Teucrifarides A-D(1-4),four previously unreported neo-clerodane-type diterpenoids,combined with sixteen known analogs(5-20),were purified from Teucrium quadrifarium.The absolute forma of compounds 1-4 were determined ...Teucrifarides A-D(1-4),four previously unreported neo-clerodane-type diterpenoids,combined with sixteen known analogs(5-20),were purified from Teucrium quadrifarium.The absolute forma of compounds 1-4 were determined via spectroscopic and ECD calculation methods,together with X-ray crystallography experiments.Among them,compound 1 possessed a 5,20-epoxy ring featuring a unique cage-like 12-oxatricyclo[5.3.2.0^(1,6)]undecane skeleton.Meanwhile,2 incorporated a 6,20-epoxy ring with a novel 12-oxatricyclo[6.2.2.0^(2,7)]undecane skeleton.Compounds 1 and 12 exhibited significant inhibitory effects against HT-22 cells ferroptosis induced by RSL3,with EC_(50)values of 11.8±1.0μM,and 4.52±1.24μM,respectively.Moreover,ROS accumulation in HT22 cells treated with compound 1 was also observed.展开更多
Objective:To explore the antibacterial effect of the alcoholic extracts of aerial parts of Teucrium polium,native in Iran on some pathogenic bacteria.Methods:Antibacterial activity of ethanolic extract(50 to 400 mg/mL...Objective:To explore the antibacterial effect of the alcoholic extracts of aerial parts of Teucrium polium,native in Iran on some pathogenic bacteria.Methods:Antibacterial activity of ethanolic extract(50 to 400 mg/mL) and methanolic extract(400 and 600 mg/mL) was evaluated by disc diffusion method.Results:The ethanolic extract results showed that Bacillus anthracis was the most sensitive species,while Escherichia coli and Proteus mirabilis were more resistant than others.In the case of the methanolic extract,Bordetella bronchiseptica was the most sensitive and Proteus mirabilis and Arcanobacterium pyogenes were the most resistant species.The hydroalcoholic extract of Teucrium polium had a relatively satisfactory effect on Salmonella typhi. The minimal inhibitory concentration(MIC) of Staphylococcus aureus and Salmonella typhi was 40 mg/mL and Bordetella bronchiseptica and Bacillus anthracis was 10 mg/mL.The minimal bactericidal concentration(MBC) against Bacillus anthracis was 10 mg/mL while against other species were not found(】200 mg/mL).The methanolic extract had also synergistic effect with methicillin,vancomycin against Staphylococcus aureus and with novobiocin against Salmonella typhi.Conclusions:These results suggest that this plant contains relatively good antibacterial activity and it can be used as a source of antiseptic compounds for medicinal uses.展开更多
Objective:To determine the chemical composition of essential oils and lipid constituents of Ballola andreuzziana(B.andreuzziana),Teucrium zanonii(T.zanonii) and Verbena tenuisecta(V. tenuisecta) growing in Libya,and t...Objective:To determine the chemical composition of essential oils and lipid constituents of Ballola andreuzziana(B.andreuzziana),Teucrium zanonii(T.zanonii) and Verbena tenuisecta(V. tenuisecta) growing in Libya,and to test the antibacterial activity of different extracts of Teucrium zanonii.Methods:The volatile oils of all plants were extracted by hydrodistillation method and analyzed by GC/MS method.The lipid constituents of plants were obtained by extraction with petroleum ether and fractionated into fatty alcohols,fatty acids and unsapoinfiable matters. Antibacterial activity of T.zanonii extracts and antioxidant activity of different extracts of T. zanonii were also studied.Results:The volate oil of B.andreuzziana was found to consists of 20 compounds in which caryophyllin is the main one(63.1%),the volatile oil of T.zanonii consists of 74 compounds in which germacrene-D was the main compound,while the volatile oil of V. tenuisecta consists of 13 compounds with l-octen-3- ol as a major constituent(52.87%).The study of antimicrobial activity of different extracts of V.tenuisecta showed that,both methanol and butanol extracts exhibited the highest activity against Mycobacterium phlei(M.pblei) and Candida albicans(C.albicans) respectively,while petroleum ether,fatty alcohols and unsaponifiable fractions had no antimicrobial activity against all the tested microorganisms. Investigation of the antioxidant activity of different extracts of T.zanonii using DPPH method proved that,the ethyl acetate and butanol fractions showed the highest activity where the inhibition percentage(1%) are 93.6 and 92.1 respectively.Conclusions:This is the first report about the volatile oils of these plants where T.zanonii have the highest content and the highest number of the identified compounds.The study of antioxidant T.zanonii extracts proved that,the ethyl acetate,butanol and aqueous extracts have the highest antioxidant activity.Methanol and butanol extracts of V.tenuisecta exhibited the highest activity against M.phlei and C.albicans respectively.展开更多
