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1.
Fitoterapia ; 175: 105945, 2024 Apr 02.
Artículo en Inglés | MEDLINE | ID: mdl-38575091

RESUMEN

Four previously undescribed isoprenoid flavonoids (2-5) were isolated from Sophora davidii, along with five known analogues. The structures of the compounds were established through comprehensive analysis of spectroscopic data, including HRESIMS, 1D and 2D NMR, and absolute configurations determined by theoretical calculations, including ECD and NMR calculation. The cytotoxic effects of the isolated compounds on human HT29 colon cancer cells were evaluated using the MTT assay, compound 1 exhibited cytotoxicity against human HT29 colon cancer cells with an IC50 value of 8.39 ± 0.09 µM. Studies conducted with compound 1 in HT29 cells demonstrated that it may induce apoptosis and autophagy in HT29 by promoting the phosphorylation of P38 MAPK and inhibiting the phosphorylation of Erk MAPK.

2.
Magn Reson Chem ; 61(8): 481-486, 2023 08.
Artículo en Inglés | MEDLINE | ID: mdl-37227105

RESUMEN

Six lactone derivatives, including four α-pyrones derivatives (1-4), two α-furanone derivatives (5 and 6), were isolated from the Dendrobium pendulum. Structural elucidation of these undescribed lactone derivatives were accomplished on the basis of detailed nuclear magnetic resonance analysis, and the absolute configurations of compounds 1-4 were confirmed by electronic circular dichroism (ECD) techniques. The cytotoxic effects of isolated compounds on human breast cancer cell MDA-MB-231 were evaluated by the MTT assay.


Asunto(s)
Antineoplásicos , Dendrobium , Humanos , Estructura Molecular , Lactonas/farmacología , Lactonas/química , Dendrobium/química , Espectroscopía de Resonancia Magnética
3.
Magn Reson Chem ; 61(6): 386-391, 2023 06.
Artículo en Inglés | MEDLINE | ID: mdl-36929032

RESUMEN

Two new sesquiterpenoids, dendroaduoid A (1) and dendroaduol (2), together with four known sesquiterpenoids were isolated from the stems of Dendrobium aduncum. Their structures were identified by HR-ESI-MS and NMR experiments, and the complete assignments of 1 H and 13 C NMR data for two new sesquiterpenoids were obtained by the aid of HSQC, HMBC, 1 H-1 H COSY, NOESY, and ECD techniques. The cytotoxic effects of the isolated compounds on four tumor cell lines (HCT-116, HepG2, A549, and SW1990) were evaluated using MTT assay. Otherwise, the inhibitory activity of these six sesquiterpenoids on glycosidase was also evaluated.


Asunto(s)
Dendrobium , Sesquiterpenos , Línea Celular Tumoral , Sesquiterpenos/farmacología
4.
Nat Prod Res ; 37(14): 2375-2382, 2023 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-35245427

RESUMEN

Two previously undescribed dihydrophenanthrene derivatives (1 and 2) were isolated along with twelve known analogues from the whole plant of Dendrobium terminale. The structures of the new compounds were elucidated on the basis of detailed spectroscopic analysis. The NMR data of known phenanthrene derivatives (7 and 9) were revised by 2D NMR. The isolated compounds were evaluated for cytotoxicity against three kinds of tumor cell lines (sw1990, HCT-116, and HepG2). Especially compounds 11 and 14 showed stronger antitumor effects, and the structure-activity relationship of these compounds was discussed.


Asunto(s)
Dendrobium , Fenantrenos , Dendrobium/química , Fenantrenos/farmacología , Fenantrenos/química , Extractos Vegetales/química , Espectroscopía de Resonancia Magnética , Línea Celular Tumoral , Estructura Molecular
5.
Fitoterapia ; 160: 105220, 2022 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-35589060

RESUMEN

Four previously undescribed compounds, including three glucosyloxybenzyl 2-isobutylmalates (1-3), one phenolic glycoside (4), along with ten known compounds were isolated from the flowers of Bletilla striata. The structures and absolute configurations of the undescribed compounds were elucidated on the basis of HR-ESIMS, NMR spectroscopy, optical rotation value, and acid hydrolysis experiment. Cytotoxicity of the isolated compounds against A549, HCT-116, and SW1990 cells and protective effects of t-BHP-induced L02 cytotoxic were assayed. The antioxidant activities of the isolated compounds were also evaluated.


