RESUMO
Eight new phenethoxy derivatives, trichoasperellins A-H (1-8), were isolated from the endophytic fungus Trichoderma asperellum G10 isolated from the medicinal plant Areca catechu L. The structures of these compounds were elucidated from spectroscopic data, J-based configurational analysis, and Mosher's methods. Compounds 1-4 and 6-8 bear one or two multioxidized C7 moieties with the same carbon skeleton. The carbon skeletons of compounds 6-8 are new, all containing three moieties connected via two acetal carbons similar to those of disaccharide glycosides. Compound 4 inhibited nitric oxide production with an IC50 value of 48.3 µM, comparable to that of the positive control indomethacin (IC50, 42.3 µM).
Assuntos
Hypocreales , Trichoderma , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Areca , Carbono , Estrutura Molecular , Trichoderma/químicaRESUMO
Macrofungi Ganoderma is a valuable medicinal fungus resource for human health and longevity in China. In this study, ten undescribed compounds including seven lostane-type triterpenoids, ganodaustralic acids A â¼ G (1-7), one pair of meroterpenoid enantiomers, (-)-6'-O-ethyllingzhiol (8) and (+)-6'-O-ethyllingzhiol (9), and one polyhydroxylated sterol, 3-O-acetyl-fomentarol C (10), together with eight known compounds (11-18), were isolated from the fruiting bodies of Ganoderma australe. The structures of the new compounds were elucidated by extensive spectroscopic analysis as well as NMR and electronic circular dichroism (ECD) calculations. Compounds 4, 8, 9, and 12 showed significant α-glucosidase inhibitory activities with IC50 values in the range of 4.1-11.7 µM, which were superior to that of positive control acarbose (213 µM). Only compound 7 exhibited weak cytotoxicity against SGC-7901 cells.
Assuntos
Antineoplásicos/farmacologia , Ganoderma/química , Inibidores de Glicosídeo Hidrolases/farmacologia , Terpenos/farmacologia , alfa-Glucosidases/metabolismo , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Carpóforos/química , Inibidores de Glicosídeo Hidrolases/química , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Humanos , Estrutura Molecular , Relação Estrutura-Atividade , Terpenos/química , Terpenos/isolamento & purificaçãoRESUMO
Four new indole-diterpenoids, named penerpenes K-N (1-4), along with twelve known ones (5-16), were isolated from the fermentation broth produced by adding L-tryptophan to the culture medium of the marine-derived fungus Penicillium sp. KFD28. The structures of the new compounds were elucidated extensively by 1D and 2D NMR, HRESIMS data spectroscopic analyses and ECD calculations. Compound 4 represents the second example of paxilline-type indole diterpene bearing a 1,3-dioxepane ring. Three compounds (4, 9, and 15) were cytotoxic to cancer cell lines, of which compound 9 was the most active and showed cytotoxic activity against the human liver cancer cell line BeL-7402 with an IC50 value of 5.3 µM. Moreover, six compounds (5, 7, 10, 12, 14, and 15) showed antibacterial activities against Staphylococcus aureus ATCC 6538 and Bacillus subtilis ATCC 6633.
Assuntos
Antibacterianos/farmacologia , Antineoplásicos/farmacologia , Diterpenos/farmacologia , Indóis/farmacologia , Penicillium , Animais , Antibacterianos/química , Antineoplásicos/química , Organismos Aquáticos , Linhagem Celular Tumoral/efeitos dos fármacos , Diterpenos/química , Humanos , Indóis/química , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Staphylococcus aureus/efeitos dos fármacosRESUMO
Two new 2-(2-phenylethyl)chromone derivatives (1-2) were isolated from the ethyl acetate extract of artificial agarwood induced by holing method originating from Aquilaria sinensis (Lour.) Gilg, and they were isolated from this genus for the first time. The structures of these two new compounds were elucidated by extensive spectroscopic analyses, including UV, IR, one- and two-dimensional NMR and HRESIMS measurements. Bioassay tests of these two new compounds showed compounds 1 and 2 had weak inhibitory activity against acetylcholinesterase at a concentration of 50.0 µg/ml.
