RESUMO
Ten undescribed cardiac glycosides, strasperosides A-J, together with twelve known analogues, were isolated from Streblus asper Lour. Their structures were elucidated on the basis of spectroscopic analysis, electronic circular dichroism data, and chemical methods. These cardiac glycosides showed diversity in steroid skeleton and sugar moiety. Strasperosides A and B are a pair of unusual stereoisomers featuring different orientation of the lactone motif. Ten cardiac glycosides demonstrated potent antiviral effects on HSV-1 in vitro with the IC50 values from 0.19 ± 0.08 to 1.03 ± 0.25 µM and the therapeutic indices from 66.61 ± 5.08 to 326.75 ± 11.75.
Assuntos
Glicosídeos Cardíacos , Moraceae , Glicosídeos Cardíacos/farmacologia , Glicosídeos Cardíacos/química , Extratos Vegetais/química , Moraceae/química , Antivirais/química , Glicosídeos/farmacologiaRESUMO
Three new formyl phloroglucinol meroterpenoids, eumaidials A-C (1-3), were isolated from the leaves of Eucalyptus globulus subsp. maidenii, along with ten known analogues (4-13). Their chemical structures were determined by various spectral data and electronic circular dichroism calculations. Eumaidial A (1) is the first ß-caryophyllene-based formyl phloroglucinol meroterpenoids from the genus Eucalyptus. Compounds 1-4 and 10 exhibited ATP-citrate lyase inhibitory activities, and compounds 2 and 3 suppressed the hepatocyte lipogenesis.
Assuntos
Eucalyptus , Complexos Multienzimáticos , Oxo-Ácido-Liases , Estrutura Molecular , Eucalyptus/química , Floroglucinol/farmacologia , Floroglucinol/química , Folhas de Planta/química , Trifosfato de AdenosinaRESUMO
Two new maytansinoids, N-methyltreflorine (1: ) and methyltrewiasine (2: ), were isolated from the dried fruits of Trewia nudiflora, together with three known congeners (3: â-â5: ). Their structures were elucidated by spectroscopic methods, and the absolute configuration of 1: and 2: was determined by X-ray crystallographic analysis. Compounds 1: â-â5: exhibited strong cytotoxicity against human tumor cell lines, including HeLa, MV-4â-â11, and MCF-7, with IC50 values ranging from 0.12 to 11 nM. Compounds 1: and 4: also showed inhibitory activity against the MCF-7/ADR cell line with IC50 values of 13 and 28 nM, respectively. Compounds 1: and 2: significantly inhibited tubulin polymerization in vitro with IC50 values of 3.6 and 3.2 µM, respectively.
Assuntos
Antineoplásicos , Tubulina (Proteína) , Antineoplásicos/farmacologia , Linhagem Celular Tumoral , Células HeLa , Humanos , Células MCF-7 , Estrutura Molecular , Tubulina (Proteína)/química , Tubulina (Proteína)/metabolismoRESUMO
Two new oleanane-triterpenoid saponins, clinograsaponins A (1) and B (2), together with twelve known ones (3-14), were isolated from the whole herb of Clinopodium gracile (Bentham) Matsumura. Their structures were determined by spectroscopic analysis and chemical method. All the isolated compounds were evaluated for their activities against ATP-citrate lyase (ACLY) and nuclear factor kappa B (NF-κB).
Assuntos
ATP Citrato (pro-S)-Liase/antagonistas & inibidores , Inibidores Enzimáticos/farmacologia , Lamiaceae/química , NF-kappa B/antagonistas & inibidores , Extratos Vegetais/farmacologia , ATP Citrato (pro-S)-Liase/metabolismo , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Conformação Molecular , NF-kappa B/metabolismo , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , EstereoisomerismoRESUMO
Three new polyprenylated acylphloroglucinol meroterpenoids, hyperiforins A-C (1-3), were isolated from Hypericum forrestii (Chittenden) N. Robson, together with twelve known analogues (4-15). Their structures were established by extensive physical and spectroscopic data analysis. Compounds 1, 2, 5, 7, and 13-15 showed potent inhibitory effects on protein tyrosine phosphatase 1B with IC50 values from 6.63 ± 2.40 to 14.21 ± 3.51 µM.
