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1.
Phytochemistry ; 225: 114192, 2024 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-38901624

RESUMEN

Meliasanines A-L, twelve previously unreported tirucallane-type triterpenoids, together with fifteen known ones, have been isolated from the stem bark of Melia toosendan. Their structures and absolute configurations were determined based on HRESIMS, and NMR, combined with calculated ECD and single-crystal X-ray diffraction analyses. Subsequently, all compounds except 10 were evaluated for their inhibitory effect on the production of nitric oxide induced by lipopolysaccharide in RAW264.7 macrophage cells. The results indicated that seven compounds (1, 13, 14, 16, 20, 22, and 23) exhibited significant NO inhibitory effects, with IC50 values ranging from 1.35 to 5.93 µM, which were more effective than the positive control indomethacin (IC50 = 13.18 µM). Moreover, the corresponding results of Western blot analysis revealed that meliasanine A (1) can significantly suppress the protein expression of inducible nitric oxide synthase and cyclooxygenase 2 in a concentration-dependent manner. The mechanism study suggested that meliasanine A exerts an anti-inflammatory effect via the nuclear factor-κB signaling pathway by suppressing phosphorylation of P65 and IκBα.


Asunto(s)
Antiinflamatorios , Lipopolisacáridos , Melia , FN-kappa B , Óxido Nítrico , Transducción de Señal , Triterpenos , Ratones , Animales , Triterpenos/farmacología , Triterpenos/química , Triterpenos/aislamiento & purificación , FN-kappa B/metabolismo , FN-kappa B/antagonistas & inhibidores , Células RAW 264.7 , Transducción de Señal/efectos de los fármacos , Antiinflamatorios/farmacología , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Óxido Nítrico/biosíntesis , Óxido Nítrico/antagonistas & inhibidores , Óxido Nítrico/metabolismo , Estructura Molecular , Lipopolisacáridos/farmacología , Lipopolisacáridos/antagonistas & inhibidores , Melia/química , Óxido Nítrico Sintasa de Tipo II/metabolismo , Óxido Nítrico Sintasa de Tipo II/antagonistas & inhibidores , Corteza de la Planta/química , Ciclooxigenasa 2/metabolismo , Relación Dosis-Respuesta a Droga , Relación Estructura-Actividad
2.
Chem Biodivers ; 21(5): e202400030, 2024 May.
Artículo en Inglés | MEDLINE | ID: mdl-38511964

RESUMEN

A traditional Chinese medicine ingredient, dendrobine, has been demonstrated to have anti-inflammatory properties. However, due to its poor anti-inflammatory properties, its clinical use is limited. Consequently, we have designed and synthesized 32 new amide/sulfonamide dendrobine derivatives and screened their anti-inflammatory activities in vitro. Experiments showed that nitric oxide (NO) generation in lipopolysaccharide (LPS)-induced RAW264.7 cells was strongly reduced by derivative 14, with an IC50 of 2.96 µM. Western blot research revealed that 14 decreased the concentration-dependent expression of cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (INOS). Molecular docking was used to predict the binding of the inflammation-associated proteins COX-2 and INOS to compound 14.


Asunto(s)
Amidas , Ciclooxigenasa 2 , Lipopolisacáridos , Simulación del Acoplamiento Molecular , Óxido Nítrico Sintasa de Tipo II , Óxido Nítrico , Sulfonamidas , Animales , Ratones , Células RAW 264.7 , Sulfonamidas/química , Sulfonamidas/farmacología , Sulfonamidas/síntesis química , Lipopolisacáridos/antagonistas & inhibidores , Lipopolisacáridos/farmacología , Óxido Nítrico Sintasa de Tipo II/metabolismo , Óxido Nítrico Sintasa de Tipo II/antagonistas & inhibidores , Óxido Nítrico/antagonistas & inhibidores , Óxido Nítrico/biosíntesis , Óxido Nítrico/metabolismo , Ciclooxigenasa 2/metabolismo , Amidas/química , Amidas/farmacología , Amidas/síntesis química , Relación Estructura-Actividad , Antiinflamatorios/farmacología , Antiinflamatorios/química , Antiinflamatorios/síntesis química , Estructura Molecular , Relación Dosis-Respuesta a Droga , Antiinflamatorios no Esteroideos/farmacología , Antiinflamatorios no Esteroideos/síntesis química , Antiinflamatorios no Esteroideos/química
3.
Chem Biodivers ; 21(3): e202400184, 2024 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-38372676

