Structures of new cytotoxic bicyclic hexapeptides with a phenylpropanoid unit from Rubia cordifolia

被引:0
作者
Fukaya, Haruhiko [1 ]
Kitamura, Rie [1 ]
Hasuda, Tomoyo [1 ]
Takeya, Koichi [1 ]
Aoyagi, Yutaka [2 ]
Nakane, Takahisa [3 ]
Hitotsuyanagi, Yukio [1 ]
机构
[1] Tokyo Univ Pharm & Life Sci, Sch Pharm, 1432-1 Horinouchi, Hachioji, Tokyo 1920392, Japan
[2] Kinjo Gakuin Univ, Coll Pharm, 2-1723 Omori,Moriyama Ku, Nagoya, Aichi 4638521, Japan
[3] Showa Pharmaceut Univ, 3-3165 Higashi Tamagawagakuen, Machida, Tokyo 1948543, Japan
关键词
Deoxybouvardin; Phenylpropanoid; Rubia cordifolia; Cytotoxicity; ANTITUMOR CYCLIC HEXAPEPTIDES; PROTEIN-SYNTHESIS; BOUVARDIN; CYCLOPEPTIDES;
D O I
10.1016/j.phytol.2024.12.004
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Four bicyclic hexapeptides RA-XXIX-RA-XXXII, which have a phenylpropanoid unit attached to the hydroxy group of the Tyr-6 residue of deoxybouvardin, were isolated from the roots of Rubia cordifolia L. Their structures were established on the basis of spectroscopic data, the X-ray crystallography of 4-O-methyl-RA-XXIX tribromide, and the chemical conversion of RA-XXIX and RA-XXX into RA-XXXII and RA-XXXI, respectively. RA-XXIX-RAXXXII exhibited 420-960 times and 53-330 times lower cytotoxicity than RA-VII toward the HL-60 and HCT-116 cell lines, respectively.
引用
收藏
页码:82 / 88
页数:7
相关论文
共 21 条
  • [1] SOLUTION FORMS OF BOUVARDIN AND RELATIVES FROM NMR-STUDIES - 6-O-METHYLBOUVARDIN
    BATES, RB
    COLE, JR
    HOFFMANN, JJ
    KRIEK, GR
    LINZ, GS
    TORRANCE, SJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (05) : 1343 - 1347
  • [2] Rubiyunnanins A and B, two novel cyclic hexapeptides from Rubia yunnanensis
    Fan, Jun-Ting
    Chen, Yi-Shan
    Xu, Wen-Yan
    Du, Liangcheng
    Zeng, Guang-Zhi
    Zhang, Yu-Mei
    Su, Jia
    Li, Yan
    Tan, Ning-Hua
    [J]. TETRAHEDRON LETTERS, 2010, 51 (52) : 6810 - 6813
  • [3] Rubiaceae-Type Cyclopeptides from Galianthe thalictroides
    Figueiredo, Patricia O.
    Matos, Maria de Fatima C.
    Perdomo, Renata T.
    Kato, Wilson H., Jr.
    Barros, Marcos Vinicius G. O.
    Garcez, Fernanda R.
    Garcez, Walmir S.
    [J]. JOURNAL OF NATURAL PRODUCTS, 2016, 79 (04): : 1165 - 1169
  • [4] ON ENANTIOMORPH-POLARITY ESTIMATION
    FLACK, HD
    [J]. ACTA CRYSTALLOGRAPHICA SECTION A, 1983, 39 (NOV): : 876 - 881
  • [5] Structures of bicyclic hexapeptides RA-XXVII and RA-XXVIII from Rubia cordifolia L.
    Fukaya, Haruhiko
    Anzai, Tatsuro
    Hasuda, Tomoyo
    Takeya, Koichi
    Aoyagi, Yutaka
    Nakane, Takahisa
    Hitotsuyanagi, Yukio
    [J]. TETRAHEDRON LETTERS, 2024, 147
  • [6] RA-XXV and RA-XXVI, Bicyclic Hexapeptides from Rubia cordifolia L.: Structure, Synthesis, and Conformation
    Hitotsuyanagi, Yukio
    Hirai, Masahito
    Odagiri, Masumi
    Komine, Miho
    Hasuda, Tomoyo
    Fukaya, Haruhiko
    Takeya, Koichi
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2019, 14 (01) : 205 - 215
  • [7] Isolation, Structure Determination, and Synthesis of Allo-RA-V and Neo-RA-V, RA-Series Bicyclic Peptides from Rubia cordifolia L.
    Hitotsuyanagi, Yukio
    Odagiri, Masumi
    Kato, Saori
    Kusano, Jun-ichi
    Hasuda, Tomoyo
    Fukaya, Haruhiko
    Takeya, Koichi
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (10) : 2839 - 2846
  • [8] Determination of absolute structure using Bayesian statistics on Bijvoet differences
    Hooft, Rob W. W.
    Straver, Leo H.
    Spek, Anthony L.
    [J]. JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2008, 41 : 96 - 103
  • [9] Rubipodanin B, a New Cytotoxic Cyclopeptide from Rubia podantha
    Hu, Yan-Yun
    Feng, Li
    Wang, Jia
    Zhang, Xue-Jia
    Wang, Zhe
    Tan, Ning-Hua
    [J]. CHEMISTRY & BIODIVERSITY, 2019, 16 (01)
  • [10] Rubischumanins A-C, new cytotoxic cyclopeptides from Rubia schumanniana
    Huang, Mao-Bo
    Zhao, Si-Meng
    Zeng, Guang-Zhi
    Kuang, Bin
    Chen, Xiao-Qiang
    Tan, Ning-Hua
    [J]. TETRAHEDRON, 2014, 70 (42) : 7627 - 7631