Hymoins A–C(1–3),three unusual polycyclic polyprenylated acylphloroglucinols(PPAPs)were isolated from the flowers of Hypericum monogynum.Hymoin A features the first intriguing 6/5/5/5/7 pentacyclic caged PPAP.Hymoin...Hymoins A–C(1–3),three unusual polycyclic polyprenylated acylphloroglucinols(PPAPs)were isolated from the flowers of Hypericum monogynum.Hymoin A features the first intriguing 6/5/5/5/7 pentacyclic caged PPAP.Hymoin B is characterized by an unprecedented rearranged 5/6/8 tricyclic ring system,while hymoin C represents the first rearranged PPAP with a fantastic spirocyclic 5/6/7 ring system.Their structures were established by extensive spectroscopic analysis,X-ray crystallography,and computational methods.The plausible biosynthetic routes for the compounds were also proposed.In oleic acid(OA)-induced HepG2 cells,all compounds exhibited significant lipid-lowering activity at the concentrations of 2–8μmol/L.Further mechanistic study implied that compound 1 exhibited excellent lipid-lowering activity in OA-induced HepG2 cells through inhibiting the proteins of free fatty acids synthesis and improving lipidolysis.展开更多
Hyperforatone A(1),the 1,8-seco rearranged polycyclic polyprenylated acylphloroglucinol,possessed an unusual bicyclo[5.4.0]undecane skeleton bearing a 5/7/6/5 ring system,and two known biosynthetically related precurs...Hyperforatone A(1),the 1,8-seco rearranged polycyclic polyprenylated acylphloroglucinol,possessed an unusual bicyclo[5.4.0]undecane skeleton bearing a 5/7/6/5 ring system,and two known biosynthetically related precursors(2 and 3)were isolated from Hypericum perforatum(St.John's wort).The structure and absolute configuration were unambiguously confirmed by a combination of comprehensive spectroscopic data,computational methods including residual dipolar couplings(RDCs),and X-ray crystallography.Density functional theory(DFT)calculations revealed that the cationic cyclization reaction was key to proposed formation mechanism for hyperforatone A.Furthermore,in vitro and in vivo experiments demonstrated that compound 1 was a potential anti-neuroinfiammatory agent.展开更多
Hepatic ischemia/reperfusion injury(IRI)remains a critical complication contributing to graft dysfunction following liver surgery.As part of an ongoing search for hepatoprotective natural products,five previously unre...Hepatic ischemia/reperfusion injury(IRI)remains a critical complication contributing to graft dysfunction following liver surgery.As part of an ongoing search for hepatoprotective natural products,five previously unreported homoadamantane-type polycyclic polyprenylated acylphloroglucinols(PPAPs),named hyperhomanoons A-E(1-5),and one known analog,hypersampsone O(6),were isolated from Hypericum patulum.Among these,compound 6 demonstrated potent protective effects against CoCl_(2)-induced hypoxic injury in hepatocytes.Furthermore,in a murine model of hepatic IRI induced by vascular occlusion,pretreatment with 6 markedly alleviated liver damage and reduced hepatocyte apoptosis.This study is the first to identify PPAPs as promising scaffolds for the development of therapeutic agents targeting hepatic IRI,underscoring their potential as lead compounds in drug discovery efforts for ischemic liver diseases.展开更多
Hyparillums A(1)and B(2),two previously unidentified polycyclic polyprenylated acylphloroglucinols(PPAPs)with intricate architectures,were isolated from Hypericum patulum Thunb.Hyparillum A was the first PPAP with eig...Hyparillums A(1)and B(2),two previously unidentified polycyclic polyprenylated acylphloroglucinols(PPAPs)with intricate architectures,were isolated from Hypericum patulum Thunb.Hyparillum A was the first PPAP with eight-carbon rings based on an unprecedented 6/6/5/6/6/5/6/4 octocyclic system featuring a rare heptacyclo[10.8.1.11,10.03,8.08,21.012,19.014,17]docosane core.In contrast,hyparillum B featured a novel heptacyclic architecture(6/6/5/6/6/5/5)based on a hexacyclo[9.6.1.11,9.03,7.07,18.011,16]nonadecane motif.Furthermore,hyparillums A and B demonstrated promising inhibitory effects on the proliferation of murine splenocytes stimulated by anti-CD3/anti-CD28 monoclonal antibodies and lipopolysaccharide,exhibiting half-maximal inhibitory concentration(IC50)values ranging from 6.13±0.86 to 12.69±1.31μmol·L−1.展开更多
