Citation: Rong-Rong Zhang, Hai-Yan Tian, Yi Wu, Xiao-Hui Sun, Jian-Long Zhang, Zhi-Guo Ma, Ren-Wang Jiang. Isolation and chemotaxonomic signifi cance of stenine-and stemoninine-type alkaloids from the roots of Stemona tuberosa[J]. Chinese Chemical Letters, ;2014, 25(9): 1252-1255. doi: 10.1016/j.cclet.2014.03.051 shu

Isolation and chemotaxonomic signifi cance of stenine-and stemoninine-type alkaloids from the roots of Stemona tuberosa

  • Corresponding author: Zhi-Guo Ma,  Ren-Wang Jiang, 
  • Received Date: 23 January 2014
    Available Online: 21 March 2014

    Fund Project: Thisworkwas supported by the Fundamental Research Funds for the Central Universities (No. 11612603) (No. 11612603)

  • One new stenine-type alkaloid, tuberostemonine D (1), together with five known stenine-type alkaloids (2-6) and two known stemoninine-type alkaloids (7 and 8), were isolated from the roots of Stemona tuberosa. Their structureswere elucidated by extensive spectroscopic methods (IR,UV,MS, 1D and 2D NMR), and the structure of 1 was further confirmed by X-ray diffraction analysis. First simultaneous isolation of stenine-and stemoninine-type alkaloids not only added a newchemical type and increased the chemical diversity of Stemona tuberosa, but also provided chemotaxonomic clues for the close relationship between genera Stemona and Stichoneuron, and favored retaining them in the same family.
  • 加载中
    1. [1]

      [1] Pharmacopoeia Commission of People's Republic of China, The Pharmacopoeia of the People's Republic of China, Chemical Industry Publishing House, Beijing, 2005, p. 100.

    2. [2]

      [2] Jiangsu New Medical College, Dictionary of Chinese Traditional Medicine, Shanghai People's Publishing House, Shanghai, 1977, pp. 858-861.

    3. [3]

      [3] Y.T. Xu, P.C. Shaw, R.W. Jiang, et al., Antitussive and central respiratory depressant effects of Stemona tuberosa, J. Ethnopharmacol. 128 (2010) 679-684.

    4. [4]

      [4] X. Zhou, P.H.H. Leung, N. Li, et al., Oral absorption and antitussive activity of tuberostemonine alkaloids from the roots of Stemona tuberosa, Planta Med. 75 (2009) 575-580.

    5. [5]

      [5] X.Z. Yang, J.Y. Zhu, C.P. Tang, et al., Alkaloids from roots of Stemona sessilifolia and their antitussive activities, Planta Med. 75 (2009) 174-177.

    6. [6]

      [6] R.A. Pilli, G.B. Rossoa, M.D.C.F.D. Oliveira, The chemistry of Stemona alkaloids: an update, Nat. Prod. Rep. 27 (2010) 1908-1937.

    7. [7]

      [7] R.W. Jiang, P.M. Hon, Y.T. Xu, et al., Isolation and chemotaxonomic significance of tuberostemospironine-type alkaloids from Stemona tuberosa, Phytochemistry 67 (2006) 52-57.

    8. [8]

      [8] R.W. Jiang, P.M. Hon, P.P.H. But, et al., Isolation and stereochemistry of two new alkaloids from Stemona tuberosa, Tetrahedron 58 (2002) 6705-6712.

    9. [9]

      [9] R.W. Jiang, P.M. Hon, Y. Zhou, et al., Alkaloids and chemical diversity of Stemona tuberosa, J. Nat. Prod. 69 (2006) 749-754.

    10. [10]

      [10] H.S. Chung, P.M. Hon, G. Lin, et al., Antitussive activity of Stemona alkaloids from Stemona tuberosa, Planta Med. 69 (2003) 914-920.

    11. [11]

      [11] S.W. Liu, H.Z. Fu, W.H. Lin, Alkaloids from roots of Stemona tuberosa, Acta Pharm. Sin. 34 (1999) 372-375.

    12. [12]

      [12] L.G. Lin, H.P.H. Leung, J.Y. Zhu, et al., Croomine-and tuberostemonine-type alkaloids from roots of Stemona tuberosa and their antitussive activity, Tetrahedron 64 (2008) 10155-10161.

