61276-17-3Relevant articles and documents
An Approach to the Synthesis of Electron-Rich and Hindered Esters and Its Application to the Synthesis of Acteoside
Zhang, Xiaojuan,Yang, Yutong,Wang, Fuye,Zhou, Zhengbing,Zhang, Hongbin,Zhu, Yugen
supporting information, p. 9210 - 9215 (2021/11/30)
Electron-rich esters are ubiquitously distributed in natural products and play a central role in bioactivities. Herein, we disclose an efficient, mild, and general esterification approach to the synthesis of these esters by employing gold(I)-catalyzed acylation reaction with alkyne-tethered mixed anhydrides and alcohols. This method can be applied to ester-bond formation in complex substrates and facilitates efficient synthesis of acteoside, which belongs to the family of phenylethanoid glycosides and possesses a broad range of bioactivities.
Samioside, a new phenylethanoid glycoside with free-radical scavenging and antimicrobial activities from Phlomis samia
Kyriakopoulou,Magiatis,Skaltsounis,Aligiannis,Harvala
, p. 1095 - 1097 (2007/10/03)
A new phenylethanoid glycoside, samioside, was isolated from the aerial parts of Phlomis samia and identified as 1-O-3,4-(dihydroxyphenyl)ethyl β-D-apiofuranosyl-(1→4)-α-L-rhamnopyranosyl-(1→3)-4-O- caffeoyl-β-D-glucopyranoside (1). In addition, one known phenylethanoid glycoside and three known flavonoids were identified as acteoside (2), apigenin, chrysoeriol, and ermanin, respectively. The structure of 1 was elucidated on the basis of its spectroscopic data. Samioside (1) demonstrated scavenging properties toward the DPPH radical and antimicrobial activity against Gram-positive and -negative bacteria.
Synthesis of verbascoside: A dihydroxyphenylethyl glycoside with diverse bioactivity
Duynstee, Howard I.,De Koning, Martijn C.,Ovaa, Huib,Van Der Marel, Gijs A.,Van Boom, Jacques H.
, p. 2623 - 2632 (2007/10/03)
TMSOTf-mediated condensation of ethyl 4,6-O-benzylidene-1-thio-β-D- glucopyranoside (2) with peracetylated α-L-rhamnopyranosyl trichloroacetimidate donor 3a resulted in the formation of orthoester 4, which, after acetylation, rearranged into ethyl 3-O-(α-L-rhamnopyranosyl)-l- thio-β-D-glucopyranoside derivative 6a. The latter compound was converted into the corresponding trichloroacetimidate donors 8a-b. An alternative approach to trichloroacetimidate 8c commenced with the iodonium ion mediated glycosidation of ethyl 2,3,4-tri-O-benzoyl-1-thio-α-L-rhamnopyranside (15) with 1,2:5,6-diisopropylidene-D-glucofuranose (16) to afford disaccharide 17, which was transformed into 8c in five steps. Condensation of 8a-c with 2- [3,4-di-(tert-butyldimethylsilyloxy)phenyl]ethanol (12) gave, after deacylation, key intermediate 14. Protecting-group manipulation of 14 and subsequent esterification of resulting 22 with 3,4-di-O-tert- butyldimethylsilylcaffeic acid (27) gave, after deprotection, verbascoside (1).
PHENYLPROPANOID GLYCOSIDES OF Teucrium polium
Oganesyan, G. B.,Galstyan, A. M.,Mnatsakanyan, V. A.,Shashkov, A. S.,Agababyan, P. V.
, p. 556 - 559 (2007/10/02)
Together with poliumoside we have isolated for the first time from golden germander verbascoside and a new phenylpropanoid glycoside (teupolioside) for which the structure of 2-(3,4-dihydroxyphenyl)ethyl O-β-D-galactopyranosyl-(1->2)-O-α-L-rhamnopyranosyl-(1->3)-4-O-caffeoyl-β-D-glucopyranoside is proposed.A mixture of poliumoside and teupolioside revealed a moderate antibacterial activity.
NINE PHENETHYL ALCOHOL GLYCOSIDES FROM STACHYS SIEBOLDII
Nishimura, Hiroaki,Sasaki, Hiroshi,Inagaki, Nobuyuki,Chin, Masao,Zhengxiong, Chen,Mitsuhashi, Hiroshi
, p. 965 - 969 (2007/10/02)
Three new phenethyl alcohol glycosides together with six known compounds have been isolated from the leaves of Stachys sieboldii.On the basis of chemical and spectral analyses, the structures of three new compounds named stachysosides A, B and C have been established as 2-(3,4-dihydroxyphenyl)ethyl O-α-L-arabinopyranosyl-(1->2)-α-L-rhamnopyranosyl-(1->3)-4-O-E-caffeoyl-β-D-glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl O-α-L-arabinopyranosyl-(1->2)-α-L-rhamnopyranosyl-(1->3)-4-O-E-feruloyl-β-D-glucopyranoside and 2-(3-hydroxy-4-methoxyphenyl)ethyl O-α-L-arabinopranosyl-(1->2)-α-L-rhamnopyranosyl-(1->3)-4-O-E-feruloyl-β-D-glucopyranoside, respectively.
Constitutions of forsythosides F and G, new phenol glycosides of Forsythia viridissima stems
Endo, Katsuya,Takahashi, Kazuhiro
, p. 291 - 294 (2007/10/02)
Two new phenol glycosides forsythoside F (1) and forsythoside G (2) have been isolated from Forsythia viridissima stems and their structures were established based on the spectroscopic data and chemical transformations.D-2-O-methylapiose was for the first time characterized in the natural product.
PHENOLIC GLYCOSIDES FROM DISEASED ROOTS OF REHMANNIA GLUTINOSA VAR. PURPUREA
Shoyama, Yukihiro,Matsumoto, Masami,Nishioka, Itsuo
, p. 983 - 986 (2007/10/02)
A new caffeoyl glycoside was isolated from the methanolic extract of the diseased root of Rehmannia glutinosa together with acteoside.The structure of the new phenol glycoside was elucidated as 3,4-dihydroxy-β-phenethyl-O-α-L-rhamnopyranosyl-(1 -> 3)-O-β-D-galactopyranosyl-(1 -> 6)-4-O-caffeoyl-β-D-glucopyranoside by spectral and chemical evidence.These compounds were detected as stress compounds in the roots of Rehmannia glutinosa following microbial infection.They inhibited the growth of the two Pseudomonas species. - Key Word Index: Rehmannia glutinosa; Scrophulariaceae; caffeoyl glycoside of 3,4-dihydroxyphenethyl alcohol; stress compound; antimicrobial activity.
