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1.
Chem Biodivers ; 21(5): e202400414, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38500337

RESUMO

Three undescribed sesquiterpenes (1-3), two enantiomeric pairs of monoterpenes (4a/4b-5a/5b), one alkyne (6), two known alkynes (7-8) and eight known coumarins (9-16) were isolated from the aerial parts extracts of Artemisia scoparia. The structures of these compounds were fully elucidated by their 1D and 2D NMR, HRESIMS spectral data analyses, and comparison with literature. The absolute configurations of compounds were determined by single-crystal X-ray crystallography (1), a comparison of experimental and calculated electronic circular dichroism (ECD) data (2-6). 15 showed moderate inhibitory activity with the NO release in LPS-induced RAW264.7 cells. 9-16 showed varying degrees of promoting melanogenesis and tyrosinase activity in B16 cells.


Assuntos
Artemisia , Óxido Nítrico , Artemisia/química , Camundongos , Animais , Células RAW 264.7 , Óxido Nítrico/antagonistas & inibidores , Óxido Nítrico/biossíntese , Óxido Nítrico/metabolismo , Monofenol Mono-Oxigenase/antagonistas & inibidores , Monofenol Mono-Oxigenase/metabolismo , Lipopolissacarídeos/antagonistas & inibidores , Lipopolissacarídeos/farmacologia , Cristalografia por Raios X , Componentes Aéreos da Planta/química , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Sesquiterpenos/isolamento & purificação , Estrutura Molecular , Monoterpenos/química , Monoterpenos/isolamento & purificação , Monoterpenos/farmacologia , Cumarínicos/química , Cumarínicos/farmacologia , Cumarínicos/isolamento & purificação , Conformação Molecular , Melaninas/antagonistas & inibidores , Melaninas/metabolismo , Modelos Moleculares , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Extratos Vegetais/isolamento & purificação
2.
Chem Biodivers ; 20(3): e202200936, 2023 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-36696143

RESUMO

Shawurenine C (1a) and D (1b), a new pair of regioisomeric C19 -diterpenoid alkaloids, and five known C19 -diterpenoid alkaloids (2-6) were isolated from the aerial part of Delphinium shawurense W. T. Wang. The chemical structures of new compounds were established based on spectroscopic analyses: HR-ESI-MS, and 1D, 2D NMR spectroscopic data. The anti-inflammatory and cytotoxic activities of these diterpenoid alkaloids were also evaluated.


Assuntos
Alcaloides , Delphinium , Diterpenos , Delphinium/química , Estrutura Molecular , Espectroscopia de Ressonância Magnética , Alcaloides/farmacologia , Alcaloides/química , Diterpenos/farmacologia , Diterpenos/química
3.
Nat Prod Res ; 35(5): 796-801, 2021 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-30966796

RESUMO

Five indole derivatives, 1H-indol-7-ol (1), tryptophol (2), 3-indolepropionic acid (3), tryptophan (4), 3,3-di(1H-indol-3-yl)propane-1,2-diol (5) and two diketopiperazines, cyclo(L-Pro-L-Tyr) (6), cyclo[L-(4-hydroxyprolinyl)-L-leucine (7) along with one dihydrocinnamic acid (8) were isolated from Pantoea ananatis VERA8, that endophytic bacteria derived from Baccharoides anthelmintica roots. This is a first report towards an isolation of endophytic strains (funji or bacteria) from the B. anthelmintica herb. The synergetic properties of the total extract compositions, as well as effects of the pure isolated secondary metabolites evaluated on their melanin synthesis in murine B16 cells towards for vitiligo treatment.


Assuntos
Asteraceae/microbiologia , Endófitos/metabolismo , Melaninas/biossíntese , Melanoma Experimental/patologia , Pantoea/metabolismo , Raízes de Plantas/microbiologia , Metabolismo Secundário , Animais , Linhagem Celular Tumoral , Endófitos/isolamento & purificação , Camundongos , Pantoea/isolamento & purificação , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia
4.
Nat Prod Res ; 34(12): 1772-1776, 2020 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-30499349

RESUMO

Seventeen compounds were isolated from the capitula of Coreopsis tinctoria Nutt. with various column chromatographic methods and semi-preparative HPLC. Their structures were identified by the spectroscopic data and comparison with literatures as 2'-hydroxy-4,4'-dimethoxy-chalcone; (1), isoliquiritigenin (2), eriodictyol (3), naringenin (4), maritimetin (5), butin (6), taxifolin (7), luteolin (8), 7,3',4'-trihydroxyflavone (9), 8,3',4'-trihydroxyflavone-7-O-ß-d-glucoside (10), quercetin (11), quercetagitin-7-O-ß-d-glucoside (12), quercetin-7-O-ß-d-glucoside (13), 3,4-dihydroxybenzoic acid (14), caffeic acid (15), coreoside B (16), and myo-inositol (17). Compounds 1, 4, 9, 10 and 17 were isolated from C. tinctoria Nutt. for the first time. Compounds 7 and 12 possessed the highest antioxidant activity (IC50 = 64.37 and 32.86 µg/ml, respectively) among the tested compounds (IC50 value of positive control was 5.34 µg/ml). Compound 7 exhibited potent PTP1B enzymatic inhibition with an IC50 value of 7.73 µg/ml (IC50 value of positive control is 1.46 µg/ml). Furthermore, compound 5 showed strong antibacterial activity against the Gram-positive bacterium, S. aureus.


Assuntos
Antibacterianos/isolamento & purificação , Antioxidantes/isolamento & purificação , Coreopsis/química , Hipoglicemiantes/isolamento & purificação , Antibacterianos/química , Antibacterianos/farmacologia , Antioxidantes/química , Antioxidantes/farmacologia , Flavonoides/isolamento & purificação , Glucosídeos/isolamento & purificação , Hipoglicemiantes/química , Hipoglicemiantes/farmacologia , Estrutura Molecular , Extratos Vegetais/química , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Staphylococcus aureus/efeitos dos fármacos
5.
Nat Prod Res ; 32(19): 2325-2332, 2018 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-29224384

RESUMO

The new coumarin 1, yuganin A (7-methoxy-8-((1S,2S)-1,2,3-trihydroxy-3-methylbutyl)-2H-chromen-2-one) along with nine known coumarins, heraclenol 3'-O-ß-D-glucopyranoside (2), oxypeucedanin hydrate 3'-O-ß-D-glucopyranoside (3), heraclenol (4), oxypeucedanin hydrate (5), osthole (6), oxypeucedanin (7), heraclenin (8), isoimperatorin (9), imperatorin (10) and the disaccharide sucrose (11), have been isolated from the roots of Prangos pabularia, and the structures of these isolated compounds were elucidated by spectroscopic means, especially, UV, HR-ESIMS, and 1D and 2D NMR spectroscopy. Furthermore, the anti-melanogenic effect of yuganin A and its inhibitory effect on B16 cells were evaluated. Yuganin A may be useful in the treatment of hyperpigmentation and as a skin-whitening agent in the cosmetics industry.


Assuntos
Apiaceae/química , Cumarínicos/isolamento & purificação , Raízes de Plantas , Animais , Antineoplásicos/química , Linhagem Celular Tumoral , Cosméticos , Cumarínicos/química , Indóis/antagonistas & inibidores , Camundongos , Estrutura Molecular , Extratos Vegetais/química , Raízes de Plantas/química , Análise Espectral
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