Category:TP5

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=={{Bilingual|生合成|Biosynthesis}}==
 
=={{Bilingual|生合成|Biosynthesis}}==
 
==={{Bilingual|概要|Overview}}===
 
==={{Bilingual|概要|Overview}}===
 +
Two major classes of terpene synthases exist: "transoid" and "cisoid" synthase.
 +
Transoid synthase directly ionizes ('trans','trans')-farnesyl diphosphate, whereas
 +
Cisoid synthase first isomerizes C2-C3 double bond to produce the neutral (3'R')- or (3'S')-nerolidyl diphosphate (enzyme-bound) and then ionizes it.
 +
 +
{| class="wikitable" style="text-align:right"
 +
! Substrate || Type || Intermediate
 +
|-
 +
| rowspan="2"| Farnesyl diphosphate (FPP)<br/>[[Image:Farnesyl_diphosphate.png]]
 +
| Transoid synthase on (2-''trans'',6-''trans'')-FPP<br/>
 +
| [[Image:Farnesyl_cation.png]]
 +
|-
 +
| Cisoid synthase on (2-''cis'',6-''trans'')-FPP<br/>
 +
| (nerolidyl cation)<br/>[[Image:Nerolidyl_cation.png]]
 +
|}
  
  
Line 44: Line 58:
 
<!---FARNESYL--->
 
<!---FARNESYL--->
 
|-
 
|-
−
|rowspan="7" align="center"| farnesyl cation<br/>[[Image:Farnesyl cation.png|100px]]
+
|rowspan="7" align="center" valign="top"| farnesyl cation<br/>[[Image:Farnesyl cation.png|100px]]
 
|colspan="2"|
 
|colspan="2"|
 
{|
 
{|
 
| farnesane, acyclic ones
 
| farnesane, acyclic ones
 
| cyclobutane, cyclopentane
 
| cyclobutane, cyclopentane
−
| cyclofarnesane
+
| cyclofarnesan
 
|}
 
|}
 
|-
 
|-
−
|rowspan="3"|(E,E)-germacradiene<br/>[[Image:(E,E)-Germacradienyl cation.png|100px]]
+
|rowspan="3" valign="top"|(E,E)-germacradiene<br/>[[Image:(E,E)-Germacradienyl cation.png]]
 +
<hr style="border:dashed"/>
 
* germacrane<br/>[[Image:Germacrene A.png|90px]]
 
* germacrane<br/>[[Image:Germacrene A.png|90px]]
 
* lepidozane<br/>[[Image:Lepidozane.png|90px]]
 
* lepidozane<br/>[[Image:Lepidozane.png|90px]]
 
* bicyclogermacrane<br/>[[Image:Bicyclogermacrane.png|90px]]
 
* bicyclogermacrane<br/>[[Image:Bicyclogermacrane.png|90px]]
−
| eudesmane (= selinane)<br/>[[Image:Eudesmanyl cation.png|100px]]<!---[[Image:beta-Selinene.png|80px]]-->
+
| eudesmane (= selinane)<br/>[[Image:Eudesmanyl cation.png]]<!---[[Image:beta-Selinene.png|80px]]-->
−
* cycloeudesmane
+
<hr style="border:dashed"/>
−
* elemane ... 7,8 seco form
+
* cycloeudesmane<br/>[[Image:Cycloeudesmane.png|85px]]
−
* emmotin ... 14(10&rarr;1) abeo form
+
* elemane ... 7,8 seco form<br/>[[Image:Elemene.png|85px]]
−
* farfugin ... 14(10&rarr;9) abeo form
+
* emmotin ... 14(10&rarr;1) abeo form<br/>[[Image:Emmotin.png|85px]]
−
* gorgonane 11(7&rarr;6) abeo form
+
* farfugin ... 14(10&rarr;9) abeo form<br/>[[Image:Farfugin.png|85px]]
−
* oppositane ... 8(7&rarr;6) abeo form
+
* gorgonane 11(7&rarr;6) abeo form<br/>[[Image:Gorgonane.png|70px]]
−
* valerane (= jatamansane) 15(4&rarr;5) abeo form
+
* oppositane ... 8(7&rarr;6) abeo form<br/>[[Image:Oppositane.png|85px]]
−
| vetispiradienyl cation<br/>[[Image:Vetispiradienyl_cation.png|90px]]
+
* valerane (= jatamansane) 15(4&rarr;5) abeo form<br/>[[Image:Valerane.png|85px]]
 +
|valign="top"|vetispiradienyl cation<br/>[[Image:Vetispiradienyl_cation.png|90px]]
 +
<hr style="border:dashed"/>
 
