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1.
Carbohydr Polym ; 339: 122266, 2024 Sep 01.
Article in English | MEDLINE | ID: mdl-38823930

ABSTRACT

Konjac glucomannan (KG) is a dietary fiber hydrocolloid derived from Amorphophallus konjac tubers and is widely utilized as a food additive and dietary supplement. As a health-conscious choice, purified KG, along with konjac flour and KG-infused diets, have gained widespread acceptance in Asian and European markets. An overview of the chemical composition and structure of KG is given in this review, along with thorough explanations of the processes used in its extraction, production, and purification. KG has been shown to promote health by reducing glucose, cholesterol, triglyceride levels, and blood pressure, thereby offering significant weight loss advantages. Furthermore, this review delves into the extensive health benefits and pharmaceutical applications of KG and its derivatives, emphasizing its prebiotic, anti-inflammatory, and antitumor activities. This study highlights how these natural polysaccharides can positively influence health, underscoring their potential in various biomedical applications.


Subject(s)
Amorphophallus , Mannans , Mannans/chemistry , Mannans/isolation & purification , Humans , Amorphophallus/chemistry , Animals , Dietary Fiber/analysis , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/pharmacology , Anti-Inflammatory Agents/isolation & purification , Dietary Supplements , Prebiotics , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Antineoplastic Agents/pharmacology
2.
Carbohydr Polym ; 341: 122360, 2024 Oct 01.
Article in English | MEDLINE | ID: mdl-38876721

ABSTRACT

Kangiella japonica KMM 3899T is a Gram-negative bacterium isolated from a sandy sediment sample collected from the Sea of Japan. Here the results of the structure and the biological activity against breast cancer cells of the cell-wall polysaccharide from K. japonica KMM 3899T have been described. The structure of the repeating unit of the polysaccharide was elucidated using chemical analysis and NMR spectroscopy: →4)-α-L-GalpNAc3AcA-(1 â†’ 3)-α-D-GlcpNAc-(1 â†’ 4)-ß-D-GlcpNAc3NAcAN-(1→. The cell-wall polysaccharide had an antiproliferative effect against T-47D cells. Flow cytometric and Western blot analysis revealed that the polysaccharide induced S phase arrest and mitochondrial-dependent apoptosis.


Subject(s)
Antineoplastic Agents , Apoptosis , Breast Neoplasms , Cell Proliferation , Cell Wall , Humans , Cell Proliferation/drug effects , Breast Neoplasms/drug therapy , Breast Neoplasms/pathology , Cell Wall/chemistry , Cell Wall/drug effects , Apoptosis/drug effects , Antineoplastic Agents/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Cell Line, Tumor , Female , Polysaccharides, Bacterial/pharmacology , Polysaccharides, Bacterial/chemistry , Polysaccharides, Bacterial/isolation & purification , Carbohydrate Sequence , Polysaccharides/pharmacology , Polysaccharides/chemistry , Polysaccharides/isolation & purification
3.
Org Lett ; 26(19): 4127-4131, 2024 May 17.
Article in English | MEDLINE | ID: mdl-38718303

ABSTRACT

Hybrid genome-mining/15N-NMR was used to target compounds containing piperazate (Piz) residues, leading to the discovery of caveamides A (1) and B (2) from Streptomyces sp. strain BE230, isolated from New Rankin Cave (Missouri). Caveamides are highly dynamic molecules containing an unprecedented ß-ketoamide polyketide fragment, two Piz residues, and a new N-methyl-cyclohexenylalanine residue. Caveamide B (2) exhibited nanomolar cytotoxicity against several cancer cell lines and nanomolar antimicrobial activity against MRSA and E. coli.


