Irritant potential of some constituents from the seeds of Caesalpinia bonducella (L.) Fleming

The irritant potential of four triterpenoids, isolated for the first time from the seeds of Caesalpinia bonducella, identified as f -amyrin [12-ursen-3 g -ol], g -amyrin [12-oleanex-3 g -ol], lupeol [lup-20(29)-en-3 g -ol] and lupeol acetate [lup-20(29)-en-3 g -yl acetate] was investigated by open mouse ear assay, evaluating their ID₅₀ (irritant dose in 50% animals) after acute effects and by irritant units (IU) after chronic effects. f -Amyrin, lupeol acetate and g -amyrin were the most potent and persistent irritant compounds with red weals of 1.5-2.1 cm diameter areas of the animal skin and with lowest ID₅₀ =0.078, 0.186 and 0.190 mg/10 w l after 1.5, 2.10 and 3.5 h, respectively. Their reactions lasted for 24 h with IU=2.5; 0.312 and 1.25 mg/10 w l, respectively. Lupeol was the least irritant and least persistent compound with ID₅₀ =0.603 mg/10 w l after 4.5 h. Its reaction subsided before 24 h.     

Anticonvulsant compounds from the wood ofCaesalpinia sappan L.

80% Aqueous MeOH extracts from the wood of Caesalpinia sappan, which showed remarkable anticonvulsant activity, were fractionated using EtOAc, n-BuOH, and H2O. Among them, the EtOAc fraction significantly inhibited the activities of two GABA degradative enzymes, succinic semialdehyde dehydrogenase (SSADH) and succinic semialdehyde reductase (SSAR). Repeated column chromatographies for the fraction guided by activity test led to the isolation of the two active principal components. Their chemical structures were determined to be sappanchalcone and brazilin based on spectral data. The pure compounds, sappanchalcone (1) and brazilin (2), inactivated the SSAR activities in a dose dependent manner, whereas SSADH was inhibited partially by sappanchalcone and not by brazilin.     

The antibacterial principle of Caesalpina sappan

Using a bioassay-directed purification scheme, the active antibacterial principle from Caesalpina sappan was isolated and identified to be brasilin. This compound showed potent activity against antibiotic-resistant bacteria, notably methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE), multi-drug resistant Burkholderia cepacia as well as a number of other bacteria. The minimal inhibitory concentrations ranged from 4 to 32 microg/mL. The results from time-kill studies showed that brasilin is bactericidal against MRSA. The addition of brasilin to growing MRSA cells resulted in a rapid inhibition of incorporation of [(3)H] thymidine or [(3)H] serine into DNA and proteins, respectively. Exposure of MRSA to a sub-MIC level of brasilin for ten consecutive subcultures did not induce resistance to the compound. The Trypan blue dye exclusion test showed that brasilin lacked cytotoxicity against Vero cells. In conclusion, brasilin is an antibacterial principle from C. sappan and it has the potential to be developed into an antibiotic.     

Protective effects of 3′‐deoxy‐4‐O‐methylepisappanol from Caesalpinia sappan against glutamate‐induced neurotoxicity in primary cultured rat cortical cells

To examine the neuroprotective effects of Caesalpinia sappan L., we tested its protection against the glutamate‐induced neurotoxicity in primary cortical cultured neurons. We found that an aqueous extract of this medicinal plant exhibited significant protection against glutamate‐induced toxicity in primary cultured rat cortical cells. In order to clarify the neuroprotective mechanism(s) of this observed effect, isolation was performed to seek and identify active fractions and components. By such fractionation, two known compounds – sappanchalcone and 3′‐deoxy‐4‐O‐methylepisappanol – were isolated from the methanol extracts from the air‐dried and chipped C. sappan. Among these two compounds, 3′‐deoxy‐4‐O‐methylepisappanol exhibited significant neuroprotective activities against glutamate‐induced toxicity, exhibiting cell viability of about 50%, at concentrations ranging from 0.1 μM to 10 μM. Therefore, the neuroprotective effect of C. sappan might be due to the inhibition of glutamate‐induced toxicity by the protosappanin derivative it contains. Copyright © 2009 John Wiley & Sons, Ltd.     

Antimicrobial activity of seed extracts and bondenolide from Caesalpinia bonduc (L.) Roxb

The antibacterial and antifungal activities, along with a phytotoxicity test of the newly isolated diterpene bondenolide (1), of a methanol extract, ethylacetate fraction and water soluble part of the methanol extract of Caesalpinia bonduc (L.) Roxb. were assayed.     

