A detailed investigation was carried out to understand how the variations in configurations of the spiroannulated 6-6-6-5-5 pentacyclic diastereoisomers,the key intermediates for the synthesis of two C30 terpene quino...A detailed investigation was carried out to understand how the variations in configurations of the spiroannulated 6-6-6-5-5 pentacyclic diastereoisomers,the key intermediates for the synthesis of two C30 terpene quinonemethides and their stereoisomers,impact the reactivity of cyclopropanation.The configurations at C9,C8,and C14 for all four pentacyclic diastereoisomers involved in the diastereoisomeric mixture were determined through a combination of suitable chemical derivatization and multiple NMR spectroscopic analyses.Based on the defined configuration,the 3D structures of these diastereoisomers were optimized by density functional theory(DFT)calculation.These investigations provide reasonable supports,mainly from the steric considerations,for understanding why different diastereoisomers exhibit markedly different reactivity,as well as regio-and stereo-selectivity for cyclopropanation.In addition,the mechanism for the construction of the spiroannulated 6-6-6-5-5 pentacyclic scaffold via intramolecular Michael/aldol cascade was also investigated by deuterium labeling experiments.展开更多
Phytochemical study of the n-BuOH extract of Ilex asprella resulted in the discovery of ten new pentacyclic triterpenoid glycosides,comprising nine ursane-type glycosides(1-9)and one oleanane-type glycoside(10),along ...Phytochemical study of the n-BuOH extract of Ilex asprella resulted in the discovery of ten new pentacyclic triterpenoid glycosides,comprising nine ursane-type glycosides(1-9)and one oleanane-type glycoside(10),along with seven known compounds(11-17).Compound 1 is the first reported 19,22-epoxy ursane triterpenoid glycoside,whereas 4 and 5 are rare examples of ursane triterpenoid glycosides containing a 28,19-lactone group.The structural characterization of these compounds was achieved using spectroscopic and chemical techniques,as well as single-crystal X-ray analysis.Compounds 7,12,15,and 17 exhibited moderate cytotoxic activities against H1975 and HCC827 cancer cells.展开更多
Two new pentacyclic triterpene acids, 1a, 3b-dihydroxyl-olean-12-en-28-oic acid and 1a, 2a, 3b-trihydroxyl-olean-12-en-28-oic acid, were isolated from the arial parts of Sabia parviflora.
: Four typical distribution patterns of pentacyclic triterpenoid hydrocarbons (types A-D) are distinguished in the low-mature source rocks from eastern China. Type A has a relatively high content of pentacyclic triter...: Four typical distribution patterns of pentacyclic triterpenoid hydrocarbons (types A-D) are distinguished in the low-mature source rocks from eastern China. Type A has a relatively high content of pentacyclic triterpenes. It exists in immature sediments and the distribution and abundance of triterpenes vary with the maturity of the sediments. An unknown C30 triterpene (UCT2) has also been detected in very shallow sediments. This compound is very unstable and disappears rapidly with the increase of depth. Type B is characterized by a relatively high amount of 17α(H), 21β(H)-30-homohopane. This kind of distribution pattern is common in coals and terrestrial sediments of low maturity. Type C has a relatively high content of diahopane and neohopane series. The analysis shows that this distribution pattern may have an indirect relationship with the input of higher plants despite its microbial source. There are C30—unconfirmed triterpane (UCT2) and a relatively high content of C35 hopane in type D. The distribution patterns of pentacyclic triterpenoids are varied under influences of biological sources, diagentic and sedimentary environments, thermal maturity etc. Therefore, they can provide useful information about the source rocks. Based on geochemical characteristics of the source rocks, the authors postulated that the type B and type C patterns are mainly related to suboxic-anoxic environments. Type D indicates the reducing to anoxic environment, in which C30-UCT3 may be related to some specific biological source in saline environments. The precursors and thermal evolution of some triterpenoid hydrocarbons are also discussed herein.展开更多
The title compound 17（S）-methyl-13β-hydroxyl-14（R）,20（S）-epoxy-pregn-4-en-3-one was synthesized by an improved tandem reaction, and its structure was determined by IR, NMR, HR MS and X-ray single-crystal diffra...The title compound 17（S）-methyl-13β-hydroxyl-14（R）,20（S）-epoxy-pregn-4-en-3-one was synthesized by an improved tandem reaction, and its structure was determined by IR, NMR, HR MS and X-ray single-crystal diffraction. The crystal belongs to orthorhombic, space group P212121 with a = 10.55248（15）, b = 12.14700（16）, c = 14.56841（18） ？, V = 1867.39（4） ？3, Z = 4, Dc= 1.175 g/cm3, μ= 0.604 mm-1, F（000） = 720, the final R = 0.0400 and w R = 0.1072 for 3610 observed reflections with I 〉 2σ（I）.展开更多