RESUMEN

The phytochemical study of Peucedanum praeruptorum led to the isolation of twenty-five coumarins (1-25). Of which, (±) praeruptol A (±1), one pair of previous undescribed seco-coumarin enantiomers were obtained. Their structures were established according to HR-ESI-MS, NMR, X-ray single crystal diffraction analysis, as well as ECD calculation. All compounds were tested for anti-inflammatory activity in the RAW264.7 macrophage model, and eight compounds (7-10, and 13-16) exhibited significant inhibitory effects with IC50 values ranging from 9.48 to 34.66 µM. Among them, compound 7 showed the strongest inhibitory effect, which significantly suppressed the production of IL-6, IL-1ß, and TNF-α, as well as iNOS and COX-2 in a concentration-dependent manner. Further investigated results showed that compound 7 exerted an anti-inflammatory effect via the NF-κB signaling pathway.


Asunto(s)
Cumarinas , FN-kappa B , FN-kappa B/metabolismo , Cumarinas/farmacología , Cumarinas/metabolismo , Antiinflamatorios/farmacología , Extractos Vegetales/química , Transducción de Señal , Lipopolisacáridos/farmacología
4.
Chem Biodivers ; 21(2): e202301703, 2024 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-38055204

RESUMEN

Three undescribed limonoids (1-3), named aglaians G-I, and one new natural product azedaralide (4), together with nine known analogues (5-13) were isolated from the branches and leaves of Aglaia lawii by RP C18 column, silica gel column, Sephadex LH-20 column chromatography and preparative HPLC. The structures of the new compounds were elucidated by IR, HRESIMS, 1D, 2D NMR, electronic circular dichroism (ECD) calculations and X-ray crystallography diffraction analysis. The results of bioassay showed that the compound 12 exhibited potential inhibitory activity against six human tumor cell lines (MDA-MB-231, MCF-7, Ln-cap, A549, HeLa and HepG-2) with IC50 values as 8.0-18.6 µM.


Asunto(s)
Aglaia , Antineoplásicos , Limoninas , Humanos , Aglaia/química , Limoninas/farmacología , Limoninas/química , Estructura Molecular , Línea Celular Tumoral
5.
Fitoterapia ; 171: 105708, 2023 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-37866424

RESUMEN

Five undescribed triterpenoids and steroids (1-5), as well as ten known compounds, were purified from the branches and leaves of Cipadessa baccifera. Notably, 1 and 2 are rare cipadesin-type limonoids with an unusual 8,30-epoxide ring and 1,8-ether linkage, respectively. Compound 5 possessed pregnane steroid skeleton with an uncommon 5/6/6/6/5-fused ring system. Their structures were constructed by extensive spectroscopic analysis (NMR, IR, UV, and HRESIMS), and their absolute configurations were confirmed by ECD calculations and quantum chemical calculations. All the isolates were in vitro assayed for their antimicrobial potentials against 6 pathogenic microorganisms and antiproliferation activities against five human cancer cell lines. As a result, compounds 5, 12, 13, and 14 exhibited moderate antibacterial activities (MIC: 25-50 µg/mL). Moreover, 5 showed cytotoxicity against five cancer cell lines with IC50 values ranging from 8.0 to 19.9 µM.


