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Christopher G Jones - One of the best experts on this subject based on the ideXlab platform.
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sesquiterpene variation in west australian Sandalwood santalum spicatum
Molecules, 2017Co-Authors: Jessie Moniodis, Christopher G Jones, Emilio L Ghisalberti, Julie A Plummer, Michael Renton, Liz E Barbour, Joerg BohlmannAbstract:West Australian Sandalwood (Santalum spicatum) has long been exploited for its fragrant, sesquiterpene-rich heartwood; however Sandalwood fragrance qualities vary substantially, which is of interest to the Sandalwood industry. We investigated metabolite profiles of trees from the arid northern and southeastern and semi-arid southwestern regions of West Australia for patterns in composition and co-occurrence of sesquiterpenes. Total sesquiterpene content was similar across the entire sample collection; however sesquiterpene composition was highly variable. Northern populations contained the highest levels of desirable fragrance compounds, α- and β-santalol, as did individuals from the southwest. Southeastern populations were higher in E,E-farnesol, an undesired allergenic constituent, and low in santalols. These trees generally also contained higher levels of α-bisabolol. E,E-farnesol co-occurred with dendrolasin. Contrasting α-santalol and E,E-farnesol chemotypes revealed potential for future genetic tree improvement. Although chemical variation was evident both within and among regions, variation was generally lower within regions. Our results showed distinct patterns in chemical diversity of S. spicatum across its natural distribution, consistent with earlier investigations into Sandalwood population genetics. These results are relevant for plantation tree improvement and conservation efforts.
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the transcriptome of sesquiterpenoid biosynthesis in heartwood xylem of western australian Sandalwood santalum spicatum
Phytochemistry, 2015Co-Authors: Christopher G Jones, Emilio L Ghisalberti, Julie A Plummer, Jessie Moniodis, Liz E Barbour, Joerg BohlmannAbstract:The fragrant heartwood oil of West Australian Sandalwood (Santalum spicatum) contains a mixture of sesquiterpene olefins and alcohols, including variable levels of the valuable sesquiterpene alcohols, α- and β-santalol, and often high levels of E,E-farnesol. Transcriptome analysis revealed sequences for a nearly complete set of genes of the sesquiterpenoid biosynthetic pathway in this commercially valuable Sandalwood species. Transcriptome sequences were produced from heartwood xylem tissue of a farnesol-rich individual tree. From the assembly of 12,537 contigs, seven different terpene synthases (TPSs), several cytochromes P450, and allylic phosphatases were identified, as well as transcripts of the mevalonic acid and methylerythritol phosphate pathways. Five of the S. spicatum TPS sequences were previously unknown. The full-length cDNA of SspiTPS4 was cloned and the enzyme functionally characterized as a multi-product sesquisabinene B synthase, which complements previous characterization of santalene and bisabolol synthases in S. spicatum. While SspiTPS4 and previously cloned Sandalwood TPSs do not explain the prevalence of E,E-farnesol in S. spicatum, the genes identified in this and previous work can form a basis for future studies on natural variation of Sandalwood terpenoid oil profiles.
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biosynthesis of Sandalwood oil santalum album cyp76f cytochromes p450 produce santalols and bergamotol
PLOS ONE, 2013Co-Authors: Maria L Diazchavez, Christopher G Jones, Christopher I Keeling, Emilio L Ghisalberti, Elizabeth L Barbour, Julie A Plummer, Lufiani L Madilao, Jessie Moniodis, Sharon Jancsik, Jorg BohlmannAbstract:Sandalwood oil is one of the world’s most highly prized essential oils, appearing in many high-end perfumes and fragrances. Extracted from the mature heartwood of several Santalum species, Sandalwood oil is comprised mainly of sesquiterpene olefins and alcohols. Four sesquiterpenols, α-, β-, and epi-β-santalol and α-exo-bergamotol, make up approximately 90% of the oil of Santalum album. These compounds are the hydroxylated analogues of α-, β-, and epi-β-santalene and α-exo-bergamotene. By mining a transcriptome database of S. album for candidate cytochrome P450 genes, we cloned and characterized cDNAs encoding a small family of ten cytochrome P450-dependent monooxygenases annotated as SaCYP76F37v1, SaCYP76F37v2, SaCYP76F38v1, SaCYP76F38v2, SaCYP76F39v1, SaCYP76F39v2, SaCYP76F40, SaCYP76F41, SaCYP76F42, and SaCYP76F43. Nine of these genes were functionally characterized using in vitro assays and yeast in vivo assays to encode santalene/bergamotene oxidases and bergamotene oxidases. These results provide a foundation for production of Sandalwood oil for the fragrance industry by means of metabolic engineering, as demonstrated with proof-of-concept formation of santalols and bergamotol in engineered yeast cells, simultaneously addressing conservation challenges by reducing pressure on supply of Sandalwood from native forests.
