Valencene

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Jules Beekwilder - One of the best experts on this subject based on the ideXlab platform.

  • Valencene oxidase CYP706M1 from Alaska cedar (Callitropsis nootkatensis)
    FEBS letters, 2014
    Co-Authors: Katarina Cankar, Adele Van Houwelingen, Dirk Bosch, Theo Sonke, Harro J Bouwmeester, Miriam Goedbloed, Rokus Renirie, René M. De Jong, Jules Beekwilder
    Abstract:

    (+)-Nootkatone is a natural sesquiterpene ketone used in grapefruit and citrus flavour compositions. It occurs in small amounts in grapefruit and is a major component of Alaska cedar (Callitropsis nootkatensis) heartwood essential oil. Upon co-expression of candidate cytochrome P450 enzymes from Alaska cedar in yeast with a Valencene synthase, a C. nootkatensis Valencene oxidase (CnVO) was identified to produce trans-nootkatol and (+)-nootkatone. Formation of (+)-nootkatone was detected at 144 ± 10 μg/L yeast culture. CnVO belongs to a new subfamily of the CYP706 family of cytochrome P450 oxidases.

  • Valencene synthase from the heartwood of Nootka cypress (Callitropsis nootkatensis) for biotechnological production of Valencene.
    Plant biotechnology journal, 2013
    Co-Authors: Jules Beekwilder, Katarina Cankar, Adele Van Houwelingen, Theo Sonke, Harro J Bouwmeester, René M. De Jong, Aalt D. J. Van Dijk, Geert Stoopen, Jihane Achkar, Dirk Bosch
    Abstract:

    Summary Nootkatone is one of the major terpenes in the heartwood of the Nootka cypress Callitropsis nootkatensis. It is an oxidized sesquiterpene, which has been postulated to be derived from Valencene. Both Valencene and nootkatone are used for flavouring citrus beverages and are considered among the most valuable terpenes used at commercial scale. Functional evaluation of putative terpene synthase genes sourced by large-scale EST sequencing from Nootka cypress wood revealed a Valencene synthase gene (CnVS). CnVS expression in different tissues from the tree correlates well with nootkatone content, suggesting that CnVS represents the first dedicated gene in the nootkatone biosynthetic pathway in C. nootkatensis The gene belongs to the gymnosperm-specific TPS-d subfamily of terpenes synthases and its protein sequence has low similarity to known citrus Valencene synthases. In vitro, CnVS displays high robustness under different pH and temperature regimes, potentially beneficial properties for application in different host and physiological conditions. Biotechnological production of sesquiterpenes has been shown to be feasible, but productivity of microbial strains expressing Valencene synthase from Citrus is low, indicating that optimization of Valencene synthase activity is needed. Indeed, expression of CnVS in Saccharomyces cerevisiae indicated potential for higher yields. In an optimized Rhodobacter sphaeroides strain, expression of CnVS increased Valencene yields 14-fold to 352 mg/L, bringing production to levels with industrial potential.

  • a chicory cytochrome p450 mono oxygenase cyp71av8 for the oxidation of Valencene
    FEBS Letters, 2011
    Co-Authors: Katarina Cankar, Adele Van Houwelingen, Dirk Bosch, Theo Sonke, Harro J Bouwmeester, Jules Beekwilder
    Abstract:

    Chicory (Cichorium intybus L.), which is known to have a variety of terpene-hydroxylating activities, was screened for a P450 mono-oxygenase to convert (+)-Valencene to (+)-nootkatone. A novel P450 cDNA was identified in a chicory root EST library. Co-expression of the enzyme with a Valencene synthase in yeast, led to formation of trans-nootkatol, cis-nootkatol and (+)-nootkatone. The novel enzyme was also found to catalyse a three step conversion of germacrene A to germacra-1(10),4,11(13)-trien-12-oic acid, indicating its involvement in chicory sesquiterpene lactone biosynthesis. Likewise, amorpha-4,11-diene was converted to artemisinic acid. Surprisingly, the chicory P450 has a different regio-specificity on (+)-Valencene compared to germacrene A and amorpha-4,11-diene.

