用户名: 密码: 验证码:
三种菊科植物及一种瑞香科植物化学成分研究
详细信息    本馆镜像全文|  推荐本文 |  |   获取CNKI官网全文
摘要
目的:第一部分,菊科橐吾属Ligularia Cass.植物棉毛橐吾Ligulariavellerea在民间用于治疗肝炎,为了探究棉毛橐吾中的功效物质基础,曾有人从棉毛橐吾中分离鉴定出20个化合物,为了更深入地研究棉毛橐吾中的活性成分,本文再次对该植物进行了化学成分研究;第二部分,离舌橐吾生长在海拔1400-3300米的河边、山坡及树林里,主要分布我国的云南西北部、四川、贵州、湖北西部、甘肃西南部和陕西南部,在民间主要作治疗流行性感冒、咳嗽、溃疡和肺结核等症,至今为止,文献记载已从离舌橐吾中分离得到多个艾里莫芬烷类倍半萜化合物,我们对采自河南省伏牛山系的该植物(本山系的该植物未有人研究过)进行了再研究,拟从中分离得到不同的活性单体成分;第三部分,两似蟹甲草为菊科蟹甲草属植物,蟹甲草属植物广泛分布于亚洲东北部及美洲,该属大约50种分布在中国,其中26种作为传统药物用于治疗支气管炎、关节炎及咳血等症,我们系统查阅了美国化学文摘,未发现对两似蟹甲草的化学成分的任何研究,而蟹甲草属与橐吾属在植物分类学上有很近的亲缘关系,蟹甲草属很多植物含有丰富的艾里莫芬烷型倍半萜,于是为了研究该植物可能的物质基础及丰富植物化学分类学的内容,我们对其进行了化学成分的研究;芫花为常用中药,为瑞香科瑞香属植物芫花Daphne genkwa Sieb.et Zucc.的花,性辛、温,有毒,有泻水逐饮、解毒之功效,但该药材的质量标准研究迄今还没有,所以我们对芫花的化学成分进行了系统研究,作为芫花药材质量标准研究的一部分内容。
     方法:应用硅胶、Sephadex LH-20、MCI gel HP-40P、Toyopearl HW 40(c)、反相硅胶等多种分离技术,对以上四种植物中的化学成分进行分离,并利用现代波谱技术包括~1H NMR、~(13)C NMR、2D NMR及MS等对单体化合物进行结构鉴定,采用MTT法对离舌橐吾中得到的部分化合物进行了抗肿瘤活性的初步筛选。
     结果:共从四种植物中分离出51个化合物,从棉毛橐吾中分离鉴定出27个单体化合物:1,5-二咖啡酰奎宁酸(Ⅰ-1),3,5-二咖啡酰奎宁酸(Ⅰ-2),艾里莫芬-7(11)-烯-12,8α(14β,6α)-二内酯(Ⅰ-3),对羟基苯乙酮(Ⅰ-4),7-羟基香豆素(Ⅰ-5),3,4-二羟基苯乙酮(Ⅰ-6),4-甲氧基-2',4',3-三羟基-查耳酮(Ⅰ-7),2',4',4-三羟基-查耳酮(Ⅰ-8),4'-甲氧基-7,3'-二羟基黄酮(Ⅰ-9),4-[(3,4-二羟基)-桂皮酰基]-桂皮酰基甲酯(Ⅰ-10),对羟基桂皮酸甲酯(Ⅰ-11a),对羟基桂皮酸(Ⅰ-11b),Ⅰ-12 2,5-二羟基-6,7-二甲基-萘醌(Ⅰ-12),4-O-咖啡酰奎宁酸(Ⅰ-13),3,4-二羟基桂皮酸(Ⅰ-14),6,7-二羟基香豆素(Ⅰ-15),3-O-咖啡酰奎宁酸(Ⅰ-16),8β-甲氧基埃里莫芬-7(11)-烯-12,8α(14β,6α)-二内酯(Ⅰ-17),雅槛蓝型艾里莫芬-14β,6α-内酯(Ⅰ-18),顺芷酸(Ⅰ-19),β-谷甾醇(Ⅰ-20),8β-羟基艾里莫芬-7(11)-烯-12,8α(14β,6α)-二内酯(Ⅰ-21),1-甘油醇十六碳酸酯(Ⅰ-22),胡萝卜苷(Ⅰ-23),十六碳酸(Ⅰ-24),十九碳酸甲酯(Ⅰ-25),艾里莫芬-7(11),9-二烯-12,8α(14β,6α)-二内酯(Ⅰ-26);从离舌橐吾中分离鉴定了10个化合物:1,3-二咖啡酰奎宁酸(Ⅱ-1),1,5-二咖啡酰奎宁酸(Ⅱ-2),艾里莫芬烷-6-烯-11-醇(Ⅱ-3),β-谷甾醇(Ⅱ-4),艾里莫芬-6α-羟基-8α,12-内酯(Ⅱ-5),10β-氢-6β,8β-二羟基艾里莫芬-8α,12 -内酯(Ⅱ-6),10α-氢-6α,8α-二羟基艾里莫芬-8β,12 -内酯(Ⅱ-6a),艾里莫芬烷-1(10)-烯-3-氧-11-醇(Ⅱ-7),(7α,9α,10α)-9α,10α-环氧-艾里莫芬烷-11-醇(Ⅱ-8),10α,11-内过氧桥-1(2)-烯-7α-氢艾里莫芬烷(Ⅱ-9);从两似蟹甲草中分离鉴定了4个化合物,包括两个对映贝壳杉烷二萜(Ⅲ-2和3),β-谷甾醇(Ⅲ-1)及1个甘油醇酯(Ⅲ-4);从芫花中分离得到10个化合物:异西瑞香素(Ⅳ-1),5,7,3',4'-四羟基黄酮(Ⅳ-2),5,7,4'-三羟基黄酮(Ⅳ-3),5,3',4'-三羟基黄酮(Ⅳ-4),4',7-二甲氧基-5-羟基黄酮(Ⅳ-5),二十八碳烷(Ⅳ-6),三十二碳烷(Ⅳ-7),4S,7S-金色酰胺醇酯(Ⅳ-8),7-甲氧基-4',5-二羟基黄酮(Ⅳ-9),β-谷甾醇(Ⅳ-10)。
     结论:从棉毛橐吾中分离鉴定的27个化合物中,2个为新化合物(Ⅰ-10和12),首次报道18个;从离舌橐吾中分离鉴定的10个化合物中,新化合物4个(Ⅱ-3,6a,8,9)及1个新天然产物(Ⅱ-7),除了Ⅱ-4外其它化合物都是首
     次从该植物中得到;从两似蟹甲草中分离得到的4个化合物,都为首次从两似蟹甲草中得到;从芫花中分离得到10个化合物,其中2个化合物(Ⅳ-6,7)为首次报道,并利用二维核磁谱对化合物Ⅳ-8的~1HNMR和~(13)CNMR数据进行了全部归属,对离舌橐吾中部分化合物活性测试,结果发现化合物Ⅱ-3对肺癌细胞(A849)有较强的抑制作用(IC_(50)值1.93μg/mL)。
