- Total Syntheses and Anti-inflammatory Activities of Syringin and Its Natural Analogues
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Syringin (1), a natural bioactive glucoside isolated from the root of Acanthopanax senticosus (Rupr. Maxim.) Harms, possesses significant anti-inflammatory activity. In this study, we have accomplished the total syntheses of syringin (1), along with its natural analogues 2-12, from a common starting material, syringaldehyde (13), in 4-8 steps with an overall yields of 11.8-61.3%. The anti-inflammatory activities of these compounds were determined against NO production in the LPS-stimulated RAW264.7 cells. Among them, compounds 1-5, 7, and 9 exhibited different levels of anti-inflammatory activity.
- Dong, Hongbo,Du, Weihong,He, Yujiao,Shi, Zheng,Wang, Yingying,Wu, Min
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p. 2866 - 2874
(2021/11/12)
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- Secoiridoid Glucosides from the Twigs of Syringa oblata var. dilatata and Their Neuroprotective and Cytotoxic Activities
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Phytochemical investigation of the twigs of Syringa oblata var. diatata led to the isolation of two new secoiridoid glucosides, dilatioside A-B (1-2), along with thirteen known ones (3-15). The structures were determined by spectroscopic methods including
- Suh, Kyoung Jin,Suh, Won Se,Subedi, Lalita,Kim, Sun Yeou,Choi, Sang Un,Lee, Kang Ro
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p. 359 - 364
(2017/04/14)
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- Oxidation of monolignols by members of the berberine bridge enzyme family suggests a role in plant cell wall metabolism
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Plant genomes contain a large number of genes encoding for berberine bridge enzyme (BBE)-like enzymes. Despite the wide-spread occurrence and abundance of this protein family in the plant kingdom, the biochemical function remains largely unexplored. In this study, we have expressed two members of the BBE-like enzyme family from Arabidopsis thaliana in the host organism Komagataella pastoris. The two proteins, termed AtBBE-like 13 and AtBBE-like 15, were purified, and their catalytic properties were determined. In addition, AtBBE-like 15 was crystallized and structurally characterized by x-ray crystallography. Here, we show that the enzymes catalyze the oxidation of aromatic allylic alcohols, such as coumaryl, sinapyl, and coniferyl alcohol, to the corresponding aldehydes and that AtBBE-like 15 adopts the same fold as vanillyl alcohol oxidase as reported previously for berberine bridge enzyme and other FAD-dependent oxidoreductases. Further analysis of the substrate range identified coniferin, the glycosylated storage form of coniferyl alcohol, as a substrate of the enzymes, whereas other glycosylated monolignols were rather poor substrates. A detailed analysis of the motifs present in the active sites of the BBE-like enzymes in A. thaliana suggested that 14 out of 28 members of the family might catalyze similar reactions. Based on these findings, we propose a novel role of BBE-like enzymes in monolignol metabolism that was previously not recognized for this enzyme family.
- Daniel, Bastian,Pavkov-Keller, Tea,Steiner, Barbara,Dordic, Andela,Gutmann, Alexander,Nidetzky, Bernd,Sensen, Christoph W.,Van Der Graaff, Eric,Wallner, Silvia,Gruber, Karl,Macheroux, Peter
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p. 18770 - 18781
(2015/08/04)
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- Enzymatic and metabolic engineering for efficient production of syringin, sinapyl alcohol 4-O-glucoside, in Arabidopsis thaliana
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To promote efficient production of syringin, a plant-derived bioactive monolignol glucoside, synergistic effects of enzymatic and metabolic engineering were combined. Recombinant UGT72E3/E2 chimeras, generated by exchanging parts of the C-terminal domain including the Putative Secondary Plant Glycosyltransferase (PSPG) motif of UGT72E3 and UGT72E2, were expressed in leaves of transgenic Arabidopsis plants; syringin production was measured in vivo and by enzymatic assays in vitro. In both tests, UGT72E3/2 displayed substrate specificity for sinapyl alcohol like the parental enzyme UGT72E3, and the syringin production was significantly increased compared to UGT72E3. In particular, in the in vitro assay, which was performed in the presence of a high concentration of sinapyl alcohol, the production of syringin by UGT72E3/2 was 4-fold higher than by UGT72E3. Furthermore, to enhance metabolic flow through the phenylpropanoid pathway and maintain a high basal concentration of sinapyl alcohol in the leaves, UGT72E3/2 was combined with the sinapyl alcohol synthesis pathway gene F5H encoding ferulate 5-hydroxylase and the lignin biosynthesis transcriptional activator MYB58. The resulting UGT72E3/2+F5H+MYB58 OE plants, which simultaneously overexpress these three genes, accumulated a 56-fold higher level of syringin in their leaves than wild-type plants.
- Chu, Yang,Kwon, Tackmin,Nam, Jaesung
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- Coniferyl alcohol metabolism in conifers - I. Glucosidic turnover of cinnamyl aldehydes by UDPG: Coniferyl alcohol glucosyltransferase from pine cambium
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UDPG: coniferyl alcohol glucosyltransferase (CAGT; EC 2.4.1.111) isolated from cambial tissues of Pinus strobus was able to convert cinnamyl aldehydes as well as dihydroconiferyl alcohol into their corresponding 4-O-β-D-glucosides in vitro, Cinnamyl aldeh
- Steeves, Valerie,Foerster, Hartmut,Pommer, Ulrich,Savidge, Rodney
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p. 1085 - 1093
(2007/10/03)
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- Coniferin and derivatives: A fast and easy synthesis via the aldehyde series using phase-transfer catalysis
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Coniferin was synthesised in good yields (56% starting from vanillin) under mild conditions. A one-pot coupling of the glucosidation and Wittig- type reactions led to coniferaldehyde tetra-O-acetylglucoside, easily reduced into tetra-O-acetylconiferin by sodium borohydride. Similar procedures were used for the synthesis of syringin and the glucoside of 4-coumaryl alcohol.
- Daubresse, Nicolas,Francesch, Charlette,Mhamdi, Farida,Rolando, Christian
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p. 157 - 161
(2007/10/03)
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- PHENOLIC CONSTITUENTS OF PHELLODENDRON AMURENSE BARK
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Glycosides of (+/-)-5,5'-dimethoxyariciresinol, 2-(p-hydroxy-phenyl)-ethanol and N-methylhigenamine were isolated from the dried bark of Phellodendron amurense, together with nine phenolic compounds.
- Ida, Yoshiteru,Satih, Yohko,Ohtsuka, Masumi,Nagasao, Miki,Shoji, Junzo
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p. 209 - 216
(2007/10/02)
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- TANGSHENOSIDES I AND II FROM CHUAN-DANGSHEN, THE ROOT OF CODONOPSIS TANGSHEN OLIV.
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From the roots of Codonopsis tangshen (Chuan-dangshen) cultivated in Sichuan, China, two new phenylpropanoid glucosides named tangshenosides I and II were isolated together with syringin. the structures of both compounds including the absolute configurations were elucidated by physical and chemical procedures.KEYWORDS - codonopsis tangshen; Dangshen; Campanulaceae; Chinese folk medicine; tangshenoside I; tangshenoside II; syringin; phenylpropanoid glycoside;
- Mizutani, Kenji,Yuda, Masamichi,Tanaka, Osamu,Saruwatari, Yuh-ichiro,Jia, Ming-Ru,et al.
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p. 2726 - 2729
(2007/10/02)
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