156-38-7Relevant articles and documents
TARAXACOSIDE, A TYPE OF ACYLATED γ-BUTYROLACTONE GLYCOSIDE FROM TARAXACUM OFFICINALE
Rauwald, Hans-Willi,Huangs, Jai-Tung
, p. 1557 - 1560 (1985)
Key Word Index - Taraxacum officinale; Compositae; Chichoriaceae; roots; lactone glycoside; butyrolactone acylglycoside; glucose ester; p-hydroxyphenylacetic acid; taraxacoside; β-O--β-hydroxy-γ-butyrolactone. - In addition to the four new sesquiterpene lactones previously identified, a new acylated γ-butyrolactone glucoside, taraxacoside, was isolated from the roots of Taraxacum officinale.Its structure was elucidated mainly by 1H and 13C NMR studies as β-O--β-hydroxy-γ-butyrolactone.This seems to be the first instance of the detection of a monocyclic five-membered, saturated lactone O-glycoside.Additionally, p-hydroxyphenylacetic acid was identified for the first time as an acylating acid in a sugar ester.
In Situ Electrochemical Monitoring of Caged Compound Photochemistry: An Internal Actinometer for Substrate Release
Jarosova, Romana,Kaplan, Sam V.,Field, Thomas M.,Givens, Richard S.,Senadheera, Sanjeewa N.,Johnson, Michael A.
, p. 2776 - 2784 (2021)
Caged compounds are molecules that release a protective substrate to free a biologically active substrate upon treatment with light of sufficient energy and duration. A notable limitation of this approach is difficulty in determining the degree of photoactivation in tissues or opaque solutions because light reaching the desired location is obstructed. Here, we have addressed this issue by developing an in situ electrochemical method in which the amount of caged molecule photorelease is determined by fast-scan cyclic voltammetry (FSCV) at carbon-fiber microelectrodes. Using p-hydroxyphenyl glutamate (pHP-Glu) as our model system, we generated a linear calibration curve for oxidation of 4-hydroxyphenylacetic acid (4HPAA), the group from which the glutamate molecule leaves, up to a concentration of 1000 μM. Moreover, we are able to correct for the presence of residual pHP-Glu in solution as well as the light artifact that is produced. A corrected calibration curve was constructed by photoactivation of pHP-Glu in a 3 μL photoreaction vessel and subsequent analysis by high-performance liquid chromatography. This approach has yielded a linear relationship between 4HPAA concentration and oxidation current, allowing the determination of released glutamate independent of the amount of light reaching the chromophore. Moreover, we have successfully validated the newly developed method by in situ measurement in a whole, intact zebrafish brain. This work demonstrates for the first time the in situ electrochemical monitoring of caged compound photochemistry in brain tissue with FSCV, thus facilitating analyses of neuronal function.
PRODUCTION OF HYDROXYPHENYLETHANOL GLYCOSIDES IN SUSPENSION CULTURES OF SYRINGA VULGARIS
Ellis, B. E.
, p. 1941 - 1944 (1983)
Cell suspension cultures of Syringa vulgaris accumulate up to 16 percent of their dry wt as a mixture of hydroxyphenylethanol glycosides.The main component is the caffeoyl ester, verbascoside (acteoside).Tyrosine and tyramine are efficient biosynthetic precursors of the 4-hydroxy- and 3,4-dihydroxyphenylethanol moieties of these glycosides.Key Word Index- Syringa vulgaris; Oleaceae; lilac; cell cultures; biosynthesis; hydroxyphenylethanol glycosides; salidroside; verbascoside; caffeic acid.
p-Hydroxyphenacyl phototriggers: The reactive excited state of phosphate photorelease [26]
Conrad II, Peter G.,Givens, Richard S.,Hellrung, Bruno,Rajesh, Cheruvallil S.,Ramseier, Markus,Wirz, Jakob
, p. 9346 - 9347 (2000)
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A 'photorelease, catch and photorelease' strategy for bioconjugation utilizing a p-hydroxyphenacyl group
Madea,Slanina,Klán
, p. 12901 - 12904 (2016)
A bioorthogonal 'catch and photorelease' strategy, which combines alkyne-azide cycloaddition between p-hydroxyphenacyl azide and alkyne derivatives to form a 1,2,3-triazole adduct and subsequent photochemical release of the triazole moiety via a photo-Favorskii rearrangement, is introduced. The first step can also involve photorelease of a strained alkyne and its Cu-free click reaction with azide.
