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1.
J Antibiot (Tokyo) ; 2024 May 09.
Artigo em Inglês | MEDLINE | ID: mdl-38724631

RESUMO

Three new nonenes, verrucanonenes A‒C (1‒3), were isolated from culture broth of marine-derived fungus Albifimbria verrucaria. These compounds were isolated using silica gel column chromatography, reversed-phase medium pressure liquid chromatography, Sephadex LH-20 column chromatography, and preparative HPLC. Their structures were determined using a spectroscopic method. Cytotoxicities of these isolated compounds to A549, DU145, HCT116, and HT1080 cancer cell lines were assessed. Compounds 1‒3 exhibited cytotoxicities to DU145 cancer cell line, with IC50 values of 23.4, 28.6, and 20.1 µM, respectively. Compound 2 decreased H1N1-induced cytopathic effects on MDCK cells in a dose-dependent manner.

2.
J Antibiot (Tokyo) ; 77(6): 338-344, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38519550

RESUMO

Three new phthalide derivatives (1‒3) together with two known compounds, erinaceolactone B (4) and hericerin III (5), were isolated from the culture broth of Dentipellis fragilis. The chemical structures of 1‒5 were determined by analyses of their 1D-, 2D-NMR, and MS. The absolute configuration of 1 was determined by CD analysis. The isolated compounds were assessed for their cytotoxic activities against A549, DU145, HCT116, and HT1080 cancer cell lines. Compounds 1‒5 showed strong cytotoxic activities against DU145, with IC50 values ranging from 14.3 to 16.1 µM. Additionally, all compounds showed moderate or weak cytotoxic activities against all cell lines except for compounds 4 and 1 which showed no cytotoxic activities against A549 and HCT116 cancer cell lines, respectively. Against HT1080 cancer cell line, only compound 2 displayed moderate cytotoxic activity.


Assuntos
Antineoplásicos , Benzofuranos , Humanos , Linhagem Celular Tumoral , Benzofuranos/farmacologia , Benzofuranos/química , Benzofuranos/isolamento & purificação , Antineoplásicos/farmacologia , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Concentração Inibidora 50 , Ensaios de Seleção de Medicamentos Antitumorais , Meios de Cultura
3.
Int J Mol Sci ; 24(24)2023 Dec 09.
Artigo em Inglês | MEDLINE | ID: mdl-38139137

RESUMO

Agrimonia pilosa Ledeb., an important medicinal herb in traditional East Asian medicine, is primarily used to treat abdominal pain, dysentery, and hemostasis. There are ten other reported species of Agrimonia plants, including Agrimonia coreana Nakai-a naturally growing species in South Korea-and Agrimonia eupatoria Linn. Although recent studies have isolated numerous active constituents and investigated their effects, the medicinal utility of this herb is not yet fully explored. Through patch-clamp recording, a previous study reported that Agrimonia plant extracts inhibit the function of Ca2+ release-activated Ca2+ channels (CRACs). Herein, we aimed to identify and isolate the main compounds in A. coreana responsible for CRAC inhibition while assessing the anti-inflammatory effects mediated by this inhibition. We demonstrated for the first time that alphitolic acid isolated from A. coreana has a dose-dependent inhibitory effect on CRAC activity and, thus, an inhibitory effect on intracellular calcium increase. Furthermore, analysis of human CD4+ T cell proliferation via the carboxyfluorescein diacetate succinimidyl ester method revealed that alphitolic acid inhibited T cell proliferation in a concentration-dependent manner. Our findings provide a theoretical basis for the potential therapeutic use of alphitolic acid in the treatment of inflammatory diseases.


Assuntos
Agrimonia , Humanos , Linfócitos T , Extratos Vegetais/farmacologia , Extratos Vegetais/uso terapêutico , Anti-Inflamatórios/farmacologia
4.
J Antibiot (Tokyo) ; 76(12): 731-734, 2023 12.
Artigo em Inglês | MEDLINE | ID: mdl-37845350

RESUMO

A new formanilide dimer, fraxinin (1), and three known formanilides (2‒4) were isolated from the culture broth of Perenniporia fraxinea using silica gel and Sephadex LH-20 column chromatographies, medium-pressure liquid chromatography (MPLC), and preparative HPLC. The structures of these compounds were determined by spectroscopic methods, such as NMR and mass analysis, and by comparison of the spectra with previously reported data. The free radical scavenging activities of the isolated compounds were assessed using 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals. Compounds 1‒3 exhibited ABTS radical scavenging activity with IC50 values in the range of 57.2-250.2 µM. Compounds 2 and 4 marginally reduced disease incidence of powdery mildew with a control value of 42% at 1.0 mg ml-1 in cucumber leaf disk assay.


