A new acetophenone (1) and 14 known compounds (2–15) were isolated from the roots of Melicope pteleifolia. Their structures were elucidated by means of comprehensive spectroscopic analysis, including 1D, 2D NMR, and HR-ESI-MS, as well as though comparison with published data. All isolated compounds were assessed for their in vitro cytotoxicity against human cancer cell lines using the SRB method. Among them, compound 13, one of the flavonoids, exhibited the strongest cytotoxic activity, with an IC50 value of 14.79 μM. Further investigation revealed that compound 13 could induce HCT116 cell apoptosis by suppressing the cleavage of Cleaved Caspase-3 and Cleaved PARP.
Ten undescribed coumarins, including five pairs of enantiomers (±)-toddacoumalin C (3a/3b), (±)-toddacoumalin D (4a/4b), (±)-toddacoumalin E (5a/5b), (±)-toddacoumalin F (6a/6b), and (±)-toddacoumalin I (9a/9b), along with 13 known compounds (11-23) were isolated from the roots of Toddalia asiatica. Their structures were elucidated by spectroscopic analyses, and absolute configurations were determined via electronic circular dichroism (ECD) calculations and Mo2(OAc)4-induced ECD. Notably, the isolation of toddacoumalin H (8) provided crucial evidence to revise the double bond geometry of the previously reported toddasirin F from E to Z. All compounds were assessed for their anti-inflammatory potential against lipopolysaccharide-induced nitric oxide (NO) production in RAW264.7 cells. Compound 17 emerged as the most potent inhibitor, exhibiting an IC50 value of 1.109 μM, which was approximately 5-fold more potent than the positive control indomethacin (IC50 = 5.625 μM). Considering the interplay between oxidative stress and inflammation, we further evaluated the antioxidant capacity of the isolates using the FRAP assay. Compounds 10 and 17 exhibited promising antioxidant effects, with the values (expressed as Fe2+ equivalent, mM) of 5.786 ± 0.049 and 2.275 ± 0.070, respectively. Cytotoxicity assays further confirmed that compound 17 had an acceptable safety profile in normal cells. Collectively, these findings highlight compound 17 as a promising dual-functional lead candidate with significant anti-inflammatory and antioxidant activities.
Marine exometabolites exert a substantial and dominant effect on interactions among marine benthic microorganisms. Nevertheless, the relationship between exometabolites and the community structure of benthic fungi remains unclear. In this study, we examined the abundance and diversity of fungal communities in various marine benthic habitats and elucidated their correlation with key elements, such as carbon and nitrogen, abiotic factors, such as pH, salinity, and depth, and marine exometabolites using various environmental metabolomic techniques. We found that the marine exometabolites primarily comprised organic acids and amino acids and their derivatives, which exhibited a broad negative and positive correlation with the Shannon of benthic fungal communities, respectively. Furthermore, the contribution of exometabolites to the changes in Shannon and benthic fungal community structure was higher than those of environmental factors, and organic acids exerted a highly significant impact on the fungal community structure. Key fungal taxa, such as Alternaria sp., showed significant association with organic acids and amino acids and their derivatives in co-occurrence networks. Structural equation modeling revealed an intuitive and concise interaction network between fungi, the environment, and marine exometabolites. Thus, the findings of this study provide new insights into the mechanisms underlying the maintenance of benthic fungal communities.IMPORTANCEResearch on the diversity and community structure of marine benthic fungi is limited. This study explores the relationships between these fungal communities and key elements (carbon and nitrogen), abiotic factors (pH, salinity, and depth), and exometabolites, with a focus on the role of marine exometabolites. The findings demonstrate that exometabolites, particularly organic acids, significantly influence the structure of benthic fungal communities. These results enhance our understanding of successional processes within these communities and clarify the interactions between benthic fungi and exometabolites, offering valuable insights into the formation of marine benthic fungal communities.
