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6alpha-hydroxygermacra-1(10),4,11(13)-trien-12-oate = (+)-costunolide + H2O
(1b), spontaneous
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-
-
germacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH-hemoprotein reductase] + O2 = (+)-costunolide + [oxidized NADPH-hemoprotein reductase] + 2 H2O
overall reaction
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-
-
germacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH-hemoprotein reductase] + O2 = 6alpha-hydroxygermacra-1(10),4,11(13)-trien-12-oate + [oxidized NADPH-hemoprotein reductase] + H2O
(1a)
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-
-
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germacra-1(10),4,11(13)-trien-12-oate,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (6alpha-hydroxylating)
A cytochrome P-450 (heme-thiolate) protein from chicory plants. The enzyme hydroxylates carbon C-6 of germacra-1(10),4,11(13)-trien-12-oate to give 6alpha-hydroxygermacra-1(10),4,11(13)-trien-12-oate, which spontaneously cyclises to form the lactone ring.
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germacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH-hemoprotein reductase] + O2
(+)-costunolide + [oxidized NADPH-hemoprotein reductase] + 2 H2O
germacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH-hemoprotein reductase] + O2
(+)-costunolide + [oxidized NADPH-hemoprotein reductase] + H2O
additional information
?
-
germacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH-hemoprotein reductase] + O2
(+)-costunolide + [oxidized NADPH-hemoprotein reductase] + 2 H2O
Substrates: -
Products: -
?
germacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH-hemoprotein reductase] + O2
(+)-costunolide + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
Substrates: -
Products: -
?
germacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH-hemoprotein reductase] + O2
(+)-costunolide + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
Substrates: -
Products: -
?
germacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH-hemoprotein reductase] + O2
(+)-costunolide + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: -
Products: -
?
germacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH-hemoprotein reductase] + O2
(+)-costunolide + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: -
Products: (+)-costunolide is detected as its Cope rearrangement product dehydrosaussurea lactone
ir
germacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH-hemoprotein reductase] + O2
(+)-costunolide + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: -
Products: -
?
germacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH-hemoprotein reductase] + O2
(+)-costunolide + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: -
Products: -
?
additional information
?
-
-
Substrates: (+)-costunolide synthase is a cytochrome P450 enzyme
Products: -
?
additional information
?
-
-
Substrates: (+)-costunolide synthase is not capable of converting alpha-costic acid and elema-1,3,11(13)-trien-12-oic acid
Products: -
?
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germacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH-hemoprotein reductase] + O2
(+)-costunolide + [oxidized NADPH-hemoprotein reductase] + 2 H2O
germacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH-hemoprotein reductase] + O2
(+)-costunolide + [oxidized NADPH-hemoprotein reductase] + H2O
additional information
?
-
-
Substrates: (+)-costunolide synthase is a cytochrome P450 enzyme
Products: -
?
germacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH-hemoprotein reductase] + O2
(+)-costunolide + [oxidized NADPH-hemoprotein reductase] + 2 H2O
Substrates: -
Products: -
?
germacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH-hemoprotein reductase] + O2
(+)-costunolide + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
Substrates: -
Products: -
?
germacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH-hemoprotein reductase] + O2
(+)-costunolide + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: -
Products: -
?
germacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH-hemoprotein reductase] + O2
(+)-costunolide + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: -
Products: -
?
germacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH-hemoprotein reductase] + O2
(+)-costunolide + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: -
Products: -
?
