Ing. Josef Patzak, PhD. Chmelařský Institut s.r.o., oddělení Biotechnologie Kadaňská 2525, 438 46 Žatec, Česká republika TEL: +420 415732109 mobil: +420 724929535 E-mail:
[email protected]
Cannabaceae < Urticales < Dicotyledons < Magnoliophyta vytrvalá, pnoucí, pravotočivá dvoudomá dlouhodenní 2n = 20 (9A+1G), 2C = 5,6 pg X a Y, typ Drosophila ♀G(2) ♂P5A5 Genetická konference GSGM, 24-26. září 2014, Průhonice
Biosynthesis of hop r esins, essential oils, flavanoids and polyphenols
Shikimate/Arogenate Pathway O
3x OH
Malonyl-CoA
HO
OH
O
HO
OH
HO
Acetyl-CoA
1
19
Isovaleryl-CoA
+
O
16
CH2OPP
2
O SCoA
HO
O HO
Humulone 9
O
O
HO
15
O
O
OH
O
OH
CH2OPP
8
O
O
Lupulone
3 x
O
O
CoAS
OH
HO
+
O
O
5
HO
OH
O
SCoA R
R Hydroxybenzoic acid
OH
OH
Isopentenylpyrophosphate IPP
HO
O
OH
OH
O
OH
Desmethylxanthohumol
HO
14
OMe O
7
CH2OPP
Xanthohumol
CoAS
DMAPP
OH 21
+ OH
O
3’-Prenylchalconaringenin
Isobutyryl-CoA
O
O
8
HO CH2OPP
18
OH
R
O
Naringenin chalcone
OH
6
O
Isobutyryl-CoA
SCoA R O
Mevalonate-5-pyrophosphate
2-Oxoisovalerate
2-Oxoisocaproate
CoAS
Malonyl-CoA
O
OH
12
OH
13
O
OH
+
DMAPP
CH2OPP
OH
O
R
CH2OPP O HO
CH2OP
OH
O
SCoA
4-Coumaroyl-CoA
CHO
HO 4
O HO 11
O
O HO
R
2,3-Dihydroxyisovalerate
14
O Malonyl-CoA
20
Mevalonate-5-phosphate
CoAS Isovaleryl-CoA
DMAPP
O
+ CoAS
OH
O
Mevalonic acid
OH
HO
OH
CH2OH
HO
O
OH
Acetolactate
O
R
SCoA
3
O HO
Pyruvate
10
DMAPP
+
3x SCoA
HMG-CoA
O
OH
Pyruvate
Desoxyhumulone
O
O
+ OH
CH2OPP
8
OH
HO
O
O
+
SCoA
Hydroxycinnamic acid
R O
3-Methylglutaconyl-CoA
O
O O
9
Acetyl-CoA
Acetoacetyl-CoA
DMAPP
OH
SCoA
SCoA SCoA 3-Methylcrotonyl-CoA
O
O
O
O 17
CoAS
8
Phenylalanine/Hydrocynnamate Pathway
SCoA
SCoA Acetyl-CoA
O
+
O
9
O
Phloroisovelerophenone
O
O
+
O
+
18
OH
HO OH
O O
CoAS
O
8
OH
OH
O
HO
OH
HO OH
HO
+
CH2OPP
CH2OPP
8
OH
HO
O
OH HO
+ HO
OH
Phloroisobutyrophenone
O
Dimethylallylpyrophosphate DMAPP
DMAPP
OH
CH2OPP
OH
OH
HO
O
O CH2OPP
OMe O
3’-Geranylchalconaringenin
IPP
5’-Prenylxanthohumol
OH
+
DMAPP
Cohumulone
O Naringenin
8
OH
O
+
HO
CH2OPP
8
OH
HO
O
OH
8
+
O
O OH
CH2OPP
HO
OMe O
H
C
O
Isoxanthohumol
CH2OPP
Linalool
CH2OPP
+ OH
DMAPP
CH2OH Farnesylpyrophosphate
α-Pinene
Camphene
Colupulone
Myrcene
OH
CH2OH
CO2CH3
β-Pinene
OH Limonene
O
HO
α-Terpineol
O
H
H
H α-Ylangene
H
H
p-Cymene
OH
8(9)-p-Methandiene
OH HO
H
O
H
H
α-Cadinene
OH H
HO
β-Ylangene
α-Muurolene
H
H ε-Muurolene
α-Cadinol
H τ-Cadinol
C
C
Involved enzymes: Nerolidol
C
Hop resins
H Bicyclogermacrene
C OH
γ-Elemene
α-bitter acids
C
Germacrene B
Hedycaryol
Germacrene A
+
H
+
+
Cubenol
β-bitter acids
trans-Humulane
cis-Humulane
+ H
β-Bisabolene
α-Selinene
OH
H
C
O
α-Humulene
O
H β-Selinene
H
OH
H
β-Eudesmol
Selina-3,7(11)-diene
H Viridiflorene
