Polycyclic tetrahydroxanthones from Streptomyces chrestomyceticus BCC 24770

Bunyapaiboonsri, Taridaporn; Lapanun, Sanisa; Supothina, Sumalee; Rachtawee, Pranee; Chunhametha, Suwanee; Suriyachadkun, Chanwit; Boonruangprapa, Tanapong; Auncharoen, Patchanee; Chutrakul, Chanikul; Vichai, Vanicha

doi:10.1016/j.tet.2015.12.045

Cited by 26 publications

(22 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Its structure was first proposed in the 1970s (Gurevich et al, 1972(Gurevich et al, , 1974, with the original absolute stereochemistries revised based on circular dichroism studies (Onoprienko et al, 1978). Its monochlorinated analogue chloroalbofungin (2) was also isolated from a number of Streptomyces species, including recently from S. chrestomyceticus (Bunyapaiboonsri et al, 2016), and is consistent with our findings reported herein.…”

Section: Introductionsupporting

confidence: 90%

Albofungin and chloroalbofungin: antibiotic crystals with 2D but not 3D isostructurality

She

Sung

et al. 2020

Acta Crystallogr C

View full text Add to dashboard Cite

The potent antibiotics albofungin [systematic name: (1S,4R,8aR)-13-amino-1,15,16-trihydroxy-4-methoxy-12-methyl-3,4,8a,13-tetrahydro-1H-xantheno[4′,3′,2′:4,5][1,3]benzodioxino[7,6-g]isoquinoline-14,17(2H,9H)-dione, C27H24N2O9, 1] and its chlorinated analogue chloroalbofungin (the 11-chloro analogue, C27H23ClN2O9, 2) have been crystallized following their isolation from the bacterial strain Streptomyces chrestomyceticus and their structures determined by single-crystal X-ray diffraction. The novel N-aminoquinolone molecular arrangement shows N—N bond lengths of 1.4202 (16) and 1.424 (2) Å in 1 and 2, respectively. The regiochemistry of chloro substitution in the A-ring is para to the quinolone O atom, with a C—Cl bond length of 1.741 (2) Å. The absolute stereochemistry at three chiral centres of the xanthone rings (i.e. 10S, 13R and 19R) is confirmed. Both compounds crystallize in chiral Sohncke space groups consistent with enantiopurity, but are not fully isostructural. A preserved supramolecular construct (SC) confers two-dimensional (2D) isostructurality, but the SC self-associates via either a twofold screw operation in 1, giving a monoclinic P21 structure, or a twofold rotation in 2, affording a monoclinic C2 structure with a doubled unit-cell axis.

show abstract

Section: Introductionsupporting

confidence: 90%

Albofungin and chloroalbofungin: antibiotic crystals with 2D but not 3D isostructurality

She

Sung

et al. 2020

Acta Crystallogr C

View full text Add to dashboard Cite

show abstract

“…albofungin antibiotic [281] chloroalbofungin antibiotic [281] chrestoxanthones A-C antifungal [281] Streptomyces chromofuscus carazostatin carbazole alkaloids [282] Streptomyces chromofuscus herboxidiene bioactive compound [283] Streptomyces cinnamonensis 2-demethylmonensihs A, B minor congeners of monensins [284] arcyriaflavin E indolocarbazole alkaloid [285] endophenazine A antimicrobial compound [286,287] …”

Section: Streptomyces Chrestomyceticusmentioning

confidence: 99%

Database on the taxonomical characterisation and potential toxigenic capacities of microorganisms used for the industrial production of food enzymes and feed additives, which do not have a recommendation for Qualified Presumption of Safety

