New pyranonaphthoquinones and a phenazine alkaloid isolated from Streptomyces sp. IFM 11307 with TRAIL resistance-overcoming activity

Abstract

Four new pyranonaphthoquinones (1-4) were isolated from the liquid culture of Streptomyces sp. IFM 11307. Additionally, one new phenazine derivative (5), along with the known phenazine-1,6-dicarboxylic acid (6) were identified. The chemical structure of compounds 1-6 was elucidated by 1D and 2D NMR spectroscopy together with CD spectral analysis. Compounds 1-4 significantly overcame tumor necrosis factor-related apoptosis-inducing ligand resistance in human gastric adenocarcinoma cell lines.

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

“…4 It was identified as Streptomyces sp. and deposited in the Medical Mycology Research Center, Chiba University, Japan with code number IFM 11307.…”

“…IFM 11307 from the soil of Yoro-valley, Ichihara, Chiba prefecture, Japan, and have reported the isolation of four new pyranonaphthoquinones and one new phenazine alkaloid, yorophenazine, with TRAIL resistance-overcoming activity from this strain. 4 Further investigation of the culture extract of Streptomyces sp. IFM 11307 resulted in the isolation of another metabolite, yoropyrazone (1), possessing a naphthoiminoquinone-pyridazone structure.…”

“…7 The proposed structure of fragment I was also contained in pyranonaphthoquinone compounds isolated previously from this strain. 4 Fragment II was identified as aminobutane-2,3-diol from the 1 H-1 H COSY experiments depicted in Figure 2. 8 For a phenylacetic acid hydrazide derivative NG-061, C-8, the corresponding position of C-10a of 1, resonated at d C 132.8.…”

“…The stereochemical relationship of C-12 position with the tetrahydropyran ring moiety (C-2, C-3¢, C-4¢ and C-6¢ positions) may remain arbitrary but is likely to be the same as compounds previously isolated together from this strain. 4 The coupling constant of 1,2-diol moiety (J HÀ17,HÀ18 ) in the aminobutane-2,3-diol side chain (fragment II) was revealed to be 8.9 Hz from the 1 H NMR spectrum in DMSO-d 6 solution of 1; however, the J values of the corresponding positions of threo and erythro isomers of 1-(4-hydroxyphenyl) butane-2,3-diol (J threo ¼8.6 Hz and J erythro ¼2.3 Hz) 12 and nhatrangins A (J threo ¼4.2 Hz) 13 in the literature vary depending on the neighboring structure. Thus, the relative configuration of the C-17/C-18 position of 1 remains undefined presently.…”

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

“…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.…”