Assuntos
Antioxidantes , Sequestradores de Radicais Livres , Sequestradores de Radicais Livres/farmacologia , Sequestradores de Radicais Livres/química , Antioxidantes/farmacologia , Antioxidantes/química , Compostos de Bifenilo/química , Picratos/química
5.
J Antibiot (Tokyo) ; 76(12): 741-745, 2023 12.
Artigo em Inglês | MEDLINE | ID: mdl-37749218

RESUMO

Biosurfactants have found widespread use across multiple industrial fields, including medicine, food, cosmetics, detergents, pulp, and paper, as well as the degradation of oil and fat. The culture broth of Aureobasidium pullulans A11231-1-58 isolated from flowers of Chrysanthemum boreale Makino exhibited potent surfactant activity. Surfactant activity-guided fractionation led to the isolation of three new biosurfactants, pullusurfactins A‒C (1‒3). Their chemical structures were established through the use of spectroscopic techniques, predominantly 1D and 2D NMR, in conjunction with mass measurements. We evaluated the surface tension activities of isolated compounds. At 1.0 mg l-1, these compounds showed high degrees of surfactant activity (31.15 dyne/cm, 33.75 dyne/cm, and 33.83 dyne/cm, respectively).


Assuntos
Chrysanthemum , Chrysanthemum/química , Chrysanthemum/metabolismo , Tensoativos/química
6.
Phytochemistry ; 214: 113828, 2023 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-37595773

RESUMO

Seven undescribed compounds, dentipellinones A‒D (1, 2, 5, and 6), dentipellinol (3), methoxyerinaceolactone B (4), and erinaceolactomer A (7), were isolated from the culture broth of Dentipellis fragilis. Chemical structures of these isolated compounds were determined by analyses of 1D and 2D-NMR and MS data in comparison with data reported in the literature. Absolute configurations of 1‒7 were also determined by Electronic Circular Dichroism calculations. The isolated compounds were evaluated for their anti-inflammatory effects on NO production and pro-inflammatory cytokines levels in LPS-stimulated RAW264.7 cells. Compounds 5 and 7 were evaluated for their anti-inflammatory effects on NO production and pro-inflammatory cytokine levels in LPS-stimulated RAW264.7 cells. They exhibited inhibitory effects on LPS-induced NO production in a dose-dependent manner, and significantly reduced the levels of inflammatory-related cytokines such as IL-1ß and IL-6. TNF-α was not involved in the anti-inflammatory effects of these compounds. Finally, compounds 5 and 7 showed significant anti-inflammatory effects.

7.
J Microbiol Biotechnol ; 33(8): 1023-1029, 2023 Aug 28.
Artigo em Inglês | MEDLINE | ID: mdl-37280777

RESUMO

Biosurfactants reduce surface and interfacial tension due to their amphiphilic properties and are an eco-friendly alternative for chemical surfactants. In this study, a new yeast strain JAF-11 that produces a biosurfactant was selected using drop collapse method, and the properties of the extracts were investigated. The nucleotide sequences of the strain were compared with closely related strains and identified based on the D1/D2 domain of the large subunit ribosomal DNA (LSU) and internal transcribed spacer (ITS) regions. Neodothiora populina CPC 39399T, the closest species with strain JAF-11, showed a sequence similarity of 97.75% for LSU and 94.27% for ITS, respectively. The result suggests that the strain JAF-11 represents a distinct species that cannot be assigned to any existing genus or species in the family Dothideaceae. Strain JAF-11 produced a biosurfactant reducing the surface tension of water from 72 mN/m to 34.5 mN/m on the sixth day of culture and the result of measuring the critical micelle concentration (CMC) by extracting the crude biosurfactant was found to be 24 mg/l. The molecular weight 502 of the purified biosurfactant was confirmed by measuring the fast atom bombardment mass spectrum. The chemical structure was analyzed by measuring 1H nuclear magnetic resonance (NMR), 13C NMR, and two-dimensional NMRs of the compound. The molecular formula was C26H46O9, and it was composed of one octanoyl group and two hexanoyl groups to myo-inositol moiety. The new biosurfactant is the first report of a compound produced by a new yeast strain, JAF-11.