* vetispiradiene<br/>[[Image:Vetispiradiene.png|80px]]
 
* vetispiradiene<br/>[[Image:Vetispiradiene.png|80px]]
 
* spirovetivane (= vetispirane)<br/>[[Image:Spirovetivane.png|80px]]
 
* spirovetivane (= vetispirane)<br/>[[Image:Spirovetivane.png|80px]]
 
|-
 
|-
 
| eremophilane (= 14(10&rarr;5) abeoeudesmane)<br/>[[Image:Eremophilenyl cation.png|100px]]
 
| eremophilane (= 14(10&rarr;5) abeoeudesmane)<br/>[[Image:Eremophilenyl cation.png|100px]]
−
 
+
* aristolochene<br/>[[Image:5-epi-Aristolochene.png|85px]]
−
* aristolane ... 6,11-cyclo form<br/>[[Image:5-epi-Aristolochene.png|80px]]
+
* aristolane ... 6,11-cyclo form<br/>[[Image:Aristolane.png|80px]]
−
* chiloscyphane ...8(7&rarr;6) abeo form
+
* chiloscyphane ...8(7&rarr;6) abeo form<br/>[[Image:Chiloscyphane.png|80px]]
−
* nardosinane ... 11(7&rarr;6) abeo form
+
* nardosinane ... 11(7&rarr;6) abeo form<br/>[[Image:Nardosinane.png|70px]]
−
* brasilane?
+
* cacalol ... 14(5&rarr;6) abeo form<br/>[[Image:Cacalol.png|85px]]
−
* cacalol ... 14(5&rarr;6) abeo form
+
* fukinane ... 9(8&rarr;7) abeo form<br/>[[Image:Fukinane.png|85px]] [[Petasites japonicus]]
−
* fukinane ... 9(8&rarr;7) abeo form<br/>[[Petasites japonicus]]
+
* brasilane<br/>[[Image:Brasilane.png|75px]]
−
* ishwarane?
+
* thapsane<br/>[[Image:Thapsane.png|85px]]
 +
* ishwarane<br/>[[Image:Ishwarane.png|60px]]
 
|-
 
|-
−
| [http://www.orc.wur.nl/UK/Research/Bio-catalyzed+and+bio-based+synthesis+(dr.+M.C.R.+Franssen)/Sesquiterpene+biosynthesis guaiane]
+
| [http://www.orc.wur.nl/UK/Research/Bio-catalyzed+and+bio-based+synthesis+(dr.+M.C.R.+Franssen)/Sesquiterpene+biosynthesis guaiane]<br/>[[Image:Guaiane.png|85px]]
−
* xanthane, carabrane ... 4,5 seco form
+
* xanthane ... 4,5 seco form<br/>[[Image:Xanthane.png|70px]]
−
* pseudoguaiane ... 15(4&rarr;5) abeo form
+
* carabrane ... 4,5 seco form<br/>[[Image:Carabrane.png|70px]]
−
* valerenane ... 8(7&rarr;6) abeo form
+
* pseudoguaiane ... 15(4&rarr;5) abeo form<br/>[[Image:Pseudoguaiane.png|70px]]
 +
* valerenane ... 8(7&rarr;6) abeo form<br/>[[Image:Valerenane.png|75px]]
 
|
 
|
−
Cycloguaiane
+
cycloguaiane
 
* cubebane ...  1,6-cyclo form<br/>[[Image:Cubebane.png|80px]]
 
* cubebane ...  1,6-cyclo form<br/>[[Image:Cubebane.png|80px]]
 
* ivaxillarane ... 8,10-cyclo form<br/>[[Image:Ivaxillarane.png|80px]]
 
* ivaxillarane ... 8,10-cyclo form<br/>[[Image:Ivaxillarane.png|80px]]
Line 93: Line 112:
 
|rowspan="2"| (E,E)-humulane<br/>[[Image:(E,E)-Humulyl cation.png|100px]]
 
|rowspan="2"| (E,E)-humulane<br/>[[Image:(E,E)-Humulyl cation.png|100px]]
 
