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1.
Sci Rep ; 14(1): 13001, 2024 06 06.
Artigo em Inglês | MEDLINE | ID: mdl-38844500

RESUMO

Achieving favorable seizure outcomes is challenging in patients with seizures resulting from hypothalamic hamartoma. Although minimally invasive and non-invasive surgical procedures are used to treat this population, these procedures have limitations. Therefore, we analyzed the outcomes of patients with hypothalamic hamartoma following direct resection. We included 159 patients with hypothalamic hamartoma who underwent direct resection using the transcallosal interforniceal approach between 2011 and 2018. The relationships between clinical parameters and seizure outcomes were analyzed. In total, 55.3% achieved gross total resection and 25.2% underwent near-total resection. Of all patients, 79.2% were overall seizure-free at one year, but this number dropped to 77.0% at more than five years. Moreover, 88.4% (129/146) reached gelastic seizure (GS)-free status at one year and this number increased to 89.0% (97/109) at more than five years. Seventy-one patients took antiseizure medication (ASM) long-term, 68 took it for one year, and 11 took it for one-half year. The duration of ASM consumption (p < 0.001) and extent of hypothalamic hamartoma resection (p = 0.016) were significant independent predictors of long-term overall seizure-free survival, while the duration of ASM consumption (p = 0.011) and extent of hypothalamic hamartoma resection (p = 0.026) were significant independent predictors of long-term GS-free survival. Most patients' behavior, school performance, and intelligence were not affected after surgery. Direct resection is effective and safe strategy for patients with hypothalamic hamartomas. Hypothalamic hamartomas should be removed as completely as possible, and patients should take ASM long-term following surgery to reach long-term overall seizure-free or GS-free status.


Assuntos
Hamartoma , Doenças Hipotalâmicas , Convulsões , Humanos , Hamartoma/cirurgia , Hamartoma/complicações , Doenças Hipotalâmicas/cirurgia , Doenças Hipotalâmicas/complicações , Feminino , Masculino , Convulsões/cirurgia , Criança , Pré-Escolar , Resultado do Tratamento , Adolescente , Lactente , Procedimentos Neurocirúrgicos/métodos , Procedimentos Neurocirúrgicos/efeitos adversos , Estudos Retrospectivos , Adulto , Adulto Jovem , Anticonvulsivantes/uso terapêutico
2.
Phytochemistry ; 222: 114108, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38663825

RESUMO

Twelve undescribed 2-(2-phenethyl)chromone dimers (1-12) were isolated from EtOAc extract of agarwood originating from Aquilaria filaria in the Philippines, guided by a UHPLC-MS analysis. Their structures were elucidated by 1D NMR, 2D NMR, and HR-ESI-MS spectra. The absolute configuration of 2-(2-phenylethyl)chromone dimers was determined by single-crystal X-ray diffraction analysis and comparison of the experimental and calculated ECD spectra. Compounds 1, 2, 5 and 9-12 exhibited potent to moderate anti-inflammatory activity with IC50 values in the range of 22.43 ± 0.86 to 53.88 ± 4.06 µM.


Assuntos
Cromonas , Thymelaeaceae , Madeira , Thymelaeaceae/química , Filipinas , Cromonas/química , Cromonas/isolamento & purificação , Cromonas/farmacologia , Estrutura Molecular , Madeira/química , Animais , Relação Estrutura-Atividade , Camundongos , Relação Dose-Resposta a Droga , Cristalografia por Raios X , Flavonoides
3.
J Asian Nat Prod Res ; 26(4): 489-496, 2024 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-37642432

RESUMO

Two new compounds named 3(S)-hydroxy-1-(2,4,5-trihydroxy-3,6- dimethylphenyl)-hex-4E-en-1-one (1) and acremonilactone (2), together with nine known compounds (3-11), were isolated from the fermentation broth of Acremonium sp. associated with marine sediments collected from South China Sea. NMR and HRESIMS spectroscopic analysis elucidated the structure of two new compounds. Compound 2 had characteristic rotary gate shape skeleton with a six-membered lactone. Compounds 1 and 9 showed DPPH radical scavenging activity with inhibition rates of 96.50 and 85.95% at the concentration of 0.5 mg/ml, respectively. Moreover, compounds 4, 6 and 11 showed definite antibacterial activity against Staphylococcus aureus ATCC 6538.


