α-Pyrones and Diketopiperazine Derivatives from the Marine-Derived Actinomycete Nocardiopsis dassonvillei HR10-5

Fu, Peng; Li, Peipei; Qu, Hu; Wang, Yi; Chen, Dianfeng; Wang, Hui; Li, Jing; Zhu, Weiming

doi:10.1021/np200597m

Cited by 101 publications

(77 citation statements)

References 25 publications

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“…9 Structurally these gilvocarcintype polyketide glycosides differ in the nature of the sugar moiety and the side chain at C-8. [10][11][12][13][14] As part of our ongoing search for bioactive secondary metabolites from actinomycetes, [15][16][17] strain Streptomyces sp. QD01-2 was isolated from the 3-m-deep soil collected at Huiquan Square near Qingdao First Beach, China.…”

Section: Introductionmentioning

confidence: 99%

Gilvocarcin HE: a new polyketide glycoside from Streptomyces sp

Hou

et al. 2012

J Antibiot

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A new antimicrobial polyketide glycoside (1) and three known compounds, gilvocarcins H (2), V (3) and M (4) were isolated from the ethyl acetate extract of Streptomyces sp. QD01-2. The structure of (1) was established by spectroscopic analysis, X-ray single crystal diffraction and CD spectra. The new compound (1) showed potent antimicrobial activities against Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Candida albicans, with MIC values of 0.5-5.0 mM. Compound (1) also showed weak cytotoxicity against the MCF-7, K562 and P388 cell lines, with IC 50 values of 36, 39 and 45 mM, respectively. The results showed that the vinyl side chain helps to increase the cytotoxicity and antimicrobial activities of gilvocarcin-type glycosides. In addition, the NMR data of gilvocarcin H (2) were also reported for the first time. Keywords: antimicrobial activity; cytotoxicity; gilvocarcin HE; polyketide glycoside; Streptomyces INTRODUCTION Producing 13 000 bioactive metabolites described, cultured bacteria have been a prolific resource for drug discovery. 1 About 70% of these bioactive compounds have been isolated from cultured actinomycetes. 2 Among them, polyketide metabolites represent a major source for novel chemotherapeutics. 3 A particularly promising lead structure is gilvocarcin V (3), the prototype of a family of benzo[d]naphtha[1,2-b]pyran-6-one glycosides from Streptomyces spp. [4][5][6][7][8] Members of this family generally exhibit high antimicrobial and antitumor activities. 9 Structurally these gilvocarcintype polyketide glycosides differ in the nature of the sugar moiety and the side chain at C-8. [10][11][12][13][14] As part of our ongoing search for bioactive secondary metabolites from actinomycetes, 15-17 strain Streptomyces sp. QD01-2 was isolated from the 3-m-deep soil collected at Huiquan Square near Qingdao First Beach, China. Its secondary metabolites showed antibacterial activity against Staphylococcus aureus at a concentration of 100 mg ml -1 . And a series of peaks with the similar UV absorptions to those of gilvocarcin-type polyketide glycosides [4][5][6][7][8] were observed at l max 242, 274, 314 and 386 nm in the HPLC-UV profile (Supplementary Figure S7). Chemical investigation resulted in the isolation of a new gilvocarcin, gilvocarcin HE (1), along with the known gilvocarcins H (2), 18 V (3), 5 and M (4) (Figure 1). 5 New compound (1) displayed significant antimicrobial activities against S. aureus, Escherichia coli, Bacillus subtilis and Candida albicans, with MIC values of 0.5, 2.8, 5.0 and 3.6 mM, respectively. It also showed cytotoxicity against the MCF-7, K562 and P388 cell lines, with IC 50 values of 36, 39 and 45 mM, respectively.

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Section: Introductionmentioning

confidence: 99%

Gilvocarcin HE: a new polyketide glycoside from Streptomyces sp

Hou

et al. 2012

J Antibiot

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“…A large number of pyrone–containing marine natural products are known [26,27,28,29,30,31,32]. Specifically, a series of nocapyrones (A–Q) have been continuously reported from marine-derived Nocardiopsis strains with a wide range of bioactivity (Figure 8).…”

Section: Discussionmentioning

confidence: 99%

Nocapyrones: α- and γ-Pyrones from a Marine-Derived Nocardiopsis sp.

et al. 2014

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One new α-pyrone (nocapyrone R (1)), and three known γ-pyrones (nocapyrones B, H and L (2–4)) were isolated from the culture extract of a Nocardiopsis strain collected from marine sediment. Structures of these compounds were determined on the basis of spectroscopic data including NMR and MS. γ-Pyrones 2–4 were found to induce adiponectin production in murine ST-13 preadipocyte cells but the α-pyrone 1 had no activity. The absolute configuration of the anteiso-methyl branching in 4 was determined by HPLC comparison of a degraded product of 4 with standard samples as a 2:3 enantiomeric mixture of (R)- and (S)-isomers.

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“…We assume that this cluster is responsible for nocapyrone biosynthesis in strain TP-A0876. Interestingly, a variety of pyrone derivatives were isolated from marine-derived Nocardiopsis strains (11–14). The actual products of the remaining four PKS and NRPS gene clusters have not been isolated or characterized from our strain.…”

Section: Genome Announcementmentioning

confidence: 99%

Draft Genome Sequence of Marine-Derived Actinomycete Nocardiopsis sp. Strain TP-A0876, a Producer of Polyketide Pyrones

Komaki

Ichikawa²,

Hosoyama³

et al. 2014

Genome Announc

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Here we report the draft genome sequence of Nocardiopsis sp. strain TP-A0876, isolated from marine sediment, which produces polyketide-derived pyrones called nocapyrones. The genome contains three polyketide synthase (PKS) gene clusters, one of which was proposed to be responsible for nocapyrone biosynthesis. This genome sequence will facilitate the study of the potential for secondary metabolism in Nocardiopsis strains.

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α-Pyrones and Diketopiperazine Derivatives from the Marine-Derived Actinomycete Nocardiopsis dassonvillei HR10-5

Cited by 101 publications

References 25 publications

Gilvocarcin HE: a new polyketide glycoside from Streptomyces sp

Gilvocarcin HE: a new polyketide glycoside from Streptomyces sp

Nocapyrones: α- and γ-Pyrones from a Marine-Derived Nocardiopsis sp.

Draft Genome Sequence of Marine-Derived Actinomycete Nocardiopsis sp. Strain TP-A0876, a Producer of Polyketide Pyrones

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