RESUMEN
Eight previously undescribed indole-diterpenoids named penerpenes O-V (1-8), together with seven known analogues (9-14), were isolated from the marine soft coral-derived fungus Aspergillus sp. ZF-104. Their structures including the absolute configurations of these compounds were assigned on the basis of spectroscopic data and ECD analysis along with quantum ECD and NMR calculations. Compounds 4 and 5 bear rare indolin-2-one units in their structures and 6 bears a reconstructed novel skeleton in which the indole ring and the terpenoid substructure are cleaved before they are reconnected through the nitrogen atom. Compounds 1, 2, 7, and 10 showed protein tyrosine phosphatase 1B (PTP1B) inhibitory activities comparable to that of the positive control NaVO3.
Asunto(s)
Antozoos , Diterpenos , Animales , Estructura Molecular , Proteína Tirosina Fosfatasa no Receptora Tipo 1 , Diterpenos/química , Indoles/farmacología , Indoles/química , Espectroscopía de Resonancia Magnética , Aspergillus/química , Antozoos/químicaRESUMEN
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).
Asunto(s)
Hypocreales , Trichoderma , Antiinflamatorios/química , Antiinflamatorios/farmacología , Areca , Carbono , Estructura Molecular , Trichoderma/químicaRESUMEN
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.
Asunto(s)
Antineoplásicos/farmacología , Ganoderma/química , Inhibidores de Glicósido Hidrolasas/farmacología , Terpenos/farmacología , alfa-Glucosidasas/metabolismo , Antineoplásicos/química , Antineoplásicos/aislamiento & purificación , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Ensayos de Selección de Medicamentos Antitumorales , Cuerpos Fructíferos de los Hongos/química , Inhibidores de Glicósido Hidrolasas/química , Inhibidores de Glicósido Hidrolasas/aislamiento & purificación , Humanos , Estructura Molecular , Relación Estructura-Actividad , Terpenos/química , Terpenos/aislamiento & purificaciónRESUMEN
By feeding tryptophan to the marine-derived fungus Aspergillus sp. HNMF114 from the bivalve mollusk Sanguinolaria chinensis, 3 new quinazoline-containing indole alkaloids, named aspertoryadins H-J (1-3), along with 16 known ones (4-19), were obtained. The structures of the new compounds were elucidated by the analysis of spectroscopic data combined with quantum chemical calculations of nuclear magnetic resonance (NMR) chemical shifts and electron capture detector (ECD) spectra. Structurally, compound 3 represents the first example of this type of compound, bearing an amide group at C-3. Compounds 10 and 16 showed potent α-glucosidase inhibitory activity with IC50 values of 7.18 and 5.29 µM, and compounds 13 and 14 showed a clear activation effect on the ryanodine receptor from Spodoptera frugiperda (sfRyR), which reduced the [Ca2+] ER by 37.1 and 36.2%, respectively.
RESUMEN
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).
Asunto(s)
Ganoderma , Triterpenos , Línea Celular Tumoral , Cuerpos Fructíferos de los Hongos , Estructura Molecular , Triterpenos/farmacologíaRESUMEN
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].
Asunto(s)
Productos Biológicos , Bivalvos , Animales , Aspergillus , Estructura Molecular , alfa-GlucosidasasRESUMEN
Three new dimeric 2-(2-phenylethyl)chromones crassin I â¼ K (1-3), together with one known analogue (4), were isolated from the artificial holing agarwood originating from Aquilaria sinensis. Their structures including the absolute configuration were elucidated by spectroscopic techniques (UV, IR, 1D and 2D NMR, ECD), and HRESIMS analysis, as well as by comparison with the literature data. Compounds 1 and 2 exhibited weak acetylcholinesterase inhibitory activity.
Asunto(s)
Cromonas/farmacología , Thymelaeaceae , Madera/química , Acetilcolinesterasa , Inhibidores de la Colinesterasa/farmacología , Cromonas/aislamiento & purificación , Flavonoides , Estructura Molecular , Thymelaeaceae/químicaRESUMEN
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.
