Sattahipmycin, a Hexacyclic Xanthone Produced by a Marine-Derived Streptomyces

Abstract

Sattahipmycin was isolated from the mycelium of marine-derived Streptomyces sp. GKU 257-1 by following the antibiofilm activity against E. coli NBRC 3972 throughout the purification steps. The structure of sattahipmycin was determined to be a new polycyclic xanthone related to xantholipin but lacking a dioxymethylene and a chlorinated carbon. This compound showed activity toward Gram-positive bacteria and Plasmodium falciparum, antibiofilm formation of Escherichia coli, and cytotoxicity to human cancer cell lines. Using genome sequence data, a biosynthetic pathway leading to sattahipmycin has been proposed involving an uncharacterized type II polyketide synthase biosynthetic gene cluster.

Structure-Guided Discovery of Diverse Cytotoxic Dimeric Xanthones/Chromanones from Penicillium chrysogenum C-7-2-1 and Their Interconversion Properties

“…The absorbance of each well was then measured using a microplate reader at 490 nm. 24,30 Cell Cycle Assay. Cells were seeded into 6-well plates (3.0 × 10 5 per well) and incubated overnight at 37 °C, followed by treatment with MeOH or compound 7 for 24 h, washed twice with phosphatebuffered saline (PBS), fixed in 70% ethanol for 24 h, and stained with propidium iodide (PI) (Beyotime Biotechnology, Jiangsu, China), and analyzed using a FACSCalibur flow cytometer (BD Biosciences, San Jose, CA, USA).…”

Chemistry and biosynthesis of bacterial polycyclic xanthone natural products

“…Among the hexacyclic skeletons, diverse BPXNPs exist based on their ring oxidation state. One example is the structural diversity among cervinomycins (16)(17)(18)(19)(20)(21)(22)(23)(24)(25)Fig. 4).…”

“…In kigamicins (41)(42)(43)(44)(45), the oxazolidine ring G may arise from the incorporation of an ethanolamine or alanine. In cervinomycins (16)(17)(18)(19)(20)(21)(22)(23)(24)(25), the selectivities on nitrogen donors of aminotransferases may contribute to the molecular diversity of cervinomycins (Fig. 27).…”

“…24 Secondly, these compounds contain different substituents on the δ -position (C 25 ) next to the amide, such as a methyl group existing in major compounds (xantholipin ( 33 ), 22 MDN-185 ( 34 ), 23 dehydroxanthomycin ( 35 ) 59 and sattahipmycin ( 37 , Fig. 6)), 25 and a butyryl group in Sch56036 ( 32 ).…”

“…The available genomic sequences and analysis of DNA sequences are increasingly being used to guide the discovery of BGCs. To date, BGCs for lysolipins ( 81 and 82 ), 52 FD-594 ( 75 ), 99 xantholipin ( 33 ), 47 arixanthomycins ( 38–40 ), 26 cervinomycin B and C ( 18–25 ), 18 albofungins ( 78 and 79 ), 18 calixanthomycin A ( 72 ) 61 and sattahipmycin ( 37 ) 25 have been reported. The existence of genes for type II PKSs in the BGCs confirmed the previously proposed polyketide biosynthetic pathway.…”