Abstract
Two new secondary metabolites, svalbamides A (1) and B (2), were isolated from a culture extract of Paenibacillus sp. SVB7 that was isolated from surface sediment from a core (HH17-1085) taken in the Svalbard archipelago in the Arctic Ocean. The combinational analysis of HR-MS and NMR spectroscopic data revealed the structures of 1 and 2 as being lipopeptides bearing 3-amino-2-pyrrolidinone, d-valine, and 3-hydroxy-8-methyldecanoic acid. The absolute configurations of the amino acid residues in svalbamides A and B were determined using the advanced Marfey’s method, in which the hydrolysates of 1 and 2 were derivatized with l- and d- forms of 1-fluoro-2,4-dinitrophenyl-5-alanine amide (FDAA). The absolute configurations of 1 and 2 were completely assigned by deducing the stereochemistry of 3-hydroxy-8-methyldecanoic acid based on DP4 calculations. Svalbamides A and B induced quinone reductase activity in Hepa1c1c7 murine hepatoma cells, indicating that they represent chemotypes with a potential for functioning as chemopreventive agents.
Highlights
Marine habitats were generally recognized as extreme environments exposing organisms to conditions of high salt, high pressure, and hypoxia, forcing them to develop unique physiologies in comparison to their terrestrial counterparts
In our continuing efforts to search for new bioactive microbial compounds from extreme marine environments, we explored the chemistry of bacterial strains from the Arctic Ocean
SVB7 led to the discovery and structural elucidation of two new pyrrolidinone-bearing lipodipeptides, svalbamides A (1) and B (2), in which QR activity could be induced
Summary
Marine habitats were generally recognized as extreme environments exposing organisms to conditions of high salt, high pressure, and hypoxia, forcing them to develop unique physiologies in comparison to their terrestrial counterparts. Most (62.5%) of the new marine-bacterial molecules were derived from the single genus Streptomyces. The chemical examination of bacteria inhabiting the Arctic Ocean—a more extreme habitat than tropical or subtropical oceans that remains poorly investigated—represents a promising strategy for the discovery of new bioactive molecules. In our continuing efforts to search for new bioactive microbial compounds from extreme marine environments, we explored the chemistry of bacterial strains from the Arctic Ocean. In our continuing efforts to search for new bioactive microbial compounds from extreme marine environments, we explored the chemistry of bacterial strains from the Arctic CacadcaaOoolnnin-bdcnnda1aeiactlt0layiCiaay2nnnlsns-7be.ie1issinsnOc0ctaiath2aasunan7rolnrlsodmccdmiimhisnftaorfaoriorootcarcgipmigctautieuhinlrsonaoescl[ptedyh4r[eh4de]ae.loo]-msy.VIornenaeIi—n—nsc-nteVahnott—fli—whrnospoi-fnsostrSrmtw-ooutsnSrfmtodieteuSlrpywintdeSntr,epoytegwwmbrt,poeewoetypmbonfctdemeoeyzAinsmcdvoyzreebxyiccsovrecaatxsseeibczcisartfaiseszinsscpeiriptefitndi.re.a-aeebArltdi-AhinebsaReatsRtelrThrpaTalsi5erehnit5indryncpgasolcghtoiclooinylcgoneloslletmhcoehmntiagcenepybtpedheoidnootdfauifiyurnsbnboncfgoiamdrodtfocivstsntbhmteettghaerhrhceyiaattaAthhEtetofrerieaoifcninsrtaaAEhtihccrifaShirtbobisicOeibcrttitmotceicCcSesrChiiiiaacOadbeannanmene-lc.rdeiiicaadannal. .CCuultlivtiavtaiotinonininliqliuqiudidmmedeiadiaanadntdhethLeCL/MC/SM-baSs-ebdascehdemchiceaml ical eexxaammiinnaattiioonnooffththeesstrtaraininPPaeaneinbiabcailcliullsussps.pS.VSBV7Bid eindteifnietidfiethdethperopdruocdtiuocntioofnporef vpioreuvsiloyusly uunnrreeppoorrtteedd mmoolleeccuulleess wwiitthh tthhee mmoolleeccuullaarr iioonnss aatt mm//zz338844..SSccaalilningg-u-uppoofftthheeccuultltuurreeeennaa-bled ublsetdoupsutroifpyutrwifyo tnweownceowmcpoomupnodusn, dsvs,aslbvaamlbaidmeisdAes aAndanBd, Ba,nadnsdusbusbesqeuqeunetnlytlyeleulucicdidaatetetheir sthtreuircstutrruecstubryessbpyecstpreocstcroopsciocpainc aalnyasliyss,isc,hcehmemiciacladl deerirvivaattiizzaattiioonn,, aannddqquuaanntutummmmecehcahna-nicsbicass-bedasceadlccuallcautiloanti.oHn.eHree,rwe,ewreepreoprtortht ethsetrsutrcutuctruarladl edteetremrminiantaitoinonoof fsvsvaalblbaammidideessAAaannddB (1, 2B;(F1i,g2u; rFeig1u)raelo1)naglownigthwtihtheitrhbeiorlboigoilcoaglicaacltiavcittiyv.ity. In aallll pphhyyllooggeenneetticictrtereeessininfefrerrerdedbybymmaxaimxiummumlikleilkiheloiohdo,onde,ingheibgohrb-jooirn-jionign,ianngd, amnidnimmiunmim- umeevvoolluuttiioonnmmeeththoodds,s,stsrtarianinSVSVB7B7wwasalsolcoacteadtewdiwthiitnhitnhethPeaePnaibeanciiblalucsillculasdcelaadnedafnodrmfoedrmaed a rroobbuusstt ccllaaddeewwitihthPP..mmaayysiseinensissisanadndP.Pt.etrerrarea, ep,rporvoidviindgincglecalreasurpspuoprpt ofortr fiotsrgitesnugesnbueisnbgeing cmSSccmollVVaaaanysBysBfssss7i7iiriifefiemiiinsnesesedsadiadissmamaSusSsXesXePmi-Pmn-4a4abg9ebe9neTnweTirabrihobnaaocafodnifclPldeil>Plua-l>agesu9nee8s(9nin.Fb78(ioaibF%.gcm7aiuig%cl1elriuul6els1srSuee26msq)rS2.uRma)BryeN.aRnsayiABscNeseinaindAgessgnieesosngd.anieenHso.natsohnHleeyweqsstoueheifwsvoeqe.nereumrfcvoe,eeanirnrtsmc,iicoemilannusticsiilooamiloufrnniisttlhiyoaooe,frfniitrttshyooti,rebfsaiustilrnitsoikrtsbaeSculilVliynaksBtdtSe7helcVyamlwBattud7shittseamhrtatwbiPusneit.strthabiPne. confirmed using whole-genome sequencing analysis
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