Synthesis,anti-inflammatory,analgesic and antioxidant activities of some tetrasubstituted thiophenes

Sets of tetrasubstituted thiophene esters 4a-4g, 5a-5f and 6a-6e were synthesized by reaction of 1-(α-Carbomethoxy-β-aminothiocrotonoyl)-aryl/aroyl amines (3) with 3-(bromoacetyl)coumarin, 1,4-dibromodiacetyl and chloroacetone respectively. The compound 3 were synthesized by nucleophilic addition of aryl/aroylisothiocyanate and enamine (2). The synthesized targeted compounds (4a-4g, 5a-5f and 6a-6e) were evaluated for their in vivo anti-inflammatory activity in carrageenin-induced rat hind paw oedema model at three graded doses employed at 10, 20 and 40 mg/kg body weight using mefanamic acid, ibuprofen and in vivo analgesic activity in acetic acid induced writhing response model at 10 mg/kg dose using ibuprofen as standard drug. The compounds 4a-4f, 5c, 5f, 6c and 6e were evaluated for their in vitro antioxidant nitric oxide radical scavenging assay at the concentrations of 5, 10, 15, 20, 25, 30 and 35 μg/mL using ascorbic acid as standard drug. Among all the targeted compounds 4c showed maximum anti-inflammatory activity of 71% protection at 10 mg/kg and 77% protection at 20 mg/kg to inflamed paw and analgesic activity of 56% inhibition and also maximum in vitro nitric oxide radical scavenging activity having IC₅₀ value 31.59 μg/mL.     

白皮锦鸡儿黄酮醇类化合物及其抗菌和抗氧化活性(英文)

从豆科植物白皮锦鸡儿(Caragana leucophloea Pojark.)地上部分分离到3个黄酮醇类化合物,经理化和波谱分析鉴定为3-O-甲基山奈酚(1)、3-O-甲基槲皮素(2)和槲皮素(3)。活性测定表明,1表现出较强的抗细菌活性,对大肠杆菌和番茄疮痂病菌的半抑制浓度分别为9.00μg/mL和7.42μg/mL,最低抑制浓度均为12.5μg/mL;而2和3则表现出较强的抗氧化活性,对DPPH还原的半抑制浓度分别为14.39μg/mL和13.64μg/mL;对β-胡萝卜素-亚油酸氧化的半抑制浓度分别为10.26μg/mL和9.87μg/mL。上述黄酮醇类化合物均为首次从白皮锦鸡儿中分离得到。     

A New Species of Caragana Lam. from Xizang,China

Caragana sajaensis Ni (Leguminosae)is described from Xizang, China, asnew.     

Isothiocyanates: cholinesterase inhibiting,antioxidant, and anti-inflammatory activity

Finding a new type of cholinesterase inhibitor that would overcome the brain availability and pharmacokinetic parameters or hepatotoxic liability has been a focus of investigations dealing with the treatment of Alzheimer’s disease. Isothiocyanates have not been previously investigated as potential cholinesterase inhibitors. These compounds can be naturally produced from their glucosinolate precursors, secondary metabolites widely distributed in our daily Brassica vegetables. Among 11 tested compounds, phenyl isothiocyanate and its derivatives showed the most promising inhibitory activity. 2-Methoxyphenyl ITC showed best inhibition on acetylcholinesterase with IC₅₀ of 0.57?mM, while 3-methoxyphenyl ITC showed the best inhibition on butyrylcholinesterase having 49.2% at 1.14?mM. Assessment of the antioxidant efficacy using different methods led to a similar conclusion. The anti-inflammatory activity was also tested using human COX-2 enzyme, ranking phenyl isothiocyanate, and 3-methoxyphenyl isothiocyanate as most active, with ～99% inhibition at 50?μM.     

An anti-inflammatory isoflavone from soybean inoculated with a marine fungus Aspergillus terreus C23-3

ABSTRACT

A new isoflavone derivative compound 1 (psoralenone) was isolated from soybean inoculated with a marine fungus Aspergillus terreus C23-3, together with seven known compounds including isoflavones 2–6, butyrolactone I (7) and blumenol A (8). Their structures were elucidated by MS, NMR, and ECD. Psoralenone displayed moderate in vitro anti-inflammatory activity in the LPS-induced RAW264.7 cell model. Compound 2 (genistein) showed moderate acetylcholinesterase (AChE) inhibitory activity whereas compounds 2, 5 (biochanin A), 6 (psoralenol), and 7 exhibited potent larvicidal activity against brine shrimp. Compounds 3 (daidzein), 4 (4?-hydroxy-6,7-dimethoxyisoflavone), and 5–7 showed broad-spectrum anti-microbial activity, and compound 7 also showed moderate 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging activity.     