Objective:The first part,Ligularia vellerea(Ligularia genus of Compositae) was used to deal with hepatitis as a folk medicine.For studying the material foundation of Ligularia vellerea,someone had isolated and identified 20 compounds from it.It was reinvestigated for more knowledge.The second part,the plant Ligularia veitchiana grows aside the rivers,hillsides,woods in the elevation.The plant was disributed in the northemwest of Yunnan,Sichun,Guizhou,the west of Hubei,the southernwest of Gansu,the south of Shanxi.It was used to deal with the diseases such as influenza,cough,ulcer and pulmonary tuberculosis as a folk medicine.Up to now,Many eremophilane-type sesquiterpenes were isolated from the plants.We reinvestigated it from Funiu Mountains of Henan Province(the plant of the Mountains was not studied),to plan to isolate different active compounds.The third part,Cacalia ambigua belongs to Cacalia genus(Compositae).The Cacalia genus was distributed in easternnorth of Asia and America.50 species of the genus were grown in China,among them,26 species were used to cure tracheitis,arthritis and cough and so on.We systematically consult the Scifinder data and find no results about the chemical research of Cacalia ambigua.The two genus of Cacalia and Ligularia have kinsfolk relationship on plant taxalogy.Many plants of Cacalia genus have a number of eremophilane-type sesquiterpenoids.To search for the material foundation of this plant and enlarge the knowledge of plant chemotaxology,we studied the chemical constituents.The fourth part,the flowers of Daphne genkwa Sieb.et Zucc. (Thymelaeaceae) were used to detoxify and to release the unneccessary water of body as the common traditional chinese medicine.The quality standard of this medicine has not been worked out.So we studied on the chemical constituents that could be part of study on medicinal quality standard of yuanhua.
     Methods:We used all kinds of modern chromatographic techniques including silica gel,Sephadex LH-20,MCI gel CHP-40P,Toyopearl HW-40(C) and RP-18 and so on to isolate the chemical constituents of the four plants,and then we identified the compounds and assigned the spectral data of them by modern spectroscopic techniques including ~1H NMR,~(13)C NMR,2D NMR and MS.Anticancer activity of several compounds from Ligularia veitchiana were screened by MTT.
