A catalytic diastereoselective Prins reaction for hydroxymethylation and hydroxylation of 1,3-diarylpropene was successfully utilized to prepare various 1,3-dioxanes7 in 14-88%yields.Take advantage of the synthetic in...A catalytic diastereoselective Prins reaction for hydroxymethylation and hydroxylation of 1,3-diarylpropene was successfully utilized to prepare various 1,3-dioxanes7 in 14-88%yields.Take advantage of the synthetic intermediate7h,the key B/C rings in brazilin core could be constructed by the sequential of Friedel-Crafts/Ullmann-Ma rather than Ullmann-Ma/Friedel-Crafts reactions.展开更多
Caesalpinia sappan L.(CS) is a plant of Leguminosae family,commonly known as Brazil or Sappan wood.CS is distributed in Southeast Asia and its dried heartwood has been used as traditional ingredient of food or beverag...Caesalpinia sappan L.(CS) is a plant of Leguminosae family,commonly known as Brazil or Sappan wood.CS is distributed in Southeast Asia and its dried heartwood has been used as traditional ingredient of food or beverages and has a wide variety of medicinal properties.Higher extraction yield of CS wood was achieved with 95% ethanol for 2 h.Chemical constituent's investigation of sappan wood resulled in the isolation of various structural types of phenolic components including one xanihone,one coumarin,three chalcones,two flavones three homoisoflavonoids and brazilin.Brazilin[(6a S-cis)-7,11b-dihydrobcnz[b]indeno[1.2-d]pyran-3.6a.9.10(6H)- tetroll.a major and active compound found in CS heartwood.Most of the folkloric uses of brazilin were validated by the scientific studies such as antioxidant,antibacterial,anti-inflammatory,anti-photoaging.hypoglycemic,vasorelaxant,hepatoproteetive and anti-acne activity.CS heartwood extract is safe and did not produce any acute or subacute toxicity in both male and female rats.Brazilin is the safe natural compound having potential to develop as a medicinal compound with application in food,beverage,cosmetics and pharmaceutical industries to screen its clinical use in modern medicine.The information gained could provide the important and potential approach for pharmaceutical researcher to implicate the knowledge of brazilin in the formulation of new drug and to reveal therapeutic and gaps requiring future research opportunities.More studies are needed to evaluate the potential application of brazilin as preservative and coloring agent in food processing industries.展开更多
Caesalpinia sappan L., belonging to the family Leguminosae, is a medicinal plant that is distributed in Southeast Asia. The dried heartwood of this plant is used as a traditional ingredient of food, red dyes, and folk...Caesalpinia sappan L., belonging to the family Leguminosae, is a medicinal plant that is distributed in Southeast Asia. The dried heartwood of this plant is used as a traditional ingredient of food, red dyes, and folk medicines in the treatment of diarrhea, dysentery, tuberculosis, skin infections, and inflammation. Brazilin is the major active compound, which has exhibited various phar- macological effects, including anti-platelet activity, anti-hepatotoxicity, induction of immunological tolerance, and anti-inflammatory and antioxidant activities. The present study aimed to evaluate the antioxidant activity and expression of antioxidant enzymes of C. sappan L. extract and its major compound, brazilin, in human epidermal keratinocytes exposed to UVA irradiation. Our results indi- cated that C. sappan L. extract reduced UVA-induced H202 production via GPX7 activation. Moreover, brazilin exhibited anfioxidant effects that were similar to those of C. sappan L. via glutathione peroxidase 7 （GPX7）, suggesting that C. sappan L. extract and its natural compound represent potential treatments for oxidative stress-induced photoaging of skin.展开更多
Objective: The objective of the work was to optimize the extraction conditions of Caesalpinia sappan L.heartwood in order to maximize the brazilin content and antibacterial activity of the extract.Methods: Two indepen...Objective: The objective of the work was to optimize the extraction conditions of Caesalpinia sappan L.heartwood in order to maximize the brazilin content and antibacterial activity of the extract.Methods: Two independent factors were studied: extraction temperature(45–95 °C) and extraction time(30–60 min). In addition, five dependent factors were monitored, including extraction yield, brazilin content, and clear zones against Staphylococcus aureus TISTR 1466, Staphylococcus epidermidis TISTR 518 and Propionibacterium acnes DMST 14961. The brazilin content was quantified by high-performance liquid chromatography and antibacterial activity was determined by disk diffusion