The aim of the current work is to synthesize the new heterocyclic pentacyclic condensed systems that combine benzothiophen and benzimidazole/triazole into one molecule. The dibenzothiophene was taken as an initial com...The aim of the current work is to synthesize the new heterocyclic pentacyclic condensed systems that combine benzothiophen and benzimidazole/triazole into one molecule. The dibenzothiophene was taken as an initial compound and by consistent “extension” was annihilated the imidazole and triazole nucleuses. As a result two new pentacyclic systems were produced: 3H-, 7H-diimidazole[4,5-b][5,4-g] dibenzothiophene-5,5-dioxide and 3H-, 7H-ditriazole[4,5-b][5,4-g] dibenzothiophene-5,5-dioxide with the promising antimi-crobial activity. Their spectral characteristics were studied.展开更多
The acetyl ester plays an important role for protection of the hydroxyl groups in carbohydrates synthesis.In the present study,we described an efficient deprotection of acetyl group of pentacyclic triterpenoid by usin...The acetyl ester plays an important role for protection of the hydroxyl groups in carbohydrates synthesis.In the present study,we described an efficient deprotection of acetyl group of pentacyclic triterpenoid by using methanolic ammonia in THF solution.Good selectivity for cleaving gal-C2-OAc group of 3β-hydroxy-olean-12-en-28-oic acid 28-N-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside(3) was achieved in the presence of methanolic ammonia within 4 h at low temperature(-60℃) in a yield of 56%.The reaction disclosed here provides a new method for the synthesis of C2 selective modified carbohydrates,which is more useful than conventional synthesis procedure that usually requires many steps including temporary regioselective protection and deprotection.When the reaction temperature was increased from -60℃ to room temperature,the cleavage of the other three acetyl groups of galactose in an order of C4-OAc>C3-OAc>C6-OAc was observed.Based on this study,a plausible route for the deacetylation reaction has been proposed.展开更多
Abundant terrigenous triterpenoid ketones and a series of hopanoid ketones were detected in a peat sample from the recent Gannan Marsh. The identifications of pen-tacyclic triterpenoid ketones are discussed in detail....Abundant terrigenous triterpenoid ketones and a series of hopanoid ketones were detected in a peat sample from the recent Gannan Marsh. The identifications of pen-tacyclic triterpenoid ketones are discussed in detail. Based on the compositional features of pentacyclic triterpenoid ketones in the sample, it is proposed that terrigenous triterpenoid kentones originate directly from organisms or are diagenetic oxidation products of their alcohols, and hopanoid ketones are formed from hopanoids (e.g. hopanoid alcohols and hopenes) by chemical and biochemical processes. These data provide evidence for the applied studies of pentacyclic triterpenoid ketones as biomarker compounds.展开更多
A series of triterpene dimers bearing different scaffold were designed and synthesized via CuAAC reaction. Their anti-HCV entry activities were evaluated by HCVpp and VSVpp entry assays. It was found that echinocystic...A series of triterpene dimers bearing different scaffold were designed and synthesized via CuAAC reaction. Their anti-HCV entry activities were evaluated by HCVpp and VSVpp entry assays. It was found that echinocystic acid （EA） and its dimer were still necessary for maintaining anti-HCV entry activity, and replacement of EA by other triterpenes might significantly decrease its anti-viral activities. Using a linker bearing a piperazine group, compound 14 dramatically increased its potency with IC50 at 2.87 nmol/L. In addition, the undesired hemolytic effect of all these compounds was removed.展开更多
Botanical pentacyclic triterpenes possessed a broad range of pharmacological activities such as antioxidant,anti-tumor,anti-microbial and anti-inflammatory activities.It is believed that the mechanisms involved in the...Botanical pentacyclic triterpenes possessed a broad range of pharmacological activities such as antioxidant,anti-tumor,anti-microbial and anti-inflammatory activities.It is believed that the mechanisms involved in these bioactivities are due to the modulation of immune system.Recently,the pharmacological validation on immunomodulatory of pentacyclic triterpenes derived from higher plants is very limited and several existence review papers related for this group of compound have not been focused for this activity.In this review,we have highlighted several studies on immunomodulatory potential of botanical pentacyclic triterpenes isolated from wide array of different species of medicinal plants and herbs based on various preclinical in vitro and animal models.This review also attempts to discuss on bioactivities of compouns related with their structure-activity relationship.Hence,the evaluation of pentacyclic triterpenes offers a great opportunity to discover adjuvants and novel therapeutic agents that presented beneficial immunomodulatory properties.展开更多
Two pentacyclic steroidal bitter principles, taccalonolide E and F, have been isolated from Tacca Plantaginea. Their structures were elucidated by spectroscopic methods.
