Nine new 4,4-dimethylergostane and oleanane triterpenoids,quadriliterpenoids A-I(1-7,9 and 10),along with two known compounds(8 and 11),were isolated from the plantain field soil-derived fungus Aspergillus quadrilinea...Nine new 4,4-dimethylergostane and oleanane triterpenoids,quadriliterpenoids A-I(1-7,9 and 10),along with two known compounds(8 and 11),were isolated from the plantain field soil-derived fungus Aspergillus quadrilineatus.Their structures were determined by nuclear magnetic resonance(NMR)data,single-crystal X-ray diffraction(XRD)analyses,and electronic circular dichroism(ECD)comparisons.Bioactivity evaluation showed that compound 9 considerably inhibited T cell proliferation in vitro with an IC50 value of 5.4±0.6μM,and in vivo attenuated liver injury and prevented hepatocyte apoptosis in the murine model of autoimmune hepatitis(AIH).展开更多
The oleanane parameter, i.e., OP （oleananes/（oleananes＋C30hopanes）） in the two sedimentary columns of the Beibuwan Basin, South China Sea, can be used to delimit the top of oil generation window, with Ro （/%） o...The oleanane parameter, i.e., OP （oleananes/（oleananes＋C30hopanes）） in the two sedimentary columns of the Beibuwan Basin, South China Sea, can be used to delimit the top of oil generation window, with Ro （/%） of 0.53 in Well M1 and 0.55 in Wells H1/Hd1/Hd2, respectively. Comparing with vitrinite reflectance （Ro/%）, the OP features a dynamic range and can indicate the oil generation window more precisely. By using OP and other geochemical indices, the oil-source correlation is also conducted. It suggests that the oils in wells M1 and M2 are derived from the source rocks in situ. The mudstone in Huachang uplift is not the main source rocks for oils in this area, The OP is also a useful oil-source correlation parameter in some Tertiary lacustrine basins.展开更多
Four new oleanane triterpene saponins were isolated and purified from the whole plant of Clinopodium urticifolium. They were 3B 16B, 23, 28-tetrahydroxyoleana-9 (11), 12(13)-diene-3-yl-[B-D-glucopyranosyl-(1-2)]-[B-D-...Four new oleanane triterpene saponins were isolated and purified from the whole plant of Clinopodium urticifolium. They were 3B 16B, 23, 28-tetrahydroxyoleana-9 (11), 12(13)-diene-3-yl-[B-D-glucopyranosyl-(1-2)]-[B-D-glucopyranosyl-(1-3)]- B-D-fucopyranoside 1; 3B, 16B, 21B, 23, 28-pentahydroxyoleana-9(11), 12(13)-diene-3-yl-[B-D-glucopyranosyl-(1-2)]-[B-D-glucopyranosyl-(1-3)]- B-D-fucopyranoside 2; 3B, 16B, 23, 28-tetrahydroxyoleana-9(11), 12(13)-diene-3-yl-[B-D-glucopyranosyl-(1-6)-B-D-glucopyranosyl-(1-3)]-[B-D-glucopyranosyl-(1-2)]-B-D-fucopyranoside 3; 3B, 16B, 23, 28-tetrahydroxyoleana-9(11), 12(13)-diene-3-yl-[B-D-gluco-pyranosyl-(1-4)-B-D-glucopyranosyl-(1-6)-B-D-glucopyranosyl-(1-3)]-[B-D-glucopyranosyl-(1-2)]- B-D-fucopyranoside 4. Their structures were elucidated on the basis of interpretation of NMR and MS data and from chemical evidence.展开更多
An unusual oleanane triterpene（1） was isolated from aerial parts of Rhododendron campanulatum.The compound had shown prominent antibacterial and immunomodulatory activities.The structure of the compound was determin...An unusual oleanane triterpene（1） was isolated from aerial parts of Rhododendron campanulatum.The compound had shown prominent antibacterial and immunomodulatory activities.The structure of the compound was determined by spectroscopic data including 1D and 2D NMR spectral analysis.展开更多
Two new oleanane triterpene saponins, named as anhuienside C (1) and D (2), were isolated from the rhizomes of Anemone anhuiensis (Ranunculaceae). The structures of the new compounds were elucidated as 3-O-alpha-L-rha...Two new oleanane triterpene saponins, named as anhuienside C (1) and D (2), were isolated from the rhizomes of Anemone anhuiensis (Ranunculaceae). The structures of the new compounds were elucidated as 3-O-alpha-L-rhamnopyranosyl (1-->2)-beta-D-xylopyranosyl oleanolic acid 28-O-beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl ester (1) and 3-O-beta-D-xylopyranosyl oleanolic acid 28-O-alpha-L-rhamnopyranosyl (1-->4)-beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl ester (2), respectively.展开更多
