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1.
Orthop Surg ; 13(7): 1969-1978, 2021 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-34523808

RESUMO

OBJECTIVE: To evaluate the safety and stability of 3D-printed interbody fusion cages (3D-printed cages) in anterior cervical discectomy and fusion (ACDF) by investigating the mid- and long-term follow-up outcomes. METHODS: In this prospective study, the clinical data of 30 patients with CSM admitted to the Second Hospital of Shanxi Medical University from May 2012 to May 2014 were analyzed. The cohort comprised 18 males and 12 females with an average age of 60.22 ± 3.2 years. All patients were examined by X-ray, CT and MRI before the operation. A total of 30 cases of CSM were treated by ACDF with 3D printed cage implantation. Mid- and long-term follow-ups were performed after the surgery. Clinical efficacy was evaluated by comparing the JOA score, SF-36 score, change in neurological function, cervical curvature index (CCI), vertebral intervertebral height (VIH) and fusion rate before the operation, 6 months after the operation, and at the last follow-up. RESULTS: Two of the 30 patients were lost to follow-up. The remaining patients were followed up for 48-76 (65.23 ± 3.54) months. The patients recovered satisfactorily with a significant clinical effect. The JOA score increased meanfully and the improvement rate was 89.4% at the final follow-up. The SF-36 score increased significantly from pre- to postoperatively. The height of the intervertebral space at the last follow-up was not statistically significantly different from that at 6 months after surgery (P > 0.05), showing that the height of the intervertebral space did not change much and the severity of cage subsidence (CS) decreased. The CCI improved from pre- to postoperatively. The CCI did not change much from the 6-month follow-up to the last follow-up. and the cage rate (CR) was 100% at the 6-month and last follow-ups. No severe complications, such as spinal cord injury, esophageal fistula, cerebrospinal fluid leakage, cervical hematoma or wound infection, occurred in any of the patients. CONCLUSION: The clinical and radiological results show that the application of 3D-printed cages in ACDF can significantly relieve symptoms. Moreover, 3D-printed cages can restore the curvature of the cervical spine, effectively maintain the intervertebral height for a long time, and prevent complications related to postoperative subsidence.


Assuntos
Vértebras Cervicais/cirurgia , Discotomia/métodos , Impressão Tridimensional , Doenças da Medula Espinal/cirurgia , Fusão Vertebral/instrumentação , Feminino , Seguimentos , Humanos , Masculino , Pessoa de Meia-Idade , Estudos Prospectivos , Resultado do Tratamento
2.
Zhongguo Zhong Yao Za Zhi ; 46(16): 4131-4138, 2021 Aug.
Artigo em Chinês | MEDLINE | ID: mdl-34467724

RESUMO

Eleven condensed tannins were isolated from the roots of Indigofera stachyodes by various column chromatography techniques including silica gel, octadecyl silica(ODS), Sephadex LH-20, and semi-preparative high performance liquid chromatography(HPLC). These compounds were identified on the basis of physicochemical properties, nuclear magnetic resonance(NMR) and mass spectrometry(MS) data as stachyotannin A(1), epicatechin-(2ß→O→7,4ß→8)-epiafzelechin-(4ß→8)-catechin(2), cinnamtannin D1(3), cinnamtannin B1(4), epicatechin-(2ß→O→7,4ß→8)-epiafzelechin-(4α→8)-epicatechin(5), gambiriin C(6), proanthocyanidin A1(7), proanthocyanidin A2(8), aesculitannin B(9), proanthocyanidin A4(10), and procyanidin B5(11). Compound 1 is a new compound. Compounds 2-11 were isolated from Indigofera for the first time. Furthermore, compounds 1, 2, and 4-11 showed inhibitory effects on thrombin-induced ATP release in platelets.


