Elucidation and in planta reconstitution of the parthenolide biosynthetic pathway

Liu, Qin; Manzano, David; Tanić, Nikola; Pešić, Milica; Banković, Jasna; Pateraki, Irini; Ricard, Lea; Ferrer, Albert; Vos, Ric C. H. de; Krol, Sander van de; Bouwmeester, Harro J.

doi:10.1016/j.ymben.2014.03.005

Cited by 72 publications

(108 citation statements)

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“…2, 4e). The latter result suggests that parthenolide decrease is probably rather due to further conversion of parthenolide to hydroxyl-parthenolide by PTH enzyme (Liu et al 2014). Taken together, the transcript levels of early pathway genes (HMGR, DXR, HDR), biosynthetic (GAS, GAO, COS, PTS) and following (PTH) genes were affected by MJ and SA, but with different intensity.…”

Section: Discussionmentioning

confidence: 89%

“…The parthenolide content declined to the level of control plants at 48 and 96 h after MJ or SA treatment. This suggests that probably a regulatory mechanism declines parthenolide content through degradation or conversion to other compounds, e.g., epoxy parthenolide or hyrdroxy parthenolide, as recently these compounds have been detected in T. parthenium (Gershenzon 1994;Liu et al 2014). The rapid increase in parthenolide amount by application of MJ within 3 h (2.2 fold) is more interesting and could have practical importance to increase parthenolide yield and understand its biosynthesis.…”

Section: Discussionmentioning

confidence: 95%

“…Germacrene A is subsequently converted into germacrenoic acid, costunolide and parthenolide by germacrene A oxidase (GAO), costunolide synthase (COS) and parthenolide synthase (PTS), respectively ( Fig. 1) (Liu et al 2014). Recently, it has been reported that parthenolide could be further converted to hydroxyl-parthenolide after expression of a hydroxylase gene, parthenolide hydroxylase (PTH) (Liu et al 2014).…”

mentioning

confidence: 99%

“…1) (Liu et al 2014). Recently, it has been reported that parthenolide could be further converted to hydroxyl-parthenolide after expression of a hydroxylase gene, parthenolide hydroxylase (PTH) (Liu et al 2014).…”

mentioning

confidence: 99%

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Parthenolide accumulation and expression of genes related to parthenolide biosynthesis affected by exogenous application of methyl jasmonate and salicylic acid in Tanacetum parthenium

2015

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Up-regulation of germacrene A synthase and down-regulation of parthenolide hydroxylase genes play key role in parthenolide accumulation of feverfew plants treated with methyl jasmonate and salicylic acid. Parthenolide is an important sesquiterpene lactone due to its anti-migraine and anti-cancer properties. Parthenolide amount was quantified by high-performance liquid chromatography after foliar application of methyl jasmonate (100 µM) or salicylic acid (1.0 mM) on feverfew leaves in time course experiment (3-96 h). Results indicate that exogenous application of methyl jasmonate or salicylic acid activated parthenolide biosynthesis. Parthenolide content reached its highest amount at 24 h after methyl jasmonate or salicylic acid treatments, which were 3.1- and 1.96-fold higher than control plants, respectively. Parthenolide transiently increased due to methyl jasmonate or salicylic acid treatments until 24 h, but did not show significant difference compared with control plants at 48 and 96 h time points in both treatments. Also, the transcript levels of early pathway (upstream) genes of terpene biosynthesis including 3-hydroxy-3-methylglutaryl-coenzyme A reductase, 1-deoxy-D-xylulose-5-phosphate reductoisomerase and hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate reductase and the biosynthetic genes of parthenolide including germacrene A synthase, germacrene A oxidase, costunolide synthase and parthenolide synthase were increased by methyl jasmonate and salicylic acid treatments, but with different intensity. The transcriptional levels of these genes were higher in methyl jasmonate-treated plants than salicylic acid-treated plants. Parthenolide content measurements along with expression pattern analysis of the aforementioned genes and parthenolide hydroxylase as side branch gene of parthenolide suggest that the expression patterns of early pathway genes were not directly consistent with parthenolide accumulation pattern; hence, parthenolide accumulation is probably further modulated by the expression of its biosynthetic genes, especially germacrene A synthase and also its side branch gene, parthenolide hydroxylase.

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Section: Discussionmentioning

confidence: 89%

Section: Discussionmentioning

confidence: 95%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Parthenolide accumulation and expression of genes related to parthenolide biosynthesis affected by exogenous application of methyl jasmonate and salicylic acid in Tanacetum parthenium

2015

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“…Xanthanolides belong to the C7–C8 type of STLs, and thus their lactone rings would be facilitated by a C8-hydroxylation of GAA ( Figure 1 ). The cytochrome P450 that is responsible for the formation of the C6–C7 lactone ring has been cloned from several plant species (Ikezawa et al, 2011; Liu et al, 2011, 2014), while the enzyme responsible for the formation of the C7–C8 lactone ring remains unknown. From our knowledge of the structures of xanthanolides that accumulate in X. strumarium , the tailoring enzymes in the biosynthesis of xanthanolides may include cytochrome P450s, dehydrogenases and acetyltransferases ( Figure 1 ).…”

Section: Introductionmentioning

confidence: 99%

Comparative Transcriptome Analysis Identifies Putative Genes Involved in the Biosynthesis of Xanthanolides in Xanthium strumarium L.

Gou

Chen

et al. 2016

Front. Plant Sci.

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Xanthium strumarium L. is a traditional Chinese herb belonging to the Asteraceae family. The major bioactive components of this plant are sesquiterpene lactones (STLs), which include the xanthanolides. To date, the biogenesis of xanthanolides, especially their downstream pathway, remains largely unknown. In X. strumarium, xanthanolides primarily accumulate in its glandular trichomes. To identify putative gene candidates involved in the biosynthesis of xanthanolides, three X. strumarium transcriptomes, which were derived from the young leaves of two different cultivars and the purified glandular trichomes from one of the cultivars, were constructed in this study. In total, 157 million clean reads were generated and assembled into 91,861 unigenes, of which 59,858 unigenes were successfully annotated. All the genes coding for known enzymes in the upstream pathway to the biosynthesis of xanthanolides were present in the X. strumarium transcriptomes. From a comparative analysis of the X. strumarium transcriptomes, this study identified a number of gene candidates that are putatively involved in the downstream pathway to the synthesis of xanthanolides, such as four unigenes encoding CYP71 P450s, 50 unigenes for dehydrogenases, and 27 genes for acetyltransferases. The possible functions of these four CYP71 candidates are extensively discussed. In addition, 116 transcription factors that are highly expressed in X. strumarium glandular trichomes were also identified. Their possible regulatory roles in the biosynthesis of STLs are discussed. The global transcriptomic data for X. strumarium should provide a valuable resource for further research into the biosynthesis of xanthanolides.

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Harnessing Plant Trichome Biochemistry for the Production of Useful Compounds

Tissier

2018

Molecular Pharming

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Elucidation and in planta reconstitution of the parthenolide biosynthetic pathway

Cited by 72 publications

References 43 publications

Parthenolide accumulation and expression of genes related to parthenolide biosynthesis affected by exogenous application of methyl jasmonate and salicylic acid in Tanacetum parthenium

Parthenolide accumulation and expression of genes related to parthenolide biosynthesis affected by exogenous application of methyl jasmonate and salicylic acid in Tanacetum parthenium

Comparative Transcriptome Analysis Identifies Putative Genes Involved in the Biosynthesis of Xanthanolides in Xanthium strumarium L.

Harnessing Plant Trichome Biochemistry for the Production of Useful Compounds

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