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1.
Bioorg Chem ; 109: 104716, 2021 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-33607362

RESUMO

Aiming to discover potent anti-proliferative agents from the roots of Sophora flavescens, seven new prenylated flavanones were isolated, along with 16 known compounds. Their structures were elucidated by interpretation of their spectroscopic data (1D and 2D NMR, UV, IR, CD, and HRESIMS) and comparison to literature data. In the in vitro assay, 21 showed anti-proliferative activity against human hepatoma cells (HepG2). Studies of its mechanism revealed that 21 could significantly activate autophagic flux and trigger ROS release in HepG2 cells. Western blot experiments demonstrated that 21 could activate the key signaling protein of autophagy and ROS, while it does not affect the main protein of the apoptosis signaling pathway. These results suggested that 21 mediates its anti-proliferative effects through autophagic cell death, which is apoptosis-independent.

2.
J Asian Nat Prod Res ; 23(3): 228-234, 2021 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-33459060

RESUMO

One pair of new amides enantiomers (1a and 1b) and two known amides were isolated from the rhizomes of Polygonum cuspidatum. Their structures were established using UV, IR, HRESIMS, and NMR data. Notably, compound 1 possesses unique C-C connection between feruloyltyramine and resveratrol. Their absolute configurations were determined by the ECD method. All compounds were evaluated for their α-glucosidase inhibitory activity and compounds 2 and 3 showed significant inhibitory activity with IC50 values of 2.82 and 13.06 µmol/L, respectively (positive control acarbose, IC50 385 µmol/L).


Assuntos
Fallopia japonica , Polygonum , Amidas/farmacologia , Estrutura Molecular , Extratos Vegetais , Rizoma
3.
J Asian Nat Prod Res ; : 1-7, 2020 Nov 24.
Artigo em Inglês | MEDLINE | ID: mdl-33231494

RESUMO

Three new monocyclic monoterpenoid containing ß-D-apiofuranosyl-(1→2)-O-ß-D-glucopyranosyl moieties, together with three other known monocyclic monoterpenoid O-glycosides, were obtained from the roots of Glycyrrhiza uralensis for the first time. Their structures were determined by UV, IR, HRESIMS, and 1D and 2D NMR data.

4.
J Asian Nat Prod Res ; 22(12): 1130-1137, 2020 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-33190510

RESUMO

Two new quinochalcone glycosides, hydroxysafflor yellow A-4'-O-ß-D-glucopyranoside (1) and 3'-hydroxyhydroxysafflor yellow A (2), were isolated from the safflower yellow pigments of Carthamus tinctorius. The structures of new compounds were elucidated by a detailed spectroscopic analysis (UV, IR, HR-ESI-MS, 1D and 2D NMR, ECD). The in vitro assay indicated that compound 1 could improve the survived rate of primary mouse cortical neurons on glutamate-induced neurons damage model at a concentration of 10 µM.


Assuntos
Carthamus tinctorius , Chalcona , Animais , Chalcona/análogos & derivados , Glicosídeos , Camundongos , Estrutura Molecular
5.
Org Biomol Chem ; 18(41): 8424-8432, 2020 Oct 28.
Artigo em Inglês | MEDLINE | ID: mdl-33112334

RESUMO

Eight new geranylquinol derivatives (1-8) were purified from the roots of Arnebia euchroma. Compounds 1-6 possess an unprecedented dearomatic benzocogeijerene skeleton with a rare trans-fused hydronaphthalene moiety. Their structures and absolute configurations were elucidated by HRESIMS, NMR, ECD, and X-ray diffraction. A convenient strategy for rapid determination of the relative configuration of H-1/H-7/Me-16 and the absolute configuration at C-1 for 1-6 was summarized. Compound 2 exhibited cytotoxicity against all the tested cell lines, namely PC9, BGC823, HCT116, HepG2, HeLa, and U87-MG, with IC50 values ranging from 13.7 to 29.3 µM.

