Structure elucidation of a new natural diketopiperazine from aMicrobispora aeratastrain isolated from Livingston Island, Antarctica

Abstract

A new natural diketopiperazine (1) was obtained from the culture broth of Microbispora aerata strain imbas-11A, isolated from penguin excrements collected on the Antarctic Livingston Island. Compound 1 was purified consecutively by solvent extraction, silica gel column chromatography and preparative HPLC. The structure of the compound was elucidated by 1D and 2D NMR experiments and mass spectrometric investigations. The absolute configuration of compound 1 was determined by amino acid analysis and NOESY correlations. A low antiproliferative and cytotoxic effect of trans-cyclo-(D-tryptophanyl-L-tyrosyl) (1) was determined with L-929 mouse fibroblast cells, K-562 human leukemia cells and HeLa human cervix carcinoma. Trans-cyclo-(D-tryptophanyl-L-tyrosyl) (1) did not show antimicrobial activity at a concentration of 50 µg per disc against Bacillus subtilis, Staphylococcus aureus, Streptomyces viridochromogenes, Escherichia coli, Candida albicans and Mucor miehei.

The secondary metabolites of rare actinomycetes: chemistry and bioactivity

“…13). 88 Linfuranone A (288) is a new furanone-containing polyketide, which was discovered in a fermentation culture of Microbispora sp. GMKU 363 isolated from the root of a Thai medicinal plant (Clinacanthus siamensis Bremek.).…”

“…2EPS was isolated. The strain produced three known 26 A previously undescribed g-pyrone, miaolienone (79), and a new butanolide, miaolinolide (80), along with 13 known compounds (81)(82)(83)(84)(85)(86)(87)(88)(89)(90)(91)(92)(93), were obtained from Actinomadura miaoliensis BCRC 16873, which was isolated from a soil sample collected in Miaoli County, Taiwan. Compounds 79 and 80 could inhibit the production of TNF-a in U937 cells in vitro signicantly, and the IC 50 values were 0.59 and 0.76 mM, respectively.…”

A new minor diketopiperazine from the sponge-derived fungus Simplicillium sp. YZ-11

“…They are extensively obtained by extraction from natural sources, but may be easily synthesised. For both natural and synthetic diketopiperazines, a wide variety of biological activities was reported, including antitumour, antiviral, antifungal and antibacterial activities (Ivanova et al 2013). In recent years, the antifouling activities of the diketopiperazines had been studied.…”

Diketopiperazines and arylethylamides produced by Schizophyllum commune, an endophytic fungus in Alchornea glandulosa

“…Diketopiperazines present biological activities such as antiviral, antifungal, antibacterial, insecticidal, antihyperglycemic agents, receptor affinities of calcium channels and serotonergic [19][20][21] . Recent studies have demonstrated that diketopiperazine trans-cyclo(D-tryptophanyl-L-tyrosyl) presented low antiproliferative and cytotoxic effect with L-929 mouse fibroblast cells, K-562 leukemia cells and human HeLa Human cervix carcinoma 22 . Several arylethylamides present phytotoxic potential 23 .…”