In addition to six known flavonoids quercitrin, hyperoside, avicularin, rutin, quercetin and kaemferol, a new flavonol glycoside named 6″_O_acetyl quercetin 3_O_β_ D _alloside (1) was isolated from the aerial par...In addition to six known flavonoids quercitrin, hyperoside, avicularin, rutin, quercetin and kaemferol, a new flavonol glycoside named 6″_O_acetyl quercetin 3_O_β_ D _alloside (1) was isolated from the aerial parts of Hypericum perforatum L. The structures were determined on the basis of spectroscopic methods (UV, IR, FAB_MS, 1H_NMR and 13 C NMR). Antifungal assay of all compounds showed that metabolite 1, quercitrin and quercetin were inhibitory to the growth of phytopathogenic fungus Helminthosporium sativum Pamel King et Bakke with minimum inhibitory concentrations (MICs) of 25, 50 and 50 μg/mL, respectively. Moreover, glycoside 1 and quercitrin were also shown to be able to inhibit the growth of Fusarium graminearum Schw. with MIC of 100 μg/mL. The MICs of ketoconazole used as control against the test fungi were 0.5 μg/mL in our assay.展开更多
With the development of the multicellular nodules in the leaves of Hypericum per plastids increased both in number and volume, and some plastids degenerated and were surrounded by dark tubular elements and vesicles. S...With the development of the multicellular nodules in the leaves of Hypericum per plastids increased both in number and volume, and some plastids degenerated and were surrounded by dark tubular elements and vesicles. Some vesicles fused with vacuoles and secreted substances into vacuoles. There are many multivesicles, multimembrane structures and osmiophilic droplets in vacuoles of nodule cells. Meanwhile, dictyosome secreted vesicles into the vacuoles. However, there is a large central vacuole completely filled with secretory materials (hypericin) in matured multicellular nodules. This suggests that the osmiophilic droplets may be a precursor of hypericin originated from the degenerated plastids. There were abundant endoplasmic reticulums and dictyosomes between the plastids and osmiophilic droplets, suggesting that they may be involved in the synthesis and/or transport of the precursor of hypericin.展开更多
Aim Isolation and structural elucidation of the constituents from the aerialpart of Hypericum perforatum L. Methods Column chromatography and TLC were used to isolate chemicalconstituents. Physico-chemical characteriz...Aim Isolation and structural elucidation of the constituents from the aerialpart of Hypericum perforatum L. Methods Column chromatography and TLC were used to isolate chemicalconstituents. Physico-chemical characterization and spectroscopic analysis were employed forstructural identification. Results Three flavonols were isolated and identified. Conclusion Compound1 is a novel natural product and its structure has been characterized to be 3, 5, 7-trihydroxy-3',4'-isopropyldioxy-flavone.展开更多
The present study was conducted to determine the total hypericin contents of Hypericum triquetrifolium Turra.and Hypericum scabrum L.species which are naturally distributed in the flora of Siirt province,Turkey.Hyperi...The present study was conducted to determine the total hypericin contents of Hypericum triquetrifolium Turra.and Hypericum scabrum L.species which are naturally distributed in the flora of Siirt province,Turkey.Hypericin contents of Hypericum species grown in different geographical aspects(North,South,East,and West),and it was measured at different harvest times(full bloom-ing and post blooming period).In the current study,it has been determined that total hypericin content varies considerably according to aspects,plant developmental stages(ontogenetic variance),and species.According to species x aspect interaction,the highest total hypericin content was recorded from the west aspect(3.13 mg/g)in Hypericum triquetrifolium,while,the lowest hypericin content was also obtained from the west aspect(1.22 mg/g)in Hypericum scabrum.When the highest total hypericin content was analyzed according to aspect x species x harvest time interaction,the highest total hypericin content was produced from Hypericum triquetrifolium at the harvest of west aspect with 5.28 mg/g,while the minimum amount of hypericin was obtained from the same aspect in Hypericum scabrum with 0.50 mg/g.In species x harvest time interaction,the highest total hypericin content was obtained from the full bloom(3.10 mg/g)harvest in Hypericum triquetrifolium,while the lowest hypericin was obtained from the full bloom(1.26 mg/g)harvest in Hypericum scabrum.The data suggest that the aver-age total hypericin content was 2.26 mg/g in Hypericum triquetrifolium and 1.28 mg/g in Hypericum scabrum.展开更多