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isolation of cdnas and functional characterisation of two multi product terpene synthase enzymes from Sandalwood santalum album l
Archives of Biochemistry and Biophysics, 2008Co-Authors: Christopher G Jones, Christopher I Keeling, Emilio L Ghisalberti, Elizabeth L Barbour, Julie A Plummer, Jorg BohlmannAbstract:Abstract Sandalwood, Santalum album (Santalaceae) is a small hemi-parasitic tropical tree of great economic value. Sandalwood timber contains resins and essential oils, particularly the santalols, santalenes and dozens of other minor sesquiterpenoids. These sesquiterpenoids provide the unique Sandalwood fragrance. The research described in this paper set out to identify genes involved in essential oil biosynthesis, particularly terpene synthases (TPS) in S. album, with the long-term aim of better understanding heartwood oil production. Degenerate TPS primers amplified two genomic TPS fragments from S. album, one of which enabled the isolation of two TPS cDNAs, SamonoTPS1 (1731 bp) and SasesquiTPS1 (1680 bp). Both translated protein sequences shared highest similarity with known TPS from grapevine (Vitis vinifera). Heterologous expression in Escherichia coli produced catalytically active proteins. SamonoTPS1 was identified as a monoterpene synthase which produced a mixture of (+)-α-terpineol and (−)-limonene, along with small quantities of linalool, myrcene, (−)-α-pinene, (+)-sabinene and geraniol when assayed with geranyl diphosphate. Sesquiterpene synthase SasesquiTPS1 produced the monocyclic sesquiterpene alcohol germacrene D-4-ol and helminthogermacrene, when incubated with farnesyl diphosphate. Also present were α-bulnesene, γ-muurolene, α- and β-selinenes, as well as several other minor bicyclic compounds. Although these sesquiterpenes are present in only minute quantities in the distilled Sandalwood oil, the genes and their encoded enzymes described here represent the first TPS isolated and characterised from a member of the Santalaceae plant family and they may enable the future discovery of additional TPS genes in Sandalwood.
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quantitative co occurrence of sesquiterpenes a tool for elucidating their biosynthesis in indian Sandalwood santalum album
Phytochemistry, 2006Co-Authors: Christopher G Jones, Emilio L Ghisalberti, Julie A Plummer, Elizabeth L BarbourAbstract:Abstract A chemotaxonomic approach was used to investigate biosynthetic relationships between heartwood sesquiterpenes in Indian Sandalwood, Santalum album L. Strong, linear relationships exist between four structural classes of sesquiterpenes; α- and β-santalenes and bergamotene; γ- and β-curcumene; β-bisabolene and α-bisabolol and four unidentified sesquiterpenes. All samples within the heartwood yielded the same co-occurrence patterns, however wood from young trees tended to be more variable. It is proposed that the biosynthesis of each structural class of sesquiterpene in Sandalwood oil is linked through common carbocation intermediates. Lack of co-occurrence between each structural class suggests that four separate cyclase enzymes may be operative. The biosynthesis of Sandalwood oil sesquiterpenes is discussed with respect to these co-occurrence patterns. Extractable oil yield was correlated to heartwood content of each wood core and the oil composition did not vary significantly throughout the tree.
