Objective:To analyze the antioxidant prenylilavonoids in different parts of Macaranga tanarius(M.tanarius)(Euphorbiaceae)including the leaf,petiole,stem,leaflet,flower and fruit(only in female plant),and to evaluate t...Objective:To analyze the antioxidant prenylilavonoids in different parts of Macaranga tanarius(M.tanarius)(Euphorbiaceae)including the leaf,petiole,stem,leaflet,flower and fruit(only in female plant),and to evaluate their antioxidant properties.Methods:Methanol extracts of each part of M.tanarius were prepared and five prenylilavonoids in them were quantitatively analyzed using HPLC.The fruits from female plant were further separated into seed,pericarp,and glandular trichome.After the quantitative analyses of prenylflavonoids in each part of M.tanarius,antioxidant activity of the extracts was evaluated by 2,2-diphenyl-l-picryI-hydrazyl(DPPH)radical scavenging assay.Results:The leaf of M.tanarius contained two prenylflavonoids as main components in both male and female plants.Both flowers(male and female)contained five kinds of prenylflavonoids.In the petiole,stem and leaflet of both male and female plants,the prenylflavonoids were not delected or their amounts were very low.Five kinds of prenylflavonoids were detected in the seed,pericarp and glandular trichome of female M.tanarius.In particular,the glandular trichome had the highest level of total prenylflavonoids(235 mg/g of fresh plant).DPPH radical scavenging activity of all parts was more than 30%.Conclusions:We found that different parts of M.tanarius contained antioxidant prenylflavonoids.In particular,not only the glandular trichome but also the leaf contained prenylflavonoids,which indicated that M.tanarius may be developed as a functional plant,because the leaves of this plant can be easily collected.展开更多
Three new minor prenylated flavonoids,named macadenanthins A–C(1–3),together with three known ones(4–6),were isolated from the twigs of Macaranga adenantha.Their structures were elucidated on the basis of extensive...Three new minor prenylated flavonoids,named macadenanthins A–C(1–3),together with three known ones(4–6),were isolated from the twigs of Macaranga adenantha.Their structures were elucidated on the basis of extensive spectroscopic analysis including NMR,UV and MS.The prenyl moieties in compounds 1–3 were further modified by cyclization and hydroxylation.The new compounds were tested for their cytotoxicity against four cancer cell lines(MCF-7,Hep G2,Hela and P388)and showed IC50 values in the range of 13.76–22.27 lM.展开更多
Three new C-methylated and isoprenylated chalcone derivatives,dentichalcones A–C(1–3),together with six known compounds(4–9),were isolated from the twigs and leaves of Macaranga denticulata.Their structures were el...Three new C-methylated and isoprenylated chalcone derivatives,dentichalcones A–C(1–3),together with six known compounds(4–9),were isolated from the twigs and leaves of Macaranga denticulata.Their structures were elucidated by spectroscopic analysis,including 1D,2D NMR,and MS data.The known compounds,(2E)-1-(5,7-dihydroxy-2,2,6-trimethyl-2H-benzopyran-8-yl)-3-(4-methoxyphenyl)-2-propen-1-one(4),(2E)-1-(5,7-dihydroxy-2,2-dimethyl-2H-benzopyran-8-yl)-3-phenyl-2-propen-1-one(5),laxichalcone(6),macarangin(7),bonanniol A(8),and bonannione A(9),showed inhibitory activities against protein tyrosine phosphatase 1B(PTP1B)in vitro.Graphical Abstract Three new C-methylated and isoprenylated chalcone derivatives,dentichalcones A–C(1–3),together with six known compounds,were isolated from the twigs and leaves of Macaranga denticulata.Some compounds showed inhibitory activities against PTP1B in vitro.展开更多
Objectives: To investigate antimicrobial and cytotoxic potentials as well as chemical constituents of extracts from Macaranga barteri(M. barteri).Methods: Antimicrobial activity was carried out using micro-dilution, c...Objectives: To investigate antimicrobial and cytotoxic potentials as well as chemical constituents of extracts from Macaranga barteri(M. barteri).Methods: Antimicrobial activity was carried out using micro-dilution, cell culture and GC–MS methods were employed to determine the cytotoxicity and chemical constituents of the extracts respectively.Results: Marked activity was observed in methanol(ME) fraction [MIC_(50):(0.097 7–6.250 0) mg/mL] compared to hexane and ethyl acetate fractions. Aeromonas hydrophila(environmental strain) and Shigella