Isolation and characterisation of irinans, androstane-type withanolides from Physalis peruviana L.

• Annika Stein,
• Dave Compera,
• Bianka Karge,
• Mark Brönstrup and
• Jakob Franke

Beilstein J. Org. Chem. 2019, 15, 2003–2012, doi:10.3762/bjoc.15.196

• 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; Introduction Traditional medicine has long been a source of inspiration for modern drug

• Physalis [3], resulting in more than 300 known representatives [3]. Physalis peruviana is a withanolide producer of particular relevance as it is widely cultivated for its edible berries [4]. So far, several withanolides have been reported from P. peruviana and other Physalis species, most prominently