Assuntos
Acetilcolinesterase , Thymelaeaceae , Inibidores da Colinesterase/farmacologia , Flavonoides , Estrutura Molecular , MadeiraRESUMO
Two new compounds named asperpenes D (1) and E (2) were isolated from the marine-derived fungus Aspergillus sp. SCS-KFD66. Their structures were determined on the basis of spectroscopic methods. Compound 2 represents the first natural product bearing a 2-substituted-5-oxo-4-phenyl-2,5-dihydrofuran-3-carboxylic acid skeleton. All the compounds were tested for enzyme inhibitory activity against AChE and α-glucosidase and DPPH radical scavenging activity, respectively. [Formula: see text].
Assuntos
Produtos Biológicos , Bivalves , Animais , Aspergillus , Estrutura Molecular , alfa-GlucosidasesRESUMO
Two new compounds named epipaxilline (1) and penerpene J (2) were isolated from the marine-derived fungus Penicillium sp. KFD28. Their structures including absolute configurations were determined on the basis of spectroscopic methods and ECD analysis. Compounds 1 and 2 showed inhibitory activities against PTP1B with IC50 values of 31.5 and 9.5 µM, respectively, and compound 2 also showed inhibitory activities against TCPTP with IC50 value of 14.7 µM.
Assuntos
Diterpenos , Penicillium , Fungos , Indóis , Estrutura MolecularRESUMO
Chemical constituents were isolated and purified from fruiting bodies of Ganoderma calidophilum by various column chromatographic techniques, and their chemical structures were identified through combined analysis of physicochemical properties and spectral data. As a result, 11 compounds were isolated and identified as(24E)-lanosta-8,24-dien-3,11-dione-26-al(1), ganoderone A(2), 3-oxo-15α-acetoxy-lanosta-7,9(11), 24-trien-26-oleic acid(3),(23E)-27-nor-lanosta-8,23-diene-3,7,25-trione(4), ganodecanone B(5), ganoderic aldehyde A(6), 11ß-hydroxy-lucidadiol(7), 3,4-dihydroxyacetophenone(8), methyl gentiate(9), ganoleucin C(10), ganotheaecolumol H(11). Among them, compound 1 is a new triterpenoid. The cytotoxic activities of all of the compounds against tumor cell lines were evaluated. The results showed that compounds 1, 3, 4 and 6 showed cytotoxic activity against BEL-7402, with IC_(50) values of 26.55, 11.35, 23.23, 18.66 µmol·L~(-1); compounds 1 and 3-6 showed cytotoxic activity against K562, with IC_(50) values of 5.79, 22.16, 12.16, 35.32, and 5.59 µmol·L~(-1), and compound 4 showed cytotoxic activity against A549, with IC_(50) value of 42.50 µmol·L~(-1).
Assuntos
Ganoderma , Triterpenos , Linhagem Celular Tumoral , Carpóforos , Estrutura Molecular , Triterpenos/farmacologiaRESUMO
Seven compounds were isolated from a marine-derived fungus Aspergillus sp. ZF-79, including three new polyketides (1-3), named asperochrins D-F, along with four known compounds 4-7. Their structures were determined on the basis of spectroscopic methods. All the compounds were tested for quorum sensing inhibitory (QSI) activity. Compounds 1, 3, 4, 5, and 6 exhibited QSI activity against Chromobacterium violaceum CV026 with MIC values of 50, 100, 50, 50, and 6.25 µM, respectively.
