Background:Terpinen-4-ol(T4O),a key constituent of tea tree essential oil and various aromatic plants,has shown promising antiproliferative and pro-apoptotic effects in melanoma and other cancer types.However,its effi...Background:Terpinen-4-ol(T4O),a key constituent of tea tree essential oil and various aromatic plants,has shown promising antiproliferative and pro-apoptotic effects in melanoma and other cancer types.However,its efficacy against cutaneous squamous cell carcinoma(cSCC)remains unclear.Thus,in this study,we investigated the in vivo and in vitro effects of T4O on cSCC cell lines and preliminarily explored its impacting pathways.Methods:Using CCK8 and assay colony formation,we assessed the viability of cSCC A431,SCL-1,and COLO-16 cells treated with T40 at varying concentrations(0,1,2,and 4μM).Flow cytometry was employed to evaluate T4O’s effect on cSCC cell’s cycle progression and apoptosis induction.Additionally,western blotting was utilized to examine the expression intensities of N-cadherin and E-cadherin,two indicative markers of the epithelial-mesenchymal transition(EMT)pathway.T4O’s in vivo effect on inhibiting tumor progression was evaluated on an established xenograft tumor model.Then,the molecular mechanisms of T4O’s antitumor effect were explored by an integrated genome-wide transcriptomics and proteomics study on cSCC A431c cells.Finally,calpain-2’s potential mediator role in T4O’s anti-tumor mechanism was investigated in calpain-2 knockdown cell lines prepared via siRNA transfection.Result:It’s demonstrated that T4O treatment inhibited cSCC proliferation,clonogenicity,migration,and invasion while inducing apoptosis and suppressing the EMT pathway.T4O administration also inhibited cSCC tumorigenesis in the xenograft tumor model.RNA-sequencing and iTRAQ analysis detected significant upregulation of calpain-2 expression in T4O-treated cSCC cells.Western blotting confirmed that T4O significantly increased calpain-2 expression and promoted proteolytic cleavage ofβ-catenin and caspase-12,two calpain-2 target proteins.Importantly,siRNA-mediated calpain-2 knockdown relieved T4O’s suppressive effect on cSCC cell proliferation and motility.Mechanistically,T4O upregulates calpain-2 expression and promotes the cleavage ofβ-catenin and caspase-12,with siRNA-mediated calpain-2 knockdown mitigating T4O’s suppressive effects.Conclusion:These findings suggest that T4O’s antitumor activity in cSCC is mediated through the upregulation of calpain-2 expression and subsequent modulation ofβ-catenin and caspase-12.展开更多
Five new flavan-4-ol glycosides jixueqiosides A-E(1-5)and two new flavan glycosides jixueqiosides F and G(6 and 7),along with twelve known flavan-4-ol glycosides(8-19),were isolated from the roots of Pronephrium penan...Five new flavan-4-ol glycosides jixueqiosides A-E(1-5)and two new flavan glycosides jixueqiosides F and G(6 and 7),along with twelve known flavan-4-ol glycosides(8-19),were isolated from the roots of Pronephrium penangianum.Comprehensive spectral analyses,X-ray single-crystal diffraction,and theoretical electronic circular dichroism(ECD)calculations established structures and absolute configurations.A single crystal structure of flavan-4-ol glycoside(14)was reported for the first time,while the characteristic ECD and NMR data for all isolated flavan-4-ol glycosides(1-5,8-19)were analyzed,establishing a set of empirical rules.Activity screening of these isolates showed that 8 and 9 could inhibit the proliferation of MDA-MB-231 and MCF-7 cells with IC50 values of 7.93±2.85μmol·L^(-1)and 5.87±1.58μmol·L^(-1)(MDA-MB-231),and 2.21±1.38μmol·L^(-1)and 3.52±1.55μmol·L^(-1)(MCF-7),respectively.Western blotting and flow cytometry analyses demonstrated that 8 and 9 dose-dependently induced apoptosis in MDA-MB-231 cells by up-regulating BAX,activating caspase-3 and down-regulating BCL-2.Additionally,compound 8 affected autophagy-related proteins,increasing the ratio of LC3-II/LC3-I and Beclin-1 levels to inhibit MDA-MB-231 cell proliferation.Moreover,anti-inflammatory studies indicated that 2,3,7,13,14,and 18 moderately inhibited tumor necrosis factor-α(TNF-α),interleukin-6(IL-6),and nitric oxide(NO)release.展开更多
To study insecticidal mechanism of terpinen-4-ol, a main insecticidal composition in the essential oil of Sabina vulgaris, the 5th instar larvae of Mythimna separta, were investigated with terpinen-4-ol by topical app...To study insecticidal mechanism of terpinen-4-ol, a main insecticidal composition in the essential oil of Sabina vulgaris, the 5th instar larvae of Mythimna separta, were investigated with terpinen-4-ol by topical application. The activities of phosphatase, glutathione S-transferase （GSTs）, cytochrome P450 （P450）, and polyphenol oxidase （PPO） of tested insects were determined in all poisoning stages, including exciting stage, convulsing stage, paralysis stage, and recover stage. The result showed that the activities of both acid phosphatase （ACP） and alkaline phosphatase （AKP） in treated insects were induced by terpinen-4-ol, but ACP was inhibited in paralysis stage. The activities of GSTs were inhibited in exciting stage, convulsing stage, and paralysis stage, but gradually recovered in recover stage. O-demethylase activity of cytochrome P450 was inhibited by terpinen-4-ol, and the inhibition rate in all poisoning stages were 26.27, 46.03, 80.24, and 90.22%, respectively. PPO activities were strongly inhibited by terpinen-4-ol both in vitro and in vivo. In conclusion, the activities of P450, GSTs, and PPO could have relation with toxicity of terpinen-4-ol against larvae of the Mythimna separta, but recover stage of the poisoning insects might be related to GSTs induced. As a new insecticide or synergist, terpinen- 4-ol has a potential value in field of insecticide resistance management.展开更多
