Actinopyrones A, B and C, new physiologically active substances. I. Producing organism, fermentation, isolation and biological properties.

Yano, Ken’ichi; Yokoi, Kouichi; Sato, Junichi; Oono, Junji; Kouda, Tadayuki; Ogawa, Yoichiro; Nakashima, Tomoki

doi:10.7164/antibiotics.39.32

Cited by 30 publications

(12 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…5 Other related metabolites, actinopyrones A (4), B (5) and C (6), have been produced by Streptomyces pactum. 9,10 They commonly contain a 2,3-dehydro C 17 side chain, whereas 1, 2 and 3 have a 1,2-dehydro side chain. Among them, only 1 contains a cis olefin moiety.…”

Section: Discussionmentioning

confidence: 99%

“…The actinopyrone-group antibiotics show various activities including antimicrobial activity, cytotoxic activity, vasodilating activity and EGF signaling inhibitory activity. 5,9 Their structural features are related to those of the piericidin-family antibiotics, 11 which consist of a similar or the same side chain and a substituted pyridine ring. Among them, piericidin A has been reported to inhibit the transcriptional expression of GRP78 induced by ER stress.…”

Section: Discussionmentioning

confidence: 99%

See 1 more Smart Citation

Actinopyrone D, a new downregulator of the molecular chaperone GRP78 from Streptomyces sp.

et al. 2014

View full text Add to dashboard Cite

A new downregulator of the molecular chaperone GRP78, actinopyrone D, was isolated together with a known related compound, PM050463, from Streptomyces sp. RAG92. The molecular formula of actinopyrone D was established as C25H36O4 by high-resolution FAB-MS. NMR spectroscopic analysis revealed the structure of actinopyrone D, which consists of an α-methoxy-γ-pyrone ring and a C17 side chain containing a cis olefin moiety. Actinopyrone D and PM050463 dose-dependently inhibited 2-deoxyglucose-induced luciferase expression in HT1080 human fibrosarcoma cells transfected with a luciferase reporter plasmid containing the GRP78 promoter. Actinopyrone D inhibited GRP78 protein expression and induced cell death under endoplasmic reticulum stress.

show abstract

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Actinopyrone D, a new downregulator of the molecular chaperone GRP78 from Streptomyces sp.

et al. 2014

View full text Add to dashboard Cite

show abstract

“…FKI-1083 [7]. The structure of 1 contains 2-methoxy-3,5-dimethyl-gpyrone similar to that of actinopyrone A (3) [8,9], aureothin (4) [10ϳ12], neoaureothin (spectinabilin, 5)…”

Section: Introductionmentioning

confidence: 99%

“…[13ϳ15], kalkipyrone (6) [16], and podopyrones (7,8) [17ϳ19]. In this report, we describe the taxonomy of the producing strain and the fermentation, isolation, structure elucidation, and biological properties of 1.…”

Section: Introductionmentioning

confidence: 99%

Verticipyrone, a New NADH-fumarate Reductase Inhibitor, Produced by Verticillium sp. FKI-1083

Shiomi

Suzuki

et al. 2006

J Antibiot

View full text Add to dashboard Cite

A new NADH-fumarate reductase inhibitor, verticipyrone, was isolated from the cultured broth of a fungus, Verticillium sp. FKI-1083. The structure was established as (E)-2-methoxy-3,5-dimethyl-6-(3-methyl-2-undecenyl)-4H-pyran-4-one. Verticipyrone exhibited an IC 50 value of 0.88 nM against NADH-fumarate reductase of Ascaris suum. Verticipyrone inhibited both Ascaris and bovine heart complex I, and its synthetic analogue, 8,9-dihydro-8-hydroxyverticipyrone, showed good selectivity against Ascaris complex I.

show abstract

“…This compound showed toxicity to brine shrimp (1 µg/mL) and goldfish (2 µg/mL) and was structurally related to the actinopyrones, which were obtained from a Streptomyces sp. (Yano et al, 1986a; Yano et al, 1986b). The actinopyrones have displayed a diverse suite of bioactivities including anti-microbial, cytotoxicity, vasodilating properties, and EGF signaling inhibitory properties (Schleissner et al, 2011; Yano et.…”

Section: Introductionmentioning

confidence: 99%

Kalkipyrone B, a marine cyanobacterial γ-pyrone possessing cytotoxic and anti-fungal activities

et al. 2016

View full text Add to dashboard Cite

Bioassay-guided fractionation of two marine cyanobacterial extracts using the H-460 human lung cancer cell line and the OVC-5 human ovarian cancer cell line led to the isolation of three related α-methoxy-β, β’-dimethyl-γ-pyrones each containing a modified alkyl chain, one of which was identified as the previously reported kalkipyrone and designated kalkipyrone A. The second compound was an analog designated kalkipyrone B. The third was identified as the recently reported yoshipyrone A, also isolated from a marine cyanobacterium. Kalkipyrone A and B were obtained from a field-collection of the cyanobacterium Leptolyngbya sp. from Fagasa Bay, American Samoa, while yoshipyrone A was isolated from a field-collection of cyanobacteria (cf. Schizothrix sp.) from Panama. One-dimensional and two-dimensional NMR experiments were used to determine the overall structures and relative configurations of the kalkipyrones, and the absolute configuration of kalkipyrone B was determined by 1H NMR analysis of diastereomeric Mosher’s esters. Kalkipyrone A showed good cytotoxicity to H-460 human lung cancer cells (EC50 = 0.9 µM), w M), while kalkipyrone B and yoshipyrone A were less active (EC50 = 9.0 µM and > 10 µM, respectively). Both kalkipyrone A and B showed moderate toxicity to Saccharomyces cerevisiae ABC16-Monster strain (IC50 = 14.6 and 13.4 µM, respectively), whereas yoshipyrone A was of low toxicity to this yeast strain (IC50 = 63.8 µM).

show abstract

Actinopyrones A, B and C, new physiologically active substances. I. Producing organism, fermentation, isolation and biological properties.

Cited by 30 publications

References 13 publications

Actinopyrone D, a new downregulator of the molecular chaperone GRP78 from Streptomyces sp.

Actinopyrone D, a new downregulator of the molecular chaperone GRP78 from Streptomyces sp.

Verticipyrone, a New NADH-fumarate Reductase Inhibitor, Produced by Verticillium sp. FKI-1083

Kalkipyrone B, a marine cyanobacterial γ-pyrone possessing cytotoxic and anti-fungal activities

Contact Info

Product

Resources

About