Asunto(s)
Glicósidos , Orchidaceae , Flores , Estructura Molecular , Orchidaceae/química , Fenoles/química
6.
Nat Prod Res ; 36(21): 5393-5399, 2022 Nov.
Artículo en Inglés | MEDLINE | ID: mdl-34930072

RESUMEN

Six dendrobine-type alkaloids were isolated from the tubes of Dendrobium nobile by silica gel, Sephadex LH-20 gel column chromatography, and preparative HPLC. Compound 1 is a new alkaloid containing a pair of amide tautomers, whereas compound 2 is a new dendrobine-type alkaloid. By using spectroscopic techniques including 1 D and 2 D NMR, the structures of compounds 1‒6 were identified as N-methoxylcarbonyldendrobine (1), dendronboic acid (2), dendrobine (3), 6-hydroxyldendrobine (4), dendrobine N-oxide (5), and denrine (6). The cytotoxic effects of the isolated compounds on two human tumour cell lines (HCT-116 and SW1990) were evaluated using MTT assay.


Asunto(s)
Alcaloides , Dendrobium , Humanos , Dendrobium/química , Alcaloides/química , Línea Celular Tumoral , Cromatografía Líquida de Alta Presión
7.
J Asian Nat Prod Res ; 23(12): 1204-1209, 2021 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-33502258

RESUMEN

A new lanostane triterpenoid (1) and two known (2, 3) analogues were isolated from Nothotsuga longibracteata. Their chemical structures were identified by spectral data including HR-ESI-MS, 1 D, and 2 D NMR. These lanostane triterpenoids showed no cytotoxic activities against three human tumour cell lines (A172, SHSY5Y, and Hela), but exhibited the activity of promoting the gastrointestinal motility of zebrafish treated with Nile red.


Asunto(s)
Ganoderma , Triterpenos , Animales , Línea Celular Tumoral , Humanos , Estructura Molecular , Triterpenos/farmacología , Pez Cebra
8.
Fitoterapia ; 143: 104586, 2020 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-32247772

RESUMEN

Two new dihydrophenanthrofurans (1 and 2) and two new bisbibenzyl derivatives (3 and 4) were isolated from the traditional Chinese medicinal plant Dendrobium nobile, along with four known compounds (5-8). The absolute configurations of compounds 1 and 4 were elucidated through extensive NMR and ECD spectroscopic analyses. New compounds showed no antimicrobial activity against four gram-positive bacterial strains and four gram-negative bacteria at the concentration of 1 mg/mL, but displayed significant cytotoxic activity against HepG2 human hepatic cell line with the IC50 values ranging from 1.25 µM to 19.47 µM.


Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Dendrobium/química , Furanos/farmacología , Fenantrenos/farmacología , Tallos de la Planta/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Furanos/aislamiento & purificación , Bacterias Gramnegativas , Bacterias Grampositivas , Células Hep G2 , Humanos , Estructura Molecular , Fenantrenos/aislamiento & purificación , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Plantas Medicinales/química
9.
Fitoterapia ; 142: 104497, 2020 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-32058054

RESUMEN

Five previously undescribed compounds, including two dendrobine-type alkaloids (1 and 2), three bibenzyl derivatives (3-5), along with six known compounds were isolated from orchids Dendrobium findlayanum. The structures and absolute configurations of the undescribed compounds were elucidated on the basis of HR-ESIMS, NMR spectroscopy, optical rotation value, as well as electronic circular dichroism (ECD) calculations. The cytotoxic effects of the isolated compounds on three human tumour cell lines (A172, SHSY5Y, and Hela) were evaluated by the MTT assay. Compound 6 showed excellent inhibitory activities against three human tumour cell lines with IC50 ranging from 1.65 µM to 3.77 µM. All these compounds were assessed for their activity of promoting the gastrointestinal motility of zebrafish treated with Nile red. Compound 6 have excellent activity to promote the gastrointestinal motility of zebrafish at the concentration of 0.3 µM.


