GTPS_ORIVU
ID GTPS_ORIVU Reviewed; 594 AA.
AC E2E2P0; E2E2N9;
DT 05-SEP-2012, integrated into UniProtKB/Swiss-Prot.
DT 30-NOV-2010, sequence version 1.
DT 03-AUG-2022, entry version 33.
DE RecName: Full=Gamma-terpinene synthase, chloroplastic {ECO:0000303|PubMed:20419468};
DE EC=4.2.3.114 {ECO:0000269|PubMed:20419468, ECO:0000269|Ref.2};
DE AltName: Full=Alpha-terpinene synthase {ECO:0000303|PubMed:20419468};
DE EC=4.2.3.115 {ECO:0000269|PubMed:20419468, ECO:0000269|Ref.2};
DE AltName: Full=Terpene synthase 2 {ECO:0000303|PubMed:20419468};
DE Short=OvTPS2 {ECO:0000303|PubMed:20419468};
DE Flags: Precursor;
GN Name=TPS2 {ECO:0000303|PubMed:20419468};
OS Origanum vulgare (Wild marjoram).
OC Eukaryota; Viridiplantae; Streptophyta; Embryophyta; Tracheophyta;
OC Spermatophyta; Magnoliopsida; eudicotyledons; Gunneridae; Pentapetalae;
OC asterids; lamiids; Lamiales; Lamiaceae; Nepetoideae; Mentheae; Origanum.
OX NCBI_TaxID=39352;
RN [1]
RP NUCLEOTIDE SEQUENCE [MRNA], FUNCTION, CATALYTIC ACTIVITY,
RP BIOPHYSICOCHEMICAL PROPERTIES, COFACTOR, TISSUE SPECIFICITY, AND PATHWAY.
RC STRAIN=cv. d06-01, and cv. f02-04; TISSUE=Trichome gland;
RX PubMed=20419468; DOI=10.1007/s11103-010-9636-1;
RA Crocoll C., Asbach J., Novak J., Gershenzon J., Degenhardt J.;
RT "Terpene synthases of oregano (Origanum vulgare L.) and their roles in the
RT pathway and regulation of terpene biosynthesis.";
RL Plant Mol. Biol. 73:587-603(2010).
RN [2]
RP FUNCTION, CATALYTIC ACTIVITY, BIOPHYSICOCHEMICAL PROPERTIES, COFACTOR, AND
RP PATHWAY.
RA Crocoll C.;
RT "Biosynthesis of the phenolic monoterpenes, thymol and carvacrol, by
RT terpene synthases and cytochrome P450s in oregano and thyme.";
RL Thesis (2011), Friedrich Schiller University of Jena, Germany.
RN [3]
RP REVIEW ON CARVACROL, AND BIOTECHNOLOGY.
RX PubMed=24915411; DOI=10.1080/10408398.2011.653458;
RA Suntres Z.E., Coccimiglio J., Alipour M.;
RT "The bioactivity and toxicological actions of carvacrol.";
RL Crit. Rev. Food Sci. Nutr. 55:304-318(2015).
RN [4]
RP FUNCTION, AND INDUCTION BY MYRMICA ANTS.
RX PubMed=26156773; DOI=10.1098/rspb.2015.1111;
RA Patricelli D., Barbero F., Occhipinti A., Bertea C.M., Bonelli S.,
RA Casacci L.P., Zebelo S.A., Crocoll C., Gershenzon J., Maffei M.E.,
RA Thomas J.A., Balletto E.;
RT "Plant defences against ants provide a pathway to social parasitism in
RT butterflies.";
RL Proc. R. Soc. B 282:0-0(2015).
RN [5]
RP INDUCTION BY DROUGHT.