Assuntos
Ascomicetos , Leveduras , Filogenia , Micelas , Tensão Superficial , Tensoativos
9.
J Antibiot (Tokyo) ; 76(6): 351-354, 2023 06.
Artigo em Inglês | MEDLINE | ID: mdl-37012405

RESUMO

During the search for natural antibiotics from fungal metabolites, a new cyathane diterpenoid, fragilicine A (1), and three known cyathane diterpenoids, erinacines I, A, and B (2-4) were isolated from the culture broth of Dentipellis fragilis. Chemical structures of 1-4 were determined by analyses of 1D- and 2D-NMR and MS data and by comparisons with data of those reported in the literature. These isolated compounds were assessed for their antimicrobial activities against Bacillus subtilis, B. atrophaeus, B. cereus, Listeria monocytogenes, Fusarium oxysporum, Diaporthe sp., and Rhizoctonia solani. These compounds showed weak antimicrobial activities.


Assuntos
Antibacterianos , Diterpenos , Antibacterianos/química , Bacillus subtilis/metabolismo
10.
J Antibiot (Tokyo) ; 76(1): 52-55, 2023 01.
Artigo em Inglês | MEDLINE | ID: mdl-36380241

RESUMO

A new p-terphenyl derivative, hydroxystrepantibin D (1), was isolated along with two known p-terphenyls (2 and 3) from the culture broth of Phlebiopsis castanea. These compounds were isolated using silica gel column chromatography, reversed-phase medium-pressure liquid chromatography, Sephadex LH-20 column chromatography, and preparative HPLC. Their structures were determined based on spectroscopic methods. These compounds exhibited free radical scavenging activities with IC50 values in the range from 22.2 to 158.4 µM against 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical and in the range from 161.1 to 356.1 µM against 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical.


Assuntos
Sequestradores de Radicais Livres , Compostos de Terfenil , Sequestradores de Radicais Livres/farmacologia , Sequestradores de Radicais Livres/química , Glucosídeos/farmacologia , Glucosídeos/química , Compostos de Bifenilo , Ácidos Sulfônicos/química , Antioxidantes/farmacologia , Antioxidantes/química , Picratos
11.
J Antibiot (Tokyo) ; 75(10): 589-592, 2022 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-35986093

RESUMO

Biosurfactants have been widely used in various industrial fields including medicine, food, cosmetics, detergent, pulp and paper, and oil and fat degradation. The culture broth of Aureobasidium pullulans A11211-4-57 using glucose as carbon source exhibited potent surfactant activity. The culture broth was separated by column chromatographies using ODS, silica gel, and Sephadex LH-20 resins, consecutively, to provide two biosurfactants. Based on mass and NMR measurements, their structures were determined as myo-inositol lipids and named pullusurfactans F and G. These compounds showed a high degree of activity, with 27.25 mN/m and 24.07 mN/m, respectively, at 1.0 mg l-1, which is useful for washing and cleaning agents.


Assuntos
Ascomicetos , Erigeron , Ascomicetos/metabolismo , Aureobasidium , Tensoativos/química
12.
J Nat Med ; 76(2): 476-481, 2022 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-35034277

RESUMO

Four new isoindolinone derivatives, daldinans D‒G (3‒6), together with two known compounds, daldinans A and B (1 and 2), were isolated from the stroma of the ascomycete Daldinia concentrica. Chemical structures of the isolated compounds were determined by spectroscopic methods. All of these compounds exhibited antioxidant activities with IC50 values of 3.21 to 39.67 µM in the 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) assay.


Assuntos
Antioxidantes , Ascomicetos , Antioxidantes/química , Ascomicetos/química , Ftalimidas
13.
J Antibiot (Tokyo) ; 75(2): 113-116, 2022 02.
Artigo em Inglês | MEDLINE | ID: mdl-34903860

RESUMO

During the search for natural antioxidants from fungal metabolites, three new sesquiterpene derivatives (1-3) have been isolated from the culture broth of Coprinopsis echinospora. Their structures were determined by spectroscopic methods, mainly NMR and mass spectrometric analyses. These compounds exhibited antioxidant activity with IC50 values in the range of 34.4-144.5 µM in the 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical-scavenging assay.


