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LOLO2_EPIUN
ID   LOLO2_EPIUN             Reviewed;         362 AA.
AC   Q5MNH6;
DT   23-MAY-2018, integrated into UniProtKB/Swiss-Prot.
DT   01-FEB-2005, sequence version 1.
DT   03-AUG-2022, entry version 60.
DE   RecName: Full=2-oxoglutarate-dependent dioxygenase lolO2 {ECO:0000303|PubMed:15654104};
DE            EC=1.14.-.- {ECO:0000269|PubMed:29537853};
DE   AltName: Full=Loline biosynthesis cluster 2 protein O {ECO:0000303|PubMed:15654104};
GN   Name=lolO2 {ECO:0000303|PubMed:15654104};
GN   Synonyms=lolO {ECO:0000303|PubMed:15654104};
OS   Epichloe uncinata (Endophyte fungus) (Neotyphodium uncinatum).
OC   Eukaryota; Fungi; Dikarya; Ascomycota; Pezizomycotina; Sordariomycetes;
OC   Hypocreomycetidae; Hypocreales; Clavicipitaceae; Epichloe.
OX   NCBI_TaxID=5050;
RN   [1]
RP   NUCLEOTIDE SEQUENCE [GENOMIC DNA], INDUCTION, AND FUNCTION.
RC   STRAIN=CBS 102646;
RX   PubMed=15654104; DOI=10.1534/genetics.104.035972;
RA   Spiering M.J., Moon C.D., Wilkinson H.H., Schardl C.L.;
RT   "Gene clusters for insecticidal loline alkaloids in the grass-endophytic
RT   fungus Neotyphodium uncinatum.";
RL   Genetics 169:1403-1414(2005).
RN   [2]
RP   FUNCTION.
RX   PubMed=15861432; DOI=10.1002/cbic.200400327;
RA   Blankenship J.D., Houseknecht J.B., Pal S., Bush L.P., Grossman R.B.,
RA   Schardl C.L.;
RT   "Biosynthetic precursors of fungal pyrrolizidines, the loline alkaloids.";
RL   ChemBioChem 6:1016-1022(2005).
RN   [3]
RP   FUNCTION.
RX   PubMed=16755627; DOI=10.1002/cbic.200600066;
RA   Faulkner J.R., Hussaini S.R., Blankenship J.D., Pal S., Branan B.M.,
RA   Grossman R.B., Schardl C.L.;
RT   "On the sequence of bond formation in loline alkaloid biosynthesis.";
RL   ChemBioChem 7:1078-1088(2006).
RN   [4]
RP   FUNCTION.
RC   STRAIN=CBS 102646;
RX   PubMed=18655839; DOI=10.1016/j.fgb.2008.07.001;
RA   Spiering M.J., Faulkner J.R., Zhang D.X., Machado C., Grossman R.B.,
RA   Schardl C.L.;
RT   "Role of the LolP cytochrome P450 monooxygenase in loline alkaloid
RT   biosynthesis.";
RL   Fungal Genet. Biol. 45:1307-1314(2008).
RN   [5]
RP   FUNCTION, AND DISRUPTION PHENOTYPE.
RX   PubMed=24374065; DOI=10.1016/j.phytochem.2013.11.015;
RA   Pan J., Bhardwaj M., Faulkner J.R., Nagabhyru P., Charlton N.D.,
RA   Higashi R.M., Miller A.F., Young C.A., Grossman R.B., Schardl C.L.;
RT   "Ether bridge formation in loline alkaloid biosynthesis.";
RL   Phytochemistry 98:60-68(2014).
RN   [6]
RP   FUNCTION, AND BIOTECHNOLOGY.
RX   PubMed=25531527; DOI=10.1371/journal.pone.0115590;
RA   Pan J., Bhardwaj M., Nagabhyru P., Grossman R.B., Schardl C.L.;
RT   "Enzymes from fungal and plant origin required for chemical diversification
RT   of insecticidal loline alkaloids in grass-Epichloe symbiota.";
RL   PLoS ONE 9:E115590-E115590(2014).
RN   [7]
RP   FUNCTION, AND CATALYTIC ACTIVITY.
