Leonurusoleanolides E-J, Minor Spirocyclic Triterpenoids from Leonurus japonicus Fruits

被引:38
|
作者
Ye, Miao [1 ,2 ,3 ,4 ]
Xiong, Juan [1 ]
Zhu, Jing-Jing [3 ,4 ]
Hong, Jun-Lin [5 ]
Zhao, Yun [3 ,4 ]
Fan, Hui [3 ,4 ]
Yang, Guo-Xun [1 ]
Xia, Gang [3 ,4 ]
Hu, Jin-Feng [1 ,3 ,4 ]
机构
[1] Fudan Univ, Sch Pharm, Dept Nat Prod Chem, Shanghai 201203, Peoples R China
[2] Fujian Univ Tradit Chinese Med, Sch Pharm, Fuzhou 350122, Peoples R China
[3] E China Normal Univ, Dept Chem, Shanghai 200062, Peoples R China
[4] E China Normal Univ, Inst Adv Interdisciplinary Res, Shanghai 200062, Peoples R China
[5] Sichuan Normal Univ, Coll Chem & Mat Sci, Chengdu 610068, Peoples R China
来源
JOURNAL OF NATURAL PRODUCTS | 2014年 / 77卷 / 01期
关键词
CYCLIC NONAPEPTIDES; NORTRITERPENOIDS; HETEROPHYLLUS; LEAVES; CELLS;
D O I
10.1021/np400838a
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Six new (leonurusoleanolides E-J, 1-6) and five known (7-11) nortriterpenoids were isolated and characterized from the dried fruits of Leonurus japonicus. They all contain a distinctive 19(18 -> 17)-abeo-28-noroleanane-type spirocylclic skeleton with a trans or a cis acyl substituent at C-3 or C-23. Similar to the previously known leonurusoleanolides A/B (7/8) and C/D (9/10), compounds 1/2 and 3/4 were also found to exist as equilibrium mixtures of trans and cis isomers. The isolated pure compounds and mixtures were evaluated for their cytotoxicity against a small panel of human cancer cell lines (BGC-823 and KE-97 gastric carcinoma, Huh-7 hepatocarcinoma, Jurkat T cell lymphoblasts, and MCF-7 breast adenocarcinoma) using the CellTiter-Glo luminescent cell viability assay method. Among them, (2 alpha,3 beta,17R*,18 beta)-3-O-(trans-caffeoyl)-19(18 -> 17)-abeo-28-norolean-12-ene-2,18,23-triol (leonurusoleanolide J, 6) showed the most potent cytotoxic activity, with IC50 values less than 10 mu M.
引用
收藏
页码:178 / 182
页数:5
相关论文
共 34 条
  • [21] Antimicrobial and Cytotoxic Activities of Synthetically Derived Tambjamines C and E-J, BE-18591, and a Related Alkaloid from the Marine Bacterium Pseudoalteromonas tunicata
    Pinkerton, David M.
    Banwell, Martin G.
    Garson, Mary J.
    Kumar, Naresh
    de Moraes, Manoel Odorico
    Cavalcanti, Bruno C.
    Barros, Francisco W. A.
    Pessoa, Claudia
    CHEMISTRY & BIODIVERSITY, 2010, 7 (05) : 1311 - 1324
  • [22] Pestalotiopols E-J, Six New Polyketide Derivatives from a Marine Derived Fungus Pestalotiopsis sp. SWMU-WZ04-1
    Jiang, Liyuan
    Teng, Baorui
    Zhang, Mengyu
    Chen, Siwei
    Zhang, Dan
    Zhai, Longfei
    Lin, Jiafu
    Lei, Hui
    MARINE DRUGS, 2024, 22 (01)
  • [23] A COMPARISON OF THE E-J CHARACTERISTICS OF 4 NBTI SUPERCONDUCTING COMPOSITES AT EQUIVALENT ELECTRIC-FIELD LEVELS FROM 10(-4) TO 10(-7)VM-1
    JENKINS, RG
    JONES, H
    KILLORAN, N
    TIMMS, W
    IEEE TRANSACTIONS ON MAGNETICS, 1991, 27 (02) : 1182 - 1185
  • [24] NONLINEAR U(J) DEPENDENCE DETERMINED DIRECTLY FROM LOW-ELECTRIC-FIELD E-J(S) CURVES IN YBA2CU3O7-DELTA THIN-FILMS
    WEN, HH
    ZHAO, ZX
    WIJNGAARDEN, RJ
    RECTOR, J
    DAM, B
    GRIESSEN, R
    PHYSICAL REVIEW B, 1995, 52 (06): : 4583 - 4587
  • [25] Effect of Triterpenoids and Limonoids Isolated from Cabralea canjerana and Carapa guianensis (Meliaceae) against Spodoptera frugiperda (J. E. Smith)
    Sarria, Andre L. F.
    Soares, Marcio S.
    Matos, Andreia P.
    Fernandes, Joao B.
    Vieira, Paulo C.
    da Silva, M. Fatima das G. F.
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION C-A JOURNAL OF BIOSCIENCES, 2011, 66 (5-6): : 245 - 250
  • [26] Ancistrobrevines E-J and related naphthylisoquinoline alkaloids from the West African liana Ancistrocladus abbreviatus with inhibitory activities against Plasmodium falciparum and PANC-1 human pancreatic cancer cells
    Fayez, Shaimaa
    Feineis, Doris
    Assi, Laurent Ake
    Kaiser, Marcel
    Brun, Reto
    Awale, Suresh
    Bringmann, Gerhard
    FITOTERAPIA, 2018, 131 : 245 - 259
  • [27] Major rearrangements in the E element and minor variations in the U3 sequences of the avian leukosis subgroup J provirus isolated from field myelocytomatosis
    D. Hue
    G. Dambrine
    C. Denesvre
    S. Laurent
    M. Wyers
    D. Rasschaert
    Archives of Virology, 2006, 151 : 2431 - 2446
  • [28] Major rearrangements in the E element and minor variations in the U3 sequences of the avian leukosis subgroup J provirus isolated from field myelocytomatosis
    Hue, D.
    Dambrine, G.
    Denesvre, C.
    Laurent, S.
    Wyers, M.
    Rasschaert, D.
    ARCHIVES OF VIROLOGY, 2006, 151 (12) : 2431 - 2446
  • [29] Insecticidal activity of two organic extracts from Libidibia coriaria (Jacq.) Schltdl. fruits against Spodoptera frugiperda J. E. Smith
    Sanchez-Alonso, Itzel
    Fonseca-Gonzalez, Alicia
    Olmedo-Juarez, Agustin
    Olivares-Perez, Jaime
    Gonzalez-Cortazar, Manases
    Monteon-Ojeda, Abraham
    Hernandez, Saul Rojas
    NATURAL PRODUCT RESEARCH, 2024,