Biosynthesis and localization of parthenolide in glandular trichomes of feverfew (Tanacetum parthenium L. Schulz Bip.)

Majdi, Mohammad; Liu, Qin; Karimzadeh, Ghasem; Malboobi, Mohammad Ali; Beekwilder, Jules; Cankar, Katarina; Vos, Ric C. H. de; Todorović, Slađana; Simonović, Ana; Bouwmeester, Harro J.

doi:10.1016/j.phytochem.2011.04.021

Cited by 99 publications

(86 citation statements)

References 61 publications

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“…Although glandular trichomes are still very conspicuous in stems with SG ph , the lower concentration of (-)HAA may result from a lower number of functional trichomes. A developmental stage-specific expression in glandular trichomes has been reported in other Asteraceae as Helianthus annuus [46] and Tenacetum parthenium [12]. In Artemisia annua, trichome collapse has been proposed for the decrease in artemisinin con-tent during later stages of leaf development [67].…”

Section: Discussionmentioning

confidence: 93%

“…A growing body of experimental evidence shows that terpene biosynthesis takes place within glandular trichomes [11] [12] [59]- [63]. As an example, transcriptome analysis of Artemisia annua glandular trichomes revealed the presence of contigs corresponding to multiple enzymes for terpenoid and flavonoid biosynthesis suggesting their important metabolic activity [64].…”

Section: Discussionmentioning

confidence: 99%

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Secretory Structures in Flourensia campestris and F. oolepis: Ultrastructure, Distribution, and (-)-Hamanasic Acid A Secretion

Silva¹,

Tourn²,

López³

et al. 2015

AJPS

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In this work, the localization, density, morphology and ultrastructure of secretory structures in aerial organs of Flourensia campestris (FC) and F. oolepis (FO) (Asteraceae) by means of a combination of light, fluorescence, transmission (TEM) and scanning electron microscopy (SEM) were examined. The possible role of secretory structures in the production and secretion of the phytotoxic sesquiterpene (-)-hamanasic acid A ((-)HAA) in both species was also assessed. Capitate glandular trichomes were found in all reproductive organs of FC and FO, and were being reported for the first time. These glandular trichomes, typically associated to edges and veins, were of the same type as those already described for vegetative organs, and were abundant in involucral bracts and corolla of tubulose and ligulate flowers. Their density in reproductive organs of both species was similar (ca. 30/mm 2 ) and lower than that found in leaves (ca. 100/mm 2 ) and stems (ca. 160/mm 2 in FC, and up to 650/mm 2 in FO). Glandular trichomes in vegetative organs followed a species-* Corresponding authors. M. P. Silva et al. 926specific pattern of distribution. TEM and SEM observations suggest that each species differs in the way in which secretory materials are released to the outside: through cracks or pores in FC, or through a loose cuticle in FO. Similar inspections of the secretory ducts revealed lipophilic vacuoles localized in subepithelial and epithelial cells, in which secretions accumulated before being transferred to the duct. The presence of wall ingrowths in subepithelial cells suggests that granulocrine secretion operates in these species. Secretory ducts varied in density and diameter among the organs in both species, with the combination being maximal in woody stems. (-)HAA was only detected in surface secreted resins of both species, and its concentration (2D-TLC, GC-FID) was intimately associated with the distribution and density of glandular trichomes in each organ (capitula, leaves, and stems with primary or secondary growth). In addition, no (-)HAA was detected internally in the resins collected from secretory ducts. The composition of these resins showed distinctive profiles for FC and FO, and only four from ca. 30 compounds detected (GC/MS) were shared by both species. In addition to the elucidation of ultrastructural traits, distribution and density of secretory structures in aerial organs of FC and FO, present findings suggest a functional role for glandular trichomes in the secretion of the putative phytotoxic allelochemical (-)HAA.

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Section: Discussionmentioning

confidence: 93%

Section: Discussionmentioning

confidence: 99%

Secretory Structures in Flourensia campestris and F. oolepis: Ultrastructure, Distribution, and (-)-Hamanasic Acid A Secretion

Silva¹,

Tourn²,

López³

et al. 2015

AJPS

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“…TpGAS has previously been described as a germacrene A synthase [29]. Expression of TpGAS in N. benthamiana followed by extraction using HS-SPMS and analysis on GC-MS with the different fiber materials PDMS, PDMS/DVB, PDMS/CAR, and PDMS/CAR/DVB at an injection port temperature of 250 °C only resulted in rearrangement products and did not yield any germacrene A (2) ( Figure 5, Supplementary Figures 5 and 6).…”

Section: Comparison Of Spme Fibers Using Tpgas -Germacrene a Synthasementioning

confidence: 96%

“…cfDXS from Coleus forskohlii was kindly provided by Johan RanbergAndersen (University of Copenhagen, Copenhagen, Denmark) [28]. TpGAS (JF819848) from Tanacetum parthenium in ImpactVector1.5 was kindly provided by Harro Bouwmeester (University of Wageningen, Wageningen, The Netherlands) [29]. Table 1.…”

