期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 74, 期 2, 页码 504-512出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo802232u
关键词
-
资金
- NIH Intramural Research Program
- Intramural AIDS Targeted Antiviral Program
- Office of the Director, NIH
Six new depsipeptides belonging to two different structural classes, termed celebesides A-C and theopapuamides B-D, have been isolated from the marine sponge Siliquariaspongia mirabilis. Their structures were determined using extensive 2D NMR and ESI-MS/MS techniques. Celebesides are unusual cyclic depsipeptides that comprise a polyketide moiety and five amino acid residues, including an uncommon 3-carbamoyl threonine, and a phosphoserine residue in celebesides A and B. Theopapuamides B-D are undecapeptides with an N-terminal fatty acid moiety containing two previously unreported amino acids, 3-acetamido-2-aminopropanoic acid and 4-amino-2,3-dihydroxy-5-methylhexanoic acid. The relative configuration of the polyketide moiety in celebesides was resolved by J-based analysis and quantum mechanical calculations, the results of which were self-consistent. Celebeside A neutralized HIV-1 in a single-round infectivity assay with an IC50 value of 1.9 +/- 0.4 mu g/mL while the nonphosphorylated analog celebeside C was inactive at concentrations as high as 50 mu g/mL. Theopapuamides A-C showed cytotoxicity against human colon carcinoma (HCT-116) cells with IC50 values between 2.1 and 4.0 mu g/mL and exhibited strong antifungal activity against wildtype and amphotericin B-resistant strains of Candida albicans at loads of 1-5 mu g/disk.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据