Synthesis of α-ionyl-β-d-glucoside and its property of flavor release

Shitong, Zeng; Sun, Shasha; Liu, Shan; Hu, Jun; He, Binglin

doi:10.1007/s10973-013-3439-y

Cited by 19 publications

(9 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Similarly, biocatalyst for the production of the C 13 -apocarotenyl glucoside according to (Effenberger et al 2019). The NMR data confirmed the structure of the product (Supplemental Figure S4) and were in accordance with those of (Zeng et al 2014). Figure S6) (Sun et al 2019).…”

Section: Genomicssupporting

confidence: 62%

Glycosylation of bioactive C₁₃-apocarotenols inNicotiana benthamianaandMentha × piperita

Sun

Putkaradze

Bohnacker

et al. 2020

Preprint

View full text Add to dashboard Cite

SummaryC13-apocarotenoids (norisoprenoids) are carotenoid-derived oxidation products, which perform important physiological functions in plants. Although their biosynthetic pathways have been extensively studied, their metabolism including glycosylation remains elusive. Candidate uridine-diphosphate glycosyltransferase genes (UGTs) were selected for their high transcript abundance in comparison with other UGTs in vegetative tissues of Nicotiana benthamiana and Mentha × piperita, as these tissues are rich sources of apocarotenoid glucosides. Hydroxylated C13-apocarotenol substrates were produced by P450-catalyzed biotransformation and microbial/plant enzyme systems were established for the synthesis of glycosides. Natural substrates were identified by physiological aglycone libraries prepared from isolated plant glycosides. In total, we identified six UGTs that catalyze the unprecedented glucosylation of C13-apocarotenols, where glucose is bound either to the cyclohexene ring or butane side chain. MpUGT86C10 is a superior novel enzyme that catalyzes the glucosylation of allelopathic 3-hydroxy-α-damascone, 3-oxo-α-ionol, 3-oxo-7,8-dihydro-α-ionol (Blumenol C) and 3-hydroxy-7,8-dihydro-β-ionol, while a germination test demonstrated the higher phytotoxic potential of a norisoprenoid glucoside in comparison to its aglycone. Glycosylation of C13-apocarotenoids has several functions in plants, including increased allelopathic activity of the aglycone, facilitating exudation by roots and allowing symbiosis with arbuscular mycorrhizal fungi. The results enable in-depth analyses of the roles of glycosylated norisoprenoid allelochemicals, the physiological functions of apocarotenoids during arbuscular mycorrhizal colonization and the associated maintenance of carotenoid homeostasis.One-sentence summaryWe identified six transferases in Nicotiana benthamiana and Mentha x piperita, two rich sources of glycosylated apocarotenoids that catalyze the unprecedented glycosylation of a range of hydroxylated α- and β-ionone/ionol derivatives and were able to modify bioactivity by glucosylation.

show abstract

Section: Genomicssupporting

confidence: 62%

Glycosylation of bioactive C₁₃-apocarotenols inNicotiana benthamianaandMentha × piperita

Sun

Putkaradze

Bohnacker

et al. 2020

Preprint

View full text Add to dashboard Cite

show abstract

“…[28][29][30] As the glycosidic bond can also be cleaved at temperatures above 200 C, glycosidic precursors were also tested in cigarettes. 31 The release mechanism exploited here, however, did not involve the glycosidic bond. Instead, we opted to employ a retro 1,4-Michael-type reaction, which has been widely used to release a,b-unsaturated ketones such as damascones and ionones 13,14,16,21,32 and represents a broadly useful release scheme.…”