Katarina Cankar - One of the best experts on this subject based on the ideXlab platform.

  • Valencene oxidase CYP706M1 from Alaska cedar (Callitropsis nootkatensis)
    FEBS letters, 2014
    Co-Authors: Katarina Cankar, Adele Van Houwelingen, Dirk Bosch, Theo Sonke, Harro J Bouwmeester, Miriam Goedbloed, Rokus Renirie, René M. De Jong, Jules Beekwilder
    Abstract:

    (+)-Nootkatone is a natural sesquiterpene ketone used in grapefruit and citrus flavour compositions. It occurs in small amounts in grapefruit and is a major component of Alaska cedar (Callitropsis nootkatensis) heartwood essential oil. Upon co-expression of candidate cytochrome P450 enzymes from Alaska cedar in yeast with a Valencene synthase, a C. nootkatensis Valencene oxidase (CnVO) was identified to produce trans-nootkatol and (+)-nootkatone. Formation of (+)-nootkatone was detected at 144 ± 10 μg/L yeast culture. CnVO belongs to a new subfamily of the CYP706 family of cytochrome P450 oxidases.

  • Valencene synthase from the heartwood of Nootka cypress (Callitropsis nootkatensis) for biotechnological production of Valencene.
    Plant biotechnology journal, 2013
    Co-Authors: Jules Beekwilder, Katarina Cankar, Adele Van Houwelingen, Theo Sonke, Harro J Bouwmeester, René M. De Jong, Aalt D. J. Van Dijk, Geert Stoopen, Jihane Achkar, Dirk Bosch
    Abstract:

    Summary Nootkatone is one of the major terpenes in the heartwood of the Nootka cypress Callitropsis nootkatensis. It is an oxidized sesquiterpene, which has been postulated to be derived from Valencene. Both Valencene and nootkatone are used for flavouring citrus beverages and are considered among the most valuable terpenes used at commercial scale. Functional evaluation of putative terpene synthase genes sourced by large-scale EST sequencing from Nootka cypress wood revealed a Valencene synthase gene (CnVS). CnVS expression in different tissues from the tree correlates well with nootkatone content, suggesting that CnVS represents the first dedicated gene in the nootkatone biosynthetic pathway in C. nootkatensis The gene belongs to the gymnosperm-specific TPS-d subfamily of terpenes synthases and its protein sequence has low similarity to known citrus Valencene synthases. In vitro, CnVS displays high robustness under different pH and temperature regimes, potentially beneficial properties for application in different host and physiological conditions. Biotechnological production of sesquiterpenes has been shown to be feasible, but productivity of microbial strains expressing Valencene synthase from Citrus is low, indicating that optimization of Valencene synthase activity is needed. Indeed, expression of CnVS in Saccharomyces cerevisiae indicated potential for higher yields. In an optimized Rhodobacter sphaeroides strain, expression of CnVS increased Valencene yields 14-fold to 352 mg/L, bringing production to levels with industrial potential.

  • a chicory cytochrome p450 mono oxygenase cyp71av8 for the oxidation of Valencene
    FEBS Letters, 2011
    Co-Authors: Katarina Cankar, Adele Van Houwelingen, Dirk Bosch, Theo Sonke, Harro J Bouwmeester, Jules Beekwilder
    Abstract:

    Chicory (Cichorium intybus L.), which is known to have a variety of terpene-hydroxylating activities, was screened for a P450 mono-oxygenase to convert (+)-Valencene to (+)-nootkatone. A novel P450 cDNA was identified in a chicory root EST library. Co-expression of the enzyme with a Valencene synthase in yeast, led to formation of trans-nootkatol, cis-nootkatol and (+)-nootkatone. The novel enzyme was also found to catalyse a three step conversion of germacrene A to germacra-1(10),4,11(13)-trien-12-oic acid, indicating its involvement in chicory sesquiterpene lactone biosynthesis. Likewise, amorpha-4,11-diene was converted to artemisinic acid. Surprisingly, the chicory P450 has a different regio-specificity on (+)-Valencene compared to germacrene A and amorpha-4,11-diene.

