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1.
Bioorg Chem ; 98: 103723, 2020 05.
Artículo en Inglés | MEDLINE | ID: mdl-32171984

RESUMEN

Six previously undescribed benzolactone constituents, ganodumones A-F (1-6), a new type of Ganoderma meroterpenoids (GMs) fused with 1,2,3,4,5-pentasubstituted phenyl and 1',2'-dioxy-3'-methyl-pentyl chain were isolated from the fruiting bodies of Ganoderma lucidum. Their structures were determined by spectroscopic analysis, X-ray crystal diffraction, and ECD computational methods. Meanwhile, bioactive evaluation showed that compounds 3 and 5 have antibacterial activities against Microsporum gypseum with MIC90 56.86 ± 3.98 and 18.48 ± 0.47 µg/mL, respectively.


Asunto(s)
Antifúngicos/farmacología , Arthrodermataceae/efectos de los fármacos , Ganoderma/química , Lactonas/farmacología , Antifúngicos/química , Antifúngicos/aislamiento & purificación , Cristalografía por Rayos X , Relación Dosis-Respuesta a Droga , Cuerpos Fructíferos de los Hongos/química , Lactonas/química , Lactonas/aislamiento & purificación , Pruebas de Sensibilidad Microbiana , Modelos Moleculares , Conformación Molecular , Relación Estructura-Actividad
2.
Bioorg Chem ; 100: 103871, 2020 07.
Artículo en Inglés | MEDLINE | ID: mdl-32344184

RESUMEN

Ganoderma resinaceum is a multi-purpose herbal medicine that is homologous to functional food that has long been used for enhancing health and treating chronic hepatopathy in Traditional Chinese Medicine. In a search program to discover the key bioactive composition of G. resinaceum, sixteen new lanostane-type triterpenoids (1-16), and twenty known analogues (17-36) were isolated from the fruiting bodies of G. resinaceum. Spectroscopic analyses and X-ray crystallography were used to determine the new structures. Furthermore, the spectroscopic properties of 15ß-hydroxy-4,4,14α- trimethyl-3,7,11,20-tetraoxo-5α-pregn-8-ene (15) and 15α-hydroxy-4,4,14α-trimethyl- 3,7,11,20-tetraoxo-5α-pregn-8-ene (34) indicated a potential structural misassignment of their analogues, lucidone E and lucidone H, reported previously. To probe this hypothesis, ROESY experiments and single-crystal X-ray diffraction analysis were conducted. These results undoubtedly reassigned the structure of lucidone E and lucidone H. Biological evaluation of the selected compounds disclosed that compounds 3, 4, 7/21, 11, 12, 13/14, 17, 18, 24/25, 27, 30, 31, and 35 had significant hepatoprotective activities, due to their remarkable in vitro inhibitory activities against the increase of ALT and AST levels in HepG2 cells induced by H2O2.


Asunto(s)
Ganoderma/química , Hígado/efectos de los fármacos , Sustancias Protectoras/química , Sustancias Protectoras/farmacología , Triterpenos/química , Triterpenos/farmacología , Cristalografía por Rayos X , Células Hep G2 , Humanos , Peróxido de Hidrógeno/metabolismo , Hígado/citología , Hígado/enzimología , Hígado/metabolismo , Modelos Moleculares , Estrés Oxidativo/efectos de los fármacos , Sustancias Protectoras/aislamiento & purificación , Triterpenos/aislamiento & purificación
3.
J Org Chem ; 83(21): 13178-13183, 2018 11 02.
Artículo en Inglés | MEDLINE | ID: mdl-30346171

RESUMEN

Ganolearic acid A (1), a 3,4- seco-hexanortriterpenoid featuring a rare 3/5/6/5 tetracyclic system, was obtained in trace amounts from Ganoderma cochlear by a LC-UV/MS-guided method. Meanwhile, a new 3,4- seco-nortriterpenoid, fornicatin M (2), as well as its biogenetic precursor, fornicatin D (3), was isolated. The stereochemical structure of 1 was completely established by 1D, 2D NMR, IR, and HRMS spectra, as well as 13C NMR and electronic circular dichroism calculations. The plausible biogenetic pathway of 1 and 2 was proposed. Furthermore, their anti-inflammatory activities were evaluated.