sonnei(ATCC 29930) were the most susceptible pathogens to ME and ciprofloxacin(Cl) at MIC_(50) value of 0.097 7 and < 0.019 5 mg/mL respectively. Cryptococcus neoformans(ATCC 66031) was susceptible to ME at 0.195 3 mg/mL compared to fluconazole at 10.000 0 mg/mL. Decreased viability of the Vero cells was observed at the concentrations of 0.1–1.0 mg/mL. The lethal dose(LC_(50))of hexane, ethyl acetate and methanol fractions were recorded at(0.30 ± 0.07),(0.52 ± 0.05) and(0.22 ± 0.04) mg/mL, respectively. Some of the compounds identified from ME were caryophyllene(25.21%), neophytadiene(11.90%), a-humulene(7.67%),phytol(4.40%), ethyl ester hexadecanoic acid(4.04%) and nerolidol(2.83%) which were known to have various antimicrobial activities.Conclusions: Methanol fraction of M. barteri is a potent and safe antimicrobial and antifungal alternative which can be useful in the search for new antimicrobial drugs. The study also confirmed the orthodox usage of M. barteri in combating infectious diseases.展开更多
Objective:To study constituents of the leaves of Macaranga hemsleyana,and evaluate their inhibitory effects against NOD-like receptor thermal protein domain associated protein 3(NLRP3)inflammasome activation,and antip...Objective:To study constituents of the leaves of Macaranga hemsleyana,and evaluate their inhibitory effects against NOD-like receptor thermal protein domain associated protein 3(NLRP3)inflammasome activation,and antiproliferative activity.Methods:The constituents were isolated and purified by column chromatography on MCI gel CHP20P/P120,silica gel,Sephadex LH-20,and HPLC.The structures of compounds were determined by 1D,2D NMR,and HR-ESI-MS data.The inhibitory effect of compounds on inflammasome activation was determined by lactate dehydrogenase(LDH)procedure.The antiproliferative activity was evaluated using MTT assay.Results:The study led to the isolation of 23 compounds,including one new compound,identified as(2Z)-3-[4-(β-D-glucopyranosyloxy)-2′-hydroxy-5′-methoxyphenyl]-2-propenoic acid(1),together with 22 known compounds recognized as 1,4-dihydro-4-oxo-3-pyridinecarbonitrile(2),methyl 4-methoxynicotinate(3),4-methoxynicotinonitrile(4),1-(3-O-β-D-glucopyranosyl-4,5-dihydroxyphenyl)-ethanone(5),neoisoastilbin(6),isoastilbin(7),aromadendrin(8),neoastilbin(9),astilbin(10),quercitrin(11),neoschaftoside(12),apigenin 6,8-bis-C-α-L-arabinoside(13),vitexin(14),bergenin(15),scopoletin(16),glucopyranoside salicyl(17),koaburside(18),benzylβ-D-glucoside(19),icariside B5(20),roseoside(21),loliolide(22),and adenosine(23).The tested compounds did not show LDH inhibition nor antiproliferative activity.Conclusion:Compound 1 was a new glycoside.Compounds 2 and 3 were obtained for the first time from natural source.The 22 known compounds constituted of alkaloids(2–4,23),phenolics(5,15,17,18),flavonoids(6–14),coumarin(16),benzyl glycoside(19),and norsesquiterpenes(20–22).All the compounds,1–23,were revealed from M.hemsleyana for the first time.This is the initial uncovering of molecules 1–10,12,13,17–19,and 23 from the genus Macaranga.The isolated compounds,11,14–16,and 20–22 established taxonomic classification of M.hemsleyana in Euphorbiaceae family.Flavonoids were outstanding as chemosystematic markers of Macaranga genus.展开更多
Nervonic acid(NA)is a very-long-chain monounsaturated fatty acid with pharmaceutical and nutraceutical functions that plays an important role in treating several neurological disorders.One major source of NA is plant ...Nervonic acid(NA)is a very-long-chain monounsaturated fatty acid with pharmaceutical and nutraceutical functions that plays an important role in treating several neurological disorders.One major source of NA is plant seed oil.Here we report fatty acid profiles of seeds and germplasm diversity of six plant species,including three woody plants with high amounts of NA-enriched seed oil,Malania oleifera,Macaranga adenantha,and M.indica.M.oleifera had the largest seed(average 7.40 g single seed),highest oil content(58.71%),and highest NA level(42.22%).The germplasm diversity of M.oleifera is associated with its habitat but not elevation.Seeds of M.adenantha contained higher NA levels(28.41%)than M.indica(21.77%),but M.indica contained a significantly higher oil content(29.22%)and seed yield.M.adenantha germplasm varied among populations,with one population having seeds with high oil content(22.63%)and NA level(37.78%).Although M.indica grow naturally at a range of elevations,no significant differences were detected between M.indica populations.These results suggest that M.indica and M.oleifera have greater potential as a source of NA,which will contribute to constructing a germplasm resource nursery and establishing a selection and breeding program to improve the development of NA-enriched plants.展开更多