Asunto(s)
Alcaloides/química , Bibencilos/química , Dendrobium/química , Alcaloides/aislamiento & purificación , Animales , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Bibencilos/aislamiento & purificación , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Fármacos Gastrointestinales/química , Fármacos Gastrointestinales/farmacología , Motilidad Gastrointestinal/efectos de los fármacos , Humanos , Larva/efectos de los fármacos , Modelos Moleculares , Estructura Molecular , Pez Cebra
10.
Nat Prod Res ; 34(3): 329-334, 2020 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-30587031

RESUMEN

A new dibenzocyclooctdiene (1), and a new eupodienone (2) type lignans were isolated along with five known analogues from the whole plant of Gymnotheca involucrata Pei. The structures of the new compounds were elucidated on the basis of detailed spectroscopic analysis. Bioassay results showed that compounds 1 and 2 exhibited no antimicrobial activity against four Gram-positive bacterial strains and four Gram-negative bacteria at the concentration of 1 mg/mL.


Asunto(s)
Lignanos/aislamiento & purificación , Saururaceae/química , Bacterias Gramnegativas/efectos de los fármacos , Bacterias Grampositivas/efectos de los fármacos , Lignanos/química , Estructura Molecular , Análisis Espectral/métodos
11.
J Asian Nat Prod Res ; 21(12): 1184-1189, 2019 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-30612468

RESUMEN

A new triphenanthrene compound named 2,2',2'',7,7',7''-hexahydroxy-4,4',4''-trimethoxy-[9,9',9'',10,10',10'']-hexahydro-1,8,1',6''-triphenanthrene (1), together with eleven known compounds (2-12), were isolated from tubers of Bletilla striata. Their structures were determined by analysis of spectroscopic data.


Asunto(s)
Orchidaceae , Estructura Molecular , Tubérculos de la Planta
12.
Molecules ; 23(7)2018 Jun 26.
Artículo en Inglés | MEDLINE | ID: mdl-29949909

RESUMEN

A novel isoquinoline alkaloid, mahimbrine A, possessing a rare benzotropolone framing scaffold, was isolated from the endemic plant of Mahonia imbricata. Its structure was established on the basis of extensive spectroscopic analysis. A plausible biosynthetic route of mahimbrine A was proposed. Mahimbrine A showed no antimicrobial activity at the concentration of 1 mg/mL.


Asunto(s)
Alcaloides/química , Biflavonoides/química , Catequina/análogos & derivados , Isoquinolinas/química , Mahonia/química , Alcaloides/síntesis química , Alcaloides/farmacología , Antiinfecciosos/farmacología , Espectroscopía de Resonancia Magnética con Carbono-13 , Catequina/química , Isoquinolinas/síntesis química , Isoquinolinas/farmacología , Pruebas de Sensibilidad Microbiana , Espectroscopía de Protones por Resonancia Magnética
13.
J Asian Nat Prod Res ; 18(8): 719-23, 2016 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-26949983

RESUMEN

Three novel oxazoline alkaloids, 1-oxa-3-azaspiro [4.5] dec-2-ene-8-one (1), 1-oxa-3-azaspiro [4.5] dec-2, 6-diene-8-one (2), and 1-oxa-3-azaspiro [4.5] dec-10-methoxy-2, 6-diene-8-one (3) were isolated from the methanol extract of the whole plant of Gymnotheca chinensis. The chemical structures were established by means of spectroscopic analysis including one- and two-dimensional NMR spectroscopy.


Asunto(s)
Alcaloides/aislamiento & purificación , Oxazoles/aislamiento & purificación , Saururaceae/química , Compuestos de Espiro/aislamiento & purificación , Alcaloides/química , Espectroscopía de Resonancia Magnética , Estructura Molecular , Oxazoles/química , Compuestos de Espiro/química , Estereoisomerismo
14.
Planta Med ; 82(8): 723-8, 2016 May.
Artículo en Inglés | MEDLINE | ID: mdl-26872322

RESUMEN

Four rare polycyclic spiro lignans (1-4) and four new biphenyl tetrahydrofuranone lignans (5-8) were isolated from the whole plant of Gymnotheca involucrata. The structures of the new compounds were elucidated on the basis of detailed spectroscopic analysis and the absolute configuration of 1 was confirmed by single crystal X-ray diffraction. Bioassay results showed that compounds 2 and 6 exhibited weak antifungal activity against Uromyces viciae-fabae at 100 ppm in leaf-disc assays, while compound 3 demonstrated moderate insecticidal activity against Diabrotica balteata at 500 ppm in an artificial diet assay.