    13. [13]

      [13] L.G. Lin, Q.X. Zhong, T.Y. Cheng, et al., Stemoninines from the roots of Stemona tuberosa, J. Nat. Prod. 69 (2006) 1051-1054.

    14. [14]

      [14] C. Kuo, T.T. Chu, A study of Stemona alkaloids: I, Acta Chim. Sin. 36 (1978), 291-196.

    15. [15]

      [15] H. Greger, Structural relationships, distribution and biological activities of Stemona alkaloids, Planta Med. 72 (2006) 99-113.

    16. [16]

      [16] J.P. Hua, D.H. Yang, W.H. Lin, et al., Alkaloids from the roots of Stemona tuberosa, Helv. Chim. Acta 92 (2009) 2125-2133.

    17. [17]

      [17] K. Sumet, S. Johann, F. Susanne, et al., Structural relationships of Stemona alkaloids: assessment of species-specific accumulation trends for exploiting their biological activities, J. Nat. Prod. 74 (2011) 1931-1938.

    18. [18]

      [18] R.A. Ramli, W. Lie, S.G. Pyne, Alkaloids from the roots and leaves of Stichoneuron halabalensis and their acetylcholinesterase inhibitory activities, Nat. Prod. Commun. 8 (2013) 695-698.

  • 加载中
    1. [1]

      Jingping HuJing Xu . Total synthesis of a putative yuzurimine-type Daphniphyllum alkaloid C14epi-deoxycalyciphylline H. Chinese Chemical Letters, 2024, 35(4): 108733-. doi: 10.1016/j.cclet.2023.108733

    2. [2]

      Fenglin JiangAnan LiuQian WeiYoucai Hu . Editing function of type Ⅱ thioesterases in the biosynthesis of fungal polyketides. Chinese Chemical Letters, 2024, 35(10): 109504-. doi: 10.1016/j.cclet.2024.109504

    3. [3]

      Wei SuXiaoyan LuoPeiyuan LiYing ZhangChenxiang LinKang WangJianzhuang Jiang . Phthalocyanine self-assembled nanoparticles for type Ⅰ photodynamic antibacterial therapy. Chinese Chemical Letters, 2024, 35(12): 109522-. doi: 10.1016/j.cclet.2024.109522

    4. [4]

      Ajay Piriya Vijaya Kumar Saroja Yuhan Wu Yang Xu . Improving the electrocatalysts for conversion-type anodes of alkali-ion batteries. Chinese Journal of Structural Chemistry, 2025, 44(1): 100408-100408. doi: 10.1016/j.cjsc.2024.100408

    5. [5]

      Lu-Lu HeLan-Tu XiongXin WangYu-Zhen LiJia-Bao LiYu ShiXin DengZi-Ning Cui . Application of inhibitors targeting the type III secretion system in phytopathogenic bacteria. Chinese Chemical Letters, 2025, 36(4): 110044-. doi: 10.1016/j.cclet.2024.110044

    6. [6]

      Shengyu ZhaoQinhao ShiWuliang FengYang LiuXinxin YangXingli ZouXionggang LuYufeng Zhao . Suppression of multistep phase transitions of O3-type cathode for sodium-ion batteries. Chinese Chemical Letters, 2024, 35(5): 108606-. doi: 10.1016/j.cclet.2023.108606

    7. [7]

      Run-Han LiTian-Yi DangWei GuanJiang LiuYa-Qian LanZhong-Min Su . Evolution exploration and structure prediction of Keggin-type group IVB metal-oxo clusters. Chinese Chemical Letters, 2024, 35(5): 108805-. doi: 10.1016/j.cclet.2023.108805

    8. [8]

      Dake LiuShuyan LiuFanlei HuZhongtang LiZhongjun LiN-Glycosylated type Ⅱ collagen peptides as therapeutic saccharide vaccines for rheumatoid arthritis. Chinese Chemical Letters, 2024, 35(5): 108762-. doi: 10.1016/j.cclet.2023.108762

    9. [9]

