Metachromins X and Y from a marine sponge Spongia sp. and their effects on cell cycle progression

被引:8
|
作者
Hitora, Yuki [1 ,5 ]
Takada, Kentaro [1 ]
Ise, Yuji [2 ,6 ]
Woo, Sau Pinn [3 ]
Inoue, Seiya [4 ]
Mori, Naoki [4 ,7 ]
Takikawa, Hirosato [4 ]
Nakamukai, Shohei [1 ]
Okada, Shigeru [1 ]
Matsunaga, Shigeki [1 ]
机构
[1] Univ Tokyo, Grad Sch Agr & Life Sci, Lab Aquat Nat Prod Chem, Bunkyo Ku, Tokyo 1138657, Japan
[2] Nagoya Univ, Grad Sch Sci, Sugashima Marine Biol Lab, Sugashima Cho, Toba, Mie 5170004, Japan
[3] Univ Sains Malaysia, Ctr Marine & Coastal Studies, Usm 11800, Penang, Malaysia
[4] Univ Tokyo, Grad Sch Agr & Life Sci, Dept Appl Biol Chem, Bukyo Ku, Tokyo 1138657, Japan
[5] Kumamoto Univ, Grad Sch Pharmaceut Sci, Kumamoto 8620973, Japan
[6] Univ Sains Malaysia, Ctr Marine & Coastal Studies, Gelugo, Penang, Malaysia
[7] Res Fdn ITSUU Lab, Takatsu Ku, 3-2-1 Sakado, Kawasaki, Kanagawa 2130012, Japan
关键词
Terpenoid; Marine sponge; Cell-cycle; Structure elucidation; ABSOLUTE-CONFIGURATION; CHIROPTICAL PROPERTIES; CIRCULAR-DICHROISM; SESQUITERPENOIDS; PORIFERA; DICTYOCERATIDA; DEMOSPONGIAE; REPLICATION; QUINONES; CDT1;
D O I
10.1016/j.bmc.2019.115233
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
New sesquiterpene quinones, metachromins X (1) and Y (2), together with the known metachromins C (3), J (4), and T (5), were isolated as inhibitors of cell cycle progression in the HeLa/Fucci2 cells. The structure of 1 was assigned by spectroscopic data and confirmed by a total synthesis. The planar structure of 2 was determined by interpretation of spectroscopic data, whereas its absolute configuration was analyzed by a combination of chiral HPLC and CD spectroscopy. Metachromins X (1) and C (3) arrested the cell cycle progression of HeLa/Fucci2 cells at S/G2/M phase.
引用
收藏
页数:6
相关论文
共 50 条
  • [21] SESQUITERPENE QUINONES FROM A VIET NAM SEA SPONGE Spongia SP.
    Utkina, N. K.
    Denisenko, V. A.
    CHEMISTRY OF NATURAL COMPOUNDS, 2011, 47 (01) : 135 - 137
  • [22] Sesquiterpene quinones from a Viet Nam sea sponge Spongia Sp.
    N. K. Utkina
    V. A. Denisenko
    Chemistry of Natural Compounds, 2011, 47
  • [23] Cell differentiation inducers from a marine sponge Biemna sp.
    Ueoka, Reiko
    Ise, Yuji
    Okada, Shigeru
    Matsunaga, Shigeki
    TETRAHEDRON, 2011, 67 (35) : 6679 - 6681
  • [24] Spongiains A-C: Three new spongian diterpenes with ring A rearrangement from the marine sponge Spongia sp.
    Liang, Yong-Qian
    Liao, Xiao-Jian
    Lin, Jia-Li
    Xu, Wei
    Chen, Guo-Dong
    Zhao, Bing-Xin
    Xu, Shi-Hai
    TETRAHEDRON, 2019, 75 (27) : 3802 - 3808
  • [25] Structural elucidation and antimicrobial activity of a diketopiperazine isolated from a Bacillus sp. associated with the marine sponge Spongia officinalis
    Bhattacharya, Dhruba
    Lai, Tapan Kumar
    Saha, Amit
    Selvin, Joseph
    Mukherjee, Joydeep
    NATURAL PRODUCT RESEARCH, 2021, 35 (14) : 2315 - 2323
  • [26] Isolation of Scalimides A-L: β-Alanine-Bearing Scalarane Analogs from the Marine Sponge Spongia sp.
    Shin, A-Young
    Lee, Hyi-Seung
    Lee, Jihoon
    MARINE DRUGS, 2022, 20 (11)
  • [27] New merosesquiterpenes from a Vietnamese marine sponge of Spongia sp and their biological activities
    Hien Minh Nguyen
    Ito, Takuya
    Kurimoto, Shin-ichiro
    Ogawa, Mika
    Win, Nwet Nwet
    Vo Quoc Hung
    Hoai Thi Nguyen
    Kubota, Takaaki
    Kobayashi, Jun'ichi
    Morita, Hiroyuki
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2017, 27 (14) : 3043 - 3047
  • [28] NUCLEOSIDES FROM THE MARINE SPONGE Callyspongia SP.
    Huang, Riming
    Zhou, Xuefeng
    Peng, Yan
    Yang, Xianwen
    Xu, Tunhai
    Liu, Yonghong
    CHEMISTRY OF NATURAL COMPOUNDS, 2011, 46 (06) : 1010 - 1011
  • [29] Norisoprenoids from the marine sponge Spheciospongia sp.
    Liu, Dong
    Xu, Min-Juang
    Wu, Li-Jun
    Deng, Zhi-Wei
    Lin, Wen-Han
    JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, 2009, 11 (09) : 811 - 816
  • [30] Diketopiperazines from marine sponge Haliclona sp.
    Wang, Bin
    Huang, Riming
    Liu, Yonghong
    PROCEEDINGS OF 2009 INTERNATIONAL CONFERENCE OF NATURAL PRODUCT AND TRADITIONAL MEDICINE, VOLS 1 AND 2, 2009, : 245 - 249