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valencene  (Toronto Research Chemicals)


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    Structured Review

    Toronto Research Chemicals valencene
    Sesquiterpene synthases (STPS) and cytochrome P450 enzymes (CYPs) were targeted to the algal chloroplast. Each STPS construct included C-terminal ScErg20 FPPS, while CYPs were co-expressed through plastid targeting and without transmembrane domains. (A) GC-MS chromatograms of dodecane extracts from C. reinhardtii strains expressing plastid localized STPS and CYP combinations, numbers indicate specific compounds identified by MS. (B) Quantitative analysis of sesquiterpenoid production based on GC-FID data. Circles: sum of peak areas for sesquiterpenoids; triangles: sum of peak areas for modified sesquiterpenoids. Data represent mean ± SD (n=12, 4 transformants × 3 biological replicates). (C) Functionalization efficiency (%) of each CYP, calculated as the fraction of functionalized sesquiterpenoids from total sesquiterpenoids. Circles represent individual transformants. Compounds: [1] Aristolene, [2] Aristolochene, [3] Aristolochone, [4] <t>Valencene,</t> [5] Nootkatone, [6] α-Santalene, [7] Bergamotol, [8] Santalol, [9] α-Cadinene, [10] δ-Cadinene, [11] β-Cadinene, [12] Muurolene, [13] Muurolol, [14] τ-Cadinol, [15] α-Guaiene, [16] β-Guaiene, [17] α-Humulene, [18] δ-Guaiene, [19] Alloaromadendrene, [20] α-Guaiol, [21] β-Guaiol, [22] Globulol, [23] Rotundone, [24] Alloaromadendrene oxide. GC-MS/FID data in SI Appendix File S5, Tables S3, and Fig. S6–S7.
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    1) Product Images from "Compartmentalized sesquiterpenoid biosynthesis and functionalization in the Chlamydomonas reinhardtii plastid"

    Article Title: Compartmentalized sesquiterpenoid biosynthesis and functionalization in the Chlamydomonas reinhardtii plastid

    Journal: bioRxiv

    doi: 10.1101/2024.08.21.608953

    Sesquiterpene synthases (STPS) and cytochrome P450 enzymes (CYPs) were targeted to the algal chloroplast. Each STPS construct included C-terminal ScErg20 FPPS, while CYPs were co-expressed through plastid targeting and without transmembrane domains. (A) GC-MS chromatograms of dodecane extracts from C. reinhardtii strains expressing plastid localized STPS and CYP combinations, numbers indicate specific compounds identified by MS. (B) Quantitative analysis of sesquiterpenoid production based on GC-FID data. Circles: sum of peak areas for sesquiterpenoids; triangles: sum of peak areas for modified sesquiterpenoids. Data represent mean ± SD (n=12, 4 transformants × 3 biological replicates). (C) Functionalization efficiency (%) of each CYP, calculated as the fraction of functionalized sesquiterpenoids from total sesquiterpenoids. Circles represent individual transformants. Compounds: [1] Aristolene, [2] Aristolochene, [3] Aristolochone, [4] Valencene, [5] Nootkatone, [6] α-Santalene, [7] Bergamotol, [8] Santalol, [9] α-Cadinene, [10] δ-Cadinene, [11] β-Cadinene, [12] Muurolene, [13] Muurolol, [14] τ-Cadinol, [15] α-Guaiene, [16] β-Guaiene, [17] α-Humulene, [18] δ-Guaiene, [19] Alloaromadendrene, [20] α-Guaiol, [21] β-Guaiol, [22] Globulol, [23] Rotundone, [24] Alloaromadendrene oxide. GC-MS/FID data in SI Appendix File S5, Tables S3, and Fig. S6–S7.
    Figure Legend Snippet: Sesquiterpene synthases (STPS) and cytochrome P450 enzymes (CYPs) were targeted to the algal chloroplast. Each STPS construct included C-terminal ScErg20 FPPS, while CYPs were co-expressed through plastid targeting and without transmembrane domains. (A) GC-MS chromatograms of dodecane extracts from C. reinhardtii strains expressing plastid localized STPS and CYP combinations, numbers indicate specific compounds identified by MS. (B) Quantitative analysis of sesquiterpenoid production based on GC-FID data. Circles: sum of peak areas for sesquiterpenoids; triangles: sum of peak areas for modified sesquiterpenoids. Data represent mean ± SD (n=12, 4 transformants × 3 biological replicates). (C) Functionalization efficiency (%) of each CYP, calculated as the fraction of functionalized sesquiterpenoids from total sesquiterpenoids. Circles represent individual transformants. Compounds: [1] Aristolene, [2] Aristolochene, [3] Aristolochone, [4] Valencene, [5] Nootkatone, [6] α-Santalene, [7] Bergamotol, [8] Santalol, [9] α-Cadinene, [10] δ-Cadinene, [11] β-Cadinene, [12] Muurolene, [13] Muurolol, [14] τ-Cadinol, [15] α-Guaiene, [16] β-Guaiene, [17] α-Humulene, [18] δ-Guaiene, [19] Alloaromadendrene, [20] α-Guaiol, [21] β-Guaiol, [22] Globulol, [23] Rotundone, [24] Alloaromadendrene oxide. GC-MS/FID data in SI Appendix File S5, Tables S3, and Fig. S6–S7.