This study aims to elucidate intestinal injury from the perspective of intestinal epithelial cell homeostasis and to explore the modulatory roles of terpine-4-ol(a major bioactive component of tea tree oil).Forty 28-d...This study aims to elucidate intestinal injury from the perspective of intestinal epithelial cell homeostasis and to explore the modulatory roles of terpine-4-ol(a major bioactive component of tea tree oil).Forty 28-day-old piglets(7.82±0.43 kg)were randomly divided into 5 groups with 8 pigs per group.Piglets in the control(CON)and lipopolysaccharide(LPS)groups were fed a basal diet,while those in the remaining 3 groups were fed the basal diet supplemented with 30(LTP),60(MTP),or 90 mg/kg terpine4-ol(HTP),respectively.Piglets in the LPS and terpine-4-ol supplementation groups were intraperitoneally injected with 100μg/kg BW of LPS at the end of the 21-day growth period.Six hours after injection,6 piglets from each group were randomly selected and slaughtered to detect intestinal cell homeostasis.The results showed that the average daily weight gain(ADG)and average daily feed intake(ADFI)of piglets in MTP and HTP groups were higher than those in the CON group(P<0.05),whereas the feed conversion ratio(FCR)of piglets in LTP group was lower as compared to the CON group(P=0.007).Terpine-4-ol supplementation also decreased the diarrhea rate of piglets.Lipopolysaccharide challenge decreased the villus length and the ratio of villus length to crypt depth(V/C)in the jejunum(P<0.05),decreased the V/C ratio and increased the crypt depth in the ileum(P<0.05).In contrast,terpine-4-ol supplementation led to increased villus length and V/C ratio in the jejunum,raised the V/C ratio in the HTP group,and decreased crypt depth in the LTP and MTP groups in the ileum(P<0.05).Lipopolysaccharide reduced the number of antigen Ki-67 positive(Ki67^(+))cells and increased the number of caspase 3^(+)cells(P<0.05)in both the jejunum and ileum,whereas terpine-4-ol increased the number of Ki67^(+)cells in the crypts of the jejunum and ileum,while decreasing the number of caspase 3^(+)cells of the ileum and in the jejunum of MTP and HTP groups(P<0.05).Lipopolysaccharide downregulated the expression of the intestinal stem cell marker leucine-rich repeat-containing G-protein coupled receptor 5(Lgr5)(P<0.05,except for Lgr5 gene in the jejunum),while terpine-4-ol supplementation alleviated the effect.Lipopolysaccharide decreased the number of goblet cells and mucin 2(Muc2)secretion(P<0.05),whereas the number of goblet cells and Muc2 secretion in the small intestine of MTP group were increased(P<0.05).In addition,LPS injection led to a reduction in the expression of endocrine cell marker chromogranin A and absorption cell marker villin(P<0.05).Conversely,terpine-4-ol increased the abundance of endocrine cells and absorption cells in the small intestine(P<0.05).Moreover,LPS inhibited the expression of genes and proteins of wingless-type MMTV integration site family(Wnt)/β-catenin signaling pathway(P<0.05),whereas terpine-4-ol reversed this effect.In conclusion,terpine-4-ol supplementation improved growth performance,decreased diarrhea in piglets and alleviated the damage to the intestinal epithelial cell homeostasis under LPS challenge,probably via Wnt/β-catenin signaling activation.A dose of 60 mg terpine-4-ol per kilogram diet was recommended based on the present study.展开更多
To reveal the insecticidal mechanism of terpinen-4-ol, the activity of Na＋,K＋-ATPase in insects tested were determined in vivo and in vitro. The results showed that terpinen-4-ol and its ester derivatives had strong...To reveal the insecticidal mechanism of terpinen-4-ol, the activity of Na＋,K＋-ATPase in insects tested were determined in vivo and in vitro. The results showed that terpinen-4-ol and its ester derivatives had strong contact activity to housefly and the contact toxicities of its derivatives except Z3 were all superior or equivalent to terpinen-4-ol. All the 7 compounds had strong inhibition towards activity of Na＋,K＋-ATPase. With poisoning symptom exacerbating, the inhibition rates were gradually increased. In vitro, the IC50 of terpinen-4-ol, Z1, Z2, Z4, Z5, and Z6 was 155.89, 197.98, 96.02, 121.36, 124.85, and 153.74 μg mL% respectively. There was well correlation between the LDs0 of terpinen-4-ol derivatives to housefly and the IC50 of terpinen-4-ol derivatives to Na＋,K＋-ATPase in housefly. In conclusion, Na＋,K＋-ATPase was likely the target of terpinen-4-ol against insects.展开更多
A more feasibly convergent synthesis of selective estrogen receptor degrading agent(S)-8-(4-((1-(3-fluoropropyl)-pyrrolidin-3-yl)oxy)phenyl)-7-(4-hydroxyphenyl)-5,6-dihydronaphthalen-2-ol was reported,featured with co...A more feasibly convergent synthesis of selective estrogen receptor degrading agent(S)-8-(4-((1-(3-fluoropropyl)-pyrrolidin-3-yl)oxy)phenyl)-7-(4-hydroxyphenyl)-5,6-dihydronaphthalen-2-ol was reported,featured with concise work up and absence of regioselectivity dilemma.展开更多