     Results:51 compounds were isolated from these four plants.Among them,27 compounds from Ligularia vellerea were isolated and determined:1, 5-dicaffeoylquinic acid(Ⅰ-1),3,5-dicaffeoylquinic acid(Ⅰ-2),eremophil-7(11)-en-12, 8α(14β,6α) -dioxide(Ⅰ-3),p- hydroxyacetophenone(Ⅰ-4),7-hydroxycoumarin(Ⅰ-5),3, 4- dihydroxyacetophenone(Ⅰ-6),4-methoxy-2',4',3-trihydroxy-chalone (butein-4-methyl ester)(Ⅰ-7),2',4',4-trihydroxy-chalone(Ⅰ-8),4'-methoxy-7, 3'-dihydroxyflavone(Ⅰ-9),4-[(3,4-dihydroxyl)-cinnamyl]-cinnamyl methyl ester(Ⅰ-10),p-hydroxycoumaric acid methyl ester(Ⅰ-11a),p-hydroxycoumaric acid(Ⅰ-11b),2,5-dihydroxyl-6,7-dimethyl-naphthoquinone(Ⅰ-12),4-O-caffeoylquinic acid(Ⅰ-13),3,4-dihydroxycoumaric acid(Ⅰ-14),6,7-dihydroxycoumarin(Ⅰ-15), 3-O-caffeoylquinic acid(Ⅰ-16),8β-methoxyeremophil-7(11)-en-12,8α(14β,6α) -dioxide(Ⅰ-17),furoeremophil-15β,6α-oxide(Ⅰ-18),tiglic acid(Ⅰ-19),β-sitosterol (Ⅰ-20),8β-hydroxyeremophil-7(11)-en-12,8α(14β,6α) -dioxide(Ⅰ-21),1-glycerol palmitic acid ester(Ⅰ-22),Ⅰ-23 Daucosterol(I-23),Palmitic acid(Ⅰ-24),1-25 Nonadecanoic acid methyl ester(Ⅰ-25),eremophil-7(11),8-dien-12,8α(14β,6α) -dioxide(Ⅰ-26).
     10 compounds from Ligularia veitchiana were isolated and determined:1,3-dicaffeoylquinic acid(Ⅱ-1),1,5- dicaffeoylquinic acid(Ⅱ-2), eremophilan-6-en-11-ol(Ⅱ-3),β-sitosterol(Ⅱ-4),eremophil-6α-hydroxy-8α,12-olide (Ⅱ-5),10β-H-6β,8β-dihydroxyeremophil-8α,12 -oxide(Ⅱ-6),10α-H-6α, 8α-dihydroxyeremophil-8β,12 -oxide(Ⅱ-6a),1(10)-en-3-oxoeremophilan-11-ol(Ⅱ-7), (7α,9α,10α)-9,10-epoxy- eremophilan-11-ol(Ⅱ-8), 10α,11-endo-peroxide-1(2)-en-7α-hydroeremophilane(Ⅱ-9).
     4 compounds from Cacalia ambigua were isolated,ingcluding 2 ent-kaurane-type diterpenes(ent-kaur-16-en-19-oic acid(Ⅲ-2) and 13,β-kanr-16β-ol (Ⅲ-3)),β-sitosterol(Ⅲ-1) and 1 glycerol ester(1-glycerol cerotic acid ester,Ⅲ-4 ),
     10 compounds from Daphne genkawa were isolated:daphnoretin(Ⅳ-1),5,7,3', 4'-tetrahydroxyflavonone(Ⅳ-2),5,7,4'-trihydroxyflavonone(Ⅳ-3),5,3', 4'-hydroxyflavonone(Ⅳ-4),4',7-dimethoxy-5-hydroxyflavonone(Ⅳ-5), Octacosane(Ⅳ-6),Dotriacontane(Ⅳ-7),4S,7S-aurantiamide acetate(Ⅳ-8), 7-methoxy-4',5-dihydroxyflavonone(Ⅳ-9),β-sitosterol(Ⅳ-10).
     Conclusions:Among 27 compounds from Ligularia vellerea,2 of them were new(Ⅰ-10 and 12),18 of them were isolated from the plant for the first time.Among 10 compounds from Ligularia veitchiana,4 of them were new(Ⅱ-3,6a,8,9) and one(Ⅱ-7) was natural product,others except forⅡ-4 were isolated from the plant for the first time.4 compounds from Cacalia ambigua were isolated for the first time. Among 10 compounds from Daphne genkawa,2 of them(Ⅳ-6 and 7) were isolated from the plant for the first time.~1H NMR and ~(13)C NMR data ofⅣ- 8 were assigned by 2D NMR.The results of the bioactivity test for the several compounds from Ligularia veitchiana showed thatⅡ-3 can restrain the lung cancer cells(A849)(IC_(50) value 1.93μg/mL).
引文
[1]伏开周,赵毅民,张自萍.橐吾属植物的研究进展.天然产物研究与开发,2007,19,346.
    [2]张达治,余国奠,张勉,等.橐吾属植物药用研究概况.中国野生植物资源,2003,22(2),4.
    [3]檀爱民.橐吾属四种药用植物的化学成分研究.中国药科大学博士学位论文.2002,pp3.
    [4]吴秋红.木里橐吾化学成分及生物活性研究.兰州大学硕士学位论文.2006,pp5.
    [5]林启寿.中草药成分化学,北京:科学出版社.1977,pp153.
    [6]李云森.橐吾属四种药用植物的倍半萜类及其生物活性研究.中国药科大学博士论文.2002,pp23.
    [7]Ayano Naoe,Masami Ishibashi,Yuldnori Yamamoto,Cribrarione A,a new antimicrobial naphthoquinone pigment from a myxomycete Cribraria purpurea.Tetrahedron,2003,59,3433.
    [8]Andree Camat,Annie Heitz,Didier Fraisse,et al.Fitoterapia,2000,71,587.
    [9]Jiri Slanina,Eva Taborska,Hana Bochorakova,et al.New and facile method of preparation of the anti-HIV-1 agent,1,3-dicaffeoylquinic acid.Tetrahedron Letters,2001,42,3383.
    [10]李云森,罗士德,张勉,等.棉毛橐吾的化学成分.中国中药杂志,2001,26(12),835.