Asunto(s)
Diterpenos , Penicillium , Hongos , Indoles , Estructura MolecularRESUMEN
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.
Asunto(s)
Marasmius/metabolismo , Micelio/metabolismo , Naftalenos/metabolismoRESUMEN
Patchouli is a tropical medicinal and spice crop with high economic value, and the endophytic microorganism is also one of its important components and can provide new active compounds with medicinal use. In the present study, four new biphenyl compounds named 3-O-demethylaltenuisol (1), (-)-dialtenuisol (5) and (+)-dialtenuisol (6), and altertoxin VII (9), as well as six known related compounds, were isolated from the patchouli (Pogostemon cablin) endophytic fungus Alternaria sp. PfuH1. The structures of the new compounds were elucidated from spectroscopic data, ECD spectra analysis, and ECD calculations. Compounds 5 and 6 are a pair of dimeric axially chiral enantiomers. Compounds 2, 4, and 9 showed antibacterial activities against S. agalactiae with MIC values of 9.3, 85.3, and 17.3 µg/mL, respectively, and compound 4 also showed weak antibacterial activity against E. coli with MIC value of 128 µg/mL.
Asunto(s)
Alternaria/química , Antibacterianos/farmacología , Compuestos de Bifenilo/farmacología , Pogostemon/microbiología , Antibacterianos/aislamiento & purificación , Compuestos de Bifenilo/aislamiento & purificación , Línea Celular Tumoral , China , Endófitos/química , Escherichia coli/efectos de los fármacos , Flores/microbiología , Humanos , Pruebas de Sensibilidad Microbiana , Estructura MolecularRESUMEN
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.
Asunto(s)
Policétidos , Percepción de Quorum , Antibacterianos/farmacología , Aspergillus , Chromobacterium , Estructura Molecular , Policétidos/farmacología , Percepción de Quorum/efectos de los fármacosRESUMEN
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.
Asunto(s)
Aspergillus/química , Alcaloides Indólicos/farmacología , Quinazolinas/farmacología , Agua de Mar/microbiología , Alcaloides Indólicos/química , Alcaloides Indólicos/aislamiento & purificación , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Quinazolinas/química , Quinazolinas/aislamiento & purificación , Percepción de Quorum/efectos de los fármacosRESUMEN
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.
Asunto(s)
Diterpenos/farmacología , Indoles/farmacología , Biología Marina , Penicillium/química , Proteínas Tirosina Fosfatasas/antagonistas & inhibidores , Diterpenos/química , Indoles/químicaRESUMEN
Four unusual indole-terpenoids, penerpenes A-D (1-4), along with two known ones paxilline (5) and emindole SB (6), were isolated from the marine-derived fungus Penicillium sp. KFD28. The absolute structures of 1-4 were elucidated on the basis of spectroscopic data and ECD spectra analysis along with quantum ECD calculations. Compounds 1 and 2 showed potent inhibitory activity toward protein tyrosine phosphatases (PTP1B and TCPTP). Plausible biosynthetic pathways of compounds 1-4 are proposed.
Asunto(s)
Inhibidores Enzimáticos/farmacología , Indoles/farmacología , Penicillium/química , Proteína Tirosina Fosfatasa no Receptora Tipo 1/antagonistas & inhibidores , Proteína Tirosina Fosfatasa no Receptora Tipo 2/antagonistas & inhibidores , Terpenos/farmacología , Inhibidores Enzimáticos/química , Inhibidores Enzimáticos/aislamiento & purificación , Humanos , Indoles/química , Indoles/aislamiento & purificación , Modelos Moleculares , Conformación Molecular , Proteína Tirosina Fosfatasa no Receptora Tipo 1/metabolismo , Proteína Tirosina Fosfatasa no Receptora Tipo 2/metabolismo , Teoría Cuántica , Terpenos/química , Terpenos/aislamiento & purificaciónRESUMEN
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.