Asunto(s)
Limoninas , Meliaceae , Triterpenos , Humanos , Estructura Molecular , Esteroides , Línea Celular Tumoral , Meliaceae/química
6.
Fitoterapia ; 160: 105217, 2022 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-35561838

RESUMEN

Two pairs of new enantiomeric flavonolignans, ±stachyols A and B (±1 and ± 2), along with two novel isoflavanelignans, stachyols C and D (3 and 4) were isolated from the roots of Indigofera stachyodes. Their chemical structures and absolute configurations were determined using nuclear magnetic resonance and comparison of experimental and theoretical electronic circular dichroism (ECD) spectra, as well as quantum chemical calculations. Of those compounds, 1 and 2 represented the first examples of flavonolignans with 5-deoxyflavonoids adduct phenylpropanoids. Moreover, 3 and 4 possess an unprecedented skeleton with isoflavanes adduct phenylpropanoids. The antioxidant activity was evaluated for all compounds in terms of ABTS+ and DPPH bioassays. Compounds 3 and 4 exhibited significant radical-scavenging activity in the ABTS+ assay, with IC50 values of 15.15 and 5.83 µM, respectively.


Asunto(s)
Flavonolignanos , Indigofera , Antioxidantes/química , Antioxidantes/farmacología , Dicroismo Circular , Estructura Molecular , Raíces de Plantas
7.
Phytochemistry ; 200: 113186, 2022 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-35500784

RESUMEN

Eleven undescribed limonoids, cipacinerasins A-K, involving of four diverse carbon skeletal types, along with fifteen known analogues, were isolated from the branches and leaves of Cipadessa baccifera. Within them, cipacinerasins A and B feature a rearranged tetrahydropyranyl ring B formed between C-8 and C-30, are unusual miscellaneous-type limonoids. Cipacinerasins E and F are rare trijugin-type limonoids, of which the D-ring δ-lactone is cleaved. Their structures were elucidated on the basis of extensive spectroscopic data (HRESIMS, NMR, UV and IR), electronic circular dichroism (ECD) calculations, and single-crystal X-ray diffraction analysis. All compounds were evaluated in vitro cytotoxicity against five human tumor cell lines (K562, HeLa, PC3, LN-Cap and Hell), and cipacinerasin E showed moderate antitumor activity with IC50 values ranging from 8.0 to 24.8 µM.


Asunto(s)
Limoninas , Meliaceae , Línea Celular Tumoral , Limoninas/química , Limoninas/farmacología , Meliaceae/química , Estructura Molecular , Hojas de la Planta/química
8.
Phytochemistry ; 195: 113047, 2022 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-34896812

RESUMEN

Aconitum pendulum N. Busch (Ranunculaceae) is rich in alkaloids with anti-inflammatory and analgesic activities. Many studies have focused on the identification or quantification of alkaloid components using low-throughput tests. However, the metabolic differences of plants from environmentally distinct regions remain unclear. The present study profiled alkaloid chemical compounds in the rhizomes of A. pendulum from different regions. A total of 80 chemical compounds were identified using a widely targeted ultra-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) approach. Principal component, hierarchical clustering, and orthogonal partial least squares-discriminant analyses of the chemical compounds indicated that the plants from 6 regions clearly separated into distinct groups. A total of 19 compounds contributed the most to the metabolite differences between collection areas and were identified as potential metabolic markers. The anti-inflammatory activities of the A. pendulum extracts were also evaluated and the potential environmental effects on the regulation of metabolite composition and bioactivity were explored. These results improve our understanding of the variation in chemical composition of plants from different regions and will serve as a reference for evaluating the medicinal value of A. pendulum in different environments.


Asunto(s)
Aconitum , Alcaloides , Cromatografía Líquida de Alta Presión , Cromatografía Liquida , Metabolómica , Espectrometría de Masas en Tándem
9.
J Asian Nat Prod Res ; 23(7): 644-651, 2021 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-33583289

RESUMEN

Two new compounds, including one new arylbenzofuran (1) and one new pterocarpanoid (2), along with nine known ones, were isolated from the seeds of Sophora tonkinensis. The structures of the new compounds were elucidated based on a comprehensive spectroscopic data analysis. Compounds 2 and 3 exhibited good anti-tobacco mosaic virus (TMV) activities with the protective inhibition rate of 69.62% and 68.72% respectively, at concentration of 100 µg/ml.