Assuntos
Policetídeos , Percepção de Quorum , Antibacterianos/farmacologia , Aspergillus , Chromobacterium , Estrutura Molecular , Policetídeos/farmacologia , Percepção de Quorum/efeitos dos fármacosRESUMO
The metabolites of the genus Marasmius are diverse, showing good research prospects for finding new bioactive molecules. In order to explore the active metabolites of the fungi Marasmius berteroi, the deep chemical investigation on the bioactive compounds from its cultures was undertaken, which led to the isolation of three new naphthalene compounds dipolynaphthalenes A-B (1,2) and naphthone C (3), as well as 12 known compounds (4-15). Compounds 1, 2, and 4 are dimeric naphthalene compounds. Their structures were elucidated by MS, 1D and 2D NMR spectroscopic data, as well as ECD calculations. Compounds 2-4 and 7 exhibited acetylcholinesterase (AChE) inhibitory activities at the concentration of 50 µg/mL with inhibition ratios of 42.74%, 44.63%, 39.50% and 51.49%, respectively. Compounds 5 and 7,8 showed weak inhibitory activities towards two tumor cell lines, with IC50 of 0.10, 0.076 and 0.058 mM (K562) and 0.13, 0.18, and 0.15 mM (SGC-7901), respectively.
Assuntos
Marasmius/metabolismo , Micélio/metabolismo , Naftalenos/metabolismoRESUMO
Five new indole-terpenoids named penerpenes E-I (1-5), along with seven known ones (6-12), were isolated from the marine-derived fungus Penicillium sp. KFD28 from a bivalve mollusk, Meretrix lusoria. The structures of the new compounds were elucidated from spectroscopic data and ECD spectroscopic analyses. Compound 1 was assigned as an indole-diterpenoid with a unique 6/5/5/6/6/5/5 heptacyclic ring system. Compound 2 represents an indole-diterpenoid with a new carbon skeleton derived from paxilline by the loss of three carbons (C-23/24/25). Compound 3 contains an additional oxygen atom between C-21 and C-22 compared to paxilline to form an unusual 6/5/5/6/6/7 hexacyclic ring system bearing a 1,3-dioxepane ring, which is rarely encountered in natural products. Compounds 1, 2, 4, and 6 showed inhibitory activities against protein tyrosine phosphatase 1B (PTP1B) with IC50 values of 14, 27, 23, and 13 µM, respectively.
Assuntos
Diterpenos/farmacologia , Indóis/farmacologia , Biologia Marinha , Penicillium/química , Proteínas Tirosina Fosfatases/antagonistas & inibidores , Diterpenos/química , Indóis/químicaRESUMO
Seven new quinazoline-containing indole alkaloids (1-7) named aspertoryadins A-G, along with nine known ones (8-16), were isolated from the marine-derived fungus Aspergillus sp. HNMF114 from the bivalve mollusk Sanguinolaria chinensis. The structures of the new compounds were elucidated from spectroscopic data, X-ray diffraction analysis, ECD spectra analysis, and ECD calculations. Compound 1 bears an aminosulfonyl group in the structure, which is rarely encountered in natural products. Compounds 6, 7, and 13 exhibited quorum sensing inhibitory activity against Chromobacterium violaceum CV026 with MIC values of 32, 32, and 16 µg/well, respectively.
Assuntos
Aspergillus/química , Alcaloides Indólicos/farmacologia , Quinazolinas/farmacologia , Água do Mar/microbiologia , Alcaloides Indólicos/química , Alcaloides Indólicos/isolamento & purificação , Testes de Sensibilidade Microbiana , Estrutura Molecular , Quinazolinas/química , Quinazolinas/isolamento & purificação , Percepção de Quorum/efeitos dos fármacosRESUMO
Four new ansamycins, named divergolides T-W (1-4), along with two known analogs were isolated from the fermentation broth of the mangrove-derived actinomycete Streptomyces sp. KFD18. The structures of the compounds, including the absolute configurations of their stereogenic carbons, were determined by spectroscopic data and single-crystal X-ray diffraction analysis. Compounds 1-4 showed cytotoxic activity against the human gastric cancer cell line SGC-7901, the human leukemic cell line K562, the HeLa cell line, and the human lung carcinoma cell line A549, with 1 being the most active while compounds 5 and 6 were inactive against all the tested cell lines. Compounds 1 and 3 showed very potent and specific cytotoxic activities (IC50 2.8 and 4.7 µM, respectively) against the SGC-7901 cells. Further, the apoptosis-inducing effect of 1 and 3 against SGC-7901 cells was demonstrated by two kinds of staining methods for the first time.