Zingiber cassumunar is an important plant used in traditional medicine and as a natural mosquito re-pellent.However,the compounds responsible for the repellent activity of the plant are still unknown.The aim of the st...Zingiber cassumunar is an important plant used in traditional medicine and as a natural mosquito re-pellent.However,the compounds responsible for the repellent activity of the plant are still unknown.The aim of the study is to identify the components of Z.cassumunar essential oil that show repellent activity against Aedes albopictus.We also evaluated the larvicidal and adulticidal activities of Z.cassumunar essential oil against Ae.albopictus.In-cage mosquito repellent experiments showed that Z.cassumunar essential oil possessed moderate repellent activity with a minimum effective dose(MED)of 0.16±0.01 mg/cm^(20,compared to reference standard N,N-diethyl-3-methylbenzamide(DEET,0.03±0.01 mg/cm^(20).Bioassay-guided fractionation identified the major active compound of Z.cassumunar essential oil as(-)-terpinen-4-ol(1)(MED:0.19±0 mg/cm^(20).We also found that Z.cassumunar essential oil showed moderate larvicidal activity against first instar larvae of Ae.albopictus with a LC50(50%lethal concentration)of 44.9 mg/L after 24 h.Fumigation bioassays showed that Z.cassumunar essential oil exhibits moderate adulticidal activity against Ae.albopictus with a LC50 of 5.44%,while(-)-terpinen-4-ol showed significant adulticidal activity with a LC50 of 2.10%after 24 h.This study verifies that the Z.cassumunar essential oil has mosquito repellent activity,and that(-)-terpinen-4-ol is mainly responsible for this activity.Furthermore,this study provides scientific support for the folk usage of Z.cassumunar essential oil as mosquito repellent and indicates that Z.cassumunar essential oil and(-)-terpinen-4-ol can be used as plant-derived repellents and insecticides for mosquito control.展开更多
2-[3,5-Di-O-β-D-glucosyl-4-(3-methylbut-2-enyl)phenyl]benzofuran-6-ol,a new prenylated arylbenzofuran derivative was isolated from Morus alba L.Its structure was elucidated by various spectroscopic methods including ...2-[3,5-Di-O-β-D-glucosyl-4-(3-methylbut-2-enyl)phenyl]benzofuran-6-ol,a new prenylated arylbenzofuran derivative was isolated from Morus alba L.Its structure was elucidated by various spectroscopic methods including MS,~1H NMR,^(13)C NMR,DEPT,~1H-~1HCOSY,HMQC and HMBC.展开更多
We compared two different strategies to increase the catches oflps typographus （L.）, particularly males, in pheromone-baited traps. The first of these strategies, the barrier approach, used alternating pheromone ble...We compared two different strategies to increase the catches oflps typographus （L.）, particularly males, in pheromone-baited traps. The first of these strategies, the barrier approach, used alternating pheromone blends, targeting males and females respectively, in closely-spaced traps forming a barrier around forest stands. The second strategy, the single trap approach, used widely-spaced traps that were all baited with the same lure and intended to trap the highest possible numbers of males without compromising trapping of females. In the blend used for the barrier traps targeting primarily males, with a lower percentage of （4S）-cis-verbenol （cV）, the （-）-α-pinene was replaced step wise with （＋）-limonene at rates of 0%, 1%, 10%, 35%, 60% and 90%. This replacement had no significant effect on the numbers of responding 1. typographus males, but there was a slight effect on the percentage of males caught. In the attractant blend for the barrier traps targeting females, with a higher percentage of cV, the 2-methyl-3-buten-2-ol （MB） was replaced with 1-methoxy-2-propanol （MP） in a similar fashion as for the male-specific blends. The replacement did not significantly affect the catch of females. Thus, it is pos- sible to use the MP in the blend with cV and ipsdienol without significant change in catch efficacy. In the blends for single traps, the （-）-α- pinene was replaced with （＋）-limonene and MB with MP. The replacement of （-）-α-pinene had only a slight effect on the percentage of males, but the results suggest that replacing MB with MP in the blend will not significantly reduce trapping efficacy.展开更多
Over the past few decades,complementary and alternative treatments have become increasingly popular worldwide.The purported therapeutic characteristics of natural products have come under increased scrutiny both in vi...Over the past few decades,complementary and alternative treatments have become increasingly popular worldwide.The purported therapeutic characteristics of natural products have come under increased scrutiny both in vitro and in vivo as part of efforts to legitimize their usage.One such product is tea tree oil(TTO),a volatile essential oil primarily obtained from the native Australian plant,Melaleuca alternifolia,which has diverse traditional and industrial applications such as topical preparations for the treatment of skin infections.Its anti-inflammatory-linked immunomodulatory actions have also been reported.This systematic review focuses on the anti-inflammatory effects of TTO and its main components that have shown strong immunomodulatory potential.An extensive literature search was performed electronically for data curation on worldwide accepted scientific databases,such as Web of Science,Google Scholar,PubMed,ScienceDirect,Scopus,and esteemed publishers such as Elsevier,Springer,Frontiers,and Taylor&Francis.Considering that the majority of pharmacological studies were conducted on crude oils only,the extracted data were critically analyzed to gain further insight into the prospects of TTO being used as a neuroprotective agent by drug formulation or dietary supplement.In addition,the active constituents contributing to the activity of TTO have not been well justified,and the core mechanisms need to be unveiled especially for anti-inflammatory and immunomodulatory effects leading to neuroprotection.Therefore,this review attempts to correlate the anti-inflammatory and immunomodulatory activity of TTO with its neuroprotective mechanisms.展开更多
A highly efficient synthesis of novel pyrido[2,3-d]pyrimidin-4-ols was developed via an iodine-catalyzed tandem oxidative cyclization under focused microwave irradiation. Pyrido[2,3-d]pyrimidin-4-ols were obtained fro...A highly efficient synthesis of novel pyrido[2,3-d]pyrimidin-4-ols was developed via an iodine-catalyzed tandem oxidative cyclization under focused microwave irradiation. Pyrido[2,3-d]pyrimidin-4-ols were obtained from easily available 2-amino-4-aryl-6-arylnicotinamides and benzylic amines with good to excellent yields.展开更多
