Isolation, structure determination and cytotoxicity studies of tryptophan alkaloids from an Australian marine sponge Hyrtios sp.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

卷:24

Article

Khokhar, Shahan¹  Feng, Yunjiang¹  Campitelli, Marc R.¹  Ekins, Merrick G.²  Hooper, John N. A.^1,2  Beattie, Karren D.¹  Sadowski, Martin C.³  Nelson, Colleen C.³  Davis, Rohan A.¹ 

[1] Griffith Univ, Eskitis Inst Drug Discovery, Brisbane, Qld 4111, Australia

[2] Queensland Museum, South Brisbane, Qld 4101, Australia

[3] Queensland Univ Technol, Australian Prostate Canc Res Ctr, Queensland Inst Hlth & Biomed Innovat, Princess Alexandra Hosp,Translat Res Inst, Brisbane, Qld 4102, Australia

关键词: Tryptophan alkaloid;    Marine sponge;    Hyrtios;    DFF-NMR;    Cytotoxicity;   

DOI  :  10.1016/j.bmcl.2014.05.104

来源: Elsevier

【 摘 要 】

Mass-guided fractionation of the MeOH extract from a specimen of the Australian marine sponge Hyrtios sp. resulted in the isolation of two new tryptophan alkaloids, 6-oxofascaplysin (2), and secofascaplysic acid (3), in addition to the known metabolites fascaplysin (1) and reticulatate (4). The structures of all molecules were determined following NMR and MS data analysis. Structural ambiguities in 2 were addressed through comparison of experimental and DFT-generated theoretical NMR spectral values. Compounds 1-4 were evaluated for their cytotoxicity against a prostate cancer cell line (LNCaP) and were shown to display IC50 values ranging from 0.54 to 44.9 mu M. (C) 2014 Elsevier Ltd. All rights reserved.

【 授权许可】

Free