1) and epi-loliolide (2) were tested for their growth inhibitory activity against two Gram-positive (Staphylococcus aureus ATCC 29213, Enterococcus faecalis ATCC 29212) and two Gram-negative (Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853) bacteria, as well as one clinical isolate (E. coli SA/2, an extended-spectrum β-lactamase producer-ESBL) and two environmental isolates, S. aureus 74/24, a methicillin-resistant (MRSA), and E. faecalis B3/101, a vancomycin-resistant (VRE) isolates. The results showed that none of the tested compounds exhibited antibacterial activity at the highest concentrations tested (325 μM), and both revealed low antioxidant activity, with ORAC values of 2.786 ± 0.070 and 2.520 ± 0.319 µmol TE/100 mg for loliolide (1) and epi-loliolide (2), respectively. Full article

Radix paeoniae rubra, known as red peony root, is derived from the dried roots of Paeonia lactiflora pall or Paeonia veitchii lynch from the Ranunculaceae family. It is recognized for its properties of clearing heat, cooling blood, dispelling stasis, and alleviating pain, making it one of the most commonly used herbs in traditional Chinese medicine. Total paeony glycosides (TPGs) are identified as the principal active constituents of Radix paeoniae rubra, comprising monoterpenoid compounds with a cage-like pinane structure and monoterpenoids with a lactone structure. This review summarizes the chemical constituents and pharmacological effects of TPGs, with the aim of elucidating their relationships. Full article

Caoyuanheimo-1 (Agaricus sp.) is a delectable mushroom native to Inner Mongolia, China, belonging to the Agaricus genus and valued for both its edible and medicinal properties. Although it has been cultivated to a certain extent, the molecular mechanisms regulating its development remain poorly understood. Building on our understanding of its growth and development conditions at various stages, we conducted transcriptomic and metabolomic studies to identify the differentially expressed genes (DEGs) and metabolites throughout its growth cycle. Simultaneously, we analyzed the synthesis pathways and identified several key genes involved in the production of terpenoids, which are secondary metabolites with medicinal value widely found in mushrooms. A total of 6843 unigenes were annotated, and 449 metabolites were detected in our study. Many of these metabolites and differentially expressed genes (DEGs) are involved in the synthesis and metabolism of amino acids, such as arginine, cysteine, methionine, and other amino acids, which indicates that the genes related to amino acid metabolism may play an important role in the fruiting body development of Caoyuanheimo-1. Succinic acid also showed a significant positive correlation with the transcriptional level changes of nine genes, including laccase-1 (TRINITY_DN5510_c0_g1), fruiting body protein SC3 (TRINITY_DN3577_c0_g1), and zinc-binding dihydrogenase (TRINITY_DN2099_c0_g1), etc. Additionally, seventeen terpenoids and terpenoid-related substances were identified, comprising five terpenoid glycosides, three monoterpenoids, two diterpenoids, one sesquiterpenoid, one sesterterpenoid, two terpenoid lactones, and three triterpenoids. The expression levels of the genes related to terpenoid synthesis varied across the three developmental stages. Full article

Diabetes mellitus (DM) is a chronic metabolic disorder characterized by hyperglycemia, which affects multiple tissues including kidneys. Soursop leaves (Annona muricata) are known to have antidiabetic potential, but their molecular and cellular effects are poorly characterized. We identified the bioactive compounds in soursop leaf ethanol extract (SLEE). The SLEE substances demonstrated the total alkaloid and total flavonoid contents. Twelve bioactive compounds profiles were identified in SLEE classified as alkaloid, flavonol glycoside, and monoterpenoid lactone derivatives. The SLEE treatments in mice were performed by dividing Swiss Webster mice into five groups, including negative and positive controls and three experimental groups provided with SLEE (doses 150, 300, and 600 mg/kg BW) for 14 days. The mice in the experimental groups were treated with alloxan to induce diabetes. The renal samples were stained for H&E for morphological changes. However, 600 mg/kg of SLEE showed a significant effect (p < 0.05) on the height of the Bowman’s space and prevented the tubularization of the left kidney’s glomerulus (p < 0.05). Altogether, we report no significant difference in the glomerular diameter, the thickness of the proximal convoluted tubules, the height of the Bowman’s space, and the glomerular tubularization after 14 days of treatment with SLEE. Full article