A new monoterpenoid,4,5,8-trihydroxy-6（7）-en-decenoic acid γ-lactone（1） and six known compounds,3,7-dimethyloct-1-ene-3,6,7-triol（2）,2,8-bornanediol（3）,1-（4-hydroxyphenyl）ethane-1,2-diol（4）,2-（3-methoxy-...A new monoterpenoid,4,5,8-trihydroxy-6（7）-en-decenoic acid γ-lactone（1） and six known compounds,3,7-dimethyloct-1-ene-3,6,7-triol（2）,2,8-bornanediol（3）,1-（4-hydroxyphenyl）ethane-1,2-diol（4）,2-（3-methoxy-4-hydroxyphenyl）-propane-1,3-diol（5）,indole-3-carboxylic acid（6）,and 3-hydroxy-benzenemethanol（7） were isolated from the whole parts of Teucrium viscidum.Their structures were established by a combination of spectroscopic data analysis,besides comparison with literature data.Compounds 2–7 described above were isolated from this genus for the first time.展开更多
Salvia microphylla and Teucrium polium are medicinal and aromatic plants with ethnobotanical uses.The present study was conducted to investigate the chemical composition of Salvia microphylla and Teucrium polium essen...Salvia microphylla and Teucrium polium are medicinal and aromatic plants with ethnobotanical uses.The present study was conducted to investigate the chemical composition of Salvia microphylla and Teucrium polium essential oils,the secondary metabolites,and the biological activities of their infusion and methanolic(MeOH)extracts.Essential oils were extracted by hydrodistillation from shoots Salvia microphylla and Teucrium polium.Phenolic content,antioxidant and antimicrobial activities were determined.Gas chromatography-mass spectrometry(GCMS)results showed the presence of significant qualitative and quantitative variations for the composition of the both essential oils(EO).Salvia microphylla EO were most complex and present 70 compounds with the major components wereβ-caryophyllene(13.32%),1,8 cineole(11.25%),Cis p-Menthane-3-one(10.74%),andβ-Selinenol(9.71%).Where in the Teucrium polium EO,45 compounds were identified with the important components areβ-cadinene(10%),β-citronellol(8.5%),Carvacrol(7.63%),and Eugenol(7.15%).Obtained results showed that both plant are very rich in secondary metabolites.Extracts isolated from Salvia microphylla presented the highest contents in the phenolic compound than extracted from Teucrium polium.The antioxidant activity data demonstrated that all extracts showed strong antioxidant and radical scavenging activities.Essential oil and methanol extracts presented a potential for antimicrobial activities against all tested microorganisms.The obtained results highlight the potential use of Salvia microphylla and Teucrium polium as possible natural antioxidant substances and sources of bioactive molecules.展开更多
A nco—clcrodane diterpcne, teuponin, was isolated from the aerial parts of Teucrium japonicum. Its structure was established as (12S)—19—nor—neo—clcroda— 15a—hydroxy—4,13-diene— 16,15;18,6β;20,12-triolide by...A nco—clcrodane diterpcne, teuponin, was isolated from the aerial parts of Teucrium japonicum. Its structure was established as (12S)—19—nor—neo—clcroda— 15a—hydroxy—4,13-diene— 16,15;18,6β;20,12-triolide by spcctroscopic means. The absolute configuration was determined by X—ray diffraction analysis and CD spectrum.展开更多
A new chlorine-containing neo-clerodane diterpene, teupernin D, was isolated from the aerial parts of Teucrium pernyi. The structure for teupernin D was established as (12S) -15, 16-epoxy-8β-hydroxy-17-chloro-19-nor1...A new chlorine-containing neo-clerodane diterpene, teupernin D, was isolated from the aerial parts of Teucrium pernyi. The structure for teupernin D was established as (12S) -15, 16-epoxy-8β-hydroxy-17-chloro-19-nor10α-neo-cleroda-4, 13(16), 14-triene-18,6β;20,12-diolide on the basis of spectral evidence. The absolute configuration was established by CD spectrum and confirmed by X-ray crystallographic analysis.展开更多
Three furanoid ent-clerodane diterpenoids,teupernin A,B and C have been isolated from the acetone extract of Teucrium pernyi Franch.Their structures were established by spectroscopic means(UV,IR,MS,~1H NMR,^(13)C NMR,...Three furanoid ent-clerodane diterpenoids,teupernin A,B and C have been isolated from the acetone extract of Teucrium pernyi Franch.Their structures were established by spectroscopic means(UV,IR,MS,~1H NMR,^(13)C NMR,H-H COSY,C-H COSY and NOE)and by comparison with related compounds.展开更多