RX   PubMed=29537853; DOI=10.1021/acs.biochem.8b00157;
RA   Pan J., Bhardwaj M., Zhang B., Chang W.C., Schardl C.L., Krebs C.,
RA   Grossman R.B., Bollinger J.M. Jr.;
RT   "Installation of the ether bridge of lolines by the iron- and 2-
RT   oxoglutarate-dependent oxygenase, lolO: regio- and stereochemistry of
RT   sequential hydroxylation and oxacyclization reactions.";
RL   Biochemistry 57:2074-2083(2018).
CC   -!- FUNCTION: 2-oxoglutarate-dependent dioxygenase; part of the gene
CC       cluster that mediates the biosynthesis of loline alkaloids, potent
CC       insecticidal agents composed of a pyrrolizidine ring system and an
CC       uncommon ether bridge linking carbons 2 and 7 (PubMed:15654104).
CC       Lolines are structurally differentiated by the various modifications of
CC       the L-amino group and include norloline, loline, N-methylloline, N-
CC       acetylloline, N-acetylnorloline, and N-formylloline (PubMed:15861432,
CC       PubMed:25531527). The first committed step is the condensation of O-
CC       acetyl-L-homoserine (derived from L-aspartic acid) and L-proline,
CC       probably catalyzed by the gamma-type pyridoxal 5'-phosphate(PLP)-
CC       dependent enzyme lolC, to give the diamino diacid, NACPP
CC       (PubMed:15861432, PubMed:16755627). Ensuing cyclization,
CC       decarboxylation, and acetylation steps yield 1-exo-
CC       acetamidopyrrolizidine (AcAP)(PubMed:24374065). LolO is required for
CC       installation of the ether bridge upon the pathway intermediate, 1-exo-
CC       acetamidopyrrolizidine (AcAP) (PubMed:29537853). In sequential 2-
CC       oxoglutarate- and O(2)-consuming steps, lolO removes hydrogens from C2
CC       and C7 of AcAP to form both carbon-oxygen bonds in N-acetylnorloline
CC       (NANL), the precursor to all other lolines (PubMed:24374065,
CC       PubMed:29537853). The enzymes lolD, lolE, lolF and lolT have also been
CC       proposed to be involved in the ether-bridge installation
CC       (PubMed:15654104). Further processing of the exocyclic moiety of NANL
CC       by fungal N-acetamidase (LolN), methyltransferase (LolM), and
CC       cytochrome P450 (LolP) enzymes, with occasional involvement of a plant
CC       acetyltransferase, generates the other known lolines (PubMed:25531527,
CC       PubMed:18655839). LolN transforms NANL to norlonine which is
CC       monomethylated and dimethylated to respectively lonine and N-
CC       methyllonine (NML) by lolM (PubMed:25531527). LolP catalyzes
CC       hydroxylation of the methyl group in N-methylloline (NML) and further
CC       oxygenation to N-formylloline (NFL) (PubMed:18655839). A plant
CC       acetyltransferase is responsible for the acetylation of loline to form
CC       N-acetylloline (NAL) (PubMed:25531527). LolA might interact with
CC       aspartate kinase to prevent feedback inhibition of its activity by
CC       these end products and thereby promote production of L-homoserine from
CC       L-aspartate (PubMed:15654104). {ECO:0000269|PubMed:15654104,
CC       ECO:0000269|PubMed:15861432, ECO:0000269|PubMed:16755627,
CC       ECO:0000269|PubMed:18655839, ECO:0000269|PubMed:24374065,
CC       ECO:0000269|PubMed:25531527, ECO:0000269|PubMed:29537853}.
CC   -!- COFACTOR:
CC       Name=Fe(2+); Xref=ChEBI:CHEBI:29033;
CC         Evidence={ECO:0000255|PROSITE-ProRule:PRU00805};
CC       Note=Binds 1 Fe(2+) ion per subunit. {ECO:0000255|PROSITE-
CC       ProRule:PRU00805};
CC   -!- PATHWAY: Alkaloid biosynthesis. {ECO:0000305|PubMed:15654104}.
CC   -!- DISRUPTION PHENOTYPE: Leads to the accumulation of exo-1-
CC       acetamidopyrrolizidine but no lolines (PubMed:24374065).
CC       {ECO:0000269|PubMed:24374065}.