SESQUITERTENE LACTONES FROM LACTUCA LACINIATA
Nishimura, Keiichi,Miyase, Toshio,Ueno, Akira,Noro, Tadataka,Muroyanagi, Masanori,Fukushima, Seigo
, p. 2375 - 2380 (1986)
From the roots of Lactuca laciniata, six new sesquiterpene lactones, 9α-hydroxyzaluzanin C, 9α-hydroxy-11,13α-dihydrozaluzanin C, lactucopicriside, lactuside A and lactuside B, have been isolated together with known compounds, macrocliniside A, glucozaluzanin C, 11,13-α-dihydroglucozaluzanin C, 11,β,13-dihydrolactucin and dihydrosyntamarin.The structures were establishes by spectral data and X-ray diffraction analysis.Key Word Index - Lactuca laciniata; Compositae; sesquiterpene lactones; 9α-hydroxyzaluzanin C; 9α-hydroxy-11,13α-dihydrozaluzanin C; lactucopicriside; lactulide A; lactuside A; lactuside B.
Rapid biosynthesis of phenolic glycosides and their derivatives from biomass-derived hydroxycinnamates
Zhao, Mingtao,Hong, Xulin,Abdullah,Yao, Ruilian,Xiao, Yi
, p. 838 - 847 (2021/02/09)
Biomass-derived hydroxycinnamates (mainly includingp-coumaric acid and ferulic acid), which are natural sources of aromatic compounds, are highly underutilized resources. There is a need to upgrade them to make them economically feasible. Value-added phenolic glycosides and their derivatives, both belonging to a class of plant aromatic natural products, are widely used in the nutraceutical, pharmaceutical, and cosmetic industries. However, their complex aromatic structures make their efficient biosynthesis a challenging process. To overcome this issue, we created three novel synthetic cascades for the biosynthesis of phenolic glycosides (gastrodin, arbutin, and salidroside) and their derivatives (hydroquinone, tyrosol, hydroxytyrosol, and homovanillyl alcohol) fromp-coumaric acid and ferulic acid. Moreover, because the biomass-derived hydroxycinnamates directly provided aromatic units, the cascades enabled efficient biosynthesis. We achieved substantially high production rates (up to or above 100-fold enhancement) relative to the glucose-based biosynthesis. Given the ubiquity of the aromatic structure in natural products, the use of biomass-derived aromatics should facilitate the rapid biosynthesis of numerous aromatic natural products.
Efficient Synthesis of Phenylacetate and 2-Phenylethanol by Modular Cascade Biocatalysis
Mao, Zuoxi,Liu, Lijun,Zhang, Yang,Yuan, Jifeng
, p. 2676 - 2679 (2020/06/03)
The green and sustainable synthesis of chemicals from renewable feedstocks by a biotransformation approach has gained increasing attention in recent years. In this work, we developed enzymatic cascades to efficiently convert l-phenylalanine into 2-phenylethanol (2-PE) and phenylacetic acid (PAA), l-tyrosine into tyrosol (p-hydroxyphenylethanol, p-HPE) and p-hydroxyphenylacetic acid (p-HPAA). The enzymatic cascade was cast into an aromatic aldehyde formation module, followed by an aldehyde reduction module, or aldehyde oxidation module, to achieve one-pot biotransformation by using recombinant Escherichia coli. Biotransformation of 50 mM l-Phe produced 6.76 g/L PAA with more than 99 % conversion and 5.95 g/L of 2-PE with 97 % conversion. The bioconversion efficiencies of p-HPAA and p-HPE from l-Tyr reached to 88 and 94 %, respectively. In addition, m-fluoro-phenylalanine was further employed as an unnatural aromatic amino acid substrate to obtain m-fluoro-phenylacetic acid; '96 % conversion was achieved. Our results thus demonstrated high-yielding and potential industrial synthesis of above aromatic compounds by one-pot cascade biocatalysis.