    Techniques Used: Construct, Gas Chromatography-Mass Spectrometry, Expressing, Modification

    Illustration of sesquiterpenoid chemical structures identified in this work. Colored sections depict distinct sesquiterpenoid classes produced through the action of specific sesquiterpene synthases and cytochrome P450 enzymes. Compounds are labeled with unique identifiers corresponding to their structures: Aristolene [01], Aristolochene [02], Aristolochone [03], Valencene [04], Nootkatone [05], α-Santalene [06], Bergamotol [07], Santalol [08], α-Cadinene [09], δ-Cadinene [10], β-Cadinene [11], Muurolene [12], Muurolol [13], τ-Cadinol [14], α-Guaiene [15], β-Guaiene [16], α-Humulene [17], δ-Guaiene [18], Alloaromadendrene [19], α-Guaiol [20], β-Guaiol [21], Globulol [22], Rotundone [23], and Alloaromadendrene oxide [24]. GC-MS/FID data in SI Appendix File S5, Tables S7–S8 .
    Figure Legend Snippet: Illustration of sesquiterpenoid chemical structures identified in this work. Colored sections depict distinct sesquiterpenoid classes produced through the action of specific sesquiterpene synthases and cytochrome P450 enzymes. Compounds are labeled with unique identifiers corresponding to their structures: Aristolene [01], Aristolochene [02], Aristolochone [03], Valencene [04], Nootkatone [05], α-Santalene [06], Bergamotol [07], Santalol [08], α-Cadinene [09], δ-Cadinene [10], β-Cadinene [11], Muurolene [12], Muurolol [13], τ-Cadinol [14], α-Guaiene [15], β-Guaiene [16], α-Humulene [17], δ-Guaiene [18], Alloaromadendrene [19], α-Guaiol [20], β-Guaiol [21], Globulol [22], Rotundone [23], and Alloaromadendrene oxide [24]. GC-MS/FID data in SI Appendix File S5, Tables S7–S8 .

