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Bioorg Med Chem Lett ; 26(10): 2438-2441, 2016 05 15.
Article in English | MEDLINE | ID: mdl-27080179

ABSTRACT

Three new diketopiperazines (1-3), cyclo(l-Pro-d-trans-Hyp) (1), cyclo(l-Pro-d-Glu) (2), and cyclo(d-Pro-d-Glu) (3) and five known diketopiperazines (4-8) were isolated from the endolichenic fungus Colpoma sp. CR1465A identified from the Costa Rican plant Henriettea tuberculosa (Melatomataceae). The structures of the new compounds 1-3 were elucidated using a combination of extensive spectroscopic analyses, including 2D NMR and HR-MS, and their absolute configurations were determined by a combination of NOESY analysis and Marfey's method. Cyclo(l-Pro-d-allo-Thr) (4) was recently isolated from a South China Sea marine sponge Callyspongia sp., but its NMR spectroscopic data were not reported, and cyclo(l-Pro-l-Asp) (5) was previously reported but only as a synthetic product. The NMR data assignments of compounds 4 and 5 are reported for the first time. All of the isolated compounds were tested for antifungal and antimicrobial properties.


Subject(s)
Anti-Bacterial Agents/pharmacology , Antifungal Agents/pharmacology , Callyspongia/chemistry , Diketopiperazines/chemistry , Diketopiperazines/pharmacology , Peptides, Cyclic/chemistry , Peptides, Cyclic/pharmacology , Animals , Anti-Bacterial Agents/chemistry , Antifungal Agents/chemistry , Costa Rica , Drug Evaluation, Preclinical/methods , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests
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