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

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.

Antioxidant Activity In Vitro of Three Constituents from Caesalpinia sappan L

Antioxidant activities of the 95% ethanol extract from Caesalpinia sappan heartwood （ECS）, protosappanin A, protosappanin B, and brazilein were studied in vitro. The inhibition of the formation of malondialdehyde （MDA） and the scavenging of superoxide anions, hydrogen peroxide, and hydroxyl radicals were assayed. The experimental results show that all four substances had antioxidant activity in vitro but their capabilities differed for the different indicators. ECS, protosappanin A, and protosappanin B show more inhibition of MDA and scavenging of hydrogen peroxide, while brazilein shows more scavenging of hydroxyl radicals. All the samples show little scavenging of superoxide anions.

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

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.

Rearranged diterpenoids from the seeds of Caesalpinia sappan

Two new rearranged diterpenoids, tomocinol C （1） and spirocaesalmin C （2） were isolated from the seeds of Caesalpinia sappan. Their structures were elucidated based on comprehensive analysis of spectroscopic data, and their absolute configurations were established by single crystal X-ray crystallography.

Cytotoxic cassane diterpenoids from the seeds of Caesalpinia sappan

Phytochemical investigation on the seeds of Caesalpinia sappan led to the isolation of five new cassanetype diterpenoids, named 11-oxo-phanginin A（1）, caesalsappanins O–Q（2–4） and phanginin U（5）,together with five known compounds. The structures of the new compounds were elucidated by extensive analysis of mass spectrometric and 1D and 2D NMR spectroscopic data. All the new compounds showed moderate cytotoxic effects on human breast cancer MCF-7 and human colon cancer HCT116 cell lines.

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

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.

Chemical constituents from heartwoods of Caesalpinia sappan with antiplatelet aggregation activities

Objective:To clarify the active constituents of the heartwoods of Caesalpinia sappan,a traditional Chinese medicine with the functions of promoting blood circulation(Huoxue in Chinese)and removing blood stasis(Quyu in Chinese).Methods:The chemical constituents were isolated and purified by combination of silica gel and Sephadex LH-20 column chromatography,along with semipreparative HPLC.Their chemical structures were established by multiple spectroscopic methods and comparison with literature data.The in vitro antiplatelet aggregation activities were evaluated using mouse platelet induced by AYPGKF-NH2,a gold agonist of protease-activated receptor 4(PAR4).Results:Two new phenols,methyl 2-(4,4’,5’-trihydroxy-2’-(methoxymethyl)biphenyl-2-yloxy)acetate(1)and 1’-methylcaesalpin J(2),together with 24 known compounds(3-26),were isolated from the heartwoods of C.sappan.Among them,sappanchalcone(16)and brazilin(20)showed inhibitory activities against mouse platelet aggregation with IC50 values of 114.8μmol/L and 100.8μmol/L,respectively.Conclusion:Antiplatelet compounds from C.sappan targeting at PAR4 are reported for the first time.

Chemical constituents from Sappan Lignum

To study the chemical constituents of Sappan Lignum. Chemical constituents were isolated by method of solvent extraction, repeated chromatography with silica gel, Sephadex LH-20, and ODS. The structures were elucidated based on spectro- scopic data. Fourteen compounds were isolated and their structures were identified as brazilin （1）, sappanone B （2）, （E）-3-（3,4- dihydroxybenzylidene）-7-hydroxychroman-4-one （3）, 3-deoxysappanone B （4）, brazilide A （5）, euxanthone （6）, quercetin （7）, rhamnetin （8）, sappanchalcone （9）, 3-deoxysappanchalcone （10）, butein （11）, 2,4,5-trihydroxybenzaldehyde （12）, 3,8,9-trihydroxy- 6H-benzo[c]chromen-6-one （13） and 13-sitosterol （14）. Compounds 12 and 13 were two new natural compounds, and the ^13C NMR data of compound 13 were reported for the first time. Compound 6 was the first xanthone isolated from the genus Caesalpinia.

Identification of Xunxi Shujin Decoction by TLC

[Objectives]To establish a TLC qualitative method for the determination of Radix Aconiti,Radix Aconiti Kusnezoffii,Caesalpinia sappan L.and Radix zanthoxyli.[Methods]TLC was used to study the quality of Radix Aconiti,Radix Aconiti Kusnezoffii and C.sappan L.in Xunxi Shujin Decoction,and the influencing factors were investigated to optimize the TLC conditions.[Results]In the TLC identification test of Radix Aconiti,Radix Aconiti Kusnezoffii,C.sappan L.and R.zanthoxyli in Xunxi Shujin Decoction,the spots were clear,the resolution was good,the specific value was moderate,the negative control was not disturbed,and the specificity was strong.[Conclusions]The established TLC method was simple,specific and reproducible,and could be used for the quality control of Xunxi Shujin Decoction.