Regulating the adipogenic differentiation mechanism is a valid and promising mechanism to battle obesity. Natural products, especially phytochemicals as nutraceuticals, are important lead molecules with significant activities against obesity. Loliolide is a monoterpenoid hydroxyl lactone found in many dietary plants. The effect of loliolide on adipogenic differentiation is yet to be determined. Therefore, the present study aimed to evaluate its anti-adipogenic potential using human bone marrow-derived mesenchymal stromal cells (hBM-MSCs) and assess its mechanism of action. Adipo-induced hBM-MSCs were treated with or without loliolide and their adipogenic characteristics were examined. Loliolide treatment decreased the lipid accumulation and expression of adipogenic transcription factors, PPARγ, C/EBPα, and SREBP1c. Adipo-induced hBM-MSCs also displayed increased AMPK phosphorylation and suppressed MAPK activation following loliolide treatment according to immunoblotting results. Importantly, loliolide could stimulate Wnt10b expression and active β-catenin translocation to exert PPARγ-linked adipogenesis suppression. In conclusion, loliolide was suggested to be a potential anti-adipogenic agent which may be utilized as a lead compound for obesity treatment or prevention. Full article

Balanced nutritional intake is essential to ensure that insects undergo adequate larval development and metamorphosis. Integrative multidisciplinary approaches have contributed valuable insights regarding the ecological and evolutionary outcomes of plant–insect interactions. To address the plant metabolites involved in the larval development of a specialist insect, we investigated the development of Chlosyne lacinia caterpillars fed on Heliantheae species (Tithonia diversifolia, Tridax procumbens and Aldama robusta) leaves and determined the chemical profile of plants and insects using a metabolomic approach. By means of LC-MS and GC-MS combined analyses, 51 metabolites were putatively identified in Heliantheae species and C. lacinia caterpillars and frass; these metabolites included flavonoids, sesquiterpene lactones, monoterpenoids, sesquiterpenoids, diterpenes, triterpenes, oxygenated terpene derivatives, steroids and lipid derivatives. The leading discriminant metabolites were diterpenes, which were detected only in A. robusta leaves and insects that were fed on this plant-based diet. Additionally, caterpillars fed on A. robusta leaves took longer to complete their development to the adult phase and exhibited a greater diapause rate. Hence, we hypothesized that diterpenes may be involved in the differential larval development. Our findings shed light on the plant metabolites that play roles in insect development and metabolism, opening new research avenues for integrative studies of insect nutritional ecology. Full article

Parkinsons Disease (PD) is the second most common neurodegenerative disease worldwide, and is characterized by a progressive degeneration of dopaminergic neurons. Without an effective treatment, it is crucial to find new therapeutic options to fight the neurodegenerative process, which may arise from marine resources. Accordingly, the goal of the present work was to evaluate the ability of the monoterpenoid lactone Loliolide, isolated from the green seaweed Codium tomentosum, to prevent neurological cell death mediated by the neurotoxin 6-hydroxydopamine (6-OHDA) on SH-SY5Y cells and their anti-inflammatory effects in RAW 264.7 macrophages. Loliolide was obtained from the diethyl ether extract, purified through column chromatography and identified by NMR spectroscopy. The neuroprotective effects were evaluated by the MTT method. Cells’ exposure to 6-OHDA in the presence of Loliolide led to an increase of cells’ viability in 40%, and this effect was mediated by mitochondrial protection, reduction of oxidative stress condition and apoptosis, and inhibition of the NF-kB pathway. Additionally, Loliolide also suppressed nitric oxide production and inhibited the production of TNF-α and IL-6 pro-inflammatory cytokines. The results suggest that Loliolide can inspire the development of new neuroprotective therapeutic agents and thus, more detailed studies should be considered to validate its pharmacological potential. Full article