    [11]殷志琦,巢剑非,张雷红,等.构树化学成分研究.天然产物研究与开发,2006,18,420.
    [12]李俊,李甫,陆圆圆,等.满山香子抗炎成分研究.中国药学杂志,2007,42(4),225.
    [13]陈青,杨小生,朱海燕,等.贵州产白刺花种子的化学成分.研究中草药.2006,37(7).986.
    [14]Huan-Huan Wei,Ping Wu,Xue-Jun Ge,et al.Chemical constituents of the seeds of Ammopiptanthus(Leguminosae) and their systematic and ecological significance.Biochemical Systematcs and Ecoloy,2007,35,274.
    [15]郑俊霞,王乃利,陈海峰,等.翠云草中酚性成分的分离与鉴定.中国药物化学杂志,2007,17(5),302.
    [16]Nobuji Nakatani,Shinichi Kayano,Hiroe Kikuzaki,et al.Identification,Quantitative Determination and Antioxidative Activities of Chlorogenic Acid Isomers in Prune(Prunus domestica L.).J.Agric.Food Chem.,2000,48,5512.
    [17]吴霞,刘净,于志斌,等.薰衣草化学成分的研究.化学学报,2007,65(16),1649.
    [18]汤海峰,易杨华,姚新生,等.褐藻铁钉菜化学成分的研究(Ⅱ).中国海洋药物,2003,22(4),8.
    [19]武子敬,杨小生,朱海燕.滇木姜子化学成分初步研究.贵州化工,2007,32(1),15.
    [20]宋福行,范晓,徐秀丽,等.褐藻叉开网翼藻化学成分研究.中国中药杂志.2006,31,125.
    [21]李瑞芬,周玉枝,乔莉,等.蒙古黄芪化学成分的分离与鉴定.沈阳药科大学学报,2007,24(1),20.
    [22]Yu Zhao,Zhong-Jian Jia,Hai-Ruo Peng.EIGHT NEW EREMOPHILANE DERIVATIVES FROM THE ROOTS OF LIGULARIA PRZEWALSKII.Journal of Natural Products,1995,58(9),1358.
    [1]丁宝章,王遂义主编.河南植物志(第三册)郑州:河南科学技术出版社.1996,pp668.
    [2]中国科学院植物研究所主编.中国高等植物图鉴(第四册).北京:科学出版社.1994,pp 587.
    [3]Z-J Jia,Y Zhao,R-X Tan,et al.Sesquiterpenes and other constituents from Ligularia veitehiana.Phytochemistry,1992,31(1),199.
    [4]Zhong-Jian Jia,Yu Zhao,Ren-Xiang Tan.New eremophilane type laetones from the roots of Ligularia veiehiana.Planta Mediea,1992,58,365.
    [5]Y Zhao,Z-J Jia,R-X Tan,et al.Eremophilanolides from the roots of Ligularia veitchiana.Phytochemistry,1992,31(8),2785.
    [6]Yu Zhao,Zhong-Jian Jia,Ren-Xiang Tan.New eremophilanolides from Ligularia veiehiana.Chinese Chemical Letters,1992,3,35.
    [7]Yu Zhao,Zhong-Jian Jia.New sesquiterpenes from Ligularia veichiana.Chinese Chemical Letters,1993,4,323.
    [8]Zhong-Jian Jia,Yu Zhao,Ren-Xiang Tan.New Sesquiterpenes from the Roots of Ligularia veitchiana.Journal of Natural Products,1993,56,494.
    [9]Yu Zhao,Zhong-Jian Jia,Li Yang.Novel sesquiterpenes from Ligularia veichiana.Planta medica,1994,60,91.
    [10]Yu Zhao,Hai-Ruo Peng,Zhong-Jian Jia.Six New Eremophilane Derivatives from Two Ligularia Species.Journal of Natural Products,1994,57,1626.
    [11]Yu Zhao,Simon Parsons,Bruce A.Smart,et al.Eremophilane Derivatives with a Novel Carbon Skeleton from Ligularia veitchiana.Tetrahedron,1997,53,6195.
    [12]Ying Wang,Cheng-Shan Yuan,Yi-Feng Han,et al.Two New Sesquiterpenes from Ligularia veitchiana.Chinese Chemical Letters,2002,13,1069.
    [13]Ying Wang,Cheng-Shan Yuan,Yi-Feng Hart,et al.Die Pharmazie,2003,58,349.
    [14]HuaYang,Qi-Xiu Zhu,Zhong-Jian Jia.A New Eremophilanoid Sesquiterpene from Senecio Oldhamianus.Chinese Chemical Letters,2002,13,139.
    [15]Yasunori Yaoita,Masao Kikuchi.Struetures of new eremophilane derivatives from the rhizomes of Petasites japonieus Maxim.Chemical and Pharmaceutical Bulletin,1995,43,1738.
    [16]K.Naya,R.Kanazawa,M.Sawada.Bulletin of the Chemical Society of Japan,1975,48,3220.
    [17]吴秋红.木里橐吾化学成分及生物活性研究.兰州大学硕士学位论文.2006,16.