* bicyclohumulane<br/>[[Image:Bicyclohumulane.png|80px]]
 
* bicyclohumulane<br/>[[Image:Bicyclohumulane.png|80px]]
−
| [http://stoltz.caltech.edu/seminars/2009_Henry.pdf africanane]<br/>[[Image:Africanane.png|90px]]
 
−
|-
 
 
| caryophyllane<br/>[[Image:(E)-beta-Caryophyllene.png|80px]]
 
| caryophyllane<br/>[[Image:(E)-beta-Caryophyllene.png|80px]]
 +
|-
 +
| [http://stoltz.caltech.edu/seminars/2009_Henry.pdf africanane]<br/>[[Image:Africanane.png|80px]]
 
|-
 
|-
 
| [http://www.sciencedirect.com/science/article/pii/S0040402099002562 drimane]<br/>[[Image:Drimane.png|100px]]
 
| [http://www.sciencedirect.com/science/article/pii/S0040402099002562 drimane]<br/>[[Image:Drimane.png|100px]]
Line 106: Line 125:
 
|rowspan="2"| bisabolane<br/>[[Image:Bisabolyl cation.png|100px]]
 
|rowspan="2"| bisabolane<br/>[[Image:Bisabolyl cation.png|100px]]
 
* thujopsane<br/>[[Image:(-)-Sesquithujene.png|80px]]
 
* thujopsane<br/>[[Image:(-)-Sesquithujene.png|80px]]
−
| chamigrane ... 6,11-cyclobisabolane<br/>[[Image:Chamigrane|80px]]
+
| chamigrane ... 6,11-cyclobisabolane<br/>[[Image:Chamigrane.png|90px]]
−
* acorane ... 6,10-cyclobisabolane<br/>[[Image:Acorane|60px]]
+
* acorane ... 6,10-cyclobisabolane<br/>[[Image:Acorane.png|80px]]
−
* secochamigrane<br/>[[Image:Secochamigrane|60px]]
+
 
|-
 
|-
−
| cuparane (= 7,11-cyclobisabolane)
+
| cuparane (= 7,11-cyclobisabolane)<br/>[[Image:Cuparane.png|95px]]
−
* herbertane [[liverwort,fungi]] ... 15(3&rarr;4) abeo form
+
* herbertane [[liverwort,fungi]] ... 15(3&rarr;4) abeo form<br/>[[Image:Herbertane.png|80px]]
−
* laurane [[Laurencia spp. (marine)]] ... 13(11&rarr;10) abeo form
+
* laurane [[Laurencia spp. (marine)]] ... 13(11&rarr;10) abeo form<br/>[[Image:Laurane.png|90px]]
−
| trichothecane <ref>Grove JF "Non-Macrocyclic Trichothecenes" Nat Prod Rep 5:187-209, 1988</ref>
+
* cyclolaurane <br/>[[Image:Cyclolaurane.png|85px]]
 +
| trichothecane <ref>Grove JF "Non-Macrocyclic Trichothecenes" Nat Prod Rep 5:187-209, 1988</ref><br/>[[Image:Trichothecane.png|50px]]
 +
* gymnomitrane<br/>[[Image:Gymnomitrane.png|70px]]
 
{|
 
{|
−
| gymnomitrane
+
| widdrane<!--structure not shown<br/>[[Image:Widdrane.png|70px]]-->
−
| widdrane
+
 
|}
 
|}
 
|-
 
|-
 
| (Z,E)-germacradiene<br/>[[Image:(Z,E)-Germacradienyl cation.png|100px]]
 