Flemiphyllin,an isoflavone from stems of Flemingia macrophylla

A new isoflavone, designated flemiphyllin, was isolated from a petrol extract of the stems of Flemingia macrophylla. Its structure was established as 5,7,4′-trihydroxy-3′,5′,8-tri(3-methylbut-2-enyl) isoflavone on the basis of physical and chemical evidence.     

A benzil and isoflavone derivatives from Derris scandens Benth

A benzil derivative: scandione, 2',2"-dihydroxy-4'-methoxy-4",5"-methylenedioxybenzil and two isoflavones: scandenal, 3'-formyl-4',5-dihydroxy-2",2"-dimethylchromeno-[6,7:5",6"]isoflavone and scanderone, 4',5-dihydroxy-3'-prenyl-2",2"-dimethylchromeno-[7,8:6",5"]isoflavone together with fifteen known compounds were isolated from the stem of D. scandens. Their structures were determined by spectroscopic methods. Radical scavenging, antibacterial and hypertensive activities of some of the compounds were investigated.     

Dual antioxidant structures with potent anti-inflammatory,hypolipidemic and cytoprotective properties

Novel amide derivatives of trolox, 3,5-di-tert-butyl-4-hydroxybenzoic acid, (E)-3-(3,5-di-tert-butyl-4-hydroxyphenyl)acrylic acid and cinnamic acid with cysteamine and l-cysteine ethyl ester were synthesised. In four cases, the disulfide derivatives were also isolated and tested. All compounds were examined for antioxidant activity, expressed as their ability to inhibit lipid peroxidation and to scavenge free radicals. They were found to demonstrate up to 17-fold better activity than that of the parent antioxidant acids. They could reduce acute inflammation up to 87%. The most active antioxidant compounds were further tested for their in vivo hypolipidemic effect, which ranged from 47% to 73%, and for their ability to protect the liver against oxidative toxicity caused by high paracetamol dose. The disulfide derivatives of 3,5-di-tert-butyl-4-hydroxybenzoic acid and cinnamic acid had no antioxidant activity and presented equal or lower anti-inflammatory effect than their thiol analogues, indicating that their molecular characteristics may not permit biological barrier penetration.     

Viridiflorin,an isoflavone from Tephrosia viridiflora

A new isoflavone, viridiflorin, has been isolated from Tephrosia viridiflora. Its structure was established as 4′,5,7-trihydroxy-2′,5′-dimethoxy-6-prenylisoflavone based on spectral evidence and chemical transformation.     

锦鸡儿属植物一些种类的染色体数目及核型研究

报道了国产10种锦鸡儿的染色体数目,并对其中9种的核型进行了研究。这9个种的核型公式分别为：荒漠锦鸡儿（Caragana roborovskyi）,2n＝16＝10m(2SAT)+6sm;川西锦鸡儿（C. erinacea）,2n=16=10m+6sm;密叶锦鸡儿（C. densa）,2n=16=10m（2SAT）+6sm;刺叶锦鸡儿（C. acanthophylla）,2n=16=12m+4sm;柄荚锦鸡儿（C. stipitata）,2n=16=10m+6sm;甘蒙锦鸡儿（C. opulens）,2n=16=12m(2SAT)+4sm;白皮锦鸡儿（C. leucophloea）,2n=32=22m(4SAT)＋10sm;北疆锦鸡儿（C. camilli-schneideri）,2n=32=20m(4SAT)+12sm;中亚锦鸡儿（C. tragacanthoides）,2n=32=20m(2SAT)+10sm+2st+2B。白毛锦鸡儿（C.licentiana）2个居群的染色体数目均为2n=32,为四倍体。研究结果表明,锦鸡儿属的核型一般比较对称,核型上的特化往往与其形态上的特化相关联,但也有例外。从倍性水平上来看,二倍体类群多是一些羽状叶的种,在分布上倾向于亚洲东部其祖先分布区,而四倍体的种类多是一些假掌状叶的类群,分布于西部干旱生境中,在形态上也表现的较为特化。这也符合锦鸡儿属的演化趋势。     

Developmental and nutritional regulation of isoflavone secretion from soybean roots

Isoflavones play important roles in plant–microbe interactions in rhizospheres. Soybean roots secrete daidzein and genistein to attract rhizobia. Despite the importance of isoflavones in plant–microbe interactions, little is known about the developmental and nutritional regulation of isoflavone secretion from soybean roots. In this study, soybeans were grown in hydroponic culture, and isoflavone contents in tissues, isoflavone secretion from the roots, and the expression of isoflavone conjugates hydrolyzing beta-glucosidase (ICHG) were investigated. Isoflavone contents did not show strong growth-dependent changes, while secretion of daidzein from the roots dramatically changed, with higher secretion during vegetative stages. Coordinately, the expression of ICHG also peaked at vegetative stages. Nitrogen deficiency resulted in 8- and 15-fold increases in secretion of daidzein and genistein, respectively, with no induction of ICHG. Taken together, these results suggest that large amounts of isoflavones were secreted during vegetative stages via the hydrolysis of (malonyl)glucosides with ICHG.     