    [18]Qiu-Hong Wu,Chun-Mei Liu,Yan-Jun Chen,et al.Terpenoids from the Roots of Ligularia muliensis.Helvetica Chimica Acta,2006,89,915.
    [19]施树云.黑紫橐吾和蒙古蒲公英的化学成分研究及臭灵丹中异绿原酸的色谱制备研究.浙江大学博士学位论文.2007,pp76.
    [1]中国科学院植物研究所主编.中国高等植物图鉴(第四册).北京:科学出版社.1994,pp 553.
    [2]侯宽昭.中国种子植物科属词典(第二版).北京:科学出版社,1998,pp75.
    [3]中国药材公司.中国中药资源制药.北京:科学出版社,1994,pp1271.
    [4]江苏新医学院.中药大辞典[M](上).人民卫生出版社.1977,pp22.
    [5]Yang-Chang Wu,Yu-Chun Hung,Fang-Rong Chang,et al.Identification of ent-16,17-Dihydroxykauran-19-oic Acid as an Anti-HIV Principle and Isolation of the New Diterpenoids Annosquamosins A and B fi'om Annona squamosa.J.Nat.Prod.,1996,59,635.
    [6]Raymond M.Carman.Phyllocladan-16 β -ol(13 β -Kauran-16 β -ol).Aust.J.Chem.,1981,34,923.
    [1]丁宝章,王遂义主编.河南植物志(第三册).郑州:河南科学技术出版社.1996,pp 71.
    [2]中国科学院植物研究所主编.中国高等植物图鉴(第二册).北京:科学出版社.1994,pp 951.
    [3]《全国中草药汇编》编写组编.全国中草药汇编(上册).北京:人民卫生出版社.1975,pp 779.
    [4]张保献,原思通,张静修,等.芫花的现代研究概况.中国中医药信息杂志.1995,2(10),21.
    [5]Wei-fa Zheng,Feng Shi.Isolation and identification of a new dicoumarin from the roots of Daphne genkwa.药学学报,2004,39,990.
    [6]徐小花,杨念云,钱士辉,等.女贞子黄酮类化合物的研究.中草药.2007,30(5),538.
    [7]王彩芳,胡晓娟,谢松梅.芫花叶的黄酮类化学成分分析.郑州大学学报(医学版).2003,38(1),107.
    [8]彭金咏,范国荣,吴玉田.白花败酱草黄酮类成分的高速逆流色谱快速制备.中国药学杂志,2006,41(13),977.
    [9]于江泳,张思巨,刘丽.肖菝葜化学成分的研究.中国药学杂志,2005,40(1),19.
    [10]张前军,杨小生,朱海燕,等.假木豆脂溶性成分研究.贵州大学学报(自然科学版),2006,23(3),270.
    [11]王明焱,苏镜娱,曾陇梅,等.用2D NMR确定金色酰胺醇酯的结构.分析测试学报,2000,19,45.
    [12]张薇,张卫东,李廷钊,等.毛瑞香化学成分研究.中国中药杂志,2005,30(7),513.
    [1]W.KISIEL,B.BARSZCZ.SESQUITERPENE LACTONE GLYCOSIDES FROM CREPIS PYRENAICA.Phytochemistry,1995,39,1395.
    [2].G(U|¨)LACTI TOPCU,SEVIL(O|¨)KS(U|¨),WERNER HERZ,et al.STRUCTURALLY RELATED GUAIANOLIDES FROM INULATHAPSOIDES.Phytochemistry,1995,40,1717.
    [3]MILKA N.TODOROVA,MARIA L.KRASTEVA.SESQUITERPENE LACTONES FROMARTEMISIA LERCHIANA.Phytochemistry,1996,42,1231.
    [4]W.KISIEL,B.BARSZC.SESQUITERPENE LACTONES FROM CREPIS RHOEADIFOLIA.Phytochemistry,1996,43,823.
    [5]HALAS.AL-EASA,ABDEL-FATTAH M.RIZK,AHMED A.AHMED.GUAIANOLIDES FROM PICRIS RADICATA.Phytochemistry,1996,43,423.
    [6]NEZHUN GOREN,EL1F TAHTASAKAL,MAUSZ KRAWEC,et al.A GUAIANOLIDE FROM TANACETUM ARGENTEUM SUBSP.FLABELLIFOLIUM.Phytochemistry,1996,42,757.
    [7]ALICIA BARDON,LUZ CARDONA,C(E|¨)SAR A.N.,et al.15-NORGUAIANOLIDES AND GERMACRANOLIDES FROM MIKANIA MENDOCINA.Phytochemistry,1996,41,845-849.
    [8]FRANCISCO A.MACIAS,ASCENSION TORRES,JOSE M.G,et al.POTENTIAL ALLELOPATHIC SESQUITERPENE LACTONES FROM SUNFLOWER LEAVES.Phytochemistry,1996,43,1205.
    [9]Luls R.HERNANDEZ,CESARA.N.CATALAN,CARLOS M.CERDA-GARCIA-ROIAS et al.SESQUITERPENE LACTONES FROM STEVIA VAGA.Phytochemistry,1996,42,1369.
    [10]Abimael D.Rodriguez,Anna Boulanger.Americanolides A-C,New Guaianolide Sesquiterpenes from the Caribbean Sea Plume Pseudopterogorgia americana.J.Nat.Prod.,1996,59,653.