| (Z,E)-germacradiene<br/>[[Image:(Z,E)-Germacradienyl cation.png|100px]]
−
| cadinane<br/>[[Image:(+)-delta-Cadinene.png|80px]]
+
| cadinane<br/>[[Image:Cadinane.png|90px]]
−
* bulgarane, calamenene, muurolane, amorphane, cadalane
+
* muurolane<br/>[[Image:Muurolane.png|80px]]
−
* alliacane/primnatriene ... 2(3&rarr;4) abeo cadinane
+
* bulgarane<br/>[[Image:Bulgarane.png|80px]]
−
* oplopane ... 3(4&rarr;5) abeo cadinane
+
* amorphane<br/>[[Image:Amorphane.png|80px]]
−
* mutisianthol ... 6(7&rarr;8) abeo cadinane
+
* calamenene<br/>[[Image:Calamenene.png|80px]]
−
* copaane ... 5,10 cyclo cadinane
+
* cadalane<br/>[[Image:Cadalane.png|80px]]
 +
* alliacane ... 2(3&rarr;4) abeo cadinane<br/>[[Image:Alliacane.png|80px]]
 +
* primnatriene ... 2(3&rarr;4) abeo cadinane<br/>[[Image:Primnatriene.png|80px]]
 +
* oplopane ... 3(4&rarr;5) abeo cadinane<br/>[[Image:Oplopane.png|80px]]
 +
* mutisianthol ... 6(7&rarr;8) abeo cadinane<br/>[[Image:Mutisianthol.png|90px]]
 +
* copaane ... 5,10 cyclo cadinane<br/>[[Image:Copaane.png|80px]]
 
|-
 
|-
 
|rowspan="2"| (Z,E)-humulane<br/>[[Image:(Z,E)-Humulyl cation.png|100px]]
 
|rowspan="2"| (Z,E)-humulane<br/>[[Image:(Z,E)-Humulyl cation.png|100px]]
−
| [http://onlinelibrary.wiley.com/doi/10.1002/ejoc.200300812/pdf himachalane]
+
| [http://onlinelibrary.wiley.com/doi/10.1002/ejoc.200300812/pdf himachalane]<br/>[[Image:Himachalane.png|85px]]
−
* lippifoliane
+
* lippifoliane<br/>[[Image:Lippifoliane.png|80px]]
−
* longipinane
+
* longipinane<br/>[[Image:Longipinane.png|75px]]
−
* longibornane
+
* longibornane<br/>[[Image:Longibornane.png|75px]]
−
* longifolane<br/>[[Image:(+)-Longifolene.png|80px]]
+
* longifolane<br/>[[Image:Longifolane.png|70px]]<!--[[Image:(+)-Longifolene.png|60px]]-->
 
|-
 
|-
−
| protoilludane
+
| protoilludane<br/>[[Image:Protoilludane.png|95px]]
−
* illudane
+
* illudane<br/>[[Image:Illudane.png|85px]]
−
* illudalane ... 4,6-secoilludane
+
* illudalane ... 4,6-secoilludane<br/>[[Image:Illudalane.png|85px]]
−
* sterpurane ... 5(6&rarr;7)-abeoilludane
+
* sterpurane ... 5(6&rarr;7)-abeoilludane<br/>[[Image:Sterpurane.png|85px]]
−
* lactarane, isolactarane, marasmane, merulane  
+
* isolactarane<br/>[[Image:Isolactarane.png|85px]]
−
| hirsutane
+
* merulane<br/>[[Image:Merulane.png|85px]]
 +
* lactarane<br/>[[Image:Lactarane.png|85px]]
 +
* marasmane<br/>[[Image:Marasmane.png|75px]]
 +
| hirsutane<br/>[[Image:Hirsutane.png|90px]]
 
|-
 
|-
 
| cycloheptenyl cation<br/>[[Image:Cycloheptenyl cation.png|100px]]
 
| cycloheptenyl cation<br/>[[Image:Cycloheptenyl cation.png|100px]]
Line 172: Line 199:
 
* zizaane<br/>[[Image:Zizaane.png|80px]]
 
* zizaane<br/>[[Image:Zizaane.png|80px]]
 
* prezizaane<br/>[[Image:Prezizaane.png|80px]]
 
