Journal Article

FZJ-2016-05401

http://join2-wiki.gsi.de/foswiki/pub/Main/Artwork/join2_logo100x88.png Cytotoxic 14-Membered Macrolides from a Mangrove-Derived Endophytic Fungus, Pestalotiopsis microspora

Liu, S.FZJ* ; Dai, H. ; Makhloufi, G. ; Heering, C. ; Janiak, C. ; Hartmann, R.FZJ* ; Mándi, A. ; Kurtán, T. ; Müller, W. E. G. ; Kassack, M. U. ; Lin, W. ; Liu, Z. ; Proksch, P. (Corresponding author)

2016
Soc. Washington, DC

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Please use a persistent id in citations: doi:10.1021/acs.jnatprod.6b00473

Abstract: Seven new 14-membered macrolides, pestalotioprolides C (2), D−H (4−8), and 7-O-methylnigrosporolide (3), together with four known analogues, pestalotioprolide B (1), seiricuprolide (9), nigrosporolide (10), and 4,7-dihydroxy-13-tetradeca-2,5,8-trienolide (11), were isolated from the mangrove-derived endophytic fungus Pestalotiopsis microspora. Their structures were elucidated by analysis of NMR and MS data and by comparison with literature data. Single-crystal X-ray diffraction analysis was used to confirm the absolute configurations of 1, 2, and 10, while Mosher’s method and the TDDFT-ECD approach were applied to determine the absolute configurations of 5 and 6. Compounds 3−6 showed significant cytotoxicity against the murine lymphoma cell line L5178Y with IC50 values of 0.7, 5.6, 3.4, and 3.9 μM, respectively, while compound 5 showed potent activity against the human ovarian cancer cell line A2780 with an IC50 value of 1.2 μM. Structure−activity relationships are discussed. Coculture of P. microspora with Streptomyces lividans caused a roughly 10-fold enhanced accumulation of compounds 5 and 6 compared to axenic fungal control.

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Contributing Institute(s):

1. Strukturbiochemie (ICS-6)

Research Program(s):

1. 552 - Engineering Cell Function (POF3-552) (POF3-552)

Appears in the scientific report 2016

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Database coverage:
; BIOSIS Previews ; Current Contents - Agriculture, Biology and Environmental Sciences ; Current Contents - Life Sciences ; IF < 5 ; JCR ; NCBI Molecular Biology Database ; Nationallizenz ; No Authors Fulltext ; SCOPUS ; Science Citation Index ; Science Citation Index Expanded ; Thomson Reuters Master Journal List ; Web of Science Core Collection ; Zoological Record

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