Objective:To evaluate the antihyperglycemic activity of ethyl acetate extract of Hypericum perforatum(H.perforatum)in streptozotocin(STZ)-induced diabetic rats.Methods:Acute toxicity and oral glucose tolerance lest we...Objective:To evaluate the antihyperglycemic activity of ethyl acetate extract of Hypericum perforatum(H.perforatum)in streptozotocin(STZ)-induced diabetic rats.Methods:Acute toxicity and oral glucose tolerance lest were performed in normal rats.Male albino rats were rendered diabetic by ST/(40 mg/kg,intraperitoneally).H.perforatum ethyl acetate extract was orally administered to diabetic rats at SO,100 and 200 mg/kg doses for 15 days to determine the antihyperglycemic activity.Biochemical parameters were determined at the end of the treatment.Results:H.perforatum ethyl acetate extract showed dose dependant fall in fasting blood glucose(FBG).After 30 min of extract administration,FBG was reduced significantly when compared with normal rats.H.perforatum ethyl acetate extract produced significant reduction in plasma glucose level,serum total cholesterol,triglycerides,glucose-6-phosphatase levels.Tissue glycogen content,HDL-cholesterol,glucose-6-phosphate dehydrogenase were significantly increased compared with diabetic control.No death or lethal effect was observed in the toxic study.Conclusions:The results demonstrate that H.perforatum ethyl acetate extract possesses potent antihyperglycemic activity in STZ induced diabetic rats.展开更多
To study the influence of Hypericum perforatum extract （HPE） on piglets infected with porcine respiratory and reproductive syndrome virus （PRRSV）, enzyme-labeled immunosorbent assay （ELISA） and cytopathic effect...To study the influence of Hypericum perforatum extract （HPE） on piglets infected with porcine respiratory and reproductive syndrome virus （PRRSV）, enzyme-labeled immunosorbent assay （ELISA） and cytopathic effect （CPE） were used to determine in vitro whether HPE could induce swine pulmonary alveolar macrophages （PAMs） to secrete IFN-γ, and whether PRRSV titers in PAMs were affected by the levels of HPE-induced IFN-γ. HPE （200 mg·kg-1） was administrated by oral gavage to piglets infected with the PRRSV in vivo to observe whether HPE affected the viremia, lung viral titers, and weight gain of piglets infected with PRRSV. The results showed that HPE was capable of inducing PAMs to produce IFN-γ in a dose dependent manner and HPE pretreatment was capable of significantly reducing PRRSV viral titers in PAMs （P〈 0.01）. Administration of HPE to the PRRSV-infected animals significantly （P〈 0.05） reduced viremia over time as compared with the PRRSV-infected animals. But there was not significant decrease in lung viral titers at day 21 post-infection between the HPE- treated animals and the PRRSV-infected control piglets. There were no significant differences in weight gain over time among the HPE-treatment animals, the normal control, and the HPE control animals. The PRRSV-infected animals caused significant （P〈 0.01） growth retardation as compared with the HPE controls and the normal piglets. It suggested that HPE might be an effective novel therapeutic approach to diminish the PRRSV-induced disease in swine.展开更多
There are about 400 species in Hypericurn world-wide.and 55 species and 8 subspecies have been reportedin China[1],A medicinal constituent,the hypericin,wasfound in this genus[2.3].Hypericin can be used as an an-tidep...There are about 400 species in Hypericurn world-wide.and 55 species and 8 subspecies have been reportedin China[1],A medicinal constituent,the hypericin,wasfound in this genus[2.3].Hypericin can be used as an an-tidepressant drug-4].In the last decade,hypericin wasalso used in the treatnent of AIDS.[6.7],because of its im-rmunotropic activity and marked anti-RNA virus and anti-DNA vinus effects[5].Liu and Hu[8],Lii et al Mi haveexamined the histochemistry.types and distributionaldensity of the secretory structures in the gemus,but phy-tochemical evidence is still lacking.展开更多
The infrared spectroscopic study of leaves of nine sections,43 species,one subspecies and one variety in Hypericum L.and two species in Triadenum Raf.were conducted directly and rapidly with FTIR and OMNl-sampler acce...The infrared spectroscopic study of leaves of nine sections,43 species,one subspecies and one variety in Hypericum L.and two species in Triadenum Raf.were conducted directly and rapidly with FTIR and OMNl-sampler accessory.The results showed that the infrared spectra of Hypericum and Triadenum were fingerprint-like patterns which were highly typical for different taxa.Significant differences in the infrared spectra were found between these two genera and among the nine sections of Hypericum.And certain differences exist in the spectra among species in the same section of Hypericum or in the Triadenum.Furthermore,no significant difference was found in the infrared spectral patterns in the leaves at various developmental stages and in leaves of the same species collected from different géographic regions,although occasionally geographic difference did exist in the same species.The results indicated that the infrared spectra of leaves are of taxonomic value at the level of species and sections in these two genera,and this technique can be widely used for identification and classification of other taxa when standard spectraare available.展开更多
