综述

青脆枝化学成分及其活性研究进展

  • 沈瑞池 ,
  • 吴美芳 ,
  • 何恩铭 ,
  • 陈德林 ,
  • 王 杰 ,
  • 何建章 ,
  • 周 爽
展开
  • (福建省亚热带植物研究所,福建省亚热带植物生理生化重点实验室,福建 厦门 361006)
沈瑞池,硕士,副研究员,从事天然药物开发利用研究。

收稿日期: 2016-05-24

  修回日期: 2017-01-19

  网络出版日期: 2016-12-10

基金资助

厦门市科技计划项目(3502Z20141041、3502Z20151245、3502Z20150057、3502Z20162010);厦门市重大科技创新平台项目(3502Z20131004);福建省亚热带植物研究所基金项目(2015S004、2015S005)

Research Progress on Chemical Constituents and Biological Activity of Nothapodytes nimmoniana

  • SHEN Rui-chi ,
  • WU Mei-fang ,
  • HE En-ming ,
  • CHEN De-lin ,
  • WANG Jie ,
  • HE Jian-zhang ,
  • ZHOU Shuang
Expand
  • (Fujian Institute of Subtropical Botany, Fujian Key Laboratory of Physiology and Biochemistry for Subtropical Plant, Xiamen 361006, Fujian China)

Received date: 2016-05-24

  Revised date: 2017-01-19

  Online published: 2016-12-10

摘要

喜树碱是已发现的唯一专门通过抑制拓扑异构酶Ⅰ发挥细胞毒性的天然植物成分,具有广谱抗肿瘤活性。青脆枝Nothapodytes nimmoniana含有多种喜树碱类化合物及其他活性成分,其中喜树碱、9-甲氧基喜树碱和羟基喜树碱含量最为丰富,是重要的药用植物。文中综述青脆枝主要化学成分、生物活性及其提取方法,并对青脆枝的应用前景作展望。

本文引用格式

沈瑞池 , 吴美芳 , 何恩铭 , 陈德林 , 王 杰 , 何建章 , 周 爽 . 青脆枝化学成分及其活性研究进展[J]. 亚热带植物科学, 2016 , 45(04) : 379 -385 . DOI: 10.3969/j.issn.1009-7791.2016.04.017

Abstract

Camptothecin (CPT) is a cytotoxic quinoline alkaloid which is only one specially inhibiting the DNA enzyme topoisomerase I (topo I), showes remarkable anticancer activity. There are many CPTs and other active ingredients in Nothapodytes nimmoniana, the contents of CPT, 9-methoxycamptothecin and hydroxycamptothecin in Nothapodytes nimmoniana are most abundant. N. nimmoniana have become an important medicinal plant. In this paper, the chemical constituents, their biological activity and extraction methods of N. nimmoniana were summarized. In addition, the development and utilization prospect of N. nimmoniana were introduced.

参考文献

[1] 郭瑞霞,李力更,王于方,霍长虹,付炎,王磊,史清文. 天然药物化学史话: 天然产物化学研究的魅力[J]. 中草药, 2015,46(14): 2019—2033.

[2] Govindachari T R, Viswanathan N. Alkaloids of Mappia foetida[J]. Phytochemistry, 1972,11(12): 3529—3531.

[3] Kepler J A, Wani M C, McNaull J N, Wall M E, Levine S G. Plant antitumor agents. IV. An approach toward the synthesis of camptothecin[J]. The Journal of Organic Chemistry,1969,34(12): 3853—3858.

[4] Hombe Gowda H C, Vasudeva R, Mathachen G P, Uma Shaanmer R, Ganeshaiah K N. Breeding types in Nothapodytes nimmoniana Graham.: An important medicinal tree[J]. Current Science, 2002,83(9): 1077—1078.

[5] Li H L. Flora of Taiwan (1st edition)[M]. Taipei: Epochpublishing Co., 1977,3: 648.

[6] Radhakrishnan H. Studies of Folkloric medicinal plants in Nilgiris district[D]. Coimbatore, India: Ph.D. Thesis, Bharathiar University, 1992.