Section: Cloningmentioning

confidence: 99%

Optimization of Biochemical Screening Methods for Volatile and Unstable Sesquiterpenoids Using HS-SPME-GC-MS

2015

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HS-SPME-GC-MS has been suggested as a fast and robust analytical platform for the product characterization of sesquiterpene synthases. The choice of fiber and injection temperature can have a significant effect on the observed product profile, due to the chemical rearrangements that can occur on the fiber material. Here we present a systematic study on the effects of fiber choice and injection port temperature on the observed sesquiterpenoid profile of four sesquiterpene synthases expressed in Nicotiana benthamiana. We found that the absorbent material PDMS was much less likely to support acid-induced rearrangement of sesquiterpenoids when compared to the adsorbent materials PDMS/DVB, PDMS/CAR, and PDMS/CAR/DVB. Furthermore, utilizing an injection port temperature at 160 °C almost eliminated the inherent thermal instability of germacrene sesquiterpenoids. Thus, for fast screening of sesquiterpene synthases, the results suggest that PDMS fibers and an injection temperature of 160 °C provide a fast and reproducible HS-SPME GC-MS method when using H2 as carrier gas.

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“…In our histological and scanning electron microscopy work, we found high number of trichomes distributed on the outer and lateral inner tepals of V. Mimi Palmer compared to other floral parts (unpublished data). Trichomes have been reported to be the potential sites for volatiles and scent emission [33][34][35].…”

Section: Expression Of Vmpaca Transcript In Different Floralmentioning

confidence: 99%

Molecular Cloning, Sequencing, and Characterization of a Putative Acetyl-CoA-C-acetyltransferase cDNA from a Highly Fragrant Orchid Hybrid Vanda Mimi Palmer

2012

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tessellata (Roxb.) Hk.f. ex G. Don, is cultivated as a potted ornamental plant mainly for its fragrance rather than its look. Plant acetyl-CoA-C-acetyltransferase (ACA) is involved in the condensation of two acetyl-CoAs to form acetoacetyl-CoA, which condenses with another acetyl-CoA to yield a crucial molecule, 3-hydroxyl-3-methylglutaryl-CoA, at the initial step of the mevalonate (MVA) pathway. An ACA gene from vandaceous orchid has never been reported. We describe the isolation and molecular characterization of an ACA-like gene from V. Mimi Palmer (designated as VMPACA) to facilitate a better understanding of the terpenoid biosynthesis pathway in orchids. The deduced VMPACA encodes a 376-amino-acid protein with a molecular weight of 39 kDa, which comprises an open reading frame of 1128 bp. It is flanked by 87 bp of 5 -untranslated region and 174 bp of 3 -untranslated region including a poly-A tail. Its protein sequence is 81% identical to other plant ACAs and contains a thiolase active site. The fluctuation expression pattern of VMPACA transcript by real-time RT-PCR showed that it is developmentally and temporally regulated with predominant expression in outer and lateral inner tepals compared to vegetative tissues.

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Biosynthesis and localization of parthenolide in glandular trichomes of feverfew (Tanacetum parthenium L. Schulz Bip.)

Cited by 99 publications

References 61 publications

Secretory Structures in <i>Flourensia campestris</i> and <i>F. oolepis</i>: Ultrastructure, Distribution, and (-)-Hamanasic Acid A Secretion

Secretory Structures in <i>Flourensia campestris</i> and <i>F. oolepis</i>: Ultrastructure, Distribution, and (-)-Hamanasic Acid A Secretion

Optimization of Biochemical Screening Methods for Volatile and Unstable Sesquiterpenoids Using HS-SPME-GC-MS

Molecular Cloning, Sequencing, and Characterization of a Putative Acetyl-CoA-C-acetyltransferase cDNA from a Highly Fragrant Orchid Hybrid Vanda Mimi Palmer

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Biosynthesis and localization of parthenolide in glandular trichomes of feverfew (Tanacetum parthenium L. Schulz Bip.)

Cited by 99 publications

References 61 publications

Secretory Structures in &lt;i&gt;Flourensia campestris&lt;/i&gt; and &lt;i&gt;F. oolepis&lt;/i&gt;: Ultrastructure, Distribution, and (-)-Hamanasic Acid A Secretion

Secretory Structures in &lt;i&gt;Flourensia campestris&lt;/i&gt; and &lt;i&gt;F. oolepis&lt;/i&gt;: Ultrastructure, Distribution, and (-)-Hamanasic Acid A Secretion

Optimization of Biochemical Screening Methods for Volatile and Unstable Sesquiterpenoids Using HS-SPME-GC-MS

Molecular Cloning, Sequencing, and Characterization of a Putative Acetyl-CoA-C-acetyltransferase cDNA from a Highly Fragrant Orchid Hybrid Vanda Mimi Palmer

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Secretory Structures in <i>Flourensia campestris</i> and <i>F. oolepis</i>: Ultrastructure, Distribution, and (-)-Hamanasic Acid A Secretion

Secretory Structures in <i>Flourensia campestris</i> and <i>F. oolepis</i>: Ultrastructure, Distribution, and (-)-Hamanasic Acid A Secretion