Essential oil from the leaves of Pistacia lentiscus L. growing in the Oran region in the west of Algeria was obtained by hydrodistillation with a 1.26 % yield on a dry weight basis. Spectrophotometric analyses were em...Essential oil from the leaves of Pistacia lentiscus L. growing in the Oran region in the west of Algeria was obtained by hydrodistillation with a 1.26 % yield on a dry weight basis. Spectrophotometric analyses were employed to highlight the scavenger capacity of this oil using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) test. Twenty compounds were identified by GC and CG/MS analyses, and the main part of the compounds of the oil was terpinene-4-ol (41.24%) and α-terpineol (7.31%), α-pinene (9.48%), limonene (09.11%), β-myrcene (10.5%), p-cymene (8.67%) and α-phellandrene (2.20%), β-caryophyllene (12.62%) as major compounds. The DPPH test shows that Pistacia lentiscus essential oil possesses antiradical activity. A linear correlation (correlation coefficient R<sup>2</sup> = 0.995, P Pistacia lentiscus essential oil.展开更多
This study aims to explore the analgesic ingredients and mechanism of Cinnamomum camphora essential oil(CCEO).The constituents in CCEO were characterized qualitatively by gas chromatography-mass spectrometry.Targets r...This study aims to explore the analgesic ingredients and mechanism of Cinnamomum camphora essential oil(CCEO).The constituents in CCEO were characterized qualitatively by gas chromatography-mass spectrometry.Targets related to active ingredients were collected by PubChem and Swiss Target Prediction.Targets related to pain were screened by TTD and OMIM database,and compound-target network was established by Cytoscape software.Gene ontology(GO)function and Kyoto encyclopedia of genes and genomes(KEGG)pathway enrichment analysis of targets were carried out by DAVID database.Protein-protein interaction(PPI)network was established and analyzed by STRING database.Molecular docking method was used to verify the interaction between main components and relevant core targets.A total of 13 compounds were identified in CCEO,and 58 related targets were predicted.GO function enrichment analysis revealed that the selected targets were mainly involved in biological processes such as chemical synaptic transmission and molecular function such as neurotransmitter receptor activity;24 signal pathways were screened by KEGG pathway enrichment analysis,including neuroactive ligand-receptor interaction,retrograde endocannabinoid signaling and calcium signaling pathway.Docking results showed that the main constituents had certain affinities with the key targets.The active ingredients in CCEO regulated multiple signaling pathways to ameliorate pain through AR,ACHE,ESR1,GABRG2,PTGS2 and PPARγ.展开更多
Electrocatalytic conversion presents a promising alternative to conventional industrial catalysis.While aqueous-phase electrocatalysis has achieved notable advancements,oil-water immiscible systems remain challenging ...Electrocatalytic conversion presents a promising alternative to conventional industrial catalysis.While aqueous-phase electrocatalysis has achieved notable advancements,oil-water immiscible systems remain challenging due to restricted reaction flux at multiphase interfaces.To address the limitation,we engineered a biphasic reaction system featuring a tailored oil-water catalytic interface in cyclohexene oxidation reaction(COR).The system employed a catalyst-loaded porous electrode as an active phase domain,enabling spatial separation of cyclohexene(organic phase)and electrolyte(aqueous phase).The tailored oil-water interface enhanced the interfacial mass transfer of substrate-catalysts and facilitated the spontaneous migration of 2-cyclohexen-1-ol into the aqueous phase,thereby streamlining product separation.Notably,polyaniline(PANI)modification on Co_(3)O_(4)enhanced surface lipophilicity,promoting cyclohexene adsorption and accelerating the COR catalytic kinetics(Co^(3+)-O+cyclohexene-H+e-→Co^(2+)-OH+2-cyclohexen-1-ol).The synergistic effects of optimized interfacial engineering and catalyst functionalization achieved exceptional performance:a current density of 45 mA·cm^(-2)at 1.6 V vs.reversible hydrogen electrode(V_(RHE)),coupled with 96.2%selectivity and 82.9%Faradaic efficiency.This work establishes an innovative paradigm for electrocatalytic conversions in oil-water immiscible systems through rational interface design and catalyst surface modulation.展开更多
Objective To study the chemical constituents of Pronephrium triphyllum.Methods The chemical constituents in the plant were isolated and purified with silica gel and Sephadex LH-20.Their structures were identified by a...Objective To study the chemical constituents of Pronephrium triphyllum.Methods The chemical constituents in the plant were isolated and purified with silica gel and Sephadex LH-20.Their structures were identified by analyses of spectral data and physicochemical properties.Results Six compounds were isolated and identified as shelincaoide A(1),n-butyl-β-D-fructopyranoside(2),triphyllin A(3),6,7-di-hydroxycoumarin(4),daucosterol(5),andβ-sitosterol(6),respectively.Conclusion Compound 1 is found to be a new compound.Compounds 2 and 4 are firstly isolated from the plants in Pronephrium Presl.and all compounds except 3 are obtained from the species for the first time.展开更多
基金supported by the Basic Research Program of the Guizhou Science Cooperation Foundation Project(Grant Number:ZK[2021]466)Guizhou Provincial Health Commission(Grant Number:gzwkj2022-062).