Assuntos
Agaricales/química , Antioxidantes/química , Antioxidantes/isolamento & purificação , Benzotiazóis/química , Compostos de Bifenilo , Meios de Cultura , Sequestradores de Radicais Livres/farmacologia , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Picratos , Ácidos Sulfônicos/química
14.
Mycobiology ; 49(4): 434-437, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-34512086

RESUMO

In our ongoing search for new secondary metabolites from fungi, a basidiomycete fungus Irpex consors was selected for mycochemical investigation, and three new zwitterionic alkaloids (1-3) and five known compounds (4-8) were isolated from the culture broth (16 l) of I. consors. The culture filtrate was fractionated by a series of column chromatography including Diaion HP-20, silica gel, and Sephadex LH-20, Sep-Pak C18 cartridge, medium pressure liquid chromatography (MPLC), and high pressure liquid chromatography (HPLC) to yield eight compounds (1-8). The structures of the isolated compounds were elucidated by the interpretation of nuclear magnetic resonance (NMR) spectra and high-resolution mass spectrometry (HR-MS). Their antioxidant and antibacterial activities were examined. The zwitterionic structures of three new sesquiterpene alkaloids (1-3) were determined together with five known compounds identified as stereumamide E (4), stereumamide G (5), stereumamide H (6), stereumamide D (7), and sterostrein H (8). This is the first report of the zwitterionic alkaloids in the culture broth of I. consors. Three new zwitterionic alkaloids were named as consoramides A-C (1-3).

15.
Biol Pharm Bull ; 44(5): 686-690, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-33952824

RESUMO

Although more than 400 species of Cordyceps s.l. have been identified, most have not been well explored regarding their potential for medicinal use. In this study, the profiles of constituents of ten different species of Ophiocordyceps, which is an unexplored species of Cordyceps, were analyzed and their anti-tumor effects were further examined. Although all Ophiocordyceps samples exhibited similar peak patterns, Ophiocordyceps gracilioides (O. grac) had a distinct constituent profile from the other samples. Furthermore, O. grac was the most active in suppressing the transcriptional activities of both nuclear factor-kappa B (NF-κB) and signal transducer and activator of transcription (STAT)3, and the production of interleukin (IL)-6 from breast cancer cells. This study demonstrated that O. grac is a relatively unexplored Cordyceps s.l. that may have medicinal potential to inhibit the NFκB-STAT3-IL-6 inflammatory pathway in cancer.


Assuntos
Produtos Biológicos/farmacologia , Hypocreales/química , Neoplasias/tratamento farmacológico , Animais , Produtos Biológicos/isolamento & purificação , Produtos Biológicos/uso terapêutico , Linhagem Celular Tumoral , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Interleucina-6/metabolismo , Camundongos , NF-kappa B/metabolismo , Neoplasias/imunologia , Neoplasias/patologia , Fator de Transcrição STAT3/metabolismo , Transdução de Sinais/efeitos dos fármacos , Transdução de Sinais/imunologia
16.
J Antibiot (Tokyo) ; 74(8): 538-541, 2021 08.
Artigo em Inglês | MEDLINE | ID: mdl-34045694

RESUMO

In our effort to find antimicrobial agents from higher fungi, we isolated a new compound, dentipellin (1), along with three known glycosylated diterpenes, erinacines A-C (2-4) from culture broth of Dentipellis fragilis. Their chemical structures were determined by spectroscopic methods including NMR and mass measurements. These compounds exhibited weak antibacterial and antifungal activities.


Assuntos
Antibacterianos/biossíntese , Basidiomycota/química , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Antifúngicos/isolamento & purificação , Antifúngicos/farmacologia , Bactérias/efeitos dos fármacos , Meios de Cultura , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Fungos/efeitos dos fármacos , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Conformação Molecular
17.
J Nat Med ; 75(4): 824-832, 2021 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-33905080

RESUMO

Ophiocordyceps gracilioides is an entomoparasitic ascomycetes whose bioactivity has not been examined in detail. In this study, we identified the bioactive compounds ergosterol peroxide (EPO) and ergosterol (ERG) from the MeOH extract of O. gracilioides mycelia related to its anti-cancer effects by targeting the Nuclear Factor kappa B (NF-ĸB)/Signal Transducer and Activator of Transcription 3 (STAT3) inflammatory pathways. Using gene-reporter assays, we demonstrated that EPO markedly inhibits both NF-ĸB and STAT3 activity in 4T1 cells, whereas ERG had limited effect. Consistent with their effects on NF-ĸB and STAT3 activity, EPO, but not ERG, exerted anti-proliferative effects on 4T1 cells. Furthermore, EPO significant inhibited both the migration and invasion of 4T1 cells in vitro, and pre-treatment of 4T1 cells with EPO significantly inhibited the formation of experimental lung metastases in vivo. Collectively, we demonstrated that ERG and EPO can be isolated from O. gracilioides mycelia, and further identified EPO as an active constituent of its anti-metastatic effects through the inhibition of NF-ĸB and STAT3 inflammatory pathways in 4T1 breast cancer cells.