The antioxidative activities of subfractions;methanol (CE), chloroform (CHE) and ethyl acetate (EAE) of Teucrium polium extracts (TPE) were investigated. HPLC analysis of the plant revealed the existence of procyanidi...The antioxidative activities of subfractions;methanol (CE), chloroform (CHE) and ethyl acetate (EAE) of Teucrium polium extracts (TPE) were investigated. HPLC analysis of the plant revealed the existence of procyanidins B1 and B2, gallic acid, catechin and epicatechin. All the extracts showed inhibitory properties on xanthine oxidase, with IC50 ranging from 0.80 ± 0.07 to 11.76 ± 0.50 μM/quercetin equivalent. In the cellular system, all the extracts showed a protec-tive effect greater than those of quercetin, rutin and gallic acid against t-BHP induced oxidative damages in human erythrocytes. These results were clearly confirmed by a modified thiobarbituric acid-reactive species (TBARS), and β-carotene/linoleic acid assay which demonstrated that CHE possess an inhibition ratio of the linoleic acid oxidation (83.11%) close to that of BHT (96.77%). In addition, the results showed that the extracts possess a potent DPPH radical scavenging activity and gave a reduction power greater than rutin, quercetin, gallic acid and ascorbic acid in FRAP assay. These results show that Teucrium polium extracts have strong antioxidant effects and may have some clinical benefits.展开更多
Lung cancer is the first common malignancy worldwide;in view of the limited success of available treatment modalities for this cancer, alternative and complementary strategies need to be developed. On the other hand, ...Lung cancer is the first common malignancy worldwide;in view of the limited success of available treatment modalities for this cancer, alternative and complementary strategies need to be developed. On the other hand, Teucrium polium (TP) is a medicinal plant that has been used for more than two thousand years for treating many diseases such as abdominal pain, indigestion and diabetes in the Middle East. However, the effect of TP plant extract on hu-man non-small cell lung cancer (NSCLC) has not been investigated yet. In this study, we exam-ined the effects of TP extract on cell prolifera-tion, cell cycle progression and cell death in H322 and A549 lung cell lines. Our results show that TP plant extract inhibits cell proliferation and deregulates cell cycle progression. More importantly, TP plant extract causes a dramatic cell death in both cell lines in comparison with untreated cells. Our data suggest that this plant extract could have an important therapeutic role in the treatment of human NSCLC.展开更多
A new ursane-type triterpene,3 beta-hydroxy-urs-5(6)-en-28-oic acid 1,was isolated from the aerial parts of Teucrium integrifolium and characterized.The structure of this new compound was mainly established by 2D NMR ...A new ursane-type triterpene,3 beta-hydroxy-urs-5(6)-en-28-oic acid 1,was isolated from the aerial parts of Teucrium integrifolium and characterized.The structure of this new compound was mainly established by 2D NMR techniques(COSY,HETCOR,HMBC).展开更多
Teucrium chamaedrys,commonly known as wall germander,is a small woody shrub native to the Mediterranean region.Its name is derived from the Greek words meaning‘‘ground oak,’’as its tiny leaves resemble those of an...Teucrium chamaedrys,commonly known as wall germander,is a small woody shrub native to the Mediterranean region.Its name is derived from the Greek words meaning‘‘ground oak,’’as its tiny leaves resemble those of an oak tree.Teucrium species are prolific producers of diterpenes,endowing them with valuable properties widely utilized in traditional and modern medicine.Sequencing and assembly of the 3-Gbp tetraploid T.chamaedrys genome revealed 74 diterpene synthase genes,with a substantial number of these genes clustered at four synteny genomic loci,each harboring a copy of a large diterpene biosynthetic gene cluster.Comparative genomics revealed that this cluster is conserved in the closely related species Teucrium marum.Along with the presence of several cytochrome p450 sequences,this region is among the largest biosynthetic gene clusters identified.Teucrium is well known for accumulating clerodane-type diterpenoids,which are produced from a kolavenyl diphosphate precursor.To elucidate the complex biosynthetic pathways of these medicinal compounds,we identified and functionally characterized several kolavenyl diphosphate synthases from T.chamaedrys.The remarkable chemical diversity and tetraploid nature of T.chamaedrys make it a valuable model for studying genomic evolution and adaptation in plants.展开更多