Dirk Bosch - One of the best experts on this subject based on the ideXlab platform.

  • Valencene oxidase CYP706M1 from Alaska cedar (Callitropsis nootkatensis)
    FEBS letters, 2014
    Co-Authors: Katarina Cankar, Adele Van Houwelingen, Dirk Bosch, Theo Sonke, Harro J Bouwmeester, Miriam Goedbloed, Rokus Renirie, René M. De Jong, Jules Beekwilder
    Abstract:

    (+)-Nootkatone is a natural sesquiterpene ketone used in grapefruit and citrus flavour compositions. It occurs in small amounts in grapefruit and is a major component of Alaska cedar (Callitropsis nootkatensis) heartwood essential oil. Upon co-expression of candidate cytochrome P450 enzymes from Alaska cedar in yeast with a Valencene synthase, a C. nootkatensis Valencene oxidase (CnVO) was identified to produce trans-nootkatol and (+)-nootkatone. Formation of (+)-nootkatone was detected at 144 ± 10 μg/L yeast culture. CnVO belongs to a new subfamily of the CYP706 family of cytochrome P450 oxidases.

  • Valencene synthase from the heartwood of Nootka cypress (Callitropsis nootkatensis) for biotechnological production of Valencene.
    Plant biotechnology journal, 2013
    Co-Authors: Jules Beekwilder, Katarina Cankar, Adele Van Houwelingen, Theo Sonke, Harro J Bouwmeester, René M. De Jong, Aalt D. J. Van Dijk, Geert Stoopen, Jihane Achkar, Dirk Bosch
    Abstract:

    Summary Nootkatone is one of the major terpenes in the heartwood of the Nootka cypress Callitropsis nootkatensis. It is an oxidized sesquiterpene, which has been postulated to be derived from Valencene. Both Valencene and nootkatone are used for flavouring citrus beverages and are considered among the most valuable terpenes used at commercial scale. Functional evaluation of putative terpene synthase genes sourced by large-scale EST sequencing from Nootka cypress wood revealed a Valencene synthase gene (CnVS). CnVS expression in different tissues from the tree correlates well with nootkatone content, suggesting that CnVS represents the first dedicated gene in the nootkatone biosynthetic pathway in C. nootkatensis The gene belongs to the gymnosperm-specific TPS-d subfamily of terpenes synthases and its protein sequence has low similarity to known citrus Valencene synthases. In vitro, CnVS displays high robustness under different pH and temperature regimes, potentially beneficial properties for application in different host and physiological conditions. Biotechnological production of sesquiterpenes has been shown to be feasible, but productivity of microbial strains expressing Valencene synthase from Citrus is low, indicating that optimization of Valencene synthase activity is needed. Indeed, expression of CnVS in Saccharomyces cerevisiae indicated potential for higher yields. In an optimized Rhodobacter sphaeroides strain, expression of CnVS increased Valencene yields 14-fold to 352 mg/L, bringing production to levels with industrial potential.

  • a chicory cytochrome p450 mono oxygenase cyp71av8 for the oxidation of Valencene
    FEBS Letters, 2011
    Co-Authors: Katarina Cankar, Adele Van Houwelingen, Dirk Bosch, Theo Sonke, Harro J Bouwmeester, Jules Beekwilder
    Abstract:

    Chicory (Cichorium intybus L.), which is known to have a variety of terpene-hydroxylating activities, was screened for a P450 mono-oxygenase to convert (+)-Valencene to (+)-nootkatone. A novel P450 cDNA was identified in a chicory root EST library. Co-expression of the enzyme with a Valencene synthase in yeast, led to formation of trans-nootkatol, cis-nootkatol and (+)-nootkatone. The novel enzyme was also found to catalyse a three step conversion of germacrene A to germacra-1(10),4,11(13)-trien-12-oic acid, indicating its involvement in chicory sesquiterpene lactone biosynthesis. Likewise, amorpha-4,11-diene was converted to artemisinic acid. Surprisingly, the chicory P450 has a different regio-specificity on (+)-Valencene compared to germacrene A and amorpha-4,11-diene.