* prezizaane<br/>[[Image:Prezizaane.png|80px]]
 +
* clovane<br/>[[Image:Clovane.png|80px]]
 +
* precapnellane<br/>[[Image:Precapnellane.png|80px]]
 +
* capnellane<br/>[[Image:Capnellane.png|80px]]
 +
* pentalenane<br/>[[Image:Pentalenane.png|80px]]
 +
* silphinane<br/>[[Image:Silphinane.png|80px]]
 +
* silphiperfoliane<br/>[[Image:Silphiperfoliane.png|80px]]
 +
* presilphiperfolane<br/>[[Image:Presilphiperfolane.png|80px]]
 +
* isocomane<br/>[[Image:Isocomane.png|80px]]
 +
* panasinsane<br/>[[Image:Panasinsane.png|80px]]
 +
* modhephane<br/>[[Image:Modhephane.png|80px]]
 +
* quadrane<br/>[[Image:Quadrane.png|80px]]
 +
* campherenane<br/>[[Image:Campherenane.png|80px]]
 +
* alpha-santalane<br/>[[Image:alpha-Santalane.png|80px]]
 +
* beta-santalane<br/>[[Image:beta-Santalane.png|80px]]
 +
* sativane<br/>[[Image:Sativane.png|80px]]
 +
* helminthosporane<br/>[[Image:Helminthosporane.png|80px]]
 +
* copacamphane<br/>[[Image:Copacamphane.png|80px]]
 +
* cyclocopacamphane<br/>[[Image:Cyclocopacamphane.png|80px]]
 +
* sinularane<br/>[[Image:Sinularane.png|80px]]
 +
* cyclosinularane<br/>[[Image:Cyclosinularane.png|80px]]
 
|-
 
|-
 
|}
 
|}

Latest revision as of 13:17, 22 July 2014

Contents

[edit] Sesquiterpene (C15)

[edit] Ring configuration

[edit] Germacrane


[edit] Sesquiterpenes

[edit] Biosynthesis

[edit] Overview

Two major classes of terpene synthases exist: "transoid" and "cisoid" synthase. Transoid synthase directly ionizes ('trans','trans')-farnesyl diphosphate, whereas Cisoid synthase first isomerizes C2-C3 double bond to produce the neutral (3'R')- or (3'S')-nerolidyl diphosphate (enzyme-bound) and then ionizes it.

Substrate Type Intermediate
Farnesyl diphosphate (FPP)
Farnesyl diphosphate.png 		Transoid synthase on (2-trans,6-trans)-FPP
 Farnesyl cation.png
Cisoid synthase on (2-cis,6-trans)-FPP
 (nerolidyl cation)
Nerolidyl cation.png


References


[edit] Sesquiterpene Synthase

farnesyl diphosphate
Farnesyl diphosphate.png
Arrow00d35.png
farnesyl cation
Farnesyl cation.png
farnesane, acyclic ones cyclobutane, cyclopentane cyclofarnesan
(E,E)-germacradiene
(E,E)-Germacradienyl cation.png
  • germacrane
    Germacrene A.png
  • lepidozane
    Lepidozane.png
  • bicyclogermacrane
    Bicyclogermacrane.png
eudesmane (= selinane)
Eudesmanyl cation.png
  • cycloeudesmane
    Cycloeudesmane.png
  • elemane ... 7,8 seco form
    Elemene.png
  • emmotin ... 14(10→1) abeo form
    Emmotin.png
  • farfugin ... 14(10→9) abeo form
    Farfugin.png
  • gorgonane 11(7→6) abeo form
    Gorgonane.png
  • oppositane ... 8(7→6) abeo form
    Oppositane.png
  • valerane (= jatamansane) 15(4→5) abeo form
    Valerane.png
vetispiradienyl cation
Vetispiradienyl cation.png
  • vetispiradiene
    Vetispiradiene.png
  • spirovetivane (= vetispirane)
    Spirovetivane.png
eremophilane (= 14(10→5) abeoeudesmane)
Eremophilenyl cation.png
  • aristolochene
    5-epi-Aristolochene.png
  • aristolane ... 6,11-cyclo form
    Aristolane.png
  • chiloscyphane ...8(7→6) abeo form
    Chiloscyphane.png
  • nardosinane ... 11(7→6) abeo form
    Nardosinane.png
  • cacalol ... 14(5→6) abeo form
    Cacalol.png
  • fukinane ... 9(8→7) abeo form
    Fukinane.png Petasites japonicus
  • brasilane
    Brasilane.png
  • thapsane
    Thapsane.png
  • ishwarane
    Ishwarane.png
guaiane
Guaiane.png
  • xanthane ... 4,5 seco form
    Xanthane.png
  • carabrane ... 4,5 seco form
    Carabrane.png
  • pseudoguaiane ... 15(4→5) abeo form
    Pseudoguaiane.png
  • valerenane ... 8(7→6) abeo form
    Valerenane.png