    Techniques Used: Produced, Labeling, Gas Chromatography-Mass Spectrometry

    GC-MS/FID analysis of dodecane overlay samples for sesquiterpenoid species accumulated by C. reinhardtii expressing different STPSs (B02, B03, B06, B08, B09) and corresponding cytochrome P450s (CYP02, CYP05, CYP09, CYP10, CYP12) when cultivated with three carbon source conditions: CO₂, acetate, or CO₂+acetate. Black dots represent sesquiterpenoid compounds; black triangles indicate functionalized derivatives. Relative abundance plots quantify production levels under each condition. (A) Aristolochene synthase (B02) + CYP02; (B) Valencene synthase (B03) + CYP05; (C) Santalene synthase (B06) + CYP09; (D) Cadinol synthase (B08) + CYP10; (E) Guaiene synthase (B09) + CYP12. For each panel, chromatograms (left) show product retention times; bar graphs (right) depict relative abundance. GC-MS/FID data in SI Appendix File S6, Tables S6–S8.
    Figure Legend Snippet: GC-MS/FID analysis of dodecane overlay samples for sesquiterpenoid species accumulated by C. reinhardtii expressing different STPSs (B02, B03, B06, B08, B09) and corresponding cytochrome P450s (CYP02, CYP05, CYP09, CYP10, CYP12) when cultivated with three carbon source conditions: CO₂, acetate, or CO₂+acetate. Black dots represent sesquiterpenoid compounds; black triangles indicate functionalized derivatives. Relative abundance plots quantify production levels under each condition. (A) Aristolochene synthase (B02) + CYP02; (B) Valencene synthase (B03) + CYP05; (C) Santalene synthase (B06) + CYP09; (D) Cadinol synthase (B08) + CYP10; (E) Guaiene synthase (B09) + CYP12. For each panel, chromatograms (left) show product retention times; bar graphs (right) depict relative abundance. GC-MS/FID data in SI Appendix File S6, Tables S6–S8.

    Techniques Used: Gas Chromatography-Mass Spectrometry, Expressing



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    Sesquiterpene synthases (STPS) and cytochrome P450 enzymes (CYPs) were targeted to the algal chloroplast. Each STPS construct included C-terminal ScErg20 FPPS, while CYPs were co-expressed through plastid targeting and without transmembrane domains. (A) GC-MS chromatograms of dodecane extracts from C. reinhardtii strains expressing plastid localized STPS and CYP combinations, numbers indicate specific compounds identified by MS. (B) Quantitative analysis of sesquiterpenoid production based on GC-FID data. Circles: sum of peak areas for sesquiterpenoids; triangles: sum of peak areas for modified sesquiterpenoids. Data represent mean ± SD (n=12, 4 transformants × 3 biological replicates). (C) Functionalization efficiency (%) of each CYP, calculated as the fraction of functionalized sesquiterpenoids from total sesquiterpenoids. Circles represent individual transformants. Compounds: [1] Aristolene, [2] Aristolochene, [3] Aristolochone, [4] Valencene, [5] Nootkatone, [6] α-Santalene, [7] Bergamotol, [8] Santalol, [9] α-Cadinene, [10] δ-Cadinene, [11] β-Cadinene, [12] Muurolene, [13] Muurolol, [14] τ-Cadinol, [15] α-Guaiene, [16] β-Guaiene, [17] α-Humulene, [18] δ-Guaiene, [19] Alloaromadendrene, [20] α-Guaiol, [21] β-Guaiol, [22] Globulol, [23] Rotundone, [24] Alloaromadendrene oxide. GC-MS/FID data in SI Appendix File S5, Tables S3, and Fig. S6–S7.

    Journal: bioRxiv

    Article Title: Compartmentalized sesquiterpenoid biosynthesis and functionalization in the Chlamydomonas reinhardtii plastid

    doi: 10.1101/2024.08.21.608953

    Figure Lengend Snippet: Sesquiterpene synthases (STPS) and cytochrome P450 enzymes (CYPs) were targeted to the algal chloroplast. Each STPS construct included C-terminal ScErg20 FPPS, while CYPs were co-expressed through plastid targeting and without transmembrane domains. (A) GC-MS chromatograms of dodecane extracts from C. reinhardtii strains expressing plastid localized STPS and CYP combinations, numbers indicate specific compounds identified by MS. (B) Quantitative analysis of sesquiterpenoid production based on GC-FID data. Circles: sum of peak areas for sesquiterpenoids; triangles: sum of peak areas for modified sesquiterpenoids. Data represent mean ± SD (n=12, 4 transformants × 3 biological replicates). (C) Functionalization efficiency (%) of each CYP, calculated as the fraction of functionalized sesquiterpenoids from total sesquiterpenoids. Circles represent individual transformants. Compounds: [1] Aristolene, [2] Aristolochene, [3] Aristolochone, [4] Valencene, [5] Nootkatone, [6] α-Santalene, [7] Bergamotol, [8] Santalol, [9] α-Cadinene, [10] δ-Cadinene, [11] β-Cadinene, [12] Muurolene, [13] Muurolol, [14] τ-Cadinol, [15] α-Guaiene, [16] β-Guaiene, [17] α-Humulene, [18] δ-Guaiene, [19] Alloaromadendrene, [20] α-Guaiol, [21] β-Guaiol, [22] Globulol, [23] Rotundone, [24] Alloaromadendrene oxide. GC-MS/FID data in SI Appendix File S5, Tables S3, and Fig. S6–S7.

