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Medicinas Complementárias
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1.
Zhongguo Zhong Yao Za Zhi ; 49(3): 728-734, 2024 Feb.
Artículo en Chino | MEDLINE | ID: mdl-38621876

RESUMEN

Mesona chinensis is a common medicinal and edible plant in the Lingnan region of China, which has extensive pharmacological activity. However, the study of its chemical constituents is not sufficient. In this study, a variety of modern chromatographic separation techniques were used to isolate two compounds from 95% ethanol extract of the grass parts of M. chinensis. Their absolute configurations were determined by ultraviolet spectroscopy(UV), infrared spectroscopy(IR), high resolution mass spectrometry(HR-ESI-MS), 1D and 2D nuclear magnetic resonance(1D NMR and 2D NMR), and single-crystal X-ray diffraction(SC-XRD). Specifically, they were two new benzoyl-sesquiterpenes and named mesonanol A and mesonanol B, respectively. The results of the pharmacological activity evaluation showed that neither of the two new compounds showed obvious antiviral and anti-inflammatory activities.


Asunto(s)
Lamiaceae , Sesquiterpenos , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Espectrofotometría Infrarroja , Estructura Molecular
2.
Phytochemistry ; 222: 114103, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38636686

RESUMEN

Eight new cytochalasans rosellichalasins A-H (1-8), as well as two new shunt metabolites rosellinins A (9) and B (10) before intramolecular Diels-Alder cycloaddition reaction in cytochalasan biosynthesis, along with nine known cytochalsans (11-19) were isolated from the endophytic fungus Rosellinia sp. Glinf021, which was derived from the medicinal plant Glycyrrhiza inflata. Their structures were characterized by extensive analysis of 1D and 2D NMR as well as HRESIMS spectra and quantum chemical ECD calculations. The cytotoxic activities of these compounds were evaluated against four human cancer cell lines including HCT116, MDA-MB-231, BGC823, and PANC-1 with IC50 values ranging from 0.5 to 58.2 µM.


Asunto(s)
Antineoplásicos , Citocalasinas , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Citocalasinas/química , Citocalasinas/farmacología , Citocalasinas/aislamiento & purificación , Estructura Molecular , Línea Celular Tumoral , Antineoplásicos/farmacología , Antineoplásicos/química , Antineoplásicos/aislamiento & purificación , Ascomicetos/química , Relación Estructura-Actividad , Proliferación Celular/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Endófitos/química
3.
Phytochemistry ; 222: 114096, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38641141

RESUMEN

Forsythiae Fructus (FF), the dried fruit of F. suspensa, is commonly used to treat fever, inflammation, etc in China or other Asian countries. FF is usually used as the core herb in traditional Chinese medicine preparations for the treatment of influenza, such as Shuang-huang-lian oral liquid and Yin-qiao powder, etc. Since the wide application and core role of FF, its research progress was summarized in terms of traditional uses, phytochemistry, pharmacology, pharmacokinetics, quality control, and toxicity. Meanwhile, the anti-influenza substances and mechanism of FF were emphasized. Till now, a total of 290 chemical components are identified in F. suspensa, and among them, 248 components were isolated and identified from FF, including 42 phenylethanoid glycosides, 48 lignans, 59 terpenoids, 14 flavonoids, 3 steroids, 24 cyclohexyl ethanol derivatives, 14 alkaloids, 26 organic acids, and 18 other types. FF and their pure compounds have the pharmacological activities of anti-virus, anti-inflammation, anti-oxidant, anti-bacteria, anti-tumor, neuroprotection, hepatoprotection, etc. Inhibition of TLR7, RIG-I, MAVS, NF-κB, MyD88 signaling pathway were the reported anti-influenza mechanisms of FF and phenylethanoid glycosides and lignans are the main active groups. However, the bioavailability of phenylethanoid glycosides and lignans of FF in vivo was low, which needed to be improved. Simultaneously, the un-elucidated compounds and anti-influenza substances of FF strongly needed to be explored. The current quality control of FF was only about forsythoside A and phillyrin, more active components should be taken into consideration. Moreover, there are no reports of toxicity of FF yet, but the toxicity of FF should be not neglected in clinical applications.