基金Supported by the Program for Greating Okinawa Innovation of Cabinet Office,Government of Japana Grant-in-Aid for Scientific Research of the Japan Society for the Promotion of Science
文摘Objective:To analyze the antioxidant prenylilavonoids in different parts of Macaranga tanarius(M.tanarius)(Euphorbiaceae)including the leaf,petiole,stem,leaflet,flower and fruit(only in female plant),and to evaluate their antioxidant properties.Methods:Methanol extracts of each part of M.tanarius were prepared and five prenylilavonoids in them were quantitatively analyzed using HPLC.The fruits from female plant were further separated into seed,pericarp,and glandular trichome.After the quantitative analyses of prenylflavonoids in each part of M.tanarius,antioxidant activity of the extracts was evaluated by 2,2-diphenyl-l-picryI-hydrazyl(DPPH)radical scavenging assay.Results:The leaf of M.tanarius contained two prenylflavonoids as main components in both male and female plants.Both flowers(male and female)contained five kinds of prenylflavonoids.In the petiole,stem and leaflet of both male and female plants,the prenylflavonoids were not delected or their amounts were very low.Five kinds of prenylflavonoids were detected in the seed,pericarp and glandular trichome of female M.tanarius.In particular,the glandular trichome had the highest level of total prenylflavonoids(235 mg/g of fresh plant).DPPH radical scavenging activity of all parts was more than 30%.Conclusions:We found that different parts of M.tanarius contained antioxidant prenylflavonoids.In particular,not only the glandular trichome but also the leaf contained prenylflavonoids,which indicated that M.tanarius may be developed as a functional plant,because the leaves of this plant can be easily collected.
基金National Natural Science Foundation of China(31300293 and 81422046)General Project of Applied Foundation Research,Yunnan Province(2013FB067)+1 种基金Basic Research Project of Ministry of Science and Technology of China(2012FY110300)Major State Basic Research Development Program(2010CB951704).
文摘Three new minor prenylated flavonoids,named macadenanthins A–C(1–3),together with three known ones(4–6),were isolated from the twigs of Macaranga adenantha.Their structures were elucidated on the basis of extensive spectroscopic analysis including NMR,UV and MS.The prenyl moieties in compounds 1–3 were further modified by cyclization and hydroxylation.The new compounds were tested for their cytotoxicity against four cancer cell lines(MCF-7,Hep G2,Hela and P388)and showed IC50 values in the range of 13.76–22.27 lM.
基金Financial support from the National Natural Science Foundation of China(Nos.81222045,21372049)the Specialized Research Fund for the Doctoral Program of Higher Education of China(20130071120104)the Shu Guang Project(No.12SG02)from Shanghai Municipal Education Commission and Shanghai Education Development Foundation is gratefully acknowledged.
文摘Three new C-methylated and isoprenylated chalcone derivatives,dentichalcones A–C(1–3),together with six known compounds(4–9),were isolated from the twigs and leaves of Macaranga denticulata.Their structures were elucidated by spectroscopic analysis,including 1D,2D NMR,and MS data.The known compounds,(2E)-1-(5,7-dihydroxy-2,2,6-trimethyl-2H-benzopyran-8-yl)-3-(4-methoxyphenyl)-2-propen-1-one(4),(2E)-1-(5,7-dihydroxy-2,2-dimethyl-2H-benzopyran-8-yl)-3-phenyl-2-propen-1-one(5),laxichalcone(6),macarangin(7),bonanniol A(8),and bonannione A(9),showed inhibitory activities against protein tyrosine phosphatase 1B(PTP1B)in vitro.Graphical Abstract Three new C-methylated and isoprenylated chalcone derivatives,dentichalcones A–C(1–3),together with six known compounds,were isolated from the twigs and leaves of Macaranga denticulata.Some compounds showed inhibitory activities against PTP1B in vitro.
基金the Directorate Research Development,UFS,South Africa for the Postdoctoral Fellow-ship granted Dr.A.L Ogundajo(Entity No.2114 B5004)tenable at the Phytomedicine and Phytopharmacology Research Unit,UFS,South Africa.