[7] Wu T S, Leu Y L, Hsu H C, Ou L F, Chen C C, Chen C F, Ou J C, Wu Y C. Constituents and cytotoxic principles of Nothapodytes foetida[J]. Phytochemistry, 1995,39(2): 383—385.

[8] Wu T S, Chan Y Y, Leu Y L, Chern C Y, Chen C F. Nothapodytines A and B from Nothapodytes foetida[J]. Phytochemistry, 1996,42(3): 907—908.

[9] Ciddi V, Shuler M L. Camptothecine from callus cultures of Nothapodytes foetida[J]. Biotechnology Letters, 2000,22(2): 129—132.

[10] Srinivas K, Das B. 9-Methoxy-20-O-acetylcamptothecin, a minor new alkaloid from Nothapodites foetida[J]. Biochemical Systematics and Ecology, 2003,31(1): 85—87.

[11] 胡祖艳,范青飞,张玉梅,冯峰,杨俊林,宋启示. 青脆枝小枝的化学成分研究[J]. 天然产物研究与开发, 2014,26: 1605—1609.

[12] Wu S F, Hsieh P W, Wu C C, Lee C L, Chen S L, Lu C Y, Wu T S, Chang F R, Wu Y C. Camptothecinoids from the seeds of Taiwanese Nothapodytes foetida[J]. Molecules, 2008,13: 1361—1371.

[13] Ramesha B T, Amna T, Ravikanth G, Gunaga R P, Vasudeva R, Ganeshaiah K N, Uma Shaanker R, Khajuria R K, Puri S C, Qazi G N. Prospecting for camptothecines from Nothapodytes nimmoniana in Western Ghats, South India: Identification of high-yielding sources of camptothecin and new families of camptothecines[J]. Journal of chromatographic science, 2008,46(4): 362—368.

[14] Hosamani K M, Pattanashettar R S. Mappia foetida seed oil: A rich source of oil and moderate source of novel 3-keto-octadec-cis-15-enoic acid and its possible industrial utilization[J]. Industrial Crops and Products, 2005,22(2): 135—139.

[15] Padmanabha B V, Chandrashekar M, Ramesha B T, Hombe Gowda H C, Gunaga Rajesh P, Suhas S, Vasudeva R, Ganeshaiah K N, Uma Shaanker R. Patterns of accumulation of camptothecin, an anti-cancer alkaloid in Nothapodytes nimmoniana Graham., in the Western Ghats, India: Implications for identifying high-yielding sources of the alkaloid[J]. Current Science is an Indian, 2006,90(1): 95—100.

[16] 王玲丽,刘文哲. 不同种源喜树幼枝中喜树碱的含量[J]. 植物学通报, 2005,22(5): 584—589.

[17] Fulzele D P, Satdive R K. Distribution of anticancer drug camptothecinin Nothapodytes foetida[J]. Fitoterapia, 2005, 76(7-8): 643—648.

[18] Fulzele D P, Satdive R K. Comparison of techniques for the extraction of the anti-cancer drug camptothecin from Nothapodytes foetida[J]. The Journal of Chromatography A, 2005,1063: 9—13.

[19] Namdeo A G, Sharma A, Fulzele D P, Mahadik K R. Influence of geographical and climatic conditions on camptothecin content of Nothapodytes nimmoniana[J]. Records of Natural Products, 2010,4(1): 64—71.

[20] Namdeo A G, Sharma A. HPLC analysis of camptothecin content in various parts of Nothapodytes foetida collected on different periods[J]. Asian Pacific Journal of Tropical Biomedicine, 2012,2(5): 389—393.

[21] Aiyama R, Nagai H, Nokata K, Shinohara C, Sawada S. A camptothecin derivative from Nothapodytes foetida[J]. Phytochemistry, 1988,27(11): 3663—3664.

[22] Wall M E, Wani M C, Cook C E, Palmer K H, McPhail A T, Sim G A. Plant antitumor agents. I. The isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from Camptotheca acuminata[J]. Journal of the American Chemical Society, 1966,88(16): 3888—3890.

[23] Rastogi S, Joshi B, Fusaro G, Chellappan S. Camptothecin treatment does not induce migration of prohibitin and p53 to cytoplasm in untransformed cell lines[J]. The Journal of Biological Chemistry, 2006,281(5): 2951—2959.