Assuntos
Antibióticos Antineoplásicos/farmacologia , Apoptose/efeitos dos fármacos , Lactamas Macrocíclicas/farmacologia , Streptomyces/química , Antibióticos Antineoplásicos/química , Antibióticos Antineoplásicos/isolamento & purificação , Linhagem Celular Tumoral , Cristalografia por Raios X , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Lactamas Macrocíclicas/química , Lactamas Macrocíclicas/isolamento & purificação , Estrutura Molecular , Áreas AlagadasRESUMO
Chemical investigation on the cultures of the fungus Cordyceps spp., a strain from cell fusion between Cordyceps militaris and Cordyceps cicadae, resulted in the isolation of 13 compounds including 2 new ones named 2-(5-(3-oxobutyl) furan-2-yl) acetic acid (1) and cordycepone (2). Their structures were elucidated from the analysis of 1D/2D NMR and CD data. Among them, compounds 1, 7-9, at a concentration of 50 µg/ml, showed weak inhibitory activity against AChE. Moreover, compounds 6, 9, and 11 showed moderate inhibitory activity against the nematode Panagrellus redivivus with mortality ratio of 79.0, 71.7, and 72.3% at 2.5 mg/ml, respectively.
Assuntos
Fusão Celular , Cordyceps/química , Cordyceps/citologia , Acetilcolinesterase , Animais , Anti-Helmínticos/química , Anti-Helmínticos/farmacologia , Bioensaio , Inibidores da Colinesterase/química , Inibidores da Colinesterase/farmacologia , Furanos/química , Furanos/metabolismo , Estrutura Molecular , Nematoides/efeitos dos fármacosRESUMO
Two new 2-(2-phenylethyl)chromone derivatives (1â»2), comprising 5,6,7,8-tetrahydro-2-(2-phenylethyl)chromone and benzylacetone moieties, together with one new 2-(2-phenylethenyl)chromone (3) were isolated from the ethyl acetate extraction of agarwood originated from Gyrinops salicifolia Ridl. All structures were unambiguously elucidated on the basis of 1D and 2D NMR spectra as well as by HRESIMS data. All isolated compounds were tested for acetylcholinesterase (AChE) inhibitory activity and cytotoxic activity against human myeloid leukemia cell line (K562). However, none of the compounds displayed AChE inhibitory activity at a concentration of 50 µg mL-1 or cytotoxic activity against K562 cell line.
Assuntos
Flavonoides/química , Thymelaeaceae/química , Linhagem Celular Tumoral , Flavonoides/farmacologia , Humanos , Espectroscopia de Ressonância Magnética/métodos , Estrutura Molecular , Relação Estrutura-AtividadeRESUMO
Chemical constituents were isolated from the fruiting bodies of Ganoderma australe by various column chromatographic techniques and HPLC method, and their chemical structures were identified through the combined analysis of physicochemical properties and spectral data. Meanwhile, their α-glucosidase inhibitory activity and anti-oxidative ability were evaluated. Seven compounds were isolated from G. australe and were identified as 6-methoxyl-cyclo-(Phe-Ile)(1), applanoxidic acid A methyl ester(2), ergosta-7,22 E-dien-3ß-ol(3), cinnamic acid(4), 5α,8α-epidioxy-(20S,22E,24R)-ergosta-6,22-diene-3ß-ol(5), 1-(3, 4-dihydroxyphenyl) ethanone(6), salicylic acid(7) and benzoic acid(8). Among the compounds, compound 1 was a new cyclic dipeptide. Compound 2 was a new lanosta natural product, and compounds 4, 6, 7 and 8 were obtained from G. australe for the first time. Moreover, compounds 4 and 8 exhibited α-glucosidase inhibitory activity with inhibition rates of 36.8% and 34.7%, and compounds 4, 7 and 8 had a certain activity in DPPH free radical scavenging activity with IC_(50) values of 0.168, 0.458 and 0.170 g·L~(-1), respectively. The DPPH radical scavenging rate of compound 1 was 41.1%.