Asunto(s)
Forsythia , Control de Calidad , Forsythia/química , Humanos , Frutas/química , Fitoquímicos/farmacología , Fitoquímicos/química , Fitoquímicos/aislamiento & purificación , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/farmacología , Medicamentos Herbarios Chinos/aislamiento & purificación , Animales , Estructura Molecular
4.
Inorg Chem ; 63(16): 7464-7472, 2024 Apr 22.
Artículo en Inglés | MEDLINE | ID: mdl-38598182

RESUMEN

Uranium accumulation in the kidneys and bones following internal contamination results in severe damage, emphasizing the pressing need for the discovery of actinide decorporation agents with efficient removal of uranium and low toxicity. In this work, cinnamic acid (3-phenyl-2-propenoic acid, CD), a natural aromatic carboxylic acid, is investigated as a potential uranium decorporation ligand. CD demonstrates markedly lower cytotoxicity than that of diethylenetriaminepentaacetic acid (DTPA), an actinide decorporation agent approved by the FDA, and effectively removes approximately 44.5% of uranyl from NRK-52E cells. More importantly, the results of the prompt administration of the CD solution remove 48.2 and 27.3% of uranyl from the kidneys and femurs of mice, respectively. Assessments of serum renal function reveal the potential of CD to ameliorate uranyl-induced renal injury. Furthermore, the single crystal of CD and uranyl compound (C9H7O2)2·UO2 (denoted as UO2-CD) reveals the formation of uranyl dimers as secondary building units. Thermodynamic analysis of the solution shows that CD coordinates with uranyl to form a 2:1 molar ratio complex at a physiological pH of 7.4. Density functional theory (DFT) calculations further show that CD exhibits a significant 7-fold heightened affinity for uranyl binding in comparison to DTPA.


Asunto(s)
Cinamatos , Uranio , Cinamatos/química , Cinamatos/farmacología , Animales , Ligandos , Ratones , Uranio/química , Uranio/metabolismo , Uranio/toxicidad , Riñón/efectos de los fármacos , Riñón/metabolismo , Línea Celular , Teoría Funcional de la Densidad , Ratas , Estructura Molecular , Supervivencia Celular/efectos de los fármacos , Quelantes/química , Quelantes/farmacología , Quelantes/síntesis química
5.
Chin J Nat Med ; 22(4): 365-374, 2024 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-38658099

RESUMEN

Phorbol esters are recognized for their dual role as anti-HIV-1 agents and as activators of protein kinase C (PKC). The efficacy of phorbol esters in binding with PKC is attributed to the presence of oxygen groups at positions C20, C3/C4, and C9 of phorbol. Concurrently, the lipids located at positions C12/C13 are essential for both the anti-HIV-1 activity and the formation of the PKC-ligand complex. The influence of the cyclopropane ring at positions C13 and C14 in phorbol derivatives on their anti-HIV-1 activity requires further exploration. This research entailed the hydrolysis of phorbol, producing seco-cyclic phorbol derivatives. The anti-HIV-1 efficacy of these derivatives was assessed, and the affinity constant (Kd) for PKC-δ protein of selected seco-cyclic phorbol derivatives was determined through isothermal titration calorimetry. The findings suggest that the chemical modification of cyclopropanols could affect both the anti-HIV-1 activity and the PKC binding affinity. Remarkably, compound S11, with an EC50 of 0.27 µmol·L-1 and a CC50 of 153.92 µmol·L-1, demonstrated a potent inhibitory effect on the intermediate products of HIV-1 reverse transcription (ssDNA and 2LTR), likely acting at the viral entry stage, yet showed no affinity for the PKC-δ protein. These results position compound S11 as a potential candidate for further preclinical investigation and for studies aimed at elucidating the pharmacological mechanism underlying its anti-HIV-1 activity.


