Antimalarial potential of kolaviron,a biflavonoid from Garcinia kola seeds,against Plasmodium berghei infection in Swiss albino mice

Objective:To investigate the antimalarial potential of kolaviron(KV),a biflavonoid fraction from Garcinia kola seeds,against Plasmodium berghei(P.berghei)infection in Swiss albino mice.Methods:The study consists of seven groups of ten mice each.Groups I,II and III were normal mice that received com oil.KV1 and chloroquine(CQ),respectively.Groups IV,V,ⅥandⅦwere infected mice that received corn oil.CQ,KYI and KV2.respectively.CQ.KY1 and KV2were given at 10-,100-and 200-mg/kg daily,respectively for three consecutive days.Results:Administration of KV1 and KV2 significantly(P<0.05)suppressed P.berghei-infection in the mice by 85%and 90%.respectively,while CQ produced 87%suppression relative to untreated infected group after the fifth day of treatment.Also,KV2 significantly(P<0.05)increased the mean survival time of the infected mice by 175%.The biflavonoid prevented a drastic reduction in HCV from day4 of treatment,indicating its efficacy in ameliorating anaemia.Significant(P<0.05)oxidative stress assessed by the elevation of serum and hepatic malondialdehydewere observed in unlrealed P.berghei-infected mice.Specifically,senum and hepatic malondialdehyde levels increased by93%and 78%,resjiectively in the unlrealed infecled mice.Furlhennore,antioxidant indices,viz;superoxide dismutase.catalase,glutathione-s-transferasc.glualhione peroxidase and reduced gluathione decreased significantly(P<0.05)in the tissues of untreated P.berghei-infected mice.KV significantly(P<0.05)ameliorated the P.berghei-induced decrease in antioxidant status of the infected mice.Conclusions:This study shows that kolaviron,especially at 200 mg/kg,has high antimalarial activities in P.berghei-infected mice,in addition to its known antioxidant properties.

A new biflavonoid from Selaginella labordei Hieron.ex Christ

A new biflavonoid, 2,3-dihydro-5,5″,7,7,4′-pentahydroxy-6,6＂-dimethyl-[3′-O-4″]-biflavone 1 and two known biflavonoids 2,3＂-dihydroochnaflavone 2 and 2″,3″-dihydro-3′,3-biapigenin 3 were isolated from the herb of Selaginella labordei Hieron. ex Christ. Their structures were elucidated by spectroscopic methods. ？2009 Ke Li Chert. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

A New Biflavonoid from Stellera chamaejasme L.

A new biflavonoid, stelleranol, was isolated from the roots of Stellera chamaejasme L.. Its structure was determined by the analysis of MS and NMR data, especially 2D NMR spectra.

Hinokiflavone and Related C-O-C-Type Biflavonoids as Anti-cancer Compounds:Properties and Mechanism of Action

Biflavonoids are divided in two classes:C-C type compounds represented by the dimeric compound amentoflavone and C-O-C-type compounds typified by hinokiflavone(HNK)with an ether linkage between the two connected apigenin units.This later sub-group of bisflavonyl ethers includes HNK,ochnaflavone,delicaflavone and a few other dimeric compounds,found in a variety of plants,notably Selaginella species.A comprehensive review of the anticancer properties and mechanism of action of HNK is provided,to highlight the anti-proliferative and anti-metastatic activities of HNK and derivatives,and HNK-containing plant extracts.The anticancer effects rely on the capacity of HNK to interfere with the ERK1-2/p38/NFκB signaling pathway and the regulation of the expression of the matrix metalloproteinases MMP-2 and MMP-9(with a potential direct binding to MMP-9).In addition,HNK was found to function as a potent modulator of pre-mRNA splicing,inhibit-ing the SUMO-specific protease SENP1.As such,HNK represents a rare SENP1 inhibitor of natural origin and a scaffold to design synthetic compounds.Oral formulations of HNK have been elaborated to enhance its solubility,to facilitate the compound delivery and to enhance its anticancer efficacy.The review shed light on the anticancer potential of C-O-C-type biflavonoids and specifically on the pharmacological profile of HNK.This compound deserves further attention as a regu-lator of pre-mRNA splicing,useful to treat cancers(in particular hepatocellular carcinoma)and other human pathologies.

