MINI-REVIEW Naturally occurring of α,β-diepoxy-containing compounds: origin, structures, and biological activities Vera Vil 1 & Tatyana A. Gloriozova 2 & Vladimir V. Poroikov 2 & Alexander O. Terent’ev 1 & Nick Savidov 3 & Valery M. Dembitsky 1,3,4 Received: 12 December 2018 /Revised: 19 February 2019 /Accepted: 22 February 2019 /Published online: 9 March 2019 # Springer-Verlag GmbH Germany, part of Springer Nature 2019 Abstract Diepoxy-containing compounds are widely distributed in nature. These metabolites are found in plants and marine organisms and are also produced by many microorganisms, fungi, or fungal endophytes. Many of these metabolites are antibiotics and exhibit a wide variety of biological activities. More than 80 α,β-diepoxy-containing compounds are presented in this article, which belong to different classes of chemical compounds including lipids, terpenoids, alkaloids, quinones, hydroquinones, and pyrones. The main activities that characterize α,β-diepoxy-containing compounds are antineoplastic with confidence up to 99%, antifungal with confidence up to 94%, antiinflammatory with confidence up to 92%, or antibacterial with confidence up to 78%. In addition, these metabolites can be used as a lipid metabolism regulator with a certainty of up to 81%, antiviral (Arbovirus) activity with a certainty of up to 71%, or antiallergic activity with confidence up to 69%. These data on the biological activity of diepoxy- containing compounds are of considerable interest to pharmacologists, chemists, and medical professionals who are involved in phytomedicine and related areas of science and industry. Keywords Diepoxides . Microorganisms . Fungi . Algae . Invertebrates . Plant . Activities Introduction The three-membered unit (cyclopropane)-containing com- pounds are widely distributed in nature (Tschersich et al. 2018; Wessjohann and Brandt 2003; Garson 1993), and heterocyclopropanes containing an atom of oxygen (oxiranes), nitrogen (aziridines), or sulfur (thiiranes) are also found in nature (Gloriozova and Dembitsky 2018; Dembitsky et al. 2017; Poroikov et al. 2017; Kuklev et al. 2013, 2017; Kuklev and Dembitsky 2014; Fyaz et al. 2009; Padwa and Murphree 2006; Lowden 2006; Sweeney 2002; Chew and Harpp 1993). At present, it is known that about 300 compounds, α,β- diepoxy-containing compounds (DCC), comprise a small group of natural metabolites (Dembitsky et al. 2018; Auvergne et al. 2014). The presence of an epoxy group in a molecule is assumed to increase the biological activity of the molecule due to the high reactivity of the epoxy group (Scotti et al. 2007; Kuklev and Dembitsky 2014; Ernouf et al. 2018). It can be assumed that two epoxy groups in the α,β-posi- tion in one molecule can double the biological activity? And such a molecule can be a source of highly reactive free oxy- gen. Such small molecules, at present, belong to the group of high-energy oxygen-containing non-aromatic heterocycles and they are of great interest as new pharmacophores with a wide spectrum of biological activity. Such compounds include endoperoxides, oxetanes, and α,β-epoxides (Vil et al. 2017, 2018, 2019; Terent’ev et al. 2011, 2014; Dembitsky et al. 2007 , 2018 ; Salomatina et al. 2005 ; Morisseau and Hammock 2005; Alabugin 2016; Alabugin et al. 2015). In the natural metabolites presented with this article, bio- logical activity has only been partially studied, but the activity in the main part of these compounds has not been determined. * Valery M. Dembitsky devalery@ioc.ac.ru 1 N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, Moscow, Russia 119991 2 Institute of Biomedical Chemistry, Russian Academy of Sciences, Moscow, Russia 119121 3 Centre for Applied Research and Innovation, Lethbridge College, 3000 College Drive South, Lethbridge, AB T1K 1L6, Canada 4 National Scientific Center of Marine Biology, Vladivostok, Russia 690041 Applied Microbiology and Biotechnology (2019) 103:3249–3264 https://doi.org/10.1007/s00253-019-09711-4