H
H
H
H
epoxide II
epoxide I
O
OH
epoxide III
O
OH
HO
H β-Selinenol
OH
O Humulol
Humulenol II
H γ-Eudesmol
OH
HO
H
O
O
O
O
H
Sesquiterpenes
epoxide
O
H
OH
HO H
OH
O
Hop flavanoids
H
H β-Selinene epoxide
Monoterpenes
H
epoxide
H Ledol
O
α-Gurjunene
H Aromadrene
H
α-Selinenol
HO H
H
Humulenol I
H Alloaromadrene
O
O
H
Hop essential oils
H
O
O
Caryophyllene epoxide
H
Selina-4(14),7,(11)-diene
H β-Caryophyllene
H
H α-Eudesmol
H
H
OH
OH OH Proanthodelphinidin
+
OH
C H
O
C
OH
OH O
OH HO OH
OH Proanthocyanidin H
O Kaempferol glycoside
OH OH OH
+
O
OH OH
HO
OH O
β-Cubebene
H
OH
O-Gly
OH
H
H γ-Muurolene
O
O Quercetin glycoside
O
OH
OH HO γ-Terpinene
G HO
OH
OH
α-Terpinene
OH
OH
Gallacatechin
OH
Terpinolene
O-Gly
Kaempferol
OH
α-Cubebene
Carvone
H
O
OH
O
O
OH HO
Catechin
H
OH
OH
OH
Farnesol α-Bergamotene
Cadina-1,4-diene
OH
O
OH
OH
H
OH
H
G
OH
HO
O
25
O
H
α-Copaene
O Quercetin OH
HO
OH Leucocyanidin
C
H
24
OH
H
δ-Cadinene
OH
O
OH
C
H
O
Nerol
C
Methyl geranate
H
HO
OH HO
α-Pinene oxide
C
O Dihydroflavonol
OH
O
6-Geranylnaringenin
β-Farnesene
+
C
OH OH
23
OH
Geraniol
O
24
OH
+
C
+
OH O
HO
8
O
HO
Ocimene
O
H
O O
C
O
6-Prenylnaringenin
OH
CH2OPP
C
γ-Cadinene
O
O
O
Germacrene D
OH
H
DMAPP
HO
22
O
8-Prenylnaringenin
Geranylpyrophosphate
8
8
HO
OH
+
CH2OPP IPP
OH
O
OH
DMAPP
Desoxycohumulone
H Viridiflorol
H Globulol
H Alloglobulol
Hop polyphenols
1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 C H O
G
acetoacetyl CoA thiolase HMG-CoA synthase HMG-CoA reductase MVA kinase mevalonate-5-phosphate kinase mevalonate-5-diphosphate decarboxylase IPP isomerase prenyl transferase acetyl-CoA carboxylase acetohydroxyacid synthase 2-hydroxy-3-oxoacid reductoisomerase dihydroxiacid dehydratase 3 enzymes and precursors 3-methyl-2-oxobutanoate dehydrogenase 3-methylglutaconyl-CoA hydratase methylcrotonyl-CoA carboxylase acyl-CoA dehydrogenase phloroisovaleryl synthase phenylalanine ammonia-lyase chalcone synthase chalcone isomerase flavanone 3-hydroxylase dihydroflavonol/one 4-reductase flavonol synthase flavan-3,4-diol 4-reductase cyclases hydroxylases cytochrome P-450 dependent oxidase 3-O-glycosyltransferases
Humuladienone
Genetická konference GSGM, 24-26. září 2014, Průhonice
1874
1934
950 1850
1850
1629
1300 7361000 1300 1868 1160 1950
1880
1920 Centrum původu
1880
Legenda: 1980
H. lupulus var. lupulus ostatní druhy a variety
H. lupulus var. neomexicanus H. lupulus var. pubescens H. lupulus var. lupuloides H. japonicus H. lupulus var. cordifolius + H. japonicus H. yunnanensis
1650 1799 1930
1822
Genetická konference GSGM, 24-26. září 2014, Průhonice
1929
United States
X (Russia) [16]
(English)
X
X
United Kingdom
O.P.