Emilio L Ghisalberti - One of the best experts on this subject based on the ideXlab platform.
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sesquiterpene variation in west australian Sandalwood santalum spicatum
Molecules, 2017Co-Authors: Jessie Moniodis, Christopher G Jones, Emilio L Ghisalberti, Julie A Plummer, Michael Renton, Liz E Barbour, Joerg BohlmannAbstract:West Australian Sandalwood (Santalum spicatum) has long been exploited for its fragrant, sesquiterpene-rich heartwood; however Sandalwood fragrance qualities vary substantially, which is of interest to the Sandalwood industry. We investigated metabolite profiles of trees from the arid northern and southeastern and semi-arid southwestern regions of West Australia for patterns in composition and co-occurrence of sesquiterpenes. Total sesquiterpene content was similar across the entire sample collection; however sesquiterpene composition was highly variable. Northern populations contained the highest levels of desirable fragrance compounds, α- and β-santalol, as did individuals from the southwest. Southeastern populations were higher in E,E-farnesol, an undesired allergenic constituent, and low in santalols. These trees generally also contained higher levels of α-bisabolol. E,E-farnesol co-occurred with dendrolasin. Contrasting α-santalol and E,E-farnesol chemotypes revealed potential for future genetic tree improvement. Although chemical variation was evident both within and among regions, variation was generally lower within regions. Our results showed distinct patterns in chemical diversity of S. spicatum across its natural distribution, consistent with earlier investigations into Sandalwood population genetics. These results are relevant for plantation tree improvement and conservation efforts.
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the transcriptome of sesquiterpenoid biosynthesis in heartwood xylem of western australian Sandalwood santalum spicatum
Phytochemistry, 2015Co-Authors: Christopher G Jones, Emilio L Ghisalberti, Julie A Plummer, Jessie Moniodis, Liz E Barbour, Joerg BohlmannAbstract:The fragrant heartwood oil of West Australian Sandalwood (Santalum spicatum) contains a mixture of sesquiterpene olefins and alcohols, including variable levels of the valuable sesquiterpene alcohols, α- and β-santalol, and often high levels of E,E-farnesol. Transcriptome analysis revealed sequences for a nearly complete set of genes of the sesquiterpenoid biosynthetic pathway in this commercially valuable Sandalwood species. Transcriptome sequences were produced from heartwood xylem tissue of a farnesol-rich individual tree. From the assembly of 12,537 contigs, seven different terpene synthases (TPSs), several cytochromes P450, and allylic phosphatases were identified, as well as transcripts of the mevalonic acid and methylerythritol phosphate pathways. Five of the S. spicatum TPS sequences were previously unknown. The full-length cDNA of SspiTPS4 was cloned and the enzyme functionally characterized as a multi-product sesquisabinene B synthase, which complements previous characterization of santalene and bisabolol synthases in S. spicatum. While SspiTPS4 and previously cloned Sandalwood TPSs do not explain the prevalence of E,E-farnesol in S. spicatum, the genes identified in this and previous work can form a basis for future studies on natural variation of Sandalwood terpenoid oil profiles.
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biosynthesis of Sandalwood oil santalum album cyp76f cytochromes p450 produce santalols and bergamotol
PLOS ONE, 2013Co-Authors: Maria L Diazchavez, Christopher G Jones, Christopher I Keeling, Emilio L Ghisalberti, Elizabeth L Barbour, Julie A Plummer, Lufiani L Madilao, Jessie Moniodis, Sharon Jancsik, Jorg BohlmannAbstract:Sandalwood oil is one of the world’s most highly prized essential oils, appearing in many high-end perfumes and fragrances. Extracted from the mature heartwood of several Santalum species, Sandalwood oil is comprised mainly of sesquiterpene olefins and alcohols. Four sesquiterpenols, α-, β-, and epi-β-santalol and α-exo-bergamotol, make up approximately 90% of the oil of Santalum album. These compounds are the hydroxylated analogues of α-, β-, and epi-β-santalene and α-exo-bergamotene. By mining a transcriptome database of S. album for candidate cytochrome P450 genes, we cloned and characterized cDNAs encoding a small family of ten cytochrome P450-dependent monooxygenases annotated as SaCYP76F37v1, SaCYP76F37v2, SaCYP76F38v1, SaCYP76F38v2, SaCYP76F39v1, SaCYP76F39v2, SaCYP76F40, SaCYP76F41, SaCYP76F42, and SaCYP76F43. Nine of these genes were functionally characterized using in vitro assays and yeast in vivo assays to encode santalene/bergamotene oxidases and bergamotene oxidases. These results provide a foundation for production of Sandalwood oil for the fragrance industry by means of metabolic engineering, as demonstrated with proof-of-concept formation of santalols and bergamotol in engineered yeast cells, simultaneously addressing conservation challenges by reducing pressure on supply of Sandalwood from native forests.