八角莲中两对新的双黄酮对应异构体

采用硅胶柱色谱、Sephadex LH-20柱色谱和制备型高效液相色谱法,从八角莲乙醇提取物中分离得到5个双黄酮类化合物。通过波谱数据分析(MS、UV、IR、NMR)与电子圆二色谱(ECD)技术,分别鉴定为(+)-八角莲双黄酮H(1a)、(-)-八角莲双黄酮H(1b)、(+)-八角莲双黄酮I(2a)、(-)-八角莲双黄酮I(2b)、podoverine F(3),其中,1a与1b、2a与2b为2对新的双黄酮对应异构体。DPPH自由基清除实验结果显示,化合物2、2a、2b对DPPH自由基具有较强的清除能力,IC 50值分别为8.87、10.18、11.35μmol/L,且强于阳性药trolox(14.95μmol/L)。化合物2、2a、2b对DPPH自由基的清除能力分别强于化合物1、1a、1b,进一步的构效关系研究表明,B环上邻二酚羟基是黄酮类化合物具有DPPH自由基清除活性的必需结构基团。

天然双黄酮提取分离方法及生物活性研究进展

目的:天然双黄酮是自然界中低分子量多酚类物质,表现出很高生物活性。从草药中提取有效成分并加以利用的方法一直是重点研究方向,因此梳理近年来双黄酮类化合物的提取分离纯化方法及其生物活性具有重要意义。方法:利用中国知网(CNKI)和ScienceDirect数据库分别检索双黄酮类化合物的分布、提取分离纯化方法以及双黄酮类化合物的生物活性。结果:总结了国内外双黄酮提取分离纯化方法,明确了双黄酮类化合物抗氧化、抗炎、抑制癌细胞、抗病毒、抗菌等药理作用,为双黄酮类化合物进一步开发利用提供理论依据。结论:双黄酮的功能和开发利用方面仍有很大发展空间,且剂型研究存在较大差距,需要进一步研究补充。

Potential hepatic and renal toxicity induced by the biflavonoids from Ginkgo biloba

Evidence continues to grow on potential health risks associated with Ginkgo biloba and its constituents.While biflavonoid is a subclass of the flavonoid family in Ginkgo biloba with a plenty of pharmacological properties,the potential toxicological effects of biflavonoids remains largely unknown.Thus,the aim of this study was to investigate the in vitro and in vivo toxicological effects of the biflavonoids from Ginkgo biloba(i.e.,amentoflavone,sciadopitysin,ginkgetin,isoginkgetin,and bilobetin).In the in vitro cytotoxicity test,the five biflavonoids all reduced cell viability in a dose-dependent manner in human renal tubular epithelial cells(HK-2)and human normal hepatocytes(L-02),indicating they might have potential liver and kidney toxicity.In the in vivo experiments,after intragastrical administration of these biflavonoids at 20 mg·kg^–1·d^–1 for 7 days,serum biochemical analysis and histopathological examinations were performed.The activity of alkaline phosphatase was significantly increased after all the bifl avonoid administrations and widespread hydropic degeneration of hepatocytes was observed in ginkgetin or b ilobetin-treated mice.Moreover,the five biflavonoids all induced acute kidney injury in treated mice and the main pathological lesions were confirmed to the tubule,glomeruli,and interstitium injuries.As the in vitro and in vivo results suggested that these biflavonoids may be more toxic to the kidney than the liver,we further detected the mechanism of biflavonoids-induced nephrotoxicity.The increased TUNEL-positive cells were detected in kidney tissues of biflavonoids-treated mice,accompanied by elevated expression of proapoptotic protein BAX and unchanged levels of antiapoptotic protein BCL-2,indicating apoptosis was involved in biflavonoids-induced nephrotoxicity.Taken together,our results suggested that the five biflavonoids from Ginkgo biloba may have potential hepatic and renal toxicity and more attentions should be paid to ensure Ginkgo biloba preparations safety.