assay.Results: The high temperature provided high total extract yield as well as brazilin content, while extraction time had little effect on yield or brazilin content. Extraction time had a positive effect, while extraction temperature had little effect on clear zone against S. aureus. The largest clear zone against S. epidermidis was achieved at low extraction temperature and long extraction time. Conversely, short extraction time and high extraction temperature provided the largest clear zone against P. acnes. The optimal conditions providing the highest brazilin content was an extraction temperature and extraction time of 95 °C and 30 min, respectively.The same optimal conditions also provided the simultaneous greatest antibacterial activity against the three bacteria. Modeled optimal conditions were validated be conducting extraction using these values. Yield and antibacterial activity of the resulting extract demonstrated that the model had a low percentage error.Conclusion: The optimal condition will be used as a standard condition for extraction of C. sappan heartwood to maximize brazilin content and antibacterial activity.展开更多
Determination of brazilin by High Performance Liquid Chromatography （HPLC） method and measurement of the antioxidative and lipase inhibition effects in the Caesalpinia sappan wood from various locations in Indonesia...Determination of brazilin by High Performance Liquid Chromatography （HPLC） method and measurement of the antioxidative and lipase inhibition effects in the Caesalpinia sappan wood from various locations in Indonesia is described in this paper. Brazilin was separated from sample matrix using a reversed phase C 18, Shim-pack VP column with the mobile phase in a gradient elution for45 min from 5% to 100% methanol in 0.05% aqueous trifluoroacetic acid. Brazilin in ethanolic extracts ofC. sappan wood was in the range of 5.81 to 24.85 mg/g on dry-weight basis. Antioxidant and lipase inhibition activities expressed by IC50 values from all samples were in the range from 6.60 to 11.53 μg/mL and 50.76 to 203.21 μg/mL, respectively. Antioxidative and lipase inhibition potency of all ethanolic extracts were compared to vitamin C and chloramphenicol, isopropyl methylphenol and tetracyclin, respectively.展开更多
Objective:To investigate the mechanism of induction of ferroptosis by brazilin in breast cancer cells.Methods:Breast cancer 4T1 cells were divided into 6 groups:control,brazilin 1/2 half maximal inhibitory concentrati...Objective:To investigate the mechanism of induction of ferroptosis by brazilin in breast cancer cells.Methods:Breast cancer 4T1 cells were divided into 6 groups:control,brazilin 1/2 half maximal inhibitory concentration(IC_(50)),IC_(50),2×IC_(50),erastin(10μg/mL)and capecitabine(10μg/mL)groups.The effect of brazilin on the proliferation of 4T1 cells was detected by cell counting kit-8 assay,and the treatment dose of brazilin was screened.The effect of brazilin on the mitochondrial morphology of 4T1 cells,and the mitochondrial damage was evaluated under electron microscopy.The levels of Fe+,reactive oxygen species(ROS),malondialdehyde(MDA),glutathione(GSH)and glutathione peroxidase 4(GPX4)were estimated using various detection kits.The invasion and migration abilities of 4T1 cells were detected by scratch assay and transwell assay.The expressions levels of tumor protein p53,solute carrier family 7 member 11(SLC7A11),GPX4 and acyl-CoA synthetase long-chain family member 4(ACSL4)proteins were quantified by Western blot assay.Results:Compared to the control group,the 10(1/2 IC_(50)),20(IC_(50))and 40(2×IC_(50))μg/mL brazilin,erastin,and capecitabine groups showed a significant decrease in the cell survival rate,invasion and migration abilities,GSH,SLC7A11 and GPX4 protein expression levels,and mitochondrial volume and ridge(P<0.05),and a significant increase in the mitochondria membrane density,Fe2+,ROS and MDA levels,and p53 and ACSL4 protein expression levels(P<0.05).Conclusions:Brazilin actuated ferroptosis in breast cancer cells,and the underlying mechanism is mainly associated with the p53/SLC7A11/GPX4 signaling pathway.展开更多
基金support from National Natural Science Foundation of China(82260683 and 22267024)Scientific and Technological Project of Yunnan Precious Metals Laboratory(YPML-2023050265 and YPML-2023050217)+3 种基金Yunnan Science and Technology Talent and Platform Program(202105AG070012)the Top Young Talent of Ten Thousand Talents Program of Yunnan Province(D.L.and L.-D.S.)the Start-up Fund of Yunnan University of Chinese Medicine(2019YZG03)the Bioactive Ethnopharmacol Molecules Chemical Conversion and Application Innovation Team of Department of Education of Yunnan Province(2022).