RX PubMed=27915173; DOI=10.1016/j.plaphy.2016.11.023;
RA Morshedloo M.R., Craker L.E., Salami A., Nazeri V., Sang H., Maggi F.;
RT "Effect of prolonged water stress on essential oil content, compositions
RT and gene expression patterns of mono- and sesquiterpene synthesis in two
RT oregano (Origanum vulgare L.) subspecies.";
RL Plant Physiol. Biochem. 111:119-128(2017).
RN [6]
RP FUNCTION, AND INDUCTION BY SPODOPTERA LITTORALIS.
RX PubMed=30231481; DOI=10.3390/ijms19092805;
RA Agliassa C., Maffei M.E.;
RT "Origanum vulgare Terpenoids Induce Oxidative stress and reduce the feeding
RT activity of Spodoptera littoralis.";
RL Int. J. Mol. Sci. 19:0-0(2018).
RN [7]
RP REVIEW ON THYMOL, AND BIOTECHNOLOGY.
RX PubMed=29785774; DOI=10.1002/ptr.6109;
RA Salehi B., Mishra A.P., Shukla I., Sharifi-Rad M., Contreras M.D.M.,
RA Segura-Carretero A., Fathi H., Nasrabadi N.N., Kobarfard F.,
RA Sharifi-Rad J.;
RT "Thymol, thyme, and other plant sources: Health and potential uses.";
RL Phytother. Res. 32:1688-1706(2018).
RN [8]
RP REVIEW ON CARVACROL AND THYMOL, AND BIOTECHNOLOGY.
RX PubMed=29874939; DOI=10.1080/14786419.2018.1480618;
RA Wang K., Jiang S., Yang Y., Fan L., Su F., Ye M.;
RT "Synthesis and antifungal activity of carvacrol and thymol esters with
RT heteroaromatic carboxylic acids.";
RL Nat. Prod. Res. 33:1924-1930(2019).
RN [9]
RP REVIEW ON CARVACROL EFFECTS ON COVID-19, AND BIOTECHNOLOGY.
RX PubMed=33664752; DOI=10.3389/fpls.2020.601335;
RA Javed H., Meeran M.F.N., Jha N.K., Ojha S.;
RT "Carvacrol, a plant metabolite targeting viral protease (Mpro) and ACE2 in
RT host cells can be a possible candidate for COVID-19.";
RL Front. Plant Sci. 11:601335-601335(2020).
RN [10]
RP REVIEW ON CARVACROL EFFECTS ON COVID-19, AND BIOTECHNOLOGY.
RX PubMed=32448034; DOI=10.1080/07391102.2020.1772112;
RA Kumar A., Choudhir G., Shukla S.K., Sharma M., Tyagi P., Bhushan A.,
RA Rathore M.;
RT "Identification of phytochemical inhibitors against main protease of COVID-
RT 19 using molecular modeling approaches.";
RL J. Biomol. Struct. Dyn. 4:1-11(2020).
RN [11]
RP REVIEW ON CARVACROL DERIVATIVES, AND BIOTECHNOLOGY.
RX PubMed=30836858; DOI=10.1080/07391102.2019.1590243;
RA Zengin Kurt B., Durdagi S., Celebi G., Ekhteiari Salmas R., Sonmez F.;
RT "Synthesis, anticholinesterase activity and molecular modeling studies of
RT novel carvacrol-substituted amide derivatives.";
RL J. Biomol. Struct. Dyn. 38:841-859(2020).
RN [12]
RP REVIEW ON PLANT ESSENTIAL OILS EFFECTS ON COVID-19, AND BIOTECHNOLOGY.
RX PubMed=32834111; DOI=10.1016/j.molstruc.2020.128823;
RA Kulkarni S.A., Nagarajan S.K., Ramesh V., Palaniyandi V., Selvam S.P.,
RA Madhavan T.;
RT "Computational evaluation of major components from plant essential oils as
RT potent inhibitors of SARS-CoV-2 spike protein.";
RL J. Mol. Struct. 1221:128823-128823(2020).
RN [13]
RP REVIEW ON PLANT ESSENTIAL OILS EFFECTS ON COVID-19, AND BIOTECHNOLOGY.