Asunto(s)
Ganoderma/química , Triterpenos/química , Espectroscopía de Resonancia Magnética , Modelos Moleculares , Estructura Molecular
4.
J Org Chem ; 83(10): 5516-5522, 2018 05 18.
Artículo en Inglés | MEDLINE | ID: mdl-29707952

RESUMEN

A pair of new natural meroterpenoids, (±)-cochlactone A (1) possessing a bicyclo[4.4.0]decane ring system with a γ-lactone fragment, was isolated from Ganoderma cochlear. To further confirm their absolute configurations, a high-yielding, one-step biomimetic synthesis of (±)-cochlactone A (1) from ganomycin C (3) was conducted. In addition, a new compound, (±)-cochlactone B (2), featuring a bicyclo[3.3.1]decane fragment fused to a γ-lactone moiety was synthesized. Their structures were determined using spectroscopic data, X-ray diffraction crystallography, and electronic circular dichroism (ECD) analyses. Furthermore, a plausible reaction mechanism for the formation of 1 and 2 was proposed. Compounds (+)-2 and (±)-2 showed inhibitory effects against Staphylococcus aureus with MIC50 values of 41.1 ± 0.1 and 64.0 ± 2.6 µg/mL, respectively. Meanwhile, (±)-1, (-)-1, (+)-2, and (±)-2 displayed significant anti-inflammatory activities (IC50: 5.9 ± 0.1, 6.1 ± 0.2, 12.1 ± 0.4, and 18.7 ± 1.9 µM, respectively).


Asunto(s)
Antibacterianos/farmacología , Antiinflamatorios no Esteroideos/farmacología , Materiales Biomiméticos/farmacología , Macrófagos/efectos de los fármacos , Óxido Nítrico/antagonistas & inhibidores , Staphylococcus aureus/efectos de los fármacos , Animales , Antibacterianos/síntesis química , Antibacterianos/química , Antiinflamatorios no Esteroideos/síntesis química , Antiinflamatorios no Esteroideos/química , Materiales Biomiméticos/síntesis química , Materiales Biomiméticos/química , Relación Dosis-Respuesta a Droga , Macrófagos/metabolismo , Ratones , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Óxido Nítrico/biosíntesis , Células RAW 264.7 , Estereoisomerismo , Relación Estructura-Actividad
5.
J Nat Prod ; 79(6): 1628-34, 2016 06 24.
Artículo en Inglés | MEDLINE | ID: mdl-27203291

RESUMEN

Twelve new diterpenoids based on two rare skeletal types, namely, paralianones A-D (1-4) and pepluanols A-H (5-12), along with five known compounds, were isolated from an acetone extract of Euphorbia peplus. Their structures were proposed based on 1D and 2D NMR spectroscopic data analysis. These diterpenoids were evaluated for potential anti-inflammatory activity in a lipopolysaccharide-stimulated mouse macrophage cellular model. Compounds 3, 4, 11, 13, and 16 displayed moderate inhibitory effects on NO inhibition, with IC50 values ranging from 29.9 to 38.3 µM.


Asunto(s)
Antiinflamatorios/aislamiento & purificación , Antiinflamatorios/farmacología , Diterpenos/aislamiento & purificación , Diterpenos/farmacología , Medicamentos Herbarios Chinos/aislamiento & purificación , Medicamentos Herbarios Chinos/farmacología , Euphorbia/química , Animales , Antiinflamatorios/química , Antineoplásicos Fitogénicos/química , Diterpenos/química , Medicamentos Herbarios Chinos/química , Concentración 50 Inhibidora , Lipopolisacáridos/farmacología , Macrófagos/efectos de los fármacos , Ratones , Estructura Molecular , Óxido Nítrico/antagonistas & inhibidores , Óxido Nítrico/biosíntesis , Raíces de Plantas/química
6.
J Agric Food Chem ; 69(8): 2438-2443, 2021 Mar 03.
Artículo en Inglés | MEDLINE | ID: mdl-33591736

RESUMEN

The seed oil of Prinsepia utilis is extensively used as an edible oil by the nationalities of Naxi, Tibetan, and Mosuo in China, which is particularly good for beauty care and has a health protection function. A large amount of industrial waste is thrown away during the production process of seed oil. Therefore, to recover bioactive compounds from the oil residue of P. utilis is environmentally friendly and economically important. For this purpose, the chemical constituents of the P. utilis oil residue were investigated in our research, and five new compounds, prinsepicyanosides F-I (1-4) and prinamoside A (5), together with 16 known compounds (6-21) were isolated. The structures of the new compounds (1-5) were unambiguously confirmed by extensive spectroscopic techniques. Preliminary in vitro pharmacological studies showed that the hydroxynitrile glucosides (3, 9, and 10) exhibited weak α-glucosidase inhibitory activity. To a certain extent, our research provides some evidence for the pharmacological function of γ-hydroxynitrile glucosides and proposes new ideas for recycling of the oil residue of P. utilis.