文摘A catalytic diastereoselective Prins reaction for hydroxymethylation and hydroxylation of 1,3-diarylpropene was successfully utilized to prepare various 1,3-dioxanes7 in 14-88%yields.Take advantage of the synthetic intermediate7h,the key B/C rings in brazilin core could be constructed by the sequential of Friedel-Crafts/Ullmann-Ma rather than Ullmann-Ma/Friedel-Crafts reactions.
文摘Caesalpinia sappan L.(CS) is a plant of Leguminosae family,commonly known as Brazil or Sappan wood.CS is distributed in Southeast Asia and its dried heartwood has been used as traditional ingredient of food or beverages and has a wide variety of medicinal properties.Higher extraction yield of CS wood was achieved with 95% ethanol for 2 h.Chemical constituent's investigation of sappan wood resulled in the isolation of various structural types of phenolic components including one xanihone,one coumarin,three chalcones,two flavones three homoisoflavonoids and brazilin.Brazilin[(6a S-cis)-7,11b-dihydrobcnz[b]indeno[1.2-d]pyran-3.6a.9.10(6H)- tetroll.a major and active compound found in CS heartwood.Most of the folkloric uses of brazilin were validated by the scientific studies such as antioxidant,antibacterial,anti-inflammatory,anti-photoaging.hypoglycemic,vasorelaxant,hepatoproteetive and anti-acne activity.CS heartwood extract is safe and did not produce any acute or subacute toxicity in both male and female rats.Brazilin is the safe natural compound having potential to develop as a medicinal compound with application in food,beverage,cosmetics and pharmaceutical industries to screen its clinical use in modern medicine.The information gained could provide the important and potential approach for pharmaceutical researcher to implicate the knowledge of brazilin in the formulation of new drug and to reveal therapeutic and gaps requiring future research opportunities.More studies are needed to evaluate the potential application of brazilin as preservative and coloring agent in food processing industries.
基金supported by the Technological Innovation R&D Program(No.S2443581)funded by the Small and Medium Business Administration(SMBA,Korea)
文摘Caesalpinia sappan L., belonging to the family Leguminosae, is a medicinal plant that is distributed in Southeast Asia. The dried heartwood of this plant is used as a traditional ingredient of food, red dyes, and folk medicines in the treatment of diarrhea, dysentery, tuberculosis, skin infections, and inflammation. Brazilin is the major active compound, which has exhibited various phar- macological effects, including anti-platelet activity, anti-hepatotoxicity, induction of immunological tolerance, and anti-inflammatory and antioxidant activities. The present study aimed to evaluate the antioxidant activity and expression of antioxidant enzymes of C. sappan L. extract and its major compound, brazilin, in human epidermal keratinocytes exposed to UVA irradiation. Our results indi- cated that C. sappan L. extract reduced UVA-induced H202 production via GPX7 activation. Moreover, brazilin exhibited anfioxidant effects that were similar to those of C. sappan L. via glutathione peroxidase 7 （GPX7）, suggesting that C. sappan L. extract and its natural compound represent potential treatments for oxidative stress-induced photoaging of skin.