Assuntos
Hypericum/química , Floroglucinol/farmacologia , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Terpenos/farmacologia , China , Estrutura Molecular , Floroglucinol/isolamento & purificação , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Componentes Aéreos da Planta/química , Terpenos/isolamento & purificaçãoRESUMO
Hyperprins A (1) and B (2), two polyprenylated acylphloroglucinol related meroterpenoids with undescribed carbon skeletons, were isolated from Hypericum przewalskii. Compound 1 possesses a new 6/6/6/6/5/5 hexacyclic system with an unprecedented tetracyclo[10.3.1.03,8.08,12]hexadecane motif. Compound 2 features a unique 6/8/6/6 tetracyclic scaffold. Their structures were determined by spectroscopic data, chemical method, and X-ray crystallography. Compound 1 showed antiproliferation activity against the MV-4-11 cell line, and the p-bromobenzoate derivative of 2 displayed PTP1B inhibition.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Inibidores Enzimáticos/farmacologia , Hypericum/química , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Humanos , Conformação Molecular , Proteína Tirosina Fosfatase não Receptora Tipo 1/metabolismo , EstereoisomerismoRESUMO
Five pairs of optically pure meroterpenoid enantiomers (1a/1b-5a/5b) and two known compounds (6 and 7) were isolated from Rhododendron fastigiatum. Compounds 1a/1b-5a/5b were resolved from naturally scalemic mixtures by chiral HPLC. Their structures were elucidated by spectroscopic methods, X-ray crystallographic experiments, and ECD analyses. Compounds 1a/1b, 2a/2b, 3b, 4a/4b, and 5a/5b were new meroterpenoids with different polycyclic systems. Two enantiomeric pairs (2a/2b and 3a/3b), 6, and 7 exhibited inhibitory effects on protein tyrosine phosphatase 1B (PTP1B) in vitro.
Assuntos
Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Rhododendron/química , Terpenos/química , Terpenos/isolamento & purificação , China , Cromatografia Líquida de Alta Pressão , Cristalografia por Raios X , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Componentes Aéreos da Planta/químicaRESUMO
Six new triterpenoids, pseudolarins A-F (1-6), were isolated from the twigs of Pseudolarix amabilis, together with four known triterpenoids (7-10) and five known diterpenoids (11-15). Their structures were determined by extensive spectroscopic analysis, and the absolute configuration of 1 was assigned by single-crystal X-ray diffraction. Compound 1 is a 3,4:9,10-diseco-cycloartane triterpenoid possessing an unprecedented 5/5/7/6/5/6/5 ring system. Compounds 1, 5, 7, 9-11, and 13 showed inhibition against protein tyrosine phosphatase 1B (PTP1B) in vitro.
Assuntos
Diterpenos/farmacologia , Pinaceae/química , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Triterpenos/farmacologia , China , Diterpenos/isolamento & purificação , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Triterpenos/isolamento & purificaçãoRESUMO
Twelve alkaloids were isolated from the bulbs of Fritillaria yuminensis by column chromatography over silica gel, ODS, and Sephadex LH-20, as well as RP-HPLC. Their structures were identified mainly by NMR and MS analyses as yubeinine(1), imperialine(2), delavinone(3), tortifoline(4), hupehenizioiside(5), imperialine-ß-D-glucoside(6), kuroyurinidine(7), pengbeisine A(8), walujewine A(9), peimisine-3-O-ß-D-glucopyranoside(10), solanidine-3-O-α-L-rhamnopyranosyl-(1â2)-ß-D-glucopyranoside(11), and solanidine-3-O-α-L-rhamnopyranosyl-(1â2)-[ß-D-glucopyranosyl-(1â4)]-ß-D-glucopyranoside(12). Compounds 4-12 were obtained from F. yuminensis for the first time.
Assuntos
Alcaloides/análise , Fritillaria/química , Raízes de Plantas/química , Cromatografia Líquida de Alta Pressão , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Compostos Fitoquímicos/análiseRESUMO
Eleven flavonoids were isolated from the twigs of Broussonetia papyrifera by column chromatography over silica gel,ODS,MCI gel,and Sephadex LH-20,as well as RP-HPLC.Their structures were identified by spectroscopic methods including NMR,MS,UV,and IR as broupapyrin A(1),5,7,3',4'-tetrahydroxy-3-methoxy-8-geranylflavone(2),8-prenylquercetin-3-methyl ether(3),broussonol D(4),broussoflavonol B(5),uralenol(6),broussonol E(7),8-(1,1-dimethylallyl)-5'-(3-methylbut-2-enyl)-3',4',5,7-tetrahydroxyflanvonol(8),broussoflavonol E(9),4,2',4'-trihydroxychalcone(10),and butein(11).Compound 1 is a new isoprenylated flavonol.Compounds 3,6,10,and 11 were obtained from the genus Broussonetia for the first time,and 4 and 7 were firstly discovered in B.papyrifera.Compounds 1-5 and 7-9 showed significant inhibitory effects on PTP1 B with IC50 values ranging from(0.83±0.30) to(4.66±0.83) µmol·L-1.