Pentacyclic triterpenoids(PTTs)are a significant class of natural products widely distributed in macrofungi that exhibit notable biological activity.Despite evidence of their efficacy in anticancer,antimicrobial and a...Pentacyclic triterpenoids(PTTs)are a significant class of natural products widely distributed in macrofungi that exhibit notable biological activity.Despite evidence of their efficacy in anticancer,antimicrobial and antiinflammatory contexts,they remain under-investigated relative to their tetracyclic counterparts.This over-sight can be attributed to their comparatively restricted structural diversity and diminished natural abundance.This study systematically collates literature data from the first report of a macrofungal pentacyclic triterpene in 1977.It presents the first comprehensive and systematic compilation and classification of macrofungal penta-cyclic triterpenes and identifies a total of 150 compounds.These compounds are classified based on their skeletal characteristics and categorised into four groups:6/6/6/6/6-ring scaffold;6/6/6/6/5-ring scaffold;lanostanederived typical PTTs;and lanostane-derived non-canonical PTTs.A thorough investigation of the biological activity and pharmacological effects of these compounds was conducted,revealing their diverse bioactivities.These bioactivities include anticancer,antimicrobial,anti-inflammatory and hypoglycaemic properties.This study systematically elucidates the structural and activity diversity of macrofungal pentacyclic triterpenes,providing a theoretical foundation for the development of functional food molecules and novel drug lead compounds while enhancing our understanding of bioactive metabolites in macrofungi.展开更多
Rosa roxburghii Tratt.(Cili)is a species of rose fruit with distinctive characteristics,combining medicinal and edible values.In recent years,it has become the focus of attention in the field of nutrition and health.F...Rosa roxburghii Tratt.(Cili)is a species of rose fruit with distinctive characteristics,combining medicinal and edible values.In recent years,it has become the focus of attention in the field of nutrition and health.From a health perspective,the core advantage of R.roxburghii lies in its high concentration of bioactive substances.Among these substances,pentacyclic triterpenoids are regarded as one of the key substances that contribute to its health-promoting effects.However,the regulatory mechanisms of triterpenoid biosynthesis remain unclear.The present study found that ultraviolet-B(UV-B)radiation increased the total triterpene content of R.roxburghii by 1.49-fold.The key cyclase gene RrOSC4 encodes an oxidosqualene cyclase implicated in the formation ofα/β-amyrin skeletons under UV-B radiation.Co-expression network and promoter analyses identified RrMYB62 as a key regulator of triterpenoid biosynthesis.Furthermore,over-expression of RrMYB62 upregulated the expression of RrOSC4,leading to increased pentacyclic triterpenoids content in‘NC89’tobacco leaves.Results from yeast one-hybrid,dual-luciferase activity and electrophoretic mobility shift assays demonstrated that RrMYB62 directly binds and activates the promoter of RrOSC4 to regulate triterpenoid biosynthesis.Taken together,our findings demonstrate that triterpenoid biosynthesis in R.roxburghii exposed to UV-B radiation is regulated by the RrMYB62-RrOSC4 module.This study revealed the interplay between light signaling and functional phytochemicals,offering a molecular basis for enhancing the fruit quality in the field of food application.展开更多
Objective: To determine whether corosolic acid(CA) targeting nuclear protein expression of Nrf2 activation can be used to attenuate renal damage and preserve renal function in alloxan diabetic mice.Methods: A mouse mo...Objective: To determine whether corosolic acid(CA) targeting nuclear protein expression of Nrf2 activation can be used to attenuate renal damage and preserve renal function in alloxan diabetic mice.Methods: A mouse model with diabetic nephropathy was established to examine the Nrf2 expression. Mice were randomly divided into control, diabetic control, and CA groups treated at 0.4 mg/kg, 2 mg/kg and 10 mg/kg p.o. for 8 weeks. Diabetes was induced in mice by single intraperitoneal injection of alloxan 200 mg/kg in all groups except the control. The mice with fasting blood glucose level over 200 mg/d L were considered as diabetic and were employed in the study. After 4 th and 8 th weeks, urine samples were collected(using metabolic cages) to measure protein and urea. Animals were euthanized, and serum samples were collected to estimate the glucose, creatinine, total protein, urea and blood urea nitrogen. Kidney was isolated at the end of experiment for histology to evaluate anti-oxidant parameters. Immunohistochemistry was performed to examine the Nrf2 expression.Results: CA treatment showed dose dependent reduction in level of biochemical parameters in serum and urine. CA group(10 mg/kg) showed significantly higher body weight and reduced kidney weight. Histopathological examination revealed reduced inflammation, collagen deposition and glomerulosclerosis in renal tissue. CA attenuated renal dysfunction, oxidative stress and inflammatory pro-cytokine levels.Conclusions: CA treatment exhibited ameliorative effect on kidney in mice with its enhanced Nrf2 expression.展开更多
Oleanolic acid(OA),a pentacyclic triterpenoid,exhibits a broad spectrum of biological activities,including antitumor,antiviral,antibacterial,anti-inflammatory,hepatoprotective,hypoglycemic,and hypolipidemic effects.Si...Oleanolic acid(OA),a pentacyclic triterpenoid,exhibits a broad spectrum of biological activities,including antitumor,antiviral,antibacterial,anti-inflammatory,hepatoprotective,hypoglycemic,and hypolipidemic effects.Since its initial isolation and identification,numerous studies have reported on the structural modifications and pharmacological activities of OA and its derivatives.Despite this,there has been a dearth of comprehensive reviews in the past two decades,leading to challenges in subsequent research on OA.Based on the main biological activities of OA,this paper comprehensively summarized the modification strategies and structureactivity relationships(SARs)of OA and its derivatives to provide valuable reference for future investigations into OA.展开更多