鸡嘴簕的化学成分分离和鉴定

目的 对鸡嘴簕枝叶的化学成分进行分离和鉴定。方法 利用硅胶柱色谱、Sephadex LH-20凝胶柱色谱等现代多种色谱技术进行分离纯化,利用核磁共振等波谱技术和文献对照的方法进行结构鉴定。结果从鸡嘴簕枝叶中分离鉴定了12个化合物,分别为caesaloside A （1）,2β-ethoxyclovane-9α-ol （2）,2β-methoxyclovan-9α-ol （3）,8（17）,13-ent-labdadien-15→ 16-lactone-19-oic acid （4）,高根二醇（5）,3-甲氧基槲皮素（6）,槲皮素（7）,芹菜素（8）,木犀草素（9）,3,5-二羟基-4-甲氧基苯甲酸乙酯（10）,没食子酸乙酯（11）和没食子酸（12）。结论 化合物1 和2 为新化合物,其余10个化合物皆为首次报道从该植物中分离得到。     

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、MΦ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T 转功能，但各剂量组均不影响B淋转功能、Nk细胞的活性及MΦ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MΦ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MΦ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，苏木醇提物可能是一种很有前途的抗排斥新药。     

云实种子的二萜类成分研究

目的研究云实Caesalpinia decapetala种子的化学成分。方法采用硅胶、Sephadex LH-20等柱色谱技术对云实种子的乙醇提取物进行前处理,进而运用半制备高效液相色谱进行分离,采用NMR、MS等波谱方法进行鉴定。结果从云实种子的氯仿部位分离得到了5个卡山烷二萜类化合物,根据NMR、MS等数据鉴定为云实二萜F1(1)、α-caesalpin(2)、caesalmin F(3)、caesalmin C(4)、caesalmin E(5)。结论化合物1为1个新化合物,命名为云实二萜F1;化合物4、5为首次从该植物中分离得到。化合物1、4和5对人宫颈癌He La细胞均有一定的抑制作用,其IC50分别为64.3、42.9、81.2μmol/L。     

苏木化学成分及抗肿瘤研究进展

介绍国内外对苏木的化学成分、药理作用及抗肿瘤等方面的研究,讨论苏木在抗肿瘤方面的广泛前景,并对如何推进苏木的研究提出建议。     

Bioactivity-guided isolation of cytotoxic constituents from three medicinal plants

Abstract

Context: The ethanol extracts and their fractions of three Indian medicinal plants, Ervatamia coronaria (Jacq.) Stapf, (Apocynaceae), Mimosa pudica L. (Mimosaceae) and Caesalpinia bonduc (L.) Roxb. (Caesalpiniaceae) were tested for their cytotoxic activity in the brine shrimp lethality (BSL) bioassay and in various cancer cell lines. The plants were selected based on their traditional use in the treatment of cancer/tumors.

Objectives: To investigate the in vitro cytotoxicity of Ervatamia coronaria, Mimosa pudica and Caesalpinia bonduc.

Materials and methods: Ethanolic extracts and their fractions of E. coronaria, M. pudica and C. bonduc were subjected to cytotoxicity studies using BSL bioassay method with concentrations of 10, 50, 100, 500 and 1000?µg/ml. The alkaloid fraction of E. coronaria with significant cytotoxicity in BSL bioassay was subjected to in vitro cytotoxicity studies with HT-29, A-549, HepG-2, MCF-7 and L-6 cell lines at concentrations of 12.5, 25, 50, 100 and 200?µg/ml and a DNA fragmentation study using the HT-29 cell line.

Results: The alkaloid fractions of E. coronaria and M. pudica showed significant cytotoxicity with LC₅₀ values of 65.83 and 85.10?µg/ml in the BSL bioassay, respectively. The purified alkaloid fraction of E. coronaria exhibited highest cytotoxicity in HT-29, A-549 and MCF-7 cell lines with IC₅₀ values of 32.5, 47.5 and 72.5?µg/ml, respectively, and induced DNA fragmentation in the HT-29 cell line at a concentration of 65?µg/ml.

Conclusion: The alkaloid fraction of E. coronaria exhibited significant cytotoxicity. Alkaloids such as ervatamine, apparicine and coronaridine that were earlier reported may be responsible for this activity.