    [11]V.Bulatovic,V.Vajs,S.Macura,et al.Highly Oxygenated Guaianolides from Anthemis carpatica.J.Nat.Prod.,1997,60,1222.
    [12]WANDA KISIEL,BARBARA BARSZCZ,EDWARD SZNELER.SESQUITERPENE LACTONES FROM LACTUCATA TARICA.Phytochemistry,1997,45,365.
    [13]WANDA KISIEL,BARBARA BARSZCZ.MINOR SESQUITERPENE LACTONES FROM LACTUCA VIROSA.Phytochemistry,1997,46,1241.
    [14]OTMAR SPRING,NORBERT HEIL,BERNHARD VOGLER.SESQUITERPENE LACTONES AND FLAVANONES IN SCALESIA SPECIES.Phytochemistry,1997,46,1369.
    [15]ZAIDA N.J.DE HERNANDEZ,LUIS R.HERNZANDEZ A.N.CATALAN,THOMAS E.GEDRIS et al.GUAIANOLIDES AND GERMACRADIENOLIDES FROM STEVIA SANGUINEA.Phytochemistry,1997,46,721.
    [16]MAURIZIO BRUNO,MARIA L.BONOI,NADIA VASSALLO,et al.GUAIANOLIDES AND OTHER TERPENOIDS FROM ANTHEMIS AETNENSIS.Phytochemistry,1997,45,375.
    [17]KAMEL MEDJROUBI,FADILA BENAYACHE,SMAIR BENAYACHE,et al.GUAIANOLIDES FROM CENTAUREA MUSIMOMUM.Phytohemistry,1997,45,1449.
    [18]BASMA A.BAI,BOUL,AHMED A.AHMED,et al.A GUAIANOLIDE AND A GERMACRANOLIDE FROM ACHILLEA SANTOLINA.Phytochemistry,1997,46,1045.
    [19]AMR M.HELAL,NORIO NAKAMIJRA,MESELHY R.MESELHY,et al.GUAIANOLIDES FROM CENTAUREA SCOPARIA.Phytochemistry,1997,45,551.
    [20]Nezhun G6ren,Elif Tahtasakal,Mariusz Krawiec,et al.Guaianolides from Tanacetum argenteum Subsp.canum var.canum.J.Nat.Prod.,1998,61,560.
    [21]Charles L.Cantrell,Isabel S.Nunez,Jose Castaneda-Acosta,et al.Antimycobacterial Activities of Dehydrocostus Lactone and Its Oxidation Products.Journal of Natural Products,1998,61,1181.
    [22]B.R.CHHABRA,S.GUPTA,M.JAIN,et al.SESQUITERPENE LACTONES FROM SAUSSUREA LAPPA.Phytochemistry,1998,49,801.
    [23]MAURIZIO BRUNO,ANTONELLA,NELLY A.ARNOLD,et al.SESQUITERPENE LACTONES FROM ANTHEMIS PLUTONIA.Phytochemistry,1998,49,1739.
    [24]ALFREDO ORTEGA,RUBEN A,TOSCANO et al.COSTIC ACID GUAIANYL ESTER AND OTHER CONSTITUENTS OF PODACHAENIUM EMINENS.Phytochemistry,1998, 49,1085.
    [25]CHRISTIAN ZIDORN,ERNST P.ELLMERER-MtiLLERf',HERMANN STIJPPNER.GUAIAN-5,12-OLIDES FROM LEONTODON HISPIDUS.Phytochemistry,1998,49,797.
    [26]DIAA T.A.YOUSSEF.SESQUITERPENE LACTONES OF CENTAUREA SCOPARIA.Phytochemistry,1998,49,1733.
    [27]Maurizio Bruno,Nadia Vasallo,Caterina Fazio,et al.Sesquiterpene lactones of two centaurea species from Sicily.Biochemical Systematics and Ecology,1998,26,801.
    [28]MILKA N.TODOROVA,MARIA L KRASTEVA,MIGLENA M MARKOVA,et al.TERPENOIDS FROM ACHILIEA CLYPEOLATA.Phytochemistry,1998,49,2371.
    [29]Jasonol.A Rare Tricyclic Eudesmane Sesquiterpene and Six other New Sesquiterpenoids from Jasonia candicans.Tetrahedron,1998,54,8141.
    [30]R.X.TAN,H.Q.TANG,J.HU,et al.LIGNANS AND SESQUITERPENE LACTONES FROM ARTEMI SIEVERSIANAAND INULA RACEMOSA.Phytochemistry,1998,49,157.
    [31]Nezhun G(o|¨)ren,Elif Tahtasakal,Mariusz Krawiec,et al.Guaianolides from Tanacetum argenteum Subsp.canum var,canum..J.Nat.Prod.,1998,61,560.
    [32]Hao Li,Jun Cai Meng,Christopher H.K.Cheng,et al.New Guaianolides and Xanthine Oxidase Inhibitory Flavonols from Ajania fruticulosa.J.Nat.Prod.,1999,62,1053.
    [33]S.Glasl,A.Presser,I.Wemer,et al.Two proazulenes from Achillea ceretanica Sennen.Phytochemistry,1999,50,629.