Asunto(s)
Fármacos Anti-VIH , VIH-1 , VIH-1/efectos de los fármacos , Humanos , Fármacos Anti-VIH/farmacología , Fármacos Anti-VIH/química , Ésteres del Forbol/farmacología , Ésteres del Forbol/química , Estructura Molecular , Proteína Quinasa C/metabolismo , Proteína Quinasa C/química , Relación Estructura-Actividad
6.
Chin J Nat Med ; 22(4): 356-364, 2024 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-38658098

RESUMEN

A comprehensive chemical study of the endophytic fungus Arthrinium sp. ZS03, associated with Acorus tatarinowii Schott, yielded eleven pimarane diterpenoids (compounds 1-11), including seven novel compounds designated arthrinoids A-G (1-7). The determination of their structures and absolute configurations was achieved through extensive spectroscopic techniques, quantum chemical calculations of electronic circular dichroism (ECD), and single-crystal X-ray diffraction analysis. Furthermore, 7 demonstrated inhibitory activity against Klebsiella pneumoniae, comparable to the reference antibiotic amikacin, with a minimum inhibitory concentration (MIC) of 8 µg·mL-1.


Asunto(s)
Abietanos , Antibacterianos , Pruebas de Sensibilidad Microbiana , Antibacterianos/farmacología , Antibacterianos/química , Abietanos/farmacología , Abietanos/química , Abietanos/aislamiento & purificación , Estructura Molecular , Ascomicetos/química , Klebsiella pneumoniae/efectos de los fármacos , Diterpenos/farmacología , Diterpenos/química , Cristalografía por Rayos X
7.
Zhongguo Zhong Yao Za Zhi ; 49(6): 1564-1569, 2024 Mar.
Artículo en Chino | MEDLINE | ID: mdl-38621940

RESUMEN

Various separation methods in combination with spectral data analysis, X-ray single crystal diffraction analysis, and litera-ture data comparison were employed to clarify the chemical constituents of Itea yunnanensis. Seven compounds were obtained from I. yunnanensis, which were identified as(S)-3-[1-(4-hydroxyphenyl)propane-2-yl]-4-methoxybenzoate methyl ester(1), iteafuranal B(2), syringaresinol(3), dihydrokaempferol(4), trimethoxybenzene(5), eicosane(6), and nonacosane(7), respectively. Among them, compound 1 was a new nor-neolignan compound named iteanorneoligan A, and the rest of the compounds were identified from I. yunnanensis for the first time. The anti-hepatocellular carcinoma effect of the compound was evaluated based on Sk-hep-1 cells model via MTT assay, and compound 2 showed a significant inhibitory effect on the proliferation of Sk-hep-1 cells with an IC_(50) of 9.4 µmol·L~(-1). The antioxidant capacity was determined via DPPH, ABTS~(·+), and O■ radical scavenging ability, and compound 1 exhibited a significant ABTS~(·+) radical scavenging effect with an IC_(50) of 0.178 mg·mL~(-1).


Asunto(s)
Lignanos , Estructura Molecular , Benzotiazoles , Ácidos Sulfónicos , Antioxidantes/farmacología , Antioxidantes/química
8.
J Am Chem Soc ; 146(18): 12645-12655, 2024 May 08.
Artículo en Inglés | MEDLINE | ID: mdl-38651821

RESUMEN

The increased production of plastics is leading to the accumulation of plastic waste and depletion of limited fossil fuel resources. In this context, we report a strategy to create polymers that can undergo controlled depolymerization by linking renewable feedstocks with siloxane bonds. α,ω-Diesters and α,ω-diols containing siloxane bonds were synthesized from an alkenoic ester derived from castor oil and then polymerized with varied monomers, including related biobased monomers. In addition, cyclic monomers derived from this alkenoic ester and hydrosiloxanes were prepared and cyclized to form a 26-membered macrolactone containing a siloxane unit. Sequential ring-opening polymerization of this macrolactone and lactide afforded an ABA triblock copolymer. This set of polymers containing siloxanes underwent programmed depolymerization into monomers in protic solvents or with hexamethyldisiloxane and an acid catalyst. Monomers afforded by the depolymerization of polyesters containing siloxane linkages were repolymerized to demonstrate circularity in select polymers. Evaluation of the environmental stability of these polymers toward enzymatic degradation showed that they undergo enzymatic hydrolysis by a fungal cutinase from Fusarium solani. Evaluation of soil microbial metabolism of monomers selectively labeled with 13C revealed differential metabolism of the main chain and side chain organic groups by soil microbes.