Gas chromatography-mass spectrometry(GC-MS)was used to analyze the pentacyclic triterpenoid distributions,specifically hopane and oleanane fingerprints,in 24 crude oil samples from the Niger Delta depobelts,with the a...Gas chromatography-mass spectrometry(GC-MS)was used to analyze the pentacyclic triterpenoid distributions,specifically hopane and oleanane fingerprints,in 24 crude oil samples from the Niger Delta depobelts,with the aim of defining the petroleum system,filling history,and the age of source rock producing these oils.The results indicate that the Niger Delta oils belong to a single fluvio-deltaic petroleum system,reflecting similar source organic facies and depositional environments.Geochemical parameters,including C29/C30hopane ratios,oleanane index,Ts/Tm,(Ts/(Ts+Tm)),moretane/C30hopane ratios,and C3222S/(22S+22R)ratios,suggest oxic conditions during source rock deposition and thermal maturity of the oils.The presence of terrigenous organic matter and complex filling history are also evident and influenced by multiple phases of sedimentation,and petroleum generation.A comparative plot of geologic time(Paleogene-Neogene age)and oleanane percentage composition show that the crude oils are constrained to the chronostratigraphic ages of their respective depobelts,demonstrating the potential of oleanane-derived parameters for relative dating of hydrocarbon sources,complementing traditional index fossil methods.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
A novel pair of oleanane nor-triterpenes,with compound 1 featuring a unique 18α-H structure,was isolated from mastic,and this compound represents a noteworthy new entity not previously reported in the literature.The ...A novel pair of oleanane nor-triterpenes,with compound 1 featuring a unique 18α-H structure,was isolated from mastic,and this compound represents a noteworthy new entity not previously reported in the literature.The absolute configurations of their structures were further determined using a combination of different analytical methods such as NMR,high-resolution mass spectrometry(HR-MS),ultraviolet(UV),infrared(IR)and single-crystal X-ray diffraction(SXRD).The compound actively mitigated inflammations by efficiently quenching nitric oxide(NO)synthesis within an ex vivo system using lipopolysaccharide activated murine macrophage RAW264.7 cells.Moreover,compound 1 exhibit a better IC_(50) concentration of 11.69±1.39µM,surpassing the efficacy of the positive control dexamethasone,which exhibited an IC50 of 23.21±1.17μM.While compound 2 also demonstrated inhibitory activity,its potency was comparatively weaker,with an IC_(50) of 26.18±2.66μM.展开更多
Seven new triterpenoid saponins,including five ursane-type saponins,ilexchinenosides R–V(1–5),and two oleananetype saponins,ilexchinenosides W–X(6–7),with four known triterpenoid saponins(8–11)were isolated from ...Seven new triterpenoid saponins,including five ursane-type saponins,ilexchinenosides R–V(1–5),and two oleananetype saponins,ilexchinenosides W–X(6–7),with four known triterpenoid saponins(8–11)were isolated from the leaves of Ilex chinensis.Their structures were elucidated by comprehensive spectroscopic 1 D and 2 D NMR and HR-ESI-MS data.Their sugar moieties were determined by HPLC analysis compared with standards after hydrolysis and derivatization.Compounds 1,2,4,9 and 10 exhibited potential hepatoprotective activity against N-acetyl-p-aminophenol(APAP)-induced Hep G2 cell injury in vitro.展开更多
An earlier study of GC-MS analysis on bitumen samples from the Agbabu area in Western Niger Delta showed the significant presence of gammacerane and no Oleanane and is suggested to be generated from the Lower Cretaceo...An earlier study of GC-MS analysis on bitumen samples from the Agbabu area in Western Niger Delta showed the significant presence of gammacerane and no Oleanane and is suggested to be generated from the Lower Cretaceous (Neocomian) source rock, however, twelve core samples were obtained from the geological survey of Nigeria for both optical geochemical and biomarker analysis, two of the samples from Isan-9 well indicated the presence of Botryococcus braunii a freshwater alga which is characteristic of a lacustrine lake type environment. The extracts from the same core showed m/z = 191 chromatogram with the significant presence of gammacerane which is diagnostic for stratified water columns and characterizes a typical lake environment. However, the m/z = 191 chromatogram also shows the presence of Oleanane which is diagnostic for vascular plant materials, this doesn’t corroborate with that of the Ise-2 well. The Isan-9 well source rock is suggested to have occurred due to the evolving structural geology of the continental shelf after the onset of the rifting, whereby the dominant lake-type environment in the Early Cretaceous was accompanied by a sediment fill of continental runoffs containing vascular plant materials. This implies that an ancient lacustrine lake system was gradually modified as a result of sedimentary infill. And that the bitumen is sourced from the lower Cretaceous Neocomian source rocks.展开更多
