Novel spirooxindole alkaloid derivatives from the medicinal insect Blaps japanensis and their biological evaluation.

[Display omitted] • 15 new compounds were isolated from the whole bodies of Blaps japanensis. • Compounds 1–3 are novel spiroindole alkaloids with a unique spiro[ chromane -4,3′- indoline ]-2,2′-dione motif. • Biological assay revealed that compounds could inhibit human cancer cells (A549, Huh-7, and K562), JAK3, ROCK1, COX-2, and extracellular matrix in rat renal proximal tubular cells. Blapspirooxindoles A–C (1 – 3), three novel spirooxindole alkaloids with a unique spiro[ chromane -4,3′- indoline ]-2,2′-dione motif, blapcumaranons A and B (4 and 5), two new 2-cumaranon derivatives, blapoxindoles A–J (6 – 15), ten new oxindole alkaloid derivatives, along with one known compound (16), were isolated from the whole bodies of Blaps japanensis. Their structures including absolute configurations were determined by using spectroscopic, X-ray crystallographic, and computational methods. Compounds 1 – 11 and 13 exist as racemic mixtures in nature, and their (–)- and (+)-antipodes were separated by chiral HPLC. Biological evaluations of these compounds were determined with multiple assays including anti-tumor, anti-inflammatory, and renal protection activities in vitro. Several compounds displayed effective activity in one or more assays. [ABSTRACT FROM AUTHOR]