文摘Background:Terpinen-4-ol(T4O),a key constituent of tea tree essential oil and various aromatic plants,has shown promising antiproliferative and pro-apoptotic effects in melanoma and other cancer types.However,its efficacy against cutaneous squamous cell carcinoma(cSCC)remains unclear.Thus,in this study,we investigated the in vivo and in vitro effects of T4O on cSCC cell lines and preliminarily explored its impacting pathways.Methods:Using CCK8 and assay colony formation,we assessed the viability of cSCC A431,SCL-1,and COLO-16 cells treated with T40 at varying concentrations(0,1,2,and 4μM).Flow cytometry was employed to evaluate T4O’s effect on cSCC cell’s cycle progression and apoptosis induction.Additionally,western blotting was utilized to examine the expression intensities of N-cadherin and E-cadherin,two indicative markers of the epithelial-mesenchymal transition(EMT)pathway.T4O’s in vivo effect on inhibiting tumor progression was evaluated on an established xenograft tumor model.Then,the molecular mechanisms of T4O’s antitumor effect were explored by an integrated genome-wide transcriptomics and proteomics study on cSCC A431c cells.Finally,calpain-2’s potential mediator role in T4O’s anti-tumor mechanism was investigated in calpain-2 knockdown cell lines prepared via siRNA transfection.Result:It’s demonstrated that T4O treatment inhibited cSCC proliferation,clonogenicity,migration,and invasion while inducing apoptosis and suppressing the EMT pathway.T4O administration also inhibited cSCC tumorigenesis in the xenograft tumor model.RNA-sequencing and iTRAQ analysis detected significant upregulation of calpain-2 expression in T4O-treated cSCC cells.Western blotting confirmed that T4O significantly increased calpain-2 expression and promoted proteolytic cleavage ofβ-catenin and caspase-12,two calpain-2 target proteins.Importantly,siRNA-mediated calpain-2 knockdown relieved T4O’s suppressive effect on cSCC cell proliferation and motility.Mechanistically,T4O upregulates calpain-2 expression and promotes the cleavage ofβ-catenin and caspase-12,with siRNA-mediated calpain-2 knockdown mitigating T4O’s suppressive effects.Conclusion:These findings suggest that T4O’s antitumor activity in cSCC is mediated through the upregulation of calpain-2 expression and subsequent modulation ofβ-catenin and caspase-12.
基金supported by the National Natural Science Foundation of China(No.81874369)the Excellent Youth Project of the Hunan Provincial Department of Education(No.22B0388)the Project of Hunan Administration of Traditional Chinese Medicine(No.B2023143)。
文摘Five new flavan-4-ol glycosides jixueqiosides A-E(1-5)and two new flavan glycosides jixueqiosides F and G(6 and 7),along with twelve known flavan-4-ol glycosides(8-19),were isolated from the roots of Pronephrium penangianum.Comprehensive spectral analyses,X-ray single-crystal diffraction,and theoretical electronic circular dichroism(ECD)calculations established structures and absolute configurations.A single crystal structure of flavan-4-ol glycoside(14)was reported for the first time,while the characteristic ECD and NMR data for all isolated flavan-4-ol glycosides(1-5,8-19)were analyzed,establishing a set of empirical rules.Activity screening of these isolates showed that 8 and 9 could inhibit the proliferation of MDA-MB-231 and MCF-7 cells with IC50 values of 7.93±2.85μmol·L^(-1)and 5.87±1.58μmol·L^(-1)(MDA-MB-231),and 2.21±1.38μmol·L^(-1)and 3.52±1.55μmol·L^(-1)(MCF-7),respectively.Western blotting and flow cytometry analyses demonstrated that 8 and 9 dose-dependently induced apoptosis in MDA-MB-231 cells by up-regulating BAX,activating caspase-3 and down-regulating BCL-2.Additionally,compound 8 affected autophagy-related proteins,increasing the ratio of LC3-II/LC3-I and Beclin-1 levels to inhibit MDA-MB-231 cell proliferation.Moreover,anti-inflammatory studies indicated that 2,3,7,13,14,and 18 moderately inhibited tumor necrosis factor-α(TNF-α),interleukin-6(IL-6),and nitric oxide(NO)release.
基金supported by the National Natural Science Foundation of China(30600404)the Key Technologies R&D Program of China during the 10th Five-Year Plan Period(2004BA516A04).