Assuntos
Indigofera , Proantocianidinas , Cromatografia Líquida de Alta Pressão , Espectroscopia de Ressonância Magnética , Extratos Vegetais
3.
Phytochemistry ; 186: 112729, 2021 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-33721798

RESUMO

Five pairs of undescribed naphthalenone derivative enantiomers, xylarinaps A-E, including one pair of indole naphthalenones and four pairs of naphthalene-naphthalenone dimers, were isolated from the ethyl acetate extracts of the solid fermentation of Xylaria nigripes, which has been used as a traditional Chinese medicinal fungus for the treatment of insomnia, trauma, and depression. The structures of these enantiomers were elucidated based on comprehensive spectroscopic analysis, including NMR and HRESIMS. Their absolute configurations were assigned by the experimental and calculated ECD data. The neuroprotective effects of all the compounds against damage to PC12 cells by oxygen and glucose deprivation (OGD) were evaluated by an in vitro bioassay. The results revealed that xylarinaps A, B, D, and E significantly enhanced cell viability, decreased the levels of malondialdehyde (MDA), increased the levels of superoxide dismutase (SOD) and glutathione peroxidase (GSH-Px), as well as further markedly inhibiting apoptosis, which indicated that these results could be the mode of action of their neuroprotective effect.


Assuntos
Fármacos Neuroprotetores , Animais , Apoptose , Ascomicetos , Glutationa Peroxidase/metabolismo , Glutationa Peroxidase/farmacologia , Malondialdeído , Fármacos Neuroprotetores/farmacologia , Estresse Oxidativo , Células PC12 , Ratos , Superóxido Dismutase/metabolismo
4.
J Asian Nat Prod Res ; 23(8): 796-802, 2021 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-32608251

RESUMO

One new pentacyclic triterpenoid, urs-12,16-dien-3-one (1), together with twelve known pentacyclic triterpenoids (2‒13), were isolated from the twigs and leaves of Melaleuca linariifolia. Their structures were characterized by their 1D- and 2 D-NMR spectra analysis and mass spectra studies. Furthermore, all isolated compounds were tested the inhibitory effect on proliferation of six human cancer cell lines in vitro, including NCI-H441, NCI-H460, A549, SKOV3, hela, and caki-1 cells. Among them, compounds 3, 5, 7, 9, 12, and 13 exhibited moderate antiproliferative activities with IC50 values ranging from 3.85 to 33.31 µM.


Assuntos
Melaleuca , Triterpenos , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Folhas de Planta , Triterpenos/farmacologia
5.
J Org Chem ; 85(17): 11350-11358, 2020 09 04.
Artigo em Inglês | MEDLINE | ID: mdl-32786639

RESUMO

GIAO 13C NMR calculation plays important roles in structural assignment for small organic molecules. Especially, higher accuracy and confidence are required for the structural assignation of complex organic molecules. In this GIAO 13C NMR calculation strategy, carbons were sorted according to their type of hybridization, radii of solvation cavity, or solvent interactions. The calculated shielding tensors of carbons in each sorted training set were linear-regressed with experimental data separately, and the obtained linear parameters were used to convert calculated shielding tensors into calculated chemical shifts. This approach shows significantly improved accuracy, especially for sp2 carbons, compared to conventional GIAO 13C NMR calculation protocols. A statistic-based probability algorithm was proposed to quantify the reliability of structural assignation. With empirical linear parameters for three commonly used NMR solvents as well as an easy-to-use script and a spreadsheet, this 13C NMR calculation protocol provides a useful tool for structural validation or assignation of ambiguous organic structures.

6.
Nat Prod Res ; : 1-8, 2020 Aug 07.
Artigo em Inglês | MEDLINE | ID: mdl-32762444

RESUMO

Four new prenylflavonol glycosides (1-4) along with two known analogues (5-6) were isolated from the leaves of Cyclocarya paliurus for the first time. The structures of these compounds were characterized by comprehensive analysis of 1 D, 2 D NMR, HRESIMS, UV data and enzymatic hydrolysis. In bioassays, compounds 1-4 were evaluated for inhibitory effects on xanthine oxidase (XOD) and effects on the inhibition of nitric oxide (NO) production in lipopolysaccharide (LPS) induced RAW264.7 cells. Moreover, compounds 1 and 2 showed outstanding XOD inhibitions with IC50 values of 18.16 ± 3.91 and 37.65 ± 5.67 µM, and exhibited inhibitions against LPS-induced NO production with IC50 values of 80.50 ± 3.09 and 82.28 ± 2.87 µM.

