New bhimamycins from Streptomyces sp. AK 671*.

Jetter, Philipp, Steinert, Claudia, Knauer, Michael, Zhang, Guoliang, Bruhn, Torsten, Wiese, Jutta , Imhoff, Johannes F. , Fiedler, Hans-Peter and Bringmann, Gerhard (2013) New bhimamycins from Streptomyces sp. AK 671*. The Journal of Antibiotics, 66 . pp. 719-726. DOI 10.1038/ja.2013.82.

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Abstract

From the wild-type strain Steptomyces sp. AK 671, three nitrogen-containing octaketides were isolated, bhimamycins F, H and I, besides the known azaanthraquinone utahmycin A and polyketide shunt products SEK 4, SEK 4b, mutactin, dehydromutactin and EM18. The structures were characterized by MS and NMR experiments. The hitherto unknown absolute configuration of the two enantiomers of EM18 was determined by online-CD spectroscopy and quantum-chemical CD calculations. Bhimamycins H and I show weak antibacterial activities, whereas the enzyme phosphodiesterase 4 is strongly inhibited by bhimamycins H and I, which has never been reported for nitrogen-containing octaketides. In addition, bhimamycin H inhibits the enzyme glycogen synthase kinase-3β.

Document Type: Article
Additional Information: WOS:000328889500006
Keywords: bhimamycins; CD; EM18; octaketides; Streptomyces; structure elucidation
Research affiliation: OceanRep > GEOMAR > FB3 Marine Ecology > FB3-MI Marine Microbiology
OceanRep > GEOMAR > Applied R&D > Centre for Marine Substances (KiWiZ)
Refereed: Yes
Open Access Journal?: No
DOI etc.: 10.1038/ja.2013.82
ISSN: 0021-8820
Projects: KIWIZ, Aufbau einer Reinsubstanz-Bibliothek mariner Naturstoffe, Future Ocean
Date Deposited: 04 Dec 2013 14:24
Last Modified: 18 Jan 2018 13:50
URI: http://oceanrep.geomar.de/id/eprint/22536

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