文摘To study insecticidal mechanism of terpinen-4-ol, a main insecticidal composition in the essential oil of Sabina vulgaris, the 5th instar larvae of Mythimna separta, were investigated with terpinen-4-ol by topical application. The activities of phosphatase, glutathione S-transferase （GSTs）, cytochrome P450 （P450）, and polyphenol oxidase （PPO） of tested insects were determined in all poisoning stages, including exciting stage, convulsing stage, paralysis stage, and recover stage. The result showed that the activities of both acid phosphatase （ACP） and alkaline phosphatase （AKP） in treated insects were induced by terpinen-4-ol, but ACP was inhibited in paralysis stage. The activities of GSTs were inhibited in exciting stage, convulsing stage, and paralysis stage, but gradually recovered in recover stage. O-demethylase activity of cytochrome P450 was inhibited by terpinen-4-ol, and the inhibition rate in all poisoning stages were 26.27, 46.03, 80.24, and 90.22%, respectively. PPO activities were strongly inhibited by terpinen-4-ol both in vitro and in vivo. In conclusion, the activities of P450, GSTs, and PPO could have relation with toxicity of terpinen-4-ol against larvae of the Mythimna separta, but recover stage of the poisoning insects might be related to GSTs induced. As a new insecticide or synergist, terpinen- 4-ol has a potential value in field of insecticide resistance management.
基金supported by grants from the National Natural Science Foundation of China for Youth(grant number 32302753)Practice and Innovation Program of Graduated students in Jiangsu Province(grant number SJCX23_1992)the Priority Academic Program Development of Jiangsu Higher Education Institutions(PAPD).
文摘This study aims to elucidate intestinal injury from the perspective of intestinal epithelial cell homeostasis and to explore the modulatory roles of terpine-4-ol(a major bioactive component of tea tree oil).Forty 28-day-old piglets(7.82±0.43 kg)were randomly divided into 5 groups with 8 pigs per group.Piglets in the control(CON)and lipopolysaccharide(LPS)groups were fed a basal diet,while those in the remaining 3 groups were fed the basal diet supplemented with 30(LTP),60(MTP),or 90 mg/kg terpine4-ol(HTP),respectively.Piglets in the LPS and terpine-4-ol supplementation groups were intraperitoneally injected with 100μg/kg BW of LPS at the end of the 21-day growth period.Six hours after injection,6 piglets from each group were randomly selected and slaughtered to detect intestinal cell homeostasis.The results showed that the average daily weight gain(ADG)and average daily feed intake(ADFI)of piglets in MTP and HTP groups were higher than those in the CON group(P<0.05),whereas the feed conversion ratio(FCR)of piglets in LTP group was lower as compared to the CON group(P=0.007).Terpine-4-ol supplementation also decreased the diarrhea rate of piglets.Lipopolysaccharide challenge decreased the villus length and the ratio of villus length to crypt depth(V/C)in the jejunum(P<0.05),decreased the V/C ratio and increased the crypt depth in the ileum(P<0.05).In contrast,terpine-4-ol supplementation led to increased villus length and V/C ratio in the jejunum,raised the V/C ratio in the HTP group,and decreased crypt depth in the LTP and MTP groups in the ileum(P<0.05).Lipopolysaccharide reduced the number of antigen Ki-67 positive(Ki67^(+))cells and increased the number of caspase 3^(+)cells(P<0.05)in both the jejunum and ileum,whereas terpine-4-ol increased the number of Ki67^(+)cells in the crypts of the jejunum and ileum,while decreasing the number of caspase 3^(+)cells of the ileum and in the jejunum of MTP and HTP groups(P<0.05).Lipopolysaccharide downregulated the expression of the intestinal stem cell marker leucine-rich repeat-containing G-protein coupled receptor 5(Lgr5)(P<0.05,except for Lgr5 gene in the jejunum),while terpine-4-ol supplementation alleviated the effect.Lipopolysaccharide decreased the number of goblet cells and mucin 2(Muc2)secretion(P<0.05),whereas the number of goblet cells and Muc2 secretion in the small intestine of MTP group were increased(P<0.05).In addition,LPS injection led to a reduction in the expression of endocrine cell marker chromogranin A and absorption cell marker villin(P<0.05).Conversely,terpine-4-ol increased the abundance of endocrine cells and absorption cells in the small intestine(P<0.05).Moreover,LPS inhibited the expression of genes and proteins of wingless-type MMTV integration site family(Wnt)/β-catenin signaling pathway(P<0.05),whereas terpine-4-ol reversed this effect.In conclusion,terpine-4-ol supplementation improved growth performance,decreased diarrhea in piglets and alleviated the damage to the intestinal epithelial cell homeostasis under LPS challenge,probably via Wnt/β-catenin signaling activation.A dose of 60 mg terpine-4-ol per kilogram diet was recommended based on the present study.
基金supported by the National Natural Science Foundation of China (30600404)
文摘To reveal the insecticidal mechanism of terpinen-4-ol, the activity of Na＋,K＋-ATPase in insects tested were determined in vivo and in vitro. The results showed that terpinen-4-ol and its ester derivatives had strong contact activity to housefly and the contact toxicities of its derivatives except Z3 were all superior or equivalent to terpinen-4-ol. All the 7 compounds had strong inhibition towards activity of Na＋,K＋-ATPase. With poisoning symptom exacerbating, the inhibition rates were gradually increased. In vitro, the IC50 of terpinen-4-ol, Z1, Z2, Z4, Z5, and Z6 was 155.89, 197.98, 96.02, 121.36, 124.85, and 153.74 μg mL% respectively. There was well correlation between the LDs0 of terpinen-4-ol derivatives to housefly and the IC50 of terpinen-4-ol derivatives to Na＋,K＋-ATPase in housefly. In conclusion, Na＋,K＋-ATPase was likely the target of terpinen-4-ol against insects.
