Petriellin A: A novel antifungal depsipeptide from the coprophilous fungus Petriella sordida

Lee, Kit K.; Gloer, James B.; Scott, James A.; Malloch, David

doi:10.1021/jo00122a010

Cited by 34 publications

(25 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…5) was isolated from the coprophilous (dung-colonizing) fungus Petriella sordida (UAMH 7493) [36]. It is only the second natural product isolated from the genus Petriella.…”

Section: Petriellin Amentioning

confidence: 99%

Recent Developments in Depsipeptide Research

Ballard¹,

Yu²,

Wang³

2002

CMC

View full text Add to dashboard Cite

This review focuses on the major developments in depsipeptide research since 1995. Depsipeptides are bio-oligomers composed of hydroxy and amino acids linked by amide and ester bonds. Many depsipeptides show very promising biological activities, including anticancer, antibacterial, antiviral, antifungal, anti-inflammatory, and anti-clotting or anti-antherogenic properties. In this report depsipeptides exhibiting these properties are discussed. Their isolation, structural determination, and notable structural features are discussed, but their biological properties and therapeutic potentials are emphasized. Depsipeptides have shown the greatest therapeutic potential as anticancer agents. Four depsipeptides have entered clinical trials for cancer treatment. Among the antiviral compounds discovered, the callipeltins and the quinoxapeptins are particularly promising due to their inhibitory activities against HIV. These compounds have the potential to be developed as anti-AIDS drugs or to serve as lead compounds for the discovery of structurally related anti-AIDS compounds. Antifungal compounds, such as the jaspamides, may lead to therapies against many of the opportunistic infections that accompany AIDS. Anti-inflammatory compounds such as SCH217048 act as neurokinin antagonists and may lead to anti-inflammatory treatments. Some depsipeptides such as micropeptins and A90720A have been found to be effective plasmin inhibitors, which have implications as treatments for cardiovascular diseases. Compounds such as SCH58149 help control the levels of HDL and LDL.

show abstract

“…5) was isolated from the coprophilous (dung-colonizing) fungus Petriella sordida (UAMH 7493) [36]. It is only the second natural product isolated from the genus Petriella.…”

Section: Petriellin Amentioning

confidence: 99%

Recent Developments in Depsipeptide Research

Ballard¹,

Yu²,

Wang³

2002

CMC

View full text Add to dashboard Cite

show abstract

“…Petriellin A was found to have activity against Ascobolus furfuraceous (NRRL 6460) and Sordaria fimicola (NRRL 6459). 14 Structurally, petriellin A contains one R-D-hydroxycarboxylic acid and 12 L-amino acids, five of which are N-methylated. At the time of the initial communication, Lee and Gloer and co-workers 14 did not determine the absolute configuration of N-methylisoleucine and the two N-methylthreonine residues in the natural product.…”

Section: ' Introductionmentioning

confidence: 99%

“…14 Structurally, petriellin A contains one R-D-hydroxycarboxylic acid and 12 L-amino acids, five of which are N-methylated. At the time of the initial communication, Lee and Gloer and co-workers 14 did not determine the absolute configuration of N-methylisoleucine and the two N-methylthreonine residues in the natural product. Clarification of the unknown stereochemistry was later communicated by Aurelio et al 6,15 An attempted total synthesis of petriellin A via solution-phase chemistry was later reported by Aurelio et al 13 The authors constructed the "northwestern" and "southeastern" halves of their planned linear precursor.…”

Section: ' Introductionmentioning

confidence: 99%

Total Synthesis of the Antifungal Depsipeptide Petriellin A

et al. 2011

View full text Add to dashboard Cite

We report the solid-phase total synthesis of the antifungal highly modified cyclic depsipeptide petriellin A. The synthesis confirms earlier reports on the absolute configuration of the natural product. The solid-phase approach resulted in a protected linear precursor, which was cleaved from the solid support prior to cyclization and final deprotection. Use of advanced coupling agents for several hindered amides was a feature of the synthesis. The natural product was prepared in overall 5% yield.

show abstract

“…This study adds further evidence that chlorinated DMBA-related compounds are biosynthesized by cyanobacteria. Other notable structural features of itralamides A ( 3 ) and B ( 4 ) include the presence of two D-configured amino acid residues, and the relatively rare N -methylthreonine residue, which has been reported previously from a few but diverse array of organisms including a cyanobacterium,23 sponges,24 fungi,25 and an actinobacterium 26…”

Section: Resultsmentioning

confidence: 72%

Halogenated Fatty Acid Amides and Cyclic Depsipeptides from an Eastern Caribbean Collection of the Cyanobacterium Lyngbya majuscula

et al. 2009

View full text Add to dashboard Cite

A lipophilic extract of an eastern Caribbean collection of Lyngbya majuscula yielded two new halogenated fatty acid amides, grenadamides B (1) and C (2), and two new depsipeptides, itralamides A (3) and B (4), along with the known compounds hectochlorin and deacetylhectochlorin. The recently reported depsipeptide carriebowmide (5) was also present in the extract and isolated as its sulfone artifact (6). Compounds 1–4 were identified by spectroscopic methods. The configurations of the amino acid residues of 3, 4, and 6 were determined by LC-MS analyses of diastereomeric derivatives of the acid hydrolysates (advanced Marfey’s method). Based on the configurational analysis of 6, in direct comparison with authentic carriebowmide (5), a minor structural revision of 5 is proposed. Compounds 1 and 2 displayed marginal activity against the beet armyworm (Spodoptera exigua). Compounds 1–4, and 6 were assessed for general cell toxicity in human embryonic kidney (HEK293) cells. Only itralamide B (4) displayed significant cytotoxicity, showing an IC50 value of 6 ± 1 μM.

show abstract

Petriellin A: A novel antifungal depsipeptide from the coprophilous fungus Petriella sordida

Cited by 34 publications

References 0 publications

Recent Developments in Depsipeptide Research

Recent Developments in Depsipeptide Research

Total Synthesis of the Antifungal Depsipeptide Petriellin A

Halogenated Fatty Acid Amides and Cyclic Depsipeptides from an Eastern Caribbean Collection of the Cyanobacterium Lyngbya majuscula

Contact Info

Product

Resources

About