Teucrium polium is a dwarf sub-shrub usually 30-60 cm high with many branches, which is fairly distributed throughout Iran, with its flowering being season mainly from April to July. The plant was collected during its...Teucrium polium is a dwarf sub-shrub usually 30-60 cm high with many branches, which is fairly distributed throughout Iran, with its flowering being season mainly from April to July. The plant was collected during its flowering season in Baghmalek region in the North-East of Khuzestan province, Iran. After the identification of the genus, species and variety of the plant, the dried whole plant （flowers, fruits and the leaves） was steam distilled with different methods. The isolated essential oil was dried over anhydrous sodium sulphate and stored at 4-6 ℃. Analysis of the essential oil was carried out by GC-MS technique. At least 10 major components were identified （3-carene/α-pinene, β-phellandrene, limonene, germacrene, β-bourbonene, β-caryophylene, γ-muurolene, γ-elemene, spathulenol, β-eudesmol） （totally 97.02%）. Also, successive TLC and column chromatography of the essential oil resulted in the separation of four fractions. Based upon 1^H NMR, IR and mass spectra, the fractions with Rf=0.12 and 0.93 were determined as gualol and a mixture of α-pinene, β-phellandrene and limonene, respectively.展开更多
The utilization of natural materials in the post-harvest process of agricultural products is necessary for the production of safe food.In recent years,the use of essential oil extracted from aromatic plants has shown ...The utilization of natural materials in the post-harvest process of agricultural products is necessary for the production of safe food.In recent years,the use of essential oil extracted from aromatic plants has shown significant potential for insect pest management.Toxicity and antifeedant effects of essential oil isolated from aerial parts of Teucrium polium L.have been investigated against the red flour beetle,Tribolium castaneum Herbst,as one of the most detrimental insect pests of post-harvest cereals in the present study.The chemical profile of this oil was also assessed by gas chromatography-mass spectrometry(GC-MS)and lycopersene(26.00%),dodecane(14.78%),1,5-dimethyl decahydronaphthalene(9.27%)and undecane(7.18%)were identified as main components.For evaluation of the fumigant toxicity and antifeedant effects using multiple regression analysis,a quadratic polynomial and linear equation were obtained,respectively.Adequacy and accuracy of the fitted models were checked through analysis of variance.T.polium essential oil exhibited significant fumigant toxicity on the T.castaneum adults and based on modeling using RSM,the concentration of 20μl/l and 72 min exposure time was calculated as the optimum conditions for 97.97%mortality with 87.8%desirability.A concentration of 14.13μl/l was also estimated as the optimum value for 94.66%Feeding Deferens Index with 92%desirability.The mortality and anti-nutritional effect,in general,increased with increasing of exposure times and the essential oil concentrations.Results designated a great potential of T.polium essential oil for management of the red flour beetle.Further,it was found that the Response Surface Methodology was a promising method for the prediction of these bio-effects.展开更多
Objective: Black bean aphid(Aphis fabae) is one of the most important greenhouse and crop pests with a wide range of hosts, which causes damages through feeding on vegetable sap and transmitting viral diseases. Curren...Objective: Black bean aphid(Aphis fabae) is one of the most important greenhouse and crop pests with a wide range of hosts, which causes damages through feeding on vegetable sap and transmitting viral diseases. Currently, chemical methods are mainly used to control this pest. Considering the adverse effects of pesticides, it is essential to apply less chemical pesticide in pest control programs. The lethal and sublethal effects of the essential oil(EO) of Teucrium polium leaves on one-day-old adults of black bean aphid were investigated under laboratory conditions.Method: The bioassay was evaluated at the concentrations of 0.88-12 μL/L air, for 24 h after treatment.Reproductive life table parameters of new emerged aphid surveyed at sub-lethal concentrations(LC20 and LC40) of EO and the biological reproductive table was calculated by Jackknife method.Results: The mortality rate increased significantly with the increasing of EO concentration. The estimated LC50 value was 4.5 μL/L air. Laboratory exposure to sublethal concentrations of EO caused significant decrease in adult female longevity and fertility of surviving aphids and as a result caused significant reduction in the intrinsic rate of natural increase(rmvalue).Conclusion: The results of this study revealed that EO of T. polium could be used as a potential control agent for the aphid.展开更多
基金supported by the National Natural Science Foundation of China(32100322,32460112,32060100)and the Science and Technology Department of Guizhou Province(QKHZC[2022]019).