RX PubMed=33855010; DOI=10.3389/fchem.2021.642026;
RA Yadalam P.K., Varatharajan K., Rajapandian K., Chopra P., Arumuganainar D.,
RA Nagarathnam T., Sohn H., Madhavan T.;
RT "Antiviral essential oil components against SARS-CoV-2 in pre-procedural
RT mouth rinses for dental settings during COVID-19: A computational study.";
RL Front. Chem. 9:642026-642026(2021).
CC -!- FUNCTION: Involved in the biosynthesis of phenolic monoterpenes natural
CC products thymol and carvacrol which have a broad range of biological
CC activities acting as antimicrobial compounds, insecticides,
CC antioxidants and pharmaceutical agents (PubMed:20419468, Ref.2,
CC PubMed:30231481, PubMed:26156773). Monoterpene synthase which catalyzes
CC the conversion of geranyl diphosphate (GPP) to gamma-terpinene and the
CC minor products alpha-thujene, alpha-terpinene, myrcene, sabinene, (+)-
CC R-limonene, alpha-pinene and alpha-phellandrene (PubMed:20419468,
CC Ref.2). {ECO:0000269|PubMed:20419468, ECO:0000269|PubMed:26156773,
CC ECO:0000269|PubMed:30231481, ECO:0000269|Ref.2}.
CC -!- CATALYTIC ACTIVITY:
CC Reaction=(2E)-geranyl diphosphate = diphosphate + gamma-terpinene;
CC Xref=Rhea:RHEA:32559, ChEBI:CHEBI:10577, ChEBI:CHEBI:33019,
CC ChEBI:CHEBI:58057; EC=4.2.3.114;
CC Evidence={ECO:0000269|PubMed:20419468, ECO:0000269|Ref.2};
CC PhysiologicalDirection=left-to-right; Xref=Rhea:RHEA:32560;
CC Evidence={ECO:0000269|PubMed:20419468, ECO:0000269|Ref.2};
CC -!- CATALYTIC ACTIVITY:
CC Reaction=(2E)-geranyl diphosphate = alpha-terpinene + diphosphate;
CC Xref=Rhea:RHEA:32563, ChEBI:CHEBI:10334, ChEBI:CHEBI:33019,
CC ChEBI:CHEBI:58057; EC=4.2.3.115;
CC Evidence={ECO:0000269|PubMed:20419468, ECO:0000269|Ref.2};
CC PhysiologicalDirection=left-to-right; Xref=Rhea:RHEA:32564;
CC Evidence={ECO:0000269|PubMed:20419468, ECO:0000269|Ref.2};
CC -!- COFACTOR:
CC Name=Mn(2+); Xref=ChEBI:CHEBI:29035;
CC Evidence={ECO:0000269|PubMed:20419468, ECO:0000269|Ref.2};
CC Name=Mg(2+); Xref=ChEBI:CHEBI:18420;
CC Evidence={ECO:0000269|PubMed:20419468, ECO:0000269|Ref.2};
CC Note=Manganese > magnesium. {ECO:0000269|PubMed:20419468,
CC ECO:0000269|Ref.2};
CC -!- BIOPHYSICOCHEMICAL PROPERTIES:
CC Kinetic parameters:
CC KM=8.71 uM for geranyl diphosphate (in the presence of 0.5 mM
CC manganese) {ECO:0000269|PubMed:20419468, ECO:0000269|Ref.2};
CC KM=0.70 mM for manganese (in the presence of 10 uM geranyl
CC diphosphate) {ECO:0000269|PubMed:20419468, ECO:0000269|Ref.2};
CC KM=3.41 mM for magnesium (in the presence of 10 uM geranyl
CC diphosphate) {ECO:0000269|PubMed:20419468, ECO:0000269|Ref.2};
CC Vmax=6.18 umol/min/g enzyme with geranyl diphosphate as substrate
CC {ECO:0000269|PubMed:20419468, ECO:0000269|Ref.2};
CC pH dependence:
CC Optimum pH is 6.8. {ECO:0000269|PubMed:20419468, ECO:0000269|Ref.2};
CC Temperature dependence:
CC Optimum temperature is 28 degrees Celsius.