Tisochrysis lutea is a marine haptophyte rich in omega-3 polyunsaturated fatty acids (e.g., docosahexaenoic acid (DHA)) and carotenoids (e.g., fucoxanthin). Because of the nutraceutical applications of these compounds, this microalga is being used in aquaculture to feed oyster and shrimp larvae. In our earlier report, T. lutea organic crude extracts exhibited in vitro cytotoxic activity against human hepatocarcinoma (HepG2) cells. However, so far, the compound(s) accountable for the observed bioactivity have not been identified. Therefore, the aim of this study was to isolate and identify the chemical component(s) responsible for the bioactivity observed. Bioassay-guided fractionation through a combination of silica-gel column chromatography, followed by preparative thin layer chromatography (PTLC), led to the isolation of two diastereomers of a monoterpenoid lactone, namely, loliolide (1) and epi-loliolide (2), isolated for the first time in this species. The structural elucidation of both compounds was carried out by GC-MS and 1D (¹H and ¹³C APT) and 2D (COSY, HMBC, HSQC-ed, and NOESY) NMR analysis. Both compounds significantly reduced the viability of HepG2 cells and were considerably less toxic towards a non-tumoral murine stromal (S17) cell line, although epi-loliolide was found to be more active than loliolide. Full article

Numerous gram-negative phytopathogenic and zoopathogenic bacteria utilise acylated homoserine lactone (AHL) in communication systems, referred to as quorum sensing (QS), for induction of virulence factors and biofilm development. This phenomenon positions AHL-mediated QS as an attractive target for anti-infective therapy. This review focused on the most significant groups of plant-derived QS inhibitors and well-studied individual compounds for which in silico, in vitro and in vivo studies provide substantial knowledge about their modes of anti-QS activity. The current data about sulfur-containing compounds, monoterpenes and monoterpenoids, phenylpropanoids, benzoic acid derivatives, diarylheptanoids, coumarins, flavonoids and tannins were summarized; their plant sources, anti-QS effects and bioactivity mechanisms have also been summarized and discussed. Three variants of plant-derived molecules anti-QS strategies are proposed: (i) specific, via binding with LuxI-type AHL synthases and/or LuxR-type AHL receptor proteins, which have been shown for terpenes (carvacrol and l-carvone), phenylpropanoids (cinnamaldehyde and eugenol), flavonoid quercetin and ellagitannins; (ii) non-specific, by affecting the QS-related intracellular regulatory pathways by lowering regulatory small RNA expression (sulphur-containing compounds ajoene and iberin) or c-di-GMP metabolism reduction (coumarin); and (iii) indirect, via alteration of metabolic pathways involved in QS-dependent processes (vanillic acid and curcumin). Full article

Daphnauranins C–E (compounds 1–3), two sesquiterpenoids and one monoterpenoid were isolated from the roots of Daphne aurantiaca Diels. Daphnauranin C is a 9-O-13 etherified and hydroperoxy-substituted guaiane sesquiterpenoid, daphnauranin D is a guaiane sesquiterpenoid ketal, and daphnauranin E is a monoterpenoid lactone. Their structures were elucidated by comprehensive analyses of MS, 1D NMR, and 2D NMR spectroscopic data. In an anti-feeding activities test, daphnauranins C–E showed activity against male fruit fly with anti-feeding indexes (AI) up to 39.1, 39.2, and 27.8% respectively, at 1 mM. Full article

A new C₉ monoterpenoid acid (litseacubebic acid, 1) and a known monoterpene lactone (6R)-3,7-dimethyl-7-hydroxy-2-octen-6-olide (2), along with three known compounds – vanillic acid (3), trans-3,4,5-trimethoxylcinnamyl alcohol (4), and oxonantenine (5) – were isolated with bioassay-guided purification from the fruit extract of Litsea cubeba collected in Tibet. The structure of 1 was elucidated by MS, ¹H-NMR, ¹³C-NMR, COSY, HSQC, HMBC, NOE spectral data as 2,6-dimethyl-6-hydroxy-2E,4E-hepta-2,4-diene acid. Additionally 33 compounds were identified from the essential oil of L. cubeba. The preliminary bioassay results showed that 1 and 2 have good fungicidal activities against Sclerotinia sclerotiorum, Thanatephorus cucumeris, Pseudocer-cospora musae and Colletotrichum gloeosporioides at the concentration of 588 and 272 μM, and the essential oil has good fungicidal activities against T. cucumeris and S. sclerotiorum, with IC₅₀ values of 115.58 and 151.25 μg/mL, repectively. Full article