Asunto(s)
Fusarium , Polimerizacion , Siloxanos , Siloxanos/química , Aceites de Plantas/química , Polímeros/química , Estructura Molecular , Hidrolasas de Éster Carboxílico
9.
J Mater Chem B ; 12(17): 4197-4207, 2024 May 01.
Artículo en Inglés | MEDLINE | ID: mdl-38595311

RESUMEN

Second near-infrared (NIR-II) fluorescence imaging shows huge application prospects in clinical disease diagnosis and surgical navigation, while it is still a big challenge to exploit high performance NIR-II dyes with long-wavelength absorption and high fluorescence quantum yield. Herein, based on planar π-conjugated donor-acceptor-donor systems, three NIR-II dyes (TP-DBBT, TP-TQ1, and TP-TQ2) were synthesized with bulk steric hindrance, and the influence of acceptor engineering on absorption/emission wavelengths, fluorescence efficiency and photothermal properties was systematically investigated. Compared with TP-DBBT and TP-TQ2, the TP-TQ1 based on 6,7-diphenyl-[1,2,5]thiadiazoloquinoxaline can well balance absorption/emission wavelengths, NIR-II fluorescence brightness and photothermal effects. And the TP-TQ1 nanoparticles (NPs) possess high absorption ability at a peak absorption of 877 nm, with a high relative quantum yield of 0.69% for large steric hindrance hampering the close π-π stacking interactions. Furthermore, the TP-TQ1 NPs show a desirable photothermal conversion efficiency of 48% and good compatibility. In vivo experiments demonstrate that the TP-TQ1 NPs can serve as a versatile theranostic agent for NIR-II fluorescence/photoacoustic imaging-guided tumor phototherapy. The molecular planarization strategy provides an approach for designing efficient NIR-II fluorophores with extending absorption/emission wavelength, high fluorescence brightness, and outstanding phototheranostic performance.


Asunto(s)
Colorantes Fluorescentes , Rayos Infrarrojos , Quinoxalinas , Tiadiazoles , Quinoxalinas/química , Quinoxalinas/síntesis química , Quinoxalinas/farmacología , Colorantes Fluorescentes/química , Colorantes Fluorescentes/síntesis química , Animales , Ratones , Humanos , Tiadiazoles/química , Nanomedicina Teranóstica , Estructura Molecular , Antineoplásicos/química , Antineoplásicos/farmacología , Antineoplásicos/síntesis química , Imagen Óptica , Ratones Endogámicos BALB C , Femenino , Fototerapia/métodos , Supervivencia Celular/efectos de los fármacos , Nanopartículas/química , Tamaño de la Partícula
10.
Chem Biodivers ; 21(5): e202400265, 2024 May.
Artículo en Inglés | MEDLINE | ID: mdl-38470349