CC {ECO:0000269|PubMed:20419468, ECO:0000269|Ref.2};
CC -!- PATHWAY: Secondary metabolite biosynthesis; terpenoid biosynthesis.
CC {ECO:0000269|PubMed:20419468, ECO:0000269|Ref.2}.
CC -!- SUBUNIT: Homodimer. {ECO:0000250|UniProtKB:A0A0M3Q1Q3}.
CC -!- SUBCELLULAR LOCATION: Plastid, chloroplast {ECO:0000305}.
CC -!- TISSUE SPECIFICITY: Expressed in peltate glandular trichomes.
CC {ECO:0000269|PubMed:20419468}.
CC -!- INDUCTION: Induced by drought (PubMed:27915173). Accumulates upon root
CC colonization by Myrmica ants (Myrmica sabuleti and Myrmica scabrinodis)
CC concomitantly with jasmonates induction; this leads to the production
CC of carvacrol, an attractant for the phytophagous-predaceous butterfly
CC Maculinea arion, whose larvae initially feed on Origanum vulgare
CC flowerheads before switching to parasitize Myrmica ant colonies for
CC their main period of growth (PubMed:26156773). Slightly induced by
CC Spodoptera littoralis, an herbivory insect, thus triggering the
CC production of carvacrol, which exhibits insecticide properties
CC (PubMed:30231481). {ECO:0000269|PubMed:26156773,
CC ECO:0000269|PubMed:27915173, ECO:0000269|PubMed:30231481}.
CC -!- DOMAIN: The Asp-Asp-Xaa-Xaa-Asp/Glu (DDXXD/E) motif is important for
CC the catalytic activity, presumably through binding to Mg(2+).
CC {ECO:0000250|UniProtKB:Q9X839}.
CC -!- BIOTECHNOLOGY: The monoterpenic phenol carvacrol is commonly used as a
CC fragrance and a food flavoring ingredient and preservative
CC (PubMed:24915411). Its derivatives exhibit also various biological and
CC pharmacological properties including antioxidant, antibacterial,
CC antifungal, insecticid, nematicid, anticancer, anti-inflammatory,
CC hepatoprotective, spasmolytic, and vasorelaxant (PubMed:24915411,
CC PubMed:29874939, PubMed:30836858, PubMed:33664752). Phytochemical
CC inhibitor targeting the main SARS-CoV-2 viral protease (Mpro) and ACE2
CC in human host cells, carvacrol is a possible candidate for treating
CC COVID-19 (PubMed:33664752, PubMed:32448034). Carvacrol may also have
CC antiviral activity toward COVID-19 by binding to the S1 receptor
CC binding domain of the SARS-CoV-2 spike (S) glycoprotein
CC (PubMed:32834111, PubMed:33855010). {ECO:0000303|PubMed:24915411,
CC ECO:0000303|PubMed:29874939, ECO:0000303|PubMed:30836858,
CC ECO:0000303|PubMed:32448034, ECO:0000303|PubMed:32834111,
CC ECO:0000303|PubMed:33664752, ECO:0000303|PubMed:33855010}.
