The transcriptome of sesquiterpenoid biosynthesis in heartwood xylem of Western Australian sandalwood (Santalum spicatum)

Moniodis, Jessie; Jones, Callum; Barbour, Elizabeth L.; Ghisalberti, Emilio L.; Bohlmann, Jöerg

doi:10.1016/j.phytochem.2014.12.009

Cited by 40 publications

(18 citation statements)

References 30 publications

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“…The best method for identification of the molecular structure should be NMR, but a drawback is the demand of a chemically pure sample in amounts that might be difficult to obtain from the interesting non-polar part of the extract. A possible method to purify and concentrate the unknown might be by applying preparative GC (Zuo et al 2013;McNair and Miller 2009). Thus, after liquid extraction of carrot leaves, samples were concentrated and then pre-purified by flash chromatography to eliminate and remove more of the polar part of the matrix.…”

Section: Resultsmentioning

confidence: 99%

Identification of sesquisabinene B in carrot (Daucus carota L.) leaves as a compound electrophysiologically active to the carrot psyllid (Trioza apicalis Förster)

et al. 2019

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The Carrot psyllid, Trioza apicalis Förster (Homoptera: Psylloidea: Triozidae) is one of the major insect pests of carrots (Daucus carota L.) in parts of northern and central Europe. Gas chromatography-single-sensillum recording (GC-SSR) previously confirmed several active compounds in a carrot leaf extract, but the most active compound remained unidentified. Mass fragmentation patterns observed from the unidentified active compound when analyzed by gas chromatography and mass spectrometry (GC-MS) was used to propose β-sesquiphellandrene and α-cis-bergamotene to be candidates as the unidentified compound. The compounds were synthesized and their mass spectra were nearly identical with the unknown active compound. But, the retention times differed from the compound in the carrot leaf extract. Thus, to obtain the unidentified compound pure enough and in adequate amounts for nuclear magnetic resonance (NMR) analysis, preparative gas chromatography was applied to separate and concentrate this biologically active compound. Analysis by liquid chromatography quadrupole time of flight mass spectrometry (LC-QTOF) confirmed the unidentified compound to be a compound with the formula of C 15 H 24 and together with GC-MS, 1 H and 13 C NMR analysis sesquisabinene B was identified as the unidentified compound in the extract. GC-SSR was then used to finally confirm the biological activity of sesquisabinene B isolated from the carrot leaf extract via preparative GC.

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Section: Resultsmentioning

confidence: 99%

Identification of sesquisabinene B in carrot (Daucus carota L.) leaves as a compound electrophysiologically active to the carrot psyllid (Trioza apicalis Förster)

et al. 2019

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“…Terpenoids or isoprenoids constitute one of the most structurally diverse groups of biomolecules in plants. The building blocks of these multifaceted structures are synthesized either through the MVA or plastid-specific MEP pathway (Moniodis et al, 2015;Srivastava et al, 2015). Differential regulation of the rate-limiting enzyme in the MVA pathway, 3-hydroxy-3-methylglutaryl CoA reductase, and various terpenoid synthases has been reported under cold stress in sandalwood (Zhang et al, 2017).…”

Section: Discussionmentioning

confidence: 99%

“…Currently, large-scale transcriptomic data sets are available for sandalwood (Diaz-Chavez et al, 2013;Srivastava et al, 2015;Zhang et al, 2015Zhang et al, , 2017Celedon et al, 2016) and Santalum spicatum (Moniodis et al, 2015). Most of these genomic resources have been utilized to identify genes involved in sandalwood oil biosynthesis, cold stress response, and the hemiparasitic nature of its roots.…”

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confidence: 99%

Multi-Omics Driven Assembly and Annotation of the Sandalwood (Santalum album) Genome