X
X
Brewers Gold
X
[3]
(German)
X
Columbus
Petham Golding
[50]
O.P.
O.P.
Chinnok
X
[61]
BBI Manitoba
Sunshine
[27]
Willamete
O.P. X
X
Comet
4n 3n
?
?
(Utah wild)
X
Serebr ianka X
Golding
X X
O.P. X
X
X
O.P.
X
X
(English)
X
Cascade [45]
X
Elsasser O.P.
Glacier
X (German)
X
X
Santiam
[8]
[64]
X
Backa
[66]
X O.P. O.P.
[31]
[39]
X(Yugoslavian)X
Izabela
Marynka
[17]
[20]
Saaz
(76/18/80)
Spalter Select
Hallertauer X [26] Gold (75/15/106M)
X (63/5/27M)
Perle [7]
Hallertauer Tradition [22]
X Osvald’s Clone 72
X
Osvald’s Clone 72
X
Bor [56]
Sládek X
X
Wye Target [6]
New Zealand O.P. X White Japan Australia Vine
Estera [14]
X O.P.
Kirin II
X
[1]
Golden Star [9]
(TG)
O.P. X Savinski X O.P. Golding
[52]
O.P.
[32]
X
(2/173)
X
(Sx502)
X Agnus [57]
Buket
Vojvodina
[4]
[54]
X X
O.P.
Ringwood special [43]
[44]
X
X
X
(TG)
X Aurora Bobek [11]
[49] (3/3) 4n 3n
Cicero [58]
3n
Zenith
[25]
[62]
South Africa
Legend: Female Male
X O.P. (3/3)
[46]
(1/9)
Yeoman O.P.
Apolon Ahil Atlas X
X(105/58)
X O.P.
X
Pride of Kent
Pride of Ringwood
X
X
[5]
4n
Czech Republic
X
X
[51]
X X
[55]
Premiant
X
[2]
X O.P. X
(American)
[55]
[53]
Germany
Wye Northdown
(71/16/7M)
X
X
[38]
California Cluster X
[47]
Saazer
X
(54/33/11)
Br amling Cross
X
X
X
X
X
Smooth Cone Callicross
X
Shinshuwase H ü ller X Anfang (81t9)
X
O.P.
Wye Challenger
Poland
Lubelski
[40]
X O.P.
[33]
[41]
[37]
Spalt
Northern Brewer
4n
[48]
Hallertau Hersbruck
Hallertauer Mittelfr ü her
[24]
X O.P.
X
X
(English)
[60]
Taurus
[28]
X
X O.P.
(Yugoslavian) [42] Nadwislavsky
[30]
Crystal
[23]
Late Cluster
[36]
Mer kur
[13]
[63]
Tetnang
O.P.
3n
[29]
Eroica
[19]
Mt. Hood
X
X
Eastwell Golding
X
Centennial Nugget Horizon Liber ty
Sterling
[10]
Magnum
(81/8/13M)
X Saazer (Czech)
X
Galena
(French) [18]
X
Zattler (German)
(21381M)
Br amling
3n
(German)
4n 3n
Str iesselspalt
X 4n
3n
X
4n
Tettnanger
[65]
(75/5/3M)
X
X
(French)
X
X
O.P.
English Golding
Ear ly Green
X
X X
X
(American)
Cantenbury X Golding
X
[67]
(English)
Neomex
[35]
(German)
[12]
X
Bullion
O.P.
[34]
X
Vanguard
Bullion
X
Fuggle
(American)
X Atlas 4n
X (39-06)
X
Crossing
O.P.