Assuntos
Acremonium , Acremonium/química , Estrutura Molecular , Fungos , Staphylococcus aureus , Espectroscopia de Ressonância Magnética , Antibacterianos/química
4.
Fitoterapia ; 172: 105748, 2024 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-37967770

RESUMO

Three new sesquiterpenoids, dendrohercoglin A - C (1-3), and one new bibenzyl derivative, dendronbiline D (4), together with nine known sesquiterpenoids (5-13) were isolated from Dendrobium hercoglossum. The structures of the new compounds were elucidated by extensive spectroscopic analysis as well as NMR and ECD calculations. All the compounds were evaluated for their neuroprotective and anti-inflammatory activities. Compounds 2 and 3 increased the H2O2-damaged SH-SY5Y cell viabilities from 43.3% to 58.6% and 68.4%, respectively. Compound 4 exhibited pronounced anti-inflammatory activity with IC50 value of 9.5 ± 0.45 µM which was superior to the reference compound quercetin (IC50: 15.7 ± 0.89 µM).


Assuntos
Bibenzilas , Dendrobium , Neuroblastoma , Sesquiterpenos , Humanos , Dendrobium/química , Estrutura Molecular , Peróxido de Hidrogênio , Espectroscopia de Ressonância Magnética , Sesquiterpenos/farmacologia , Bibenzilas/farmacologia , Bibenzilas/química , Anti-Inflamatórios/farmacologia
5.
Molecules ; 28(9)2023 Apr 27.
Artigo em Inglês | MEDLINE | ID: mdl-37175165

RESUMO

Mangrove-associated fungi are important sources for the discovery of new bioactive natural products. Three new isocoumarins (1-3) and one new pyrone derivative (4) were isolated from the ethyl acetate extract of the fermentation broth of the mangrove endophytic fungus Phomopsis sp. DHS-11. Nuclear magnetic resonance (NMR) spectroscopy (one-dimensional and two-dimensional) and mass spectrometry were used to determine the structures of these new compounds. The absolute configurations for the new isocoumarins 1-3 were determined by comparing their experimental and calculated electronic circular dichroism (ECD) spectra, while the configuration for the new pyrone-derivative 4 was tentatively solved by comparison of its 13C NMR data with reported data. In the biological activity test, compounds 1 and 3 showed cytotoxic activity against HeLa cells with IC50 values of 11.49 ± 1.64 µM and 8.70 ± 0.94 µM, respectively. The initial structure and activity relationship (SAR) analysis revealed that the length of the side chain at C-3 for isocoumarin-type compounds 1-3 could affect the cytotoxicity against HeLa cells. Compound 4 exhibited cytotoxic activities against human hepatoma cells HepG2 with an IC50 value of 34.10 ± 2.92 µM. All compounds have no immunosuppressive activity.


Assuntos
Antineoplásicos , Rhizophoraceae , Humanos , Antineoplásicos/farmacologia , Fungos , Células HeLa , Isocumarinas/química , Estrutura Molecular , Phomopsis , Pironas/farmacologia , Rhizophoraceae/microbiologia
6.
Mar Drugs ; 21(3)2023 Feb 25.
Artigo em Inglês | MEDLINE | ID: mdl-36976199

RESUMO

Five new isocoumarins, phaeosphaerins A-E (1-5), were isolated from the fermentation broth of the marine fungus Phaeosphaeriopsis sp. WP-26, along with one known isocoumarin, 6,8-dihydroxy-7-methoxy-3-methylisocoumarin (6), and two known pimarane-type diterpenes, diaportheins A (7) and B (8). Their structures were elucidated via NMR experiments, X-ray diffraction analysis, and comparison of the experimental and computed ECD curves. Compounds 1-7 displayed weak neuroprotective effects against H2O2-induced damage in SH-SY5Y cells. Moreover, compound 8 showed cytotoxicity against BEL-7402, SGC-7901, K562, A549, and HL-60 cell lines.


Assuntos
Ascomicetos , Neuroblastoma , Humanos , Isocumarinas/química , Peróxido de Hidrogênio , Ascomicetos/química , Espectroscopia de Ressonância Magnética , Abietanos , Estrutura Molecular
7.
Fitoterapia ; 165: 105422, 2023 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-36592638

RESUMO

Four new 2-(2-phenethyl)chromone dimers (1-4) were isolated from EtOAc extract of agarwood originating from Aquilaria filaria from Philippines. Their structures were elucidated by spectroscopic analysis (1D and 2D NMR, and HRESIMS) and comparison of the experimental and computed ECD curves. Compounds 1-4 exhibited inhibition of nitric oxide production in lipopolysaccharide-stimulated RAW264.7 cells with IC50 values in the range from 33.94 to 57.53 µM.


