Universität zu Köln

Surup, Frank ORCID: 0000-0001-5234-8525, Kuhnert, Eric ORCID: 0000-0002-0443-9091, Boehm, Andreas, Pendzialek, Tim, Solga, Danny, Wiebach, Vincent ORCID: 0000-0003-4543-9204, Engler, Hauke ORCID: 0000-0003-1538-5444, Berkessel, Albrecht ORCID: 0000-0003-0470-7428, Stadler, Marc ORCID: 0000-0002-7284-8671 and Kalesse, Markus (2018). The Rickiols: 20-, 22-, and 24-membered Macrolides from the Ascomycete Hypoxylon rickii. Chem.-Eur. J., 24 (9). S. 2200 - 2214. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1521-3765

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Abstract

In preceding studies the neotropical ascomycete Hypoxylon rickii turned out to be a prolific source of new secondary metabolites, considering that we had obtained terpenoids with five different scaffolds along with a series of terphenyls. From the mycelial extracts of a 70 L scale fermentation of this strain we additionally isolated nine new macrolides (1-9) by RP-HPLC. The planar structures were elucidated by NMR spectroscopy complemented by HR-ESIMS. The relative configurations were assigned by J-based configuration analyses and confirmed by Kishi's Universal Data-base. Subsequently, the absolute configurations were assigned by Mosher's method using the shift analysis of a tetra-MTPA derivative. For rickiol A (1) and E (5) we observed transesterification of 20-membered ring structures to 22-membered isomers rickiol A2 (6) and E2 (7), and to 24-membered isomers rickiol A3 (8) and rickiol E3 (9), respectively. Cytotoxic effects and moderate antibiotic activity against Gram-positive bacteria were observed for 1-8 and 1-6 and 8, respectively. The total synthesis of rickiol E3 (9) established easier access to these compounds.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Surup, Frank UNSPECIFIED orcid.org/0000-0001-5234-8525 UNSPECIFIED Kuhnert, Eric UNSPECIFIED orcid.org/0000-0002-0443-9091 UNSPECIFIED Boehm, Andreas UNSPECIFIED UNSPECIFIED UNSPECIFIED Pendzialek, Tim UNSPECIFIED UNSPECIFIED UNSPECIFIED Solga, Danny UNSPECIFIED UNSPECIFIED UNSPECIFIED Wiebach, Vincent UNSPECIFIED orcid.org/0000-0003-4543-9204 UNSPECIFIED Engler, Hauke UNSPECIFIED orcid.org/0000-0003-1538-5444 UNSPECIFIED Berkessel, Albrecht UNSPECIFIED orcid.org/0000-0003-0470-7428 UNSPECIFIED Stadler, Marc UNSPECIFIED orcid.org/0000-0002-7284-8671 UNSPECIFIED Kalesse, Markus UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-196070
DOI:	10.1002/chem.201704928
Journal or Publication Title:	Chem.-Eur. J.
Volume:	24
Number:	9
Page Range:	S. 2200 - 2214
Date:	2018
Publisher:	WILEY-V C H VERLAG GMBH
Place of Publication:	WEINHEIM
ISSN:	1521-3765
Language:	English
Faculty:	Faculty of Mathematics and Natural Sciences
Divisions:	Faculty of Mathematics and Natural Sciences > Department of Chemistry > Institute of Organic Chemistry
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language STRUCTURE ELUCIDATION; SECONDARY METABOLITE; NATURAL-PRODUCTS; A-E; BIOSYNTHESIS; CONFIGURATION; CONFORMATION; XYLARIACEAE; ASSIGNMENT; TERPENOIDS Multiple languages Chemistry, Multidisciplinary Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/19607