Open pollinated
Souther n Brewer
[]
Number
[21]
()
Origin
3n
Celeia
Blisk
[59]
[15]
Outeniqua [68]
Slovenia
Genetická konference GSGM, 24-26. září 2014, Průhonice
Linkage Landrace
Rostlinná výroba 45: 165-172, 1999
Genetická konference GSGM, 24-26. září 2014, Průhonice
a) M2
M1
1605 pb 1198 pb 517 460 396 350
1000 pb 800 pb 600 pb 500 pb 400 pb 300 pb 200 pb
bp bp bp bp
222 pb 179 pb 126 pb
O
B
S
P
A
4382 4527 4715 4353 M2 676 pb 517 pb 460 pb 396 pb 350 pb
400 pb
1500 pb
676 pb
M1 700 pb 600 pb 500 pb
300 pb 222 pb 200 pb
b)
179 pb
M1
O
B
S
P
A
4382 4527 4715 4353 M2 350 pb
300 pb 222 pb 179 pb
200 pb
100 pb
126 pb
c)
M1
O
B
S
P
A
4382 4527 4715 4353 M2 2645 pb 1605 pb
1500 pb
1198 pb 1000 pb 900 pb 800 pb 700 pb 600 pb 500 pb
676 pb 517 pb 460 pb 396 pb 350 pb
400 pb
d)
M1
O
B
S
P
A
4382 4527 4715 4353 M2 2645 pb
1500 pb
1605 pb 1198 pb
Rostlinná Výroba 48: 318-321, 2002 Rostlinná Výroba 48: 343-350, 2002
1000 pb 900 pb 800 pb 700 pb 600 pb 500 pb 400 pb
Genetická konference GSGM, 24-26. září 2014, Průhonice
676 pb 517 pb 460 pb 396 pb 350 pb
Euphytica 121: 9-18, 2001 Euphytica 131: 343-350, 2003
Genetická konference GSGM, 24-26. září 2014, Průhonice
Osv. klon 31 Osv. klon 72 Osv. klon 114 Bor Sládek Agnus Premiant Harmonie Rubín Vital Kazbek 4237 4784 4788 4849 4914 4915 4932 4964 4837
145 SSR loci
HlGA29
HlGA3
HlGT4
Genome 50: 15-25, 2007 Kvasný průmysl 57: 296-304, 2011
Genetická konference GSGM, 24-26. září 2014, Průhonice
Plant Science 162: 1007-1018, 2002 Biologia Plantarum 46: 375-381, 2003 Journal of Agriculture and Food Chemistry 53: 4793-4798, 2005 Biologia Plantarum 50: 48-54, 2006 Journal of Agriculture and Food Chemistry 55: 7767-7776, 2007 Journal of Agriculture and Food Chemistry 58: 902-912, 2010 BMC Plant Biology 12: 27, 2012
Genetická konference GSGM, 24-26. září 2014, Průhonice
http://www.ncbi.nlm.nih.gov ESTs: 75 672 932 (42,158,059,791) TSA: 52 596 023 (42,426,765,504) http://www.planttrichome.org/trichomedb/ ESTs: 825 370 Unigenes: 106 370 Suntory Liquors Limited, Osaka, Japonsko ESTs: 387 929 (915,421,000) 41 228 pravděpodobně genů (29 950 redukováno kvůli heterozygotnosti)
Genetická konference GSGM, 24-26. září 2014, Průhonice
ŽPČ Bor Sládek Premiant Agnus Harmonie Rubín Vital Kazbek Bohemie Saaz late
3 658 EST-SSR loci 17 128 SNPs Harmonie - sadba 6 144 DART
WRKY75
LAR1
CMPS Biologia Plantarum 55: 761-765, 2011 Brewing Science 65: 96-102, 2012
Genetická konference GSGM, 24-26. září 2014, Průhonice
Kvasný Průmysl 59: 2-13, 2013 Kvasný Průmysl 59: 296-305, 2013
Genetická konference GSGM, 24-26. září 2014, Průhonice
Biochemical Systematics and Ecology 38: 136-145, 2010 Genome 53: 545-557, 2010
Genetická konference GSGM, 24-26. září 2014, Průhonice
2,57 Gb odhad (2.05 Gb sekvenováno) cpDNA 180 204 bp, mtDNA 336 811 bp 13 776 946 – 22 012 445 SNPs
Natsume et al. Journal of Plant Physiology, prepared.
Genetická konference GSGM, 24-26. září 2014, Průhonice
Genetická konference GSGM, 24-26. září 2014, Průhonice
Bc. Alena Henychová BC AVČR v.v.i., ÚMBR, České Budějovice VÚRV v.v.i., Praha-Ruzyně EP7254, NAZV Mze, 1997-2000 EP9357, NAZV MZe, 1999-2001 521/99/1591, GAČR, 1999-2001 QC1336, NAZV MZe, 2001-2004 521/03/0072, GAČR, 2003-2005 521/08/0740, GAČR, 2008-2011 QH81052, NAZV MZe, 2008-2012 13-03037S, GAČR, 2013-2017 Genetická konference GSGM, 24-26. září 2014, Průhonice
Genetická konference GSGM, 24-26. září 2014, Průhonice