The condensates from the Yacheng Gas Field, Ying-Qiong Basins, have unusual chemical characteristics, with distribution dominated by terpanes and steranes derived from higher-plants. Pr/Ph ratios (6-11) are very high....The condensates from the Yacheng Gas Field, Ying-Qiong Basins, have unusual chemical characteristics, with distribution dominated by terpanes and steranes derived from higher-plants. Pr/Ph ratios (6-11) are very high. Drimane, cadinanes and homocadinanes exist in high concentration. Anomalously abundant 18α(H)-oleanane and remarkably abundant bicadinanes are present in Yacheng condensates, while 17α(H)-hopanes are in extremely low concentration. Taraxastane and significantly abundant 17α(H)-diahopanes occur in the condensates. In addition, a number of C 29 and C 30 unknown pentacyclic triterpanes were monitored in the condensates, some of which are abundant. The unknown compounds may be terrestrial biomarkers or their occurrence may suggest a sub-oxic (dyacrobic) clay-rich depositional environment. C 29 homologues are relatively predominant in regular and rearranged steranes. The concentration of diasteranes is markedly higher than that of regular steranes. The characteristics of Yacheng condensates are indicative of terrestrial source input. Based on condensate-condensate and condensate-rock correlations, combined with results of studies on sedimentary facies. Yacheng condensates may be sourced from Yacheng and Lingshui Formations in the Qiongdongnan Basin. The maturity of Yacheng condensate is relatively high, at late oil window stage (corresponding to 0.9%-1.3% R 0), based on sterane and terpane maturity parameters.展开更多
Ursolic acid(UA)is a naturally occurring ursane triterpenoid,which exhibits a wide range of unique biological activities.To clarify its mechanism of action(MOA),a series of fluorescent derivatives of UA(5a-c)were desi...Ursolic acid(UA)is a naturally occurring ursane triterpenoid,which exhibits a wide range of unique biological activities.To clarify its mechanism of action(MOA),a series of fluorescent derivatives of UA(5a-c)were designed and synthesized by conjugation with 7-nitrobenzo-2-oxa-1,3-diazole(NBD)fluorophore.Among them,5c exhibited similar anti-proliferative activity with UA against HCT116 cells(half maximal inhibitory concentration(IC_(50))=9.21±0.50μmol/L).Cell imaging experiment indicated that 5c was rapidly taken up in HCT116 cells in a dose and time-dependent manner.Then,5c was found to localize in endoplasmic reticulum(ER),lysosomes,and mitochondria,but not in nucleus of HCT116 cells by confocal microscopy studies.Preliminary MOA proved that UA induced autophagy with a unique intracellular distribution mechanism involving ER and lysosome.In all,our work provides new clues for revealing the molecular mechanism of UA as an antitumor agent.展开更多
The influenza A virus(IAV),renowned for its high contagiousness and potential to catalyze global pandemics,poses significant challenges due to the emergence of drug-resistant strains.Given the critical role of RNA pol...The influenza A virus(IAV),renowned for its high contagiousness and potential to catalyze global pandemics,poses significant challenges due to the emergence of drug-resistant strains.Given the critical role of RNA polymerase in IAV replication,it stands out as a promising target for anti-IAV therapies.In this study,we identified a novel C-3-substituted oleanolic acid benzyl amide derivative,A5,as a potent inhibitor of the PA_(C)-PB1_(N) polymerase subunit interaction,with an IC_(50) value of 0.96±0.21μmol/L.A5 specifically targets the highly conserved PA_(C) domain and demonstrates remarkable efficacy against both laboratory-adapted and clinically isolated IAV strains,including multidrug-resistant strains,with EC_(50) values ranging from 0.60 to 1.83μmol/L.Notably,when combined with oseltamivir,A5 exhibits synergistic effects both in vitro and in vivo.In a murine model,dosedependent administration of A5 leads to a significant reduction in IAV titers,resulting in a high survival rate among treated mice.Additionally,A5 treatment inhibits virus-induced Toll-like receptor 4 activation,attenuates cytokine responses,and protects against IAV-induced inflammatory responses in macrophages.In summary,A5 emerges as a novel inhibitor with high efficiency and broad-spectrum anti-influenza activity.展开更多
文摘A detailed investigation was carried out to understand how the variations in configurations of the spiroannulated 6-6-6-5-5 pentacyclic diastereoisomers,the key intermediates for the synthesis of two C30 terpene quinonemethides and their stereoisomers,impact the reactivity of cyclopropanation.The configurations at C9,C8,and C14 for all four pentacyclic diastereoisomers involved in the diastereoisomeric mixture were determined through a combination of suitable chemical derivatization and multiple NMR spectroscopic analyses.Based on the defined configuration,the 3D structures of these diastereoisomers were optimized by density functional theory(DFT)calculation.These investigations provide reasonable supports,mainly from the steric considerations,for understanding why different diastereoisomers exhibit markedly different reactivity,as well as regio-and stereo-selectivity for cyclopropanation.In addition,the mechanism for the construction of the spiroannulated 6-6-6-5-5 pentacyclic scaffold via intramolecular Michael/aldol cascade was also investigated by deuterium labeling experiments.
