TerSynDB
TerSyn Pathway : Menthol Biosynthesis PDF
Reaction: EC 1.1.1.208 : (+)-neomenthol + NADP+ = (-)-menthone + NADPH + H+
Reaction: EC 1.1.1.207 : (-)-menthol + NADP+ = (-)-menthone + NADPH + H+
Reaction: EC 1.14.13.104 : (+)-pulegone + NADPH + H+ + O2 = (+)-menthofuran + NADP+ + H2O
Reaction: EC 1.3.1.81: (1) (-)-menthone + NADP+ = (+)-pulegone + NADPH + H+
(2) (+)-isomenthone + NADP+ = (+)-pulegone + NADPH + H+ 
Reaction: EC 1.3.1.82 : (+)-cis-isopulegone + NADP+ = (-)-isopiperitenone + NADPH + H+  
Reaction: EC 1.1.1.223 : (-)-trans-isopiperitenol + NAD+ = (-)-isopiperitenone + NADH + H+  
Reaction: EC 1.14.13.47: (S)-limonene + NADPH + H+ + O2 = (-)-trans-isopiperitenol + NADP+ + H2O 
Reaction: EC 4.2.3.16 : geranyl diphosphate = (S)-limonene + diphosphate 

Menthol biosynthesis pathway mapping

The Menthol Biosynthesis Pathway; Mapping Table below shows the complete pathway enzymes responsible for synthesis of Menthol in Mentha Species. The first row shows the enzymes (E1,E2,E3,E4,E5,E6,E7) sequentially as shown in the above figure for menthol biosynthesis; below it  shows the step by step mapping of each enzyme with different plants and represent the orthology with Mentha. In the table [YES] represent the presence of the particular ortholog enzyme with its accession number and %Identity. Here [NO] represent the absence of enzyme in that plant i.e it does not show any orthology with particular enzyme. . ....more.

S.NO

E1 (Geranyl diphosphate synthase )

(AAF08793.1) (%identity)

E2 (limonene synthase)

[AAC37366.1]

E3 (limonene 3- mono-oxygenease)

[Q6IV13]

E4 (isopiperitenol dehydrogenase)

[Q5C9I9]

 

E5 (isopiperitenol reductase)

[Q6WAU1]

 

 

E6 (pulegone reductase)

[Q6WAU0]

 

E7 ( menthol dehydrogenase) 

[Q5CAF4]

 
MENTHOL Synthesise
1

Mentha x piperita

[AAF08793.1/100]

YES

 

YES

 

YES

 

YES

 

YES

 

YES

AAQ55960.1/ 100]

 

 
2

Mentha canadensis 

[ABR15420.1/98]

YES

 

YES

 

YES

 

YES

 

YES

 

YES

 
3

Ricinus communis

[XP_002525096.1/73] 

YES

 

YES

 

YES

 

YES

 

YES

 

YES

 
4

Vitis vinifera

[XP_002273789.1/ 69]

YES

 
NO

YES

 

YES

 

YES

 

YES

 
5

Glycine max 

[XP_003547995.1/ 69]
NO

YES

 

YES

 

YES

 

YES

 

YES

 
6

Prunus persica 

[EMJ05575.1/69]
NO

YES

 

YES

 

YES

 

YES

 

YES

 
7

Solanum tuberosum 

[XP_006363135.1/68]
NO

YES

 

YES

[XP_006367070.1/ 55]

 

YES

 

 YES

 

YES

 
8

Citrus sinensis 

[XP_006466719.1/ 65]
NO

YES

 

YES

 

YES

 

YES

 

YES

 
9

Solanum lycopersicum 

[NP_001234087.1/ 67]
NO

YES

 

YES

 

YES

 

YES

 

YES

 
10

Phaseolus vulgaris

[ESW28009.1/ 68]
NO

YES

 

YES

 

YES

 

YES

ESW06329.1/ 65]

 

YES

 
11

Medicago truncatula 

[XP_003629488.1/ 71]
NO

YES

 

YES

 

YES

 
NO

YES

XP_003627602.1/ 54]

 
12

Citrus clementina 

[XP_006425738.1/ 64]
NO

YES

 

YES

 

YES

 
NO

YES

 
13

Theobroma cacao

[EOX91186.1/ 65] 
NO
N0

YES

 

YES

 
14

Eutrema salsugineum

[XP_006411959.1/ 75]
NO
NO

YES

 

YES

XP_006415911.1/ 64]

 
15

Arabidopsis lyrata

[XP_002869021.1/ 76]
NO
NO
NO
16

Arabidopsis thaliana

[NP_195399.1/ 68]
NO
NO

YES

 
NO
17

Populus trichocarpa

[XP_002310785.1/ 74]
NO
NO

YES

 
18

Capsella rubella

[XP_006282650.1/ 76]
NO
NO

YES

 
NO
19

Cicer arietinum

[XP_004509239.1/ 70]
NO

YES

 
NO
NO
20

Fragaria vesca subsp. vesca 

[XP_004300598.1/ 70]
NO

YES

 

YES

 
NO
NO
21

Amborella trichopoda 

[ERN17565.1/ 71]
NO
NO

YES

 
NO
22

Capsicum annuum

[P80042.1/ 64] 
NO

YES

 
NO
NO
23

Salvia miltiorrhiza

[AEZ55681.1/ 77]

YES

 

YES

 
NO
NO
NO
NO
24

Adonis aestivalis var. palaestina

[AAV74396.1/ 76]
NO
NO

YES

 
NO
NO
NO
25

Catharanthus roseus

[AGL91645.1/ 69]
NO

YES

 
NO
NO
NO
NO
26

Cucumis melo 

[AGN48013.1/ 78]
NO
NO

YES

 
NO
NO
NO

 

References
1. "(-)-Menthol biosynthesis and molecular genetics". Croteau RB1, Davis EM, Ringer KL, Wildung MR.
2. "Enhanced specificity of mint geranyl pyrophosphate synthase by modifying the R-loop interactions."
Hsieh F.L., Chang T.H., Ko T.P., Wang A.H.
J. Mol. Biol. 404:859-873(2010) [PubMed] [Europe PMC] [Abstract]
3. "Regiospecific cytochrome P450 limonene hydroxylases from mint (Mentha) species: cDNA isolation, characterization, and functional expression of (-)-4S-limonene-3-hydroxylase and (-)-4S-limonene-6-hydroxylase."\Lupien99: Lupien S, Karp F, Wildung M, Croteau R (1999). Arch Biochem Biophys 368(1);181-92. PMID: 10415126
4. "Geranyl diphosphate synthase: cloning, expression, and characterization of this prenyltransferase as a heterodimer."
Burke C.C., Wildung M.R., Croteau R.
Proc. Natl. Acad. Sci. U.S.A. 96:13062-13067(1999) [PubMed] [Europe PMC] [Abstract]
   
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