(2Z)-4-hydroxy-2-methyl-2-buten-1-yl-ß-D-glucoside and (2Z)-1-hydroxy-2-methyl-2-buten-4-yl-ß-D-glucoside: Two New Hemiterpene Glucosides from<i>Vitis vinifera</i>Leaves

Messerer, Monika; Winterhalter, Peter

doi:10.1080/10575639508044067

Cited by 7 publications

(3 citation statements)

References 16 publications

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“…S3B). 1 H and 13 C NMR data for all three synthetic products agreed well (Table S1) with previously reported occurrences of these and related compounds from other plant species (14)(15)(16)(17).…”

Section: Resultssupporting

confidence: 87%

“…Molecular ions were absent but fragments at m/z 217, 204, 191, 147, and 129 were characteristic of trimethylsilylglycosides (12). The key fragment, m/z 157 (accurate masses 157.1048 and 157.1047 in the major and minor isomer, respectively) due to the aglycone, has the empirical formula C 8 H 17 OSi and corresponds to the structural fragment [(CH 3 ) 3 SiOCH 2 CH = C(Me)CH 2 ] − (calculated mass = 157.1049) that is consistent with the C5-enediol glycoside (hemiterpenoid glycoside, HTG) structure. 1D NOESY data of the major isomer indicated the trans (E) arrangement of the double bond and 2D-NMR spectroscopy placed the glycosidic linkage at the 1 position as shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

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Metabolomic analysis ofArabidopsisreveals hemiterpenoid glycosides as products of a nitrate ion-regulated, carbon flux overflow

Ward

Baker

Llewellyn

et al. 2011

Proc. Natl. Acad. Sci. U.S.A.

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An understanding of the balance between carbon and nitrogen assimilation in plants is key to future bioengineering for a range of applications. Metabolomic analysis of the model plant, Arabidopsis thaliana, using combined NMR-MS revealed the presence of two hemiterpenoid glycosides that accumulated in leaf tissue, to ∼1% dry weight under repeated nitrate-deficient conditions. The formation of these isoprenoids was correlated with leaf nitrate concentrations that could also be assayed in the metabolomic data using a unique flavonoid-nitrate mass spectral adduct. Analysis of leaf and root tissue from plants grown in hydroponics with a variety of root stressors identified the conditions under which the isoprenoid pathway in leaves was diverted to the hemiterpenoids. These compounds were strongly induced by root wounding or oxidative stress and weakly induced by potassium deficiency. Other stresses such as cold, saline, and osmotic stress did not induce the compounds. Replacement of nitrate with ammonia failed to suppress the formation of the hemiterpenoids, indicating that nitrate sensing was a key factor. Feeding of intermediates was used to study aspects of 2-C-methyl-D-erythritol-4-phosphate pathway regulation leading to hemiterpenoid formation. The formation of the hemiterpenoids in leaves was strongly correlated with the induction of the phenylpropanoids scopolin and coniferin in roots of the same plants. These shunts of photosynthetic carbon flow are discussed in terms of overflow mechanisms that have some parallels with isoprene production in tree species.F or centuries mankind has relied on carbon, prehistorically fixed from the atmosphere by plants and algae, as a source of fuel and other materials. This is a dwindling resource and, to develop renewable sources of chemicals, knowledge of the biochemical pathways that link photosynthesis to the accumulation of useful materials will be paramount. Terpenoids (isoprenoids) are examples of carbon-rich products that occur prolifically across the plant kingdom. They are not only end products of chloroplast assimilation of photosynthetic carbon but also, by virtue of the phytyl side chains of chlorophyll, key elements of the machinery of photosynthesis. Some terpenoids are ubiquitous and are classed as primary metabolites (sterols, carotenoids, and phytyl side chains of chlorophyll); others are hormones (gibberellins, abscisic acid, brassinosteroids, and strigolactones). However, the majority of terpenoids, especially those that can accumulate to high levels in plants, are classed as secondary metabolites, although many have roles in chemical ecology. Manipulation of flux through the primary terpenoid pathways and the accumulation of terpenoids via the secondary pathways both have potential for exploitation. Arabidopsis, the model plant, was, until recently, considered to be poorly endowed with terpenoids. For example, this species does not appear to contain oxidized sesqui-and diterpenes, compounds that are widespread in plants (1). There are some 30 terpene synt...

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Section: Resultssupporting

confidence: 87%

Section: Resultsmentioning

confidence: 99%

Metabolomic analysis ofArabidopsisreveals hemiterpenoid glycosides as products of a nitrate ion-regulated, carbon flux overflow

Ward

Baker

Llewellyn

et al. 2011

Proc. Natl. Acad. Sci. U.S.A.

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“…Gewurztraminer and were identified by MS and NMR spectroscopy as O-β-D-apiofuranosyl-(1→6)-O-β-D-glucopyranosides of 3-methyl-3-butenol 17 and of 3-methyl-2-butenol 18 (30). Two hemiterpene glycosides, (2Z)-3-hydroxy-1-methyl-1-propenyl-β-D-glucopyranoside 19 and (2Z)-3-hydroxy-2-methyl-1-propenyl-β-D-glucopyranoside 20, were identified in a water-soluble extract obtained from Riesling grapevine leaves and purified by HPLC (31).…”

Section: Hemiterpenoid Glycosides and Related Compoundsmentioning

confidence: 99%

Astonishing diversity of natural surfactants: 7. Biologically active hemi‐ and monoterpenoid glycosides

Dembitsky

2006

Lipids

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This review article presents 90 hemi- and 188 monoterpenoid glycosides, isolated and identified from plants and microorganisms, that demonstrate different biological activities. These natural bioactive glycosides are good prospects for future chemical preparations from these compounds as antioxidants and as anticancer, antimicrobial, and antibacterial agents. These glycosidic compounds have been subdivided into several groups, including hemiterpenoids; acyclic, monocyclic, and bicyclic monoterpenoids; and iridoid monoterpenoids.

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Metabolomics Reveals Hemiterpenoids as New Players in the Carbon–Nitrogen Economy

Ward

2013

50 Years of Phytochemistry Research

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(2Z)-4-hydroxy-2-methyl-2-buten-1-yl-ß-D-glucoside and (2Z)-1-hydroxy-2-methyl-2-buten-4-yl-ß-D-glucoside: Two New Hemiterpene Glucosides fromVitis viniferaLeaves

Cited by 7 publications

References 16 publications

Metabolomic analysis ofArabidopsisreveals hemiterpenoid glycosides as products of a nitrate ion-regulated, carbon flux overflow

Metabolomic analysis ofArabidopsisreveals hemiterpenoid glycosides as products of a nitrate ion-regulated, carbon flux overflow

Astonishing diversity of natural surfactants: 7. Biologically active hemi‐ and monoterpenoid glycosides

Metabolomics Reveals Hemiterpenoids as New Players in the Carbon–Nitrogen Economy

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