Bioactive Bromotyrosine-Derived Alkaloids from the Polynesian Sponge Suberea ianthelliformis

被引:15
|
作者
El-Demerdash, Amr [1 ,2 ]
Moriou, Celine [1 ]
Toullec, Jordan [3 ]
Besson, Marc [4 ,5 ]
Soulet, Stephanie [6 ]
Schmitt, Nelly [6 ]
Petek, Sylvain [3 ]
Lecchini, David [4 ]
Debitus, Cecile [3 ]
Al-Mourabit, Ali [1 ]
机构
[1] Univ Paris Saclay, Univ Paris Sud, CNRS, UPR 2301,Inst Chim Subst Nat, 1 Ave Terrasse, F-91198 Gif Sur Yvette, France
[2] Mansoura Univ, Div Organ Chem, Dept Chem, Fac Sci, Mansoura 35516, Egypt
[3] UBO, IFREMER, IUEM, LEMAR,IRD,CNRS, F-29280 Plouzane, France
[4] PSL Res Univ, CNRS, CRIOBE, EPHE,UPVD, F-98729 Moorea, French Polynesi, France
[5] Univ Pierre & Marie Curie Paris, Observ Oceanol Banyuls Sur Mer, F-66650 Banyuls Sur Mer, France
[6] UPF, EIO, ILM, IFREMER,IRD, F-98702 Tahiti, French Polynesi, France
关键词
brominated tyrosine alkaloids; Suberea ianthelliformis; cytotoxicity; acetylcholinesterase inhibition; BROMINATED METABOLITES; ANTIBACTERIAL; ACETYLCHOLINESTERASE; APLYZANZINE; DERIVATIVES; INHIBITORS; TOXIN;
D O I
10.3390/md16050146
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Herein, we describe the isolation and spectroscopic identification of eight new tetrabrominated tyrosine alkaloids 2-9 from the Polynesian sponge Suberea ianthelliformis, along with known major compound psammaplysene D (1), N,N-dimethyldibromotyramine, 5-hydroxy xanthenuric acid, and xanthenuric acid. Cytotoxicity and acetylcholinesterase inhibition activities were evaluated for some of the isolated metabolites. They exhibited moderate antiproliferative activity against KB cancer cell lines, but psammaplysene D (1) displayed substantial cytotoxicity as well as acetylcholinesterase inhibition with IC50 values of 0.7 M and 1.3 M, respectively.
引用
收藏
页数:16
相关论文
共 50 条
  • [21] Brominated Arginine-Derived Alkaloids from the Red Sea Sponge Suberea mollis
    Shaala, Lamiaa A.
    Bamane, Faida H.
    Badr, Jihan M.
    Youssef, Diaa T. A.
    JOURNAL OF NATURAL PRODUCTS, 2011, 74 (06): : 1517 - 1520
  • [22] Bioactive Metabolites from the Sponge Suberea sp.
    Shaker, Kamel H.
    Zinecker, Heidi
    Ghani, Mohamed A.
    Imhoff, Johannes F.
    Schneider, Bernd
    CHEMISTRY & BIODIVERSITY, 2010, 7 (12) : 2880 - 2887
  • [23] PUREALIDIN-A, A NEW CYTOTOXIC BROMOTYROSINE-DERIVED ALKALOID FROM THE OKINAWAN MARINE SPONGE PSAMMAPLYSILLA-PUREA
    ISHIBASHI, M
    TSUDA, M
    OHIZUMI, Y
    SASAKI, T
    KOBAYASHI, J
    EXPERIENTIA, 1991, 47 (03): : 299 - 300
  • [24] Archerine, a novel anti-histaminic bromotyrosine-derived compound from the Caribbean marine sponge Aplysina archeri
    Ciminiello, P
    Dell'Aversano, C
    Fattorusso, E
    Magno, S
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 2001 (01) : 55 - 60
  • [25] Ianthesine E, a new bromotyrosine-derived metabolite from the Great Barrier Reef sponge Pseudoceratina sp.
    Kalaitzis, John A.
    Leone, Priscila De Almeida
    Hooper, John N. A.
    Quinn, Ronald J.
    NATURAL PRODUCT RESEARCH, 2008, 22 (14) : 1263 - 1269
  • [26] Ma'edamines A and B, cytotoxic bromotyrosine alkaloids with a unique 2(1H)pyrazinone ring from sponge Suberea sp.
    Hirano, K
    Kubota, T
    Tsuda, M
    Watanabe, K
    Fromont, J
    Kobayashi, J
    TETRAHEDRON, 2000, 56 (41) : 8107 - 8110
  • [27] THE STRUCTURES OF APLYSINAMISINE-I, APLYSINAMISINE-II, AND APLYSINAMISINE-III - NEW BROMOTYROSINE-DERIVED ALKALOIDS FROM THE CARIBBEAN SPONGE APLYSINA-CAULIFORMIS
    RODRIGUEZ, AD
    PINA, IC
    JOURNAL OF NATURAL PRODUCTS, 1993, 56 (06): : 907 - 914
  • [28] Antibacterial and anticholinesterase activities of aplysamine-4, a bromotyrosine-derived metabolite of a Red Sea marine sponge
    Sepcic, K
    Mancini, I
    Vidic, I
    Jovan, U
    Frassanito, R
    Pietra, F
    Macek, P
    Turk, T
    JOURNAL OF NATURAL TOXINS, 2001, 10 (03) : 181 - 191
  • [29] 20-N-methylpurpuramine E:: New bromotyrosine-derived metabolite from Okinawan marine sponge Pseudoceratina purpurea
    Teruya, Toshiaki
    Iwasaki, Arihiro
    Suenaga, Kiyotake
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2008, 81 (08) : 1026 - 1027
  • [30] 11-OXOAEROTHIONIN - A CYTOTOXIC ANTITUMOR BROMOTYROSINE-DERIVED ALKALOID FROM THE CARIBBEAN MARINE SPONGE APLYSINA-LACUNOSA
    ACOSTA, AL
    RODRIGUEZ, AD
    JOURNAL OF NATURAL PRODUCTS, 1992, 55 (07): : 1007 - 1012