Asunto(s)
Sophora , Virus del Mosaico del Tabaco , Antivirales/farmacología , Estructura Molecular , Semillas
10.
J Asian Nat Prod Res ; 23(1): 73-81, 2021 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-31838892

RESUMEN

A new polycyclic polyprenylated acylphloroglucinol (PPAP), hypermonin C (1), along with nine known PPAPs (2-10) were obtained from the leaves and twigs of Hypericum monogynum. The structures of the isolates were determined on the basis of extensive spectroscopic analysis. The neuroprotective effects of the isolates against several chemical-induced injuries in SH-SY5Y and PC12 cells were assessed, and most of the compounds exhibited significant protective effects at 10 µg/ml. Especially, three compounds (1, 3, and 7) showed excellent neuroprotective activity with a cell viability of 92.4% ∼ 95.8% in KCl-induced SH-SY5Y cell injury. Their preliminary structure-activity relationship was also discussed and the configuration of substituent in furohyperforin may be critical for the neuroprotective activity of PPAP derivatives.


Asunto(s)
Hypericum , Fármacos Neuroprotectores , Animales , Estructura Molecular , Fármacos Neuroprotectores/farmacología , Células PC12 , Floroglucinol/farmacología , Hojas de la Planta , Ratas
11.
Org Lett ; 22(17): 6903-6906, 2020 09 04.
Artículo en Inglés | MEDLINE | ID: mdl-32822200

RESUMEN

Two novel polycyclic polyprenylated acylphloroglucinols (PPAPs), hyperfols A (1) and B (2), and two known biosynthetically related precursors (3 and 4) were isolated from Hypericum perforatum. Compound 1 possesses an unprecedented 2,3-seco-PPAP with a fused 5/5/9/5 tetracyclic skeleton, and 2 features a 30-norPPAP. Their structures were established by spectroscopic analysis, computer-assisted structure elucidation software, and electronic circular dichroism calculations. Moreover, compounds 1 and 4 exhibit significant cytotoxicity against human erythroleukemia cells by inducing cell apoptosis.


Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Hypericum/química , Floroglucinol/química , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Apoptosis/efectos de los fármacos , Dicroismo Circular , Humanos , Espectroscopía de Resonancia Magnética , Estructura Molecular
12.
Phytochemistry ; 164: 33-40, 2019 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-31071600

RESUMEN

Nine undescribed compounds, including five xanthone derivatives, two flavonoids, one 2-pyrone derivative, and one undescribed naturally occurring compound, along with 30 known phenolic compounds, were isolated from Hypericum japonicum. In addition, hyperjaponols A and B were identified as racemates. The structures and absolute configurations of the undescribed compounds were determined by comprehensive MS, NMR spectroscopy, and electronic circular dichroism (ECD) calculations. The cytotoxic effects of the isolated compounds on two human tumour cell lines (HEL and MDA-MB-231) were evaluated by the MTT assay. Eighteen compounds showed good inhibitory activities against the HEL cell line, with IC50 values of 3.53-18.7 µM, while nine compounds exhibited moderate cytotoxicity against the MDA-MB-231 cancer cell line, with IC50 values ranging from 4.92 to 10.75 µM. Their preliminary structure-activity relationship of the isolated compounds was also discussed.


Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Hypericum/química , Fenoles/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Estructura Molecular , Fenoles/química , Fenoles/aislamiento & purificación , Relación Estructura-Actividad
13.
Phytochemistry ; 162: 216-223, 2019 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-30953908

RESUMEN

Ten previously undescribed bibenzyl derivatives (bletistrins A-J), including 5 that have hydroxyl-substituted chiral centres on the aliphatic bibenzyl bridge, along with twelve known bibenzyl derivatives, were isolated from the rhizomes of Bletilla striata. The structures of bletistrins A-J were primarily elucidated on the basis of their 1D and 2D NMR spectroscopic data. The absolute configurations of bletistrins A, D, F, H and I were determined by electronic circular dichroism (ECD) spectroscopic analysis and optical rotation value. Most of the isolated compounds were evaluated for their antibacterial activities against 3 g-positive bacterial strains and 1 g-negative bacterial strain. Bletistrins F, G, and J, bulbocol, shanciguol and shancigusin B showed inhibitory activities, with MICs of (3-28 µg/mL) against S. aureus ATCC 6538.


