海洋海绵 Fasciospongia sp. 中的生物活性硫酸化甾体生物碱和甾体硫酸盐

Bioactive sulfated sesterterpene alkaloids and sesterterpene sulfates from the marine sponge Fasciospongia sp.

机构信息

Department of Chemistry and Biochemistry, College of Science and Engineering, University of Minnesota Duluth, 1039 University Drive, Duluth, Minnesota 55812, USA.

出版信息

J Nat Prod. 2009 Feb 27;72(2):319-23. doi: 10.1021/np8005343.

DOI:10.1021/np8005343

PMID:19178162

Abstract

Two new sulfated sesterterpene alkaloids, 19-oxofasciospongine A (3) and fasciospongine C (4), and a new sesterterpene sulfate, 25-hydroxyhalisulfate 9 (5), along with two known sesterterpene sulfates, halisulfates 7 (6) and 9 (7), were isolated from an organic extract of the marine sponge Fasciospongia sp. The structures of the new compounds were established on the basis of one- and two-dimensional NMR spectroscopic studies as well as by HRESIMS analysis. Compounds 1-7 exhibited inhibitory activity against Streptomyces 85E in the hyphae-formation inhibition assay. Compounds 1, 2, and 4-7 were not cytotoxic when tested at 20 microg/mL with MCF-7, LNCaP, and LU cell lines. Only compound 3 demonstrated a moderate cytotoxic effect on the MCF-7 (IC(50) 13.4 microM), LNCaP (IC(50) 21.8 microM), and LU-1 cells (IC(50) 5.0 microM), respectively.

摘要

从海洋海绵 Fasciospongia sp. 的有机提取物中分离得到两个新的磺化甾体生物碱，19-氧代 fasciospongine A (3) 和 fasciospongine C (4)，以及一个新的甾体硫酸盐 25-羟基 halisulfate 9 (5)，以及两个已知的甾体硫酸盐 halisulfates 7 (6) 和 9 (7)。新化合物的结构是基于一维和二维 NMR 光谱研究以及 HRESIMS 分析确定的。化合物 1-7 在菌丝形成抑制试验中对链霉菌 85E 表现出抑制活性。当用 MCF-7、LNCaP 和 LU 细胞系在 20 μg/mL 下测试时，化合物 1、2 和 4-7 均无细胞毒性。只有化合物 3 对 MCF-7 (IC50 13.4 μM)、LNCaP (IC50 21.8 μM) 和 LU-1 细胞 (IC50 5.0 μM) 分别表现出中等的细胞毒性作用。