Harro J Bouwmeester - One of the best experts on this subject based on the ideXlab platform.

  • Valencene oxidase CYP706M1 from Alaska cedar (Callitropsis nootkatensis)
    FEBS letters, 2014
    Co-Authors: Katarina Cankar, Adele Van Houwelingen, Dirk Bosch, Theo Sonke, Harro J Bouwmeester, Miriam Goedbloed, Rokus Renirie, René M. De Jong, Jules Beekwilder
    Abstract:

    (+)-Nootkatone is a natural sesquiterpene ketone used in grapefruit and citrus flavour compositions. It occurs in small amounts in grapefruit and is a major component of Alaska cedar (Callitropsis nootkatensis) heartwood essential oil. Upon co-expression of candidate cytochrome P450 enzymes from Alaska cedar in yeast with a Valencene synthase, a C. nootkatensis Valencene oxidase (CnVO) was identified to produce trans-nootkatol and (+)-nootkatone. Formation of (+)-nootkatone was detected at 144 ± 10 μg/L yeast culture. CnVO belongs to a new subfamily of the CYP706 family of cytochrome P450 oxidases.

  • Valencene synthase from the heartwood of Nootka cypress (Callitropsis nootkatensis) for biotechnological production of Valencene.
    Plant biotechnology journal, 2013
    Co-Authors: Jules Beekwilder, Katarina Cankar, Adele Van Houwelingen, Theo Sonke, Harro J Bouwmeester, René M. De Jong, Aalt D. J. Van Dijk, Geert Stoopen, Jihane Achkar, Dirk Bosch
    Abstract:

    Summary Nootkatone is one of the major terpenes in the heartwood of the Nootka cypress Callitropsis nootkatensis. It is an oxidized sesquiterpene, which has been postulated to be derived from Valencene. Both Valencene and nootkatone are used for flavouring citrus beverages and are considered among the most valuable terpenes used at commercial scale. Functional evaluation of putative terpene synthase genes sourced by large-scale EST sequencing from Nootka cypress wood revealed a Valencene synthase gene (CnVS). CnVS expression in different tissues from the tree correlates well with nootkatone content, suggesting that CnVS represents the first dedicated gene in the nootkatone biosynthetic pathway in C. nootkatensis The gene belongs to the gymnosperm-specific TPS-d subfamily of terpenes synthases and its protein sequence has low similarity to known citrus Valencene synthases. In vitro, CnVS displays high robustness under different pH and temperature regimes, potentially beneficial properties for application in different host and physiological conditions. Biotechnological production of sesquiterpenes has been shown to be feasible, but productivity of microbial strains expressing Valencene synthase from Citrus is low, indicating that optimization of Valencene synthase activity is needed. Indeed, expression of CnVS in Saccharomyces cerevisiae indicated potential for higher yields. In an optimized Rhodobacter sphaeroides strain, expression of CnVS increased Valencene yields 14-fold to 352 mg/L, bringing production to levels with industrial potential.

  • a chicory cytochrome p450 mono oxygenase cyp71av8 for the oxidation of Valencene
    FEBS Letters, 2011
    Co-Authors: Katarina Cankar, Adele Van Houwelingen, Dirk Bosch, Theo Sonke, Harro J Bouwmeester, Jules Beekwilder
    Abstract:

    Chicory (Cichorium intybus L.), which is known to have a variety of terpene-hydroxylating activities, was screened for a P450 mono-oxygenase to convert (+)-Valencene to (+)-nootkatone. A novel P450 cDNA was identified in a chicory root EST library. Co-expression of the enzyme with a Valencene synthase in yeast, led to formation of trans-nootkatol, cis-nootkatol and (+)-nootkatone. The novel enzyme was also found to catalyse a three step conversion of germacrene A to germacra-1(10),4,11(13)-trien-12-oic acid, indicating its involvement in chicory sesquiterpene lactone biosynthesis. Likewise, amorpha-4,11-diene was converted to artemisinic acid. Surprisingly, the chicory P450 has a different regio-specificity on (+)-Valencene compared to germacrene A and amorpha-4,11-diene.

