Abstract

Aurilides are a class of depsipeptides occurring mainly in marine cyanobacteria. Members of the aurilide family have shown to exhibit strong cytotoxicity against various cancer cell lines. These compounds bear a pentapeptide, a polyketide, and an α-hydroxy ester subunit in their structure. A large number of remarkable studies on aurilides have emerged since 1996. This comprehensive account summarizes the biological activities and total syntheses of natural compounds of the aurilide family as well as their synthetic analogues.

Highlights

  • IntroductionFrom a specimen of this marine organism collected in the Japanese sea, Suenaga et al [2] isolated in 1996 aurilide (1), a 26-membered cyclodepsipeptide, which exhibits a strong cytotoxicity against HeLa S3 cells with an IC50 of 0.011 μg/mL

  • Differences in the α-Hydroxy and the Structurally, Acid the aurilide family membersSubunits can be described as cyclic depsipeptides, Structurally, the aurilide family members can be described as cyclic depsipeptides, whose frameworkacids can divided subunits: α-hydroxy acid residue, a whose framework can bebe divided into three subunits: an α-hydroxy acid residue, astructure polykeThree different α-hydroxy

  • The results show that deoxyaurilide 40 is slightly less cytotoxic than aurilide (1); the the hydroxyl group of the natural product is not essential for its high cytotoxicity logues 46−50 displayed considerable activity and could be useful as a molecule to search for the target responsible for the activity

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Summary

Introduction

From a specimen of this marine organism collected in the Japanese sea, Suenaga et al [2] isolated in 1996 aurilide (1), a 26-membered cyclodepsipeptide, which exhibits a strong cytotoxicity against HeLa S3 cells with an IC50 of 0.011 μg/mL. Were isolated from different sources of marine cyanobacteria. After focusing on the structural features and comparison of the biological activities of the aurilide class members, this report reviews the synthetic studies of the natural products and their analogues. In Loggerhead Key in the Dry collection of marine cyanobacteria

Differences in the α-Hydroxy and the Polyketide
Differences
Differences in the Pentapeptide Fragment
Biological Activities
H4 ester
Y OTES
Y OR transformation of 17a and 17b intoXenones
Synthesis of triols
H 4the
Cl22Cl
First synthesis of aurilide
34. Reagents and conditions:
ClAgNO
39. Reagents and conditions
Synthesis of deoxyaurilide
11. Synthesis of triols
H Me H MTM pClBn pClBnMe HMTM
87. Reagents and conditions:
93. Reagents and conditions:
Cl 2 Cl
H NMR spectrum oftriols synthetic
First proposed structures for lagunamides
Cl 2Cl
25. Synthesis forfor lagunamide
29. Synthesis of polyketides
32. Synthesis
55 The same sequence of reactions starting from 229 led to 2-epi-lagunamide
36. Synthesis of aldehyde
38. Reagents and conditions:
Findings
Conclusions
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