Ferns have increasingly attracted attention as underexplored sources of structurally diverse secondary metabolites with ecological and pharmacological significance. Species of the genus Dicranopteris have long been used in traditional medicine for their health-promoting properties; however, their phytochemical diversity, pharmacological activities, and ecological functions have not yet been comprehensively summarized. In this review, we systematically summarized and critically evaluated studies published between 1980 and 2025, based on literature retrieved from PubMed, Scopus, Google Scholar, Web of Science, and other scientific databases. To date, a total of 87 secondary metabolites have been reported from Dicranopteris species and are classified herein into four major structural categories—flavonoids, terpenoids, phenolics (excluding flavonoids), and others—according to their core skeletal frameworks. Many of these compounds exhibit notable pharmacological activities, including antinociceptive, antioxidant, anti-inflammatory, antipyretic, antiviral, gastroprotective, antibacterial, and allelopathic effects, as has been demonstrated in both in vitro and in vivo studies. In addition to their medicinal relevance, Dicranopteris species also display important ecological functions, such as rare-earth element enrichment and allelopathic interactions that influence plant community dynamics. By integrating phytochemical, pharmacological, and ecological evidence, this review highlights the multifaceted value of Dicranopteris and provides a systematic foundation for future research and potential applications in natural product chemistry, drug discovery, functional products, and ecological management.
Ulcerative colitis (UC) treatment is often limited by adverse reactions and high recurrence rates, highlighting the need for safer, more effective therapies. Citrus medica 'Fingered' (C. medica), known for its anti-inflammatory properties, remains underexplored, particularly its polysaccharide components. This study investigated the intestinal protective effects of C. medica polysaccharides extracted via hot water (HWE-CP) and characterized a primary fraction's structure. The dextran sulfate sodium -induced UC mouse model was used to evaluate the intestinal protective activity of HWE-CP, and one of the main fractions was characterized using HPGPC, HPAEC, FTIR, TGA, methylation, and NMR. The results indicated HWE-CP alleviated the UC symptoms in mice by reducing weight loss and disease activity, increasing colon length, minimizing intestinal mucosal damage, strengthening the intestinal barrier, lowering inflammatory factor expression, and balancing gut flora. The primary fraction, HWE-CP-2A, had a molecular weight of 38.28 kDa and comprise Rha, Ara, Gal, and GalA with molar rations of 1.57: 4.46: 2.50: 91.47. Its main chain was -*[4)-alpha-D-GalAp-6-O-CH3(1]5 -* 3,4)-alpha-D-GalAp-6-OCH3, with alpha-D-GalAp-(1-*) linked to the main chain via the C-3 bond. The polymerization degree was around 25. This study provides evidence for the structural with anti-UC relationships of HWE-CP and lays the foundation for the development of its related products.
By tracing the characteristic proton and carbon nuclear magnetic resonance signals of the furan ring and aldehyde group, four novel 5-hydroxymethylfurfural derivatives, fusaroxysporins A-D (1-4), together with 10 known compounds were obtained from the marine fungus Fusarium oxysporum SP7. Their structures were elucidated by comprehensive spectroscopic analysis. The possible biogenic synthesis pathways of these compounds were speculated. Compound 1 showed moderate cytotoxic activity against the human type II alveolar epithelial cell A-549 and the human hepatocarcinoma cell line HepG2 with IC50 values of 48.0 and 92.0 µM, respectively, while the other compounds had no activity (IC50 > 200 µM).
Filoviruses, mainly consisting of the two genera of Ebolavirus and Marburgvirus, are enveloped negative-strand RNA viruses that can infect humans to cause severe hemorrhagic fevers and outbreaks with high mortality rates. However, we still do not have effective medicines for treating these diseases. To search for effective drugs, we have identified three marine indole alkaloids that exhibit potent activities against filovirus infection. Thus, it is suggested that marine indole alkaloids can be a valuable compound source for filovirus drug screening and development. Since marine indole alkaloids comprise a large diverse group of secondary metabolites, their biological properties would be helpful for pharmaceutical drug development to treat various filovirus infections.
It is well known that Citrus medica 'Fingered' is an important industrial crop resource. Our previous study found that Citrus medica 'Fingered' polysaccharides via hot water extraction (HWE-CP) can alleviate ulcerative colitis by enhancing intestinal barrier and regulating intestinal flora. However, the large molecular weight of HWE-CP (35.15 kDa) limits its absorption by intestinal cells, thereby restricting its protective effects on the intestinal barrier. In this study, HWE-CP was chemically modified to obtain sulfated derivatives (S-HWE-CP) and carboxymethylated derivatives (C-HWE-CP). Subsequently, we investigated the physicochemical, structural characteristics, and protective abilities of these derivatives on the intestinal barrier. The results indicated that chemical modification led to significant changes in the molecular weight, monosaccharide composition and molar ratio, proportion of HG domains, Zeta potential, and thermal stability of HWE-CP. C-HWE-CP, with a degree of substitution of 1.12, most effectively promoted Occludin protein expression and enhanced the integrity of the cell barrier. Further analysis using RNA-seq revealed that C-HWE-CP may alleviate damage to Caco-2 cells through pentose and glucuronate interconversion pathways. These findings provide a theoretical basis for the role of HWE-CP functional group derivatives of HWE-CP in preventing chronic diseases associated with the intestinal barrier and facilitating the development of related functional foods.
