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1.
J Asian Nat Prod Res ; 23(9): 906-912, 2021 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-32744069

RESUMO

From the EtOH-soluble extract of the roots of Piper nigrum, one new dimeric alkamide, pipercyclobutanamide D (1) was isolated. Its structure was elucidated on the basis of NMR spectroscopic interpretation. The relative configuration of 1 was determined based on the NOESY analysis. Compound 1 showed α-glucosidase inhibitory activity with an IC50 value of 158.5 µM. In addition, compound 1 exhibited cytotoxicity against the MCF-7 and HepG2 cell lines with the IC50 values of 45.6 and 63.9 µM, respectively. Plausible biosynthetic pathway for the formation of 1 was proposed based on regioselective [2 + 2] cycloaddition reaction.


Assuntos
Alcaloides , Piper nigrum , Piper , Alcaloides/farmacologia , Estrutura Molecular , Extratos Vegetais , Raízes de Plantas
2.
Bioorg Med Chem Lett ; 30(17): 127359, 2020 09 01.
Artigo em Inglês | MEDLINE | ID: mdl-32738998

RESUMO

A series of novel N-substituted hydrazide derivatives were synthesized by reacting atranorin, a compound with a natural depside structure (1), with a range of hydrazines. The natural product and 12 new analogues (2-13) were investigated for inhibition of α-glucosidase. The N-substituted hydrazide derivatives showed more potent inhibition than the original. The experimental results were confirmed by docking analysis. This study suggests that these compounds are promising molecules for diabetes therapy. Molecular dynamics simulations were carried out with compound 2 demonstrating the best docking model using Gromac during simulation up to 20 ns to explore the stability of the complex ligand-protein. Furthermore, the activity of all synthetic compounds 2-13 against a normal cell line HEK293, used for assessing their cytotoxicity, was evaluated.


Assuntos
Inibidores de Glicosídeo Hidrolases/síntese química , Hidroxibenzoatos/química , Hipoglicemiantes/química , alfa-Glucosidases/metabolismo , Sítios de Ligação , Domínio Catalítico , Sobrevivência Celular/efeitos dos fármacos , Inibidores de Glicosídeo Hidrolases/metabolismo , Inibidores de Glicosídeo Hidrolases/farmacologia , Células HEK293 , Humanos , Hidrazinas/química , Hidroxibenzoatos/metabolismo , Hidroxibenzoatos/farmacologia , Hipoglicemiantes/metabolismo , Hipoglicemiantes/farmacologia , Conformação Molecular , Simulação de Acoplamento Molecular , Relação Estrutura-Atividade , alfa-Glucosidases/química
3.
Magn Reson Chem ; 51(7): 439-43, 2013 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-23681665

RESUMO

Tithonia tagetiflora Desv. (Asteraceae) is a widespread plant in Vietnam, and the species of Tithonia are known as plants containing many biologically active compounds. However, T. tagetiflora's chemical composition remains mostly unknown. Therefore, we now report the structural elucidation of two new sesquiterpene lactones, 8-angeloyloxy-2,14-epoxygermacra-4,10(1),11(13)-trien-6,12-olide (1) and 6-angeloyloxy-1-hydroxy-3,4-epoxygermacra-9,11(13)-dien-8,12-olide (2), together with three known compounds, including two norisoprenoids, (6S,9S)-vomifoliol or (6R,9R)-vomifoliol (3) and (6S,9S)-roseoside (4), and one glutinane type triterpene, epi-glutinol (5), from the leaves of T. tagetiflora. Their structures are established by 1D and 2D NMR spectroscopy, as well as ESI-MS analysis and comparison with literature data.


