- Isolation of Salicin Derivatives from Homalium cochinchinensis and Their Antiviral Activities
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The chemical constituents of Homalium cochinchinensis were examined. From the root bark, in addition to the previously reported cochinolide and its β-glucopyranoside, cochinchiside A (1) and tremulacinol (4) were isolated together with three known compounds [benzoic acid, tremulacin (2), and tremuloidin (3)]. From the leaves, cochinchiside B (5) was isolated as new compound. The structures of the new compounds (1, 4, 5) were determined by spectroscopic and/or chemical methods. Antiviral testing of compounds 2-5 against HSV-1 and HSV-2 showed that tremulacin (2) and cochinchiside B (5) were weakly active. Tremulacin (2) was also weakly active against HIV-1.
- Ishikawa, Tsutomu,Nishigaya, Kaori,Takami, Kazuko,Uchikoshi, Hide,Chen, Ih-Sheng,Tsai, Ian-Lih
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Read Online
- Synthesis of Salicaceae Acetyl Salicins Using Selective Deacetylation and Acetyl Group Migration
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In the present work, the synthesis of acetylated salicins, which occur naturally in many Salicaceae species, is reported. The preparation of 2-O-acetylsalicin, 2-O-acetylchlorosalicin, and 2-O-acetylethylsalicin from peracetylated bromosalicin with selective acid-catalyzed deacetylation and one-pot nucleophilic substitution of bromine as the key steps is described. The base-catalyzed O-2 → O-6 acetyl migration afforded 6-O-acetylsalicin derivatives in good yields. Thus, the first synthesis of 6-O-acetylsalicin (fragilin) using acetyl group migration is reported as well as the synthesis of 6-O-acetylchlorosalicin and 6-O-acetylethylsalicin. The NaOMe-catalyzed deacetylation of acetylated glycosides gave salicin, chlorosalicin, and ethylsalicin recently reported from Alangium chinense.
- Romanova, Dariya A.,Avetyan, David L.,Belyanin, Maxim L.,Stepanova, Elena V.
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p. 888 - 893
(2020/03/30)
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- Stereocontrolled Synthesis of Phenolic α-d-Glycopyranosides
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Adopting the ‘remote activation concept’ toward stereocontrolled glycoside synthesis with minimal use of protection groups, a general synthesis of phenolic 1,2-cis glycopyranosides is reported, as exemplified by aryl α-d-galacto-, α-d-gluco- and 2-azido α-d-glucopyranosides among others using glycosyl donors bearing an anomeric (3-bromo-2-pyridyloxy) group and catalyzed by methyl triflate.
- St-Pierre, Gabrielle,Dafik, Laila,Klegraf, Ellen,Hanessian, Stephen
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p. 3575 - 3588
(2016/10/17)
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- Enzymatic resolution of (RS)-1-phenylalkyl β-D-glucosides to (R)-1-phenylalkyl β-primeverosides and (S)-1-phenylalkyl β-D-glucosides via plant xylosyltransferase
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The stereoselective xylosylation of (RS)-1-phenylalkyl β-D-glucosides was investigated using plant xylosyltransferase isolated from cultured Catharanthus roseus cells. Enzymatic xylosylation of (RS)-1-phenylethyl β-D-glucoside afforded (R)-1-phenylethyl β
- Shimoda, Kei,Katsuragi, Hisashi
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experimental part
p. 2060 - 2065
(2010/10/21)
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- Biotransformation of benzaldehyde-type and acetophenone-type derivatives by Pharbitis nil hairy roots
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The glucosylation of some coumarin and flavone derivatives on incubation with the hairy roots of morning glory (Pharbitis nil) was previously reported. We further studied the biotransformation of benzaldehyde- and acetophenone-type derivatives. Vanillin a
- Kanho, Hideki,Yaoya, Sayaka,Kawahara, Nobuo,Nakane, Takahisa,Takase, Yoichi,Masuda, Kazuo,Kuroyanagi, Masanori
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p. 361 - 365
(2007/10/03)
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- PHENOLIC GLUCOSIDES FROM THE HEARTWOOD OF PRUNUS GRAYANA
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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.
- Shimomura, Hiroko,Sashida, Yutaka,Yoshinari, Kiyoshi
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p. 1499 - 1502
(2007/10/02)
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- VOLATILE CONSTITUENTS OF BALSAM POPLAR: THE PHENOL GLYCOSIDE CONNECTION
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Key Word Index - Populus balsamifera; Salicaceae; balsam poplar; phenol glycosides; 6-hydroxycyclohex-2-enone; cyclohexan-1,2-dione; salicortin; trichocarpin; trichocarpigenin.The volatile metabolites of balsam poplar winter-domant buds are a complex array of mono- and sesquiterpenoids with 1,8-cineol, trans-nerolidol and (+)-(1R,1'R)-α-bisabolol being the major components.On the other hand the volatiles of internodes (stems between buds) consist mainly of salicaldehyde and (+)-6-hydroxycyclohexanone with minor amounts of cyclohexan-1,2-dione and an unidentified compound.This is the first report of these cyclohexanones as natural products; salicortin, a phenol glycoside, appears to be their biosynthetic precursor.A second phenol glycoside, trichocarpin, is present in poplar internodes; and it is the progenitor of trichocarpigenin (benzyl gentisate), an easily formed artifact.
- Mattes, Benjamin R.,Clausen, Thomas P.,Reichardt, Paul B.
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p. 1361 - 1366
(2007/10/02)
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