Assuntos
Cromonas , Thymelaeaceae , Cromonas/farmacologia , Estrutura Molecular , Thymelaeaceae/química , Espectroscopia de Ressonância Magnética , Lipopolissacarídeos , Flavonoides/química
8.
Fitoterapia ; 165: 105421, 2023 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-36587748

RESUMO

Two rare flavonoid-2-(2-phenylethyl)chromones and five new dimeric 2-(2-phenylethyl)chromones were isolated from ethanol extract of agarwood of Aquilaria walla by LC-MS-guided fractionation procedure. Their structures were established based on extensive spectroscopic methods including HRESIMS, 1D and 2D NMR, as well as by comparison with the literature. Compound 1 showed cytotoxic activity against five human cancer cell lines with IC50 values ranging from 13.40 to 28.96 µM with cisplatin as the positive control.


Assuntos
Cromonas , Thymelaeaceae , Humanos , Cromonas/farmacologia , Thymelaeaceae/química , Estrutura Molecular , Flavonoides/química , Espectrometria de Massas , Madeira/química
9.
Fitoterapia ; 158: 105162, 2022 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-35217119

RESUMO

Six new 2-(2-phenylethyl)chromone dimers (1-6) were isolated from ethyl ether extract of red soil agarwood of Aquilaria crassna from Vietnam by LC-MS-guided fractionation procedure. Their structures were unambiguously elucidated based on HRESIMS, 1D and 2D NMR spectra. The absolute configuration of 2-(2-phenylethyl)chromone dimers was determined by comparison of the experimental and computed ECD spectra. Compound 6 displayed cytotoxicity against the human myeloid leukemia cell line (K562) with an IC50 value of 39.49 µM.


Assuntos
Cromonas , Thymelaeaceae , Cromatografia Líquida , Cromonas/química , Flavonoides/química , Humanos , Estrutura Molecular , Solo , Espectrometria de Massas em Tandem , Thymelaeaceae/química , Madeira/química
10.
Nat Prod Res ; 36(8): 2112-2117, 2022 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-33331167

RESUMO

A picrotoxane-type sesquiterpene, dendroterpene E (1), together with five benzene derivatives (2-6), were isolated from the stems of Dendrobium nobile Lindl. Their structures were elucidated by spectroscopic analysis and X-ray diffraction analysis. Compound 1 was a new picrotoxane-type sesquiterpene with a C-9/C-1/O/C-11 oxetane ring, which was first encountered in this type of compounds. Compounds 1-3 exhibited inhibitory activities against α-glycosidase.


Assuntos
Dendrobium , Sesquiterpenos , Dendrobium/química , Estrutura Molecular , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Análise Espectral
11.
J Nat Prod ; 85(1): 3-14, 2022 01 28.
Artigo em Inglês | MEDLINE | ID: mdl-34935371

RESUMO

Chemical investigation of an alcoholic extract from the stem of Daphne papyracea ("Xuehuagou") led to the isolation of the tetracyclic sesquiterpenoid daphnepapytone A (1), containing a unique caged skeleton with a cyclobutane ring having three tetrasubstituted chirality centers. Also isolated were new guaiane sesquiterpenoids, namely, daphnepapytones B-H (2-8), and one 1,5-diphenylpentanone 2-hydroxy-5-oxo-daphneone (9), together with 26 known compounds. The cyclic metabolites share a 5-isoprenyl-hexahydroazulene-2(1H)-one skeleton with different substitution patterns and a bridged cyclobutane, oxetane, or tetrahydrofuran ring. The planar structures and relative configuration of the new compounds were elucidated on the basis of spectroscopic analysis aided by DFT 13C NMR calculations. The absolute configurations of 1-7 were determined by X-ray single-crystal diffraction or TDDFT-ECD calculations. Daphnepapytones A and C (1 and 3), 2-hydroxy-5-oxodaphneone (9), daphnenone (10), daphneone (11), and 3-methyldaphneolone (12) showed α-glycosidase inhibitory activity, with IC50 values of 159.0, 102.3, 139.3, 43.3, 145.0, and 126.1 µM, respectively.


