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
  • [1] Metachromins R-T, new sesquiterpenoids from marine sponge Spongia sp.
    Takahashi, Yohei
    Yamada, Mika
    Kubota, Takaaki
    Froniont, Jane
    Kobayashi, Jun'ichi
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2007, 55 (12) : 1731 - 1733
  • [2] Neurotrophic sesterterpenes isolated from a marine sponge, Spongia sp.
    Tokue, Takanori
    Miura, Shunsuke
    Kato, Hikaru
    Hirota, Hiroshi
    Ohta, Tomihisa
    Tsukamoto, Sachiko
    HETEROCYCLES, 2006, 69 (01) : 521 - +
  • [3] Farnesoid X-activated receptor antagonists from a marine sponge Spongia sp.
    Nam, Sang-Jip
    Ko, Hyunsil
    Shin, Mihee
    Ham, Jungyeob
    Chin, Jungwook
    Kim, Youngshin
    Kim, Heeyoung
    Shin, Kyoungjin
    Choi, Hyukjae
    Kang, Heonjoong
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (20) : 5398 - 5402
  • [4] Metachromins J and K, new sesquiterpenoids from marine sponge Spongia species
    Takahashi, Y
    Tsuda, M
    Fromont, J
    Kobayashi, J
    HETEROCYCLES, 2006, 67 (02) : 791 - +
  • [5] Spongiacysteine, a novel cysteine derivative from marine sponge Spongia sp.
    Kobayashi, K
    Shimogawa, H
    Sakakura, A
    Teruya, T
    Suenaga, K
    Kigoshi, H
    CHEMISTRY LETTERS, 2004, 33 (10) : 1262 - 1263
  • [6] Three new cytotoxic sesterterpenes from a marine sponge Spongia sp.
    Tsukamoto, S
    Miura, S
    van Soest, RWM
    Ohta, T
    JOURNAL OF NATURAL PRODUCTS, 2003, 66 (03): : 438 - 440
  • [7] Metachromins L-Q, new sesquiterpenoid quinones with an amino acid residue from sponge Spongia sp.
    Takahashi, Yohei
    Kubota, Takaaki
    Fromont, Jane
    Kobayashi, Jun'ichi
    TETRAHEDRON, 2007, 63 (36) : 8770 - 8773
  • [8] New antibacterial sesquiterpene aminoquinones from a Vietnamese marine sponge of Spongia sp.
    Hien Minh Nguyen
    Ito, Takuya
    Nwet Nwet Win
    Kodama, Takeshi
    Vo Quoc Hung
    Hoai Thi Nguyen
    Morita, Hiroyuki
    PHYTOCHEMISTRY LETTERS, 2016, 17 : 288 - 292
  • [9] Three New Spongian Diterpenes from the Fijian Marine Sponge Spongia sp.
    Gross, Harald
    Wright, Anthony D.
    Reinscheid, Uwe
    Koenig, Gabriele M.
    NATURAL PRODUCT COMMUNICATIONS, 2009, 4 (03) : 315 - 322
  • [10] Cyclosmenospongine, a new sesquiterpenoid aminoquinone from an Australian marine sponge Spongia sp.
    Utkina, NK
    Denisenko, VA
    Scholokova, OV
    Virovaya, MV
    Prokof'eva, NG
    TETRAHEDRON LETTERS, 2003, 44 (01) : 101 - 102