基金supported by the Qi-Huang Chief Scientist Project of the National Administration of Traditional Chinese Medicine(2020).
文摘Phytochemical study of the n-BuOH extract of Ilex asprella resulted in the discovery of ten new pentacyclic triterpenoid glycosides,comprising nine ursane-type glycosides(1-9)and one oleanane-type glycoside(10),along with seven known compounds(11-17).Compound 1 is the first reported 19,22-epoxy ursane triterpenoid glycoside,whereas 4 and 5 are rare examples of ursane triterpenoid glycosides containing a 28,19-lactone group.The structural characterization of these compounds was achieved using spectroscopic and chemical techniques,as well as single-crystal X-ray analysis.Compounds 7,12,15,and 17 exhibited moderate cytotoxic activities against H1975 and HCC827 cancer cells.
文摘Two new pentacyclic triterpene acids, 1a, 3b-dihydroxyl-olean-12-en-28-oic acid and 1a, 2a, 3b-trihydroxyl-olean-12-en-28-oic acid, were isolated from the arial parts of Sabia parviflora.
文摘: Four typical distribution patterns of pentacyclic triterpenoid hydrocarbons (types A-D) are distinguished in the low-mature source rocks from eastern China. Type A has a relatively high content of pentacyclic triterpenes. It exists in immature sediments and the distribution and abundance of triterpenes vary with the maturity of the sediments. An unknown C30 triterpene (UCT2) has also been detected in very shallow sediments. This compound is very unstable and disappears rapidly with the increase of depth. Type B is characterized by a relatively high amount of 17α(H), 21β(H)-30-homohopane. This kind of distribution pattern is common in coals and terrestrial sediments of low maturity. Type C has a relatively high content of diahopane and neohopane series. The analysis shows that this distribution pattern may have an indirect relationship with the input of higher plants despite its microbial source. There are C30—unconfirmed triterpane (UCT2) and a relatively high content of C35 hopane in type D. The distribution patterns of pentacyclic triterpenoids are varied under influences of biological sources, diagentic and sedimentary environments, thermal maturity etc. Therefore, they can provide useful information about the source rocks. Based on geochemical characteristics of the source rocks, the authors postulated that the type B and type C patterns are mainly related to suboxic-anoxic environments. Type D indicates the reducing to anoxic environment, in which C30-UCT3 may be related to some specific biological source in saline environments. The precursors and thermal evolution of some triterpenoid hydrocarbons are also discussed herein.
文摘The title compound 17（S）-methyl-13β-hydroxyl-14（R）,20（S）-epoxy-pregn-4-en-3-one was synthesized by an improved tandem reaction, and its structure was determined by IR, NMR, HR MS and X-ray single-crystal diffraction. The crystal belongs to orthorhombic, space group P212121 with a = 10.55248（15）, b = 12.14700（16）, c = 14.56841（18） ？, V = 1867.39（4） ？3, Z = 4, Dc= 1.175 g/cm3, μ= 0.604 mm-1, F（000） = 720, the final R = 0.0400 and w R = 0.1072 for 3610 observed reflections with I 〉 2σ（I）.
文摘The aim of the current work is to synthesize the new heterocyclic pentacyclic condensed systems that combine benzothiophen and benzimidazole/triazole into one molecule. The dibenzothiophene was taken as an initial compound and by consistent “extension” was annihilated the imidazole and triazole nucleuses. As a result two new pentacyclic systems were produced: 3H-, 7H-diimidazole[4,5-b][5,4-g] dibenzothiophene-5,5-dioxide and 3H-, 7H-ditriazole[4,5-b][5,4-g] dibenzothiophene-5,5-dioxide with the promising antimi-crobial activity. Their spectral characteristics were studied.