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isolation of cdnas and functional characterisation of two multi product terpene synthase enzymes from Sandalwood santalum album l
Archives of Biochemistry and Biophysics, 2008Co-Authors: Christopher G Jones, Christopher I Keeling, Emilio L Ghisalberti, Elizabeth L Barbour, Julie A Plummer, Jorg BohlmannAbstract:Abstract Sandalwood, Santalum album (Santalaceae) is a small hemi-parasitic tropical tree of great economic value. Sandalwood timber contains resins and essential oils, particularly the santalols, santalenes and dozens of other minor sesquiterpenoids. These sesquiterpenoids provide the unique Sandalwood fragrance. The research described in this paper set out to identify genes involved in essential oil biosynthesis, particularly terpene synthases (TPS) in S. album, with the long-term aim of better understanding heartwood oil production. Degenerate TPS primers amplified two genomic TPS fragments from S. album, one of which enabled the isolation of two TPS cDNAs, SamonoTPS1 (1731 bp) and SasesquiTPS1 (1680 bp). Both translated protein sequences shared highest similarity with known TPS from grapevine (Vitis vinifera). Heterologous expression in Escherichia coli produced catalytically active proteins. SamonoTPS1 was identified as a monoterpene synthase which produced a mixture of (+)-α-terpineol and (−)-limonene, along with small quantities of linalool, myrcene, (−)-α-pinene, (+)-sabinene and geraniol when assayed with geranyl diphosphate. Sesquiterpene synthase SasesquiTPS1 produced the monocyclic sesquiterpene alcohol germacrene D-4-ol and helminthogermacrene, when incubated with farnesyl diphosphate. Also present were α-bulnesene, γ-muurolene, α- and β-selinenes, as well as several other minor bicyclic compounds. Although these sesquiterpenes are present in only minute quantities in the distilled Sandalwood oil, the genes and their encoded enzymes described here represent the first TPS isolated and characterised from a member of the Santalaceae plant family and they may enable the future discovery of additional TPS genes in Sandalwood.
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quantitative co occurrence of sesquiterpenes a tool for elucidating their biosynthesis in indian Sandalwood santalum album
Phytochemistry, 2006Co-Authors: Christopher G Jones, Emilio L Ghisalberti, Julie A Plummer, Elizabeth L BarbourAbstract:Abstract A chemotaxonomic approach was used to investigate biosynthetic relationships between heartwood sesquiterpenes in Indian Sandalwood, Santalum album L. Strong, linear relationships exist between four structural classes of sesquiterpenes; α- and β-santalenes and bergamotene; γ- and β-curcumene; β-bisabolene and α-bisabolol and four unidentified sesquiterpenes. All samples within the heartwood yielded the same co-occurrence patterns, however wood from young trees tended to be more variable. It is proposed that the biosynthesis of each structural class of sesquiterpene in Sandalwood oil is linked through common carbocation intermediates. Lack of co-occurrence between each structural class suggests that four separate cyclase enzymes may be operative. The biosynthesis of Sandalwood oil sesquiterpenes is discussed with respect to these co-occurrence patterns. Extractable oil yield was correlated to heartwood content of each wood core and the oil composition did not vary significantly throughout the tree.