    [34]Nisar Ullah,Saeed Ahmed,Zaheer Ahmed,et al.Dimeric guaianolides from Daphne oleoides.Phytochemistry,1999,51,559.
    [35]Christian Zidom,Ernst P.Ellmerer-Miiller,Hermann Stuppner.Guaianolides from Calycocorsus stipitatus and Crepis tingitana.Phytochemistry,1999,50,1061.
    [36]Vlatka Vajs,Nina Todorovic,Marina Ristic,et al.Guaianolides from Centaurea nicolai:antifungal activity.Phytochemistry,1999,52,383.
    [37]Vlatka Vajs,Vanja Bulatovic,Katarina Fodulovic-Savikin,et al.Highly oxygenated guaianolides from Anthemis cretica subsp.cretica.Phytochemistry,1999,50,287.
    [38]Viqar Uddin Ahmad,Shazia Yasmeen,Zulfiqar Ali,et aL A New Guaianolide from Taraxacum wallichii.J.Nat.Prod,2000,63,1010.
    [39]Elena Cartagena,Alicia Bardon,Cesar A.N.Catalan,et al.Germacranolides and a New Type of Guaianolide from Acanthospermum Hispidum.J.Nat.Prod.,2000,63,1323.
    [40]Vlatka Vajs,Nina Todorovic,Vanja Bulatovic,et al.Further sesquiterpene lactones from Anthemis carpatica.Phytochemistry,2000,54,625.
    [41]Hocine Dendougui,Samir Benayache,Fadila Benayache,et al.Cormoly.Sesquiterpene lactones from Pulicaria crispa.Fitoterapia,2000,71,373.
    [42]Wanda Kisiel,Klaudia Zielinska.Guaianolides from Cichorium intybus and structure revision of Cichorium sesquiterpene lactones.Phytochemistry,2001,57,523.
    [43]Sabine Glasl,Armin Presser,Disan Gunbilig,et al.Highly hydroxylated guaianolides of Achillea asiatica and Middle European Achillea species.Phytochemistry,2001,58,1189.
    [44]J.C.Meng,Y.F.Hu,J.H.Chert,et al.Antifungal highly oxygenated guaianolides and other constituents from Ajania fruticulosa.Phytochemistry,2001,58,1141.
    [45]Karin Schorr,Alfonso J.Garcia-Pineres,Bettina Siedle,et al.Guaianolides from Viguiera gardneri inhibit the transcription factor NF-Kb.Phytochemistry,2002,60,733
    [46]M.Bruno,S.Rosselli,M.L.Bondi,et al.Sesquiterpene lactones of Anthemis alpestris.Biochemical Systematics and Ecology,2002,30,891.
    [47]Wanda Kisiel,Klandia Zielinska,Swati P.Joshi.Sesquiterpenoids and phenolics from Crepis mollis.Phytochemistry,2002,54,763.
    [48]Zhi Xin LIAO,Shu Lin PENG,Yao Zu CHEN,et al.A New Sesquiterpene Lactone of Notoseris henryi.Chinese Chemical Letters,2002,13,736.
    [49]Ho-Fai Wong,Geoffrey D.Brown.Dimeric Guaianolides and a Fulvenoguaianolide from Artemisia myriantha.J.Nat.Prod.,2002,65,481.
    [50]Fatima Hilmi,Otto Sticher,J(o|¨)rg Heilmann.New Cytotoxic 6,7-cis and 6,7-trans Configured Guaianolides from Warionia saharae.J.Nat.Prod.,2002,65,523.
    [51]Mi-Ran Kim,Chang-Soo Kim,Kyung-Hwa Hwang,et al.Isolation and Structures of Guaianolides from Carpesium macrocephalum.J.Nat.Prod.,2002,65,583.
    [52]Shujun Zhang,Jinlan Wang,Hongyan Xue,et al.Three New Guaianolides from Siyekucai (Ixeris chinenseis).J.Nat.Prod.,2002,65,1927.
    [53]Chang-Ming Sun,Wan-Jr Syu,Ming-Jaw Don,et al.Cytotoxic Sesquiterpene Lactones from the Root of Saussurea lappa.J.Nat.Prod.,2003,66,1175.
    [54]Ahmed A.Ahmed,Tamas Gati,Taha A.Hussein,et al.Ligustolide A and B,two novel sesquiterpenes with rare skeletons andthreel,10-seco-gnaianolidederivatives from Achillealignstica.Tetrahedron,2003,59,3729.
    [55]Fatima Hilmi,J(u|¨)rg Gertsch,Paul Bremner,et al.Cytotoxic versus Anti-Inflammatory Effects in HeLa,Jurkat T and Human Peripheral Blood Cells Caused by Guaianolide-Type Sesquiterpene Lactones.Bioorganic & Medicinal Chemistry,2003,11,3659.
    [56]Klaudia Michalska,Wanda Kisiel.Taxonomically significant gnaianolides from Taraxacum obovatum.Biochemical Systematics and Ecology,2004,32,765.
    [57]Maurizio Bruno,Sergio Rosselli,Antonella Maggio,et al.Cytotoxic Activity of Some Natural and Synthetic Guaianolides.J.Nat.Prod.,2005,68,1042.
