4.6 Article

Diketopiperazine alkaloids from a mangrove rhizosphere soil derived fungus Aspergillus effuses H1-1

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 10, Issue 47, Pages 9501-9506

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c2ob26757h

Keywords

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Funding

  1. National Natural Science Foundation of China [41176120]
  2. State Key Laboratory of Drug Research [SIMM1203KF-14]
  3. Promotive research fund for excellent young and middle-aged scientists of Shandong Province [BS2010HZ027]
  4. Public Projects of State Oceanic Administration [2010418022-3]
  5. Program for Changjiang Scholars and Innovative Research Team in University [IRT0944]
  6. National Information Infrastructure Development Institute [NIIFI 10038]
  7. [HURO/0901/274/2.2.2]

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Effusin A (1), a spirobicyclic N,O-acetal derivative with an unprecedented 3',3a',5',6'-tetrahydrospiro-[piperazine-2,2'-pyrano[2,3,4-de]chromene] ring system, and a spiro-polyketide-diketopiperazine hybrid dihydrocryptoechinulin D (2) were isolated from a mangrove rhizosphere soil derived fungus, Aspergillus effuses H1-1. Their structures were determined by detailed spectroscopic analysis. Effusin A (1) and dihydrocryptoechinulin D (2) occurred as racemates, the enantiomers of which were separated and characterized by online HPLC-ECD analysis and their absolute configurations were determined by the solution TDDFT ECD calculation approach. The cytotoxic effects of 1 and 2 were preliminarily evaluated and 2 showed potent activity on P388 cells with an IC50 value of 1.83 mu M. The target of racemic 2 was also investigated and the (12R,28S,31S)-2 enantiomer showed selectivity against topoisomerase I.

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