Julie A Plummer - One of the best experts on this subject based on the ideXlab platform.
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sesquiterpene variation in west australian Sandalwood santalum spicatum
Molecules, 2017Co-Authors: Jessie Moniodis, Christopher G Jones, Emilio L Ghisalberti, Julie A Plummer, Michael Renton, Liz E Barbour, Joerg BohlmannAbstract:West Australian Sandalwood (Santalum spicatum) has long been exploited for its fragrant, sesquiterpene-rich heartwood; however Sandalwood fragrance qualities vary substantially, which is of interest to the Sandalwood industry. We investigated metabolite profiles of trees from the arid northern and southeastern and semi-arid southwestern regions of West Australia for patterns in composition and co-occurrence of sesquiterpenes. Total sesquiterpene content was similar across the entire sample collection; however sesquiterpene composition was highly variable. Northern populations contained the highest levels of desirable fragrance compounds, α- and β-santalol, as did individuals from the southwest. Southeastern populations were higher in E,E-farnesol, an undesired allergenic constituent, and low in santalols. These trees generally also contained higher levels of α-bisabolol. E,E-farnesol co-occurred with dendrolasin. Contrasting α-santalol and E,E-farnesol chemotypes revealed potential for future genetic tree improvement. Although chemical variation was evident both within and among regions, variation was generally lower within regions. Our results showed distinct patterns in chemical diversity of S. spicatum across its natural distribution, consistent with earlier investigations into Sandalwood population genetics. These results are relevant for plantation tree improvement and conservation efforts.
-
the transcriptome of sesquiterpenoid biosynthesis in heartwood xylem of western australian Sandalwood santalum spicatum
Phytochemistry, 2015Co-Authors: Christopher G Jones, Emilio L Ghisalberti, Julie A Plummer, Jessie Moniodis, Liz E Barbour, Joerg BohlmannAbstract:The fragrant heartwood oil of West Australian Sandalwood (Santalum spicatum) contains a mixture of sesquiterpene olefins and alcohols, including variable levels of the valuable sesquiterpene alcohols, α- and β-santalol, and often high levels of E,E-farnesol. Transcriptome analysis revealed sequences for a nearly complete set of genes of the sesquiterpenoid biosynthetic pathway in this commercially valuable Sandalwood species. Transcriptome sequences were produced from heartwood xylem tissue of a farnesol-rich individual tree. From the assembly of 12,537 contigs, seven different terpene synthases (TPSs), several cytochromes P450, and allylic phosphatases were identified, as well as transcripts of the mevalonic acid and methylerythritol phosphate pathways. Five of the S. spicatum TPS sequences were previously unknown. The full-length cDNA of SspiTPS4 was cloned and the enzyme functionally characterized as a multi-product sesquisabinene B synthase, which complements previous characterization of santalene and bisabolol synthases in S. spicatum. While SspiTPS4 and previously cloned Sandalwood TPSs do not explain the prevalence of E,E-farnesol in S. spicatum, the genes identified in this and previous work can form a basis for future studies on natural variation of Sandalwood terpenoid oil profiles.