毛乌素沙地中间锦鸡儿根瘤菌的多样性及其抗逆性

从内蒙古毛乌素沙地优势物种中问锦鸡儿收集根瘤,分离根瘤菌15株,对其进行同工酶电泳,聚类分析证明中间锦坞儿的遗传多样性对其耐盐性、耐酸碱性、生长温度范围、产酸产碱性、过氧化氢酶活性以及唯一碳源利用能力进行比较研究,结果表明,所有中间锦鸡儿根瘤菌均分泌H^+,都具有过氧化氢酶活性,73.3%的菌株可以在含3％NaCl的YMA培养基上生长,80％的菌株可以抵抗50℃高温,除对乳糖和淀粉利用表现出差异外,中间锦鸡儿根瘤菌对其余碳源没有选择性,证明中间锦鸡儿根瘤菌具有较强的抗逆性,但仍存在菌株间差异,是对毛乌素沙地多种景观生态类型的适应作为一种新的种质资源,中间锦鸡儿根瘤菌可用于恶劣生境固氮。     

Antiplatelet,antioxidative, and anti-inflammatory effects of hydroquinone

Platelets play crucial roles in thrombosis and hemostasis through platelet activation and aggregation that are crucial in cardiovascular diseases. Hydroquinone (HQ) and its derivatives are present in many dermatological creams, paints, motor fuels, air, microorganisms, and plant products like wheat bread, fruit, coffee, and red wine. The effect of HQ on humans is not clear. In this study, we found that HQ (>25 μM) inhibited arachidonic acid (AA)-induced platelet aggregation. HQ suppressed AA-induced thromboxane B2 production of platelets. HQ (>10 μM) also attenuated ex vivo platelet-rich plasma aggregation. HQ prevented the interleukin (IL)-1β-induced 8-isoprostane, and PGE2 production, but not IL-8 production of pulp cells. These results indicate that HQ may have an antiplatelet effect via inhibition of thromboxane production. HQ has antioxidative and anti-inflammatory effects, and possible inhibition of COX. Exposure and consumption of HQ-containing products, food or drugs may have antiplatelet, antioxidative, and anti-inflammatory effects.     

基于ITS序列和trnL-F序列探讨小叶锦鸡儿、中间锦鸡儿和柠条锦鸡儿的种间关系

中间锦鸡儿Caragana davazamcii Sancz.的分类处理一直存在争议, 它与小叶锦鸡儿C. microphylla Lam.和柠条锦鸡儿C. korshinskii Kom.的关系尚不清楚。该种被处理为一个独立的种或后两个种的变种。本文利用ITS序列和叶绿体trnL-F序列, 综合形态和地理分布, 探讨了中间锦鸡儿的起源及与另外两个种的种间关系。结果显示, 中间锦鸡儿的trnL-F序列与小叶锦鸡儿完全一致, 而与柠条锦鸡儿有明显差异。中间锦鸡儿的ITS序列高度纯合, 不支持该种可能是杂交起源的假设。相反, 另外两个种的ITS序列均出现多个位点杂合, 克隆后均得到2种不同的序列。中间锦鸡儿的ITS序列与小叶锦鸡儿2种序列中的1种完全一致。该结果表明, 中间锦鸡儿可能作为亲本之一参与了小叶锦鸡儿的杂交起源, 或者基因流是造成这两个种形态相似的主要原因。中间锦鸡儿与柠条锦鸡儿形态上的相似可能是趋同进化的表现。     

子树分析和TASS程序及其在锦鸡儿属植物中的应用

子树分析和三分法(TASS)程序是历史生物地理学中分布区关系的一种分析途径.它以分类群分支图为基础,以剔除其中分布区关系相悖理的结点并确定具信息的子树为目标,以便更有效地利用分布区信息.对分布区关系可以用若干子树和一个分布区分支图来表示.对锦鸡儿属(Caragana)植物72种和13个分布区的子树分析和TASS程序运算后,得到7个具信息的子树,它们分别表达了锦鸡儿属属内组、系所具有的分布区关系.属的分布区分支图也表达了13个分布区的关系.与以前我们对本属成分分析的结果相吻合.