Subject(s)
Escherichia coli , Methicillin-Resistant Staphylococcus aureus , Streptomyces , Humans , Molecular Structure , Streptomyces/chemistry , Escherichia coli/drug effects , Methicillin-Resistant Staphylococcus aureus/drug effects , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/isolation & purification , Microbial Sensitivity Tests , Antineoplastic Agents/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Alanine/chemistry , Alanine/pharmacology , Alanine/analogs & derivatives , Drug Screening Assays, Antitumor , Peptides/chemistry , Peptides/pharmacology , Peptides/isolation & purification , Cell Line, Tumor , Pyridazines
4.
Mar Drugs ; 22(5)2024 May 14.
Article in English | MEDLINE | ID: mdl-38786609

ABSTRACT

Two new cytochalasin derivatives, peniotrinins A (1) and B (2), three new citrinin derivatives, peniotrinins C-E (4, 5, 7), and one new tetramic acid derivative, peniotrinin F (12), along with nine structurally related known compounds, were isolated from the solid culture of Peniophora sp. SCSIO41203. Their structures, including the absolute configurations of their stereogenic carbons, were fully elucidated based on spectroscopic analysis, quantum chemical calculations, and the calculated ECD. Interestingly, 1 is the first example of a rare 6/5/5/5/6/13 hexacyclic cytochalasin. We screened the above compounds for their anti-prostate cancer activity and found that compound 3 had a significant anti-prostate cancer cell proliferation effect, while compounds 1 and 2 showed weak activity at 10 µM. We then confirmed that compound 3 exerts its anti-prostate cancer effect by inducing methuosis through transmission electron microscopy and cellular immunostaining, which suggested that compound 3 might be first reported as a potential anti-prostate methuosis inducer.


Subject(s)
Antineoplastic Agents , Prostatic Neoplasms , Humans , Antineoplastic Agents/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Male , PC-3 Cells , Prostatic Neoplasms/drug therapy , Prostatic Neoplasms/pathology , Cell Proliferation/drug effects , Cytochalasins/pharmacology , Cytochalasins/chemistry , Cytochalasins/isolation & purification , Aquatic Organisms , Cell Line, Tumor , Molecular Structure
5.
Mar Drugs ; 22(5)2024 May 14.
Article in English | MEDLINE | ID: mdl-38786610

ABSTRACT

Octocoral of the genus Clavularia is a kind of marine invertebrate possessing abundant cytotoxic secondary metabolites, such as prostanoids and dolabellanes. In our continuous natural product study of C. spp., two previously undescribed prostanoids [clavulone I-15-one (1) and 12-O-deacetylclavulone I (2)] and eleven known analogs (3-13) were identified. The structures of these new compounds were elucidated based on analysis of their 1D and 2D NMR, HRESIMS, and IR data. Additionally, all tested prostanoids (1 and 3-13) showed potent cytotoxic activities against the human oral cancer cell line (Ca9-22). The major compound 3 showed cytotoxic activity against the Ca9-22 cells with the IC50 value of 2.11 ± 0.03 µg/mL, which echoes the cytotoxic effect of the coral extract. In addition, in silico tools were used to predict the possible effects of isolated compounds on human tumor cell lines and nitric oxide production, as well as the pharmacological potentials.


Subject(s)
Anthozoa , Antineoplastic Agents , Prostaglandins , Humans , Anthozoa/chemistry , Animals , Cell Line, Tumor , Prostaglandins/pharmacology , Antineoplastic Agents/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Nitric Oxide/metabolism , Inhibitory Concentration 50 , Aquatic Organisms , Molecular Structure
6.
Mar Drugs ; 22(5)2024 May 20.
Article in English | MEDLINE | ID: mdl-38786622

ABSTRACT

Five new sulfated arylpyrrole and arylpyrrolone alkaloids, denigrins H-L (1-5), along with two known compounds, dictyodendrin B and denigrin G, were isolated from an extract of a New Zealand Dictyodendrilla c.f. dendyi marine sponge. Denigrins H-L represent the first examples of sulfated denigrins, with denigrins H and I (1-2), as derivatives of denigrin D, containing a pyrrolone core, and denigrins J-L (3-5), as derivatives of denigrin E (6), containing a pyrrole core. Their structures were elucidated by interpretation of 1D and 2D NMR spectroscopic data, ESI, and HR-ESI-MS spectrometric data, as well as comparison with literature data. Compounds 1-5, along with six known compounds previously isolated from the same extract, showed minimal cytotoxicity against the HeLa cervical cancer cell line.