文摘Teucrifarides A-D(1-4),four previously unreported neo-clerodane-type diterpenoids,combined with sixteen known analogs(5-20),were purified from Teucrium quadrifarium.The absolute forma of compounds 1-4 were determined via spectroscopic and ECD calculation methods,together with X-ray crystallography experiments.Among them,compound 1 possessed a 5,20-epoxy ring featuring a unique cage-like 12-oxatricyclo[5.3.2.0^(1,6)]undecane skeleton.Meanwhile,2 incorporated a 6,20-epoxy ring with a novel 12-oxatricyclo[6.2.2.0^(2,7)]undecane skeleton.Compounds 1 and 12 exhibited significant inhibitory effects against HT-22 cells ferroptosis induced by RSL3,with EC_(50)values of 11.8±1.0μM,and 4.52±1.24μM,respectively.Moreover,ROS accumulation in HT22 cells treated with compound 1 was also observed.
文摘Objective:To explore the antibacterial effect of the alcoholic extracts of aerial parts of Teucrium polium,native in Iran on some pathogenic bacteria.Methods:Antibacterial activity of ethanolic extract(50 to 400 mg/mL) and methanolic extract(400 and 600 mg/mL) was evaluated by disc diffusion method.Results:The ethanolic extract results showed that Bacillus anthracis was the most sensitive species,while Escherichia coli and Proteus mirabilis were more resistant than others.In the case of the methanolic extract,Bordetella bronchiseptica was the most sensitive and Proteus mirabilis and Arcanobacterium pyogenes were the most resistant species.The hydroalcoholic extract of Teucrium polium had a relatively satisfactory effect on Salmonella typhi. The minimal inhibitory concentration(MIC) of Staphylococcus aureus and Salmonella typhi was 40 mg/mL and Bordetella bronchiseptica and Bacillus anthracis was 10 mg/mL.The minimal bactericidal concentration(MBC) against Bacillus anthracis was 10 mg/mL while against other species were not found(】200 mg/mL).The methanolic extract had also synergistic effect with methicillin,vancomycin against Staphylococcus aureus and with novobiocin against Salmonella typhi.Conclusions:These results suggest that this plant contains relatively good antibacterial activity and it can be used as a source of antiseptic compounds for medicinal uses.