CC   -!- BIOTECHNOLOGY: Loline alkaloids show broad-spectrum anti-insect
CC       activity, and different lolines may have different biological
CC       activities (PubMed:25531527). In vitro tests of NFL, NAL, NML, and
CC       semisynthetic loline derivatives with long carbon-chain acylations on
CC       the 1-amine have shown that many are effective against both fall
CC       armyworm larvae and European corn borer larvae, but the effects seem to
CC       differ depending on the modifications (PubMed:25531527). N-Formylloline
CC       reduces the weight gain of fall armyworms by deterring feeding, and
CC       does not significantly affect corn borers (PubMed:25531527). In
CC       contrast, NAL reduces the weight gain of corn borer larvae without
CC       changing larval feeding behavior, indicating that its effect is due to
CC       metabolic toxicity. N-formylloline, NAL, and NML are almost as potent
CC       as nicotine in insecticidal activity against green bugs
CC       (PubMed:25531527). {ECO:0000305|PubMed:25531527}.
CC   -!- SIMILARITY: Belongs to the iron/ascorbate-dependent oxidoreductase
CC       family. {ECO:0000305}.
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DR   EMBL; AY723750; AAV68697.1; -; Genomic_DNA.
DR   AlphaFoldDB; Q5MNH6; -.
DR   SMR; Q5MNH6; -.
DR   GO; GO:0051213; F:dioxygenase activity; IEA:UniProtKB-KW.
DR   GO; GO:0046872; F:metal ion binding; IEA:UniProtKB-KW.
DR   GO; GO:0009820; P:alkaloid metabolic process; IEA:UniProtKB-KW.
DR   Gene3D; 2.60.120.330; -; 1.
DR   InterPro; IPR026992; DIOX_N.
DR   InterPro; IPR044861; IPNS-like_FE2OG_OXY.
DR   InterPro; IPR027443; IPNS-like_sf.
DR   InterPro; IPR005123; Oxoglu/Fe-dep_dioxygenase.
DR   Pfam; PF03171; 2OG-FeII_Oxy; 1.
DR   Pfam; PF14226; DIOX_N; 1.
DR   PROSITE; PS51471; FE2OG_OXY; 1.
PE   1: Evidence at protein level;
KW   Alkaloid metabolism; Dioxygenase; Iron; Metal-binding; Oxidoreductase.
FT   CHAIN           1..362
FT                   /note="2-oxoglutarate-dependent dioxygenase lolO2"
FT                   /id="PRO_0000444362"
FT   DOMAIN          199..312
FT                   /note="Fe2OG dioxygenase"
FT                   /evidence="ECO:0000255|PROSITE-ProRule:PRU00805"
FT   BINDING         222
FT                   /ligand="Fe cation"
FT                   /ligand_id="ChEBI:CHEBI:24875"
FT                   /evidence="ECO:0000255|PROSITE-ProRule:PRU00805"
FT   BINDING         224
FT                   /ligand="Fe cation"
FT                   /ligand_id="ChEBI:CHEBI:24875"
FT                   /evidence="ECO:0000255|PROSITE-ProRule:PRU00805"
FT   BINDING         280
FT                   /ligand="Fe cation"
FT                   /ligand_id="ChEBI:CHEBI:24875"
FT                   /evidence="ECO:0000255|PROSITE-ProRule:PRU00805"
FT   BINDING         303
FT                   /ligand="2-oxoglutarate"
FT                   /ligand_id="ChEBI:CHEBI:16810"
FT                   /evidence="ECO:0000255|PROSITE-ProRule:PRU00805"
SQ   SEQUENCE   362 AA;  41269 MW;  04AE67E12FBEBE59 CRC64;
     MTVTNKPVEP ANVPVMDFEA IHASVGNERK EYLRQLDEAW SHHGAVYVIN HSIGTETLEE
     AFVWCKKFFD LPLAVKNSVH IPPDVSKHFQ GWTGTGEAIS SQGVWDPDEI ERLRKEMPTE
     LKEAMELQDP CGTYPPGNPD LNLVEQHLPG YLDFLKKWFA ACYKQSLQNM RLVCEILGME
     DLDYIGKKFE PRHMSTHSTW NYFLGQPVSQ LASGSSNRLN AHTDYCQFTM LFQDMVGGLE
     LHDYEEDIYR PVPPIKGAMI VQVGDLLEKQ TNGRWRSALH RVTAPSRYMY GGSPGGDDEL
     VQRYSLVFFG HLNLDEMIKP LPGCEKPGKW STLEWKDLMT AGQWLARRVA LEYERKTAAT
     VM
 
 
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