A new homoisoflavan from Caesalpinia sappan

A new homoisoflavan, 7,3′,4′-trihydroxy-3-benzyl-2H-chromene (1), was isolated from the dried heartwood of Caesalpinia sappan L., together with seven known phenolic compounds. The structure of the new compound (1) was determined on the basis of spectroscopic analysis.     

Immunomodulatory activities of the ethanolic extract of Caesalpinia bonducella seeds

Caesalpinia bonducella FLEMING (Caesalpiniaceae) is a plant well known for its medicinal value in Indian Ayurveda. However, to prove its efficiency for the clinical utilization, more experimental data will be beneficial.

Aims of the study

The present study involved the investigation of immunomodulatory activities of ethanolic extract of Caesalpinia bonducella seeds.

Materials and methods

Neutrophil adhesion test, haemagglutinating antibody (HA) titre, delayed-type hypersensitivity (DTH) response, phagocytic activity and cyclophosphamide-induced myelosuppression were determined by in vivo experiments.

Results

The evaluation of immunomodulatory potential by oral administration of ethanolic seed extract of Caesalpinia bonducella (200–500 mg/kg) evoked a significant increase in percent neutrophil adhesion to nylon fibers as well as a dose-dependent increase in antibody titre values, and potentiated the delayed-type hypersensitivity reaction induced by sheep red blood cells. Also it prevented myelosuppression in cyclophosphamide drug treated rats and good response towards phagocytosis in carbon clearance assay.

Conclusions

The results obtained in this study indicate that Caesalpinia bonducella possesses potential immunomodulatory activity and has therapeutic potential for the prevention of autoimmune diseases.     

Antioxidant activity of Caesalpinia digyna root

The antioxidant properties of three successive extracts of Caesalpinia digyna Rottler root and the isolated compound, bergenin, were tested using standard in vitro and in vivo models. The amount of the total phenolic compounds present was also determined. The successive methanol extract of Caesalpinia digyna root (CDM) exhibited strong scavenging effect on 2,2-diphenyl-2-picryl hydrazyl (DPPH) free radical, 2,2′-azino-bis(3-ethylbenzo-thiazoline-6-sulphonic acid) diammonium salt (ABTS) radical cation, hydrogen peroxide, nitric oxide, hydroxyl radical and inhibition of lipid peroxidation. The free radical scavenging effect of CDM was comparable with that of reference antioxidants. The CDM having the highest content of phenolic compounds and strong free radical scavenging effect when administered orally to male albino rats at 100, 200 and 400 mg/kg body weight for 7 days, prior to carbontetrachloride (CCl₄) treatment, caused a significant increase in the levels of catalase (CAT) and superoxide dismutase (SOD) and significant decrease in the levels of lipidperoxidation (LPO) in serum, liver and kidney in a dose dependent manner, when compared to CCl₄ treated control. These results clearly indicate the strong antioxidant property of Caesalpinia digyna root. The study provides a proof for the ethnomedical claims and reported biological activities. The plant has, therefore, very good therapeutic potential.     

苏木酚类成分核磁共振波谱特征

结合国内外文献,对苏木中酚类成分的核磁波谱特征进行了归纳总结,为今后此类化合物的结构鉴定及波谱数据归属提供参考依据。     

苏木心材中一个新黄酮类化合物

目的:从苏木Caesalpinia sappan中寻找新的活性成分。方法:用溶剂萃取及硅胶正相色谱进行活性成分的分离纯化,根据理化性质、光谱数据进行结构鉴定。结果:从苏木95%乙醇提取物中分离得到了9个化合物:3,8-dihydroxy-4,10-dimethoxy-7-oxo-[2]benzopyrano[4,3-b][1]benzopyran-7-(5H)-one(1),3-deoxysappanchal-cone(2),sappanchalcone(3),3-deoxysappanone B(4),鼠李素(rhamnetin,5),原苏木素C(protosappanin C,6),3,7-di-hydroxy-chroman-4-one(7),己二酸二甲酯(8),胡萝卜苷(daucosterin,9)。结论:化合物1为新化合物,化合物7,8为首次从该植物中分离得到。药理筛选结果表明,化合物3对多种癌细胞株具有一定的抑制活性。     