CC -!- BIOTECHNOLOGY: The monoterpenic phenol thymol is widely used as a
CC fragrance and a flavoring ingredient in food and cosmetic industries
CC (PubMed:29785774). Its derivatives have also several biological and
CC pharmacological properties such as antimicrobial, antioxidant,
CC anticarcinogenesis, anti-inflammatory and antispasmodic activities
CC (PubMed:29785774, PubMed:29874939). Medical applications include the
CC treatment of disorders affecting the respiratory, nervous, and
CC cardiovascular systems (PubMed:29785774). It may also act as a growth
CC enhancer and immunomodulator (PubMed:29785774). Thymol may also have
CC antiviral activity toward COVID-19 by binding to the S1 receptor
CC binding domain of the SARS-CoV-2 spike (S) glycoprotein
CC (PubMed:32834111, PubMed:33855010). {ECO:0000303|PubMed:29785774,
CC ECO:0000303|PubMed:29874939, ECO:0000303|PubMed:32834111,
CC ECO:0000303|PubMed:33855010}.
CC -!- SIMILARITY: Belongs to the terpene synthase family. {ECO:0000305}.
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DR EMBL; GU385977; ADK73620.1; -; mRNA.
DR EMBL; GU385978; ADK73621.1; -; mRNA.
DR AlphaFoldDB; E2E2P0; -.
DR SMR; E2E2P0; -.
DR PRIDE; E2E2P0; -.
DR BRENDA; 4.2.3.114; 12977.
DR UniPathway; UPA00213; -.
DR GO; GO:0009507; C:chloroplast; IEA:UniProtKB-SubCell.
DR GO; GO:0102903; F:gamma-terpinene synthase activity; IEA:UniProtKB-EC.
DR GO; GO:0000287; F:magnesium ion binding; IDA:UniProtKB.
DR GO; GO:0042803; F:protein homodimerization activity; ISS:UniProtKB.
DR GO; GO:0010333; F:terpene synthase activity; IDA:UniProtKB.
DR GO; GO:0002213; P:defense response to insect; IEP:UniProtKB.
DR GO; GO:0016102; P:diterpenoid biosynthetic process; IEA:InterPro.
DR GO; GO:0033383; P:geranyl diphosphate metabolic process; IDA:UniProtKB.
DR GO; GO:0009625; P:response to insect; IEP:UniProtKB.
DR GO; GO:0009414; P:response to water deprivation; IEP:UniProtKB.
DR CDD; cd00684; Terpene_cyclase_plant_C1; 1.
DR Gene3D; 1.10.600.10; -; 1.
DR Gene3D; 1.50.10.130; -; 1.
DR InterPro; IPR008949; Isoprenoid_synthase_dom_sf.
DR InterPro; IPR034741; Terpene_cyclase-like_1_C.
DR InterPro; IPR044814; Terpene_cyclase_plant_C1.
DR InterPro; IPR001906; Terpene_synth_N.
DR InterPro; IPR036965; Terpene_synth_N_sf.
DR InterPro; IPR005630; Terpene_synthase_metal-bd.
DR InterPro; IPR008930; Terpenoid_cyclase/PrenylTrfase.
DR Pfam; PF01397; Terpene_synth; 1.
DR Pfam; PF03936; Terpene_synth_C; 1.
DR SFLD; SFLDG01019; Terpene_Cyclase_Like_1_C_Termi; 1.
DR SUPFAM; SSF48239; SSF48239; 1.
DR SUPFAM; SSF48576; SSF48576; 1.
PE 1: Evidence at protein level;
KW Chloroplast; Lyase; Magnesium; Manganese; Metal-binding; Plastid;
KW Transit peptide.