文摘A more feasibly convergent synthesis of selective estrogen receptor degrading agent(S)-8-(4-((1-(3-fluoropropyl)-pyrrolidin-3-yl)oxy)phenyl)-7-(4-hydroxyphenyl)-5,6-dihydronaphthalen-2-ol was reported,featured with concise work up and absence of regioselectivity dilemma.
基金National Natural Sci-ence Foundation of China(31670337)Research Project(ZYS2016-001)funded by Yunnan Key Laboratory for Wild Plant Resources.
文摘Zingiber cassumunar is an important plant used in traditional medicine and as a natural mosquito re-pellent.However,the compounds responsible for the repellent activity of the plant are still unknown.The aim of the study is to identify the components of Z.cassumunar essential oil that show repellent activity against Aedes albopictus.We also evaluated the larvicidal and adulticidal activities of Z.cassumunar essential oil against Ae.albopictus.In-cage mosquito repellent experiments showed that Z.cassumunar essential oil possessed moderate repellent activity with a minimum effective dose(MED)of 0.16±0.01 mg/cm^(20,compared to reference standard N,N-diethyl-3-methylbenzamide(DEET,0.03±0.01 mg/cm^(20).Bioassay-guided fractionation identified the major active compound of Z.cassumunar essential oil as(-)-terpinen-4-ol(1)(MED:0.19±0 mg/cm^(20).We also found that Z.cassumunar essential oil showed moderate larvicidal activity against first instar larvae of Ae.albopictus with a LC50(50%lethal concentration)of 44.9 mg/L after 24 h.Fumigation bioassays showed that Z.cassumunar essential oil exhibits moderate adulticidal activity against Ae.albopictus with a LC50 of 5.44%,while(-)-terpinen-4-ol showed significant adulticidal activity with a LC50 of 2.10%after 24 h.This study verifies that the Z.cassumunar essential oil has mosquito repellent activity,and that(-)-terpinen-4-ol is mainly responsible for this activity.Furthermore,this study provides scientific support for the folk usage of Z.cassumunar essential oil as mosquito repellent and indicates that Z.cassumunar essential oil and(-)-terpinen-4-ol can be used as plant-derived repellents and insecticides for mosquito control.
基金supported by the Great Research Project of National Major New Drug Development(No. 2009ZX09102-110)
文摘2-[3,5-Di-O-β-D-glucosyl-4-(3-methylbut-2-enyl)phenyl]benzofuran-6-ol,a new prenylated arylbenzofuran derivative was isolated from Morus alba L.Its structure was elucidated by various spectroscopic methods including MS,~1H NMR,^(13)C NMR,DEPT,~1H-~1HCOSY,HMQC and HMBC.
基金supported by Slovak Research and Development Agency (APVV-51-P06005 and APVV-27-P05205)the Scientific Grant Agency of the Ministry of Education of the Slovak Republic and the Slovak Academy of Sciences (2/6153/26)
文摘We compared two different strategies to increase the catches oflps typographus （L.）, particularly males, in pheromone-baited traps. The first of these strategies, the barrier approach, used alternating pheromone blends, targeting males and females respectively, in closely-spaced traps forming a barrier around forest stands. The second strategy, the single trap approach, used widely-spaced traps that were all baited with the same lure and intended to trap the highest possible numbers of males without compromising trapping of females. In the blend used for the barrier traps targeting primarily males, with a lower percentage of （4S）-cis-verbenol （cV）, the （-）-α-pinene was replaced step wise with （＋）-limonene at rates of 0%, 1%, 10%, 35%, 60% and 90%. This replacement had no significant effect on the numbers of responding 1. typographus males, but there was a slight effect on the percentage of males caught. In the attractant blend for the barrier traps targeting females, with a higher percentage of cV, the 2-methyl-3-buten-2-ol （MB） was replaced with 1-methoxy-2-propanol （MP） in a similar fashion as for the male-specific blends. The replacement did not significantly affect the catch of females. Thus, it is pos- sible to use the MP in the blend with cV and ipsdienol without significant change in catch efficacy. In the blends for single traps, the （-）-α- pinene was replaced with （＋）-limonene and MB with MP. The replacement of （-）-α-pinene had only a slight effect on the percentage of males, but the results suggest that replacing MB with MP in the blend will not significantly reduce trapping efficacy.
文摘Over the past few decades,complementary and alternative treatments have become increasingly popular worldwide.The purported therapeutic characteristics of natural products have come under increased scrutiny both in vitro and in vivo as part of efforts to legitimize their usage.One such product is tea tree oil(TTO),a volatile essential oil primarily obtained from the native Australian plant,Melaleuca alternifolia,which has diverse traditional and industrial applications such as topical preparations for the treatment of skin infections.Its anti-inflammatory-linked immunomodulatory actions have also been reported.This systematic review focuses on the anti-inflammatory effects of TTO and its main components that have shown strong immunomodulatory potential.An extensive literature search was performed electronically for data curation on worldwide accepted scientific databases,such as Web of Science,Google Scholar,PubMed,ScienceDirect,Scopus,and esteemed publishers such as Elsevier,Springer,Frontiers,and Taylor&Francis.Considering that the majority of pharmacological studies were conducted on crude oils only,the extracted data were critically analyzed to gain further insight into the prospects of TTO being used as a neuroprotective agent by drug formulation or dietary supplement.In addition,the active constituents contributing to the activity of TTO have not been well justified,and the core mechanisms need to be unveiled especially for anti-inflammatory and immunomodulatory effects leading to neuroprotection.Therefore,this review attempts to correlate the anti-inflammatory and immunomodulatory activity of TTO with its neuroprotective mechanisms.