Triple-negative breast cancer (TNBC) presents a significant therapeutic challenge due to the absence of specific targeted treatments. In this study, we explored the therapeutic potential of xanthocillin X dimethyl ether (XanDME), a naturally occurring isocyanide isolated from the marine fungus Scedosporium apiospermum, on TNBC. To elucidate the underlying mechanism, we initially demonstrated that XanDME directly binds to hemin, the oxidized form of heme, in vitro, corroborating previous reports. This interaction led to the depletion of intracellular regulatory heme. We further established that XanDME translocates into the mitochondria, where it interacts with crucial hemoproteins, namely cytochromes. The binding of XanDME with mitochondrial cytochromes disrupts the electron transport chain (ETC), inhibits the activity of mitochondrial complexes, and inactivates mitochondrial respiration. The inhibitory activity of XanDME on mitochondrial function significantly contributes to its anti-TNBC effects, as observed both in vitro and in vivo. Our study underscores the potential of XanDME against TNBC, warranting further investigations.
A new megastigmane glycoside, conspurcoside A (1), two new phenol glycosides, conspurcosides B (2) and C (3), along with twelve known compounds (4 - 15) were isolated from the bark of Mallotus conspurcatus Croizat. The structures of these compounds were identified through analysis of spectroscopic data, including 1D and 2D NMR, HRESIMS, and ECD methods. Compounds (1 -6, 14 - 15) were tested for inhibition of NO production in lipopolysaccharide (LPS)-induced RAW 264.7 cells to investigate their anti-inflammatory effects. The results revealed that compounds 2 and 3 demonstrated moderate inhibitory effects on NO production with IC50 values of 42.36 μM and 44.81 μM.
By tracing the characteristic proton and carbon nuclear magnetic resonance signals of the furan ring and aldehyde group, four novel 5‐hydroxymethylfurfural derivatives, fusaroxysporins A‐D (1‐4), together with ten known compounds were obtained from the marine fungus Fusarium oxysporum SP7. Their structures were elucidated by comprehensive spectroscopic analysis. The possible biogenic synthesis pathways of these compounds were speculated. Compound 1 showed moderate cytotoxic activity against the human type II alveolar epithelial cell A‐549 and the human hepatocarcinoma cell line HepG2 with the IC50 values of 48.0 and 92.0 μM, respectively, while the other compounds had no activity (IC50 > 200 μM).
One new gliotoxin derivative fumianthrogliotoxin (1), one new indoquizoline alkaloid N3-(methyl propionate) indoquizoline (2), and three novel indole alkaloids, anthroxyindole (3), (±)-asperfumiindole A (4), and (±)-asperfumiindole B (5), together with 16 known compounds (6–21), were isolated from the culture of deep-sea derived fungus Aspergillus fumigatus AF1. Their chemical structures and absolute configurations were determined through the analysis of NMR data in combination with electronic circular dichroism (ECD) calculations and other spectroscopic analyses. Compounds 2–11 and 13–21 were evaluated for anti-pulmonary fibrosis activity. Compounds 8 and 13 displayed significant downregulation of the mRNA expression levels of all three molecular markers (COL1A1, α-SMA and FN1), with compound 13 exhibiting the best performance among all the tested compounds.
Despite the popular belief in the anti-tumor properties of Vespa bicolor venom (VBV), there is limited scientific evidence to support this claim. This study is the first to examine the anti-tumor effects of VBV on liver cancer, both alone and in combination with cisplatin (DDP), through in vitro and in vivo experiments. In vitro experiments evaluated VBV and its combination with DDP on HepG2 cell proliferation, invasion, migration, and apoptosis. Animal studies examined the tumor-suppressive effects, safety (hepatotoxicity and nephrotoxicity), and immune impact of these treatments in tumor-bearing mice. VBV monotherapy significantly inhibited the growth of HepG2 cells by suppressing their proliferation and invasion and induced apoptosis in vitro. Notably, low VBV concentrations significantly promoted the proliferation of normal liver cells (L-02), suggesting a hepatoprotective effect. In vivo, VBV monotherapy enhanced immune function and exhibited tumor suppression comparable to DDP monotherapy but did not induce significant liver or kidney damage. In addition, VBV combined with DDP synergistically enhanced the anti-tumor effects of DDP, compensating for its limited apoptosis-inducing activity and insufficient enhancement of immune function. Initial studies have shown the strong potential of VBV as an anti-liver-tumor drug, highlighting its unique clinical value.