    [58]Juan LI,Quan Xiang WU,Yan Ping SHI,et al.A New Sesquiterpene Lactone from Scorzonera anstriaca.Chinese Chemical Letters,2004,15,1309.
    [59]Min YANG,Zhong Jian JIA.A New Guaianolide from Saussurrea macrota.Chinese Chemical Letters.2004,15,417.
    [60]Ali Bentamene,Samir Benayache,Joel Creche,et al.A new guaianolide and other sesquiterpene lactones from Centaurea acaulis L.(Asteraceae).Biochemical Systematics and Ecology,2005,33,1061.
    [61]Naoto Osaki,Takashi Koyano,Thaworn Kowithayakorn,et al.Sesquiterpenoids and Plasmin-Inhibitory Flavonoids from Blumea balsamifera.J.Nat.Prod.2005,68,447.
    [62]Maurizio Bruno,Sergio Rosselli,Antonella Maggio,et al.Guaianolides from Centaurea babylonica.Biochemical Systematics and Ecology,2005,33,817.
    [63]Snezana Trifunovic,Ivana Aljancic,Vlatka Vajs,et al.Sesquiterpene lactones and flavonoids of Achillea depressa.Biochemical Systematics and Ecology,2005,33,317.
    [64]Antoaneta Trendafilova,Milka Todorova,Bozhanka Mikhova,et al.Sesquiterpene lactones from Achillea collina J.Becker ex Reichenb.Phytochemistry,2006,67,764..
    [65]Milka N.Todorova,Bozhanka Mikhova,Antoaneta Trendafilova,et al.Sesquiterpene lactones from Achillea asplenifolia.Biochemical Systematics and Ecology,2006,34,136.
    [66]Wanda Kisiel,Klaudia Miehalska.Matriearin-type guaianolides from Taraxacum bessarabicum and their chemotaxonomic significance.Biochemical Systematics and Ecology,2006,34,356.
    [67]Snezana Trifunovic,Vlatka Vajs,Zorica Juranic,et al.Cytotoxic constituents of Achillea clavermae from Montenegro.Phytochemistry,2006,67,887.
    [68]Milka Todorova,Antoaneta Trendafilova,Bozhanka Mikhova,et al.Terpenoids from Achillea distans Waldst.& Kit.ex Willed.Biochemical Systematics and Ecology,2007,35,852.
    [69]Yah Li,Chunlan Wang,Shunxing Guo,et al.Three guaianolides from Saussurea involucrata and their contentsdetermination by HPLC.Journal of Pharmaceutical and Biomedical Analysis,2007,44,288.
    [70]Milka Todorova,Antoaneta Trendafilova,Bozhanka Mikhova,et al.Chemotypes in Achillea collina based on sesquiterpene lactone profile.Phytochemistry,2007,68,1722.
    [71]Zhen Xue Zhang,Jin Zong You,Xin Sheng Yao.A new guaianolide from the roots of Valeriana fauriei Briq.Journal of Pharmaceutical Sciences,2007,(16),18.
    [72]Shujun Zhang,Ming Zhao,Liming Bai,et al.Bioactive Guaianolides from Siyekucai(Ixeris chinensis).J.Nat.Prod.,2006,69,1425.
    [73]Juan J.Rubal,Francisco M.Guerra,F.Javier Moreno-Dorado,et al.Sesquiterpenes from Thapsia nitida var.meridionalis,Thapsia nitida var.nitida..J.Nat.Prod.,2006,69,1566.
    [74]Qi Wang,Daofeng Chen.A Guaianolide Sesquiterpene,a Chromenone,and a Flavanone from Ligularia macrophylla.Helvetica Chimica Acta,2007,90,2432.
    [75]Heng-Xing Liang,Fu-Kai Bao,Xiao-Ping Dong,et al.Two New Antibacterial Sesquiterpenoids from Centipeda minima.CHEMISTRY & BIODIVERSITY,2007,4,2810.
    [76]Juan C.Oberti,Virginia E.Sosa.Crystal Structure and Stereochemistry of Achalensolide,a New Guaianolide from Stevia achalensis.J.Org.Chem.,1983,48,4038.
    [77]徐任生.天然产物化学(第二版).北京:科学出版社.2004,pp206.
    [78]Ilias Muhammad,Satoshi Takamatsu,Jaber S.Mossa,et al.Cytotoxic Sesquiterpene Lactones from Centaurothamnus maximus and Vicoa pentanema.Phytother.Res.,2003,17,168.
    [79] Mariane B. Fernandes, Marcus T. Scotti, Marcelo J. P. Ferreira, et al. Use of organizing maps and molecular descriptors to predict the cytotoxic activity of sesquiterpene lactones. European Journal of Medicinal Chemistry, 2008, xx, 1.
    [80] Marcus T. Scotti, Mariane B. Fernandes, Marcelo J. P. Ferreira, et al. Quantitative structure-activity relationship of sesquiterpene lactones with cytotoxic activity. Bioorganic & Medicinal Chemistry, 2007, 15, 2927.

© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号

地址:北京市海淀区学院路29号 邮编:100083

电话:办公室:(+86 10)66554848;文献借阅、咨询服务、科技查新:66554700