6.
J Asian Nat Prod Res ; 22(10): 920-926, 2020 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-32820957

RESUMO

Phytochemical investigation of the rhizome of Ligusticum chuanxiong Hort led to the isolation and identification of three new compounds, chuanxiongoside A, (2E,4E)-8-(6-O-inositolyl)-8-oxo-2,7-dimethyl-octadienoic acid (2), chuanxiongoside C (3). The structures of these compounds were unambiguously established by HR-ESI-MS, UV, IR, CD, NMR spectral data and comparison to reported data. All the isolated compounds (1-3) were investigated for their inhibitory effects on nitric oxide (NO) production in LPS-induced RAW 264.7 cells. All compounds showed excellent inhibition of NO production stronger than curcumin. [Formula: see text].


Assuntos
Medicamentos de Ervas Chinesas , Ligusticum , Humanos , Inflamação , Estrutura Molecular , Rizoma
7.
J Asian Nat Prod Res ; 22(10): 935-940, 2020 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-32757770

RESUMO

Three new compounds named tanshinoic acid A (1), tanshinoic acid B (2), and tanshinoic acid C (3) were isolated from the rhizomes of Salvia miltiorrhiza, together with two known compounds methyl salvianolate A (4) and methyl salvianolate C (5). Their structures were determined on the basis of spectroscopic data (UV, IR, HRESIMS, 1 D and 2 D NMR). The in vitro assay indicated that 4 and 5 could improve the survived rate of cells on oxygen glucose deprivation (OGD) induced neurons damage model and glutamate-induced neurons damage model at a concentration of 10 µM. [Formula: see text].


Assuntos
Salvia miltiorrhiza , Abietanos , Estrutura Molecular , Raízes de Plantas , Rizoma
8.
J Asian Nat Prod Res ; 22(12): 1145-1151, 2020 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-32835515

RESUMO

Two new benzoic acid derivatives, sophophenoside A (1) and sophophenoside B (2), were isolated from Sophora flavescens. Their structures were elucidated by detailed spectroscopic analysis and chemical methods. Compounds 1 and 2 were assayed for their hepatoprotective activity on the cytotoxic effect of D-galactosamine on HL-7702 cells, and compound 1 exhibited a moderate hepatoprotective activity at a concentration of 10 µM.


Assuntos
Sophora , Ácido Benzoico , Glicosídeos/farmacologia , Estrutura Molecular , Raízes de Plantas
9.
Org Biomol Chem ; 18(28): 5453-5457, 2020 Jul 22.
Artigo em Inglês | MEDLINE | ID: mdl-32638801

RESUMO

Two pairs of unusual phthalide analog enantiomers, (+)- and (-)-neophathalides A and B [(+)- and (-)-1 and 2], were isolated from the rhizome of Ligusticum chuanxiong Hort. Notably, neophathalide A presented a novel spiro-[4.5]dec-6-ene skeleton that originated from an aldol condensation process from sedanonic acid. Neophathalide B is an unprecedented 3-substituted phthalide analog that possesses a four-membered lactone ring system. The structures of the compounds were established using UV, IR, HRESIMS, NMR and ECD methods. All of the compounds were evaluated for their hepatoprotective activity against N-acetyl-p-aminophenol-induced HepG2 cell injury. Compounds 1a, 1b, and 2a exhibited moderate hepatoprotective activity compared with the positive control drug bicyclol at a concentration of 10 µM (p < 0.01).

