AB3217-A, a novel anti-mite substance produced by a strain of Streptomyces platensis.

Abstract

AB3217-A, a novel anti-mite substance, was isolated from the fermentation broth of a streptomycete strain. The strain was isolated from a soil collected at Kita-azumi, NaganoPrefecture, Japan, and identified as Streptomyces platensis AB3217. AB3217-A was purified by Amberlite IR120B, Diaion HP-20 and CM-Sephadex C-25 column chromatographies. The molecular formula was determined as C17H23NO7 by elemental analysis, MSand 13C NMRspectroscopy. The structure of AB3217-A was determined to be (IR,3S,4S,-7/?,8i?,l l i?,125',137?)-4,12,13-trihydroxy-8-(4-methoxyphenyl)-6-aza-2,9,14-trioxatncyclo-[9.2. 1.03i7]tetradecane by spectroscopic analysis and X-ray crystallographic analysis. The molecule of AB3217-Ahas unique structure that deacetylanisomycin and /?-D-xylofuranose linked through glycosidic bond and ether bond resulting in the formation of nine-membered ring. AB3217-Ashowed marked activity against the two spotted spider mite, Tetranychus urticae.

Herbicidal Secondary Metabolites from Actinomycetes: Structure Diversity, Modes of Action, and Their Roles in the Development of Herbicides

“…Compound 181 showed moderate growth inhibition of weeds with the symptom of stunt, chlorosis, and weak growth. Kanbe et al discovered AB3217A ( 182 ), AB3217B ( 183 ), and AB3217-C ( 184 , structure uncharacterized) from Streptomyces platensis, but they did not find their herbicidal activity, only the miticidal activity. , Compounds 182 and 183 were also isolated from Streptomyces sp. ME-13 for their herbicidal activity, which have a similar structure as compound 173 .…”

Methylthioxylose – a jewel in the mycobacterial crown?

“…42 Streptomyces platensis produces an insecticide substance 13 that has a xylofuranose residue locked in a nine-membered ring. 43 Citrobacter freundii produces a rhamnosyl polysaccharide 14 with pendant xylofuranosyl residues. 44 Most intriguing, however, are several reports of xylofuranosyl compounds with sulfur substituents attached to C-5 (Fig.…”

Total Synthesis of Dragocins A−C through Electrochemical Cyclization

“…[1] These intriguing molecules were isolated off the Caribbean coast near Boca del Drago from a marine cyanobacterium and were found to possess modest cytotoxic activity against human lung cancer cells (H-460). Thus far, the only related natural product to the dragocin family is AB3217-A [2] (2; previously synthesized in 26 steps by Nakata [3] ), an anti-mite substance which features a near identical framework, but lacks the unique C4' oxidation found on dragocins AÀ C. Notably, this C4' functionalization is unprecedented in the natural product space, with the exception of nucleocidin, [4] a C4' fluorinated nucleoside. Aside from this unusual feature, the dragocins contain an alluring central 9-membered ring system which consists of a highly oxidized pyrrolidine harboring four contiguous stereocenters and an electronrich arene, all cemented upon a polar ribose moiety.…”