RESUMEN

The phytochemical investigation of the leaves of Inula confertiflora, a medicinal plant endemic to Ethiopia, led to the isolation of 15 terpenoids; 1ß-hydroxy-α-costic acid (1), 3α-hydroxycostic acid (2), isotelekin (3), asperilin (4), carabrone (5), carpesioline (6), graveolide (7), inuviscolide (8), 8-epi-inuviscolide (9), 1ß,4ß-dihydroxy-5α(H)-guaia-10(14),11(13)-dien-8α,12-olide (10), isoinuviscolide (11), 4ß,10ß-dihydroxy-5α(H)-1,11(13)-guaidien-8α,12-olide (12), 4ß,10ß-dihydroxy-1ß(H)-5α(H)-guai-11(13)-en-8α,12-olide (13), 4ß,10α-dihydroxy-1ß(H)-5α(H)-guai-11(13)-en-8α,12-olide (14), 4ß,10α-dihydroxy-1α(H)-5α(H)-guai-11(13)-en-8α,12-olide (15). Herein, structural elucidation and full NMR data for compound 1 are presented for the first time. The structures were elucidated using NMR, HRESIMS, and by comparison with literature data. The relative configurations were defined by NOESY correlations and single-crystal X-ray crystallography. Herein, crystallography data of 6 and 7 were reported for the first time. The antibacterial efficacy of some of the isolated compounds was evaluated against two commonly dispersed environmental strains of Escherichia coli and Staphylococcus aureus. Compounds 1, 3, 6, 7, and 8 exhibited moderate antibacterial activities against the tested organisms. The chemotaxonomic significance of compounds is discussed.


Asunto(s)
Antibacterianos , Inula , Lactonas , Pruebas de Sensibilidad Microbiana , Sesquiterpenos , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Lactonas/química , Lactonas/farmacología , Lactonas/aislamiento & purificación , Inula/química , Sesquiterpenos/química , Sesquiterpenos/farmacología , Sesquiterpenos/aislamiento & purificación , Hojas de la Planta/química , Staphylococcus aureus/efectos de los fármacos , Relación Estructura-Actividad , Estructura Molecular , Conformación Molecular
11.
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
12.
Angew Chem Int Ed Engl ; 63(19): e202402050, 2024 May 06.
Artículo en Inglés | MEDLINE | ID: mdl-38488804

RESUMEN

Germacranolides, secondary metabolites produced by plants, have garnered academic and industrial interest due to their diverse and complex topology as well as a wide array of pharmacological activities. Molephantin, a highly oxygenated germacranolide isolated from medicinal plants, Elephantopus mollis and Elephantopus tomentosus, has exhibited antitumor, inflammatory, and leishmanicidal activities. Its chemical structure is based on a highly strained ten-membered macrocyclic backbone with an (E,Z)-dienone moiety, which is fused with an α-methylene-γ-butyrolactone and adorned with four successive stereogenic centers. Herein, we report the first synthesis of molephantin in 12 steps starting from readily available building blocks. The synthesis features the highly diastereoselective intermolecular Barbier allylation of the ß,γ-unsaturated aldehyde with optically active 3-bromomethyl-5H-furan-2-one intermediate and ensuing Nozaki-Hiyama-Kishi (NHK) macrocyclization for the construction of the highly oxygenated ten-membered macrocyclic framework. This synthetic route enabled access to another germacranolide congener, tomenphantopin F. Furthermore, cycloisomerization of molephantin into 2-deethoxy-2ß-hydroxyphantomolin could be facilitated by irradiation with ultraviolet A light (λmax=370 nm), which opened a versatile and concise access to the related furanogermacranolides such as EM-2, phantomolin, 2-O-demethyltomenphantopin C, and tomenphantopin C.


Asunto(s)
Oxígeno , Oxígeno/química , Asteraceae/química , Estereoisomerismo , Sesquiterpenos de Germacrano/química , Sesquiterpenos de Germacrano/síntesis química , Furanos/química , Furanos/síntesis química , Estructura Molecular
13.
Angew Chem Int Ed Engl ; 63(19): e202403271, 2024 May 06.
Artículo en Inglés | MEDLINE | ID: mdl-38497510

RESUMEN

Unnatural amino acids, and their synthesis by the late-stage functionalization (LSF) of peptides, play a crucial role in areas such as drug design and discovery. Historically, the LSF of biomolecules has predominantly utilized traditional synthetic methodologies that exploit nucleophilic residues, such as cysteine, lysine or tyrosine. Herein, we present a photocatalytic hydroarylation process targeting the electrophilic residue dehydroalanine (Dha). This residue possesses an α,ß-unsaturated moiety and can be combined with various arylthianthrenium salts, both in batch and flow reactors. Notably, the flow setup proved instrumental for efficient scale-up, paving the way for the synthesis of unnatural amino acids and peptides in substantial quantities. Our photocatalytic approach, being inherently mild, permits the diversification of peptides even when they contain sensitive functional groups. The readily available arylthianthrenium salts facilitate the seamless integration of Dha-containing peptides with a wide range of arenes, drug blueprints, and natural products, culminating in the creation of unconventional phenylalanine derivatives. The synergistic effect of the high functional group tolerance and the modular characteristic of the aryl electrophile enables efficient peptide conjugation and ligation in both batch and flow conditions.


