Limonene Pathway Map

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This pathway was contributed by Shulan Tian and Meaghan Fitzgerald, University of Minnesota.

Limonene (4-isopropenyl-1-methyl-cyclohexene), a monocyclic monoterpene, is the most widespread terpene in the world and is formed by more than 300 plants. (+)-(4R)-limonene is its most widespread form (van der Werf et al., 1999). Limonene is the major constituent of citrus essential oils and is used as a raw material for the chemical synthesis of terpene resin adhesives and flavor materials, such as menthol and carvone.

So far, five different microbial biotransformation pathways for limonene have been proposed. In the middle branch, a soil Pseudomonassp. degradates limonene in the same way as Rhodococcus erythropolis DCL14, but its final product is 1-hydroxy-2-oxolimonene rather than 3-isopropenyl-6-oxoheptanoyl-CoA. The middle branch shows a pathway for (+)-(4R)-limonene; a similar pathway using many of the same enzymes is known for (-)-(4S)-limonene (van der Werf et al., 1999).

The following is a text-format limonene degradation pathway. Organisms which can initiate the pathway are given, but other organisms may also carry out later steps. Follow the links for more information on compounds or reactions.

                   Graphical Map(21k)                                  Graphical Map(8k)
      |--------------------------------------------|               |-----------------------|

      from the
    alpha-Pinene  ----------+------------------+----------------------+-----------------+
      Pathway               |                  |                      |                 |
         |                  |                  |                      |                 |
         V                  V                  V                      V                 V
      Limonene          Limonene       (+)-(4R)-Limonene          Limonene          Limonene
    Penicillium      Pseudomonas sp.      Rhodococcus           Aspergillus       Ps. gladioli
     digitatum        Aspergillus     erythropolis DCL14        cellulosae          Bacillus
   Ps. gladioli       cellulosae         Pseudomonas sp.       Hormonema sp.   stearothermophilus
Arxula adeninivorans       |                   |                      |         Cladosporium sp.
Yarrowia lipolytica        |                   |                      |           P. digitatum
         |                 |                   |                      |                | 
         | limonene 7-     | limonene 6-       | limonene 1,2-        | limonene 3-    | limonene 8-
         | monooxygenase   | monooxygenase     | monooxygenase        | monooxygenase  | hydratase
         V                 V                   V                      V                V
  Perillyl alcohol      Carveol    (4R)-Limonene-1,2-epoxide   Isopiperitenol   alpha-Terpineol
         |                 |                   |                      |
         | perillyl        | carveol           | limonene-1,2-        | isopiperitenol
         | alcohol         | dehydrogenase     | epoxide hydrolase    | dehydrogenase
         | dehydrogenase   |                   |                      |
         V                 V                   V                      V
 Perillyl aldehyde      Carvone   (1S,2S,4R)-Limonene-1,2-diol  Isopiperitenone
         |                 |                   |
         | aldehyde        | carvone           | limonene-1,2-diol
         | dehydrogenase   | reductase         | dehydrogenase
         |                 |                   |
         V                 V                   V
   Perillic acid     Dihydrocarvone   (1S,4R)-1-Hydroxy-
         |                               2-oxolimonene
         |                                     |
         | perillyl-CoA                        | 1-hydroxy-2-
         | synthetase                          | oxolimonene
         V                                     | 1,2-monooxygenase
    Perillyl-CoA                               V
         |                      [(4R)-7-Hydroxy-4-isopropenyl-
         | perillyl-CoA            7-methyl-2-oxo-oxepanone]
         | hydratase                           |
         |                                     | spontaneous reaction
         V                                     |
    2-Hydroxy-4-                               |
isopropenyl cyclohexane-                       V
    1-carboxy-CoA                      (3R)-3-Isopropenyl-
         |                              6-oxoheptanoate
         | 2-hydroxy-4-isopropenyl-            |
         | cyclohexane-1-carboxyl-CoA          | 3-isopropenyl-
         | dehydrogenase                       | 6-oxoheptanoyl-CoA
         V                                     | synthetase
  4-Isopropenyl-                               |
2-ketocyclohexane-                             V
   1-carboxy-CoA                      (3R)-3-Isopropenyl-
         |                            6-oxoheptanoyl-CoA
         | 4-isopropenyl-2-ketocyclo-
         | hexane-1-carboxy-CoA hydrolase
         |
         V
(3R)3-Isopropenyl-
 (3R)pimelyl-CoA


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Page Author(s): Shulan Tian and Meaghan Fitzgerald

July 11, 2017 Contact Us

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