Section: Introductionmentioning

confidence: 98%

Controlled fragrance release from galactose-based pro-fragrances

et al. 2014

View full text Add to dashboard Cite

show abstract

“…In this study, we applied pyrolysis-gas chromatography-mass spectroscopy (Py-GC-MS), which served as a powerful tool for conducting qualitative and quantitative analysis of thermolytic decomposition products from α-and β-CBT (20). Although studies on the thermal behavior and pyrolysis of glycosides have been reported (21)(22)(23)(24), their application of cembrene for the purpose of producing aroma and flavor compounds, such as solanone, has not been reported. By studying the product distributions obtained under different pyrolysis conditions, important basic information can be obtained that suggests appropriate precursors that could be used to provide specific flavors.…”

Section: About the Column Editormentioning

confidence: 99%

Py-GC–MS Investigation of Pyrolysis Behaviors and Decomposition Products of α- and β-2,7,11-cembratriene-4,6-diols

Huang

Yang

et al. 2022

LCGC N. Am.

View full text Add to dashboard Cite

Py-GC–MS Investigation of Pyrolysis Behaviors and Decomposition Products of α- and β-2,7,11-cembratriene-4,6-diols May 1, 2022 Shen Huang, Chen Yang, Ning Ma, Lifeng Zhou, Chunxiao Jia, Tao Wei, Duobin Mao LCGC North America, May 2022, Volume 40, Issue 5 Pages: 223–228 To study the thermal stability of cembratriene, α- and β-2, 7, 11-cembratriene-4, 6-diols (α- and β-CBT) were isolated from tobacco leaves. Thermogravimetric (TG) and differential thermogravimetric (DTG) analyses were used to evaluate the cleavage differences between the two compounds. The TGA results showed the peak temperatures (Tp) were 263.3 °C and 254.1 °C with the largest weight loss rate; the significant weight losses were 90.96% and 99.45%. Pyrolysis gas chromatography–mass spectrometry (Py-GC–MS) was employed for the pyrolysis products at different temperatures (300, 600, and 900 °C) under either N2 or an O2:N2 (10%:90%) mixture. The results showed that the major pyrolysates from α- and β-CBT were simple hydrocarbons, such as toluene, 1, 4-pentadiene, and p-xylene, as well as several important flavor compounds, such as 2-methylfuran, benzaldehyde, and 4-methylbenzaldehyde. More pyrolysis products were obtained at higher temperatures, and almost all of the harmful aromatic ingredients were produced at 900 °C. Importantly, solanone, a significant flavor component, was only obtained from the pyrolysis of α-CBT under 10% O2 in N2 at both 600 and 900 °C. The number of the pyrolysates changed with the change in pyrolysis temperature and the presence of oxygen. The study of the thermal behavior and pyrolysis products of these terpenoids could possibly suggest flavor precursors that could be used to provide specific flavors.

show abstract

Synthesis of α-ionyl-β-d-glucoside and its property of flavor release

Cited by 19 publications

References 18 publications

Glycosylation of bioactive C₁₃-apocarotenols inNicotiana benthamianaandMentha × piperita

Glycosylation of bioactive C₁₃-apocarotenols inNicotiana benthamianaandMentha × piperita

Controlled fragrance release from galactose-based pro-fragrances

Py-GC–MS Investigation of Pyrolysis Behaviors and Decomposition Products of α- and β-2,7,11-cembratriene-4,6-diols

Contact Info

Product

Resources

About

Synthesis of α-ionyl-β-d-glucoside and its property of flavor release

Cited by 19 publications

References 18 publications

Glycosylation of bioactive C13-apocarotenols inNicotiana benthamianaandMentha × piperita

Glycosylation of bioactive C13-apocarotenols inNicotiana benthamianaandMentha × piperita

Controlled fragrance release from galactose-based pro-fragrances

Py-GC–MS Investigation of Pyrolysis Behaviors and Decomposition Products of α- and β-2,7,11-cembratriene-4,6-diols

Contact Info

Product

Resources

About

Glycosylation of bioactive C₁₃-apocarotenols inNicotiana benthamianaandMentha × piperita

Glycosylation of bioactive C₁₃-apocarotenols inNicotiana benthamianaandMentha × piperita