[24] 沈荣,李学忠,周小平,丁卫祥,陈强,沈卉君. 喜树碱对炎症诱导的多巴胺能神经元损伤的保护作用[J]. 江苏医药, 2011,37(3): 269—271.

[25] Liu Y Q, Liu Z L, Tian X, Yang L. Anti-HSV activity of camptothecin analogues[J]. Natural Product Research, 2010,24(6): 509—514.

[26] Rao M, Zhang S, Dong J, Li S. Inhibition of hepatitis B virus replication by homoharringtonine, IFN-alpha_ (1b), hydroxycamptothecin and norfloxacin[J]. Virologica Sinica, 2005,21(3): 284—287.

[27] Shibahara S, Mukai S, Morisawa H, Nakashima H, Kobayashi S, Yamamoto N. Inhibition of human immunodeficiency virus (HIV-1) replication by synthetic oligo-RNA derivatives[J]. Nucleic Acids Research, 1989,17(1): 239—252.

[28] Li Y Y, Chen S W, Yang L M, Wang R R, Pang W, Zheng Y T. The anti-HIV actions of 7-and 10-substituted camptothecins[J]. Molecules, 2009,15(1): 138—148.

[29] Kitoh A, Nomura T, Kabashima K. TGFβ1, an epidermal controller of skin dendritic cell homeostasis[J]. Journal of Investigative Dermatology, 2013,133(1): 9—11.

[30] Liao N, Zhang P, Ao M, Wang J, Shi Y, Yu L. 9-methoxycamptothecin from Nothapodytes foetida induces apoptosis in murine sarcoma S180 cells[J]. Zeitschrift für Naturforschung C, 2011,66(9-10): 471—476.

[31] 肖坤福. 喜树碱的研究[J]. 新进展时珍国医国药, 2004,15(11): 786—789.

[32] 孙钰,冯新民,颜连启,蒋百川,虞堂云,王强,戴善和. 羟基喜树碱预防硬膜外粘连的有效性和安全性研究[J]. 临床骨科杂志, 2010,13(2): 214—217.

[33] 金创,李兵,霍焱,张本. 羟基喜树碱抑制大鼠角膜移植免疫排斥反应: 与环孢素A的比较[J]. 中国组织工程研究与临床康复, 2010,14(31): 5778—5780.

[34] Doh S H, Kim J H, Lee K M, Park H Y, Park C K. Retinal ganglion cell death induced by endoplasmic reticulum stress in a chronic glaucoma model[J]. Brain Research, 2010,1308: 158—166.

[35] Abcouwer S F, Marjon P L, Loper R K, Vander Jagt D L. Response of VEGF expression to amino acid deprivation and inducers of endoplasmic reticulum stress[J]. Investigative Ophthalmology & Visual Science, 2002,43(8): 2791—2798. 43: 2791—2798.

[36] Mathijssen R H J, Van Alphen R J, Verweij J, Loos W J, Nooter K, Stoter G, Sparreboom A. Clinical pharmacokinetics and metabolism of irinotecan (CPT-11)[J]. Clinical Cancer Research, 2001,7(8): 2182—2194.

[37] Demain A L, Vaishnav P. Natural products for cancer chemotherapy[J]. Microbial Biotechnology, 2011,4: 687–699.

[38] Lee D H, Kim S W, Bae K S, Hong J S, Suh C, Kang Y K, Lee J S. A phase I and pharmacologic study of belotecan in combination with cisplatin in patients with previously untreated extensive-stage disease small cell lung cancer[J]. Clinical Cancer Research, 2007,13(20): 6182—6186.

[39] Tang M M, Spanou Z, Tang H, Schibler F, Pelivani N, Yawalkar N. Rapid downregulation of innate immune cells, interleukin-12 and interleukin-23 in generalized pustular psoriasis with infliximab in combination with acitretin[J]. Dermatology, 2012,225(4): 338—343.

[40] 沈洁,王青松,许向阳, 周建平. 喜树碱类衍生物脂质体的研究进展[J]. 中国药科大学学报, 2007,38(4): 380—384.