Subject(s)
Alkaloids , Porifera , Pyrroles , Animals , Porifera/chemistry , Humans , New Zealand , Pyrroles/pharmacology , Pyrroles/chemistry , Pyrroles/isolation & purification , HeLa Cells , Alkaloids/pharmacology , Alkaloids/chemistry , Alkaloids/isolation & purification , Sulfates/chemistry , Sulfates/pharmacology , Molecular Structure , Magnetic Resonance Spectroscopy , Antineoplastic Agents/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification
7.
Phytochemistry ; 223: 114113, 2024 Jul.
Article in English | MEDLINE | ID: mdl-38697241

ABSTRACT

Eleven undescribed cembrane-type diterpenoids, named litoamentenes A-K (1-11), were isolated from the soft coral Litophyton amentaceum collected from the South China Sea. Their structures were elucidated by extensive analysis of spectroscopic data, comparison with the literature data, single crystal X-ray diffraction, quantum chemical calculations and TDDFT-ECD calculations. This is the first systematic investigation of L. amentaceum. In particular, compounds 1-3 are cembrane-type norditerpenoids that lack isopropyl side chains. Compound 6 is a cembrane-type norditerpenoid without a methyl group at C-4, the first natural product identified with this carbon skeleton. Compounds 6, 9 and 10 showed modest cytotoxicity against several human cancer cell lines with IC50 values ranging from 3.99 to 14.56 µM.


Subject(s)
Anthozoa , Diterpenes , Drug Screening Assays, Antitumor , Anthozoa/chemistry , Diterpenes/chemistry , Diterpenes/pharmacology , Diterpenes/isolation & purification , Animals , Humans , Molecular Structure , Structure-Activity Relationship , Antineoplastic Agents/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , China , Cell Line, Tumor , Cell Proliferation/drug effects , Dose-Response Relationship, Drug , Models, Molecular
8.
Sci Prog ; 107(2): 368504241253675, 2024.
Article in English | MEDLINE | ID: mdl-38807531

ABSTRACT

Camptothecin (CPT) is an important alkaloid used for anticancer treatment. It is mainly produced by two endangered and overharvested Camptotheca acuminata and Nothapodytes nimmoniana plants. Endophytic fungi are promising alternative sources for CPT production. In the present study, fungi residing within explants of Ixora chinensis were isolated and their CPT-producing capability of their endophytes was verified via thin-layer chromatography, high-performance liquid chromatography, liquid chromatography/high resolution mass spectrometry, and nuclear magnetic resonance analyses and compared with standards. In addition, MTT and sulforhodamine B assays were selected to test the anticancer effect. The endophytic fungi collection of 62 isolates were assigned to 11 genera, with four common genera (Diaporthe, Phyllosticta, Colletotrichum, and Phomopsis) and seven less common genera (Penicillium, Botryosphaeria, Fusarium, Pestalotiopsis, Aspergillus, and Didymella). Moreover, the anticancer activity of extracts was assessed against human lung carcinoma (A549). Among eight potential extracts, only Penicillium sp. I3R2 was found to be a source of CPT, while the remaining seven extracts have not been discovered potential secondary compounds. Thus, other prominent endophytic fungi might be potential candidates of phytochemicals with anticancer properties.


Subject(s)
Antineoplastic Agents , Camptothecin , Endophytes , Fungi , Humans , Camptothecin/pharmacology , Camptothecin/chemistry , Camptothecin/biosynthesis , Endophytes/metabolism , Endophytes/isolation & purification , Endophytes/chemistry , Fungi/isolation & purification , Antineoplastic Agents/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , A549 Cells , Cell Line, Tumor
9.
Molecules ; 29(9)2024 Apr 29.
Article in English | MEDLINE | ID: mdl-38731537

ABSTRACT

The fungal genus Trichoderma is a rich source of structurally diverse secondary metabolites with remarkable pharmaceutical properties. The chemical constituents and anticancer activities of the marine-derived fungus Trichoderma lixii have never been investigated. In this study, a bioactivity-guided investigation led to the isolation of eleven compounds, including trichodermamide A (1), trichodermamide B (2), aspergillazine A (3), DC1149B (4), ergosterol peroxide (5), cerebrosides D/C (6/7), 5-hydroxy-2,3-dimethyl-7-methoxychromone (8), nafuredin A (9), and harzianumols E/F (10/11). Their structures were identified by using various spectroscopic techniques and compared to those in the literature. Notably, compounds 2 and 5-11 were reported for the first time from this species. Evaluation of the anticancer activities of all isolated compounds was carried out. Compounds 2, 4, and 9 were the most active antiproliferative compounds against three cancer cell lines (human myeloma KMS-11, colorectal HT-29, and pancreas PANC-1). Intriguingly, compound 4 exhibited anti-austerity activity with an IC50 of 22.43 µM against PANC-1 cancer cells under glucose starvation conditions, while compound 2 did not.


