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, 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:
CreatorsEmailORCIDORCID Put Code
Surup, FrankUNSPECIFIEDorcid.org/0000-0001-5234-8525UNSPECIFIED
Kuhnert, EricUNSPECIFIEDorcid.org/0000-0002-0443-9091UNSPECIFIED
Boehm, AndreasUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Pendzialek, TimUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Solga, DannyUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Wiebach, VincentUNSPECIFIEDorcid.org/0000-0003-4543-9204UNSPECIFIED
Engler, HaukeUNSPECIFIEDorcid.org/0000-0003-1538-5444UNSPECIFIED
Berkessel, AlbrechtUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Stadler, MarcUNSPECIFIEDorcid.org/0000-0002-7284-8671UNSPECIFIED
Kalesse, MarkusUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
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: Unspecified
Divisions: Unspecified
Subjects: no entry
Uncontrolled Keywords:
KeywordsLanguage
STRUCTURE ELUCIDATION; SECONDARY METABOLITE; NATURAL-PRODUCTS; A-E; BIOSYNTHESIS; CONFIGURATION; CONFORMATION; XYLARIACEAE; ASSIGNMENT; TERPENOIDSMultiple languages
Chemistry, MultidisciplinaryMultiple languages
Refereed: Yes
URI: http://kups.ub.uni-koeln.de/id/eprint/19607

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