10.
Fitoterapia ; 146: 104673, 2020 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-32569676

RESUMO

Four new compounds including two new phenylpropanoid esters of sucrose, polygonusucroside A (1) and B (2); two new anthraquinones, 8-O-ß-d-(6'-galloyl)-glucopyranoside (3) and polyanthraquinoside A (4), together with six known compounds were isolated from Polygonum cuspidatum. Their structures were established using UV, IR, HRESIMS, and NMR data. All compounds were evaluated for their α-glucosidase inhibitory activities and neuroprotective effects. Compounds 5, 7 and 9 showed significant α-glucosidase inhibitory activities with IC50 values of 27.30, 5.51, and 1.09 µmol/L, respectively (acarbose as positive control, IC50 = 6.17 µmol/L). In addition, the assessment of neuroprotective effect showed that compound 3 exhibited remarkable effect against PC12 cells injured by serum-deprivation and compounds 2, 7, and 9 exhibited moderate effects against PC12 cells injured by rotenone.

11.
Bioorg Chem ; 101: 104016, 2020 08.
Artigo em Inglês | MEDLINE | ID: mdl-32599365

RESUMO

Ligusticum chuanxiong Hort is a famous health promoting plant cultivated in China, and widely consumed due to its various curative effects. To study the potential bioactive constituents from the rhizome of L. chuanxiong, a chemical investigation was thus performed. In present study, we report the isolation and identification of ten new compounds, including two coumarins (1-2), four lignans (3-6), and four phenols (7-10), along with five known compounds (11-15) from the rhizome of L. chuanxiong. The structures of these compounds were unambiguously established by HR-ESI-MS, UV, IR, CD, NMR spectral data and comparison to reported data. Meanwhile, the anti-inflammation and hepatoprotective activities of all these compounds were evaluated. The results show that compounds 5, 6 and 7 showed excellent inhibition of NO production in LPS-induced RAW 264.7 cells stronger than curcumin, and compounds 5, 7 and 9 exhibited greater hepatoprotective effect than that of bicyclol.

12.
J Asian Nat Prod Res ; 22(5): 418-424, 2020 May.
Artigo em Inglês | MEDLINE | ID: mdl-31538492

RESUMO

Two new lignans, wikstronoside B (1) and forsysesquinorlignan (2), were isolated from the fruits of Forsythia suspensa, along with two known sesquineolignans, hedyotol A and hedyotol C (3 and 4). The structures of new compounds were established via extensive spectroscopy techniques, including UV, IR, HRESIMS, NMR, and ECD. Compounds 3 and 4 were isolated from this plant for the first time. Their anti-inflammatory effects were evaluated via a detection model with LPS-induced murine macrophage RAW264.7 cells, and compound 3 showed a moderate activity.


Assuntos
Forsythia , Lignanas , Animais , Frutas , Camundongos , Estrutura Molecular , Extratos Vegetais
13.
J Asian Nat Prod Res ; 22(1): 24-29, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31368354

RESUMO

Two new naturally occurring products named salviamine G (1) and 4-methyl-9-(ethoxycarbonyl)-8-naphthoic acid (2) were isolated from the rhizomes of Salvia miltiorrhiza. Their structures were elucidated using spectroscopic data (UV, IR, HRESIMS, 1D and 2D NMR). Compounds 1 and 2 were screened for their inhibitory activity against HSV-1 and influenza A (H3N2) using acyclovir (ACV, IC50 = 0.67 µM) and oseltamivir (IC50 = 2.01 µM) as a positive control. Compound 1 exhibited moderate inhibitory activity against HSV-1 and influenza A (H3N2) with IC50 values of 11.11 and 8.62 µM, respectively.


Assuntos
Antivirais , Salvia miltiorrhiza , Salvia , Abietanos , Vírus da Influenza A Subtipo H3N2 , Estrutura Molecular , Rizoma
14.
J Asian Nat Prod Res ; 22(1): 17-23, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31389260

RESUMO

Two new isobenzofuranone derivatives, polyphthaliside A (1) and polyphthaliside B (2), and a new isocoumarin derivative, polyisocoumarin (3), were isolated from Polygonum cuspidatum. Their structures were elucidated by detailed spectroscopic analysis and chemical methods. The cytotoxicity activity and PTP1B inhibitory activity of compounds 1-3 were estimated and none of them exhibited activities at a concentration of 10 µM.