Assuntos
Asteraceae/química , Butanóis/química , Cicloexanonas/química , Glucosídeos/química , Lactonas/química , Norisoprenoides/química , Folhas de Planta/química , Sesquiterpenos/química , Espectroscopia de Ressonância Magnética , Extratos Vegetais/química , Vietnã
4.
Z Naturforsch C J Biosci ; 78(5-6): 247-251, 2023 May 25.
Artigo em Inglês | MEDLINE | ID: mdl-36544263

RESUMO

From the CHCl3-soluble extract of Annona muricata L. (Annonaceae) leaves, one new 3-benzazepine-type alkaloid, anonazepine (1), and four known aporphine-type alkaloids, (+)-laurotetanine (2), (+)-norglaucine (3), (-)-xylopine (4), and lanuginosine (5), were isolated. Except for (-)-xylopine (4), these remaining known alkaloids were first reported in A. muricata. The structures of the isolated alkaloids were established by 1D and 2D NMR spectroscopy and MS, as well as comparison with literature data. The new 3-benzazepine-type alkaloid existed in an inseparable mixture of two equilibrium conformers. Its absolute configuration was determined based on comparing their experimental and calculated ECD data. The anti-inflammatory activity of the isolated alkaloids was investigated, but none of the alkaloids showed a significant result.


Assuntos
Alcaloides , Annona , Annonaceae , Antineoplásicos , Annona/química , Alcaloides/farmacologia , Alcaloides/química , Extratos Vegetais/farmacologia , Extratos Vegetais/química
5.
Nat Prod Res ; 36(2): 553-559, 2022 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-32668989

RESUMO

From the ethyl acetate extract of the stems of Miliusa velutina, seven compounds (1-7) were isolated, including two new compounds such as mivelutina A acid (1), mivelutina B acid (2) and one known compound mivelutina B methyl ester (3). For this NMR data were not known previously. Their relative structures were elucidated based on NMR spectroscopic analysis. The absolute configuartions were determined based on DFT calculations of 13C chemical shifts. All of the seven compounds were screened for their in vitro cytotoxic activities against HepG2 cell line using the SRB assay. Epoxyconiferyl alcohol (7) showed the highest potential for the cytotoxicity of cancer cell lines HepG2 with the IC50 values of 95.94 µg/mL (527 µM).


Assuntos
Annonaceae , Antineoplásicos Fitogênicos , Sesquiterpenos , Antineoplásicos Fitogênicos/farmacologia , Células Hep G2 , Humanos , Estrutura Molecular , Sesquiterpenos/farmacologia
6.
Nat Prod Res ; 35(21): 3963-3969, 2021 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-32308029

RESUMO

Phytochemical study on the EtOAc-soluble extract of the leaves of Mimosa pigra led to the isolation of a new furanochromone, 6,8-dihydroxy-2-methyl-9H-furo[3,2-b]chromen-9-one (1), along with four known compounds (2-5). Their structures were elucidated based on the basis of the spectral interpretation. The plausible biosynthesis pathway for the formation of the new furanochromone was proposed. At a concentration of 100 µM, compound 1 showed no cytotoxicity against human MCF-7 breast cancer cell with a cell viability >50%.[Figure: see text].


Assuntos
Mimosa , Cromonas , Furanos , Humanos , Folhas de Planta
7.
Nat Prod Res ; 35(13): 2218-2223, 2021 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-31544512

RESUMO

From MeOH-soluble fraction of the flowers of Hibiscus sabdariffa (Malvaceae), one new lignan, (+)-4-O-methyl-5'-methoxy-secoisolariciresinol (1), together with four known compounds (2-5) were isolated. The structures were elucidated based on NMR spectroscopic analysis. The absolute configuration of 1 was determined based on the Cotton effects in the CD spectrum. Compounds 1, 3 and 4 showed antioxidant activities with the SC50 values of 56.9, 19.3 and 22.7 µM, respectively.


Assuntos
Flores/química , Hibiscus/química , Lignanas/isolamento & purificação , Compostos de Bifenilo/química , Sequestradores de Radicais Livres/química , Lignanas/química , Picratos/química
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