Three new homo-adamantanyl type natural products were derived from polyprenylated polycyclic acylphloroglucinol.Hypercohones A-C(1-3),along with five other known hypercohones(4-8),were isolated from the aerial parts o...Three new homo-adamantanyl type natural products were derived from polyprenylated polycyclic acylphloroglucinol.Hypercohones A-C(1-3),along with five other known hypercohones(4-8),were isolated from the aerial parts of Hypericum cohaerens.The structures of 1-3 were elucidated on the basis of comprehensive spectroscopic analysis.The inhibitory activities of these isolates against five human cancer cell lines in vitro were tested.展开更多
Two new type B polycyclic polyprenylated acylphloroglucinols(PPAPs)(1 and 2)and a known biogenetic precursor hyperbeanol Q(3)were isolated from the root extract of Hypericum beanii,a medicinal plant widespread in sout...Two new type B polycyclic polyprenylated acylphloroglucinols(PPAPs)(1 and 2)and a known biogenetic precursor hyperbeanol Q(3)were isolated from the root extract of Hypericum beanii,a medicinal plant widespread in southwest China.Their chemical structures were elucidated by 1 D/2 D NMR and HRESIMS data analysis,and absolute configurations were determined through detailed electric circular dichroism(ECD)analysis including ECD exciton chirality,Mo2(OAc)4-induced ECD,and ECD comparison.Of these compounds,hyperbeone A(1)is a typical[3.3.1]-type B PPAP with an unusual C-1 geranyl side chain,and hyperberin C(2)possesses a rare bicyclo[5.3.1]hendecane core.Taking compound 3 as a starting point,a plausible biosynthetic pathway to the bicyclic type B frameworks of 1 and 2 was proposed.展开更多
Hyperterpenoid A(1)and B(2),two pairs of enantiomers,with an unprecedented 6/6/4/6/6 polycyclic skeleton,along with one known compoud hypermonone A(3)were isolated from Hypericum beanii.The racemate(±)-1 and(...Hyperterpenoid A(1)and B(2),two pairs of enantiomers,with an unprecedented 6/6/4/6/6 polycyclic skeleton,along with one known compoud hypermonone A(3)were isolated from Hypericum beanii.The racemate(±)-1 and(±)-2 were successfully separated into the two optically pure enantiomers(ee>99%)using a preparative HPLC system.Their absolute configurations were elucidated by extensive spectroscopic analyses and single-crystal X-ray diffraction method.The related plausible biogenetic pathways were pre sented.Compound 1-3 showed significant neuroprotective activity and potential antiinflammatory activity.The result that(+)-2 and(-)-2 presented different anti-inflammatory properties,may lead us to new discovery of structure activity relationship between racemates,enantiomers,and diastereomers,as well as further research regarding the binding of drugs to target proteins.展开更多
A new xanthone, 1,2-dihydro-3,6,8-trihydroxy-1,1-bis (3-methylbut -2-enyl)-5-(1, 1-dimethylprop-2-enyl)xanthen-2,9-dione (1), has been isolated from the aerial part of Hypericum erectum.
Two novel seco-polycyclic polyprenylated acylphloroglucinols(PPAPs),hyperbenzones A(1)and B(2),were isolated from the roots of Hypericum beanii,together with one known biosynthetic congener 3.Compound 1 incorporates a...Two novel seco-polycyclic polyprenylated acylphloroglucinols(PPAPs),hyperbenzones A(1)and B(2),were isolated from the roots of Hypericum beanii,together with one known biosynthetic congener 3.Compound 1 incorporates a 6/5/5 ring system with an unprecedented spiro[bicyclo[3.3.0]octane-3,1'-cyclohexane]-2,2'-dione motif.The structures of 1 and 2 were determined by a combination of high resolution electrospray ionization mass spectroscopy(HRESIMS),nuclear magnetic resonance(NMR)spectroscopic analyses,gage-independent atomic orbital(GIAO)NMR chemical shift calculation with DP4+analyses,electronic circular dichroism(ECD)calculation,and X-ray diffraction analysis.A 1,2-seco retroClaisen rearrangement from a bicyclo[3.3.1]nonane PPAP precursor and following chemodivergent radical cascade cyclizations are proposed as the key steps in the biosynthetic pathway to yield compounds 1 and2.Biological investigations indicated that compounds 1 and 3 could decrease intracellular lipid accumulation in a palmitic acid-induced nonalcoholic steatohepatitis(NASH)cell model.展开更多
Five new polycyclic polyprenylated acylphloroglucinols(1-5),ascyrones A-E,and four known compounds(6-9)were isolated from the aerial parts of Hypericum ascyron.All of the isolates containing a bicyclo[3.3.1]nonane-2,4...Five new polycyclic polyprenylated acylphloroglucinols(1-5),ascyrones A-E,and four known compounds(6-9)were isolated from the aerial parts of Hypericum ascyron.All of the isolates containing a bicyclo[3.3.1]nonane-2,4,9-trione core and a benzoyl group,belonged to type B bicyclic polyprenylated acylphloroglucinols(BPAPs).Their structures and absolute configurations were established based on spectroscopic analyses and calculated electronic circular dichroism(ECD)data.The anti-inflammatory,neuroprotective and cytotoxicity activities of compounds 1-4 and 6-9 were evaluated.Compound 6 exhibited obvious anti-inflammatory activity in lipopolysaccharide(LPS)-induced RAW264.7 cells.Compounds 1 and 9 exhibited slight cytotoxicity against Hep3B cells.Meanwhile,compound 1 showed mild neuroprotective activity against corticosterone(CORT)-induced PC 12 cell damage at 10 μmol-L^(-1).展开更多
