Synthesis and Biological Evaluation of Purpurealidin E-Derived Marine Sponge Metabolites: Aplysamine-2, Aplyzanzine A, and Suberedamines A and B

被引：17

作者：

Kottakota, Suresh K. ^{[1
]}

Evangelopoulos, Dimitrios ^{[2
,3
]}

Alnimr, Amani ^{[3
]}

Bhakta, Sanjib ^{[2
]}

McHugh, Timothy D. ^{[3
]}

Gray, Mark ^{[1
]}

Groundwater, Paul W. ^{[4
]}

Marrs, Emma C. L. ^{[5
]}

Perry, John D. ^{[5
]}

Spilling, Christopher D. ^{[6
]}

Harburn, J. Jonathan ^{[1
]}

机构：

[1] Univ Sunderland, Dept Pharm Hlth & Well Being, Sunderland Pharm Sch, Sunderland SR1 3SD, England

[2] Univ London, Birkbeck Coll, Dept Biol Sci, Inst Struct & Mol Biol, London WC1E 7HX, England

[3] Univ London, Dept Infect, Ctr Clin Microbiol, London NW3 2PF, England

[4] Univ Sydney, Fac Pharm, Sydney, NSW 2006, Australia

[5] Freeman Rd Hosp, Dept Microbiol, Newcastle Upon Tyne NE7 7DN, Tyne & Wear, England

[6] Univ Missouri, Dept Chem & Biochem, St Louis, MO 63121 USA

来源：

JOURNAL OF NATURAL PRODUCTS | 2012年 / 75卷 / 06期

关键词：

ACTIVATED CHEMICAL DEFENSE; NATURAL-PRODUCTS; TYROSINE; INHIBITION; IDENTIFICATION; PSAMMAPLIN; CHEMISTRY;

D O I：

10.1021/np300102z

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

Five purpurealidin-derived marine secondary sponge metabolies have been synthesized through the carbodiimide coupling of an appropriate bromotyrosine unit. The structure elucidations have been confirmed through direct comparison with spectroscopic data of isolated natural products. Aplyzanzine A has been shown to be the most active product against a broad bacterial and fungal screen, demonstrating MIC values 2 to 4 times lower than the other metabolites in this study. Compounds 2, 3, 4a, and 5-7 exhibit a modest inhibition against slow growing mycobacteria (MIC 25-50 mu g/mL), including Mycobacterium tuberculosis. iso-Anomoian A and suberedamine B showed antitumor activity in the NCI-DTP60 cell line screen at single-digit micromolar concentrations, with iso-anomoian A inhibiting 53 cell lines. These molecules present novel scaffolds for further optimization.

引用

页码：1090 / 1101

页数：12

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