地卷柏的化学成分及其α-葡萄糖苷酶抑制活性研究

研究地卷柏(Selaginella prostrata H.S.Kung)的化学成分及其α-葡萄糖苷酶抑制活性,综合运用硅胶、Sephadex LH-20和半制备HPLC等多种色谱分离技术,从地卷柏全草的95%乙醇提取物中分离得到10个化合物,通过现代波谱学方法鉴定其结构为seprostrataoid A(1)、(3 S,5 R,8 S)-5,8-epoxy-6-megastigmadien-3,9-diol(2)、(-)-黑麦草内酯(3)、(3 S,5 R,6 R,7 E)-3,5,6-三羟基-7-巨豆烯-9-酮(4)、(7 R,8 S)-ceplignan(5)、(2 R,3 S)-二氢-2-(3′,5′-二甲氧基-4′-羟基苯基)-3-羟甲基-7-甲氧基-5-乙酰基苯骈呋喃(6)、5,5′-二甲氧基木香酚A(7)、穗花衫双黄酮(8)、异柳杉双黄酮(9)、扁柏双黄酮(10)。其中,化合物1为新的倍半萜类化合物,化合物2~10为首次从地卷柏中分离得到。α-葡萄糖苷酶抑制活性测试结果显示,化合物7~10具有较好的α-葡萄糖苷酶抑制活性,IC 50值分别为72.14±2.67、42.68±1.54、61.26±4.32、55.43±2.17μmol/L。

卷柏总双黄酮有效部位通过抑制PI3K/AKT通路抗弥漫大B细胞淋巴瘤

目的探究卷柏总双黄酮(TBF)有效部位治疗弥漫大B细胞淋巴瘤(DLBCL)的作用及可能机制。方法采用CCK-8法检测TBF有效部位对DLBCL细胞增殖的影响;流式细胞术检测TBF有效部位对DLBCL细胞凋亡及周期的影响;转录组学测序并富集差异基因,初步探讨TBF有效部位抗DLBCL的作用机制;Western blotting验证TBF有效部位影响的信号通路。结果TBF有效部位对DLBCL不同亚型细胞株的增殖均有显著抑制作用,且可诱导DLBCL细胞凋亡,将细胞周期阻滞于G_(2)期。TBF有效部位主要对细胞内PI3K/AKT信号通路产生影响。随着TBF有效部位浓度的增加,PI3K、AKT的表达量及p-PI3K、p-AKT与对照组相比显著降低。结论TBF有效部位可通过抑制PI3K/AKT信号通路激活发挥抗DLBCL作用,为DLBCL临床治疗提供了新策略。

长梗瑞香中黄酮类化学成分研究

目的研究采自云南省元阳县长梗瑞香Daphne pedunculata中的黄酮类化学成分。方法采用正相、反相硅胶柱色谱、Sephadex LH-20凝胶柱色谱、半制备液相色谱等色谱方法进行分离纯化,运用核磁共振和质谱等波谱方法鉴定化合物的结构。结果从长梗瑞香95%乙醇提取物中分离得到21个黄酮化合物,其中双黄酮化合物12个。分别鉴定为异狼毒素(1)、新狼毒素A(2)、新狼毒素B(3)、荛花醇B(4)、毛瑞香素D2(5)、荛花醇A(6)、genikwanol A(7)、瑞香黄烷B(8)、wikstaiwanone B(9)、wikstaiwanone A(10)、瑞香黄烷G(11)、芹菜素(12)、木犀草素(13)、芫花素(14)、紫云英苷(15)、芹菜素-7-O-葡萄糖苷(16)、山柰酚(17)、木犀草苷(18)、刺槐素(19)、瑞香黄烷F(20)、5-甲氧基-芹菜素-7-O-β-D-葡萄糖苷(21)。结论从长梗瑞香95%乙醇提取物中分离得到21个黄酮化合物中,除化合物12~14外,其余均为首次从长梗瑞香中分离得到。该研究结果丰富了长梗瑞香植物黄酮的化学多样性,并为其深入研究及利用提供重要的基础和科学依据。