基金financially supported by the National Natural Science Foundation of China(Nos.32270413,82060631,82160808,and 82360035)the Science and Technology Department of Guizhou Province(Nos.QKHJC 2020–1Z076,QKHJC-ZK[2023]YB156,QKHJC-ZK[2021]YB569,and QKHPTRC[2020]5008)+4 种基金Excellent Young Talents Plan of Guizhou Medical University(2023,No.106)the 13thbatch of outstanding young scientific and technological talents in Guizhou Province(No.QKHPTRC[2021]5633)Guizhou Science and Technology Innovation Talent Team(No.QKHPTRC–CXTD[2022]007)High-level Innovative Talents in Guizhou Province(Thousand Levels of Talent for Chunmao Yuan in 2018)the project of State Key Laboratory of Functions and Applications of Medicinal Plants,Guizhou Medical University(Nos.FAMP202102K and QJJ[2023]113)。
文摘Hymoins A–C(1–3),three unusual polycyclic polyprenylated acylphloroglucinols(PPAPs)were isolated from the flowers of Hypericum monogynum.Hymoin A features the first intriguing 6/5/5/5/7 pentacyclic caged PPAP.Hymoin B is characterized by an unprecedented rearranged 5/6/8 tricyclic ring system,while hymoin C represents the first rearranged PPAP with a fantastic spirocyclic 5/6/7 ring system.Their structures were established by extensive spectroscopic analysis,X-ray crystallography,and computational methods.The plausible biosynthetic routes for the compounds were also proposed.In oleic acid(OA)-induced HepG2 cells,all compounds exhibited significant lipid-lowering activity at the concentrations of 2–8μmol/L.Further mechanistic study implied that compound 1 exhibited excellent lipid-lowering activity in OA-induced HepG2 cells through inhibiting the proteins of free fatty acids synthesis and improving lipidolysis.
基金financially supported by the National Natural Science Foundation of China(Nos.22077102,32201249)the Science and Technology Program of Gansu Province(No.22YF7GA046)。
文摘Hyperforatone A(1),the 1,8-seco rearranged polycyclic polyprenylated acylphloroglucinol,possessed an unusual bicyclo[5.4.0]undecane skeleton bearing a 5/7/6/5 ring system,and two known biosynthetically related precursors(2 and 3)were isolated from Hypericum perforatum(St.John's wort).The structure and absolute configuration were unambiguously confirmed by a combination of comprehensive spectroscopic data,computational methods including residual dipolar couplings(RDCs),and X-ray crystallography.Density functional theory(DFT)calculations revealed that the cationic cyclization reaction was key to proposed formation mechanism for hyperforatone A.Furthermore,in vitro and in vivo experiments demonstrated that compound 1 was a potential anti-neuroinfiammatory agent.
基金supported by the National Natural Science Foundation for Distinguished Young Scholars(No.81725021)the National Natural Science Foundation of China(Nos.82003633 and 82173705)。
文摘Hepatic ischemia/reperfusion injury(IRI)remains a critical complication contributing to graft dysfunction following liver surgery.As part of an ongoing search for hepatoprotective natural products,five previously unreported homoadamantane-type polycyclic polyprenylated acylphloroglucinols(PPAPs),named hyperhomanoons A-E(1-5),and one known analog,hypersampsone O(6),were isolated from Hypericum patulum.Among these,compound 6 demonstrated potent protective effects against CoCl_(2)-induced hypoxic injury in hepatocytes.Furthermore,in a murine model of hepatic IRI induced by vascular occlusion,pretreatment with 6 markedly alleviated liver damage and reduced hepatocyte apoptosis.This study is the first to identify PPAPs as promising scaffolds for the development of therapeutic agents targeting hepatic IRI,underscoring their potential as lead compounds in drug discovery efforts for ischemic liver diseases.
基金supported by the Program for Changjiang Scholars of Ministry of Education of the People’s Republic of China(No.T2016088)the National Natural Science Foundation for Distinguished Young Scholars(No.81725021)+5 种基金the National Science and Technology Project of China(No.2018ZX09201001-001-003)the National Natural Science Foundation of China(Nos.82003633,32100321,and 32300335)the Research and Development Program of Hubei Province(No.2020BCA058)the Open Foundation of Hubei Key Laboratory of Wudang Local Chinese Medicine Research(No.WDCM2022003)the National Natural Science Foundation of Hubei Province(No.2023AFB530)the Knowledge Innovation Project of Wuhan Science and Technology Bureau(No.2023020201020534).