7.
Bioorg Chem ; 101: 104018, 2020 08.
Artigo em Inglês | MEDLINE | ID: mdl-32629277

RESUMO

Eight new prenylflavonol glycosides (1-8), along with five known analogues (9-13) were isolated from the n-butanol extract of the dried leaves of Cyclocarya paliurus (family Juglandaceae) for the first time. The structures of these compounds were characterized by comprehensive analysis of 1D, 2D NMR, HRESIMS, UV data and acid hydrolysis. In bioassay, all these thirteen prenylflavonol glycosides exhibited inhibitory effects on xanthine oxidase (XOD) activity. Especially compounds 2 and 7, showed outstanding IC50 values of 31.81 ± 2.20 and 29.71 ± 3.69 µM, respectively.


Assuntos
Inibidores Enzimáticos/farmacologia , Flavonóis/farmacologia , Glicosídeos/farmacologia , Juglandaceae/química , Folhas de Planta/química , Xantina Oxidase/antagonistas & inibidores , Extratos Vegetais/química , Análise Espectral/métodos , Relação Estrutura-Atividade
8.
J Nat Prod ; 83(7): 2129-2144, 2020 07 24.
Artigo em Inglês | MEDLINE | ID: mdl-32633512

RESUMO

A phytochemical investigation of the MeOH extract of the leaves and twigs of Amentotaxus argotaenia, a relict vulnerable coniferous species endemic to China, led to the isolation and characterization of 35 diterpenoids/norditerpenoids. Twenty of these are new, including 11 ent-kaurane-type (amentotaxins C-M, 1-11, respectively), three icetexane-type [= 9(10→20)abeo-abietane-type (amentotaxins N-P, 12-14, respectively)], four ent-labdane-type (amentotaxins Q-T, 15-18, respectively), and two isopimarane-type [amentotaxins U (19) and V (20)] compounds. Their structures were elucidated on the basis of spectroscopic data, single-crystal X-ray diffraction, the modified Mosher's method, and electronic circular dichroism data analyses. Compounds 1-9 are rare 18-nor-ent-kaurane-type diterpenoids featuring a 4ß,19-epoxy ring. All the isolates were evaluated for their cytotoxic effects against a small panel of cultured human cancer cell lines (HeLa, A-549, MDA-MB-231, SKOV3, Huh-7, and HCT-116), and some of them exhibited cytotoxicities with IC50 values ranging from 1.5 to 10.0 µM.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Diterpenos/química , Diterpenos/farmacologia , Folhas de Planta/química , Taxaceae/química , Linhagem Celular Tumoral , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Estrutura Molecular , Análise Espectral/métodos
9.
Zhongguo Zhong Yao Za Zhi ; 45(10): 2411-2416, 2020 May.
Artigo em Chinês | MEDLINE | ID: mdl-32495600

RESUMO

Two new phenylpropanoid amide glycosides and ten analogues were isolated from the CH_2Cl_2 layer of 95% ethanol extract of the whole plants of Corydalis racemosa by using various chromatographic techniques, including silica gel, Sephadex LH-20, ODS column chromatographies, and semi-preparative HPLC. Their structures were identified on the basis of physicochemical properties, MS, NMR, and IR spectroscopic data as N-cis-sinapoyltyramine-4'-O-ß-glucoside(1), N-cis-sinapoyl-3-methoxytyramine-4'-O-ß-glucoside(2), N-cis-sinapoyltyramine(3), N-cis-feruloyltyramine(4), N-trans-cinnamoyltyramine(5), N-trans-feruloylphenethylamine(6), N-trans-p-methoxycinnamoyl-3-hydoxyoctopamine(7), N-cis-feruloyl-3-methoxytyramine(8), N-trans-feruloyltyramine(9), N-trans-feruloyl-3-methoxytyramine(10), N-trans-sinapoyltyramine(11), and N-trans-p-coumaroyltyramine(12). Compounds 1 and 2 are new compounds. Compounds 3-7 are obtained from the plants of Papaveraceae for the first time, and compounds 8-12 are firstly isolated from C. racemosa.


Assuntos
Corydalis , Amidas , Cromatografia Líquida de Alta Pressão , Glucosídeos , Glicosídeos
10.
J Nat Prod ; 83(5): 1725-1729, 2020 05 22.
Artigo em Inglês | MEDLINE | ID: mdl-32330030

RESUMO

Two skeletally novel tetracyclic diterpenoids, psathyrins A (1) and B (2), have been characterized from cultures of the basidiomycete Psathyrella candolleana. Their structures including absolute configurations were established by means of spectroscopic methods, as well as ECD calculations. They possess a novel 5/5/4/6-fuesd ring system, for which the biosynthetic pathway is proposed. Compounds 1 and 2 inhibited the growth of Staphylococcus aureus and Salmonella enterica.


