Details
| Original language | English |
|---|---|
| Pages (from-to) | 2200-2213 |
| Number of pages | 14 |
| Journal | Chemistry - a European journal |
| Volume | 24 |
| Issue number | 9 |
| Early online date | 19 Jan 2018 |
| Publication status | Published - 9 Feb 2018 |
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 Database. 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.
Keywords
- Kishis′s Universal Database, macrolide, Mosher's method, polyketides, total synthesis
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Organic Chemistry
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In: Chemistry - a European journal, Vol. 24, No. 9, 09.02.2018, p. 2200-2213.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - The Rickiols
T2 - 20-, 22-, and 24-membered Macrolides from the Ascomycete Hypoxylon rickii
AU - Surup, Frank
AU - Kuhnert, Eric
AU - Böhm, Andreas
AU - Pendzialek, Tim
AU - Solga, Danny
AU - Wiebach, Vincent
AU - Engler, Hauke
AU - Berkessel, Albrecht
AU - Stadler, Marc
AU - Kalesse, Markus
N1 - Publisher Copyright: © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Copyright: Copyright 2018 Elsevier B.V., All rights reserved.
PY - 2018/2/9
Y1 - 2018/2/9
N2 - 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 Database. 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.
AB - 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 Database. 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.
KW - Kishis′s Universal Database
KW - macrolide
KW - Mosher's method
KW - polyketides
KW - total synthesis
UR - http://www.scopus.com/inward/record.url?scp=85040730001&partnerID=8YFLogxK
U2 - 10.1002/chem.201704928
DO - 10.1002/chem.201704928
M3 - Article
C2 - 29168908
AN - SCOPUS:85040730001
VL - 24
SP - 2200
EP - 2213
JO - Chemistry - a European journal
JF - Chemistry - a European journal
SN - 0947-6539
IS - 9
ER -