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Pyriculins A and B, two monosubstituted hex-4-ene-2,3-diols and other phytotoxic metabolites produced by Pyricularia grisea isolated from buffelgrass (Cenchrus ciliaris)

TitlePyriculins A and B, two monosubstituted hex-4-ene-2,3-diols and other phytotoxic metabolites produced by Pyricularia grisea isolated from buffelgrass (Cenchrus ciliaris)
Publication TypeArticolo su Rivista peer-reviewed
Year of Publication2017
AuthorsMasi, M., Meyer S., Górecki M., Mandoli A., Di Bari L., Pescitelli G., Cimmino A., Cristofaro M., Clement S., and Evidente A.
JournalChirality
Volume29
Pagination726-736
ISSN08990042
Keywords2 dioxaborolane, 2 phenyl 1, 3, 4, 4 dihydronaphthalen 1(2h) one, 8 trihydroxy 3, article, carbon nuclear magnetic resonance, Cenchrus, Cenchrus ciliaris, chemistry, Chirality, chromatophore, circular dichroism, coleoptile, controlled study, Density functional theory, electrospray mass spectrometry, epipyriculol, fungus isolation, germination, glycol, Glycols, heteronuclear multiple bond correlation, heteronuclear single quantum coherence, high resolution electrospray ionization mass spectrometry, isosclerone, Magnaporthe grisea, metabolism, microbiology, molecular mechanics, nonhuman, physiology, phytotoxicity, plant toxin, priority journal, proton nuclear magnetic resonance, Pyricularia grisea, pyriculin a, pyriculin b, trans 3, unclassified drug
Abstract

Pyricularia grisea has been identified as a foliar pathogen on buffelgrass (Cenchrus ciliaris) in North America and was studied as a potential source of phytotoxins for buffelgrass control. Two monosubstituted hex-4-ene-2,3-diols, named pyriculins A and B, were isolated from its culture filtrate organic extract together with (10S,11S)-(−)-epipyriculol, trans-3,4-dihydro-3,4,8-trihydroxy-1(2H)-napthalenone, and (4S)-(+)-isosclerone. Pyriculins A and B were characterized by spectroscopic (essentially nuclear magnetic resonance [NMR], High-resolution electrospray ionization mass spectrometry [HRESIMS]) and chemical methods such as (4E)-1-(4-hydroxy-1,3-dihydroisobenzofuran-1-yl)hex-4-ene-2,3-diols. The relative and absolute configuration of these compounds was determined by a combination of spectroscopic (NMR, electronic circular dichroism [ECD]) and computational tools. When bioassayed in a buffelgrass coleoptile and radicle elongation test, (10S,11S)-(−)-epipyriculol proved to be the most toxic compound. Seed germination was much reduced and slowed with respect to the control and radicles failed to elongate. All five compounds delayed germination, but only (10S,11S)-(−)-epipyriculol was able to prevent radicle development of buffelgrass seedlings. It had no effect on coleoptile elongation, while the other four compounds caused significantly increased coleoptile development relative to the control. © 2017 Wiley Periodicals, Inc.

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URLhttps://www.scopus.com/inward/record.uri?eid=2-s2.0-85029379786&doi=10.1002%2fchir.22744&partnerID=40&md5=57549bc8fa4ff5f2cbf890a4527bae7e
DOI10.1002/chir.22744
Citation KeyMasi2017726