Subject(s)
Antineoplastic Agents , Trichoderma , Antineoplastic Agents/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Humans , Trichoderma/chemistry , Cell Line, Tumor , Cell Proliferation/drug effects , Molecular Structure , Aquatic Organisms/chemistry , Drug Screening Assays, Antitumor
10.
Phytochemistry ; 223: 114119, 2024 Jul.
Article in English | MEDLINE | ID: mdl-38705266

ABSTRACT

Six previously undescribed prenylated indole diketopiperazine alkaloids, talaromyines A-F (1-6), were isolated from the marine-derived fungus Talaromyces purpureogenus SCSIO 41517. Their structures including absolute configurations were elucidated on the basis of comprehensive spectroscopic data including NMR, HR-ESI-MS, and electronic circular dichroism calculations, together with chemical analysis of hydrolysates. Compounds 1-5 represent the first example of spirocyclic indole diketopiperazines biosynthesized from the condensation of L-tryptophan and L-alanine. Compounds 2 and 4-5 showed selective inhibitory activities against phosphatases TCPTP and MEG2 with IC50 value of 17.9-29.7 µM, respectively. Compounds 4-5 exhibited mild cytotoxic activities against two human cancer cell lines H1975 and HepG-2.


Subject(s)
Diketopiperazines , Talaromyces , Talaromyces/chemistry , Diketopiperazines/chemistry , Diketopiperazines/pharmacology , Diketopiperazines/isolation & purification , Humans , Molecular Structure , Prenylation , Drug Screening Assays, Antitumor , Structure-Activity Relationship , Antineoplastic Agents/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Indole Alkaloids/isolation & purification , Indole Alkaloids/chemistry , Indole Alkaloids/pharmacology , Alkaloids/chemistry , Alkaloids/pharmacology , Alkaloids/isolation & purification , Dose-Response Relationship, Drug , Enzyme Inhibitors/pharmacology , Enzyme Inhibitors/chemistry , Enzyme Inhibitors/isolation & purification , Hep G2 Cells , Cell Proliferation/drug effects , Phosphoric Monoester Hydrolases/antagonists & inhibitors , Phosphoric Monoester Hydrolases/metabolism , Cell Line, Tumor
11.
Fitoterapia ; 176: 106025, 2024 Jul.
Article in English | MEDLINE | ID: mdl-38768797

ABSTRACT

Algae and its metabolites have been a popular subject of research in numerous fields over the years. Various reviews have been written on algal bioactive components, but a specific focus on Antarctic-derived algae is seldom reviewed. Due to the extreme climate conditions of Antarctica, it is hypothesized that the acclimatized algae may have given rise to a new set of bioactive compounds as a result of adaptation. Although most studies done on Antarctic algae are based on ecological and physiological studies, as well as in the field of nanomaterial synthesis, some studies point out the potential therapeutic properties of these compounds. As an effort to shed light on a different application of Antarctic algae, this review focuses on evaluating its different medicinal properties, including antimicrobial, anticancer, antioxidative, anti-inflammatory, and skin protective effects.