文摘Objective:To determine the chemical composition of essential oils and lipid constituents of Ballola andreuzziana(B.andreuzziana),Teucrium zanonii(T.zanonii) and Verbena tenuisecta(V. tenuisecta) growing in Libya,and to test the antibacterial activity of different extracts of Teucrium zanonii.Methods:The volatile oils of all plants were extracted by hydrodistillation method and analyzed by GC/MS method.The lipid constituents of plants were obtained by extraction with petroleum ether and fractionated into fatty alcohols,fatty acids and unsapoinfiable matters. Antibacterial activity of T.zanonii extracts and antioxidant activity of different extracts of T. zanonii were also studied.Results:The volate oil of B.andreuzziana was found to consists of 20 compounds in which caryophyllin is the main one(63.1%),the volatile oil of T.zanonii consists of 74 compounds in which germacrene-D was the main compound,while the volatile oil of V. tenuisecta consists of 13 compounds with l-octen-3- ol as a major constituent(52.87%).The study of antimicrobial activity of different extracts of V.tenuisecta showed that,both methanol and butanol extracts exhibited the highest activity against Mycobacterium phlei(M.pblei) and Candida albicans(C.albicans) respectively,while petroleum ether,fatty alcohols and unsaponifiable fractions had no antimicrobial activity against all the tested microorganisms. Investigation of the antioxidant activity of different extracts of T.zanonii using DPPH method proved that,the ethyl acetate and butanol fractions showed the highest activity where the inhibition percentage(1%) are 93.6 and 92.1 respectively.Conclusions:This is the first report about the volatile oils of these plants where T.zanonii have the highest content and the highest number of the identified compounds.The study of antioxidant T.zanonii extracts proved that,the ethyl acetate,butanol and aqueous extracts have the highest antioxidant activity.Methanol and butanol extracts of V.tenuisecta exhibited the highest activity against M.phlei and C.albicans respectively.
基金Hubei Provincial Outstanding Young and Middle-aged Science and Technology Innovation Team Project(Grant No.T201813)
文摘A new monoterpenoid,4,5,8-trihydroxy-6（7）-en-decenoic acid γ-lactone（1） and six known compounds,3,7-dimethyloct-1-ene-3,6,7-triol（2）,2,8-bornanediol（3）,1-（4-hydroxyphenyl）ethane-1,2-diol（4）,2-（3-methoxy-4-hydroxyphenyl）-propane-1,3-diol（5）,indole-3-carboxylic acid（6）,and 3-hydroxy-benzenemethanol（7） were isolated from the whole parts of Teucrium viscidum.Their structures were established by a combination of spectroscopic data analysis,besides comparison with literature data.Compounds 2–7 described above were isolated from this genus for the first time.
基金The authors acknowledge funding supported by Campus France as part of the Scientific Stay at High Level received by AK and supported by CRITTBois and LERMAB of University of Lorraine,Epinal,France.
文摘Salvia microphylla and Teucrium polium are medicinal and aromatic plants with ethnobotanical uses.The present study was conducted to investigate the chemical composition of Salvia microphylla and Teucrium polium essential oils,the secondary metabolites,and the biological activities of their infusion and methanolic(MeOH)extracts.Essential oils were extracted by hydrodistillation from shoots Salvia microphylla and Teucrium polium.Phenolic content,antioxidant and antimicrobial activities were determined.Gas chromatography-mass spectrometry(GCMS)results showed the presence of significant qualitative and quantitative variations for the composition of the both essential oils(EO).Salvia microphylla EO were most complex and present 70 compounds with the major components wereβ-caryophyllene(13.32%),1,8 cineole(11.25%),Cis p-Menthane-3-one(10.74%),andβ-Selinenol(9.71%).Where in the Teucrium polium EO,45 compounds were identified with the important components areβ-cadinene(10%),β-citronellol(8.5%),Carvacrol(7.63%),and Eugenol(7.15%).Obtained results showed that both plant are very rich in secondary metabolites.Extracts isolated from Salvia microphylla presented the highest contents in the phenolic compound than extracted from Teucrium polium.The antioxidant activity data demonstrated that all extracts showed strong antioxidant and radical scavenging activities.Essential oil and methanol extracts presented a potential for antimicrobial activities against all tested microorganisms.The obtained results highlight the potential use of Salvia microphylla and Teucrium polium as possible natural antioxidant substances and sources of bioactive molecules.
文摘A nco—clcrodane diterpcne, teuponin, was isolated from the aerial parts of Teucrium japonicum. Its structure was established as (12S)—19—nor—neo—clcroda— 15a—hydroxy—4,13-diene— 16,15;18,6β;20,12-triolide by spcctroscopic means. The absolute configuration was determined by X—ray diffraction analysis and CD spectrum.
文摘A new chlorine-containing neo-clerodane diterpene, teupernin D, was isolated from the aerial parts of Teucrium pernyi. The structure for teupernin D was established as (12S) -15, 16-epoxy-8β-hydroxy-17-chloro-19-nor10α-neo-cleroda-4, 13(16), 14-triene-18,6β;20,12-diolide on the basis of spectral evidence. The absolute configuration was established by CD spectrum and confirmed by X-ray crystallographic analysis.