Asunto(s)
Antibacterianos/química , Antibacterianos/farmacología , Bibencilos/química , Bibencilos/farmacología , Orchidaceae/química , Tubérculos de la Planta/química , Pruebas de Sensibilidad Microbiana , Modelos Moleculares , Conformación Molecular , Staphylococcus aureus/efectos de los fármacos
14.
Chin J Nat Med ; 16(8): 621-627, 2018 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-30197128

RESUMEN

In the present study, four new sesquiterpenoids, chimonols A-D (compounds 1-4), together with four known compounds (5-8) were isolated from the EtOAc extract of Chimonanthus praecox Link. The structures of these new compounds were elucidated on the basis of spectroscopic techniques (UV, IR, MS, and 1D and 2D NMR), and their absolute configurations were established by comparing experimental and calculated electronic circular dichroism (ECD) spectra. Compounds 1-8 were evaluated for antimicrobial activities and the minimum inhibitory concentrations (MICs) were determined by the broth microdilution method in 96-well culture plates. Compounds 1, 2, and 7 exhibited weak antibacterial effects for S. aureus (ATCC 6538), E. coli (ATCC 11775), and P. aeruginosa (ATCC 10145) with MIC values being 158-249 µg·mL-1. Compounds 3-7 showed activities against C. glabrata (ATCC 2001) and S. aureus (ATCC 43300) with MIC values being 128-197 µg·mL-1. Compounds 1-4 showed activity against S. aureus (ATCC 25923) with MIC values being 162-254 µg·mL-1. The present study provided a basis for future evaluation of these compounds as antibacterial agents.


Asunto(s)
Antibacterianos/farmacología , Calycanthaceae/química , Extractos Vegetales/farmacología , Sesquiterpenos/farmacología , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Escherichia coli/efectos de los fármacos , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Sesquiterpenos/química , Sesquiterpenos/aislamiento & purificación , Staphylococcus aureus/efectos de los fármacos
15.
Chem Biodivers ; 14(12)2017 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-28963759

RESUMEN

Two new flavones, 6,7-methylenedioxy-4-hydroxypeltogynan-7'-one (1), cochliophilin B (2), as well as two known ones, cochliophilin A (3) and 6-methoxy-7-hydroxy flavone (4), were isolated from the ethanol extract of the root of Phytolacca acinosa Roxb. Compound 1 is a flavanol framework with one δ-lactone unit, which is rather rare in nature. The structures of the new compounds were determined on the basis of extensive spectroscopic (IR, MS, 1D- and 2D-NMR) analyses, the absolute configuration of 1 was established by comparing experimental and calculated electronic circular dichroism spectra. The structures of known compounds were fixed by comparison with literatures data. Compounds 2 and 4 showed modest inhibitory activities against BEL-7402 cell line, with IC50 values of 28.22 and 39.16 µmol/L, respectively.


Asunto(s)
Flavonas/química , Phytolacca/química , Células A549 , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Flavonas/aislamiento & purificación , Flavonas/toxicidad , Humanos , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Conformación Molecular , Mycobacterium tuberculosis/efectos de los fármacos , Phytolacca/metabolismo , Raíces de Plantas/química , Raíces de Plantas/metabolismo , Espectrofotometría Infrarroja
16.
Biochem Res Int ; 2017: 6257240, 2017.
Artículo en Inglés | MEDLINE | ID: mdl-28713593