    Article Snippet: For quantification, we used calibration curves (1 – 500 μM) of purified standards in dodecane or FCs: δ-guaiene, patchoulol, α-santalene, valerianol, α-bisabolol, valencene, and cedrene (Toronto Research Chemicals, Canada) ( SI Appendix, Fig. S5 ).

    Techniques: Construct, Gas Chromatography-Mass Spectrometry, Expressing, Modification

    Illustration of sesquiterpenoid chemical structures identified in this work. Colored sections depict distinct sesquiterpenoid classes produced through the action of specific sesquiterpene synthases and cytochrome P450 enzymes. Compounds are labeled with unique identifiers corresponding to their structures: Aristolene [01], Aristolochene [02], Aristolochone [03], Valencene [04], Nootkatone [05], α-Santalene [06], Bergamotol [07], Santalol [08], α-Cadinene [09], δ-Cadinene [10], β-Cadinene [11], Muurolene [12], Muurolol [13], τ-Cadinol [14], α-Guaiene [15], β-Guaiene [16], α-Humulene [17], δ-Guaiene [18], Alloaromadendrene [19], α-Guaiol [20], β-Guaiol [21], Globulol [22], Rotundone [23], and Alloaromadendrene oxide [24]. GC-MS/FID data in SI Appendix File S5, Tables S7–S8 .

    Journal: bioRxiv

    Article Title: Compartmentalized sesquiterpenoid biosynthesis and functionalization in the Chlamydomonas reinhardtii plastid

    doi: 10.1101/2024.08.21.608953

    Figure Lengend Snippet: Illustration of sesquiterpenoid chemical structures identified in this work. Colored sections depict distinct sesquiterpenoid classes produced through the action of specific sesquiterpene synthases and cytochrome P450 enzymes. Compounds are labeled with unique identifiers corresponding to their structures: Aristolene [01], Aristolochene [02], Aristolochone [03], Valencene [04], Nootkatone [05], α-Santalene [06], Bergamotol [07], Santalol [08], α-Cadinene [09], δ-Cadinene [10], β-Cadinene [11], Muurolene [12], Muurolol [13], τ-Cadinol [14], α-Guaiene [15], β-Guaiene [16], α-Humulene [17], δ-Guaiene [18], Alloaromadendrene [19], α-Guaiol [20], β-Guaiol [21], Globulol [22], Rotundone [23], and Alloaromadendrene oxide [24]. GC-MS/FID data in SI Appendix File S5, Tables S7–S8 .

    Article Snippet: For quantification, we used calibration curves (1 – 500 μM) of purified standards in dodecane or FCs: δ-guaiene, patchoulol, α-santalene, valerianol, α-bisabolol, valencene, and cedrene (Toronto Research Chemicals, Canada) ( SI Appendix, Fig. S5 ).

    Techniques: Produced, Labeling, Gas Chromatography-Mass Spectrometry

    GC-MS/FID analysis of dodecane overlay samples for sesquiterpenoid species accumulated by C. reinhardtii expressing different STPSs (B02, B03, B06, B08, B09) and corresponding cytochrome P450s (CYP02, CYP05, CYP09, CYP10, CYP12) when cultivated with three carbon source conditions: CO₂, acetate, or CO₂+acetate. Black dots represent sesquiterpenoid compounds; black triangles indicate functionalized derivatives. Relative abundance plots quantify production levels under each condition. (A) Aristolochene synthase (B02) + CYP02; (B) Valencene synthase (B03) + CYP05; (C) Santalene synthase (B06) + CYP09; (D) Cadinol synthase (B08) + CYP10; (E) Guaiene synthase (B09) + CYP12. For each panel, chromatograms (left) show product retention times; bar graphs (right) depict relative abundance. GC-MS/FID data in SI Appendix File S6, Tables S6–S8.