文摘Three furanoid ent-clerodane diterpenoids,teupernin A,B and C have been isolated from the acetone extract of Teucrium pernyi Franch.Their structures were established by spectroscopic means(UV,IR,MS,~1H NMR,^(13)C NMR,H-H COSY,C-H COSY and NOE)and by comparison with related compounds.
文摘The antioxidative activities of subfractions;methanol (CE), chloroform (CHE) and ethyl acetate (EAE) of Teucrium polium extracts (TPE) were investigated. HPLC analysis of the plant revealed the existence of procyanidins B1 and B2, gallic acid, catechin and epicatechin. All the extracts showed inhibitory properties on xanthine oxidase, with IC50 ranging from 0.80 ± 0.07 to 11.76 ± 0.50 μM/quercetin equivalent. In the cellular system, all the extracts showed a protec-tive effect greater than those of quercetin, rutin and gallic acid against t-BHP induced oxidative damages in human erythrocytes. These results were clearly confirmed by a modified thiobarbituric acid-reactive species (TBARS), and β-carotene/linoleic acid assay which demonstrated that CHE possess an inhibition ratio of the linoleic acid oxidation (83.11%) close to that of BHT (96.77%). In addition, the results showed that the extracts possess a potent DPPH radical scavenging activity and gave a reduction power greater than rutin, quercetin, gallic acid and ascorbic acid in FRAP assay. These results show that Teucrium polium extracts have strong antioxidant effects and may have some clinical benefits.
基金the Canadian Institutes for Health Research (CIHR) the Syrian society against cancer
文摘Lung cancer is the first common malignancy worldwide;in view of the limited success of available treatment modalities for this cancer, alternative and complementary strategies need to be developed. On the other hand, Teucrium polium (TP) is a medicinal plant that has been used for more than two thousand years for treating many diseases such as abdominal pain, indigestion and diabetes in the Middle East. However, the effect of TP plant extract on hu-man non-small cell lung cancer (NSCLC) has not been investigated yet. In this study, we exam-ined the effects of TP extract on cell prolifera-tion, cell cycle progression and cell death in H322 and A549 lung cell lines. Our results show that TP plant extract inhibits cell proliferation and deregulates cell cycle progression. More importantly, TP plant extract causes a dramatic cell death in both cell lines in comparison with untreated cells. Our data suggest that this plant extract could have an important therapeutic role in the treatment of human NSCLC.
文摘A new ursane-type triterpene,3 beta-hydroxy-urs-5(6)-en-28-oic acid 1,was isolated from the aerial parts of Teucrium integrifolium and characterized.The structure of this new compound was mainly established by 2D NMR techniques(COSY,HETCOR,HMBC).
基金support of the Neogen Land Grant Prize,an endowed grant program administered by the Office of Research and Innovation at Michigan State University(MSU),which supports graduate students in translating their research into real-world applications that positively impact society and the US economyfunded by a National Science Foundation(NSF)-IMPACTS Training Grant(DGE-1828149)+6 种基金funded by NSF Dimensions of Biodiversity(DEB 1737898)supported by the National Institute of General Medical Sciences of the National Institutes of Health under award number T32 GM110523the US Department of Energy Great Lakes Bioenergy Research Center Cooperative Agreement DESC0018409funding from the Department of Biochemistry and Molecular Biology at MSU and support from AgBioResearch(MICL02454)supported in part by the National Science Foundation under Grant number 1737898funding from the University of Georgia,the Georgia Research Alliance,and Georgia Seed Developmentsupport from the NSF under grant number ISO-2029959.
文摘Teucrium chamaedrys,commonly known as wall germander,is a small woody shrub native to the Mediterranean region.Its name is derived from the Greek words meaning‘‘ground oak,’’as its tiny leaves resemble those of an oak tree.Teucrium species are prolific producers of diterpenes,endowing them with valuable properties widely utilized in traditional and modern medicine.Sequencing and assembly of the 3-Gbp tetraploid T.chamaedrys genome revealed 74 diterpene synthase genes,with a substantial number of these genes clustered at four synteny genomic loci,each harboring a copy of a large diterpene biosynthetic gene cluster.Comparative genomics revealed that this cluster is conserved in the closely related species Teucrium marum.Along with the presence of several cytochrome p450 sequences,this region is among the largest biosynthetic gene clusters identified.Teucrium is well known for accumulating clerodane-type diterpenoids,which are produced from a kolavenyl diphosphate precursor.To elucidate the complex biosynthetic pathways of these medicinal compounds,we identified and functionally characterized several kolavenyl diphosphate synthases from T.chamaedrys.The remarkable chemical diversity and tetraploid nature of T.chamaedrys make it a valuable model for studying genomic evolution and adaptation in plants.