Subject(s)
Antioxidants , Antarctic Regions , Antioxidants/pharmacology , Antioxidants/isolation & purification , Anti-Inflammatory Agents/pharmacology , Anti-Inflammatory Agents/isolation & purification , Humans , Anti-Infective Agents/pharmacology , Anti-Infective Agents/isolation & purification , Antineoplastic Agents/pharmacology , Antineoplastic Agents/isolation & purification , Biological Products/pharmacology , Biological Products/isolation & purification , Molecular Structure
12.
Int J Biol Macromol ; 272(Pt 1): 132543, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38788870

ABSTRACT

Some macrofungi have a long history of being used as traditional or folk medicines, making significant contributions to human health. To discover bioactive molecules with potential anticancer properties, a homogeneous heteropolysaccharide (FOBP90-1) was purified from the medicinal macrofungus Fomitopsis officinalis. FOBP90-1 was found to have a molecular weight of 2.87 × 104 g/mol and mainly consist of →6)-α-d-Galp-(1→, →2,6)-α-d-Galp-(1→, →3)-α-l-Fucp-(1→, →6)-ß-d-Glcp-(1→, α-d-Manp-(1→, and 3-O-Me-α-l-Fucp-(1→ according to UV, FT-IR, methylation analysis, and NMR data. In addition to its structural properties, FOBP90-1 displayed anticancer activity in zebrafish models. The following mechanistic analysis discovered that the in vivo antitumor effect was linked to immune activation and angiogenesis inhibition. These effects were mediated by the interactions of FOBP90-1 with TLR-2, TLR-4, PD-L1, and VEGFR-2, as determined through a series of experiments involving cells, transgenic zebrafish, molecular docking simulations, and surface plasmon resonance (SPR). All the experimental findings have demonstrated that FOBP90-1, a purified fungal polysaccharide, is expected to be utilized as a cancer treatment agent.


Subject(s)
Antineoplastic Agents , Coriolaceae , Fungal Polysaccharides , Zebrafish , Animals , Fungal Polysaccharides/chemistry , Fungal Polysaccharides/pharmacology , Fungal Polysaccharides/isolation & purification , Humans , Coriolaceae/chemistry , Antineoplastic Agents/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Cell Line, Tumor , Neoplasms/drug therapy , Vascular Endothelial Growth Factor Receptor-2/metabolism , Vascular Endothelial Growth Factor Receptor-2/antagonists & inhibitors , Molecular Docking Simulation
13.
J Sep Sci ; 47(9-10): e2300898, 2024 May.
Article in English | MEDLINE | ID: mdl-38726747

ABSTRACT

Based on the specific binding of drug molecules to cell membrane receptors, a screening and separation method for active compounds of natural products was established by combining phospholipase C (PLC) sensitized hollow fiber microscreening by a solvent seal with high-performance liquid chromatography technology. In the process, the factors affecting the screening were optimized. Under the optimal screening conditions, we screened honokiol (HK), magnolol (MG), negative control drug carbamazepine, and positive control drug amentoflavone, the repeatability of the method was tested. The PLC activity was determined before and after the screening. Experimental results showed that the sensitization factors of PLC of HK and MG were 61.0 and 48.5, respectively, and amentoflavone was 15.0, carbamazepine could not bind to PLC. Moreover, the molecular docking results were consistent with this measurement, indicating that HK and MG could be combined with PLC, and they were potential interacting components with PLC. This method used organic solvent to seal the PLC greatly ensuring the activity, so this method had the advantage of integrating separation, and purification with screening, it not only exhibited good reproducibility and high sensitivity but was also suitable for screening the active components in natural products by various targets in vitro.


Subject(s)
Biological Products , Type C Phospholipases , Biological Products/chemistry , Biological Products/pharmacology , Biological Products/isolation & purification , Type C Phospholipases/metabolism , Type C Phospholipases/chemistry , Type C Phospholipases/antagonists & inhibitors , Chromatography, High Pressure Liquid , Molecular Docking Simulation , Lignans/chemistry , Lignans/isolation & purification , Lignans/pharmacology , Biphenyl Compounds/antagonists & inhibitors , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Antineoplastic Agents/isolation & purification , Humans , Allyl Compounds , Phenols
14.
J Oleo Sci ; 73(5): 743-749, 2024.
Article in English | MEDLINE | ID: mdl-38692896

ABSTRACT

Conjugated fatty acids have anticancer effects. Therefore, the establishment of a synthetic method for conjugated fatty acids is important for overcoming cancer. Here, we attempted to synthesize conjugated fatty acids using enzymes extracted from seaweeds containing these fatty acids. Lipids from 12 species of seaweeds from the seas around Japan were analyzed, and Padina arborescens Holmes was found to contain conjugated fatty acids. Then, we synthesized parinaric acid, a conjugated tetraenoic acid, from α-linolenic acid using the enzyme of P. arborescens. This method is expected to have a variety of potential applications for overcoming cancer.


