secologanin and strictosidine biosynthesis

Miettinen K, Dong L, Navrot N, Schneider T, Burlat V, Pollier J, Woittiez L, van der Krol S, Lugan R, Ilc T, Verpoorte R, Oksman-Caldentey K, Martinoia E, Bouwmeester H, Goossens A, Memelink J, Werck-Reichhart D. Erratum: Corrigendum: The seco-iridoid pathway from Catharanthus roseus. Nature Communications. 2014 Jun 24;5(1):4175. doi: 10.1038/ncomms5175.; Geu-Flores F, Sherden NH, Courdavault V, Burlat V, Glenn WS, Wu C, Nims E, Cui Y, O’Connor SE. An alternative route to cyclic terpenes by reductive cyclization in iridoid biosynthesis. Nature. 2012 Nov 21;492(7427):138–42. doi: 10.1038/nature11692.

Metabolites

(6E)-8-Hydroxygeraniol

Formula: C10H18O2 (170.1306728)

CAS ID: 26488-97-1

(6E)-8-Oxogeranial

Formula: C10H14O2 (166.09937440000002)

CAS ID: 80054-40-6

CO2

Formula: CO2 (43.98983)

CAS ID: 124-38-9

Diphosphate

Formula: H4P2O7 (177.9432294)

CAS ID: 2466-09-3

Geraniol

Formula: C10H18O (154.1357578)

CAS ID: 106-24-1

H+

Formula: H (1.0078246)

CAS ID: 12408-02-5

H2O

Formula: H2O (18.0105642)

CAS ID: 7732-18-5

Loganin

Formula: C17H26O10 (390.1525896)

CAS ID: 18524-94-2

Magnesium cation

Formula: Mg (23.98505)

CAS ID: 22537-22-0

Manganese(2+)

Formula: Mn (54.938046)

CAS ID: 7439-96-5

Oxygen

Formula: O2 (31.98983)

CAS ID: 7782-44-7

Secologanin

Formula: C17H24O10 (388.13694039999996)

CAS ID: 19351-63-4

iodoacetamide

Formula: C2H4INO (184.9337644)

CAS ID: 144-48-9

potassium cyanide

Formula: CKN (64.966782)

CAS ID: 151-50-8

NADPH(4-)

Formula: C21H26N7O17P3 (741.0598016)

CAS ID: 53-57-6

UDP(3-)

Formula: C9H11N2O12P2 (400.9787246)

CAS ID: 86527-70-0

NADP(3-)

Formula: C21H25N7O17P3 (740.051977)

CAS ID: 53-59-8

N-Methylmaleimide

Formula: C5H5NO2 (111.032027)

CAS ID: 930-88-1



Enzyme

EC Number name full name note
1.14.14.83 geraniol 8-hydroxylase geraniol,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (8-hydroxylating)
1.14.14.85 7-deoxyloganate 7-hydroxylase 7-deoxyloganate,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (7alpha-hydroxylating)
1.3.1.122 (S)-8-oxocitronellyl enol synthase (S)-8-oxocitronellyl enol:NAD(P)+ oxidoreductase
2.1.1.50 loganate O-methyltransferase S-adenosyl-L-methionine:loganate 11-O-methyltransferase
2.4.1.323 7-deoxyloganetic acid glucosyltransferase UDP-alpha-D-glucose:7-deoxyloganetate O-D-glucosyltransferase
3.5.99.13 strictosidine synthase 3-alpha(S)-strictosidine tryptamine-hydrolase (secologanin-forming)
4.1.1.105 L-tryptophan decarboxylase L-tryptophan carboxy-lyase
4.1.1.28 aromatic-L-amino-acid decarboxylase Aromatic-L-amino-acid carboxy-lyase


Pathway Source

Organism Taxonomy Group Enzyme List Source Ratio
Pseudomonas putida KT2440 MAGs 4.1.1.28 12.50%
Citrus x changshan-huyou MAGs 2.4.1.323 12.50%
Mediterraneibacter gnavus ATCC 29149 MAGs 4.1.1.105 12.50%
Saccharopolyspora erythraea NRRL 2338 MAGs 4.1.1.28 12.50%
Pseudomonas entomophila L48 MAGs 4.1.1.28 12.50%
Teredinibacter turnerae T7901 MAGs 4.1.1.28 12.50%
Aspergillus fumigatus Af293 MAGs 4.1.1.28 12.50%
Chloroflexus aggregans DSM 9485 MAGs 4.1.1.28 12.50%
Sinorhizobium meliloti 1021 MAGs 4.1.1.28 12.50%
Coccidioides posadasii C735 delta SOWgp MAGs 4.1.1.28 12.50%
Psilocybe cubensis fungi 4.1.1.105 12.50%
Bacillus atrophaeus bacteria 4.1.1.28 12.50%
Diaphorina citri invertebrate 4.1.1.28 12.50%
Psilocybe cyanescens MAGs 4.1.1.105 12.50%
Citrus unshiu MAGs 2.4.1.323 12.50%
Oryza sativa Japonica Group MAGs 4.1.1.28 12.50%
Penicillium expansum fungi 4.1.1.105 12.50%
Rattus norvegicus vertebrate_mammalian 4.1.1.28 12.50%
Mus musculus vertebrate_mammalian 4.1.1.28 12.50%
Homo sapiens vertebrate_mammalian 4.1.1.28 12.50%