Asunto(s)
Antifúngicos/aislamiento & purificación , Lignanos/aislamiento & purificación , Saururaceae/química , Animales , Antifúngicos/química , Antifúngicos/farmacología , Escarabajos/efectos de los fármacos , Cristalografía por Rayos X , Furanos/química , Furanos/aislamiento & purificación , Furanos/farmacología , Insecticidas/química , Insecticidas/aislamiento & purificación , Lignanos/química , Lignanos/farmacología , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Hojas de la Planta/química , Compuestos Policíclicos/química , Compuestos Policíclicos/aislamiento & purificación , Compuestos Policíclicos/farmacología
15.
Yao Xue Xue Bao ; 51(7): 1117-20, 2016 07.
Artículo en Chino | MEDLINE | ID: mdl-29897210

RESUMEN

In this study, seven bibenzyl compounds were isolated from the stem of Dendrobium nobile by silica gel, MCI column chromatographic and preparative HPLC technology. By using spectroscopic techniques including NMR and MS, these compounds were identified as 4,α-dihydroxy-3,5,3'-trimethoxybibenzyl (1), 4,5-dihydroxy-3,3',α-trimethoxybibenzyl (2), 4,4'-dihydroxy-3,5,3'-trimethoxybibenzyl (3), 4,5-dihydroxy-3,3'-dimethoxybibenzyl(4), 4,3'-dihydroxy-3,5-dimethoxybibenzyl (5), 5,4'-dihydroxy-3,3'-dimethoxybibenzyl (6) and 5,3'-dihydroxy-3-methoxybibenzyl (7). Compound 1 is a new compound and compound 4 was isolated from this plant for the first time.


Asunto(s)
Bibencilos/química , Dendrobium/química , Tallos de la Planta/química , Bibencilos/aislamiento & purificación , Cromatografía Líquida de Alta Presión , Espectroscopía de Resonancia Magnética
16.
Mol Clin Oncol ; 3(4): 880-888, 2015 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-26171200

RESUMEN

Numerous studies have investigated the prognostic role of brain and acute leukemia, cytoplasmic (BAALC) gene expression in adult patients with acute myeloid leukemia (AML); however, the results are inconclusive. A meta-analysis was conducted to provide a comprehensive evaluation of the prognostic role of BAALC gene expression in AML. Eligible studies were searched through PubMed, Embase, the Cochrane Library, the China National Knowledge Infrastructure and the China Biology Medicine Disc. Correlations between the BAALC gene expression and clinicopathological features and prognosis were analyzed. A total of 15 studies were examined. The pooled results suggest that high BAALC expression had an unfavorable outcome in AML. The combined hazard ratio (HR) for overall survival (OS) was 1.53 and the summary HR for the disease-free survival rate was 1.64. In addition, subgroup analyses considering cytogenetic and survival analysis were also conducted. High BAALC gene expression appeared to be an adverse prognostic indicator in patients with cytogenetically normal AML (HR for OS, 1.43) and in subgroups of survival analysis with multivariate analysis (HR for OS, 2.35). These results indicate that high BAALC gene expression served as an independent poor prognostic indicator in adult patients with AML.

17.
Chin J Nat Med ; 13(1): 65-8, 2015 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-25660290

RESUMEN

A new ursane-type triterpenoid saponin, 2α,3α,24-trihydroxyurs-12,20(30)-dien-28-oic acid ß-D-glucopyranosyl ester (1), together with six known triterpenoid saponins, was isolated and characterized from the aerial parts of Clematoclethra scandens subsp. actinidioides.


