Details
| Original language | English |
|---|---|
| Pages (from-to) | 2003-2012 |
| Number of pages | 10 |
| Journal | Beilstein Journal of Organic Chemistry |
| Volume | 15 |
| Early online date | 23 Aug 2019 |
| Publication status | E-pub ahead of print - 23 Aug 2019 |
Abstract
Withanolides are steroidal lactones widespread in Nightshade plants with often potent antiproliferative activities. Additionally, the structural diversity of this compound class holds much potential for the discovery of novel biological activity. Here, we report two newly characterised withanolides, named irinans, from Physalis peruviana with highly unusual truncated backbones that resemble mammalian androstane sex hormones. Based on biomimetic chemical reactions, we propose a model that links these compounds to withanolide biosynthesis. Irinans have potent antiproliferative activities, that are however lower than those of 4ß-hydroxywithanolide E. Our work establishes androwithanolides as a new subclass of withanolides.
Keywords
- Androstanes, Physalis peruviana, Steroids, Structure elucidation, Withanolides
ASJC Scopus subject areas
- Chemistry(all)
- Organic Chemistry
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In: Beilstein Journal of Organic Chemistry, Vol. 15, 23.08.2019, p. 2003-2012.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Isolation and characterisation of irinans, androstane-type withanolides from Physalis peruviana L.
AU - Stein, Annika
AU - Compera, Dave
AU - Karge, Bianka
AU - Brönstrup, Mark
AU - Franke, Jakob
N1 - Funding Information: This work has been carried out within the framework of the SMART BIOTECS alliance between the Technische Universität Braunschweig and the Leibniz Universität Hannover. This initiative is supported by the Ministry of Science and Culture (MWK) of Lower Saxony, Germany. LC–MS (INST 187/621) and NMR (INST 187/686-1) instruments funded by the Deutsche Forschungsgemeinschaft (DFG) were used. We thank Prof. Russell Cox for his support and helpful discussions, and Marcel Arndt for preliminary work. We thank Dr. Jörg Fohrer and colleagues for support with NMR measurements and Katja Körner and colleagues for excellent lab support.
PY - 2019/8/23
Y1 - 2019/8/23
N2 - Withanolides are steroidal lactones widespread in Nightshade plants with often potent antiproliferative activities. Additionally, the structural diversity of this compound class holds much potential for the discovery of novel biological activity. Here, we report two newly characterised withanolides, named irinans, from Physalis peruviana with highly unusual truncated backbones that resemble mammalian androstane sex hormones. Based on biomimetic chemical reactions, we propose a model that links these compounds to withanolide biosynthesis. Irinans have potent antiproliferative activities, that are however lower than those of 4ß-hydroxywithanolide E. Our work establishes androwithanolides as a new subclass of withanolides.
AB - Withanolides are steroidal lactones widespread in Nightshade plants with often potent antiproliferative activities. Additionally, the structural diversity of this compound class holds much potential for the discovery of novel biological activity. Here, we report two newly characterised withanolides, named irinans, from Physalis peruviana with highly unusual truncated backbones that resemble mammalian androstane sex hormones. Based on biomimetic chemical reactions, we propose a model that links these compounds to withanolide biosynthesis. Irinans have potent antiproliferative activities, that are however lower than those of 4ß-hydroxywithanolide E. Our work establishes androwithanolides as a new subclass of withanolides.
KW - Androstanes
KW - Physalis peruviana
KW - Steroids
KW - Structure elucidation
KW - Withanolides
UR - http://www.scopus.com/inward/record.url?scp=85071433581&partnerID=8YFLogxK
U2 - 10.3762/bjoc.15.196
DO - 10.3762/bjoc.15.196
M3 - Article
AN - SCOPUS:85071433581
VL - 15
SP - 2003
EP - 2012
JO - Beilstein Journal of Organic Chemistry
JF - Beilstein Journal of Organic Chemistry
SN - 1860-5397
ER -