Assuntos
Fallopia japonica , Polygonum , Glicosídeos , Isocumarinas , Estrutura Molecular , Fenóis
15.
Bioorg Med Chem Lett ; 29(19): 126635, 2019 10 01.
Artigo em Inglês | MEDLINE | ID: mdl-31473042

RESUMO

Five new phenylpropanoid glycosides, susaroysides A-E (1-5) were isolated from the fruits of Forsythia suspensa. Their structures were elucidated by comprehensive spectroscopic data analysis. The absolute configurations of their sugars were determined by GC analysis. Notably, susaroysides A-D possessed a sugar with an unsubstituted anomeric carbon, which is relatively rare in natural sources. Compound 1 exhibited significant anti-inflammatory activity against the lipopolysaccharide (LPS)-induced tumor necrosis factor (TNF)-α expression in macrophage cells with the IC50 value of 1.053 µM.


Assuntos
Anti-Inflamatórios/farmacologia , Forsythia/química , Frutas/química , Glicosídeos/farmacologia , Macrófagos/efeitos dos fármacos , Extratos Vegetais/farmacologia , Fator de Necrose Tumoral alfa/metabolismo , Humanos , Lipopolissacarídeos/farmacologia , Macrófagos/citologia , Macrófagos/imunologia , Macrófagos/metabolismo , Fenóis/química , Propanóis/química
16.
Carbohydr Res ; 485: 107820, 2019 Nov 01.
Artigo em Inglês | MEDLINE | ID: mdl-31546144

RESUMO

As part of our ongoing investigation of the bioactive constituents from the roots of Glycyrrhiza uralensis Fisch., seven new flavonoid glycosides (1-7) were obtained along with 19 known compounds (8-26). All of the isolates possessed one or more sugar moieties. Their structures, as well as the absolute configurations, were elucidated on the basis of spectroscopic data (UV, IR, HRESIMS, 1D and 2D NMR, and CD). In the in vitro assay, compounds 3 and 7 showed moderate antioxidant activities at a concentration of 0.1 µM; compound 2 showed hepatoprotective activity at a concentration of 10 µM.


Assuntos
Antioxidantes/química , Antioxidantes/farmacologia , Flavonoides/química , Glicosídeos/química , Glicosídeos/farmacologia , Glycyrrhiza uralensis/química , Raízes de Plantas/química , Relação Dose-Resposta a Droga , Fígado/efeitos dos fármacos , Fígado/metabolismo
17.
Bioorg Chem ; 86: 679-685, 2019 05.
Artigo em Inglês | MEDLINE | ID: mdl-30831529

RESUMO

In the course of studying the components from the roots of Sophora flavescens, eight new unusual biflavonoids consisting of a flavanone fused with a dihydrochalcone skeleton were isolated. These new chemical structures were elucidated by means of UV, IR, HRESIMS, NMR and ECD spectroscopic data and a comparison of experimental ECD spectra with calculated ECD spectra. Some compounds were subjected to an antidiabetic bioassay on human recombinant PTP1B inhibition, and showed strong inhibitory activity.


Assuntos
Monoterpenos Acíclicos/farmacologia , Biflavonoides/farmacologia , Inibidores Enzimáticos/farmacologia , Extratos Vegetais/farmacologia , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Sophora/química , Monoterpenos Acíclicos/química , Monoterpenos Acíclicos/isolamento & purificação , Biflavonoides/química , Biflavonoides/isolamento & purificação , Chalconas/química , Chalconas/isolamento & purificação , Chalconas/farmacologia , Relação Dose-Resposta a Droga , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Humanos , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Raízes de Plantas/química , Proteína Tirosina Fosfatase não Receptora Tipo 1/metabolismo , Proteínas Recombinantes/metabolismo , Relação Estrutura-Atividade
18.
Fitoterapia ; 133: 186-192, 2019 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-30690123

RESUMO

Eight new triterpenoid saponins (1-8), were isolated from the roots of Glycyrrhiza uralensis Fisch., together with 10 known triterpenoid saponins (9-18). Their structures were determined by analysis of their spectroscopic data and comparison with the reference. All of the compounds were evaluated for their antioxidant effects in the in vitro assay. Compounds 2 and 8 showed significant antioxidant activities against Fe2+/cysteine-induced liver microsomal lipid peroxidation at 0.1 µM.