Assuntos
Broussonetia/química , Flavonoides/farmacologia , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Cromatografia Líquida de Alta Pressão , Flavonoides/isolamento & purificação , Espectroscopia de Ressonância Magnética , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologiaRESUMO
Three new isosteroidal alkaloids, frititorines A-C (1-3), were isolated from the bulbs of Fritillaria tortifolia, together with ten known ones (4-13). Their structures were elucidated by extensive spectroscopic analyses, chemical methods, and single-crystal X-ray crystallographic analysis. Compound 1 is the first 5ß-cevanine alkaloid with a cis A/B ring junction from the Fritillaria genus. Compound 2 is the first example of glycosylated isosteroidal alkaloid N-oxide. Compound 1 showed significant relaxant effect on Ach-induced tracheal contraction with pA2 and EC50 values equivalent to those of aminophylline.
Assuntos
Alcaloides/isolamento & purificação , Fritillaria/química , Raízes de Plantas/química , Traqueia/efeitos dos fármacos , Animais , China , Técnicas In Vitro , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Ratos Sprague-DawleyRESUMO
Three new (1a/1b and 2b) and five known flavans (2a, 6a/6b, 7, and 8), one new flavan glycoside (3), and two new (4 and 5) and six known 1,3-diphenylpropanes (9-14) were isolated from the twigs of Broussonetia kazinoki. Compounds 1, 2, and 6 are scalemic mixtures, and were resolved by chiral HPLC to provide 1a/1b, 2a/2b, and 6a/6b. The structures of these compounds were elucidated by extensive spectroscopic methods, including NMR, MS, and ECD analyses. Compounds 1, 2, 5, 8, 9, 11, and 12 showed in vitro inhibition of protein tyrosine phosphatase 1B (PTP1B).
Assuntos
Broussonetia/química , Flavonoides/isolamento & purificação , Glicosídeos/isolamento & purificação , Compostos Fitoquímicos/isolamento & purificação , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , China , Flavonoides/farmacologia , Glicosídeos/farmacologia , Estrutura Molecular , Compostos Fitoquímicos/farmacologia , Relação Estrutura-AtividadeRESUMO
PPARγ agonists are widely used medications in diabetes mellitus therapy. Their role in improving adipose tissue function contributes to antidiabetic effects. The extracts of Dodonaea viscosa have been reported to exert antidiabetic activity. However, the effective mediators and the underlying mechanisms were largely unknown. In this study, we investigated the action on PPARγ transactivation and adipocyte modulation of two typical flavonoid constituents from D. viscosa, 5,4'-dihydroxy-7,8-dimethoxyflavanone and aliarin. Our results showed that 5,4'-dihydroxy-7,8-dimethoxyflavanone and aliarin were potential partial PPARγ agonists. The compounds induced adipogenesis in 3T3-L1 cells, with an upregulated adiponectin mRNA level and enhanced insulin sensitivity. The favorable effects of 5,4'-dihydroxy-7,8-dimethoxyflavanone, aliarin, and other flavonoid constituents on adipocytes might contribute to the antidiabetic efficacy of D. viscosa.
Assuntos
Diabetes Mellitus/tratamento farmacológico , Flavanonas/farmacologia , Flavonoides/farmacologia , Hipoglicemiantes/agonistas , PPAR gama/agonistas , Sapindaceae/química , Células 3T3-L1 , Adipócitos/efeitos dos fármacos , Adipogenia/efeitos dos fármacos , Adiponectina/genética , Tecido Adiposo/efeitos dos fármacos , Animais , Flavanonas/química , Flavanonas/isolamento & purificação , Flavonoides/química , Flavonoides/isolamento & purificação , Hipoglicemiantes/uso terapêutico , Resistência à Insulina , Camundongos , PPAR gama/uso terapêutico , Regulação para CimaRESUMO
Two new Diels-Alder adducts, albasins A and B (1 and 2), one new isoprenylated 2-arylbenzofuran, albasin C (3), one new isoprenylated flavone, albasin D (4), together with sixteen known phenolic compounds, were isolated from the root bark of Morus alba. Their structures were elucidated by extensive spectroscopic analysis, including NMR, MS, and ECD data. All the new compounds and most of the known ones showed significant inhibitory effects on PTP1B in vitro with IC50 values ranging from 0.57 to 7.49µM.