Asunto(s)
Alanina , Alanina/análogos & derivados , Péptidos , Péptidos/química , Péptidos/síntesis química , Catálisis , Alanina/química , Procesos Fotoquímicos , Estructura Molecular
14.
15.
Fitoterapia ; 174: 105871, 2024 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-38428618

RESUMEN

The essential oils of Thymus vulgaris (TVEO) and Thymus serpyllum (TSEO) show different biological activities. The aim of the study was to evaluate the biological activities of TVEO and TSEO from Montenegro. The main components of TVEO were p-cymene (29.52%), thymol (22.8%) and linalool (4.73%) while the main components of TSEO were p-cymene (19.04%), geraniol (11,09%), linalool (9.16%), geranyl acetate (6.49%) and borneol (5.24%). Antioxidant activity determined via DPPH for TVEO was 4.49 and FRAP 1130.27, while for TSEO it was estimated that DPPH was 4.88 µL/mL and FRAP was 701.25 µmol FRAP/L. Both essential oils were active against all tested bacteria, with the highest level of sensitivity of E. coli with MIC of 1.5625 µL/mL. Essential oils showed strong cytotoxic effects on human cancer cell lines, with IC50 values ranging from 0.20 to 0.24 µL/mL for TVEO and from 0.32 to 0.49 µL/mL for TSEO. TVEO caused apoptosis in cervical adenocarcinoma HeLa cells through activation of caspase-3 and caspase-8, while TSEO caused apoptosis through caspase-3. EOs decreased levels of oxidative stress in normal MRC-5 cells. HeLa cells treated with TVEO had reduced MMP2 expression levels, while cells treated with TSEO had lowered MMP2 and MMP9 levels. The treatment of HeLa cells with TVEO increased the levels of miR-16 and miR-34a, indicating potential tumor-suppressive properties. Our findings suggest that Thymus essential oils may be considered as good candidates for further investigation as cancer-chemopreventive and cancer-therapeutic agents.


Asunto(s)
Monoterpenos Acíclicos , Cimenos , MicroARNs , Aceites Volátiles , Thymus (Planta) , Humanos , Aceites Volátiles/química , Antioxidantes/farmacología , Antioxidantes/química , Caspasa 3 , Metaloproteinasa 2 de la Matriz/farmacología , Escherichia coli , Thymus (Planta)/química , Células HeLa , Montenegro , Estructura Molecular , Antibacterianos/farmacología , Antibacterianos/química , Aceites de Plantas/farmacología , Aceites de Plantas/química
16.
Fitoterapia ; 174: 105876, 2024 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-38431027

RESUMEN

Nine polyacetylenes, including five new compounds named sadivaethynes E-I (1-5), were isolated from the roots of Saposhnikovia divaricata. Structural elucidation of compounds 1-5 was established by extensive spectroscopic analysis, quantum chemical calculations and DP4+ probability analysis. Among them, the absolute configuration of compound 1-2, 4-5 was unambiguous determined by ECD. Also, all compounds were evaluated for cytotoxicity against two human cancer cell lines (A549, HEPG2) in vitro, compound 9 showed moderate inhibitory effect with an IC50 value of 11.66 µM against HEPG2.