Assuntos
Carpóforos/química , Ganoderma/química , Sequestradores de Radicais Livres/isolamento & purificação , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Estrutura MolecularRESUMO
Streptococcus agalactiae is a hazardous pathogen that can cause great harm to humans and fish. In the present study, the known fungal metabolite helvolic acid (10), seven new helvolic acid derivatives named 16- O-deacetylhelvolic acid 21,16-lactone (2), 6- O-propionyl-6,16- O-dideacetylhelvolic acid 21,16-lactone (3), 1,2-dihydro-6,16- O-dideacetylhelvolic acid 21,16-lactone (4), 1,2-dihydro-16- O-deacetylhelvolic acid 21,16-lactone (5), 16- O-propionyl-16- O-deacetylhelvolic acid (6), 6- O-propionyl-6- O-deacetylhelvolic acid (7), and 24- epi-6ß,16ß-diacetoxy-25-hydroxy-3,7-dioxo-29-nordammara-1,17(20)-diene-21,24-lactone (9), and two known ones (1 and 8) were isolated from the marine-derived fungus Aspergillus fumigatus HNMF0047 obtained from an unidentified sponge from Wenchang Beach, Hainan Province, China. The structures and the absolute configurations of the new compounds were unambiguously elucidated by spectroscopic data and electronic circular dichroism (ECD) spectroscopic analyses along with quantum ECD calculations. In addition, the spectroscopic data of compound 1 are reported here for the first time, the configuration of C-24 of known compound 8 was revised based on comparison of its ROESY data with its C-24 epimer 9, and the absolute configuration of 8 was also determined for the first time. Compounds 6, 7, and 10 showed stronger antibacterial activity than a tobramycin control against S. agalactiae with MIC values of 16, 2, and 8 µg/mL, respectively.
Assuntos
Antibacterianos/química , Antibacterianos/farmacologia , Aspergillus fumigatus/química , Ácido Fusídico/análogos & derivados , Streptococcus agalactiae/efeitos dos fármacos , Dicroísmo Circular , Ácido Fusídico/química , Ácido Fusídico/farmacologia , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Conformação Molecular , Estrutura Molecular , Tobramicina/farmacologiaRESUMO
An actinomycete strain, 2603PH03T, was isolated from a mangrove rhizosphere soil sample collected in Wenchang, China. Phylogenetic analysis of the 16S rRNA gene sequence of strain 2603PH03T indicated high similarity to Verrucosispora gifthornensis DSM 44337T (99.4%), Verrucosispora andamanensis (99.4%), Verrucosispora fiedleri MG-37T (99.4%) and Verrucosispora maris AB18-032T (99.4%). The cell wall was found to contain meso-diaminopimelic acid and glycine. The major menaquinones were identified as MK-9(H4), MK-9(H6) and MK-9(H8), with MK-9(H2), MK-10(H2), MK-9(H10) and MK-10(H6) as minor components. The characteristic whole cell sugars were found to be xylose and mannose. The phospholipid profile was found to contain phosphatidylethanolamine, diphosphatidylglycerol, phosphatidylinositol mannoside, phosphatidylinositol, phosphatidylserine and an unidentified phospholipid. The DNA G+C content was determined to be 70.1 mol%. The results of physiological and biochemical tests and low DNA-DNA relatedness readily distinguished the isolate from the closely related species. On the basis of these phenotypic and genotypic data, strain 2603PH03T is concluded to represent a novel species of the genus Verrucosispora, for which the name Verrucosispora rhizosphaerae sp. nov. is proposed. The type strain is 2603PH03T (=CCTCC AA 2016023T = DSM 45673T).