Assuntos
Antioxidantes/farmacologia , Glycyrrhiza uralensis/química , Saponinas/farmacologia , Triterpenos/farmacologia , Antioxidantes/isolamento & purificação , China , Peroxidação de Lipídeos , Microssomos Hepáticos/efeitos dos fármacos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Raízes de Plantas/química , Saponinas/isolamento & purificação , Triterpenos/isolamento & purificação
19.
Bioorg Chem ; 84: 505-510, 2019 03.
Artigo em Inglês | MEDLINE | ID: mdl-30602133

RESUMO

Seven new butylphthalide derivatives, ligusticumolide A-G (1-7), together with two known butylphthalide derivatives (8-9) were isolated from an ethanol extract of Ligusticum chuanxiong Hort. The structures of these derivatives were elucidated from analysis of 1D/2D NMR, UV, IR and HRESIMS data. The absolute configurations of these derivatives were determined by electronic circular dichroism (ECD) calculations and Mosher's method. Ligusticumolide A (1) and ligusticumolide B (2) are enantiomers that were obtained by chiral separation. Ligusticumolide C (3) and ligusticumolide D (4) are diastereomers. All of the compounds were evaluated for their hepatoprotective activity against N-acetyl-p-aminophenol-induced HepG2 cell injury. Compounds 4, 5, and 7-9 showed more significant hepatoprotective activity than that of the positive control drug (bicyclol) at a concentration of 10 µM (p < 0.01).


Assuntos
Benzofuranos/química , Ligusticum/química , Substâncias Protetoras/química , Benzofuranos/isolamento & purificação , Benzofuranos/farmacologia , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Dicroísmo Circular , Humanos , Ligusticum/metabolismo , Espectroscopia de Ressonância Magnética , Conformação Molecular , Raízes de Plantas/química , Raízes de Plantas/metabolismo , Substâncias Protetoras/isolamento & purificação , Substâncias Protetoras/farmacologia , Estereoisomerismo
20.
Bioorg Chem ; 82: 139-144, 2019 02.
Artigo em Inglês | MEDLINE | ID: mdl-30321776

RESUMO

Flower of Chrysanthemum morifolium is widely used in China and Japan as a folk medicine in treatment of many diseases. However, its active compounds remain largely unknown. In the present work, we have isolated, purified and characterized six new compounds (1-6), including two new arylnaphthalene lignans and four new phenolic glycosides, together with eight known compounds (7-14), from the flower of C. morifolium. Their structures and absolute configurations were elucidated in detail using 1D and 2D NMR, UV, IR, ORD, HRESIMS and ECD spectrometric data. In addition, compounds 1-3 possessed the significant neuroprotective activity against hydrogen peroxide-induced neurotoxicity in human neuroblastoma SH-SY5Y cells.


Assuntos
Catecóis/farmacologia , Chrysanthemum/química , Flores/química , Glucosídeos/farmacologia , Lignanas/farmacologia , Fármacos Neuroprotetores/farmacologia , Animais , Catecóis/química , Catecóis/isolamento & purificação , Linhagem Celular Tumoral , Glucosídeos/química , Glucosídeos/isolamento & purificação , Humanos , Peróxido de Hidrogênio/efeitos adversos , Lignanas/química , Lignanas/isolamento & purificação , Camundongos , Fármacos Neuroprotetores/química , Fármacos Neuroprotetores/isolamento & purificação , Estresse Oxidativo/efeitos dos fármacos , Células RAW 264.7
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