文摘Hyparillums A(1)and B(2),two previously unidentified polycyclic polyprenylated acylphloroglucinols(PPAPs)with intricate architectures,were isolated from Hypericum patulum Thunb.Hyparillum A was the first PPAP with eight-carbon rings based on an unprecedented 6/6/5/6/6/5/6/4 octocyclic system featuring a rare heptacyclo[10.8.1.11,10.03,8.08,21.012,19.014,17]docosane core.In contrast,hyparillum B featured a novel heptacyclic architecture(6/6/5/6/6/5/5)based on a hexacyclo[9.6.1.11,9.03,7.07,18.011,16]nonadecane motif.Furthermore,hyparillums A and B demonstrated promising inhibitory effects on the proliferation of murine splenocytes stimulated by anti-CD3/anti-CD28 monoclonal antibodies and lipopolysaccharide,exhibiting half-maximal inhibitory concentration(IC50)values ranging from 6.13±0.86 to 12.69±1.31μmol·L−1.
文摘In addition to six known flavonoids quercitrin, hyperoside, avicularin, rutin, quercetin and kaemferol, a new flavonol glycoside named 6″_O_acetyl quercetin 3_O_β_ D _alloside (1) was isolated from the aerial parts of Hypericum perforatum L. The structures were determined on the basis of spectroscopic methods (UV, IR, FAB_MS, 1H_NMR and 13 C NMR). Antifungal assay of all compounds showed that metabolite 1, quercitrin and quercetin were inhibitory to the growth of phytopathogenic fungus Helminthosporium sativum Pamel King et Bakke with minimum inhibitory concentrations (MICs) of 25, 50 and 50 μg/mL, respectively. Moreover, glycoside 1 and quercitrin were also shown to be able to inhibit the growth of Fusarium graminearum Schw. with MIC of 100 μg/mL. The MICs of ketoconazole used as control against the test fungi were 0.5 μg/mL in our assay.
文摘With the development of the multicellular nodules in the leaves of Hypericum per plastids increased both in number and volume, and some plastids degenerated and were surrounded by dark tubular elements and vesicles. Some vesicles fused with vacuoles and secreted substances into vacuoles. There are many multivesicles, multimembrane structures and osmiophilic droplets in vacuoles of nodule cells. Meanwhile, dictyosome secreted vesicles into the vacuoles. However, there is a large central vacuole completely filled with secretory materials (hypericin) in matured multicellular nodules. This suggests that the osmiophilic droplets may be a precursor of hypericin originated from the degenerated plastids. There were abundant endoplasmic reticulums and dictyosomes between the plastids and osmiophilic droplets, suggesting that they may be involved in the synthesis and/or transport of the precursor of hypericin.
文摘Aim Isolation and structural elucidation of the constituents from the aerialpart of Hypericum perforatum L. Methods Column chromatography and TLC were used to isolate chemicalconstituents. Physico-chemical characterization and spectroscopic analysis were employed forstructural identification. Results Three flavonols were isolated and identified. Conclusion Compound1 is a novel natural product and its structure has been characterized to be 3, 5, 7-trihydroxy-3',4'-isopropyldioxy-flavone.
基金This publication was supported by Award Number(2016-SİUFEB-23)from the Research Foundation of Siirt University,Turkey.
文摘The present study was conducted to determine the total hypericin contents of Hypericum triquetrifolium Turra.and Hypericum scabrum L.species which are naturally distributed in the flora of Siirt province,Turkey.Hypericin contents of Hypericum species grown in different geographical aspects(North,South,East,and West),and it was measured at different harvest times(full bloom-ing and post blooming period).In the current study,it has been determined that total hypericin content varies considerably according to aspects,plant developmental stages(ontogenetic variance),and species.According to species x aspect interaction,the highest total hypericin content was recorded from the west aspect(3.13 mg/g)in Hypericum triquetrifolium,while,the lowest hypericin content was also obtained from the west aspect(1.22 mg/g)in Hypericum scabrum.When the highest total hypericin content was analyzed according to aspect x species x harvest time interaction,the highest total hypericin content was produced from Hypericum triquetrifolium at the harvest of west aspect with 5.28 mg/g,while the minimum amount of hypericin was obtained from the same aspect in Hypericum scabrum with 0.50 mg/g.In species x harvest time interaction,the highest total hypericin content was obtained from the full bloom(3.10 mg/g)harvest in Hypericum triquetrifolium,while the lowest hypericin was obtained from the full bloom(1.26 mg/g)harvest in Hypericum scabrum.The data suggest that the aver-age total hypericin content was 2.26 mg/g in Hypericum triquetrifolium and 1.28 mg/g in Hypericum scabrum.