Antipyretic and analgesic activities of Caesalpinia bonducella seed kernel extract

Ethanolic extract (70%) of Caesalpinia bonducella seed kernel has been subjected for its antipyretic and antinociceptive activities in adult albino rats or mice of either sex at 30, 100 and 300 mg/kg orally. The extract demonstrated marked antipyretic activity against Brewer's yeast-induced pyrexia in rats. The extract had significant central analgesic activity in hot plate and tail flick methods. It also exhibited marked peripheral analgesic effect in both acetic acid-induced writhing test in mice and Randall-Selitto assay in rats. It also significantly inhibited the formalin-induced hind paw licking in mice. In conclusion, the present study suggests that the ethanolic extract of Caesalpinia bonducella seed kernel possesses potent antipyretic and antinociceptive activities and thus, validates its use in the treatment of pain and pyretic disorders.     

喙荚云实酚性成分研究

对喙荚云实Caesalpinia minax枝和叶的化学成分进行了研究.实验采用硅胶和凝胶柱色谱法进行分离纯化,利用波谱法进行结构鉴定,从喙荚云实枝和叶的乙醇提取物中分离得到15个化合物,分别鉴定为芹菜素(1),5,7,3′,4′-tetra-hydroxy-3-methoxyflavone(2),毛地黄黄酮-5,3′-二甲酯(3),thevetiaflavon(4),芹菜素-7-O-β-D-葡萄糖醛酸苷(5),bonducellin(6),7-hydroxy-3-(4-hydroxybenzylidene)-chroman-4-one (7),3-去氧苏木查尔酮(8),5-acetony1-7-hydroxy-2-methylchromone(9),4-(trans)-acetyl-3,6,8-trihydroxy-3-methyl-dihydronaphthalenone(10),4-(cis-acetyl-3,6,8-trihydroxy-3-methyl-dihydronaphthalenone(11),香草酸(12),ω-hydroxypropioquaiacone(13),丁香脂素(14)及尿嘧啶(15),化合物1～14为酚性成分.以上所有化合物均为首次从喙荚云实中得到,其中化合物1～5,9～13,15为首次从云实属植物中得到.     

Anti-inflammatory properties of phenolic lactones isolated from Caesalpinia paraguariensis stem bark

Ethnopharmacological relevance

Caesalpinia paraguariensis (D. Parodi) Burkart stem bark infusion (CPBI) is traditionally used in Argentina because their “vulnerary” properties.

Aim of the study

CPBI was studied throughout bio-guided purification procedures conducted by in vitro biological assays in order to isolate the main bioactive compounds.

Material and methods

Anti-inflammatory activity was assessed by enzyme inhibition assays of Hyaluronidase (Hyal) and inducible Nitric Oxide Synthase (iNOS). The antioxidant properties were evaluated by DPPH free radical scavenging assay, lipid peroxidation inhibition assay on erythrocyte membranes, and a cell-based assay that included the fluorescent probe (DCFH-DA) for indicating reactive oxygen species (ROS) generation. Bioactive compounds were purified by chromatographic methods and their structures elucidated using spectroscopic methods (ESI-MS and 1D/2D-¹H/¹³C-NMR).

Results

Four main bioactive compounds were isolated from CPBI: ellagic acid (1), 3-O-methylellagic acid (2), 3,3'-di-O-methylellagic acid (3) and 3,3'-di-O-methylellagic-4-β-D-xylopyranoside (4). These were bioactive at concentrations in which are present in CPBI, being compounds 2 and 3 the best enzyme inhibitors of Hyal and iNOS, reaching the 90% inhibitory concentration (IC₉₀) values ranging from 2.8 to 16.4 μM, that are better than that of the positive controls, aspirin (IC₉₀: no reached) and aminoguanidine (IC₉₀: 20.2 μM) respectively. Compounds 2 and 3 were also better scavengers for lipoperoxides than butylated hydroxytoluene (BHT), reaching the 90% effective concentration (EC₉₀) at 1.2–4.5 μg/ml, and for DPPH radical (2.5–7.3 μg/ml); moreover compounds were able to exert its scavenging action on intracellular ROS. Structural features relevant to the biological activities are discussed.

