10019-60-0Relevant articles and documents
GLYCOSYLATION OF PHENOLIC COMPOUNDS BY ROOT CULTURE OF PANAX GINSENG
Ushiyama, Masashi,Furuya, Tsutomu
, p. 3009 - 3014 (1989)
A root culture of Panax ginseng was able to convert 3,5-dimethoxyphenol (taxicatigenin) into its glucoside (taxicatin), primeveroside and gentiobioside, methyl salicylate into its glucoside and gentiobioside, p-hydroxyacetophenone into its glucoside (picein), and coniferyl alcohol into dihydroconiferin propan-1-ol>.The conversion ratio and the excretion ratio of the conversion products from methyl salicylate were higher than those from the more polar p-hydroxyacetophenone, 3,5-dimethoxyphenol and coniferyl alcohol.Among the conversion products, in particular, the excretion ratio (ER) of a glucoside into the medium decreased in proportion to the quotient of substrate's Mr divided by its RRt on reversed phase HPLC (-ERMr/RRt).Key Word Index - Panax ginseng; Araliaceae; ginseng; root culture; biotransformation; glycosylation; glucoside; primeveroside; gentiobioside; 3,5-dimethoxyphenol; methyl salicylate; p-hydroxyacetophenone.
PHENOLIC GLUCOSIDES FROM THE HEARTWOOD OF PRUNUS GRAYANA
Shimomura, Hiroko,Sashida, Yutaka,Yoshinari, Kiyoshi
, p. 1499 - 1502 (1989)
Two new phenolic glucosides, pruyanaside A and pruyanaside B, have been isolated from the heartwood of Prunus grayana.Their structures have been shown by the spectral evidence to be 2'-β-D-glucopyranosyloxybenzyl 2-(6-O-benzoyl-β-D-glucopyranosyloxy)benzoate and 2'-(6-O-benzoyl-β-D-glucopyranosyloxy)benzyl 2-β-D-glucopyranosyloxy-6-hydroxdybenzoate. Key Word Index- Prunus grayana; Rosaceace; phenolic glucosides; salicin; populine; pruyanaside A; pruyanaside B; dehydrodicatechin A.
Scope of the DMC mediated glycosylation of unprotected sugars with phenols in aqueous solution
Fairbanks, Antony J.,Qiu, Xin
, p. 7355 - 7365 (2020)
Activation of reducing sugars in aqueous solution using 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and triethylamine in the presence of para-nitrophenol allows direct stereoselective conversion to the corresponding 1,2-Trans para-nitrophenyl glycosides without the need for any protecting groups. The reaction is applicable to sulfated and phosphorylated sugars, but not to ketoses or uronic acids or their derivatives. When applied to other phenols the product yield was found to depend on the pKa of the added phenol, and the process was less widely applicable to 2-Acetamido sugars. For 2-Acetamido substrates an alternative procedure in which the glycosyl oxazoline was pre-formed, the reaction mixture freeze-dried, and the crude product then reacted with an added phenol in a polar aprotic solvent system with microwave irradiation proved to be a useful simplification.
Molecular design and synthesis of novel salicyl glycoconjugates as elicitors against plant diseases
Cui, Zining,Ito, Jun,Dohi, Hirofumi,Amemiya, Yoshimiki,Nishida, Yoshihiro
, (2015/02/19)
A new series of salicyl glycoconjugates containing hydrazide and hydrazone moieties were designed and synthesized. The bioassay indicated that the novel compounds had no in vitro fungicidal activity but showed significant in vivo antifungal activity against the tested fungal pathogens. Some compounds even had superior activity than the commercial fungicides in greenhouse trial. The results of RT-PCR analysis showed that the designed salicyl glycoconjugates could induce the expression of LOX1 and Cs-AOS2, which are the specific marker genes of jasmonate signaling pathway, to trigger the plant defense resistance.
Molecular design, synthesis and bioactivity of glycosyl hydrazine and hydrazone derivatives: Notable effects of the sugar moiety
Cui, Zining,Yang, Xinling,Shi, Yanxia,Uzawa, Hirotaka,Cui, Jingrong,Dohi, Hirofumi,Nishida, Yoshihiro
experimental part, p. 7193 - 7196 (2012/02/02)
Assuming that the water solubility of our previous hydrazone derivatives would improve after modification with sugars while keeping or modulating their notable biological activities, we designed and synthesized some glycosyl hydrazine and hydrazone derivatives. Bioassay results indicated that the antitumor activity of our previously prepared hydrazones reduced or disappeared after modification with sugars. On the contrary, some glycosyl derivatives displayed much better antifungal activity against selected fungi. Obviously, a small sugar can change the biological activity of hydrazones significantly.