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biosynthesis of Sandalwood oil santalum album cyp76f cytochromes p450 produce santalols and bergamotol
PLOS ONE, 2013Co-Authors: Maria L Diazchavez, Christopher G Jones, Christopher I Keeling, Emilio L Ghisalberti, Elizabeth L Barbour, Julie A Plummer, Lufiani L Madilao, Jessie Moniodis, Sharon Jancsik, Jorg BohlmannAbstract:Sandalwood oil is one of the world’s most highly prized essential oils, appearing in many high-end perfumes and fragrances. Extracted from the mature heartwood of several Santalum species, Sandalwood oil is comprised mainly of sesquiterpene olefins and alcohols. Four sesquiterpenols, α-, β-, and epi-β-santalol and α-exo-bergamotol, make up approximately 90% of the oil of Santalum album. These compounds are the hydroxylated analogues of α-, β-, and epi-β-santalene and α-exo-bergamotene. By mining a transcriptome database of S. album for candidate cytochrome P450 genes, we cloned and characterized cDNAs encoding a small family of ten cytochrome P450-dependent monooxygenases annotated as SaCYP76F37v1, SaCYP76F37v2, SaCYP76F38v1, SaCYP76F38v2, SaCYP76F39v1, SaCYP76F39v2, SaCYP76F40, SaCYP76F41, SaCYP76F42, and SaCYP76F43. Nine of these genes were functionally characterized using in vitro assays and yeast in vivo assays to encode santalene/bergamotene oxidases and bergamotene oxidases. These results provide a foundation for production of Sandalwood oil for the fragrance industry by means of metabolic engineering, as demonstrated with proof-of-concept formation of santalols and bergamotol in engineered yeast cells, simultaneously addressing conservation challenges by reducing pressure on supply of Sandalwood from native forests.
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isolation of cdnas and functional characterisation of two multi product terpene synthase enzymes from Sandalwood santalum album l
Archives of Biochemistry and Biophysics, 2008Co-Authors: Christopher G Jones, Christopher I Keeling, Emilio L Ghisalberti, Elizabeth L Barbour, Julie A Plummer, Jorg BohlmannAbstract:Abstract Sandalwood, Santalum album (Santalaceae) is a small hemi-parasitic tropical tree of great economic value. Sandalwood timber contains resins and essential oils, particularly the santalols, santalenes and dozens of other minor sesquiterpenoids. These sesquiterpenoids provide the unique Sandalwood fragrance. The research described in this paper set out to identify genes involved in essential oil biosynthesis, particularly terpene synthases (TPS) in S. album, with the long-term aim of better understanding heartwood oil production. Degenerate TPS primers amplified two genomic TPS fragments from S. album, one of which enabled the isolation of two TPS cDNAs, SamonoTPS1 (1731 bp) and SasesquiTPS1 (1680 bp). Both translated protein sequences shared highest similarity with known TPS from grapevine (Vitis vinifera). Heterologous expression in Escherichia coli produced catalytically active proteins. SamonoTPS1 was identified as a monoterpene synthase which produced a mixture of (+)-α-terpineol and (−)-limonene, along with small quantities of linalool, myrcene, (−)-α-pinene, (+)-sabinene and geraniol when assayed with geranyl diphosphate. Sesquiterpene synthase SasesquiTPS1 produced the monocyclic sesquiterpene alcohol germacrene D-4-ol and helminthogermacrene, when incubated with farnesyl diphosphate. Also present were α-bulnesene, γ-muurolene, α- and β-selinenes, as well as several other minor bicyclic compounds. Although these sesquiterpenes are present in only minute quantities in the distilled Sandalwood oil, the genes and their encoded enzymes described here represent the first TPS isolated and characterised from a member of the Santalaceae plant family and they may enable the future discovery of additional TPS genes in Sandalwood.
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quantitative co occurrence of sesquiterpenes a tool for elucidating their biosynthesis in indian Sandalwood santalum album
Phytochemistry, 2006Co-Authors: Christopher G Jones, Emilio L Ghisalberti, Julie A Plummer, Elizabeth L BarbourAbstract:Abstract A chemotaxonomic approach was used to investigate biosynthetic relationships between heartwood sesquiterpenes in Indian Sandalwood, Santalum album L. Strong, linear relationships exist between four structural classes of sesquiterpenes; α- and β-santalenes and bergamotene; γ- and β-curcumene; β-bisabolene and α-bisabolol and four unidentified sesquiterpenes. All samples within the heartwood yielded the same co-occurrence patterns, however wood from young trees tended to be more variable. It is proposed that the biosynthesis of each structural class of sesquiterpene in Sandalwood oil is linked through common carbocation intermediates. Lack of co-occurrence between each structural class suggests that four separate cyclase enzymes may be operative. The biosynthesis of Sandalwood oil sesquiterpenes is discussed with respect to these co-occurrence patterns. Extractable oil yield was correlated to heartwood content of each wood core and the oil composition did not vary significantly throughout the tree.