文摘Objective:To evaluate the antihyperglycemic activity of ethyl acetate extract of Hypericum perforatum(H.perforatum)in streptozotocin(STZ)-induced diabetic rats.Methods:Acute toxicity and oral glucose tolerance lest were performed in normal rats.Male albino rats were rendered diabetic by ST/(40 mg/kg,intraperitoneally).H.perforatum ethyl acetate extract was orally administered to diabetic rats at SO,100 and 200 mg/kg doses for 15 days to determine the antihyperglycemic activity.Biochemical parameters were determined at the end of the treatment.Results:H.perforatum ethyl acetate extract showed dose dependant fall in fasting blood glucose(FBG).After 30 min of extract administration,FBG was reduced significantly when compared with normal rats.H.perforatum ethyl acetate extract produced significant reduction in plasma glucose level,serum total cholesterol,triglycerides,glucose-6-phosphatase levels.Tissue glycogen content,HDL-cholesterol,glucose-6-phosphate dehydrogenase were significantly increased compared with diabetic control.No death or lethal effect was observed in the toxic study.Conclusions:The results demonstrate that H.perforatum ethyl acetate extract possesses potent antihyperglycemic activity in STZ induced diabetic rats.
基金supported by One Hundred Person Project of the Chinese Academy of Sciences (Renjiaozi[2008] 287)the Special Fund to Aid Basic Scientific Research of State Level Research Institutes for Public Welfare, China (BRF070402)
文摘To study the influence of Hypericum perforatum extract （HPE） on piglets infected with porcine respiratory and reproductive syndrome virus （PRRSV）, enzyme-labeled immunosorbent assay （ELISA） and cytopathic effect （CPE） were used to determine in vitro whether HPE could induce swine pulmonary alveolar macrophages （PAMs） to secrete IFN-γ, and whether PRRSV titers in PAMs were affected by the levels of HPE-induced IFN-γ. HPE （200 mg·kg-1） was administrated by oral gavage to piglets infected with the PRRSV in vivo to observe whether HPE affected the viremia, lung viral titers, and weight gain of piglets infected with PRRSV. The results showed that HPE was capable of inducing PAMs to produce IFN-γ in a dose dependent manner and HPE pretreatment was capable of significantly reducing PRRSV viral titers in PAMs （P〈 0.01）. Administration of HPE to the PRRSV-infected animals significantly （P〈 0.05） reduced viremia over time as compared with the PRRSV-infected animals. But there was not significant decrease in lung viral titers at day 21 post-infection between the HPE- treated animals and the PRRSV-infected control piglets. There were no significant differences in weight gain over time among the HPE-treatment animals, the normal control, and the HPE control animals. The PRRSV-infected animals caused significant （P〈 0.01） growth retardation as compared with the HPE controls and the normal piglets. It suggested that HPE might be an effective novel therapeutic approach to diminish the PRRSV-induced disease in swine.
基金Supported by the National Natural Science Foundation of China(30070045).
文摘There are about 400 species in Hypericurn world-wide.and 55 species and 8 subspecies have been reportedin China[1],A medicinal constituent,the hypericin,wasfound in this genus[2.3].Hypericin can be used as an an-tidepressant drug-4].In the last decade,hypericin wasalso used in the treatnent of AIDS.[6.7],because of its im-rmunotropic activity and marked anti-RNA virus and anti-DNA vinus effects[5].Liu and Hu[8],Lii et al Mi haveexamined the histochemistry.types and distributionaldensity of the secretory structures in the gemus,but phy-tochemical evidence is still lacking.
文摘The infrared spectroscopic study of leaves of nine sections,43 species,one subspecies and one variety in Hypericum L.and two species in Triadenum Raf.were conducted directly and rapidly with FTIR and OMNl-sampler accessory.The results showed that the infrared spectra of Hypericum and Triadenum were fingerprint-like patterns which were highly typical for different taxa.Significant differences in the infrared spectra were found between these two genera and among the nine sections of Hypericum.And certain differences exist in the spectra among species in the same section of Hypericum or in the Triadenum.Furthermore,no significant difference was found in the infrared spectral patterns in the leaves at various developmental stages and in leaves of the same species collected from different géographic regions,although occasionally geographic difference did exist in the same species.The results indicated that the infrared spectra of leaves are of taxonomic value at the level of species and sections in these two genera,and this technique can be widely used for identification and classification of other taxa when standard spectraare available.
基金The work was financially supported by the foundations from NSFC(20972167)the Young Academic Leader Raising Foundation of Yunnan Province(No.2009CI073)the foundation from CAS to Dr Gang Xu.
文摘Three new homo-adamantanyl type natural products were derived from polyprenylated polycyclic acylphloroglucinol.Hypercohones A-C(1-3),along with five other known hypercohones(4-8),were isolated from the aerial parts of Hypericum cohaerens.The structures of 1-3 were elucidated on the basis of comprehensive spectroscopic analysis.The inhibitory activities of these isolates against five human cancer cell lines in vitro were tested.