    Journal: bioRxiv

    Article Title: Compartmentalized sesquiterpenoid biosynthesis and functionalization in the Chlamydomonas reinhardtii plastid

    doi: 10.1101/2024.08.21.608953

    Figure Lengend Snippet: GC-MS/FID analysis of dodecane overlay samples for sesquiterpenoid species accumulated by C. reinhardtii expressing different STPSs (B02, B03, B06, B08, B09) and corresponding cytochrome P450s (CYP02, CYP05, CYP09, CYP10, CYP12) when cultivated with three carbon source conditions: CO₂, acetate, or CO₂+acetate. Black dots represent sesquiterpenoid compounds; black triangles indicate functionalized derivatives. Relative abundance plots quantify production levels under each condition. (A) Aristolochene synthase (B02) + CYP02; (B) Valencene synthase (B03) + CYP05; (C) Santalene synthase (B06) + CYP09; (D) Cadinol synthase (B08) + CYP10; (E) Guaiene synthase (B09) + CYP12. For each panel, chromatograms (left) show product retention times; bar graphs (right) depict relative abundance. GC-MS/FID data in SI Appendix File S6, Tables S6–S8.

    Article Snippet: For quantification, we used calibration curves (1 – 500 μM) of purified standards in dodecane or FCs: δ-guaiene, patchoulol, α-santalene, valerianol, α-bisabolol, valencene, and cedrene (Toronto Research Chemicals, Canada) ( SI Appendix, Fig. S5 ).

    Techniques: Gas Chromatography-Mass Spectrometry, Expressing

    Chemical structure of valencene and nootkatone, and the biosynthesis pathway. (A) Chemical structure of valencene, (+)-nootkatone, (−)-nootkatone. (B) The biosynthesis pathway of valencene, nootkatone and different types of terpenoids. Metabolite abbreviations: IPP, Isopentenyl pyrophosphate; DMAPP, Dimethylallyl pyrophosphate; GPP, Geranyl pyrophosphate; FPP, Farnesyl pyrophosphate; GGPP, Geranylgeranyl pyrophosphate; HEPP, Heptaprenyl pyrophosphate; UDPP, Undecaprenyl pyrophosphate. Solid lines represent reactions being catalyzed by specific enzymes in one-step, and dashed lines represent reactions being catalyzed by different enzymes or in multiple steps.

    Journal: Frontiers in Microbiology

    Article Title: Application of valencene and prospects for its production in engineered microorganisms

    doi: 10.3389/fmicb.2024.1444099

    Figure Lengend Snippet: Chemical structure of valencene and nootkatone, and the biosynthesis pathway. (A) Chemical structure of valencene, (+)-nootkatone, (−)-nootkatone. (B) The biosynthesis pathway of valencene, nootkatone and different types of terpenoids. Metabolite abbreviations: IPP, Isopentenyl pyrophosphate; DMAPP, Dimethylallyl pyrophosphate; GPP, Geranyl pyrophosphate; FPP, Farnesyl pyrophosphate; GGPP, Geranylgeranyl pyrophosphate; HEPP, Heptaprenyl pyrophosphate; UDPP, Undecaprenyl pyrophosphate. Solid lines represent reactions being catalyzed by specific enzymes in one-step, and dashed lines represent reactions being catalyzed by different enzymes or in multiple steps.

    Article Snippet: Likewise, the USA biotechnology company Evolva can also provide consistent quality valencene with up to 94% purity (meets the EU Flavor regulation) via sustainable fermentation, which was historically unavailable because of technical restrictions.

