With this study we extend the myxobacterial Sandaracinus family by its second member, S. defensii MSr10575 and report its genome sequence featuring 21 BGCs predicted by AntiSmash. Analysis of the strain's metabolome revealed a group of alkaloid terpenoids which we named sandacrabins. Their isolation and structure elucidation prove them as farnesylated DMBs belonging to the family of alkaloid terpenoids. To the best of our knowledge, the sandacrabins represent the first prenylated DMBs of bacterial origin, for which we developed a concise biosynthesis hypothesis. Analysis of the potential genes involved, revealed that sandacrabin biosynthesis likely consists of two steps: generation of the different DMB core structures and subsequent farnesylation by a prenyltransferase. Cobalamin biosynthesis also requires the synthesis of DMB, wherefore the biosynthesis pathway that supplies DMB to Vitamin B12 biosynthesis likely also supplies the sandacrabin biosynthesis with the respective DMB precursors. Removal of the DMB C1, bound to the two vicinal nitrogen atoms, would allow subsequent generation of the two sandacrabin derivatives A and C, whereas sandacrabin B incorporates the native DMB. Besides the genes involved in cobalamin biosynthesis, we could identify several genes encoding for prenyltransferases in the S. defensii MSr10575, supporting our biosynthesis hypothesis. Substituted benzimidazoles have already been studied extensively in synthetic chemistry approaches towards their antimicrobial, antiviral, and insecticidal activities, which we could also observe for the sandacrabins. Highest structural similarity to the sandacrabins, which are described in this study, was found with synthetic monogeranylated 5,6-dimethylbenzimidazole and mono-farnesylated 1methylbenzimidazole derivatives, studied in a Tribolium chitin synthetase inhibition assay for generation of novel insecticidal compounds. Bis-terpenylated benzimidazoles however, are rarely found in literature. One bis-prenylated benzimidazole was generated by Holtgrewe et al. as an intermediate for studying the rearrangement of electron-rich N-allyldibenzotetraazafulvalenes. However, instead of DMB, it incorporates benzimidazole and its biological activities were not evaluated. Driven by the intriguing biological activities described for synthetic benzimidazole derivatives, we developed a chemical synthesis route for sandacrabin B and C produced in S. defensii in relatively low yields, allowing full characterization of their biological activities. We furthermore synthesized the mono-farnesylated congeners sandacrabin D and E, which could only be detected in trace amounts in S. defensii. MSr10575 crude extracts. The observed broadspectrum activities of the different sandacrabins derivatives, which exhibit antibiotic, insecticidal and antiviral effects generally point towards a defensive function of sandacrabins for S. defensii MSr10575. The insecticidal activity against A. pisum alongside their straightforward synthesis indicates sandacrabins B-E as potential candidates for agricultural use, as their production could easily be upscaled. The detected reduction in viral replication of the human pathogenic coronavirus HCoV229E by sandacrabin B-E is one more example of a benzimidazole exhibiting antiviral activities, much needed in times of evolving viral pandemics such as the covid-19 pandemic. Exemplified by remdesivir, the RdRp complex has already proven an excellent target for the treatment of SARS-CoV2 infections. However, structural diversity of non-nucleoside analogues targeting RdRp is low, having most of the few examples of this group suffer from poor pharmacokinetic properties. Furthermore, they do not bind to the active site of the complex, but rather to outer regions of the protein. Inhibition of the RdRp by the sandacrabins therefore marks an interesting starting point for developing nonnucleoside analogue inhibitors addressing this intriguing target. Further studies might explore the exact binding site of the sandacrabins, as well as their pharmacokinetic properties and define the structural space where inhibition is detected. As we observe cytotoxic effects at the highest concentration tested, medicinal chemistry optimization is certainly required to advance the sandacrabins as antiviral drug candidates. As sandacrabin A, contrary to the other derivatives, exhibits focused activity against B. subtilis without showing insecticidal or antiviral activity, modifications in the DMB substitution pattern (particularly at position 2) are of special interest for modifying the observed activities. The broad biological activities, which interestingly are different for the various sandacrabin derivatives, once more highlight the intriguing biosynthetic potential of rare myxobacteria and their suitability to isolate novel natural products for supplying the drug discovery pipeline.