Jessie Moniodis - One of the best experts on this subject based on the ideXlab platform.
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sesquiterpene variation in west australian Sandalwood santalum spicatum
Molecules, 2017Co-Authors: Jessie Moniodis, Christopher G Jones, Emilio L Ghisalberti, Julie A Plummer, Michael Renton, Liz E Barbour, Joerg BohlmannAbstract:West Australian Sandalwood (Santalum spicatum) has long been exploited for its fragrant, sesquiterpene-rich heartwood; however Sandalwood fragrance qualities vary substantially, which is of interest to the Sandalwood industry. We investigated metabolite profiles of trees from the arid northern and southeastern and semi-arid southwestern regions of West Australia for patterns in composition and co-occurrence of sesquiterpenes. Total sesquiterpene content was similar across the entire sample collection; however sesquiterpene composition was highly variable. Northern populations contained the highest levels of desirable fragrance compounds, α- and β-santalol, as did individuals from the southwest. Southeastern populations were higher in E,E-farnesol, an undesired allergenic constituent, and low in santalols. These trees generally also contained higher levels of α-bisabolol. E,E-farnesol co-occurred with dendrolasin. Contrasting α-santalol and E,E-farnesol chemotypes revealed potential for future genetic tree improvement. Although chemical variation was evident both within and among regions, variation was generally lower within regions. Our results showed distinct patterns in chemical diversity of S. spicatum across its natural distribution, consistent with earlier investigations into Sandalwood population genetics. These results are relevant for plantation tree improvement and conservation efforts.
-
the transcriptome of sesquiterpenoid biosynthesis in heartwood xylem of western australian Sandalwood santalum spicatum
Phytochemistry, 2015Co-Authors: Christopher G Jones, Emilio L Ghisalberti, Julie A Plummer, Jessie Moniodis, Liz E Barbour, Joerg BohlmannAbstract:The fragrant heartwood oil of West Australian Sandalwood (Santalum spicatum) contains a mixture of sesquiterpene olefins and alcohols, including variable levels of the valuable sesquiterpene alcohols, α- and β-santalol, and often high levels of E,E-farnesol. Transcriptome analysis revealed sequences for a nearly complete set of genes of the sesquiterpenoid biosynthetic pathway in this commercially valuable Sandalwood species. Transcriptome sequences were produced from heartwood xylem tissue of a farnesol-rich individual tree. From the assembly of 12,537 contigs, seven different terpene synthases (TPSs), several cytochromes P450, and allylic phosphatases were identified, as well as transcripts of the mevalonic acid and methylerythritol phosphate pathways. Five of the S. spicatum TPS sequences were previously unknown. The full-length cDNA of SspiTPS4 was cloned and the enzyme functionally characterized as a multi-product sesquisabinene B synthase, which complements previous characterization of santalene and bisabolol synthases in S. spicatum. While SspiTPS4 and previously cloned Sandalwood TPSs do not explain the prevalence of E,E-farnesol in S. spicatum, the genes identified in this and previous work can form a basis for future studies on natural variation of Sandalwood terpenoid oil profiles.