RESUMEN

To get inside the properties of N,N-disubstituted Schiff bases, we synthesized three high-yielding benzaldehyde Schiff bases. We used the reaction between salicylaldehyde and different diamine compounds, including diamine, ethanediamine, and o-phenylenediamine, determining the structure of obtained molecules by nuclear magnetic resonance spectroscopy and electrospray ionization mass spectroscopy. We thus evaluated the microbicidal and antitumor activity of these compounds, showing that salicylaldehyde-hydrazine hydrate Schiff base (compound 1a) significantly inhibited the growth of S. aureus; salicylaldehyde-o-phenylenediamine Schiff base (compound 1c) displayed a strong capability to inhibit the proliferation of leukemia cell lines K562 and HEL. Moreover, we observed that the antibacterial action of 1a might be associated with the regulation of the expression of key virulence genes in S. aureus. Compound 1c resulted in a strong apoptotic activity against leukemia cells, also affecting the cell cycle distribution. Overall, our novel N,N-disubstituted Schiff bases possess unique antibacterial or antitumor activities that exhibit the potent application prospect in prophylactic or therapeutic interventions, providing new insights for developing new antibacterial and anticancer chemical agents.

17.
Zhongguo Zhong Yao Za Zhi ; 40(15): 3009-12, 2015 Aug.
Artículo en Chino | MEDLINE | ID: mdl-26677702

RESUMEN

Derris eriocarpa, a traditional Chinese medicine belonging to the family of Leguminosae, is widely distributed mainly over Yunnan, Guangxi and Guizhou of China. Modern pharmacological researches on this herb showed that it had extensive bioactivities, such as promoting urination, removing dampness and cough and reducing inspissated mucus and other biological activities. The extensive studies on the chemical constituents of this plant have resulted in the isolation of triterpenoids, steroids, fatty acid and others, but the flavone compounds haven't reported before. In our further research on the ethyl acetate of this plant, nine flavone compounds were obtained by column chromatography on silica gel, Sephadex LH-20, semi-prep HPLC, polyamide column chromatography and recrystallization for separation and purification. The structures were determined on the basis of extensive spectroscopic analysis, including MS, NMR experiments and comparison with spectroscopic data in the literature, respectively, as diosmetin (1), 3, 3'-di-O-methylquercetin (2), afromosin (3), 6, 3'-dihydroxy-7, 4'-dimethoxyisoflavone (4), odoratin (5), 7, 3'-dihydroxy-8, 4'-dimethoxyisoflavone (6), 6, 4'-dihydroxy-7, 3'-dimethoxyisoflavone (7), 5, 7, 4'-trihydroxy-3, 3', 5'-trimethoxyflavone (8), and alpinumisoflavone (9). All these compounds were isolated from Derris eriocarpa How for the first time. And the in vitro assays showed that compound 2 possessed moderate inhibitory activity against human cancer cells K562 and HEL.


Asunto(s)
Derris/química , Flavonoides/aislamiento & purificación , Flavonoides/química , Flavonoides/farmacología , Humanos , Células K562
18.
Eur J Med Chem ; 97: 83-93, 2015 Jun 05.
Artículo en Inglés | MEDLINE | ID: mdl-25982329

RESUMEN

There is an urgent need to develop new antibacterial agents because of multidrug resistance by bacteria and fungi. Schiff bases (aldehyde or ketone-like compounds) exhibit intense antibacterial characteristics, and are therefore, promising candidates as antibacterial agents. To investigate the mechanism of action of newly designed benzaldehyde Schiff bases, a series of high-yielding benzaldehyde Schiff bases were synthesized, and their structures were determined by NMR and MS spectra data. The structure-microbicidal activity relationship of derivatives was investigated, and the antibacterial mechanisms were investigated by gene assays for the expression of functional genes in vitro using Escherichia coli, Staphylococcus aureus, and Bacillus subtilis. The active compounds were selective for certain active groups. The polar substitution of the R2 group of the amino acids in the Schiff bases, affected the antibacterial activity against E. coli and S. aureus; specific active group at the R3 or R4 groups of the acylhydrazone Schiff bases could improve their inhibitory activity against these three tested organisms. The antibacterial mechanism of the active benzaldehyde Schiff bases appeared to regulate the expression of metabolism-associated genes in E. coli, hemolysis-associated genes in B. subtilis, and key virulence genes in S. aureus. Some benzaldehyde Schiff bases were bactericidal to all the three strains and appeared to regulate gene expression associated with metabolism, hemolysis, and virulence, in vitro. The newly designed benzaldehyde Schiff bases possessed unique antibacterial activity and might be potentially useful for prophylactic or therapeutic intervention of bacterial infections.