基于UPLC-QTOF-MS/MS的卷柏化学成分分析

利用超高效液相色谱-四级杆飞行时间串联质谱法(UPLC-QTOF-MS/MS)对中药卷柏的化学成分进行快速分析及鉴定。采用Agilent Poroshell 120 SB-Aq(2.7μm,2.1 mm×100 mm)色谱柱,以乙腈-0.1%甲酸水溶液为流动相,梯度洗脱,流速为0.4 mL/min,进样量为3μL;选择电喷雾离子源分别在正、负离子模式下扫描分析,通过保留时间、精确相对分子质量和二级质谱裂解碎片,对所得成分的主要色谱峰进行鉴定。结果显示从卷柏中共鉴定出54个化学成分,主要包括双黄酮及黄酮类15个、炔酚类12个、酚酸类10个、苯丙素类5个、甾体类2个、萜类2个、氨基酸及肽类2个、酯类2个和其他类4个,并首次探讨炔酚类成分的裂解规律。该研究建立的UPLC-QTOF-MS/MS方法可以快速准确且较全面地分析鉴定卷柏中的化学成分,可为其质量控制及药效物质基础研究提供科学依据。

A BIFLAVONOID AMENTOFLAVONE FROM GARCINIA XANTHOCHYMUS FRUIT EXHIBITEDANTI-ANGIOGENIC ACTIVITIES IN ZEBRAFISH EMBRYOS

Edible fruits of Garcinia xanthochymus were traditionally used to treat diarrhoea and dysentery.Our previous work showed that some components of G.xanthochymus fruits induced apoptosis in colon cancer cells.In this study,the aril(edible pulp of the fruit)and seed of G.xanthochymus fruits were further investigated for their

瑞香狼毒中的化学成分

目的 研究瑞香狼毒 Stellera chamaejasme根中的化学成分。方法 利用各种色谱法分离化学成分 ,通过理化性质和波谱的分析鉴定结构。结果 从瑞香狼毒根中分离得到 1个木脂素类化合物和 3个双黄酮类化合物 ,分别鉴定为 bursehernin( ) ,狼毒宁 B(chamaejasmenin B, ) ,异新狼毒素 A(isoneochamaejasm in A, )和 (+) -狼毒素 [(+) - cham aejasmin, ]。结论 化合物 和 为新旋光异构体 ,化合物 为首次从狼毒属中分得。

瑞香狼毒化学及药理研究进展

瑞香狼毒为传统中药 ,主要含有二萜类、香豆素类、木脂素类及黄酮类化学成分。二萜及双黄酮具有较强的抗肿瘤及抗 HIV等病毒活性。对瑞香狼毒的化学成分与药理活性进行了综述。

瑞香狼毒根中酚类成分的研究

目的:研究瑞香狼毒根中的酚类化学成分。方法:采用溶剂法提取及各种色谱分离法分离纯化,利用波谱法进行结构鉴定。结果:共分离得到2种酚类化学成分,分别鉴定为瑞香酚(stelleranol,1)和伞形花内酯-7-氧葡萄糖苷(umbelliferone-7-O-glucoside,2)。结论:瑞香酚(1)为新双黄酮类化合物,伞形花内酯-7-氧葡萄糖苷(2)为首次从该种植物中分得的成分。

中华卷柏的化学成分研究

目的 研究中华卷柏Selaginella sinensis的化学成分。方法 利用Diaion HP-20，Toyopearl HW-40，硅胶柱等柱色谱技术进行分离纯化。根据化合物的理化性质和光谱数据鉴定结构。结果 分离并鉴定了11个化合物的结构，分别为：β-谷甾醇（Ⅰ）、香荚兰酸（Ⅱ）、（7S，8R）-4，9，9′-三羟基-3，31-二甲氧基-7，8-二氢苯并呋喃-1′-丙基新木脂素（Ⅲ）、丁香脂素（Ⅳ）、（一）-松脂素（Ⅴ）、松脂酚-4-O-β-D-葡萄糖苷（Ⅵ）、丁香脂素-4，4′-O-二-β-D-葡萄糖苷（Ⅶ）、β-甲基-D-吡喃木糖苷（Ⅷ）、β-甲基-D-吡喃阿拉伯糖苷（Ⅸ）、扁柏双黄酮（Ⅹ）、阿曼托双黄酮（Ⅺ）。结论 化合物Ⅱ～Ⅸ均为首次从该植物中分离得到。