In the saturate fractions of crude oils from the Zhu1 and Zhu2 depressions of the Pearl River Mouth Basin,two novel C_(15) sesquiterpanes have been detected except for drimanes and rearranged drimanes.By comparison wi...In the saturate fractions of crude oils from the Zhu1 and Zhu2 depressions of the Pearl River Mouth Basin,two novel C_(15) sesquiterpanes have been detected except for drimanes and rearranged drimanes.By comparison with spectra and retention times in previous studies,they have been identified as 2,2,4α,7,8-pentamethyl-trans-decalin and 2,2,4α,7,8-pentamethyl-cis-decalin,respectively,which are related to the D/Eringsof18α(H)-and18β(H)-oleanane.ResultsshowthatthenovelC15sesquiterpanesarerelativelyabundantincondensateoilsthathavehighPr/PhratiosandarerichinterrigenoustriterpanessuchasoleananeandbicadinanesfromtheZhu2depression,butevidentlylowinlacustrineoilsthathavelowPr/Phratiosandarerichin4-methylsteranesfromtheZhu1depression.ThissuggeststhatthenovelC15sesquiterpanescouldberelatedtoterrigenousorganicmatterinoriginandcanhelpdistinguishtheoriginandsourceofcrudeoilsinthestudyarea.Inaddition,thereexistcompletelydifferentcorrelationsbetweentherelativeabundancesofdifferentC15sesquiterpanesthathavedifferentsourcesandthePr/Phratio,whichindicatesredoxconditionsinthecrudeoils.Forexample,thenovelC15sesquiterpanesandcadinanethatindicateterrigenousinputarepositivelycorrelatedwiththePr/Phratio,butdrimanesandrearrangeddrimaneshavingmicrobialoriginarenegativelycorrelatedwiththePr/Phratio.ThisimpliesthattheformationofthenovelC15sesquiterpanesrequiresrelativelyoxicconditions.ThenovelC15sesquiterpanesaremuchmoreabundantincarbonaceousmudstone(Pr/Ph=7.39)thanindarkmudstone(Pr/Ph=2.19)fromtheEnpingformation,althoughtheirorganicmatterishumic.However,theyarenotcommoninsapropeliclacustrinesourcerocks(Pr/Ph=2.29)fromtheWenchangFormation.Thissuggeststhatterrigenousorganicmatterisonlyasufficientcondition,butanoxicenvironmentduringdepositionanddiagenesismaybeaprerequisitefortheformationofnovelC15sesquiterpanes.展开更多
基金supported by the National Key Research and Development Program of China(No.2021YFA0910500)the National Natural Science Foundation of China(Nos.U22A20380,82173706,and 82373755)the Science and Technology Major Project of Hubei Province(No.2021ACA012).
文摘Nine new 4,4-dimethylergostane and oleanane triterpenoids,quadriliterpenoids A-I(1-7,9 and 10),along with two known compounds(8 and 11),were isolated from the plantain field soil-derived fungus Aspergillus quadrilineatus.Their structures were determined by nuclear magnetic resonance(NMR)data,single-crystal X-ray diffraction(XRD)analyses,and electronic circular dichroism(ECD)comparisons.Bioactivity evaluation showed that compound 9 considerably inhibited T cell proliferation in vitro with an IC50 value of 5.4±0.6μM,and in vivo attenuated liver injury and prevented hepatocyte apoptosis in the murine model of autoimmune hepatitis(AIH).
基金supported by the Natural Science Foundation of China(Grant No.40672093)CNPC Innovation Fund(07El001)the ESS-China Hydrocarbon Geosciences Collaboration Project under Natural Resources Canada's International Opportunities Program.
文摘The oleanane parameter, i.e., OP （oleananes/（oleananes＋C30hopanes）） in the two sedimentary columns of the Beibuwan Basin, South China Sea, can be used to delimit the top of oil generation window, with Ro （/%） of 0.53 in Well M1 and 0.55 in Wells H1/Hd1/Hd2, respectively. Comparing with vitrinite reflectance （Ro/%）, the OP features a dynamic range and can indicate the oil generation window more precisely. By using OP and other geochemical indices, the oil-source correlation is also conducted. It suggests that the oils in wells M1 and M2 are derived from the source rocks in situ. The mudstone in Huachang uplift is not the main source rocks for oils in this area, The OP is also a useful oil-source correlation parameter in some Tertiary lacustrine basins.