Asunto(s)
Antiinfecciosos/síntesis química , Benzaldehídos/síntesis química , Bases de Schiff/síntesis química , Antiinfecciosos/química , Antiinfecciosos/farmacología , Bacillus subtilis/efectos de los fármacos , Bacillus subtilis/genética , Benzaldehídos/química , Benzaldehídos/farmacología , Escherichia coli/efectos de los fármacos , Escherichia coli/genética , Expresión Génica/efectos de los fármacos , Hemólisis/efectos de los fármacos , Estructura Molecular , Bases de Schiff/química , Bases de Schiff/farmacología , Staphylococcus aureus/efectos de los fármacos , Staphylococcus aureus/genética , Relación Estructura-Actividad , Virulencia/efectos de los fármacos
19.
Bioorg Med Chem Lett ; 25(9): 1823-6, 2015 May 01.
Artículo en Inglés | MEDLINE | ID: mdl-25863432

RESUMEN

Three new cytochalasins (1-3) together with two known cytochalasin analogues (4 and 5) were isolated from the chloroform fraction of ethanolic extract of a medicinal macrofungus Cordyceps taii. The structures of the new compounds were elucidated on the basis of spectroscopic analysis, including HRESIMS, 1D and 2D NMR experiments. The cytotoxicities of Compounds 1-5 were investigated by the sulforhodamine B (SRB) method in vitro against human highly metastatic lung cancer cell 95-D, human lung cancer cell line A-549 and normal hepatocyte HL-7702. The results revealed that Compounds 4 and 5 showed potent antitumor activities against human lung cancer cell 95-D with IC50 value of 3.67 and 4.04 µM, respectively. In comparison with cisplatin, the first-line chemotherapy drug, they had little or no cytotoxicity on normal cells, but showed stronger cytotoxic effects on cancer cells 95-D.


Asunto(s)
Antineoplásicos/farmacología , Cordyceps/química , Citocalasinas/farmacología , Antineoplásicos/química , Antineoplásicos/aislamiento & purificación , Línea Celular , Proliferación Celular/efectos de los fármacos , Citocalasinas/química , Citocalasinas/aislamiento & purificación , Relación Dosis-Respuesta a Droga , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Estructura Molecular , Relación Estructura-Actividad
20.
Bioorg Med Chem Lett ; 22(13): 4444-6, 2012 Jul 01.
Artículo en Inglés | MEDLINE | ID: mdl-22658863

RESUMEN

Further investigation on the phytochemistry of the plant Aconitum carmichaeli Debx. led to isolate a new franchetine type C(19)-diterpenoid alkaloid, guiwuline 1. Its structure was established on the basis of the spectroscopic data (1D and 2D NMR, HRESIMS, UV, IR). In mouse hot-plate test and acute toxicity assay, compound 1 exhibited potential analgesic activity (ED(50), 15 mg/kg) and showed little toxicity to mice (LD(50), 500 mg/kg). The results indicate that compound 1 may be used as a lead molecule to develop novel analgesic agents.


Asunto(s)
Aconitum/química , Alcaloides/química , Analgésicos/química , Diterpenos/química , Alcaloides/farmacología , Alcaloides/toxicidad , Analgésicos/farmacología , Analgésicos/toxicidad , Animales , Conducta Animal/efectos de los fármacos , Diterpenos/farmacología , Diterpenos/toxicidad , Espectroscopía de Resonancia Magnética , Ratones , Conformación Molecular , Raíces de Plantas/química , Espectrometría de Masa por Ionización de Electrospray , Espectrofotometría Infrarroja , Espectrofotometría Ultravioleta , Temperatura , Pruebas de Toxicidad
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