Theo Sonke - One of the best experts on this subject based on the ideXlab platform.

  • Valencene oxidase CYP706M1 from Alaska cedar (Callitropsis nootkatensis)
    FEBS letters, 2014
    Co-Authors: Katarina Cankar, Adele Van Houwelingen, Dirk Bosch, Theo Sonke, Harro J Bouwmeester, Miriam Goedbloed, Rokus Renirie, René M. De Jong, Jules Beekwilder
    Abstract:

    (+)-Nootkatone is a natural sesquiterpene ketone used in grapefruit and citrus flavour compositions. It occurs in small amounts in grapefruit and is a major component of Alaska cedar (Callitropsis nootkatensis) heartwood essential oil. Upon co-expression of candidate cytochrome P450 enzymes from Alaska cedar in yeast with a Valencene synthase, a C. nootkatensis Valencene oxidase (CnVO) was identified to produce trans-nootkatol and (+)-nootkatone. Formation of (+)-nootkatone was detected at 144 ± 10 μg/L yeast culture. CnVO belongs to a new subfamily of the CYP706 family of cytochrome P450 oxidases.

  • Valencene synthase from the heartwood of Nootka cypress (Callitropsis nootkatensis) for biotechnological production of Valencene.
    Plant biotechnology journal, 2013
    Co-Authors: Jules Beekwilder, Katarina Cankar, Adele Van Houwelingen, Theo Sonke, Harro J Bouwmeester, René M. De Jong, Aalt D. J. Van Dijk, Geert Stoopen, Jihane Achkar, Dirk Bosch
    Abstract:

    Summary Nootkatone is one of the major terpenes in the heartwood of the Nootka cypress Callitropsis nootkatensis. It is an oxidized sesquiterpene, which has been postulated to be derived from Valencene. Both Valencene and nootkatone are used for flavouring citrus beverages and are considered among the most valuable terpenes used at commercial scale. Functional evaluation of putative terpene synthase genes sourced by large-scale EST sequencing from Nootka cypress wood revealed a Valencene synthase gene (CnVS). CnVS expression in different tissues from the tree correlates well with nootkatone content, suggesting that CnVS represents the first dedicated gene in the nootkatone biosynthetic pathway in C. nootkatensis The gene belongs to the gymnosperm-specific TPS-d subfamily of terpenes synthases and its protein sequence has low similarity to known citrus Valencene synthases. In vitro, CnVS displays high robustness under different pH and temperature regimes, potentially beneficial properties for application in different host and physiological conditions. Biotechnological production of sesquiterpenes has been shown to be feasible, but productivity of microbial strains expressing Valencene synthase from Citrus is low, indicating that optimization of Valencene synthase activity is needed. Indeed, expression of CnVS in Saccharomyces cerevisiae indicated potential for higher yields. In an optimized Rhodobacter sphaeroides strain, expression of CnVS increased Valencene yields 14-fold to 352 mg/L, bringing production to levels with industrial potential.

  • a chicory cytochrome p450 mono oxygenase cyp71av8 for the oxidation of Valencene
    FEBS Letters, 2011
    Co-Authors: Katarina Cankar, Adele Van Houwelingen, Dirk Bosch, Theo Sonke, Harro J Bouwmeester, Jules Beekwilder
    Abstract:

    Chicory (Cichorium intybus L.), which is known to have a variety of terpene-hydroxylating activities, was screened for a P450 mono-oxygenase to convert (+)-Valencene to (+)-nootkatone. A novel P450 cDNA was identified in a chicory root EST library. Co-expression of the enzyme with a Valencene synthase in yeast, led to formation of trans-nootkatol, cis-nootkatol and (+)-nootkatone. The novel enzyme was also found to catalyse a three step conversion of germacrene A to germacra-1(10),4,11(13)-trien-12-oic acid, indicating its involvement in chicory sesquiterpene lactone biosynthesis. Likewise, amorpha-4,11-diene was converted to artemisinic acid. Surprisingly, the chicory P450 has a different regio-specificity on (+)-Valencene compared to germacrene A and amorpha-4,11-diene.