Asunto(s)
Apiaceae , Poliinos , Humanos , Estructura Molecular , Poliinos/farmacología , Poliinos/análisis , Poliinos/química , Raíces de Plantas/química , Extractos Vegetales/química , Apiaceae/química
17.
Fitoterapia ; 174: 105880, 2024 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-38431026

RESUMEN

An undescribed trichodenone derivative (1), two new diketopiperazines (3 and 4) along with a bisabolane analog (2) were isolated from Trichoderma hamatum b-3. The structures of the new findings were established through comprehensive analyses of spectral evidences in HRESIMS, 1D and 2D NMR, Marfey's analysis as well as comparisons of ECD. The absolute configuration of 2 was unambiguously confirmed by NMR, ECD calculation and Mo2(AcO)4 induced circular dichroism. Compounds 1-4 were tested for their fungicidal effects against eight crop pathogenic fungi, among which 1 showed 51% inhibition against Sclerotinia sclerotiorum at a concentration of 50 µg/mL.


Asunto(s)
Hypocreales , Trichoderma , Estructura Molecular , Dicetopiperazinas/química , Trichoderma/química
18.
J Nat Prod ; 87(4): 1246-1267, 2024 Apr 26.
Artículo en Inglés | MEDLINE | ID: mdl-38449105

RESUMEN

Ginsenosides, the primary pharmacologically active constituents of the Panax genus, have demonstrated a variety of medicinal properties, including anticardiovascular disease, cytotoxic, antiaging, and antidiabetes effects. However, the low concentration of ginsenosides in plants and the challenges associated with their extraction impede the advancement and application of ginsenosides. Heterologous biosynthesis represents a promising strategy for the targeted production of these natural active compounds. As representative triterpenoids, the biosynthetic pathway of the aglycone skeletons of ginsenosides has been successfully decoded. While the sugar moiety is vital for the structural diversity and pharmacological activity of ginsenosides, the mining of uridine diphosphate-dependent glycosyltransferases (UGTs) involved in ginsenoside biosynthesis has attracted a lot of attention and made great progress in recent years. In this paper, we summarize the identification and functional study of UGTs responsible for ginsenoside synthesis in both plants, such as Panax ginseng and Gynostemma pentaphyllum, and microorganisms including Bacillus subtilis and Saccharomyces cerevisiae. The UGT-related microbial cell factories for large-scale ginsenoside production are also mentioned. Additionally, we delve into strategies for UGT mining, particularly potential rapid screening or identification methods, providing insights and prospects. This review provides insights into the study of other unknown glycosyltransferases as candidate genetic elements for the heterologous biosynthesis of rare ginsenosides.


Asunto(s)
Ginsenósidos , Glicosiltransferasas , Ginsenósidos/biosíntesis , Ginsenósidos/química , Ginsenósidos/metabolismo , Glicosiltransferasas/metabolismo , Saccharomyces cerevisiae , Estructura Molecular , Panax/química , Uridina Difosfato/metabolismo , Bacillus subtilis/enzimología , Vías Biosintéticas
20.
Chin J Nat Med ; 22(3): 265-272, 2024 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-38553193

RESUMEN

Four new sesquiterpene lactones (SLs) (1-4), along with a biosynthetically related SL (5), have been isolated from the leaves of Magnolia grandiflora. Magrandate A (1) is notable as the first C18 homogemarane type SL, featuring a unique 1,7-dioxaspiro[4.4]nonan-6-one core. Compounds 2 and 3, representing the first instances of chlorine-substituted gemarane-type SL analogs in natural products, were also identified. The structures of these isolates were elucidated through a combination of spectroscopic data analysis, electronic circular dichroism calculations, and X-ray single-crystal diffraction analysis. All isolates demonstrated anti-inflammatory activity in lipopolysaccharide-stimulated RAW264.7 cells. Notably, 3-5 showed a significant inhibitory effect on nitric oxide production, with IC50 values ranging from 0.79 to 4.73 µmol·L-1. Additionally, 4 and 5 exhibited moderate cytotoxic activities against three cancer cell lines, with IC50 values between 3.09 and 11.23 µmol·L-1.


Asunto(s)
Magnolia , Sesquiterpenos , Estructura Molecular , Magnolia/química , Antiinflamatorios/farmacología , Sesquiterpenos/farmacología , Sesquiterpenos/química , Lactonas/farmacología , Lactonas/química
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