[41] Sirikantaramas S, Asano T, Sudo H, Yamazaki M, Saito K. Camptothecin: therapeutic potential and biotechnology [J]. Current Pharmaceutical Biotechnology, 2007,8(4): 196—202.

[42] 白永花,宋启示. 马比木根中喜树碱和9-甲氧基喜树碱的HPLC分析[J]. 药物分析杂志, 2014,34 (1): 100—103.

[43] 王晶. 臭马比木中抗癌药效成分分布、制备及药理活性研究[D]. 武汉: 华中科技大学硕士学位论文, 2011.

[44] Hsiao H Y, Cheng T J, Yang G M, Huang I J, Chen R L. Determination of camptothecins in DMSO extracts of Nothapodytes foetida by direct injection capillary electrophoresis[J]. Phytochemical Analysis, 2008,19(2): 136—140.

[45] Oka H, Harada K, Ito Y, Ito Y. Separation of antibiotics by counter-current chromatography[J]. Journal of Chromatography A, 1998,812(1): 35—52.

[46] Sethi N, Anand A, Sharma A, Chandrul K K, Jain G, Srinivasa K S. High speed counter current chromatography: A support-free LC technique[J]. Journal of Pharmacy & Bioallied Sciences, 2009,1(1): 8—15.

[47] 罗娅君,边清泉,李绣菊. 高速逆流色谱分离制备马比木中的三个喜树碱类成分[C]. 北京: 中国化学会第29届学术年会摘要集-第02分会: 分离分析及微, 纳流控新方法, 2014.

[48] Pai S R, Pawar N V, Nimbalkar M S, Kshirsagar P R, Kolar F K, Dixit G B. Seasonal variation in content of camptothecin from the bark of Nothapodytes nimmoniana (Grah.) Mabb., using HPLC analysis[J]. Pharmaceutical Research, 2013,5(3): 219.

[49] Mingzhang A, Jing W, Yue S, Wentao G, Longjiang Y. Camptothecin distribution and content in Nothapodytes nimmoniana[J]. Natural Product Communications, 2011,6(2): 197—200.

[50] Srimany A, Ifa D R, Naik H R, Bhat V, Cooks R G, Pradeep T. Direct analysis of camptothecin from Nothapodytes nimmoniana by desorption electrospray ionization mass spectrometry (DESI-MS)[J]. Analyst. 2011,136(15): 3066—3068.

[51] Watase I, Sudo H, Yamazaki M, Saito K. Regeneration of transformed Ophiorrhiza pumila plants producing camptothecin[J]. Plant Biotechnology, 2004,21(5): 337—342.

[52] Lorence A, Nessler C L. Camptothecin, over four decades of surprising findings[J]. Phytochemistry, 2004,65(20): 2735—2749.

[53] Lu Y, Wang H, Wang W, Qian Z, Li L, Wang J, Zhou G, Kai G. Molecular characterization and expression analysis of a new cDNA encoding strictosidine synthase from Ophiorrhiza japonica[J]. Molecular Biology Reports, 2009,36(7): 1845—1852.

[54] Kai G. Effect of three plant hormone elicitors on the camptothecin accumulation and gene transcript profiling in Camptotheca acuminata seedlings[J]. International Journal of Sciences, 2014,3(1): 86—95.

[55] Comins D L, Nolan J M. A practical six-step synthesis of (S)-camptothecin[J]. Organic letters, 2001,3(26): 4255—4257.

[56] Yu J, DePue J, Kronenthal D. Synthesis of (±)-camptothecin using a [3+ 2] nitrone cycloaddition to construct the CDE ring moiety[J]. Tetrahedron Letters, 2004,45(39): 7247—7250.

[57] López-Meyer M, Nessler C L, McKnight T D. Sites of accumulation of the antitumor alkaloid camptothecin in Camptotheca acuminata[J]. Planta Medica, 1994,60(6): 558—560.

[58] Rehman S, Shawl A S, Verma V, Kour A, Athar M, Andrabi R, Sultan P, Qazi G N. An endophytic Neurospora sp. from Nothapodytes foetida producing camptothecin[J]. Applied Biochemistry and Microbiology, 2008,44(2): 203—209.

文章导航

/