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NADPH-hemoprotein reductase
-
cytochrome P450
-
-
-
NADPH-hemoprotein reductase
A flavoprotein containing both FMN and FAD. This enzyme catalyses the transfer of electrons from NADPH, an obligatory two-electron donor, to microsomal P-450 monooxygenases, EC 1.14.14._
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NADPH-hemoprotein reductase
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A flavoprotein containing both FMN and FAD. This enzyme catalyses the transfer of electrons from NADPH, an obligatory two-electron donor, to microsomal P-450 monooxygenases, EC 1.14.14._
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C7BL2_LACSA
490
1
55267
Swiss-Prot
Secretory Pathway (Reliability: 2)
C7BL2_TANPA
496
1
56267
Swiss-Prot
Secretory Pathway (Reliability: 1)
C7BL3_CICIN
494
1
55682
Swiss-Prot
Secretory Pathway (Reliability: 2)
A0A2G9IBC6_9LAMI
510
1
58505
TrEMBL
Secretory Pathway (Reliability: 2)
G7KE92_MEDTR
510
1
57901
TrEMBL
Secretory Pathway (Reliability: 1)
A0A396IKG4_MEDTR
535
1
61178
TrEMBL
other Location (Reliability: 3)
A0A072V0W0_MEDTR
516
1
58981
TrEMBL
Secretory Pathway (Reliability: 3)
A0A2P6P3L9_ROSCH
285
0
32732
TrEMBL
other Location (Reliability: 4)
A0A2G9HYR6_9LAMI
148
1
17161
TrEMBL
Secretory Pathway (Reliability: 5)
A0A2G9HN69_9LAMI
509
2
58481
TrEMBL
Secretory Pathway (Reliability: 4)
A0A7C9A036_OPUST
247
0
28102
TrEMBL
other Location (Reliability: 1)
A0A2G9HZZ9_9LAMI
510
1
58480
TrEMBL
Secretory Pathway (Reliability: 3)
A0A7C9EVL8_OPUST
397
0
45257
TrEMBL
Mitochondrion (Reliability: 4)
A0A2G9HZX7_9LAMI
314
1
35890
TrEMBL
Secretory Pathway (Reliability: 5)
A0A396HTE4_MEDTR
82
0
9572
TrEMBL
other Location (Reliability: 5)
A0A396JBK5_MEDTR
147
1
16729
TrEMBL
Mitochondrion (Reliability: 5)
A0A7C9E9P8_OPUST
155
0
17327
TrEMBL
other Location (Reliability: 2)
G7KE96_MEDTR
229
1
25923
TrEMBL
Secretory Pathway (Reliability: 1)
A0A2G9IBB5_9LAMI
506
1
58207
TrEMBL
Secretory Pathway (Reliability: 4)
A0A2G9IBB7_9LAMI
510
1
58288
TrEMBL
Secretory Pathway (Reliability: 5)
A0A7C9E274_OPUST
502
1
57274
TrEMBL
Secretory Pathway (Reliability: 4)
A0A396I116_MEDTR
216
0
24673
TrEMBL
Secretory Pathway (Reliability: 3)
A0A7C9AQ63_OPUST
188
0
21426
TrEMBL
other Location (Reliability: 1)
A0A072UJ58_MEDTR
201
0
22935
TrEMBL
other Location (Reliability: 4)
A0A7C9E8W6_OPUST
143
0
15919
TrEMBL
other Location (Reliability: 4)
A0A396IHM7_MEDTR
164
0
18562
TrEMBL
other Location (Reliability: 2)
A0A072UQN0_MEDTR
427
1
48467
TrEMBL
Secretory Pathway (Reliability: 1)
A0A396I163_MEDTR
177
1
20822
TrEMBL
Secretory Pathway (Reliability: 4)
A0A7C9A276_OPUST
243
0
27630
TrEMBL
other Location (Reliability: 1)
A0A7C9E2J1_OPUST
228
0
25676
TrEMBL
other Location (Reliability: 1)
A0A7C9E7P4_OPUST
165
1
18865
TrEMBL
Secretory Pathway (Reliability: 2)
A0A7C9AP48_OPUST
175
0
19842
TrEMBL
Mitochondrion (Reliability: 4)
A0A7C9A2P1_OPUST
247
0
28096
TrEMBL
other Location (Reliability: 2)
A0A7C9E3C3_OPUST
103
0
11839
TrEMBL
Mitochondrion (Reliability: 2)
G7KE88_MEDTR
512
1
58271
TrEMBL
Secretory Pathway (Reliability: 2)
A0A396HTH7_MEDTR
161
1
18511
TrEMBL
Chloroplast (Reliability: 5)
A0A7C9A213_OPUST
248
0
28175
TrEMBL