Asunto(s)
Actinidiaceae/química , Componentes Aéreos de las Plantas/química , Extractos Vegetales/química , Plantas Medicinales/química , Saponinas/aislamiento & purificación , Triterpenos/aislamiento & purificación , Estructura Molecular
18.
Nat Prod Commun ; 10(12): 2135-6, 2015 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-26882683

RESUMEN

Two new resorcylic acid lactones, 13-hydroxyhidroresorcylide (1) and 12-hydroxyhidroresorcylide (2), along with four known congeners (3-6) were isolated from Saccharicola bicolor, an endophytic fungus from Bergenia purpurascens. Their structures were elucidated by interpretation of the spectroscopic evidence.


Asunto(s)
Endófitos/química , Hongos/química , Lactonas/química , Resorcinoles/química , Saxifragaceae/química , Estructura Molecular
19.
Nat Prod Commun ; 10(12): 2151-3, 2015 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-26882688

RESUMEN

Seven cyclic lipopeptide biosurfactants (1-7) were isolated for the first time from the fermentation broth of endophytic Bacillus clausii DTM1 and were identified as anteisoC13[Val7] surfactin-(L-Glu)-O-methyl-ester (1), anteisoC12[Val7] surfactin (2), anteisoC15[Val7] surfactin (3), isoC14[Leu7] surfactin (4), anteisoC12[Leu7] surfactin (5), nC13[Leu7] surfactin (6), and anteisoC14[Leu7] surfactin-(L-Glu)-O-methyl-ester (7); 1 has not been isolated before as a natural product from any source. Plate-based herbicide and insecticide bioassays showed that all compounds exhibited interesting insecticidal and herbicidal activities.


Asunto(s)
Bacillus/metabolismo , Herbicidas/farmacología , Lipopéptidos/farmacología , Péptidos Cíclicos/farmacología , Animales , Áfidos/efectos de los fármacos , Arabidopsis/efectos de los fármacos , Bacillus/química , Herbicidas/química , Herbicidas/metabolismo , Insecticidas/química , Insecticidas/metabolismo , Insecticidas/farmacología , Lipopéptidos/química , Lipopéptidos/metabolismo , Datos de Secuencia Molecular , Péptidos Cíclicos/química , Péptidos Cíclicos/metabolismo
20.
Zhongguo Zhong Yao Za Zhi ; 38(3): 358-61, 2013 Feb.
Artículo en Chino | MEDLINE | ID: mdl-23668009

RESUMEN

To study the chemical constituents of Clematoclethra scandens subsp. actinidioides, chromatographic methods such as silica gel and MCI column chromatographic technology, and preparative HPLC were used and sixteen compounds were isolated from the aerial parts of this plant. By using spectroscopic techniques including 1H, 13C-NMR, HMBC and ESI-MS, these compounds were identified as betulinic acid (1), ursolic acid (2), oleanic acid (3), corosolic acid (4), 3beta-(trans-p-coumaroyloxy)-2alpha, 23-dihydroxyurs-12-en-28-oic acid (5), 3beta-(trans-p-coumaroyloxy)-2alpha, 23-dihydroxyurs-12, 20 (30)-dien-28-oic acid (6), 2alpha, 3alpha, 23-trihydroxyurs-12, 20 (30)-dien-28-oic acid (7), 2alpha, 3alpha, 23-trihydroxyurs-12-en-28-oic acid (8), asiatic acid (9), 2alpha, 3alpha, 24-tri-hydroxyurs-12-en-28-oic acid (10), 2alpha, 3beta, 23-trihydroxyurs-12, 20 (30)-dien-28-oic acid (11), 2alpha, 3beta, 19alpha, 24-tetrahydroxyurs-12-en-28-oic acid (12), 2alpha, 3alpha, 19alpha, 24-tetrahydroxyurs-12-en-28-oic acid (13), 2alpha, 3beta, 23, 24-tetrahydroxyurs-12-en-28-oic acid (14), 2alpha, 3alpha, 19alpha, 23, 24-pentahydroxyurs-12-en-28-oic acid (15) and daucosterol (16). Among them, compounds 3-6, 11-12, 14 and 15 were isolated from this endemic plant for the first time.


Asunto(s)
Actinidiaceae/química , Componentes Aéreos de las Plantas/química , Extractos Vegetales/química , Plantas Medicinales/química , Triterpenos/química , Cromatografía en Gel , Cromatografía Líquida de Alta Presión , Espectroscopía de Resonancia Magnética , Triterpenos/aislamiento & purificación
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