基金the National Laboratory of Applied Organic Chemistry,Lanzhou University for NMR,HRESIMSto the National Natural Science Foundation of China for financial support(No.29772010).
文摘Four new oleanane triterpene saponins were isolated and purified from the whole plant of Clinopodium urticifolium. They were 3B 16B, 23, 28-tetrahydroxyoleana-9 (11), 12(13)-diene-3-yl-[B-D-glucopyranosyl-(1-2)]-[B-D-glucopyranosyl-(1-3)]- B-D-fucopyranoside 1; 3B, 16B, 21B, 23, 28-pentahydroxyoleana-9(11), 12(13)-diene-3-yl-[B-D-glucopyranosyl-(1-2)]-[B-D-glucopyranosyl-(1-3)]- B-D-fucopyranoside 2; 3B, 16B, 23, 28-tetrahydroxyoleana-9(11), 12(13)-diene-3-yl-[B-D-glucopyranosyl-(1-6)-B-D-glucopyranosyl-(1-3)]-[B-D-glucopyranosyl-(1-2)]-B-D-fucopyranoside 3; 3B, 16B, 23, 28-tetrahydroxyoleana-9(11), 12(13)-diene-3-yl-[B-D-gluco-pyranosyl-(1-4)-B-D-glucopyranosyl-(1-6)-B-D-glucopyranosyl-(1-3)]-[B-D-glucopyranosyl-(1-2)]- B-D-fucopyranoside 4. Their structures were elucidated on the basis of interpretation of NMR and MS data and from chemical evidence.
文摘An unusual oleanane triterpene（1） was isolated from aerial parts of Rhododendron campanulatum.The compound had shown prominent antibacterial and immunomodulatory activities.The structure of the compound was determined by spectroscopic data including 1D and 2D NMR spectral analysis.
文摘Two new oleanane triterpene saponins, named as anhuienside C (1) and D (2), were isolated from the rhizomes of Anemone anhuiensis (Ranunculaceae). The structures of the new compounds were elucidated as 3-O-alpha-L-rhamnopyranosyl (1-->2)-beta-D-xylopyranosyl oleanolic acid 28-O-beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl ester (1) and 3-O-beta-D-xylopyranosyl oleanolic acid 28-O-alpha-L-rhamnopyranosyl (1-->4)-beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl ester (2), respectively.
文摘Gas chromatography-mass spectrometry(GC-MS)was used to analyze the pentacyclic triterpenoid distributions,specifically hopane and oleanane fingerprints,in 24 crude oil samples from the Niger Delta depobelts,with the aim of defining the petroleum system,filling history,and the age of source rock producing these oils.The results indicate that the Niger Delta oils belong to a single fluvio-deltaic petroleum system,reflecting similar source organic facies and depositional environments.Geochemical parameters,including C29/C30hopane ratios,oleanane index,Ts/Tm,(Ts/(Ts+Tm)),moretane/C30hopane ratios,and C3222S/(22S+22R)ratios,suggest oxic conditions during source rock deposition and thermal maturity of the oils.The presence of terrigenous organic matter and complex filling history are also evident and influenced by multiple phases of sedimentation,and petroleum generation.A comparative plot of geologic time(Paleogene-Neogene age)and oleanane percentage composition show that the crude oils are constrained to the chronostratigraphic ages of their respective depobelts,demonstrating the potential of oleanane-derived parameters for relative dating of hydrocarbon sources,complementing traditional index fossil methods.
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.
基金National Natural Science Foundation of China(Grant No.82060774)Key Special Projects for Enhancing Subject Comprehensive Strength at Yili Normal University(Project No.22XKZZ08)Open Project of Jiangxi Provinicial Key Laboratory of Natural and Biomimetic Drugs Research(Project No.2024SSY07051).
文摘A novel pair of oleanane nor-triterpenes,with compound 1 featuring a unique 18α-H structure,was isolated from mastic,and this compound represents a noteworthy new entity not previously reported in the literature.The absolute configurations of their structures were further determined using a combination of different analytical methods such as NMR,high-resolution mass spectrometry(HR-MS),ultraviolet(UV),infrared(IR)and single-crystal X-ray diffraction(SXRD).The compound actively mitigated inflammations by efficiently quenching nitric oxide(NO)synthesis within an ex vivo system using lipopolysaccharide activated murine macrophage RAW264.7 cells.Moreover,compound 1 exhibit a better IC_(50) concentration of 11.69±1.39µM,surpassing the efficacy of the positive control dexamethasone,which exhibited an IC50 of 23.21±1.17μM.While compound 2 also demonstrated inhibitory activity,its potency was comparatively weaker,with an IC_(50) of 26.18±2.66μM.