Benito

Ibáñez

Moncho

et al. 2017

EFSA Supporting Publications

View full text Add to dashboard Cite

The present work constitutes the external scientific report of the EFSA open call OC/EFSA/FEED/2015/01. The aim of the call was to provide EFSA with a database from a review on the taxonomical description and potential toxigenic capacities of microorganisms used for the industrial production of feed additives and food enzymes. The review includes microorganisms used as source of feed additives and food enzymes for which EFSA has received or can potentially receive applications for safety assessment, and which have not been recommended for Qualified Presumption of Safety status. The database also comprises the molecular taxonomical identifiers and biosynthetic pathways involved in the production of toxic compounds and the responsible genes. The main result of the project is shown as a database developed according to the EFSA data structure. The methodological aspects and the queries used in the systematic search, as well as the procedure applied for the screening of scientific documents retrieved are described in this report. Details are available in supplementary appendices.In total, 22970 scientific documents were screened in the literature search, from which 411 were initially selected for providing pertinent data for the scope of the project. From the review of the selected articles, 474 bioactive secondary metabolites were recorded and 59 compounds were further studied in order to obtain data on their toxicology and the conditions in which they are produced by the microorganisms used in industrial fermentations. The database generated in this project comprises details that characterise, when available, the production conditions, genes involved and toxicity of these 59 compounds. This provides information that can be used to establish safety measures when using potentially toxigenic microorganisms in industrial fermentations Disclaimer: The present document has been produced and adopted by the bodies identified above as author(s). This task has been carried out exclusively by the author(s) in the context of a contract between the European Food Safety Authority and the author(s), awarded following a tender procedure. The present document is published complying with the transparency principle to which the Authority is subject. It may not be considered as an output adopted by the Authority. The European Food Safety Authority reserves its rights, view and position as regards the issues addressed and the conclusions reached in the present document, without prejudice to the rights of the authors. Acknowledgements:We thank the following EFSA satff: Jaime Aguilera, Margarita Aguilera-Gómez, Jane Richardson, Mario Monguidi and Davide Gibin for their valuable help and collaboration throughout the project. We also would like to thank the members of AINIA: Sonia Porta, Lidia Tomás, Joaquin Espí and Juan Antonio Nieto for providing expertise in biotechnology and molecular biology and contributing with their efforts to achieve the goals of this project, and Violeta Gómez from the University of Navarra for her colla...

show abstract

“…In general, Streptomyces is described as the largest genus of Actinobacteria (Yousif et al, 2015). More than 770 species of Streptomyces have been recognized (Bunyapaiboonsri et al, 2016). Back to year (1943), species of Streptomyces for the 1 st time were introduced by Waksman and Henrici (Waksman and 2005).…”

Section: Introductionmentioning

confidence: 99%

Phylogenetic Analysis of Streptomyces spp. Isolated from Soil Samples in Sulaimani Governorate

Qadir

Shareef

et al. 2020

Polytechnic j.

View full text Add to dashboard Cite

Streptomyces species have been an important source of bioactive secondary metabolites and clinically useful for antibiotic production, including fosfomycin, daptomycin, oxytetracycline, streptomycin, and chloramphenicol. The main objective of this study was to isolate actinomycetes, especially Streptomyces from 8 soil samples that collected from two different places, which are districts in Sulaimani governorate, Kurdistan Region of Iraq. Totally, 30 diagnostic tests were carried out for representative of isolated Streptomyces depending on the color groups. The 16Sr DNA gene was sequenced, for ten isolated test strains were amplified with 2 universal primers after extraction of genomic DNA, only 8 of them were successfully sequenced. Phylogenetic analysis of 8 test strains carried out using base sequences of 16Sr DNA genes in the core genome. Four of isolated test strains were identified as a Streptomyces fulvissimus, and others were nominated as a Streptomyces anulatus. The obtained sequence data were compared with the sequence data of the closest related species in the international databases using EzTaxon Server program and (%) similarities were determined. Finally, phylogenetic analysis indicated that isolated test strains were nominated as (H001, H002, H003, and H004), which recognized members of the S. anulatus and the similarity with their type strain is 99.93%. Whereas, other four isolated test strains, including D001, D002, D003, and D004 recognized as members of the S. fulvissimus and similarity with their type strain is 100%.

show abstract

Polycyclic tetrahydroxanthones from Streptomyces chrestomyceticus BCC 24770

Cited by 26 publications

References 13 publications

Albofungin and chloroalbofungin: antibiotic crystals with 2D but not 3D isostructurality

Albofungin and chloroalbofungin: antibiotic crystals with 2D but not 3D isostructurality

Database on the taxonomical characterisation and potential toxigenic capacities of microorganisms used for the industrial production of food enzymes and feed additives, which do not have a recommendation for Qualified Presumption of Safety

Phylogenetic Analysis of Streptomyces spp. Isolated from Soil Samples in Sulaimani Governorate

Contact Info

Product

Resources

About