文摘Objectives: To investigate antimicrobial and cytotoxic potentials as well as chemical constituents of extracts from Macaranga barteri(M. barteri).Methods: Antimicrobial activity was carried out using micro-dilution, cell culture and GC–MS methods were employed to determine the cytotoxicity and chemical constituents of the extracts respectively.Results: Marked activity was observed in methanol(ME) fraction [MIC_(50):(0.097 7–6.250 0) mg/mL] compared to hexane and ethyl acetate fractions. Aeromonas hydrophila(environmental strain) and Shigella sonnei(ATCC 29930) were the most susceptible pathogens to ME and ciprofloxacin(Cl) at MIC_(50) value of 0.097 7 and < 0.019 5 mg/mL respectively. Cryptococcus neoformans(ATCC 66031) was susceptible to ME at 0.195 3 mg/mL compared to fluconazole at 10.000 0 mg/mL. Decreased viability of the Vero cells was observed at the concentrations of 0.1–1.0 mg/mL. The lethal dose(LC_(50))of hexane, ethyl acetate and methanol fractions were recorded at(0.30 ± 0.07),(0.52 ± 0.05) and(0.22 ± 0.04) mg/mL, respectively. Some of the compounds identified from ME were caryophyllene(25.21%), neophytadiene(11.90%), a-humulene(7.67%),phytol(4.40%), ethyl ester hexadecanoic acid(4.04%) and nerolidol(2.83%) which were known to have various antimicrobial activities.Conclusions: Methanol fraction of M. barteri is a potent and safe antimicrobial and antifungal alternative which can be useful in the search for new antimicrobial drugs. The study also confirmed the orthodox usage of M. barteri in combating infectious diseases.
基金supported by the National Natural Science Foundation of China(No.81860615,82260682)Project of Yunnan Characteristic Plant Screening and R&D Service CXO Platform(No.2022YKZY001).
文摘Objective:To study constituents of the leaves of Macaranga hemsleyana,and evaluate their inhibitory effects against NOD-like receptor thermal protein domain associated protein 3(NLRP3)inflammasome activation,and antiproliferative activity.Methods:The constituents were isolated and purified by column chromatography on MCI gel CHP20P/P120,silica gel,Sephadex LH-20,and HPLC.The structures of compounds were determined by 1D,2D NMR,and HR-ESI-MS data.The inhibitory effect of compounds on inflammasome activation was determined by lactate dehydrogenase(LDH)procedure.The antiproliferative activity was evaluated using MTT assay.Results:The study led to the isolation of 23 compounds,including one new compound,identified as(2Z)-3-[4-(β-D-glucopyranosyloxy)-2′-hydroxy-5′-methoxyphenyl]-2-propenoic acid(1),together with 22 known compounds recognized as 1,4-dihydro-4-oxo-3-pyridinecarbonitrile(2),methyl 4-methoxynicotinate(3),4-methoxynicotinonitrile(4),1-(3-O-β-D-glucopyranosyl-4,5-dihydroxyphenyl)-ethanone(5),neoisoastilbin(6),isoastilbin(7),aromadendrin(8),neoastilbin(9),astilbin(10),quercitrin(11),neoschaftoside(12),apigenin 6,8-bis-C-α-L-arabinoside(13),vitexin(14),bergenin(15),scopoletin(16),glucopyranoside salicyl(17),koaburside(18),benzylβ-D-glucoside(19),icariside B5(20),roseoside(21),loliolide(22),and adenosine(23).The tested compounds did not show LDH inhibition nor antiproliferative activity.Conclusion:Compound 1 was a new glycoside.Compounds 2 and 3 were obtained for the first time from natural source.The 22 known compounds constituted of alkaloids(2–4,23),phenolics(5,15,17,18),flavonoids(6–14),coumarin(16),benzyl glycoside(19),and norsesquiterpenes(20–22).All the compounds,1–23,were revealed from M.hemsleyana for the first time.This is the initial uncovering of molecules 1–10,12,13,17–19,and 23 from the genus Macaranga.The isolated compounds,11,14–16,and 20–22 established taxonomic classification of M.hemsleyana in Euphorbiaceae family.Flavonoids were outstanding as chemosystematic markers of Macaranga genus.
基金supported by the Applied Basic Research Key Project of Yunnan,China(Grant No.202101AS07001)Reserve Talents for Yunnan Young and Middle-aged Academic and Technical Leaders,China(Grant No.202105AC160083)National Natural Science Foundation of China(Grant No.31671732).
文摘Nervonic acid(NA)is a very-long-chain monounsaturated fatty acid with pharmaceutical and nutraceutical functions that plays an important role in treating several neurological disorders.One major source of NA is plant seed oil.Here we report fatty acid profiles of seeds and germplasm diversity of six plant species,including three woody plants with high amounts of NA-enriched seed oil,Malania oleifera,Macaranga adenantha,and M.indica.M.oleifera had the largest seed(average 7.40 g single seed),highest oil content(58.71%),and highest NA level(42.22%).The germplasm diversity of M.oleifera is associated with its habitat but not elevation.Seeds of M.adenantha contained higher NA levels(28.41%)than M.indica(21.77%),but M.indica contained a significantly higher oil content(29.22%)and seed yield.M.adenantha germplasm varied among populations,with one population having seeds with high oil content(22.63%)and NA level(37.78%).Although M.indica grow naturally at a range of elevations,no significant differences were detected between M.indica populations.These results suggest that M.indica and M.oleifera have greater potential as a source of NA,which will contribute to constructing a germplasm resource nursery and establishing a selection and breeding program to improve the development of NA-enriched plants.