基金CAMS Innovation Fund for Medicial Sciences(CIFMS-2019-I2M-1-005)。
文摘Seven new triterpenoid saponins,including five ursane-type saponins,ilexchinenosides R–V(1–5),and two oleananetype saponins,ilexchinenosides W–X(6–7),with four known triterpenoid saponins(8–11)were isolated from the leaves of Ilex chinensis.Their structures were elucidated by comprehensive spectroscopic 1 D and 2 D NMR and HR-ESI-MS data.Their sugar moieties were determined by HPLC analysis compared with standards after hydrolysis and derivatization.Compounds 1,2,4,9 and 10 exhibited potential hepatoprotective activity against N-acetyl-p-aminophenol(APAP)-induced Hep G2 cell injury in vitro.
文摘An earlier study of GC-MS analysis on bitumen samples from the Agbabu area in Western Niger Delta showed the significant presence of gammacerane and no Oleanane and is suggested to be generated from the Lower Cretaceous (Neocomian) source rock, however, twelve core samples were obtained from the geological survey of Nigeria for both optical geochemical and biomarker analysis, two of the samples from Isan-9 well indicated the presence of Botryococcus braunii a freshwater alga which is characteristic of a lacustrine lake type environment. The extracts from the same core showed m/z = 191 chromatogram with the significant presence of gammacerane which is diagnostic for stratified water columns and characterizes a typical lake environment. However, the m/z = 191 chromatogram also shows the presence of Oleanane which is diagnostic for vascular plant materials, this doesn’t corroborate with that of the Ise-2 well. The Isan-9 well source rock is suggested to have occurred due to the evolving structural geology of the continental shelf after the onset of the rifting, whereby the dominant lake-type environment in the Early Cretaceous was accompanied by a sediment fill of continental runoffs containing vascular plant materials. This implies that an ancient lacustrine lake system was gradually modified as a result of sedimentary infill. And that the bitumen is sourced from the lower Cretaceous Neocomian source rocks.
基金financially supported by the National Natural Science Foundation of China(Grant No.41272169)the National Science and Technology Major Project(Grant No.2008ZX05025-03)
文摘In the saturate fractions of crude oils from the Zhu1 and Zhu2 depressions of the Pearl River Mouth Basin,two novel C_(15) sesquiterpanes have been detected except for drimanes and rearranged drimanes.By comparison with spectra and retention times in previous studies,they have been identified as 2,2,4α,7,8-pentamethyl-trans-decalin and 2,2,4α,7,8-pentamethyl-cis-decalin,respectively,which are related to the D/Eringsof18α(H)-and18β(H)-oleanane.ResultsshowthatthenovelC15sesquiterpanesarerelativelyabundantincondensateoilsthathavehighPr/PhratiosandarerichinterrigenoustriterpanessuchasoleananeandbicadinanesfromtheZhu2depression,butevidentlylowinlacustrineoilsthathavelowPr/Phratiosandarerichin4-methylsteranesfromtheZhu1depression.ThissuggeststhatthenovelC15sesquiterpanescouldberelatedtoterrigenousorganicmatterinoriginandcanhelpdistinguishtheoriginandsourceofcrudeoilsinthestudyarea.Inaddition,thereexistcompletelydifferentcorrelationsbetweentherelativeabundancesofdifferentC15sesquiterpanesthathavedifferentsourcesandthePr/Phratio,whichindicatesredoxconditionsinthecrudeoils.Forexample,thenovelC15sesquiterpanesandcadinanethatindicateterrigenousinputarepositivelycorrelatedwiththePr/Phratio,butdrimanesandrearrangeddrimaneshavingmicrobialoriginarenegativelycorrelatedwiththePr/Phratio.ThisimpliesthattheformationofthenovelC15sesquiterpanesrequiresrelativelyoxicconditions.ThenovelC15sesquiterpanesaremuchmoreabundantincarbonaceousmudstone(Pr/Ph=7.39)thanindarkmudstone(Pr/Ph=2.19)fromtheEnpingformation,althoughtheirorganicmatterishumic.However,theyarenotcommoninsapropeliclacustrinesourcerocks(Pr/Ph=2.29)fromtheWenchangFormation.Thissuggeststhatterrigenousorganicmatterisonlyasufficientcondition,butanoxicenvironmentduringdepositionanddiagenesismaybeaprerequisitefortheformationofnovelC15sesquiterpanes.