基金Project supported by the National Natural Science Foundation of China （No. 20902073）, the Natural Science Foundation of Gansu Province （No. 096RJZA116） and Scientific and Technological Innovation Engineering Program of Northwest Normal University （No. nwnu-kjcxgc-03-64）.
文摘A highly efficient synthesis of novel pyrido[2,3-d]pyrimidin-4-ols was developed via an iodine-catalyzed tandem oxidative cyclization under focused microwave irradiation. Pyrido[2,3-d]pyrimidin-4-ols were obtained from easily available 2-amino-4-aryl-6-arylnicotinamides and benzylic amines with good to excellent yields.
文摘Essential oil from the leaves of Pistacia lentiscus L. growing in the Oran region in the west of Algeria was obtained by hydrodistillation with a 1.26 % yield on a dry weight basis. Spectrophotometric analyses were employed to highlight the scavenger capacity of this oil using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) test. Twenty compounds were identified by GC and CG/MS analyses, and the main part of the compounds of the oil was terpinene-4-ol (41.24%) and α-terpineol (7.31%), α-pinene (9.48%), limonene (09.11%), β-myrcene (10.5%), p-cymene (8.67%) and α-phellandrene (2.20%), β-caryophyllene (12.62%) as major compounds. The DPPH test shows that Pistacia lentiscus essential oil possesses antiradical activity. A linear correlation (correlation coefficient R<sup>2</sup> = 0.995, P Pistacia lentiscus essential oil.
文摘This study aims to explore the analgesic ingredients and mechanism of Cinnamomum camphora essential oil(CCEO).The constituents in CCEO were characterized qualitatively by gas chromatography-mass spectrometry.Targets related to active ingredients were collected by PubChem and Swiss Target Prediction.Targets related to pain were screened by TTD and OMIM database,and compound-target network was established by Cytoscape software.Gene ontology(GO)function and Kyoto encyclopedia of genes and genomes(KEGG)pathway enrichment analysis of targets were carried out by DAVID database.Protein-protein interaction(PPI)network was established and analyzed by STRING database.Molecular docking method was used to verify the interaction between main components and relevant core targets.A total of 13 compounds were identified in CCEO,and 58 related targets were predicted.GO function enrichment analysis revealed that the selected targets were mainly involved in biological processes such as chemical synaptic transmission and molecular function such as neurotransmitter receptor activity;24 signal pathways were screened by KEGG pathway enrichment analysis,including neuroactive ligand-receptor interaction,retrograde endocannabinoid signaling and calcium signaling pathway.Docking results showed that the main constituents had certain affinities with the key targets.The active ingredients in CCEO regulated multiple signaling pathways to ameliorate pain through AR,ACHE,ESR1,GABRG2,PTGS2 and PPARγ.
基金supported by the National Natural Science Foundation of China(No.22278380)China Postdoctoral Science Foundation(Nos.2024M762994 and GZC20232392)supported by the project of Yunnan Key Laboratory of Electromagnetic Materials and Devices,Yunnan University(No.ZZ2024009).
文摘Electrocatalytic conversion presents a promising alternative to conventional industrial catalysis.While aqueous-phase electrocatalysis has achieved notable advancements,oil-water immiscible systems remain challenging due to restricted reaction flux at multiphase interfaces.To address the limitation,we engineered a biphasic reaction system featuring a tailored oil-water catalytic interface in cyclohexene oxidation reaction(COR).The system employed a catalyst-loaded porous electrode as an active phase domain,enabling spatial separation of cyclohexene(organic phase)and electrolyte(aqueous phase).The tailored oil-water interface enhanced the interfacial mass transfer of substrate-catalysts and facilitated the spontaneous migration of 2-cyclohexen-1-ol into the aqueous phase,thereby streamlining product separation.Notably,polyaniline(PANI)modification on Co_(3)O_(4)enhanced surface lipophilicity,promoting cyclohexene adsorption and accelerating the COR catalytic kinetics(Co^(3+)-O+cyclohexene-H+e-→Co^(2+)-OH+2-cyclohexen-1-ol).The synergistic effects of optimized interfacial engineering and catalyst functionalization achieved exceptional performance:a current density of 45 mA·cm^(-2)at 1.6 V vs.reversible hydrogen electrode(V_(RHE)),coupled with 96.2%selectivity and 82.9%Faradaic efficiency.This work establishes an innovative paradigm for electrocatalytic conversions in oil-water immiscible systems through rational interface design and catalyst surface modulation.
基金Science and Technology Project of Zhongshan,China(20071A036)
文摘Objective To study the chemical constituents of Pronephrium triphyllum.Methods The chemical constituents in the plant were isolated and purified with silica gel and Sephadex LH-20.Their structures were identified by analyses of spectral data and physicochemical properties.Results Six compounds were isolated and identified as shelincaoide A(1),n-butyl-β-D-fructopyranoside(2),triphyllin A(3),6,7-di-hydroxycoumarin(4),daucosterol(5),andβ-sitosterol(6),respectively.Conclusion Compound 1 is found to be a new compound.Compounds 2 and 4 are firstly isolated from the plants in Pronephrium Presl.and all compounds except 3 are obtained from the species for the first time.