Assuntos
Antibacterianos/farmacologia , Basidiomycota/química , Diterpenos/farmacologia , Staphylococcus aureus/efeitos dos fármacos , Agaricales , Antibacterianos/química , Antibacterianos/isolamento & purificação , Diterpenos/química , Diterpenos/isolamento & purificação , Estrutura Molecular
11.
Nat Prod Res ; : 1-7, 2020 Apr 21.
Artigo em Inglês | MEDLINE | ID: mdl-32316785

RESUMO

Three previously undescribed dammarane triterpenoid glycosides (1-3) along with five known analogues (4-8) were isolated from the leaves of Cyclocarya paliurus. Their structures and configurations were determined on the basis of comprehensive spectroscopic analyses, chemical hydrolysis and DFT GIAO 13C NMR calculation. All the isolates were evaluated cytotoxic activities against seven human cancer cell lines (MCF-7, PC-3, Du145, NCI-H1975, PC-9, SKVO3 and HepG2). Moreover, compound 4 showed a wide spectrum of cytotoxicity against human cancer cells with IC50 values ranging from 11.31 to 29.51 µM.

12.
BMC Musculoskelet Disord ; 21(1): 75, 2020 Feb 05.
Artigo em Inglês | MEDLINE | ID: mdl-32024507

RESUMO

BACKGROUND: For patients with spinal canal stenosis in the upper cervical spine who undergo C3-7 laminoplasty alone, it remains impossible to achieve full decompression due to its limited range. This study explores the extension of expansive open-door laminoplasty (EODL) to C1 and C2 for the treatment of cervical spinal stenosis of the upper cervical spine and its effects on cervical sagittal parameters. METHODS: A retrospective analysis of 33 patients presenting with symptoms of cervical spondylosis myelopathy (CSM) and ossification in the posterior longitudinal ligament (OPLL) of the upper cervical spine from February 2013 to December 2015 was performed. Furthermore, the changes in the C0-2 Cobb angle, C1-2 Cobb angle, C2-7 Cobb angle, C2-7 SVA, and T1-Slope in lateral X-rays of the cervical spine were measured before, immediately after, and 1 year after the operation. JOA and NDI scores were used to evaluate spinal cord function. RESULTS: The C0-2 and C1-2 Cobb angles did not significantly increase (P = 0.190 and P = 0.081), but the C2-7 Cobb angle (P = 0.001), C2-7 SVA (P < 0.001), and T1-Slope (P < 0.001) significantly increased from preoperative to 1 year postoperative. In addition, C2-7 SVA was significantly correlated with the T1-Slope (Pearson = 0.376, P < 0.001) and C0-2 Cobb angle (Pearson = 0.287, P = 0.004), and the C2-7 SVA was negatively correlated with the C2-7 Cobb angle (Pearson = - 0.295, P < 0.001). The average preoperative and postoperative JOA scores were 8.3 ± 1.6 and 14.6 ± 1.4 points, respectively, indicating in a postoperative neurological improvement rate of approximately 91.6%. The average preoperative and final follow-up NDI scores were 12.62 ± 2.34 and 7.61 ± 1.23. CONCLUSIONS: The sagittal parameters of patients who underwent EODL extended to C1 and C2 included loss of cervical curvature, increased cervical anteversion and compensatory posterior extension of the upper cervical spine to maintain visual balance in the field of vision. However, the changes in cervical spine parameters were far less substantial than the alarm thresholds reported in previous studies. We believe that EODL extended to C1 and C2 for the treatment of patients with spinal canal stenosis in the upper cervical spine is a feasible and safe procedure with excellent outcomes.


