Yoropyrazone, a new naphthopyridazone alkaloid isolated from Streptomyces sp. IFM 11307 and evaluation of its TRAIL resistance-overcoming activity

Abstract

A new naphthopyridazone derivative, yoropyrazone (1), has been isolated from Streptomyces sp. IFM 11307. The structure of the new compound was established on the basis of spectroscopic analyses. Compound 1 (10 mM) in combination with TRAIL moderately showed cytotoxic activity in sensitizing TRAIL-resistant human gastric adenocarcinoma (AGS) cells.

Marine actinomycete crude extracts with potent TRAIL-resistance overcoming activity against breast cancer cells

“…Actinomycetes are characterized by the production of various types of colored compounds (i.e. anthraquinones and phenazines) with TRAIL-resistance overcoming activity in different cancer cell lines (25,26,28,29). Therefore, the TRAIL-resistance overcoming activities of the 21 crude extracts were investigated.…”

“…Marine actinomycetes are considered as an unexplored source of biologically active secondary metabolites including antibacterial, anti-fungal, anti-malarial, anti-inflammatory, and antitumor (20)(21)(22)(23)(24)(25). Several natural products derived from terrestrial and marine actinomycetes were investigated for their TRAIL-resistance overcoming activities and the molecular mechanisms that trigger the induction of apoptosis were determined (25)(26)(27)(28)(29)(30). In this study, we investigated TRAILresistance overcoming activity of several crude extracts of marine actinomycetes isolated from the Red Sea.…”

Elmenols C-H, new angucycline derivatives isolated from a culture of Streptomyces sp. IFM 11490

“…The strain was cultured in Waksman medium 16 at 28°C for 3 days on a reciprocal shaker. Working up of the crude extract resulted in the isolation of five new compounds (1-5; Figure 1) along with the known LS1924A (10) 17 , 6-deoxy-8-methylrabelomycin (11) 18 and tetrangulol methyl ether (12). 19 In addition, previously isolated elmonin (7) and elmenols A (8) and B (9) 14 were detected by the LC-MS analysis.…”

“…Thus, compounds 2 and 1 are epimers at C-1. Based on these results, the structure of 2 was assigned to elmenol D. Compounds 1 and 2 are new members of angucyclines and may be a product of a Baeyer-Villiger-style oxidation of tetrangulol methyl ether (12). 23 Compounds 3 and 4 were obtained as brown solids.…”

“…7,8 In the continuation of our search for new bioactive natural products from actinomycetes, 9 we collected sea water and soil samples from different areas in Japan. Our laboratory reported the isolation of aotaphenazine 10 , sulfotanone 11 , yoropyrazone 12 and different pyranonaphtaquinone derivatives 13 from Streptomyces sps. These compounds exhibited the ability to overcome tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) resistance in human gastric adenocarcinoma (AGS) cells.…”