Isolation and characterization of tetra- and triacylglucose from the surface lipids of Nicotiana miersii.

Matsuzaki, Toshiake; SHINOZAKI, Yasuhiro; SUHARA, Shizuo; Shigematsu, Hitoshi; Koiwai, Akira

doi:10.1271/bbb1961.53.3343

Cited by 18 publications

(20 citation statements)

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“…Other factors include differences in acylation position, acyl-CoA specificity, and sugar core diversity (Fan et al, 2016(Fan et al, , 2017(Fan et al, , 2019Moghe et al, 2017). Most characterized acylsugar-producing species accumulate primarily acylsucroses, with isolated occurrences of acylglucoses in Nicotiana miersii, Datura metel, or S. pennellii (Burke et al, 1987;King and Calhoun, 1988;Matsuzaki et al, 1989;Ghosh et al, 2014;Liu et al, 2017;Moghe et al, 2017). Accumulation of acylsugars has only been explored in a small fraction of the approximately 2,700 known species in the Solanaceae.…”

Section: Discussionmentioning

confidence: 99%

Specialized Metabolism in a Nonmodel Nightshade: Trichome Acylinositol Biosynthesis

et al. 2020

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Plants make many biologically active, specialized metabolites, which vary in structure, biosynthesis, and the processes they influence. An increasing number of these compounds are documented to protect plants from insects, pathogens, or herbivores or to mediate interactions with beneficial organisms, including pollinators and nitrogen-fixing microbes. Acylsugars, one class of protective compounds, are made in glandular trichomes of plants across the Solanaceae family. While most described acylsugars are acylsucroses, published examples also include acylsugars with hexose cores. The South American fruit crop naranjilla (lulo; Solanum quitoense) produces acylsugars containing a myoinositol core. We identified an enzyme that acetylates triacylinositols, a function homologous to the last step in the acylsucrose biosynthetic pathway of tomato (Solanum lycopersicum). Our analysis reveals parallels between S. lycopersicum acylsucrose and S. quitoense acylinositol biosynthesis, suggesting a common evolutionary origin.

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Section: Discussionmentioning

confidence: 99%

Specialized Metabolism in a Nonmodel Nightshade: Trichome Acylinositol Biosynthesis

et al. 2020

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“…Though apparently limited in distribution relative to acylsucroses, acylglucoses occur in diverse genera including Solanum, Datura , and Nicotiana ( 16, 19, 20 ). Despite the fact that acylglucose accumulation is common to species in both Solanum and Nicotiana – which diverged approximately 24 Mya – the differences in SpASFF1 gene expression and SpASAT substrate specificity that facilitated acylglucose accumulation in S. pennellii arose in the ~7 million years since divergence from the last ancestor in common with S. lycopersicum ( 11, 49, 50 ).…”

Section: Discussionmentioning

confidence: 99%

Evolution of metabolic novelty: a trichome-expressed invertase creates specialized metabolic diversity in wild tomato

Leong

Lybrand

Lou

et al. 2018

Preprint

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24Plants produce myriad taxonomically restricted specialized metabolites. This diversity -and our 25 ability to correlate genotype with phenotype -makes the evolution of these ecologically and 26 medicinally important compounds interesting and experimentally tractable. Trichomes of tomato 27 and other nightshade family plants produce structurally diverse protective compounds termed 28 acylsugars. While cultivated tomato (Solanum lycopersicum) accumulates strictly acylsucroses, 29 the South American wild relative Solanum pennellii produces copious amounts of acylglucoses. 30 Genetic, transgenic and biochemical dissection of the S. pennellii acylglucose biosynthetic 31 pathway identified a trichome gland cell expressed invertase-like enzyme that hydrolyzes 32 acylsucroses (Sopen03g040490). This enzyme acts on the pyranose ring-acylated acylsucroses 33 Science Advances Manuscript TemplatePage 2 of 50 found in the wild tomato but not the furanose ring-decorated acylsucroses of cultivated tomato. 34 These results show that modification of the core acylsucrose biosynthetic pathway leading to loss 35 of furanose ring acylation set the stage for co-option of a general metabolic enzyme to produce a 36 new class of protective compounds. 37 38 48 This leads to new and modified pathways that produce structurally and functionally diverse 49 specialized metabolites. 50 Glandular trichome-synthesized acylated sugars ('acylsugars') are structurally diverse 51 specialized metabolites found throughout the Solanaceae (7-13). These compounds have 52 documented roles in direct and indirect protection against herbivores and microbes (14, 15), as 53 well as allelopathic properties (15, 16). Their low toxicity to vertebrates generates interest in 54 generating plant breeding strategies for deploying acylsugars in crop protection (17, 18). These 55 metabolites consist of a sugar core -typically sucrose -with aliphatic chains of variable length, 56 structure and number attached by ester linkages. Acylsugars were reported from genera across the 57 Solanaceae family, including Datura, Nicotiana, Petunia, Physalis, Salpiglossis, and Solanum 58 Science Advances Manuscript Template Page 3 of 50with single species producing at least three dozen chromatographically distinct acylsugars (10, 13, 59 16, 19-22). 60 In recent years, several evolutionarily-related enzymes were implicated in the core 61 acylsucrose biosynthetic pathways in species across the family, including the cultivated tomato 62 Solanum lycopersicum, Petunia axillaris and Salpiglossis sinuata (7,(9)(10)(11)(12) 23). These 63 biosynthetic pathways consist of trichome-expressed BAHD-family acylsugar acyltransferases 64 (ASATs) (7, 9, 23), which sequentially transfer acyl groups from acyl-coenzyme A (acyl-CoA) 65 substrates to specific hydroxyl groups of sucrose (7, 9, 23). 66 The cultivated tomato biosynthetic network is well characterized, with four ASATs -67 SlASAT1 through SlASAT4 -catalyzing consecutive reactions to produce tri-and tetra-acylate...