基金the National Natural Science Foundation of China(No.31900287)the Drug Innovation Major Project(2018ZX09711-001-007)the China Postdoctoral Science Foundation(2017M621889)。
文摘Two new type B polycyclic polyprenylated acylphloroglucinols(PPAPs)(1 and 2)and a known biogenetic precursor hyperbeanol Q(3)were isolated from the root extract of Hypericum beanii,a medicinal plant widespread in southwest China.Their chemical structures were elucidated by 1 D/2 D NMR and HRESIMS data analysis,and absolute configurations were determined through detailed electric circular dichroism(ECD)analysis including ECD exciton chirality,Mo2(OAc)4-induced ECD,and ECD comparison.Of these compounds,hyperbeone A(1)is a typical[3.3.1]-type B PPAP with an unusual C-1 geranyl side chain,and hyperberin C(2)possesses a rare bicyclo[5.3.1]hendecane core.Taking compound 3 as a starting point,a plausible biosynthetic pathway to the bicyclic type B frameworks of 1 and 2 was proposed.
基金financially supported by Projects of International Cooperation and Exchanges NSFC(NSFC-VR,No.81361138020)National Science and Technology Major Projects for"Major New Drugs Innovation and Development",Research and Development of New Drug Varieties from Natural Product Sources and Their Key Innovative Technological Systems(Nos.2018ZX09711001-001-001 and 2018ZX09711001-001-003)the CAMS Innovation Fund for Medical Sciences(CIFMS),the CAMS Initiative for Innovative Medicine(CAMS-I2M,No.2016-I2M-1-010)。
文摘Hyperterpenoid A(1)and B(2),two pairs of enantiomers,with an unprecedented 6/6/4/6/6 polycyclic skeleton,along with one known compoud hypermonone A(3)were isolated from Hypericum beanii.The racemate(±)-1 and(±)-2 were successfully separated into the two optically pure enantiomers(ee>99%)using a preparative HPLC system.Their absolute configurations were elucidated by extensive spectroscopic analyses and single-crystal X-ray diffraction method.The related plausible biogenetic pathways were pre sented.Compound 1-3 showed significant neuroprotective activity and potential antiinflammatory activity.The result that(+)-2 and(-)-2 presented different anti-inflammatory properties,may lead us to new discovery of structure activity relationship between racemates,enantiomers,and diastereomers,as well as further research regarding the binding of drugs to target proteins.
文摘A new xanthone, 1,2-dihydro-3,6,8-trihydroxy-1,1-bis (3-methylbut -2-enyl)-5-(1, 1-dimethylprop-2-enyl)xanthen-2,9-dione (1), has been isolated from the aerial part of Hypericum erectum.
基金supported by the National Natural Science Foundation of China(Nos.31900287 and 81773886)the 111 Project from Ministry of Education of China and the State Administration of Foreign Export Affairs of China(No.B18056)Special fund from the Central Committee for guiding local scientific and technological development of Shenzhen(No.2021Szvup161)。
文摘Two novel seco-polycyclic polyprenylated acylphloroglucinols(PPAPs),hyperbenzones A(1)and B(2),were isolated from the roots of Hypericum beanii,together with one known biosynthetic congener 3.Compound 1 incorporates a 6/5/5 ring system with an unprecedented spiro[bicyclo[3.3.0]octane-3,1'-cyclohexane]-2,2'-dione motif.The structures of 1 and 2 were determined by a combination of high resolution electrospray ionization mass spectroscopy(HRESIMS),nuclear magnetic resonance(NMR)spectroscopic analyses,gage-independent atomic orbital(GIAO)NMR chemical shift calculation with DP4+analyses,electronic circular dichroism(ECD)calculation,and X-ray diffraction analysis.A 1,2-seco retroClaisen rearrangement from a bicyclo[3.3.1]nonane PPAP precursor and following chemodivergent radical cascade cyclizations are proposed as the key steps in the biosynthetic pathway to yield compounds 1 and2.Biological investigations indicated that compounds 1 and 3 could decrease intracellular lipid accumulation in a palmitic acid-induced nonalcoholic steatohepatitis(NASH)cell model.
基金This work was supported by the National Natural Science Foundation of China(No.31800279).
文摘Five new polycyclic polyprenylated acylphloroglucinols(1-5),ascyrones A-E,and four known compounds(6-9)were isolated from the aerial parts of Hypericum ascyron.All of the isolates containing a bicyclo[3.3.1]nonane-2,4,9-trione core and a benzoyl group,belonged to type B bicyclic polyprenylated acylphloroglucinols(BPAPs).Their structures and absolute configurations were established based on spectroscopic analyses and calculated electronic circular dichroism(ECD)data.The anti-inflammatory,neuroprotective and cytotoxicity activities of compounds 1-4 and 6-9 were evaluated.Compound 6 exhibited obvious anti-inflammatory activity in lipopolysaccharide(LPS)-induced RAW264.7 cells.Compounds 1 and 9 exhibited slight cytotoxicity against Hep3B cells.Meanwhile,compound 1 showed mild neuroprotective activity against corticosterone(CORT)-induced PC 12 cell damage at 10 μmol-L^(-1).
