Planta Med 2009; 75 - PE5
DOI: 10.1055/s-0029-1234566

New jaspamide derivatives from the marine sponge Jaspis sp.

S Ebada 1, W Lin 2, Z Deng 3, N de Voogd 4, P Proksch 1
  • 1Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine University, Universitaetsstrasse 1, D-40225 Duesseldorf, Germany
  • 2State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100083, People's Republic of China
  • 3Analytical and Testing Center, Beijing Normal University, Beijing 100875, People's Republic of China
  • 4National Museum of Natural History, PO Box 9517 2300 RA Leiden, Netherlands

Jaspamide (jasplakinolide, 1), a cyclodepsipeptide isolated from marine sponges of the genus Jaspis, is known for its pronounced biological activities which include antifungal, insecticidal, and cytotoxic activity against 36 human solid tumor cell cultures. The biological properties and structural features of jaspamide stimulated numerous efforts aiming at a total synthesis and structural modification. As a part of our ongoing studies on bioactive natural products from marine sponges we investigated a specimen of Jaspis sp. collected at Kalimantan (Indonesia). The crude methanolic extract exhibited considerable in vitro cytotoxic activity against mouse lymphoma L5178Y cells. Chromatographic separation the extract yielded jaspamide (1) as the major constituent. Through a detailed bioactivity-guided chemical investigation of the ethyl acetate souble fraction minor analogues of jaspamide, including the new natural products jaspamide Q (2) and jaspamide R (3) were obtained. The structures of the new compounds were unambiguously elucidated based on 1D and 2D NMR spectral data, mass spectrometry and comparison with the parent compound jaspamide. Details on the structure elucidation of the new jaspamide analogues will be presented.

Jaspamide (1)

Jaspamide Q (2) R1, R2=H, Jaspamide R (3) R1, R2=Br