Assuntos
Vértebras Cervicais/diagnóstico por imagem , Descompressão Cirúrgica/métodos , Laminoplastia/métodos , Ossificação do Ligamento Longitudinal Posterior/cirurgia , Compressão da Medula Espinal/cirurgia , Espondilose/cirurgia , Idoso , Vértebras Cervicais/cirurgia , Descompressão Cirúrgica/efeitos adversos , Estudos de Viabilidade , Feminino , Seguimentos , Humanos , Laminoplastia/efeitos adversos , Masculino , Pessoa de Meia-Idade , Ossificação do Ligamento Longitudinal Posterior/complicações , Período Pós-Operatório , Radiografia , Estudos Retrospectivos , Compressão da Medula Espinal/etiologia , Espondilose/complicações , Resultado do Tratamento
13.
Orthop Surg ; 12(1): 248-253, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-32077255

RESUMO

OBJECTIVE: To observe and evaluate the clinical curative effect of a new type of open-powered cervical spine system developed for anterior cervical surgery. METHODS: A retrospective analysis was performed in our hospital in 2015-2017 of 329 orthopaedic patients treated with cervical anterior decompression, cage or titanium mesh graft fusion, new open-powered nail plate or traditional cervical anterior screw plate. A total of 154 (control group) and 175 (observation group) cases were fixed with conventional cervical- and new open-powered nail plates, respectively. Postoperative follow-up was performed. Cervical stability, internal fixation position, and bone graft fusion were evaluated by imaging. Operative time, intraoperative blood loss, cervical Cobb angle, pain visual analogue scale (VAS) score, and Japanese orthopaedic association (JOA) score were compared between the groups. JOA scoring (spinal cord function) and neurological function improvement rate (IR) were used to assess clinical efficacy. RESULTS: The patients were followed up for 8-36 months with an average of 19.48 months. There was no significant difference in the operation time and intraoperative blood loss between the two groups (P > 0.05). In the control group, the Cobb angles of the cervical spine were 5.13° ± 1.28°, 10.46° ± 1.07°, and 9.72° ± 1.43° before and after the operation. The observation group was followed by the Cobb angle of the cervical spine before and after the operation. They were 4.96° ± 1.39°, 11.67° ± 0.93°, and 11.13° ± 1.19°, respectively; the JOA scores before the operation, 1 week after the operation, and at the last follow-up were (8.07 ± 1.13) points and (13.57 ± 0.82) points, and (14.19 ± 0.96) points, respectively; the IR was 86.52% ± 9.33%. The preoperative, postoperative 1 week, and last follow-up JOA scores in the observation group were (8.37 ± 1.29) points, (14.11 ± 0.93) points, and (14.95 ± 0.78) points respectively. The IR was 88.74% ± 8.16% in the scores; the VAS scores were (5.54 ± 0.89) points, (1.73 ± 0.71) points, and (1.48 ± 0.52) points in the preoperative, postoperative 1 week, and last follow-up in the control group. The VAS scores were (5.81 ± 0.94) points, (1.82 ± 0.61) points, and (1.16 ± 0.49) points before, 1 week, and after the final follow-up. The JOA score and IR, VAS score and preoperative comparison between the two groups were statistically significant (P < 0.05), but there was no statistically significant difference between the two groups (P > 0.05). CONCLUSION: The new open-powered nail anterior cervical plate system can achieve the same clinical effect as the traditional anterior cervical plate fixation in anterior cervical surgery, but it can simplify the operation process, effectively make up for the shortcomings of the traditional anterior cervical plate operation, and obtain satisfactory clinical application effect, which is worthy of clinical promotion.


Assuntos
Placas Ósseas , Parafusos Ósseos , Vértebras Cervicais/cirurgia , Fixação Interna de Fraturas/instrumentação , Fusão Vertebral/instrumentação , Adulto , Idoso , Idoso de 80 Anos ou mais , Desenho de Equipamento , Feminino , Fixação Interna de Fraturas/métodos , Humanos , Masculino , Pessoa de Meia-Idade , Exame Neurológico , Medição da Dor , Estudos Retrospectivos , Fusão Vertebral/métodos
14.
Orthop Surg ; 12(1): 254-261, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-32077263

RESUMO

OBJECTIVE: To develop a new type of open dynamic cervical spine system and study its biomechanical properties. METHODS: Ten fresh goat spine specimens were used in this study. Using high precision digital display grating displacement sensor system, a new type of open dynamic nail plate fixation was compared with Atlantis nail plate fixation in terms of the stability of cervical vertebrae, pull-out strength, and fatigue strength. RESULTS: Biomechanical tests showed: (i) the new type of open dynamic cervical anterior nail plate system has similar three-dimensional stability as the Atlantis nail plate system, and can ensure the stability of anterior cervical fixation surgery; (ii) the fatigue life and fatigue strength of this new open dynamic anterior cervical nail plate and Atlantis nail plate are similar, and can adequately maintain the cervical stability after anterior bone graft fusion, to ensure long-term safety and efficacy of the nail plate system in the body; and (iii) the overall fixed performance of the new type of open dynamic cervical nail system is satisfactory. CONCLUSION: The new type of open dynamic anterior cervical nail plate system has satisfactory biomechanical characteristics and cervical spine stability effect.