Assuntos
Neoplasias da Mama , Neoplasias da Mama/tratamento farmacológico , Linhagem Celular Tumoral , Ergosterol/análogos & derivados , Feminino , Fungos , Humanos , NF-kappa B
18.
Bioorg Med Chem Lett ; 36: 127787, 2021 03 15.
Artigo em Inglês | MEDLINE | ID: mdl-33460740

RESUMO

SmltD is an ATP-dependent ligase that catalyzes the condensation of UDP-MurNAc-l-Ala and l-Glu to form UDP-MurNAc-l-Ala-l-Glu, in the newly discovered peptidoglycan biosynthesis pathway of a Gram-negative multiple-drug-resistant pathogen, Stenotrophomonas maltophilia. Phytochemical investigation of the 70% ethanol extract from Woodfordia fruticosa flowers collected in Myanmar led to the identification of anti-SmltD active flavonoids, kaempferol 3-O-(6''-galloyl)-ß-d-glucopyranoside (1), astragalin (2), and juglalin (3). Among them, 1 showed the most potent SmltD inhibitory activity. An enzyme steady-state kinetic study revealed that 1 exerted competitive inhibition with respect to ATP. The results of this study provided an attractive foundation for the further development of novel inhibitors of SmltD.


Assuntos
DNA Ligase Dependente de ATP/antagonistas & inibidores , Inibidores Enzimáticos/farmacologia , Flavonoides/farmacologia , Peptidoglicano/biossíntese , Woodfordia/química , DNA Ligase Dependente de ATP/metabolismo , Relação Dose-Resposta a Droga , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Flavonoides/química , Flavonoides/isolamento & purificação , Estrutura Molecular , Peptidoglicano/química , Stenotrophomonas maltophilia/enzimologia , Relação Estrutura-Atividade
19.
Mycobiology ; 49(6): 604-606, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-35035252

RESUMO

In our ongoing search for new secondary metabolites from fungal strains, one novel compound (1) and nine known compounds (2-10) were isolated from the EtOAc-soluble layer of the culture broth of Panus rudis. The culture broth of P. rudis was extracted in acetone and fractionated by solvent partition; column chromatography using silica gel, Sephadex LH-20, and Sephadex G-10; MPLC; and HPLC. The structures of isolated compounds were elucidated by one- and two-dimensional NMR and LC-ESI-mass measurements. One new compound, panepoxydiol (1), and nine known compounds, (E)-3-(3-hydroxy-3-methylbut-1-en-1-yl)-7-oxabicyclo[4.1.0]hept-3-ene-2,5-diol (2), isopanepoxydone (3), neopanepoxydone (4), panepoxydone (5), panepophenanthrin (6), 4-hydroxy-2,2-dimethyl-6-methoxychromane (7), 6-hydroxy-2,2-dimethyl-3-chromen (8), 2,2-dimethyl-6-methoxychroman-4-one (9), 3,4-dihydroxy-2,2-dimethyl-6-methoxychromane (10), were isolated from the culture broth of P. rudis. This is the first report of isolation of a new compound panepoxydiol (1) and nine other chemical constituents (2-5, 7-10) from the culture broth of P. rudis.

20.
Chem Biodivers ; 17(9): e2000303, 2020 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-32592287

RESUMO

A new decenoic acid derivative, gelliodesinic acid, and a naturally new alkaloid, together with three known furanoterpenoids and two known indole alkaloids, were isolated from the MeOH extract of the marine sponge Gelliodes sp. collected in Vietnam. The chemical structures of the isolated compounds were determined by analyses of 1D- and 2D-NMR and MS data and by comparisons of the data with those reported in the literature. The cytotoxicity assay against HeLa, MCF-7, and A549 cancer cell lines revealed that the three known furanoterpenes exhibited cytotoxic activities with IC50 values ranging from 23.6 to 75.5 µM against the three cell lines, and that 1H-indole-3-carboxylic acid showed cytotoxicity with an IC50 value of 89.2 µM against A549 cancer cell lines.


Assuntos
Alcaloides/farmacologia , Antineoplásicos/farmacologia , Ácidos Graxos/farmacologia , Poríferos/química , Alcaloides/química , Alcaloides/isolamento & purificação , Animais , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Proliferação de Células/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Ácidos Graxos/química , Ácidos Graxos/isolamento & purificação , Estrutura Molecular , Relação Estrutura-Atividade , Células Tumorais Cultivadas , Vietnã
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