苏木有效成分抗动脉粥样硬化的实验研究进展

中药苏木性平,味甘、咸,归心、肝、脾经,具有活血祛瘀、消肿止痛的功效。药理研究发现苏木有效成分可大致分为巴西苏木素类、原苏木素、高异黄酮、查尔酮类等,具有降血脂、抗炎、抗氧化、抑制血管平滑肌细胞增殖和凋亡、抗血栓形成及扩张血管等作用。基于动脉粥样硬化是导致心血管疾病的病理基础,且具有明显的病理分期,因此本文就近年来苏木在动脉粥样硬化进程中各时期作用机制的实验研究进行归纳总结,以期为及早防治动脉粥样硬化及心血管疾病提供参考。

Brazilin Content, Antioxidative and Lipase Inhibition Effects of Sappanwood （Caesa/pinia Sappan） from 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.

天然药物苏木对人工脱矿釉质龋的再矿化作用

目的 观察苏木乙醇提取物、乙酸乙酯、正丁醇、水萃取部位对人工脱矿釉质龋的作用。方法 将牛切牙制成人工脱矿釉质龋后,测定苏木乙醇提取物和不同萃取部位对牛切牙釉质表面显微硬度的影响,扫描电镜观察各实验组对釉质龋表面形态的影响。结果 乙醇提取物和各萃取部位都有提高釉质龋表面硬度的作用,其中水萃取部位对釉质硬度恢复效果最好,硬度恢复率达到66.9%(P <0.05)。扫描电镜观察到各实验组的釉质龋表面覆盖有大量颗粒状沉积物。结论 苏木乙醇提取物及各萃取部位对人工脱矿釉质龋均有再矿化作用。

中药苏木提取物诱导K562细胞凋亡的研究

目的:探讨中药苏木提取物诱导人类慢性髓性白血病K562细胞株的凋亡作用。方法:采用MTT法检测苏木提取物对K562细胞增殖抑制作用;荧光显微镜观察细胞形态变化;库尔特全自动颗粒粒度分析药物引起K562细胞体积大小的分布变化;琼脂糖凝胶电泳测定DNAladder及流式细胞术检测细胞周期变化。结果:25μg/ml苏木浸膏能明显诱导K562细胞凋亡,产生凋亡细胞所具有的典型形态学及生化学特征,同时对K562细胞的增殖抑制和诱导凋亡作用呈一定的浓度依赖性。结论:中药苏木提取物能诱导细胞凋亡,抑制癌细胞增殖呈一定的浓度依赖关系。

苏木有效成分对大鼠免疫活性细胞的影响

目的 探讨苏木提纯物的免疫抑制活性及其对IL - 2生成的影响。方法 不同成分、不同剂量的苏木提纯物大鼠灌胃 7d后 ,取脾及腹腔液测定大鼠的T淋转、B淋转、M和Nk细胞的活性 ,并检测混合淋巴细胞培养上清液中IL - 2的水平。结果 苏木水提物大剂量组可明显抑制T淋转功能 ,但各剂量组均不影响B淋转功能、Nk细胞的活性及M细胞的活性。苏木醇提物中剂量组及大剂量组均可影响T淋转功能 ,苏木醇提物大剂量组可影响B淋转功能 ,且苏木醇提物中剂量组及大剂量组还可影响M细胞的活性 ,对Nk细胞的活性没有影响。苏木酯提物小剂量组对Nk细胞的活性有影响 ,中、大剂量组对M细胞的活性有影响 ,对Nk细胞的活性亦有影响。苏木醇提物大剂量组和苏木水提物大剂量组可减少混合淋巴细胞培养上清液中的IL - 2的生成。结论 苏木不同成分有不同的免疫抑制功能 。