ETHNOPHARMACOLOGICAL RELEVANCE:The anti-tumor related diseases of Coptidis Rhizoma (Huanglian) were correlated with its traditional use of removing damp-heat, clearing internal fire, and counteracting toxicity. In the recent years, Coptidis Rhizoma and its components have drawn extensive attention toward their anti-tumor related diseases. Besides, Coptidis Rhizoma is traditionally used as an anti-inflammatory herb. Epiberberine (EPI) is a significant alkaloid isolated from Coptidis Rhizoma, and exhibits multiple pharmacological activities including anti-inflammatory. However, the effect of epiberberine on breast cancer and the inflammatory factors of metastatic breast cancer-induced osteolysis has not been demonstrated clearly.AIM OF THE STUDY:Bone metastatic breast cancer can lead to osteolysis via inflammatory factors-induced osteoclast differentiation and function. In this study, we try to analyze the effect of epiberberine on breast cancer and the inflammatory factors of metastatic breast cancer-induced osteolysis.METHODS:To evaluate whether epiberberine could suppress bone metastatic breast cancer-induced osteolytic damage, healthy female Balb/c mice were intratibially injected with murine triple-negative breast cancer 4T1 cells. Then, we examined the inhibitory effect and underlying mechanism of epiberberine on breast cancer-induced osteoclastogenesis in vitro. Xenograft assay was used to study the effect of epiberberine on breast cancer cells in vivo. Moreover, we also studied the inhibitory effects and underlying mechanisms of epiberberine on RANKL-induced osteoclast differentiation and function in vitro.RESULTS:The results show that epiberberine displayed potential therapeutic effects on breast cancer-induced osteolytic damage. Besides, our results show that epiberberine inhibited breast cancer cells-induced osteoclast differentiation and function by inhibiting secreted inflammatory cytokines such as IL-8. Importantly, we found that epiberberine directly inhibited RANKL-induced differentiation and function of osteoclast without cytotoxicity. Mechanistically, epiberberine inhibited RANKL-induced osteoclastogensis via Akt/c-Fos signaling pathway. Furthermore, epiberberine combined with docetaxel effectively protected against bone loss induced by metastatic breast cancer cells.CONCLUSIONS:Our findings suggested that epiberberine may be a promising natural compound for treating bone metastatic breast cancer-induced osteolytic damage by inhibiting IL-8 and is worthy of further exploration in preclinical and clinical trials.
OBJECTIVE:Colorectal cancer (CRC), a prevalent malignancy worldwide, has prompted extensive research into anticancer drugs. Traditional Chinese medicinal materials offer promising avenues for cancer management due to their diverse pharmacological activities. This study investigated the effects of Notopterygium incisum, a traditional Chinese medicine named Qianghuo (QH), on CRC cells and the underlying mechanism. METHODS:The sulforhodamine B assay and colony formation assay were employed to assess the effect of QH extract on the proliferation of CRC cell lines HCT116 and Caco-2. Propidium iodide (PI) staining was utilized to detect cell cycle progression, and PE Annexin V staining to detect apoptosis. Western blotting was conducted to examine the levels of apoptotic proteins, including B-cell lymphoma 2-interacting mediator of cell death (BIM), B-cell lymphoma 2 (Bcl-2), Bcl-2-associated X protein (BAX) and cleaved caspase-3, as well as BIM stability after treatment with the protein synthesis inhibitor cycloheximide. The expression of BAX was suppressed using lentivirus-mediated shRNA to validate the involvement of the BIM/BAX axis in QH-induced apoptosis. The in vivo effects of QH extract on tumor growth were observed using a xenograft model. Lastly, APCMin+ mice were used to study the effects of QH extract on primary intestinal tumors. RESULTS:QH extract exhibited significant in vitro anti-CRC activities evidenced by the inhibition of cell proliferation, perturbation of cell cycle progression, and induction of apoptosis. Mechanistically, QH extract significantly increased the stability of BIM proteins, which undergo rapid degradation under unstressed conditions. Knockdown of BAX, the downstream effector of BIM, significantly rescued QH-induced apoptosis. Furthermore, the in vitro effect of QH extract was recapitulated in vivo. QH extract significantly inhibited the tumor growth of HCT116 xenografts in nude mice and decreased the number of intestinal polyps in the APCMin+ mice. CONCLUSION:QH extract promotes the apoptosis of CRC cells by preventing the degradation of BIM.