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“…Sucrose esters isolated from cuticular extracts of other Nicotiana species have been suggested to possess only two C 3 to C 8 acyl moieties and may have from one to four acetyl groups on the fructose. In summary, about 19 different structural types (Figure 1) of sucrose esters have been reported for Nicotiana species, and for any sugar type, a series of homologs are found due to differing acyl groups (7)(8)(9)(10)(11)(12)(13)(14). Sucrose esters regardless of their structure present real challenges in terms of isolation, sample preparation, and molecular characterization because the materials are partially esterified with linear and branched fatty acids of variable chain length.…”

Section: Introductionmentioning

confidence: 99%

Isolation, Fractionation, and Identification of Sucrose Esters from Various Oriental Tobaccos Employing Supercritical Fluids

Ashraf‐Khorassani

Nazem

Taylor

et al. 2008

Beiträge Zur Tabakforschung International/Contributions to Tobacco Research

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SUMMARYIsolation, fractionation, and identification of sucrose esters from aged oriental tobacco employing supercritical fluids have been completed. Underivatized sucrose ester-rich extracts were obtained using supercritical CO 2 at densities greater than 0.73 g/mL. Lower density CO 2 provided extracts with notable amounts of tobacco derived material; yet, no detectable sucrose ester content. Preparative supercritical fluid chromatography (SFC) provided for an additional purification of the sucrose ester-enriched fraction after column optimization. Structural assignments of the SFC fractions were facilitated using gas chromatography/mass spectrometry (GC/MS) accompanied by N,Obis(trimethylsilyl)trifluoroacetamide-dimethylformamide (BSTFA-DMF) derivatization of the free hydroxyl groups and high performance-liquid chromatography/mass spectrometry (HPLC/MS). From a relative quantitative perspective regardless of tobacco type, sucrose esters having an acetyl group on C 6 of the glucose function (Group III) were in higher concentration compared to both the concentration observed for sucrose ester of Group I (acetyl group on C 3 of fructose) and sucrose ester of Group II (no acetyl group on either glucose or fructose). Saturated fatty acid constituents were found to range from a maximum total of 18 carbons to a minimum total of 13 carbons. Unsaturated and isomeric fatty acid homologues were detected within the Group II sucrose ester. [Beitr. Tabakforsch. Int. 23 (2008) RESUMELes esters de saccharose de tabac oriental mûr ont été isolés, fractionnés et identifiés par des fluides supercritiques. Des extraits riches en esters de saccharose non dérivatisés ont été obtenus par extraction avec un dioxyde de carbone supercritique d'une densité supérieure à 0,73 g/mL. Des extraits obtenus avec un dioxyde de carbone moins dense sont riches en composants provenant du tabac, avec des teneurs en esters de saccharose non détectables. Une purification supplémentaire de la fraction

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Isolation and characterization of tetra- and triacylglucose from the surface lipids of Nicotiana miersii.

Cited by 18 publications

References 0 publications

Specialized Metabolism in a Nonmodel Nightshade: Trichome Acylinositol Biosynthesis

Specialized Metabolism in a Nonmodel Nightshade: Trichome Acylinositol Biosynthesis

Evolution of metabolic novelty: a trichome-expressed invertase creates specialized metabolic diversity in wild tomato

Isolation, Fractionation, and Identification of Sucrose Esters from Various Oriental Tobaccos Employing Supercritical Fluids

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