文摘Teucrium polium is a dwarf sub-shrub usually 30-60 cm high with many branches, which is fairly distributed throughout Iran, with its flowering being season mainly from April to July. The plant was collected during its flowering season in Baghmalek region in the North-East of Khuzestan province, Iran. After the identification of the genus, species and variety of the plant, the dried whole plant （flowers, fruits and the leaves） was steam distilled with different methods. The isolated essential oil was dried over anhydrous sodium sulphate and stored at 4-6 ℃. Analysis of the essential oil was carried out by GC-MS technique. At least 10 major components were identified （3-carene/α-pinene, β-phellandrene, limonene, germacrene, β-bourbonene, β-caryophylene, γ-muurolene, γ-elemene, spathulenol, β-eudesmol） （totally 97.02%）. Also, successive TLC and column chromatography of the essential oil resulted in the separation of four fractions. Based upon 1^H NMR, IR and mass spectra, the fractions with Rf=0.12 and 0.93 were determined as gualol and a mixture of α-pinene, β-phellandrene and limonene, respectively.
文摘The utilization of natural materials in the post-harvest process of agricultural products is necessary for the production of safe food.In recent years,the use of essential oil extracted from aromatic plants has shown significant potential for insect pest management.Toxicity and antifeedant effects of essential oil isolated from aerial parts of Teucrium polium L.have been investigated against the red flour beetle,Tribolium castaneum Herbst,as one of the most detrimental insect pests of post-harvest cereals in the present study.The chemical profile of this oil was also assessed by gas chromatography-mass spectrometry(GC-MS)and lycopersene(26.00%),dodecane(14.78%),1,5-dimethyl decahydronaphthalene(9.27%)and undecane(7.18%)were identified as main components.For evaluation of the fumigant toxicity and antifeedant effects using multiple regression analysis,a quadratic polynomial and linear equation were obtained,respectively.Adequacy and accuracy of the fitted models were checked through analysis of variance.T.polium essential oil exhibited significant fumigant toxicity on the T.castaneum adults and based on modeling using RSM,the concentration of 20μl/l and 72 min exposure time was calculated as the optimum conditions for 97.97%mortality with 87.8%desirability.A concentration of 14.13μl/l was also estimated as the optimum value for 94.66%Feeding Deferens Index with 92%desirability.The mortality and anti-nutritional effect,in general,increased with increasing of exposure times and the essential oil concentrations.Results designated a great potential of T.polium essential oil for management of the red flour beetle.Further,it was found that the Response Surface Methodology was a promising method for the prediction of these bio-effects.
文摘Objective: Black bean aphid(Aphis fabae) is one of the most important greenhouse and crop pests with a wide range of hosts, which causes damages through feeding on vegetable sap and transmitting viral diseases. Currently, chemical methods are mainly used to control this pest. Considering the adverse effects of pesticides, it is essential to apply less chemical pesticide in pest control programs. The lethal and sublethal effects of the essential oil(EO) of Teucrium polium leaves on one-day-old adults of black bean aphid were investigated under laboratory conditions.Method: The bioassay was evaluated at the concentrations of 0.88-12 μL/L air, for 24 h after treatment.Reproductive life table parameters of new emerged aphid surveyed at sub-lethal concentrations(LC20 and LC40) of EO and the biological reproductive table was calculated by Jackknife method.Results: The mortality rate increased significantly with the increasing of EO concentration. The estimated LC50 value was 4.5 μL/L air. Laboratory exposure to sublethal concentrations of EO caused significant decrease in adult female longevity and fertility of surviving aphids and as a result caused significant reduction in the intrinsic rate of natural increase(rmvalue).Conclusion: The results of this study revealed that EO of T. polium could be used as a potential control agent for the aphid.