Assuntos
Actinobacteria/classificação , Rizosfera , Microbiologia do Solo , Actinobacteria/química , Actinobacteria/genética , Actinobacteria/isolamento & purificação , Fenótipo , Filogenia , RNA Ribossômico 16S/genética , Análise de Sequência de DNARESUMO
Five new compounds named asperpenes A-C (1â»3), 12,13-dedihydroversiol (4), and methyl 6-oxo-3,6-dihydro-2H-pyran-4-carboxylate (5), along with 10 known compounds (6â»15), were isolated from the fermentation broth of Aspergillus sp. SCS-KFD66 associated with a bivalve mollusk, Sanguinolaria chinensis, collected from Haikou Bay, China. The structures of the compounds, including the absolute configurations of their stereogenic carbons, were unambiguously determined by spectroscopic data, single-crystal X-ray diffraction analysis, and electronic circular dichroism (ECD) spectral analysis, along with quantum ECD calculations. The growth inhibitory activity of the compounds against four pathogenic bacterial (Escherichia coli ATCC 25922, Staphylococcus aureus ATCC 6538, Listeria monocytogenes ATCC 1911, and Bacillus subtilis ATCC 6633), their enzyme inhibitory activities against acetylcholinesterase and α-glucosidase, and their DPPH radical scavenging activity were evaluated.
Assuntos
Organismos Aquáticos/metabolismo , Aspergillus/metabolismo , Bactérias/efeitos dos fármacos , Produtos Biológicos/farmacologia , Bivalves/microbiologia , Acetilcolinesterase/química , Animais , Antibacterianos/química , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Produtos Biológicos/química , Produtos Biológicos/isolamento & purificação , Compostos de Bifenilo/antagonistas & inibidores , China , Inibidores da Colinesterase/química , Inibidores da Colinesterase/isolamento & purificação , Inibidores da Colinesterase/farmacologia , Dicroísmo Circular , Cristalografia por Raios X , Sequestradores de Radicais Livres/química , Sequestradores de Radicais Livres/isolamento & purificação , Sequestradores de Radicais Livres/farmacologia , Inibidores de Glicosídeo Hidrolases/química , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Inibidores de Glicosídeo Hidrolases/farmacologia , Testes de Sensibilidade Microbiana , Estrutura Molecular , Picratos/antagonistas & inibidores , alfa-Glucosidases/químicaRESUMO
Two new 2-(2-hydroxy-2-phenylethyl)chromones (1â2), along with three known 2-(2-phenylethyl)chromones (3â5), were isolated from the agarwood originating from Aquilaria crassna Pierre ex Lecomte. Their structures were determined by the spectroscopic methods including 1D and 2D NMR analysis and comparison with reported data in the literature. All the compounds were isolated from agarwood of A. crassna for the first time. Compounds 1 and 2 exhibited inhibitory activity against acetylcholinesterase (AChE) with 17.4 ± 0.6 and 15.8 ± 0.7%, respectively, at a concentration of 50 µg/ml. Besides, Compound 3 expressed antibacterial activities against Ralstonia solanacearum with diameter of the inhibition zone of 6.80 ± 0.08 mm at a concentration of 10 mg/ml.
Assuntos
Benzopiranos/isolamento & purificação , Inibidores da Colinesterase/isolamento & purificação , Medicamentos de Ervas Chinesas/isolamento & purificação , Thymelaeaceae/química , Antibacterianos/química , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Benzopiranos/química , Benzopiranos/farmacologia , Inibidores da Colinesterase/química , Inibidores da Colinesterase/farmacologia , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Flavonoides/química , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Madeira/químicaRESUMO
A phytochemical investigation of the alkaloid constituents from Trigonostemon filipes Y. T. Chang et S. L. Mo led to the isolation of two new indole alkaloids, trigonostemine G (1) and trigonostemone J (2), together with two known ones, trigonostemine A (3) and trigonostemine B (4). Their structures were determined by extensive spectroscopic methods. Compounds 1-4 exhibited moderate AChE inhibitory activity with inhibition ratio of 31.6, 31.7, 41.7, and 42.4%, respectively. In addition, compounds 1-2 showed weak cytotoxicity against K562 and BEL-7402 human cancer cell lines.