      Na WangWang LuoHuaiyi ShenHuakai LiZejiang XuZhiyuan YueChao ShiHengyun YeLeping Miao . Crystal engineering regulation achieving inverse temperature symmetry breaking ferroelasticity in a cationic displacement type hybrid perovskite system. Chinese Chemical Letters, 2024, 35(5): 108696-. doi: 10.1016/j.cclet.2023.108696

    10. [10]

      Jiaxiang GuoZeyi LiTianyu ZhangXinyu TianYue WangChuandong Dou . Thienothiophene-centered ladder-type π-systems that feature distinct quinoidal π-extension. Chinese Chemical Letters, 2024, 35(5): 109337-. doi: 10.1016/j.cclet.2023.109337

    11. [11]

      Zhengzheng LIUPengyun ZHANGChengri WANGShengli HUANGGuoyu YANG . Synthesis, structure, and electrochemical properties of a sandwich-type {Co6}-cluster-added germanotungstate. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1173-1179. doi: 10.11862/CJIC.20240039

    12. [12]

      Shuang LiJiayu SunGuocheng LiuShuo ZhangZhong ZhangXiuli Wang . A new Keggin-type polyoxometallate-based bifunctional catalyst for trace detection and pH-universal photodegradation of phenol. Chinese Chemical Letters, 2024, 35(8): 109148-. doi: 10.1016/j.cclet.2023.109148

    13. [13]

      Yatian DengDao WangJinglan ChengYunkun ZhaoZongbao LiChunyan ZangJian LiLichao Jia . A new popular transition metal-based catalyst: SmMn2O5 mullite-type oxide. Chinese Chemical Letters, 2024, 35(8): 109141-. doi: 10.1016/j.cclet.2023.109141

    14. [14]

      Huaran ZhangYuting HuangYingjie TangDekun KongYi Zou . Genome mining of multi-substituted alkylresorcinols from a hybrid highly reducing- and type Ⅲ- polyketide pathway. Chinese Chemical Letters, 2024, 35(7): 108968-. doi: 10.1016/j.cclet.2023.108968

    15. [15]

      Shiyu HouMaolin SunLiming CaoChaoming LiangJiaxin YangXinggui ZhouJinxing YeRuihua Cheng . Computational fluid dynamics simulation and experimental study on mixing performance of a three-dimensional circular cyclone-type microreactor. Chinese Chemical Letters, 2024, 35(4): 108761-. doi: 10.1016/j.cclet.2023.108761

    16. [16]

      Shengyu ZhaoXuan YuYufeng Zhao . A water-stable high-voltage P3-type cathode for sodium-ion batteries. Chinese Chemical Letters, 2024, 35(9): 109933-. doi: 10.1016/j.cclet.2024.109933

    17. [17]

      Zhi-Yuan YueHua-Kai LiNa WangShan-Shan LiuLe-Ping MiaoHeng-Yun YeChao Shi . Dehydration-triggered structural phase transition-associated ferroelectricity in a hybrid perovskite-type crystal. Chinese Chemical Letters, 2024, 35(10): 109355-. doi: 10.1016/j.cclet.2023.109355

    18. [18]

      Rong-Nan YiWei-Min He . Visible light/copper catalysis enabled radial type ring-opening of sulfonium salts. Chinese Chemical Letters, 2025, 36(4): 110787-. doi: 10.1016/j.cclet.2024.110787

    19. [19]

      Xiaofei NIUKe WANGFengyan SONGShuyan YU . Self-assembly of [Pd6(L)4]8+-type macrocyclic complexes for fluorescent sensing of HSO3-. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1233-1242. doi: 10.11862/CJIC.20240057

    20. [20]

      Dongmei DaiXiaobing LaiXiaojuan WangYunting YaoMengmin JiaLiang WangPengyao YanYaru QiaoZhuangzhuang ZhangBao LiDai-Huo Liu . Increasing (010) active plane of P2-type layered cathodes with hexagonal prism towards improved sodium-storage. Chinese Chemical Letters, 2024, 35(10): 109405-. doi: 10.1016/j.cclet.2023.109405

Metrics
  • PDF Downloads(0)
  • Abstract views(678)
  • HTML views(19)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return