Assuntos
Placas Ósseas , Parafusos Ósseos , Vértebras Cervicais/cirurgia , Teste de Materiais , Fusão Vertebral/instrumentação , Animais , Fenômenos Biomecânicos , Desenho de Equipamento , Cabras , Estresse Mecânico
15.
J Nat Prod ; 83(2): 216-222, 2020 02 28.
Artigo em Inglês | MEDLINE | ID: mdl-31994397

RESUMO

Palhinosides A-H (1-8), new flavone glucosidic truxinate esters, including ß-truxinate and µ-truxinate forms, were isolated from Palhinhaea cernua. Their structures were elucidated by extensive spectroscopic methods and chemical analyses. The flavone glucoside cyclodimers possess a unique cyclobutane ring in their carbon scaffolds. Compounds 2-7 represent three pairs of stereoisomers (2/3, 4/5, 6/7). The protective effects of 1-8 against the damage of HT-22 cells induced by l-glutamate were evaluated, and compounds 4 and 5 showed better neuroprotective effects than the positive control, Trolox.


Assuntos
Flavonas/isolamento & purificação , Lycopodiaceae/química , Triterpenos/isolamento & purificação , Ésteres , Flavonas/química , Glucosídeos , Estrutura Molecular , Fármacos Neuroprotetores , Triterpenos/química
16.
Phytochemistry ; 169: 112184, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31678787

RESUMO

An extensive phytochemical investigation on the chemical constituents from the needles and twigs of the vulnerable conifer Pseudotsuga sinensis yielded 19 diterpenoids and 21 sesquiterpenoids with various carbocyclic skeletons. Among them, 13 (named pseudosinins A-M, resp.) were undescribed compounds. Their structures with absolute configurations were characterized by a combination of spectroscopic methods, calculated and experimental electronic circular dichroism (ECD) data, quantum chemical calculations of the chemical shifts, and single crystal X-ray diffraction analyses. In particular, an array of labdane-derived norditerpenoids with C19-, C18-, and C16-skeletons, and related drimane-type sesquitepenoids with C15- and C13-skeletons were found in the title plant. The possible biogenetic relationships of these degraded terpenoids were briefly discussed. Among the isolates, pseudosinin D, cis-communic acid, and 4ß,15-dihydroxy-19-norabieta-8,11,13-trien-7-one showed moderate inhibitory activities against the enzyme ATP-citrate lyase (ACL), a potential drug target for the treatment of hyperlipidemia and hypercholesterolemia.


Assuntos
ATP Citrato (pro-S)-Liase/antagonistas & inibidores , Diterpenos/farmacologia , Inibidores Enzimáticos/farmacologia , Compostos Fitoquímicos/farmacologia , Pseudotsuga/química , Sesquiterpenos/farmacologia , ATP Citrato (pro-S)-Liase/metabolismo , China , Cristalografia por Raios X , Diterpenos/química , Diterpenos/isolamento & purificação , Relação Dose-Resposta a Droga , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Células HEK293 , Humanos , Modelos Moleculares , Conformação Molecular , NF-kappa B/antagonistas & inibidores , NF-kappa B/biossíntese , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Relação Estrutura-Atividade
17.
Org Lett ; 21(17): 6957-6960, 2019 09 06.
Artigo em Inglês | MEDLINE | ID: mdl-31403306

RESUMO

A cytochalasan, xylarichalasin A, was obtained from the endophytic fungus Xylaria cf. curta harbored in Solanum tuberosum. Its structure was elucidated by comprehensive spectroscopic methods including HRESIMS, 1D/2D NMR, and residual dipolar coupling analysis as well as quantum chemistry calculations including DFT GIAO 13C NMR and ECD calculation. It has an unprecedented 6/7/5/6/6/6 fused polycyclic structure. In bioassay, xylarichalasin A showed cytotoxicity against human cancer cell lines with IC50 value ranging from 6.3-17.3 µM.