Assuntos
Ciclobutanos/química , Daphne/química , Éteres Cíclicos/química , Furanos/química , Inibidores de Glicosídeo Hidrolases/química , Inibidores de Glicosídeo Hidrolases/farmacologia , Caules de Planta/química , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Espectroscopia de Ressonância Magnética Nuclear de Carbono-13 , Cristalografia por Raios X , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Estrutura Molecular , Sesquiterpenos/isolamento & purificação , Estereoisomerismo
12.
Molecules ; 26(2)2021 Jan 15.
Artigo em Inglês | MEDLINE | ID: mdl-33467706

RESUMO

Recently, cultivated "Qi-Nan" (CQN) agarwood has emerged as a new high-quality agarwood in the agarwood market owing to its similar characteristics, such as high content of resin and richness in two 2-(2-phenylethyl)chromone derivatives, 2-(2-phenylethyl)chromone (59) and 2-[2-(4-methoxyphenyl)ethyl]chromone (60), to the wild harvested "Qi-Nan" (WQN) agarwood. In this study, we compared the chemical constituents and fragrant components of two types of WQN agarwood from A. agallocha Roxb. and A. sinensis, respectively, with CQN agarwood and ordinary agarwood varieties. Additionally, we analyzed different samples of WQN agarwood and CQN agarwood by GC-MS, which revealed several noteworthy differences between WQN and CQN agarwood. The chemical diversity of WQN was greater than that of CQN agarwood. The content of (59) and (60) was higher in CQN agarwood than in WQN agarwood. For the sesquiterpenes, the richness and diversity of sesquiterpenes in WQN agarwood, particularly guaiane and agarofuran sesquiterpenes, were higher than those in CQN. Moreover, guaiane-furans sesquiterpenes were only detected by GC-MS in WQN agarwood of A. sinensis and could be a chemical marker for the WQN agarwood of A. sinensis. In addition, we summarized the odor descriptions of the constituents and established the correlation of scents and chemical constituents in the agarwood.


Assuntos
Flavonoides/química , Sesquiterpenos/química , Thymelaeaceae/química , Madeira/química , Flavonoides/análise , Estrutura Molecular , Odorantes/análise , Perfumes/análise , Perfumes/química , Sesquiterpenos/análise
13.
J Asian Nat Prod Res ; 23(2): 117-122, 2021 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-31979983

RESUMO

Two new compounds named asperpenes D (1) and E (2) were isolated from the marine-derived fungus Aspergillus sp. SCS-KFD66. Their structures were determined on the basis of spectroscopic methods. Compound 2 represents the first natural product bearing a 2-substituted-5-oxo-4-phenyl-2,5-dihydrofuran-3-carboxylic acid skeleton. All the compounds were tested for enzyme inhibitory activity against AChE and α-glucosidase and DPPH radical scavenging activity, respectively. [Formula: see text].


Assuntos
Produtos Biológicos , Bivalves , Animais , Aspergillus , Estrutura Molecular , alfa-Glucosidases
14.
Molecules ; 27(1)2021 Dec 29.
Artigo em Inglês | MEDLINE | ID: mdl-35011431

RESUMO

Nine new sesquiterpenoids (1-9) were isolated from ethyl ether extract of agarwood originated from Aquilaria sp., including three novel sesquiterpenoids (1-3) derived from zizaane, together with six zizaane-type sesquiterpenoids (4-9). All structures were unambiguously elucidated based on 1D and 2D NMR spectra as well as by HRESIMS data. The absolute configuration of sesquiterpenoids was determined by comparison of the experimental and computed ECD spectra. In vitro anti-inflammatory assessment showed that compound 9 exhibited inhibition of NO production in LPS-stimulated RAW264.7 cells with an IC50 value of 62.22 ± 1.27 µM.


Assuntos
Sesquiterpenos/química , Thymelaeaceae/química , Madeira/química , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Sobrevivência Celular/efeitos dos fármacos , Fenômenos Químicos , Espectroscopia de Ressonância Magnética , Camundongos , Estrutura Molecular , Células RAW 264.7 , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia
15.
Front Chem ; 9: 773703, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-34976948

RESUMO

Two new benzoic acids, cladoslide A (1) and cladoslide B (2); one new ß-carboline derivative, cladospomine (3); and one new pyridin-2(1H)-one, cladoslide C (4), were isolated from the fermentation cultures of the mangrove-derived fungus Cladosporium sp. HNWSW-1, along with the previously reported N-acetyl-ß-oxotryptamine (5), (4S,5S,11R)-iso-cladospolide B (6), (4S,5S,11S)-iso-cladospolide B (7), and (4R,5S,11R)-iso-cladospolide B (8). Their structures were elucidated by spectroscopic analysis, Rh2(OCOCF3)4-induced ECD experiments, and Marfey's method. Compound 1 showed cytotoxicity against the K562 cell line with IC50 values of 13.10 ± 0.08 µM. Moreover, compounds 1 and 5 exhibited inhibitory activity against α-glycosidase with IC50 values of 0.32 ± 0.01 mM and 0.17 ± 0.01 mM, respectively.