Subject(s)
alpha-Linolenic Acid , alpha-Linolenic Acid/chemistry , Seaweed/chemistry , Fatty Acids, Unsaturated/chemistry , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Antineoplastic Agents/pharmacology
15.
Carbohydr Polym ; 337: 122171, 2024 Aug 01.
Article in English | MEDLINE | ID: mdl-38710561

ABSTRACT

Commercially available mushroom polysaccharides have found widespread use as adjuvant tumor treatments. However, the bioactivity of polysaccharides in Lactarius hatsudake Tanaka (L. hatsudake), a mushroom with both edible and medicinal uses, remains relatively unexplored. To address this gap, five L. hatsudake polysaccharides with varying molecular weights were isolated, named LHP-1 (898 kDa), LHP-2 (677 kDa), LHP-3 (385 kDa), LHP-4 (20 kDa), and LHP-5 (4.9 kDa). Gas chromatography-mass spectrometry, nuclear magnetic resonance, and atomic force microscopy, etc., were employed to determine their structural characteristics. The results confirmed that spherical aggregates with amorphous flexible fiber chains dominated the conformation of the LHP. LHP-1 and LHP-2 were identified as glucans with α-(1,4)-Glcp as the main chain; LHP-3 and LHP-4 were classified as galactans with varying molecular weights but with α-(1,6)-Galp as the main chain; LHP-5 was a glucan with ß-(1,3)-Glcp as the main chain and ß-(1,6)-Glcp connecting to the side chains. Significant differences were observed in inhibiting tumor cell cytotoxicity and the antioxidant activity of the LHPs, with LHP-5 and LHP-4 identified as the principal bioactive components. These findings provide a theoretical foundation for the valuable use of L. hatsudake and emphasize the potential application of LHPs in therapeutic tumor treatments.


Subject(s)
Antioxidants , Glucans , Glucans/chemistry , Glucans/pharmacology , Glucans/isolation & purification , Humans , Antioxidants/chemistry , Antioxidants/pharmacology , Antioxidants/isolation & purification , Agaricales/chemistry , Polysaccharides/chemistry , Polysaccharides/pharmacology , Polysaccharides/isolation & purification , Molecular Weight , Antineoplastic Agents/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Cell Line, Tumor , Fungal Polysaccharides/chemistry , Fungal Polysaccharides/pharmacology , Fungal Polysaccharides/isolation & purification , Basidiomycota/chemistry , Cell Survival/drug effects
16.
Photochem Photobiol Sci ; 23(5): 1011-1029, 2024 May.
Article in English | MEDLINE | ID: mdl-38753286

ABSTRACT

Photodynamic therapy (PDT) stands out as a noteworthy development as an alternative targeted treatment against skin ailments. While PDT has advanced significantly, research into photo-activatable "Green drugs" derived from plants which are less toxic than the synthetic drugs has not kept pace. This study investigates the potential of Fagopyrin F Containing Fraction (FCF) derived from Fagopyrum tataricum in mediating PDT against Staphylococcus aureus and skin cancer cells (A431). FCF was isolated from the plant extract using thin-layer chromatography, followed by identification of the compound through high-performance liquid chromatography and high-resolution liquid chromatography-mass spectrometry. FCF was tested to determine its antibacterial and anticancer efficacy. Results revealed that FCF-mediated PDT exhibited potent action against S. aureus, significantly reducing bacterial viability (MIC 19.5 µg/100 µL). Moreover, FCF-mediated PDT showed good efficacy against A431 cells, resulting in a notable reduction in cell viability (IC50 29.08 µg/mL). Given the known association between S. aureus and squamous cell carcinoma (SCC), FCF shows the potential to effectively target and eradicate both SCC and the related S. aureus present within the lesions. In silico study reveals that Fagopyrin F effectively binds with the epidermal growth factor (EGFR), one among the highly expressed proteins in the A431 cells, with a binding energy of - 9.6 kcal/mol. The affinity of Fagopyrin F for EGFR on A431 cancer cells along with its cytotoxicity against skin cancer cells while safeguarding the normal cells (L929) plays a major part in the way it targets cancer cells. However, its safety, efficacy, and long-term advantages in treating skin conditions require more investigation, including in vivo investigations and clinical trials.


