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brazilin and Caesalpinia sappan L. extract protect epidermal keratinocytes from oxidative stress by inducing the expression of GPX7

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Chinese Journal of Natural Medicines 2018年第3期16卷 203-209页

作者： Hyung Seo Hwang Joong Hyun Shim Department of Oriental Cosmetic Science Semyung University

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 pharmacological 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 indicated that C. sappan L. extract reduced UVA-induced H2 O2 production via GPX7 activation. Moreover, brazilin exhibited antioxidant 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.

关键词： Caesalpinia sappan L. brazilin 紫外 GPX7 抗氧化

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Optimization of Caesalpinia sappan L. heartwood extraction procedure to obtain the highest content of brazilin and greatest antibacterial activity

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Journal of Integrative Medicine 2019年第5期17卷 351-358页

作者： Sukanya Settharaksa Chaowalit Monton Laksana Charoenchai Drug and Herbal Product Research and Development Center College of Pharmacy Rangsit University

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.

关键词： Antibacterial activity brazilin Caesalpinia sappan Optimization

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brazilin from Caesalpinia sappan heartwood and its pharmacological activities:A review

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Asian Pacific Journal of Tropical Medicine 2015年第6期8卷 421-430页

作者： Nilesh P Nirmal Mithun S Rajput Rangabhatla G.S.V.Prasad Mehraj Ahmad Center for Nutrition and Food Sciences Queensland Alliance for Agriculture and Food InnovationUniversity of QueenslandHealth and Food Sciences PrecinctBlock 1039 Kessels RoadCoopers PlainsAcheifield Brisbane QLD 4108Australia Department of Medical Biochemistry.MGM Medical College Biomedical and Pharmaceutical Technology Research Group Nano Research for Advanced Materials Institute of Nutrition.Mahidol University 999 Phutthamonthon 4 Rd.SalayaNakhon Pathom-73170Thailand

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.

关键词： brazilin Caesalpinia sappan Extraction Heartwood Pharamcological activities

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brazilin类似物的合成

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化学学报 2012年第2期70卷 183-189页

作者：潘成学关一富张洪彬广西师范大学化学化工学院药用资源化学与药物分子工程国家重点实验室培育基地桂林541004 云南大学化学科学与工程学院教育部自然资源药物化学重点实验室昆明650091

以3-(3,4-二甲氧苯基)丙酸为原料,经分子内傅-克反应、双羟基化、Lombardo反应,高价碘的氧化及类Pinacol重排等共10步反应,完成了brazilin类似物的合成.

关键词： brazilin 天然产物类似物合成

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（+）和（-）-brazilin的对映选择性全合成研究

（+）和（-）-Brazilin的对映选择性全合成研究

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作者：欧文涛江西科技师范大学

学位级别：硕士

brazilin是传统药材苏木(Caesalpinia sappan)主要的活性成分,也是巴西木素类天然产物中的代表性成员之一,其四环骨架也代表了巴西木素类天然产物分子基本骨架结构。本论文以(+)和(-)-brazilin的对映选择性全合成为研究目标,来设计一条... 详细信息

brazilin是传统药材苏木(Caesalpinia sappan)主要的活性成分,也是巴西木素类天然产物中的代表性成员之一,其四环骨架也代表了巴西木素类天然产物分子基本骨架结构。本论文以(+)和(-)-brazilin的对映选择性全合成为研究目标,来设计一条简洁高效、新颖独特、选择性较高的全合成研究路线。基于(+)和(-)-brazilin独特的化学结构,本论文设计的合成路线主要以构建四环骨架中的茚环和吡喃环和引入季碳手性中心为研究重点。该路线以2-(溴甲基)丙烯酸甲酯为起始原料,通过Mitsunobu醚化反应来连接两个芳环;利用Sharpless不对称双羟基化反应,通过加入不同手性配体,引入季碳手性中心,得到两种构型的邻二醇;在三氟乙酸(TFA)催化下发生分子内Prins/Friedel-Crafts反应,串联一锅法来构建关键的茚环并吡喃环骨架结构,最后经脱甲醚保护,实现了目标化合物(+)和(-)-brazilin的对映选择性的全合成研究。本论文利用了分子内串联Prins/Friedel-Crafts反应,作为关键步骤来构建茚环吡喃环骨架结构,这缩短了合成路线,提高了原子利用率,更加绿色环保,同时也为巴西木素类家族化合物结构骨架构建提供了借鉴。

关键词：天然产物全合成 brazilin Prins/Friedel-Crafts反应

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Application of a liquid chromatography–tandem mass spectrometry method to the pharmacokinetics, tissue distribution and excretion studies of brazilin in rats

Application of a liquid chromatography–tandem mass spectrom...

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2013年中国药学大会暨第十三届中国药师周

作者： Ying Song Hujun Wang Likun Ding Xueqing Li Fang Dou Chengtao Lu Ningjuan Chi Yi Ding Yanyan Jia Aidong Wen Department of Pharmacy Xijing Hospital Fourth Military Medical University Department of Clinical Pharmacology General Hospital of Beijing Military Command of PLA

brazilin is an important constituent of Caesalpinia sappan L., and has several bioactivities. In this study, a rapid and sensitive analytical method based on high-performance liquid chromatography–tandem mass spectrometry （HPLC–MS/MS） has been developed for the determination of brazilin in rat plasma, urine, feces and tissues （brain, heart, liver, lung and kidney and spleen）. Biological samples were processed with ethyl acetate containing 5% formic acid extraction, and salicylic acid （SA） was chosen as the internal standard （IS）. The separation of brazilin was achieved on an Inspire C 18 column （4.6 mm×150 mm, 5 μm） with a mobile phase consisting of methanol / 5 mM ammonium acetate （80:20, v/v）. The MS/MS detection was carried out by monitoring the fragmentation of m/z 285.1→163.0 for brazilin and m/z 137.1→93.1 for SA on a triple quadrupole mass spectrometer. The total run time was only 5.0 min. The analyte showed good linearity over a wide concentration range （R2 ＞ 0.995） and its lower limit of quantification was 2 ng/mL. The accuracy and precision ranged from 97.1 to 103.3% and 1.7 to 9.1%, respectively. Recoveries （78.9–93.8%） and matrix effects （81.0-97.8%） were satisfactory in all the biological matrices examined. Stability studies （86.4–99.8%） showed that brazilin was stable during the assay procedure and long-term storage. The assay was successfully applied to plasma pharmacokinetics, tissue distribution and excretion study of rats. The pharmacokinetic parameters, such as half-life, mean residence time, maximum concentration were determined. These preclinical data of brazilin would be useful for the clinical reference.

关键词： brazilin LC-MS/MS pharmacokinetics tissue distribution excretion

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