FT TRANSIT 1..44
FT /note="Chloroplast"
FT /evidence="ECO:0000255"
FT CHAIN 45..594
FT /note="Gamma-terpinene synthase, chloroplastic"
FT /id="PRO_0000418651"
FT REGION 353..359
FT /note="Homodimerization"
FT /evidence="ECO:0000250|UniProtKB:A0A0M3Q1Q3"
FT REGION 425..462
FT /note="Homodimerization"
FT /evidence="ECO:0000250|UniProtKB:A0A0M3Q1Q3"
FT MOTIF 347..351
FT /note="DDXXD motif"
FT /evidence="ECO:0000250|UniProtKB:Q9X839"
FT BINDING 347
FT /ligand="Mn(2+)"
FT /ligand_id="ChEBI:CHEBI:29035"
FT /ligand_label="1"
FT /evidence="ECO:0000250|UniProtKB:A0A1C9J6A7"
FT BINDING 347
FT /ligand="Mn(2+)"
FT /ligand_id="ChEBI:CHEBI:29035"
FT /ligand_label="2"
FT /evidence="ECO:0000250|UniProtKB:A0A1C9J6A7"
FT BINDING 351
FT /ligand="Mn(2+)"
FT /ligand_id="ChEBI:CHEBI:29035"
FT /ligand_label="1"
FT /evidence="ECO:0000250|UniProtKB:A0A1C9J6A7"
FT BINDING 351
FT /ligand="Mn(2+)"
FT /ligand_id="ChEBI:CHEBI:29035"
FT /ligand_label="2"
FT /evidence="ECO:0000250|UniProtKB:A0A1C9J6A7"
FT BINDING 491
FT /ligand="Mn(2+)"
FT /ligand_id="ChEBI:CHEBI:29035"
FT /ligand_label="3"
FT /evidence="ECO:0000250|UniProtKB:A0A1C9J6A7"
FT BINDING 499
FT /ligand="Mn(2+)"
FT /ligand_id="ChEBI:CHEBI:29035"
FT /ligand_label="3"
FT /evidence="ECO:0000250|UniProtKB:A0A1C9J6A7"
FT VARIANT 103
FT /note="A -> V (in strain: cv. f02-04)"
FT /evidence="ECO:0000269|PubMed:20419468"
FT VARIANT 137
FT /note="H -> R (in strain: cv. f02-04)"
FT /evidence="ECO:0000269|PubMed:20419468"
FT VARIANT 171..177
FT /note="DFFKNED -> NFFKTEN (in strain: cv. f02-04)"
FT /evidence="ECO:0000269|PubMed:20419468"
FT VARIANT 262
FT /note="R -> K (in strain: cv. f02-04)"
FT /evidence="ECO:0000269|PubMed:20419468"
FT VARIANT 268
FT /note="I -> V (in strain: cv. f02-04)"
FT /evidence="ECO:0000269|PubMed:20419468"
FT VARIANT 450
FT /note="S -> P (in strain: cv. f02-04)"
FT /evidence="ECO:0000269|PubMed:20419468"
SQ SEQUENCE 594 AA; 69063 MW; D58A81E909E2FC6E CRC64;
MATLSMQVSI LSKEVKNVNN IGMRASKPMV ARRVSTTRLR PICSASLQVE EETRRSGNYQ
ASIWNNDYVQ SFNTNQYKDE KHLKKKEELI AQVKILLNTK MEAVKQLELI EDLRNLGLTY
YFQDEVKKIL TSIYNDHKCF KNEQVGDLYF TSLGFRLLRL HGFDVSEEVF DFFKNEDGSD
FKASLGENIK DVLQLYEASF LIREGEVILE QARVFSTKHL EKKVDEGIND EKLLAWIRHS
LALPLHWRIQ RLEARWFLDA YRARKDMIPL IFELGKIDFH IIQETQLEEL QEVSKWWTNS
NLAEKLPFVR DRIVECYFWA LGLFEPHEYG YQRKMAAIII TFVTIIDDVY DVYGTLDELQ
LFTDAIRKWD FQSISTLPYY MQVCYLALYT YASELAYDIL KDQGFNSIAY LQRSWLSLVE
GFFQEAKWYY AGYTPTLAEY LENAKVSISS PTIISQVYFT LPNSTERTVV ENVFGYHNIL
YLSGMILRLA DDLGTTQFEL KRGDVQKAIQ CYMKDNNATE KEGAEHVKYL LREAWKEMNT
AMADPECPLS EDLVDAAANL GRASQFIYLE GDGHGVQHSE IHNQMGGLIF EPYV