Assuntos
Antineoplásicos/farmacologia , Citocalasinas/farmacologia , Xylariales/química , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Citocalasinas/química , Citocalasinas/isolamento & purificação , Teoria da Densidade Funcional , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Conformação Molecular , Estereoisomerismo , Relação Estrutura-Atividade
18.
Org Biomol Chem ; 17(34): 7985-7994, 2019 08 28.
Artigo em Inglês | MEDLINE | ID: mdl-31408074

RESUMO

Eleven new cytochalasins, curtachalasins F-P (1-11), were isolated from the rice fermentation of endophytic fungus Xylaria cf. curta. Their structures were identified by extensive spectroscopic methods, X-ray diffraction, and quantum chemistry calculations. Curtachalasin P possesses a unique 5/6/6/7 fused ring system. In the bioactivity screening for curtachalasins F-P, A-C, and E (1-15), compounds 1, 3-6, 8-13, and 15 did not show obvious cytotoxicity against primary mouse splenocytes. Furthermore, the immunosuppressive assay against concanavalin A (ConA) induced T lymphocyte cell proliferation and lipopolysaccharide (LPS) induced B lymphocyte cell proliferation showed that compound 1 results in significant selective inhibition on B-cell proliferation (IC50 value of 2.42 µM) and compound 10 has selective inhibition on T-cell proliferation (IC50 value of 12.15 µM). These interesting immunosuppressive properties of this class of compounds provide new clues to fulfill the urgent demand for new immunosuppressive drugs.


Assuntos
Citocalasinas/farmacologia , Imunossupressores/farmacologia , Xylariales/química , Animais , Linfócitos B/efeitos dos fármacos , Proliferação de Células/efeitos dos fármacos , Citocalasinas/química , Citocalasinas/isolamento & purificação , Imunossupressores/química , Imunossupressores/isolamento & purificação , Masculino , Camundongos Endogâmicos BALB C , Estrutura Molecular , Linfócitos T/efeitos dos fármacos
19.
Org Lett ; 21(15): 6145-6148, 2019 08 02.
Artigo em Inglês | MEDLINE | ID: mdl-31335156

RESUMO

Structurally unique thiopyranodipyridine alkaloids xylaridines C (1) and D (2) were isolated from the fungus Xylaria longipes. Their structures were established by comprehensive spectroscopic analysis combined with single-crystal X-ray diffraction and electron-capture detection (ECD) calculations. Compound 1 possesses two piperidine moieties fused with a centered thiopyran ring, while compound 2 is a dimer of 1. Compound 1 was resoluted into optical pure enatiomers (+)-1 and (-)-1 by chiral HPLC. Moreover, compound 2 was resoluted into an optically pure compound (+)-2 and a mixture of (-)-2 and meso-2. Plausible biosynthetic pathways of compounds 1 and 2 are proposed.


Assuntos
Alcaloides/química , Fungos/química , Xylariales/química , Vias Biossintéticas/fisiologia , Cristalografia por Raios X/métodos , Piranos/química , Compostos de Sulfidrila/química
20.
Fitoterapia ; 137: 104278, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31351910

RESUMO

Five new cytochalasans (1-5) were isolated from the rice fermentation of fungus Xylaria longipes, along with seven known compounds cytochalasin P (6), cytochalasin D (7), zygosporin D (8), 7-O-acetylcytochalasin D (9), cytochalasin C (10), 6,7-dihydro-7-oxo-cytochalasin C (11), and 6,7-dihydro-7-oxo-deacetylcytochalasin C (12). Their structures and absolute configurations were determined by extensive experimental spectroscopic methods as well as ECD calculation and GIAO 13C NMR calculation. The cytotoxicity of obtained compounds (1-12) was evaluated against human cancer cell lines HL-60, A549, SMMC-7721, MCF-7, and SW480. Compounds 6-8, 11, and 12 showed cytotoxicity with IC50 value ranging from 4.17-37.18 µM.


Assuntos
Antineoplásicos/farmacologia , Citocalasinas/farmacologia , Xylariales/química , Antineoplásicos/isolamento & purificação , Linhagem Celular Tumoral , China , Citocalasinas/isolamento & purificação , Humanos , Estrutura Molecular , Metabolismo Secundário
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