Assuntos
Inibidores Enzimáticos/química , Morus/química , Fenóis/química , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Benzofuranos/química , Benzofuranos/isolamento & purificação , Inibidores Enzimáticos/isolamento & purificação , Flavonas/química , Flavonas/isolamento & purificação , Humanos , Estrutura Molecular , Fenóis/isolamento & purificação , Casca de Planta/química , Raízes de Plantas/química , PrenilaçãoRESUMO
Two new isoprenylated flavonoids, laevigasins A and B (1 and 2, resp.), and one new isoprenylated 2-arylbenzofuran, leavigasin C (3), together with eight known compounds, 4-11, were isolated from the twigs of Morus laevigata. Their structures were elucidated by spectroscopic methods. Laevigasin A (1) showed significant inhibitory effect on α-glucosidase in vitro. Notabilisin E (5), taxifolin (10), and hultenin (11) inhibited PTP1B phosphatase activity in vitro.
Assuntos
Morus/química , Fenóis/isolamento & purificação , Extratos Vegetais/isolamento & purificação , Estrutura Molecular , Fenóis/química , Extratos Vegetais/químicaRESUMO
(2'R)-2',3'-Dihydro-2'-(1-hydroxy-1-methylethyl)-2,6'-bibenzofuran-6,4'-diol (DHMB) is a natural compound extracted from Morus notabilis. It was found that DHMB acts as a competitive inhibitor against mushroom tyrosinase with a Ki value of 14.77 µM. Docking results further indicated that it could form strong interactions with one copper ion with a distance of 2.7 Å, suggesting the mechanism of inhibition might be due to chelating copper ions in the active site. Furthermore, melanin production in B16-F10 murine melanoma cells was significantly inhibited by DHMB in a concentration-dependent manner without cytotoxicity. The results of western blotting also showed that DHMB decreased 3-isobuty-1-methxlzanthine-induced mature tyrosinase expression. Taken together, these findings indicated that DHMB may be a new promising pigmentation-altering agent for agriculture, cosmetic, and therapeutic applications.
Assuntos
Agaricales/enzimologia , Benzofuranos/química , Melaninas/biossíntese , Melanoma Experimental/metabolismo , Monofenol Mono-Oxigenase/antagonistas & inibidores , Animais , Linhagem Celular Tumoral , AMP Cíclico/metabolismo , Inibidores Enzimáticos/química , Camundongos , Simulação de Acoplamento Molecular , Morus/químicaRESUMO
Two new isoprenylated flavanones, ficustikousins A and B (1 and 2), together with seven known compounds (3-9) were isolated from the whole plant of Ficus tikoua (Moraceae). The structures of the new compounds were elucidated on the basis of spectroscopic methods. Compounds 1-7 exhibited moderate inhibitory activities against PTP1B in vitro.
Assuntos
Ficus/química , Flavonoides/química , Flavonoides/farmacologia , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Concentração Inibidora 50RESUMO
Thirteen triterpenoids (1-13), including two new lupane triterpenoids, salacinins A and B (1 and 2), as well as one new friedelane triterpenoid, salacinin C (3), were isolated from the roots and stems of Salacia hainanensis. The structures of new compounds were elucidated by extensive spectroscopic analysis including 1D and 2D NMR, and MS experiments. Compound 1 possesses rare 2,3-seco-lupane skeleton. Compounds 4, 6 and 7 showed inhibitory effects on α-glucosidase in vitro.
Assuntos
Inibidores de Glicosídeo Hidrolases/química , Salacia/química , Salacia/metabolismo , Triterpenos/química , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Estrutura Molecular , Raízes de Plantas/química , Caules de Planta/química , Triterpenos/isolamento & purificação , alfa-GlucosidasesRESUMO
Eight phenolic compounds were isolated from Rhododendron phaeochrysum var. agglutinatum and their sructures were identified as phaeochrysin (1), (2R)-4-(3',4'-dihydroxyphenyl) -2-butanol (2), (-) -rhododendrol (3), rhododendrin (4), (+) -isolariciresinol (5), (-) -lyoniresinol (6), lyoniresinol-9'-O-ß-D-xylopyranoside (7), and dihydrodehydrodiconiferyl-3a-O-α-L-rhamnopyranoside (8). Compound 1 is new, and compounds 2, 5-8 were isolated from this plant for the first time.
Assuntos
Medicamentos de Ervas Chinesas/química , Fenóis/química , Rhododendron/química , Espectrometria de Massas , Estrutura MolecularRESUMO
Phytochemical investigation of the stem of Morus notabilis led to the isolation and characterization of 10 compounds of 2-arylbenzofurans (1-10), including two new compounds, (2'R)-2',3'-dihydro-2'-(1-hydroxy-1-methylethyl)-2,6'-bibenzofuran-6,4'-diol (1) and 5,6-dimethoxy-2-(3-hydroxy-5-methoxyphenyl)benzofuran (2). Moracins O (6) and P (10) showed inhibitory effects on mushroom tyrosinase with IC50 values being lower than that of kojic acid.