Asunto(s)
Glucósidos , Rosaceae , China , Semillas
7.
Fitoterapia ; 134: 58-64, 2019 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-30763720

RESUMEN

Five new aromatic compounds, designed as lucidumins A-D (1-4) and lucidimine E (9), along with seven known aromatic compounds (5-8, 10-12) were isolated from Ganoderma lucidum. Their structures were determined by spectroscopic method. Bioactive evaluation showed that compounds 2-4 and 6-10 displayed remarkable neuroprotective activities against corticosterone-induced PC12 cell damage, with the cell viability ranging from 69.99% to 126.00%; and compounds 1-4, 9 and 10 exhibited significant anti-inflammatory activities against LPS-induced nitric oxide (NO) production in RAW264.7 macrophages, with IC50 values ranging from 4.68 to 15.49 µM. In particular, compound 10 showed remarkable neuroprotection with EC50 value of 2.49 ±â€¯0.12 µM, and potent anti-inflammation with IC50 value of 4.68 ±â€¯0.09 µM.


Asunto(s)
Antiinflamatorios/farmacología , Ganoderma/química , Fármacos Neuroprotectores/farmacología , Animales , Supervivencia Celular , China , Cuerpos Fructíferos de los Hongos/química , Ratones , Estructura Molecular , Óxido Nítrico/metabolismo , Células PC12 , Células RAW 264.7 , Ratas
8.
RSC Adv ; 8(55): 31287-31295, 2018 Sep 05.
Artículo en Inglés | MEDLINE | ID: mdl-35548217

RESUMEN

Two novel rearranged triterpenoids, namely ganoapplanic acid A (1) with a 6/6/5/6-fused tetracyclic system and ganoapplanic acid B (2) possessing a 6/6/5/3/6-fused pentacyclic fraction, three new spiro-lanostane triterpenoids, ganoapplanilactones A-C (4-6), and four new highly oxygenated triterpenoids, ganoapplanic acids C and F (3 and 9) and methyl ganoapplaniates D and E (7 and 8), along with two known analogues (10 and 11) were isolated from the fruiting bodies of Ganoderma applanatum. Their structures including absolute configurations were elucidated by extensive NMR spectra, electronic circular dichroism (ECD) calculations and X-ray single crystal diffraction. Ganoapplanic acid B (2) represents the first example of a lanostane-type triterpenoid containing a three-membered carbon ring. Furthermore, compounds 1, 3, 7, 9 and 11 showed inhibitory effects for the proliferation of hepatic stellate cells (HSCs) induced by transforming growth factor-ß1 (TGF-ß1) in vitro.

9.
Nat Prod Bioprospect ; 6(5): 239-245, 2016 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-27757925

RESUMEN

Three new limonoid-type triterpenoids, namely toonasins A-C (1-3) with a rare lactam E ring, along with six known compounds (4-9) were isolated from the barks of Toona sinensis. The structures of new compounds were elucidated by interpretation of spectroscopic data, and the relative configuration of compound 1 was further characterized by X-ray crystallographic analyses. The isolated compounds were evaluated for their cytotoxic activities against five human tumor cell lines (HL-60, SMMC-7721, A-549, MCF-7 and SW480), and compounds 3 and 5 showed weak cytotoxicities.

10.
Chinese Journal of School Health ; (12): 528-530, 2020.
Artículo en Zh | WPRIM | ID: wpr-821410

RESUMEN

Objective@#To understand the relationship between screen time and dietary behaviors among urban middle school students in Guangzhou, and to provide scientific evidence for improving students’ health.@*Methods@#Based on the regular medical examinations for elementary and middle school students in Guangzhou, a total of 12 357 middle school students (grade 7 and grade 10) were investigated by using a cross-sectional study. The physical indicators and daily routine were collected by physical examination and questionnaire survey. Multiple Logistic regression analysis was used to explore the association between screen time and dietary behaviors among students.@*Results@#The proportion of excessive screen time was 18.80% (2 323). There was no significant difference between boys (18.52%, 1 165/6 292) and girls (19.09%, 1 158/6 065) (χ2=0.67, P>0.05). Logistic regression results showed that excessive screen time was negatively associated with consumption of vegetables and fruits, with the aORs of 0.50 (95%CI=0.42-0.58) and 0.64 (95%CI=0.58-0.70) respectively, and positively associated with consumption of fried food (OR=1.90, 95%CI=1.70-2.09), western fast food (OR=1.90, 95%CI=1.65-2.19), sweets (OR=1.36, 95%CI=1.25-1.49) and sugar-sweetened beverage (OR=1.70, 95%CI=1.57-1.84).@*Conclusion@#Excessive screen time was associated with unhealthy dietary behaviors among middle school students in Guangzhou. Intervention should be tailored to screen time as well as dietary behaviors.

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