基金supported by the National Natural Science Foundation of China(Nos.21572015,21877007,81703540 and 21702007)China Postdoctoral Science Foundation(No.2018M631796)+2 种基金Technology Plan Foundation of Liaoning Province(No.20170520063)Chinese Medicine Related Scientific Research Project of Dalian(No.17Z2013)the open funding of the State Key Laboratory of Phytochemistry and Plant Resources in West China。
文摘The acetyl ester plays an important role for protection of the hydroxyl groups in carbohydrates synthesis.In the present study,we described an efficient deprotection of acetyl group of pentacyclic triterpenoid by using methanolic ammonia in THF solution.Good selectivity for cleaving gal-C2-OAc group of 3β-hydroxy-olean-12-en-28-oic acid 28-N-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside(3) was achieved in the presence of methanolic ammonia within 4 h at low temperature(-60℃) in a yield of 56%.The reaction disclosed here provides a new method for the synthesis of C2 selective modified carbohydrates,which is more useful than conventional synthesis procedure that usually requires many steps including temporary regioselective protection and deprotection.When the reaction temperature was increased from -60℃ to room temperature,the cleavage of the other three acetyl groups of galactose in an order of C4-OAc>C3-OAc>C6-OAc was observed.Based on this study,a plausible route for the deacetylation reaction has been proposed.
文摘A concise and efficient synthesis of the pentacyclic intermediate 1, as a simple model compound of Ecteinascidin 743 and its analogues, is described.
基金the Important Direction Projects of Knowledge Innovation in Resource and Environment Fields, Chinese Academy of Sciences (Grant No. KZCX2-111) and the National Natural Science Foundation of China (Grant No. 40072040).
文摘Abundant terrigenous triterpenoid ketones and a series of hopanoid ketones were detected in a peat sample from the recent Gannan Marsh. The identifications of pen-tacyclic triterpenoid ketones are discussed in detail. Based on the compositional features of pentacyclic triterpenoid ketones in the sample, it is proposed that terrigenous triterpenoid kentones originate directly from organisms or are diagenetic oxidation products of their alcohols, and hopanoid ketones are formed from hopanoids (e.g. hopanoid alcohols and hopenes) by chemical and biochemical processes. These data provide evidence for the applied studies of pentacyclic triterpenoid ketones as biomarker compounds.
基金Acknowledgement This work was supported by the National Natural Science Foundation of China （No. 81560560）, Open-Fund Program of the State Key Laboratory of Natural and Biomimetic Drugs （No. K20160209） and Yunnan Basic Research Project （No. 14051789）.
文摘A series of triterpene dimers bearing different scaffold were designed and synthesized via CuAAC reaction. Their anti-HCV entry activities were evaluated by HCVpp and VSVpp entry assays. It was found that echinocystic acid （EA） and its dimer were still necessary for maintaining anti-HCV entry activity, and replacement of EA by other triterpenes might significantly decrease its anti-viral activities. Using a linker bearing a piperazine group, compound 14 dramatically increased its potency with IC50 at 2.87 nmol/L. In addition, the undesired hemolytic effect of all these compounds was removed.
文摘Botanical pentacyclic triterpenes possessed a broad range of pharmacological activities such as antioxidant,anti-tumor,anti-microbial and anti-inflammatory activities.It is believed that the mechanisms involved in these bioactivities are due to the modulation of immune system.Recently,the pharmacological validation on immunomodulatory of pentacyclic triterpenes derived from higher plants is very limited and several existence review papers related for this group of compound have not been focused for this activity.In this review,we have highlighted several studies on immunomodulatory potential of botanical pentacyclic triterpenes isolated from wide array of different species of medicinal plants and herbs based on various preclinical in vitro and animal models.This review also attempts to discuss on bioactivities of compouns related with their structure-activity relationship.Hence,the evaluation of pentacyclic triterpenes offers a great opportunity to discover adjuvants and novel therapeutic agents that presented beneficial immunomodulatory properties.
基金This research was supported by the National Natural Science Foundation of China.
文摘Two pentacyclic steroidal bitter principles, taccalonolide E and F, have been isolated from Tacca Plantaginea. Their structures were elucidated by spectroscopic methods.
基金the National Natural Science Founda-tion of China(32573114)the Shaanxi Provincial Department of Science and Technology Rural Revitalization Science and Technology Project(No.2025ZY-XCZXZS-21),the National Key Research and Development Program(2021YFD1600401)+2 种基金the Key Core Technology Research and Development in Shaanxi Province Agriculture(2025NYGG010)Un-dergraduate Innovation Fund of Northwest A&F University,China(XN2025025006,X202410712689,and XN2025025024)Science and Technology Research and Development Plan Project of Ankang City,Shaanxi Province(AN2023-NY-01).