Subject(s)
Anti-Bacterial Agents , Carcinoma, Squamous Cell , Cell Survival , Fagopyrum , Photochemotherapy , Photosensitizing Agents , Staphylococcus aureus , Humans , Staphylococcus aureus/drug effects , Carcinoma, Squamous Cell/drug therapy , Carcinoma, Squamous Cell/pathology , Carcinoma, Squamous Cell/metabolism , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/isolation & purification , Fagopyrum/chemistry , Cell Survival/drug effects , Photosensitizing Agents/pharmacology , Photosensitizing Agents/chemistry , Photosensitizing Agents/isolation & purification , Microbial Sensitivity Tests , Cell Line, Tumor , Plant Extracts/pharmacology , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Drug Screening Assays, Antitumor , Skin Neoplasms/drug therapy , Skin Neoplasms/pathology , Skin Neoplasms/metabolism , Molecular Docking Simulation , Antineoplastic Agents/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification
17.
J Asian Nat Prod Res ; 26(7): 850-857, 2024 Jul.
Article in English | MEDLINE | ID: mdl-38572975

ABSTRACT

Hericium erinaceus is a species of mushroom with high nutritional value that is used mainly as food in tropical countries. Phytochemical study of H. erinaceus led to the isolation of an undescribed compound, named as hericium VN (1), together with nine known compounds, 1-(2-formyl-1-pyrrolyl)butanoic acid (2), herierin III (3), 5'-(methylthio)adenosine (4), adenosine (5), nicotinic acid (6), (22E,24R)-5α,8α-epidioxyergosta-6,9(11),22-trien-3ß-ol (7), 5α,8α-peroxycerevisterol (8), (22E,24R)-5α,8α-epidioxy-egosta-6,22-diene 3-O-ß-D-glucopyranoside (9), and cerevisterol (10) based on extensive analyses of HR-ESI-MS, 1D and 2D NMR spectra. The absolute configuration of compound 1 was determined by experimental combined with calculated electronic circular dichroism spectra. Compound 7 exhibited cytotoxic effects against brain tumor cell line CCF-STTG1 with the IC50 value of 15.50 µM, compared to that of the positive control compound, doxorubicin, which showed IC50 value of 15.84 µM.


Subject(s)
Astrocytoma , Drug Screening Assays, Antitumor , Hericium , Humans , Molecular Structure , Astrocytoma/drug therapy , Hericium/chemistry , Brain Neoplasms/drug therapy , Antineoplastic Agents/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Cell Line, Tumor , Nuclear Magnetic Resonance, Biomolecular
18.
Phytochemistry ; 222: 114103, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38636686

ABSTRACT

Eight new cytochalasans rosellichalasins A-H (1-8), as well as two new shunt metabolites rosellinins A (9) and B (10) before intramolecular Diels-Alder cycloaddition reaction in cytochalasan biosynthesis, along with nine known cytochalsans (11-19) were isolated from the endophytic fungus Rosellinia sp. Glinf021, which was derived from the medicinal plant Glycyrrhiza inflata. Their structures were characterized by extensive analysis of 1D and 2D NMR as well as HRESIMS spectra and quantum chemical ECD calculations. The cytotoxic activities of these compounds were evaluated against four human cancer cell lines including HCT116, MDA-MB-231, BGC823, and PANC-1 with IC50 values ranging from 0.5 to 58.2 µM.