基金the Research Institute of Rangsit University for financial support (Grant No. 14/2560)
文摘Objective: The objective of the work was to optimize the extraction conditions of Caesalpinia sappan L.heartwood in order to maximize the brazilin content and antibacterial activity of the extract.Methods: Two independent factors were studied: extraction temperature(45–95 °C) and extraction time(30–60 min). In addition, five dependent factors were monitored, including extraction yield, brazilin content, and clear zones against Staphylococcus aureus TISTR 1466, Staphylococcus epidermidis TISTR 518 and Propionibacterium acnes DMST 14961. The brazilin content was quantified by high-performance liquid chromatography and antibacterial activity was determined by disk diffusion assay.Results: The high temperature provided high total extract yield as well as brazilin content, while extraction time had little effect on yield or brazilin content. Extraction time had a positive effect, while extraction temperature had little effect on clear zone against S. aureus. The largest clear zone against S. epidermidis was achieved at low extraction temperature and long extraction time. Conversely, short extraction time and high extraction temperature provided the largest clear zone against P. acnes. The optimal conditions providing the highest brazilin content was an extraction temperature and extraction time of 95 °C and 30 min, respectively.The same optimal conditions also provided the simultaneous greatest antibacterial activity against the three bacteria. Modeled optimal conditions were validated be conducting extraction using these values. Yield and antibacterial activity of the resulting extract demonstrated that the model had a low percentage error.Conclusion: The optimal condition will be used as a standard condition for extraction of C. sappan heartwood to maximize brazilin content and antibacterial activity.
文摘Determination of brazilin by High Performance Liquid Chromatography （HPLC） method and measurement of the antioxidative and lipase inhibition effects in the Caesalpinia sappan wood from various locations in Indonesia is described in this paper. Brazilin was separated from sample matrix using a reversed phase C 18, Shim-pack VP column with the mobile phase in a gradient elution for45 min from 5% to 100% methanol in 0.05% aqueous trifluoroacetic acid. Brazilin in ethanolic extracts ofC. sappan wood was in the range of 5.81 to 24.85 mg/g on dry-weight basis. Antioxidant and lipase inhibition activities expressed by IC50 values from all samples were in the range from 6.60 to 11.53 μg/mL and 50.76 to 203.21 μg/mL, respectively. Antioxidative and lipase inhibition potency of all ethanolic extracts were compared to vitamin C and chloramphenicol, isopropyl methylphenol and tetracyclin, respectively.
基金Supported by National Administration of Traditional Chinese Medicine Youth Qihuang Scholars Talent Project,the 73rd Batch of Grant from China Postdoctoral Science Foundation(No.2023M731069)Traditional Chinese Medicine Administration Project of Hunan Province(No.B2023086)Health Research Project of Hunan Provincial Health Commission(No.W20243081)。
文摘Objective:To investigate the mechanism of induction of ferroptosis by brazilin in breast cancer cells.Methods:Breast cancer 4T1 cells were divided into 6 groups:control,brazilin 1/2 half maximal inhibitory concentration(IC_(50)),IC_(50),2×IC_(50),erastin(10μg/mL)and capecitabine(10μg/mL)groups.The effect of brazilin on the proliferation of 4T1 cells was detected by cell counting kit-8 assay,and the treatment dose of brazilin was screened.The effect of brazilin on the mitochondrial morphology of 4T1 cells,and the mitochondrial damage was evaluated under electron microscopy.The levels of Fe+,reactive oxygen species(ROS),malondialdehyde(MDA),glutathione(GSH)and glutathione peroxidase 4(GPX4)were estimated using various detection kits.The invasion and migration abilities of 4T1 cells were detected by scratch assay and transwell assay.The expressions levels of tumor protein p53,solute carrier family 7 member 11(SLC7A11),GPX4 and acyl-CoA synthetase long-chain family member 4(ACSL4)proteins were quantified by Western blot assay.Results:Compared to the control group,the 10(1/2 IC_(50)),20(IC_(50))and 40(2×IC_(50))μg/mL brazilin,erastin,and capecitabine groups showed a significant decrease in the cell survival rate,invasion and migration abilities,GSH,SLC7A11 and GPX4 protein expression levels,and mitochondrial volume and ridge(P<0.05),and a significant increase in the mitochondria membrane density,Fe2+,ROS and MDA levels,and p53 and ACSL4 protein expression levels(P<0.05).Conclusions:Brazilin actuated ferroptosis in breast cancer cells,and the underlying mechanism is mainly associated with the p53/SLC7A11/GPX4 signaling pathway.