祖师麻中的双黄酮类成分研究

目的 分离并鉴定祖师麻 Daphne giraldii中的黄酮类化合物。方法 利用硅胶柱色谱和 Sephadex L H- 2 0凝胶色谱分离双黄酮类成分 ,用核磁和质谱等谱学方法确定化合物的结构。结果 分离并鉴定了 4个双黄酮类化合物 daphnodorins A- D1 ( ～ )。结论 首次从祖师麻中得到化合物 daphnodorins A- D1 ,这类结构的双黄酮化合物目前仅发现于该属植物。

江南卷柏中双黄酮类化学成分研究

目的研究江南卷柏中的双黄酮类成分。方法利用色谱法对江南卷柏75%醇提部分的化学成分进行系统分离纯化,利用理化性质及核磁共振图谱等手段对分离得到的单体化合物进行结构鉴定。结果从江南卷柏中分离得到了5个化合物,分别为穗花杉双黄酮(ametoflavone,1),罗巴斯塔双黄酮-4′-甲醚(4′-O-methylrobustafla-vone,2),穗花杉双黄酮-4′-甲醚(4′-O-methylametoflavone,3),穗花杉双黄酮-7-甲醚(7-O-methylametoflavone,4),7,4′-二甲氧基穗花杉双黄酮(7,4′-di-O-methylametoflavone,5)。结论其中化合物4为首次从江南卷柏中分离得到。

卷柏中双黄酮类化学成分及卷柏属该类化合物的核磁共振特征

目的对卷柏属双黄酮类化合物的核磁共振特征进行归纳。方法应用核磁共振波谱法对卷柏[Selaginellatamariscina(Beauv.)Spring.]50%乙醇提取物中分离得到的5个双黄酮类化合物进行结构鉴定,并结合相关文献对卷柏属双黄酮类化合物的核磁共振特征进行归纳总结。结果首次初步归纳出卷柏属双黄酮类化合物核磁共振碳谱和氢谱的特征。结论通过总结卷柏属双黄酮类化合物的核磁共振特征规律,为快速鉴定该类化合物的结构以及进行核磁数据的归属提供依据。

石上柏双黄酮类和酚酸类成分体外抗氧化和抗肿瘤活性研究

目的：研究石上柏双黄酮类和酚酸类成分体外抗氧化和抗肿瘤活性。方法：从石上柏中分离出的穗花杉双黄酮、扁柏双黄酮、银杏双黄酮、莽草酸、丁香酸及咖啡酸取适量,配置成不同浓度的溶液（20、40、60、80、100、120μg/m L）。以维生素C、槲皮素为对照品;采用1,1-二苯基-2-苦基苯肼（DPPH）、2,2＇-联氨-双（3-乙基苯并噻唑啉-6-磺酸）二氨盐（ABTS）自由基清除法和铁离子还原能力（FRAP）实验,分别考察每个化合物的抗氧化活性。通过MTT实验,以鼻咽癌CNE-1细胞株和CNE-2细胞株为对象,以顺铂为对照品,考察每个化合物的抗肿瘤活性。结果：抗氧化活性顺序：扁柏双黄酮〉银杏双黄酮〉穗花杉双黄酮〉丁香酸〉咖啡酸〉莽草酸;抗肿瘤活性顺序：扁柏双黄酮〉银杏双黄酮〉穗花杉双黄酮〉丁香酸〉咖啡酸〉莽草酸。结论：石上柏双黄酮类的抗氧化活性和抗肿瘤活性均强于酚酸类。