文摘Pentacyclic triterpenoids(PTTs)are a significant class of natural products widely distributed in macrofungi that exhibit notable biological activity.Despite evidence of their efficacy in anticancer,antimicrobial and antiinflammatory contexts,they remain under-investigated relative to their tetracyclic counterparts.This over-sight can be attributed to their comparatively restricted structural diversity and diminished natural abundance.This study systematically collates literature data from the first report of a macrofungal pentacyclic triterpene in 1977.It presents the first comprehensive and systematic compilation and classification of macrofungal penta-cyclic triterpenes and identifies a total of 150 compounds.These compounds are classified based on their skeletal characteristics and categorised into four groups:6/6/6/6/6-ring scaffold;6/6/6/6/5-ring scaffold;lanostanederived typical PTTs;and lanostane-derived non-canonical PTTs.A thorough investigation of the biological activity and pharmacological effects of these compounds was conducted,revealing their diverse bioactivities.These bioactivities include anticancer,antimicrobial,anti-inflammatory and hypoglycaemic properties.This study systematically elucidates the structural and activity diversity of macrofungal pentacyclic triterpenes,providing a theoretical foundation for the development of functional food molecules and novel drug lead compounds while enhancing our understanding of bioactive metabolites in macrofungi.
基金supported by the National Key Research and Development Program of China(2024YFD1300803)the Fundamental Research Funds for the Central Universities(2572023AW35)National Natural Science Foundation of China(32501698).
文摘Rosa roxburghii Tratt.(Cili)is a species of rose fruit with distinctive characteristics,combining medicinal and edible values.In recent years,it has become the focus of attention in the field of nutrition and health.From a health perspective,the core advantage of R.roxburghii lies in its high concentration of bioactive substances.Among these substances,pentacyclic triterpenoids are regarded as one of the key substances that contribute to its health-promoting effects.However,the regulatory mechanisms of triterpenoid biosynthesis remain unclear.The present study found that ultraviolet-B(UV-B)radiation increased the total triterpene content of R.roxburghii by 1.49-fold.The key cyclase gene RrOSC4 encodes an oxidosqualene cyclase implicated in the formation ofα/β-amyrin skeletons under UV-B radiation.Co-expression network and promoter analyses identified RrMYB62 as a key regulator of triterpenoid biosynthesis.Furthermore,over-expression of RrMYB62 upregulated the expression of RrOSC4,leading to increased pentacyclic triterpenoids content in‘NC89’tobacco leaves.Results from yeast one-hybrid,dual-luciferase activity and electrophoretic mobility shift assays demonstrated that RrMYB62 directly binds and activates the promoter of RrOSC4 to regulate triterpenoid biosynthesis.Taken together,our findings demonstrate that triterpenoid biosynthesis in R.roxburghii exposed to UV-B radiation is regulated by the RrMYB62-RrOSC4 module.This study revealed the interplay between light signaling and functional phytochemicals,offering a molecular basis for enhancing the fruit quality in the field of food application.
基金the financial support received under University Grants Commission Minor Research Scheme with File no. 47-831/13(WRO), Pune
文摘Objective: To determine whether corosolic acid(CA) targeting nuclear protein expression of Nrf2 activation can be used to attenuate renal damage and preserve renal function in alloxan diabetic mice.Methods: A mouse model with diabetic nephropathy was established to examine the Nrf2 expression. Mice were randomly divided into control, diabetic control, and CA groups treated at 0.4 mg/kg, 2 mg/kg and 10 mg/kg p.o. for 8 weeks. Diabetes was induced in mice by single intraperitoneal injection of alloxan 200 mg/kg in all groups except the control. The mice with fasting blood glucose level over 200 mg/d L were considered as diabetic and were employed in the study. After 4 th and 8 th weeks, urine samples were collected(using metabolic cages) to measure protein and urea. Animals were euthanized, and serum samples were collected to estimate the glucose, creatinine, total protein, urea and blood urea nitrogen. Kidney was isolated at the end of experiment for histology to evaluate anti-oxidant parameters. Immunohistochemistry was performed to examine the Nrf2 expression.Results: CA treatment showed dose dependent reduction in level of biochemical parameters in serum and urine. CA group(10 mg/kg) showed significantly higher body weight and reduced kidney weight. Histopathological examination revealed reduced inflammation, collagen deposition and glomerulosclerosis in renal tissue. CA attenuated renal dysfunction, oxidative stress and inflammatory pro-cytokine levels.Conclusions: CA treatment exhibited ameliorative effect on kidney in mice with its enhanced Nrf2 expression.
基金supported by the Lianyungang Postdoctoral Research Funding Program(No.LYG20210018).
文摘Oleanolic acid(OA),a pentacyclic triterpenoid,exhibits a broad spectrum of biological activities,including antitumor,antiviral,antibacterial,anti-inflammatory,hepatoprotective,hypoglycemic,and hypolipidemic effects.Since its initial isolation and identification,numerous studies have reported on the structural modifications and pharmacological activities of OA and its derivatives.Despite this,there has been a dearth of comprehensive reviews in the past two decades,leading to challenges in subsequent research on OA.Based on the main biological activities of OA,this paper comprehensively summarized the modification strategies and structureactivity relationships(SARs)of OA and its derivatives to provide valuable reference for future investigations into OA.