Terpenoids are a vast group of natural products known for their remarkable biological properties and structural diversity. UbiA terpene synthases are increasingly recognized for producing various terpenoids. In this study, we identified a biosynthetic gene cluster (bgt) encoding a UbiA terpene synthase BgtA in the genome of the marine-derived fungus Trichoderma erinaceum F1-1. The gene bgtA was validated to encode the biosynthesis of (-)-α-trans-bergamotene (1). Heterologous expression of the bgt gene cluster in the characterized host Aspergillus nidulans LO8030 activated the biosynthetic pathway, leading to the isolation of eight previously undocumented bergamotene-derived sesquiterpenoids (2-9). Their structures, including the absolute configurations, were elucidated by a combination of spectroscopic analysis, ECD spectra, chemical hydrolysis, single-crystal X-ray diffraction, and biosynthetic considerations. We further demonstrated that the production of these structurally intricate sesquiterpenoids in heterologous expression is attributable to the concerted action of the UbiA terpene synthase BgtA, the cytochrome P450 BgtC, and endogenous enzymes. This study underscores the immense biosynthetic potential of fungal UbiA terpene synthase gene clusters and shows genome mining is a promising strategy for the discovery of novel terpenoids from fungi.
Sulfur-containing natural products possess a variety of biological functions including antitumor, antibacterial, anti-inflammatory and antiviral activities. In this study, four previously undescribed sulfur-containing compounds asperteretals L and M, terreins A and B, together with 17 known compounds were obtained from a culture of marine fungus A. terreus supplemented with inorganic sulfur source Na2SO4. Their planar structures and absolute configurations were elucidated by NMR, HRESIMS, and ECD experiments. The in vitro cytotoxicities of compounds 1-21 against HCT-116 and Caco-2 were evaluated by SRB assay. Asperteretal M (2) exhibited activity against HCT-116 with the IC50 value at 30μM. The antiproliferative effect of asperteretal M was confirmed by colony formation assay and cell death staining. Furthermore, the preliminary study on the anti-colon cancer mechanism of asperteretal M was performed by RNA-seq analysis. Western blotting validated that asperteretal M significantly decreased the expression of cell-cycle regulatory proteins CDK1, CDK4, and PCNA in a concentration-dependent manner.
Seven undescribed compounds, colletotrichindoles A-E, colletotrichaniline A, and colletotrichdiol A, as well as three known compounds, (-)-isoalternatine A, (+)-alternatine A and 3-hydroxybutan-2-yl 2-phenylacetate were isolated from the marine-derived fungus Colletotrichu gloeosporioides BB4. The racemic mixtures colleto-trichindole A,colletotrichindole C, and colletotrichdiol A were further separated by chiral chromatography to give three pairs of enantiomers (10S,11R,13S)/(10R,11S,13R)-colletotrichindole A, (10R,11R,13S)/ (10S,11S,13R)-colletotrichindole C, and (9S,10S)/(9R,10R)-colletotrichdiol A, respectively. The chemical structures of seven undescribed compounds and the known compounds, (-)-isoalternatine A, and (+)-alternatine A were determined using a combination of NMR, MS, X-ray diffraction, ECD calculations, and/or chemical synthesis. All possible enantiomers of colletotrichindoles A-E were synthesized and used to determine the ab-solute configurations of the natural products by comparing their spectroscopic data and HPLC retention times on a chiral column. In addition, the X-ray crystal structures of the known compounds (-)-isoalternatine A and (+)-alternatine A were also obtained to confirm their absolute configurations. (10S,11R,13S)-Colletotrichindole A, colletotrichindole B, and (+)-alternatine A significantly reduced triglyceride levels in 3T3-L1 cells with EC50 values of 5.8, 9.0, and 1.3 & mu;M, respectively.
Name reactions are the cornerstone of organic chemistry and constitute a vital component of organic chemistry experiments in universities.This article provides a concise overview of organic name reactions,including those named after Chinese chemists.The focus is primarily on the current status of name reactions in university organic chemistry experiments,exploring their teaching characteristics,advantages,and future trends.This article serves as a reference for domestic colleagues engaged in experimental teaching research,as well as for expanding new methods and technologies in experiments.Furthermore,it aims to enhance students'interest in learning and foster a sense of national pride.