-
biosynthesis of Sandalwood oil santalum album cyp76f cytochromes p450 produce santalols and bergamotol
PLOS ONE, 2013Co-Authors: Maria L Diazchavez, Christopher G Jones, Christopher I Keeling, Emilio L Ghisalberti, Elizabeth L Barbour, Julie A Plummer, Lufiani L Madilao, Jessie Moniodis, Sharon Jancsik, Jorg BohlmannAbstract:Sandalwood oil is one of the world’s most highly prized essential oils, appearing in many high-end perfumes and fragrances. Extracted from the mature heartwood of several Santalum species, Sandalwood oil is comprised mainly of sesquiterpene olefins and alcohols. Four sesquiterpenols, α-, β-, and epi-β-santalol and α-exo-bergamotol, make up approximately 90% of the oil of Santalum album. These compounds are the hydroxylated analogues of α-, β-, and epi-β-santalene and α-exo-bergamotene. By mining a transcriptome database of S. album for candidate cytochrome P450 genes, we cloned and characterized cDNAs encoding a small family of ten cytochrome P450-dependent monooxygenases annotated as SaCYP76F37v1, SaCYP76F37v2, SaCYP76F38v1, SaCYP76F38v2, SaCYP76F39v1, SaCYP76F39v2, SaCYP76F40, SaCYP76F41, SaCYP76F42, and SaCYP76F43. Nine of these genes were functionally characterized using in vitro assays and yeast in vivo assays to encode santalene/bergamotene oxidases and bergamotene oxidases. These results provide a foundation for production of Sandalwood oil for the fragrance industry by means of metabolic engineering, as demonstrated with proof-of-concept formation of santalols and bergamotol in engineered yeast cells, simultaneously addressing conservation challenges by reducing pressure on supply of Sandalwood from native forests.
Joerg Bohlmann - One of the best experts on this subject based on the ideXlab platform.
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sesquiterpene variation in west australian Sandalwood santalum spicatum
Molecules, 2017Co-Authors: Jessie Moniodis, Christopher G Jones, Emilio L Ghisalberti, Julie A Plummer, Michael Renton, Liz E Barbour, Joerg BohlmannAbstract:West Australian Sandalwood (Santalum spicatum) has long been exploited for its fragrant, sesquiterpene-rich heartwood; however Sandalwood fragrance qualities vary substantially, which is of interest to the Sandalwood industry. We investigated metabolite profiles of trees from the arid northern and southeastern and semi-arid southwestern regions of West Australia for patterns in composition and co-occurrence of sesquiterpenes. Total sesquiterpene content was similar across the entire sample collection; however sesquiterpene composition was highly variable. Northern populations contained the highest levels of desirable fragrance compounds, α- and β-santalol, as did individuals from the southwest. Southeastern populations were higher in E,E-farnesol, an undesired allergenic constituent, and low in santalols. These trees generally also contained higher levels of α-bisabolol. E,E-farnesol co-occurred with dendrolasin. Contrasting α-santalol and E,E-farnesol chemotypes revealed potential for future genetic tree improvement. Although chemical variation was evident both within and among regions, variation was generally lower within regions. Our results showed distinct patterns in chemical diversity of S. spicatum across its natural distribution, consistent with earlier investigations into Sandalwood population genetics. These results are relevant for plantation tree improvement and conservation efforts.
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the transcriptome of sesquiterpenoid biosynthesis in heartwood xylem of western australian Sandalwood santalum spicatum
Phytochemistry, 2015Co-Authors: Christopher G Jones, Emilio L Ghisalberti, Julie A Plummer, Jessie Moniodis, Liz E Barbour, Joerg BohlmannAbstract:The fragrant heartwood oil of West Australian Sandalwood (Santalum spicatum) contains a mixture of sesquiterpene olefins and alcohols, including variable levels of the valuable sesquiterpene alcohols, α- and β-santalol, and often high levels of E,E-farnesol. Transcriptome analysis revealed sequences for a nearly complete set of genes of the sesquiterpenoid biosynthetic pathway in this commercially valuable Sandalwood species. Transcriptome sequences were produced from heartwood xylem tissue of a farnesol-rich individual tree. From the assembly of 12,537 contigs, seven different terpene synthases (TPSs), several cytochromes P450, and allylic phosphatases were identified, as well as transcripts of the mevalonic acid and methylerythritol phosphate pathways. Five of the S. spicatum TPS sequences were previously unknown. The full-length cDNA of SspiTPS4 was cloned and the enzyme functionally characterized as a multi-product sesquisabinene B synthase, which complements previous characterization of santalene and bisabolol synthases in S. spicatum. While SspiTPS4 and previously cloned Sandalwood TPSs do not explain the prevalence of E,E-farnesol in S. spicatum, the genes identified in this and previous work can form a basis for future studies on natural variation of Sandalwood terpenoid oil profiles.