other Location (Reliability: 1)
G7KE81_MEDTR
508
1
57851
TrEMBL
Secretory Pathway (Reliability: 1)
A0A3Q8QEF7_CICIN
494
1
55673
TrEMBL
Secretory Pathway (Reliability: 2)
A0A7C9ASC2_OPUST
287
0
33016
TrEMBL
Mitochondrion (Reliability: 4)
A0A7C9E832_OPUST
391
0
44988
TrEMBL
Mitochondrion (Reliability: 5)
G7KE79_MEDTR
510
1
58347
TrEMBL
Secretory Pathway (Reliability: 2)
A0A2G9IBI0_9LAMI
487
1
55833
TrEMBL
Secretory Pathway (Reliability: 4)
A0A3Q8QEL6_CICEN
494
1
55654
TrEMBL
Secretory Pathway (Reliability: 2)
A0A7C9E3V4_OPUST
315
1
36199
TrEMBL
Secretory Pathway (Reliability: 4)
A0A7C9E5K7_OPUST
173
1
19978
TrEMBL
other Location (Reliability: 4)
A0A059WMF6_CYNCA
494
0
55909
TrEMBL
-
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COS expression analysis in plants with Mg2+ or Mn2+ feeding or without, overview
-
expressed in Saccharomyces cerevisiae strain EPY300
expressed in yeast cells and in Nicotiana benthamiana leaves
gene CYP71Bl5, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, transient expression in Nicotiana benthamiana leaves via Agrobacterium tumefaciens strain AGL0 electrotransformation leading to production of costunolide in tabacco leaves determined as costunolide-cysteine and costunolide-glutathione
expressed in Saccharomyces cerevisiae strain EPY300
-
expressed in Saccharomyces cerevisiae strain EPY300
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de Kraker, J.W.; Franssen, M.C.R.; Joerink, M.; de Groot, A.; Bouwmeester, H.J.
Biosynthesis of costunolide, dihydrocostunolide, and leucodin. Demostration of cytochrome P450-catalyzed formation of the lactone ring present in sesquiterpene lactones of chicory
Plant Physiol.
129
257-268
2002
Cichorium intybus
brenda
Ikezawa, N.; Goepfert, J.C.; Nguyen, D.T.; Kim, S.U.; OMaille, P.E.; Spring, O.; Ro, D.K.
Lettuce costunolide synthase (CYP71BL2) and its homolog (CYP71BL1) from sunflower catalyze distinct regio- and stereoselective hydroxylations in sesquiterpene lactone metabolism
J. Biol. Chem.
286
21601-21611
2011
Helianthus annuus, Lactuca sativa (F8S1I0)
brenda
Liu, Q.; Majdi, M.; Cankar, K.; Goedbloed, M.; Charnikhova, T.; Verstappen, F.W.; de Vos, R.C.; Beekwilder, J.; van der Krol, S.; Bouwmeester, H.J.
Reconstitution of the costunolide biosynthetic pathway in yeast and Nicotiana benthamiana
PLoS ONE
6
e23255
2011
Cichorium intybus (G3GBK0), Cichorium intybus
brenda
Farzadfar, S.; Zarinkamar, F.; Behmanesh, M.; Hojati, M.
Magnesium and manganese interactively modulate parthenolide accumulation and the antioxidant defense system in the leaves of Tanacetum parthenium
J. Plant Physiol.
202
10-20
2016
Tanacetum parthenium
brenda
Eljounaidi, K.; Cankar, K.; Comino, C.; Moglia, A.; Hehn, A.; Bourgaud, F.; Bouwmeester, H.; Menin, B.; Lanteri, S.; Beekwilder, J.
Cytochrome P450s from Cynara cardunculus L. CYP71AV9 and CYP71BL5, catalyze distinct hydroxylations in the sesquiterpene lactone biosynthetic pathway
Plant Sci.
223
59-68
2014
Cynara cardunculus var. altilis (A0A059WMF6), Cynara cardunculus var. altilis
brenda
Frey, M.; Klaiber, I.; Conrad, J.; Spring, O
CYP71BL9, the missing link in costunolide synthesis of sunflower
Phytochemistry
177
112430
2020
Helianthus annuus
brenda