Asunto(s)
Antibióticos Antineoplásicos/farmacología , Apoptosis/efectos de los fármacos , Lactamas Macrocíclicas/farmacología , Streptomyces/química , Antibióticos Antineoplásicos/química , Antibióticos Antineoplásicos/aislamiento & purificación , Línea Celular Tumoral , Cristalografía por Rayos X , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Lactamas Macrocíclicas/química , Lactamas Macrocíclicas/aislamiento & purificación , Estructura Molecular , HumedalesRESUMEN
Twelve undescribed compounds including six phenanthrene derivatives (parviphenanthrines A-F), two stilbene derivatives (parvistilbines A-B), three esters (parviesters A-C), and one sesquiterpenoid (parvidiol A) were isolated from the roots of Stemona parviflora, together with twenty-two known ones. The structures of the undescribed compounds were elucidated based on the analyses of their spectroscopic data. The absolute configuration of parviphenanthrine A was determined by the quantum ECD calculations. Parviphenanthrines A and E, stemanthrene A, stilbostenin E, 4-hydroxy-benzenepropanol-α-benzoate, and (E)-4-hydroxycinnamic acid methyl ester showed nematocidal activity against Meloidogyne incognita with IC50 values of 14.02⯱â¯0.32, 2.51⯱â¯0.13, 17.10⯱â¯0.65, 2.05⯱â¯0.07, 4.22⯱â¯0.31, and 1.07⯱â¯0.05⯵M, respectively.
Asunto(s)
Antinematodos/farmacología , Fitoquímicos/química , Extractos Vegetales/farmacología , Raíces de Plantas/química , Stemonaceae/química , Concentración 50 Inhibidora , Estructura MolecularRESUMEN
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.
Asunto(s)
Fusión Celular , Cordyceps/química , Cordyceps/citología , Acetilcolinesterasa , Animales , Antihelmínticos/química , Antihelmínticos/farmacología , Bioensayo , Inhibidores de la Colinesterasa/química , Inhibidores de la Colinesterasa/farmacología , Furanos/química , Furanos/metabolismo , Estructura Molecular , Nematodos/efectos de los fármacosRESUMEN
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.
Asunto(s)
Organismos Acuáticos/metabolismo , Aspergillus/metabolismo , Bacterias/efectos de los fármacos , Productos Biológicos/farmacología , Bivalvos/microbiología , Acetilcolinesterasa/química , Animales , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Antibacterianos/farmacología , Productos Biológicos/química , Productos Biológicos/aislamiento & purificación , Compuestos de Bifenilo/antagonistas & inhibidores , China , Inhibidores de la Colinesterasa/química , Inhibidores de la Colinesterasa/aislamiento & purificación , Inhibidores de la Colinesterasa/farmacología , Dicroismo Circular , Cristalografía por Rayos X , Depuradores de Radicales Libres/química , Depuradores de Radicales Libres/aislamiento & purificación , Depuradores de Radicales Libres/farmacología , Inhibidores de Glicósido Hidrolasas/química , Inhibidores de Glicósido Hidrolasas/aislamiento & purificación , Inhibidores de Glicósido Hidrolasas/farmacología , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Picratos/antagonistas & inhibidores , alfa-Glucosidasas/químicaRESUMEN
A new cytochalasin derivative xylarisin B (1), together with four known compounds astropyrone (2), guaidiol (3), xylaropyrone B (4), and xylaropyrone C (5), were isolated from the fermentation broth of Xylaria sp. HNWSW-2. Their structures were elucidated by spectroscopic data. Among them, compounds 2 and 3 at a concentration of 50 µg/ml showed weak inhibitory activity against AChE with inhibition rates of 10.4 and 12.9%, respectively. In addition, compound 2 also exhibited inhibitory activity against α-glycosidase with inhibition rate of 77.0% at a concentration of 0.25 mg/ml.
Asunto(s)
Citocalasinas/aislamiento & purificación , Endófitos/química , Xylariales/química , Inhibidores de la Colinesterasa/farmacología , Citocalasinas/química , Citocalasinas/farmacología , Fermentación , Inhibidores de Glicósido Hidrolasas/farmacología , Espectroscopía de Resonancia MagnéticaRESUMEN
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.