Subject(s)
Antineoplastic Agents , Cytochalasins , Drug Screening Assays, Antitumor , Xylariales , Humans , Antineoplastic Agents/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Cell Line, Tumor , Cell Proliferation/drug effects , Cytochalasins/chemistry , Cytochalasins/pharmacology , Cytochalasins/isolation & purification , Dose-Response Relationship, Drug , Endophytes/chemistry , Molecular Structure , Structure-Activity Relationship , Xylariales/chemistry , Xylariales/classification
19.
Phytochemistry ; 223: 114097, 2024 Jul.
Article in English | MEDLINE | ID: mdl-38641142

ABSTRACT

A chemical investigation of the dichloromethane extract from the Xisha sponge Diacarnus sp. revealed seven undescribed norterpene cyclic peroxides, named diacarperoxides T-Z, and five unreported related norterpenes, named diacarnoids E-I, and eleven previously reported compounds. The structures of these isolated compounds, including their absolute configurations, were elucidated based on extensive spectroscopic analyses, electronic circular dichroism (ECD) calculations, Snatzke's method, [Rh2(OCOCF3)4]-induced ECD spectra, and modified Mosher's method. Bioassays were performed to assess the antibacterial activity against six pathogenic bacteria, cytotoxicities toward three cancer cell lines, and antimalarial activity against Plasmodium parasites. Most of the cyclic peroxides exhibited substantial antibacterial activity (MIC 1-8 µg/mL). Diacarperoxide W and nuapapuin A showed substantial antimalarial activity with IC50 values of 0.98 and 2.83 µM. Moreover, many compounds exhibited <50% cell survival rates, and IC50 values of 0.22-6.33 µM. The apoptosis assay showed that nuapapuin A induced cancer cell apoptosis in a dose-dependent manner.


Subject(s)
Anti-Bacterial Agents , Antimalarials , Peroxides , Porifera , Antimalarials/pharmacology , Antimalarials/chemistry , Antimalarials/isolation & purification , Porifera/chemistry , Peroxides/pharmacology , Peroxides/chemistry , Peroxides/isolation & purification , Humans , Animals , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/isolation & purification , Molecular Structure , Antineoplastic Agents/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Drug Screening Assays, Antitumor , Apoptosis/drug effects , Parasitic Sensitivity Tests , Plasmodium falciparum/drug effects , Structure-Activity Relationship , Microbial Sensitivity Tests , Cell Line, Tumor , Dose-Response Relationship, Drug , Cell Survival/drug effects , Cell Proliferation/drug effects
20.
Bioorg Chem ; 147: 107329, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38608410

ABSTRACT

By co-culturing two endophytic fungi (Chaetomium virescens and Xylaria grammica) collected from the medicinal and edible plant Smilax glabra Roxb. and analyzing them with MolNetEnhancer module on GNPS platform, seven undescribed chromone-derived polyketides (chaetoxylariones A-G), including three pairs of enantiomer ones (2a/2b, 4a/4b and 6a/6b) and four optical pure ones (1, 3, 5 and 7), as well as five known structural analogues (8-12), were obtained. The structures of these new compounds were characterized by NMR spectroscopy, single-crystal X-ray diffraction, 13C NMR calculation and DP4+ probability analyses, as well as the comparison of the experimental electronic circular dichroism (ECD) data. Structurally, compound 1 featured an unprecedented chromone-derived sulfonamide tailored by two isoleucine-derived δ-hydroxy-3-methylpentenoic acids via the acylamide and NO bonds, respectively; compound 2 represented the first example of enantiomeric chromone derivative bearing a unique spiro-[3.3]alkane ring system; compound 3 featured a decane alkyl side chain that formed an undescribed five-membered lactone ring between C-7' and C-10'; compound 4 contained an unexpected highly oxidized five-membered carbocyclic system featuring rare adjacent keto groups; compound 7 featured a rare methylsulfonyl moiety. In addition, compound 10 showed a significant inhibition towards SW620/AD300 cells with an IC50 value of PTX significantly decreased from 4.09 µM to 120 nM, and a further study uncovered that compound 10 could obviously reverse the MDR of SW620/AD300 cells.


Subject(s)
Antineoplastic Agents , Chaetomium , Chromones , Drug Screening Assays, Antitumor , Polyketides , Xylariales , Chromones/chemistry , Chromones/pharmacology , Chromones/isolation & purification , Polyketides/chemistry , Polyketides/pharmacology , Polyketides/isolation & purification , Molecular Structure , Xylariales/chemistry , Chaetomium/chemistry , Humans , Antineoplastic Agents/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Structure-Activity Relationship , Dose-Response Relationship, Drug , Cell Line, Tumor , Coculture Techniques , Cell Proliferation/drug effects
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