    Techniques:

    Engineered microorganisms and plants for the production of valencene. Some important advantages of these hosts for the biosynthesis of terpenoids were listed. To highlight the features of photosynthetic bacteria and yeast, they were listed separately with bacteria and fungi, respectively.

    Journal: Frontiers in Microbiology

    Article Title: Application of valencene and prospects for its production in engineered microorganisms

    doi: 10.3389/fmicb.2024.1444099

    Figure Lengend Snippet: Engineered microorganisms and plants for the production of valencene. Some important advantages of these hosts for the biosynthesis of terpenoids were listed. To highlight the features of photosynthetic bacteria and yeast, they were listed separately with bacteria and fungi, respectively.

    Article Snippet: Likewise, the USA biotechnology company Evolva can also provide consistent quality valencene with up to 94% purity (meets the EU Flavor regulation) via sustainable fermentation, which was historically unavailable because of technical restrictions.

    Techniques: Bacteria

    Main engineering strategies for improved production of valencene in microorganisms and plants.

    Journal: Frontiers in Microbiology

    Article Title: Application of valencene and prospects for its production in engineered microorganisms

    doi: 10.3389/fmicb.2024.1444099

    Figure Lengend Snippet: Main engineering strategies for improved production of valencene in microorganisms and plants.

    Article Snippet: Likewise, the USA biotechnology company Evolva can also provide consistent quality valencene with up to 94% purity (meets the EU Flavor regulation) via sustainable fermentation, which was historically unavailable because of technical restrictions.

    Techniques: Selection, Expressing, Control, Mutagenesis, Knock-Out, In Situ, Over Expression, Knockdown, Modification, Plasmid Preparation, Sequencing

    Engineering strategies used to improve the production of valencene in yeast. (A) Overexpressing rate-limiting enzymes of the MVA pathway. (B) Employing different MVA pathways to reconstruct the biosynthetic pathway of valencene in peroxisomes of yeast. The detailed information of different MVA can be obtained from . (C) Decreasing the competing pathways of valencene by knockout nonessential genes or knockdown essential genes in branch pathways. (D) Engineering of valencene synthase to improve valencene production by selecting suitable valencene synthases from different origins, creating mutants with high catalytic efficiency or increased product specificity, constructing fusion proteins with various linkers, and fine-tuning the expression levels of valencene synthases. (E) Compartmentalization strategies for improving synthesis of valencene: expressing valencene synthases in mitochondria by fusing the mitochondrial targeting signal peptide and reconstructing the valencene synthesis pathway in the peroxisome of yeast. (F) Improving valencene production by engineering the global regulation of yeast and optimizing the fermentation process.

    Journal: Frontiers in Microbiology

    Article Title: Application of valencene and prospects for its production in engineered microorganisms

    doi: 10.3389/fmicb.2024.1444099

    Figure Lengend Snippet: Engineering strategies used to improve the production of valencene in yeast. (A) Overexpressing rate-limiting enzymes of the MVA pathway. (B) Employing different MVA pathways to reconstruct the biosynthetic pathway of valencene in peroxisomes of yeast. The detailed information of different MVA can be obtained from . (C) Decreasing the competing pathways of valencene by knockout nonessential genes or knockdown essential genes in branch pathways. (D) Engineering of valencene synthase to improve valencene production by selecting suitable valencene synthases from different origins, creating mutants with high catalytic efficiency or increased product specificity, constructing fusion proteins with various linkers, and fine-tuning the expression levels of valencene synthases. (E) Compartmentalization strategies for improving synthesis of valencene: expressing valencene synthases in mitochondria by fusing the mitochondrial targeting signal peptide and reconstructing the valencene synthesis pathway in the peroxisome of yeast. (F) Improving valencene production by engineering the global regulation of yeast and optimizing the fermentation process.

    Article Snippet: Likewise, the USA biotechnology company Evolva can also provide consistent quality valencene with up to 94% purity (meets the EU Flavor regulation) via sustainable fermentation, which was historically unavailable because of technical restrictions.

    Techniques: Knock-Out, Knockdown, Expressing