苏木水提物抗心脏移植急性排斥反应的实验研究

目的 探讨苏木水提物对心脏移植排斥反应的抑制作用。方法 应用大鼠腹腔同种异位心脏移植模型。受体雄性SD大鼠 ,供体雄性Wistar大鼠 ,分为苏木大、中、小剂量组 ,环孢A(CsA)组 ,苏木加半量CsA组 ,对照组。术前 2d给药 ,术后第 3、5天抽血检测IL - 2 ,观察术后移植心脏的存活天数及心脏跳动情况。结果 苏木大剂量组及苏木加半量CsA组供心存活时间均较对照组明显延长 (P <0 0 5 ) ,心肌病理学损害较轻 ,与对照组相比血清IL - 2水平明显下降 (P <0 0 5 )。结论 苏木有较强的免疫抑制作用 ,可明显延长同种异体移植物的存活天数 ,减少CsA的用量。

苏木不同提取物行血祛瘀活性研究

苏木（CaesalpiniasappanL．）为豆科云实属植物，始载于《唐本草》，味甘、成、性平，其干燥心材为传统中药材，具有舒筋通络、活血散结、镇静、祛痰、止痛等功效。近年来，关于苏木提取物的活性研究主要集中在抗肿瘤和免疫抑制”。方面，尤其在抗器官移植排斥反应方面的报道较多，而对于苏木的传统功效，行血祛瘀及消肿止痛方面的药理研究和报道均很少。本研究通过考察苏木不同提取物对急性血瘀模型大鼠全血黏度、血小板聚集的影响，探讨其行血祛瘀药理活性及机制。

苏木的化学成分研究(英文)

从苏木(Caesalpinia sappan)心材的乙醇提取物中分离得到了9个化合物,经波谱分析,鉴定结构为氧化巴西木素(1)、巴西木素(2)、(±)-lyoniresinol(3)、十八酸(4)、豆甾醇(5)、(E)-3,3′-dimethoxy-4,4′-dihydrox-ystilbene(6)、(-)-丁香树脂酚(7)、原苏木素A(8)和brazilide(9)。其中化合物3、6和7为首次从该属植物中分离得到。

苏木化学成分的研究(Ⅰ)

从苏木（Caesalpinia sappan L.）70%乙醇提取物分离得到了8个化合物,利用现代波谱学方法鉴定其结构分别为5,7-二羟基-4′-甲氧基二氢异黄酮（1）,鹰嘴豆芽素A（2）,3,7,3′,4′-Tetrahydroxyflavanone（3）,（αR）-α,3,4,2′,4′-Pentahydroxydihydrochalcone（4）,Sappanone B（5）,7,3′,4′？三羟基二氢异黄酮（6）,7,3′,4′？三羟基二氢黄酮（7）,7,3′,4′-三羟基异黄酮（8）。其中化合物1~4、6~8为首次从该属植物中分得的。

施用沼液浓度对苏木苗期生长的影响

【目的】探讨苏木苗期沼液适宜的施用浓度,为沼肥在林业树种上的应用提供参考。【方法】通过单因素完全随机区组试验,研究施用不同稀释浓度(农灌水与沼液稀释比例分别为3∶1、1∶1、1∶3)沼液对苏木苗生长的影响。【结果】苏木苗生长随着沼液浓度不同表现出较大差异,稀释比例为1∶1时苏木苗苗高、地径显著高于其他处理。不同浓度的沼液对苏木苗生物量指标影响显著,其中稀释比例为1∶1处理苏木苗根鲜重、地上鲜重、根干重、地上干重高于对照。苏木苗苗木质量指数随沼液浓度变化表现出差异,稀释比例为1∶1处理苗木质量指数为5.49,显著高于对照。【结论】苏木苗期施用沼液能有效促进苗木生长,施用时需要做稀释处理,稀释比例为1∶1效果最佳。

苏木提取物对心脏移植大鼠T淋巴细胞亚群的免疫抑制和对心肌的保护作用

目的 探讨苏木不同提取物对心脏移植后大鼠T淋巴细胞亚群的免疫抑制和对心肌的保护作用。方法 应用大鼠腹腔同种异位心脏移植模型。受体来源于SD大鼠,供体Wistar大鼠。实验分为苏木醇提物组,苏木酯提物组、苏木水提物组、心脏移植组、对照组。术前2天给药,术后第7天采血,应用流式细胞仪检测外周血T淋巴细胞亚群的变化,并检测心肌组织的病理改变。结果 苏木醇提物及水提物可抑制大鼠心脏移植后外周血CD4+／CD8+的升高,并可减轻心脏移植后急性排斥反应所引起的心肌病理损害。结论在苏木的不同提取物中,苏木醇提物和水提物对心脏移植后发生的急性免疫排斥反应有明显的抑制作用,对心肌有明显的保护作用。