16.
J Asian Nat Prod Res ; 23(11): 1030-1036, 2021 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-33225746

RESUMO

Two new compounds named epipaxilline (1) and penerpene J (2) were isolated from the marine-derived fungus Penicillium sp. KFD28. Their structures including absolute configurations were determined on the basis of spectroscopic methods and ECD analysis. Compounds 1 and 2 showed inhibitory activities against PTP1B with IC50 values of 31.5 and 9.5 µM, respectively, and compound 2 also showed inhibitory activities against TCPTP with IC50 value of 14.7 µM.


Assuntos
Diterpenos , Penicillium , Fungos , Indóis , Estrutura Molecular
17.
Phytochemistry ; 181: 112578, 2021 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-33171341

RESUMO

Twelve undescribed 2-(2-phenylethyl)chromone derivatives, including one pair of enantiomers, together with eleven known ones, were isolated from the EtOAc extract of agarwood originating from Aquilaria filaria. All structures were elucidated by spectroscopic (NMR, UV, IR, MS) methods and compared with reported data in literatures. Twenty-one compounds were assessed for α-glucosidase inhibitory activity, which showed inhibition of α-glucosidase with IC50 values ranging between 7.8 ± 0.3 to 137.7 ± 3.0 µM (Acarbose, 743.4 ± 3.3 µM; Genistein, 8.3 ± 0.1 µM). Our results expanded the structural diversity of 2-(2-phenylethyl)chromones from agarwood, and revealed the potential of 2-(2-phenylethyl)chromones as α-glucosidase inhibitors.


Assuntos
Inibidores de Glicosídeo Hidrolases , Thymelaeaceae , Cromonas/farmacologia , Flavonoides , Inibidores de Glicosídeo Hidrolases/farmacologia , Estrutura Molecular
18.
Fitoterapia ; 143: 104557, 2020 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-32198109

RESUMO

Five new sesquiterpenoids (1-5), together with a known compound 6 was isolated from ethyl ether extract of agarwood. Their structures were elucidated on the basis of spectroscopic techniques (UV, IR, MS, 1D and 2D NMR), as well as by comparison with literature data. Compound 5 exhibited inhibitory activity against acetylcholinesterase with inhibition ratio of 48.33 ± 0.17% at the concentration of 50 µg/mL.


Assuntos
Sesquiterpenos/química , Thymelaeaceae/química , Madeira/química , Inibidores da Colinesterase/química , Inibidores da Colinesterase/isolamento & purificação , Ésteres/química , Estrutura Molecular , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Extratos Vegetais/química , Sesquiterpenos/isolamento & purificação , Tailândia
19.
J Nat Prod ; 82(12): 3456-3463, 2019 12 27.
Artigo em Inglês | MEDLINE | ID: mdl-31823605

RESUMO

Seven new quinazoline-containing indole alkaloids (1-7) named aspertoryadins A-G, along with nine known ones (8-16), were isolated from the marine-derived fungus Aspergillus sp. HNMF114 from the bivalve mollusk Sanguinolaria chinensis. The structures of the new compounds were elucidated from spectroscopic data, X-ray diffraction analysis, ECD spectra analysis, and ECD calculations. Compound 1 bears an aminosulfonyl group in the structure, which is rarely encountered in natural products. Compounds 6, 7, and 13 exhibited quorum sensing inhibitory activity against Chromobacterium violaceum CV026 with MIC values of 32, 32, and 16 µg/well, respectively.


Assuntos
Aspergillus/química , Alcaloides Indólicos/farmacologia , Quinazolinas/farmacologia , Água do Mar/microbiologia , Alcaloides Indólicos/química , Alcaloides Indólicos/isolamento & purificação , Testes de Sensibilidade Microbiana , Estrutura Molecular , Quinazolinas/química , Quinazolinas/isolamento & purificação , Percepção de Quorum/efeitos dos fármacos
20.
Front Chem ; 7: 812, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31850306

RESUMO

Four picrotoxane-type sesquiterpenes, dendroterpene A-D (1-4), together with four known compounds (5-8), were isolated from the stems of Dendrobium nobile Lindl. Their structures were elucidated by spectroscopic analysis, X-ray diffraction analysis, analysis of the ECD data according to the Klyne's lactone sector rule, and quantum ECD calculation. Compounds 1 and 2 are two new picrotoxane-type sesquiterpenes with a new carbon skeleton containing a formamide group, which may be derived from the previously reported dendrobiumane B skeleton by the C(9)-C(11) carbon bond cleavage. Compounds 3, 5, 6, and 8 exhibited inhibitory activity against α-glycosidase. Compounds 5 and 6 were cytotoxic against SGC-7901, K562, A549, BEL-7402, and Hela cell lines.

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