文摘The condensates from the Yacheng Gas Field, Ying-Qiong Basins, have unusual chemical characteristics, with distribution dominated by terpanes and steranes derived from higher-plants. Pr/Ph ratios (6-11) are very high. Drimane, cadinanes and homocadinanes exist in high concentration. Anomalously abundant 18α(H)-oleanane and remarkably abundant bicadinanes are present in Yacheng condensates, while 17α(H)-hopanes are in extremely low concentration. Taraxastane and significantly abundant 17α(H)-diahopanes occur in the condensates. In addition, a number of C 29 and C 30 unknown pentacyclic triterpanes were monitored in the condensates, some of which are abundant. The unknown compounds may be terrestrial biomarkers or their occurrence may suggest a sub-oxic (dyacrobic) clay-rich depositional environment. C 29 homologues are relatively predominant in regular and rearranged steranes. The concentration of diasteranes is markedly higher than that of regular steranes. The characteristics of Yacheng condensates are indicative of terrestrial source input. Based on condensate-condensate and condensate-rock correlations, combined with results of studies on sedimentary facies. Yacheng condensates may be sourced from Yacheng and Lingshui Formations in the Qiongdongnan Basin. The maturity of Yacheng condensate is relatively high, at late oil window stage (corresponding to 0.9%-1.3% R 0), based on sterane and terpane maturity parameters.
基金supported in part by the National Key Research and Development Program of China(No.2022YFC3400501)the National Natural Science Foundation of China(Nos.81825020 and 82150208 to H.L.)+2 种基金the Shanghai Science and Technology Commission Biomedical Science and Technology Support Special Project(Nos.21S11907900 and 20S11901000 to Z.Z.)sponsored by the National Program for Special Supports of Eminent Professionalsthe National Program for Support of Top-Notch Young Professionals.
文摘Ursolic acid(UA)is a naturally occurring ursane triterpenoid,which exhibits a wide range of unique biological activities.To clarify its mechanism of action(MOA),a series of fluorescent derivatives of UA(5a-c)were designed and synthesized by conjugation with 7-nitrobenzo-2-oxa-1,3-diazole(NBD)fluorophore.Among them,5c exhibited similar anti-proliferative activity with UA against HCT116 cells(half maximal inhibitory concentration(IC_(50))=9.21±0.50μmol/L).Cell imaging experiment indicated that 5c was rapidly taken up in HCT116 cells in a dose and time-dependent manner.Then,5c was found to localize in endoplasmic reticulum(ER),lysosomes,and mitochondria,but not in nucleus of HCT116 cells by confocal microscopy studies.Preliminary MOA proved that UA induced autophagy with a unique intracellular distribution mechanism involving ER and lysosome.In all,our work provides new clues for revealing the molecular mechanism of UA as an antitumor agent.
基金supported by the Major Scientific and Technological Projects of Guangdong Province(No.2023B1111050008,China)Science and Technology Innovation Project of Guangdong Provincial Drug Administration(No.2022ZDZ08,China)+3 种基金Post Scientist Fund awarded by Chinese Academy of Traditional Chinese Medicine(No.ZZ13-035-02,China)to Shuwen LiuThe-National Natural Science Foundation of China(No.82073722)the Guangdong Basic and Applied Basic Research Foundation(No.2025A1515010495,China)to Gaopeng SongRegional joint foundation of basic and applied basic research in guangdong province(No.2023A1515111165,China)to Chan Yang.
文摘The influenza A virus(IAV),renowned for its high contagiousness and potential to catalyze global pandemics,poses significant challenges due to the emergence of drug-resistant strains.Given the critical role of RNA polymerase in IAV replication,it stands out as a promising target for anti-IAV therapies.In this study,we identified a novel C-3-substituted oleanolic acid benzyl amide derivative,A5,as a potent inhibitor of the PA_(C)-PB1_(N) polymerase subunit interaction,with an IC_(50) value of 0.96±0.21μmol/L.A5 specifically targets the highly conserved PA_(C) domain and demonstrates remarkable efficacy against both laboratory-adapted and clinically isolated IAV strains,including multidrug-resistant strains,with EC_(50) values ranging from 0.60 to 1.83μmol/L.Notably,when combined with oseltamivir,A5 exhibits synergistic effects both in vitro and in vivo.In a murine model,dosedependent administration of A5 leads to a significant reduction in IAV titers,resulting in a high survival rate among treated mice.Additionally,A5 treatment inhibits virus-induced Toll-like receptor 4 activation,attenuates cytokine responses,and protects against IAV-induced inflammatory responses in macrophages.In summary,A5 emerges as a novel inhibitor with high efficiency and broad-spectrum anti-influenza activity.