et al. 2018

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Indian sandalwood () is an important tropical evergreen tree known for its fragrant heartwood-derived essential oil and its valuable carving wood. Here, we applied an integrated genomic, transcriptomic, and proteomic approach to assemble and annotate the Indian sandalwood genome. Our genome sequencing resulted in the establishment of a draft map of the smallest genome for any woody tree species to date (221 Mb). The genome annotation predicted 38,119 protein-coding genes and 27.42% repetitive DNA elements. In-depth proteome analysis revealed the identities of 72,325 unique peptides, which confirmed 10,076 of the predicted genes. The addition of transcriptomic and proteogenomic approaches resulted in the identification of 53 novel proteins and 34 gene-correction events that were missed by genomic approaches. Proteogenomic analysis also helped in reassigning 1,348 potential noncoding RNAs as bona fide protein-coding messenger RNAs. Gene expression patterns at the RNA and protein levels indicated that peptide sequencing was useful in capturing proteins encoded by nuclear and organellar genomes alike. Mass spectrometry-based proteomic evidence provided an unbiased approach toward the identification of proteins encoded by organellar genomes. Such proteins are often missed in transcriptome data sets due to the enrichment of only messenger RNAs that contain poly(A) tails. Overall, the use of integrated omic approaches enhanced the quality of the assembly and annotation of this nonmodel plant genome. The availability of genomic, transcriptomic, and proteomic data will enhance genomics-assisted breeding, germplasm characterization, and conservation of sandalwood trees.

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“…In the last few years, genes and enzymes have been reported for all but the critical final step in biosynthesis of the most valuable sesquiterpenol components of tropical sandalwood and related Santalum species. Specifically, we have cloned and characterized FPPS and a suite of sesquiterpene synthases including SaSSy (Jones et al ., ; Moniodis et al ., ), plus several monoterpene synthases for biosynthesis of minor sandalwood compounds (Jones et al ., ). The elusive final step in biosynthesis of the four main quality‐defining sandalwood oil components, namely ( Z )‐α‐santalol, ( Z )‐β‐santalol, ( Z )‐ epi ‐β‐santalol and ( Z )‐α‐ exo‐ bergamotol, was proposed to involve stereo‐selective hydroxylation of the four SaSSy products α‐santalene, β‐santalene, epi‐ β‐santalene and α‐ exo ‐bergamotene.…”

Section: Discussionmentioning

confidence: 99%

Heartwood‐specific transcriptome and metabolite signatures of tropical sandalwood (Santalum album) reveal the final step of (Z)‐santalol fragrance biosynthesis

et al. 2016

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SUMMARYTropical sandalwood (Santalum album) produces one of the world's most highly prized fragrances, which is extracted from mature heartwood. However, in some places such as southern India, natural populations of this slow-growing tree are threatened by over-exploitation. Sandalwood oil contains four major and fragrance-defining sesquiterpenols:The first committed step in their biosynthesis is catalyzed by a multi-product santalene/bergamotene synthase. Sandalwood cytochromes P450 of the CYP76F sub-family were recently shown to hydroxylate santalenes and bergamotene; however, these enzymes produced mostly (E)-santalols and (E)-a-exo-bergamotol. We hypothesized that different santalene/bergamotene hydroxylases evolved in S. album to stereo-selectively produce (E)-or (Z)-sesquiterpenols, and that genes encoding (Z)-specific P450s contribute to sandalwood oil formation if co-expressed in the heartwood with upstream genes of sesquiterpene biosynthesis. This hypothesis was validated by the discovery of a heartwood-specific transcriptome signature for sesquiterpenoid biosynthesis, including highly expressed SaCYP736A167 transcripts. We characterized SaCYP736A167 as a multi-substrate P450, which stereo-selectively produces (Z)-a-santalol, (Z)-b-santalol, (Z)-epi-b-santalol and (Z)-a-exo-bergamotol, matching authentic sandalwood oil. This work completes the discovery of the biosynthetic enzymes of key components of sandalwood fragrance, and highlights the evolutionary diversification of stereo-selective P450s in sesquiterpenoid biosynthesis. Bioengineering of microbial systems using SaCYP736A167, combined with santalene/bergamotene synthase, has potential for development of alternative industrial production systems for sandalwood oil fragrances.

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The transcriptome of sesquiterpenoid biosynthesis in heartwood xylem of Western Australian sandalwood (Santalum spicatum)

Cited by 40 publications

References 30 publications

Identification of sesquisabinene B in carrot (Daucus carota L.) leaves as a compound electrophysiologically active to the carrot psyllid (Trioza apicalis Förster)

Identification of sesquisabinene B in carrot (Daucus carota L.) leaves as a compound electrophysiologically active to the carrot psyllid (Trioza apicalis Förster)

Multi-Omics Driven Assembly and Annotation of the Sandalwood (Santalum album) Genome

Heartwood‐specific transcriptome and metabolite signatures of tropical sandalwood (Santalum album) reveal the final step of (Z)‐santalol fragrance biosynthesis

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