Conclusions

This work provides scientific validity to the popular usage of CPBI.     

Gastroprotective activity of the ethanol extract from the inner bark of Caesalpinia pyramidalis in rats

Ethnopharmacological relevance

Caesalpinia pyramidalis Tul. (Fabaceae), known as “catingueira”, has been used in folk medicine in the treatment of various disorders such as gastritis, heartburn, indigestion, and stomach ache. However, the gastroprotective properties of this species have not yet been studied.

Materials and methods

The ethanol extract of Caesalpinia pyramidalis inner bark was used in rats via oral route, at the doses of 30, 100, and 300 mg/kg. The antiulcer assays were performed using the ethanol- and nonsteroidal anti-inflammatory drug-induced ulcer models. Gastric secretion parameters (volume, pH, and total acidity) were also evaluated by the pylorus ligated model, and the mucus in the gastric content was determined. The anti-Helicobacter pylori activity of the ethanol extract of Caesalpinia pyramidalis was performed using the agar-well diffusion and broth microdilution methods.

Results

The ethanol extract (30, 100, and 300 mg/kg) produced dose dependent inhibition (P<0.01) on the ulcer lesion index, the total lesion area, and the percentage of lesion area in the ethanol-induced ulcer model. The ethanol extract (30, 100, and 300 mg/kg) also reduced (P<0.001) the ulcer index in the indomethacin-induced ulcer model. In the model ligature pylorus, the treatment with Caesalpinia pyramidalis ethanol extract failed to significantly change the gastric secretion parameters. However, after treatment with the ethanol extract of Caesalpinia pyramidalis (30, 100, and 300 mg/kg), there was a significant increase (P<0.05) in mucus production. The ethanol extract showed anti-Helicobacter pylori activity, with inhibition halos of 12.0±1.7 mm at 10,000 μg/mL. The minimum inhibitory concentration (MIC) and minimal bactericidal concentration (MBC) values of the ethanol extract were of 625 and 10,000 μg/mL, respectively.

Conclusions

Collectively, the present results suggest that the ethanol extract of Caesalpinia pyramidalis displays gastroprotective actions, supporting the folkloric usage of the plant to treat various gastrointestinal disturbances.     

Evaluation of mechanisms involved in the antinociception of the ethanol extract from the inner bark of Caesalpinia pyramidalis in mice

Ethnopharmacological relevance

Caesalpinia pyramidalis Tul. (Fabaceae) is an endemic tree of the Northeast region of Brazil, mainly in the Caatinga region. More commonly, inner bark or flowers are traditionally used to treat many painful and inflammatory processes. A common use of this plant is made by macerating a handful of its stem bark in a liter of wine or sugarcane brandy. It is drunk against stomachache, dysenteries, and diarrheas.

Materials and methods

The ethanol extract of Caesalpinia pyramidalis inner bark was used in mice via oral route, at the doses of 10, 30, and 100 mg/kg, in behavioral models of nociception and investigates some of the mechanisms underlying this effect.

Results

The ethanol extract (30 and 100 mg/kg, P<0.001), given orally, produced dose dependent inhibition of acetic acid-induced visceral pain. The ethanol extract also caused significant and dose-dependent inhibition of capsaicin-(100 mg/kg, P<0.001) and glutamate-(10, 30, and 100 mg/kg, P<0.01) induced pain. The antinociception caused by the ethanol extract (30 mg/kg) in the abdominal constriction test was significantly attenuated (P<0.001) by intraperitoneal treatment of mice with l-arginine (600 mg/kg).

Conclusions

Collectively, the present results suggest that the ethanol extract of Caesalpinia pyramidalis produced dose-related antinociception in several models of pain through mechanisms that involved both glutamatergic system and/or the l-arginine–nitric oxide pathway, supporting the folkloric usage of the plant to treat various painful processes.