cycloguaiane

  • cubebane ... 1,6-cyclo form
    Cubebane.png
  • ivaxillarane ... 8,10-cyclo form
    Ivaxillarane.png
  • aromadendrane ... 6,11- cyclo form
    Aromadendrane.png
  • rotundane ... 10,12-cyclo form
    Rotundane.png
  • patchoulane ... 1,11-cyclo form
    Patchoulane.png
  • bourbonane ... 6,10-cyclo form
    Bourbonane.png
(E,E)-humulane
(E,E)-Humulyl cation.png
  • bicyclohumulane
    Bicyclohumulane.png
caryophyllane
(E)-beta-Caryophyllene.png
africanane
Africanane.png
drimane
Drimane.png
  • iresin
    Iresin.png
  • coloratane
    Coloratane.png
nerolidyl cation
Nerolidyl cation.png 		bisabolane
Bisabolyl cation.png
  • thujopsane
    (-)-Sesquithujene.png
chamigrane ... 6,11-cyclobisabolane
Chamigrane.png
  • acorane ... 6,10-cyclobisabolane
    Acorane.png
cuparane (= 7,11-cyclobisabolane)
Cuparane.png 		trichothecane [1]
Trichothecane.png
  • gymnomitrane
    Gymnomitrane.png
widdrane
(Z,E)-germacradiene
(Z,E)-Germacradienyl cation.png 		cadinane
Cadinane.png
  • muurolane
    Muurolane.png
  • bulgarane
    Bulgarane.png
  • amorphane
    Amorphane.png
  • calamenene
    Calamenene.png
  • cadalane
    Cadalane.png
  • alliacane ... 2(3→4) abeo cadinane
    Alliacane.png
  • primnatriene ... 2(3→4) abeo cadinane
    Primnatriene.png
  • oplopane ... 3(4→5) abeo cadinane
    Oplopane.png
  • mutisianthol ... 6(7→8) abeo cadinane
    Mutisianthol.png
  • copaane ... 5,10 cyclo cadinane
    Copaane.png
(Z,E)-humulane
(Z,E)-Humulyl cation.png 		himachalane
Himachalane.png
  • lippifoliane
    Lippifoliane.png
  • longipinane
    Longipinane.png
  • longibornane
    Longibornane.png
  • longifolane
    Longifolane.png
protoilludane
Protoilludane.png
  • illudane
    Illudane.png
  • illudalane ... 4,6-secoilludane
    Illudalane.png
  • sterpurane ... 5(6→7)-abeoilludane
    Sterpurane.png
  • isolactarane
    Isolactarane.png
  • merulane
    Merulane.png
  • lactarane
    Lactarane.png
  • marasmane
    Marasmane.png
hirsutane
Hirsutane.png
cycloheptenyl cation
Cycloheptenyl cation.png 		daucane (= carotane)
Daucane.png
  • isodaucane
    Isodaucane.png
furodysin
Furodysin.png
  • furodysinin
    Furodysinin.png
others
pinguisane
Pinguisane.png
picrotoxane
Picrotoxane.png
perforane
Perforane.png
pacifigorgiane
Pacifigorgiane.png
asteriscane
Asteriscane.png
botrydial
Botrydial.png
tricyclic
  • cedrane
    Cedrane.png
  • isocedrane
    Isocedrane.png
  • zizaane
    Zizaane.png
  • prezizaane
    Prezizaane.png
  • clovane
    Clovane.png
  • precapnellane
    Precapnellane.png
  • capnellane
    Capnellane.png
  • pentalenane
    Pentalenane.png
  • silphinane
    Silphinane.png
  • silphiperfoliane
    Silphiperfoliane.png
  • presilphiperfolane
    Presilphiperfolane.png
  • isocomane
    Isocomane.png
  • panasinsane
    Panasinsane.png
  • modhephane
    Modhephane.png
  • quadrane
    Quadrane.png
  • campherenane
    Campherenane.png
  • alpha-santalane
    Alpha-Santalane.png
  • beta-santalane
    Beta-Santalane.png
  • sativane
    Sativane.png
  • helminthosporane
    Helminthosporane.png
  • copacamphane
    Copacamphane.png
  • cyclocopacamphane
    Cyclocopacamphane.png
  • sinularane
    Sinularane.png
  • cyclosinularane
    Cyclosinularane.png

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