84744-28-5Relevant articles and documents
Short Synthesis of Phenylpropanoid Glycosides Calceolarioside A and Syringalide B
Khong, Duc Thinh,Judeh, Zaher M. A.
, p. 1079 - 1083 (2018/05/01)
An efficient and practical three-step synthesis of phenylpropanoid glycosides calceolarioside A and syringalide B in >62% overall yield is disclosed. The key step involves the chemoselective and regio selective direct O -4 cinnamoylation of unprotected 2-phenylethyl-β- d -glucosides with cinnamic anhydrides using a chiral 4-pyrrolidinopyridine organocatalyst. This approach serves as a model for the short synthesis of phenylpropanoid glycosides acylated at O -4 without protection/deprotection steps.
Synthetic phenylethanoid glycoside derivatives as potent neuroprotective agents
Liu, Ying-Guo,Li, Xiaxi,Xiong, De-Cai,Yu, Binhan,Pu, Xiaoping,Ye, Xin-Shan
, p. 313 - 323 (2015/03/31)
Several phenylethanoid glycoside derivatives were designed and synthesized. Most of the synthetic compounds showed significant neuroprotective effects, including antioxidative and anti-apoptotic properties. Specifically, target compounds displayed potent effects against various toxicities such as H2O2 and 6-hydroxydopamine (6-OHDA) in PC12 cells. Among the synthetic derivatives, three compounds (5, 6, 8) exhibited much superior activities to the marketed drug Edaravone. The compounds were able to prevent the 6-OHDA-induced damage in PC12 cells in a dose-dependent manner. The anti-apoptotic effects could be observed via cell morphological changes. Moreover, the compounds significantly reduced the intracellular ROS increase resulting from 6-OHDA treatment. The preliminary structure-activity relationships were also explored. Compounds 5, 6, 8 may hold the potential as promising neuroprotective agents and new lead compounds for the treatment of neurodegenerative diseases or cerebral ischemia.
DES(RHAMNOSYL) ACTEOSIDE-CONTAINING OLIVE EXTRACT
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Paragraph 0054, (2014/12/09)
Foods and beverages, quasi-drugs, and pharmaceuticals that exhibit high antioxidative activity in the living body for a long time are provided. High antioxidative activity can be imparted by incorporating desrhamnosyl acteoside in an olive extract. A desr
A general synthetic strategy and the anti-proliferation properties on prostate cancer cell lines for natural phenylethanoid glycosides
Mulani, Shaheen K.,Guh, Jih-Hwa,Mong, Kwok-Kong Tony
, p. 2926 - 2937 (2014/05/06)
A general strategy for the synthesis of phenylethanoid glycosides (PhG) including echinacoside 1, acteoside 2, calceolarioside-A 3 and calceolarioside-B 4 is reported. The strategy features the application of low substrate concentration glycosylation and N-formyl morpholine modulated glycosylation methods for the construction of 1,2-trans β- and α-glycosidic bonds. The reported strategy does not invoke the use of the participatory acyl protecting function, which is incompatible with the ester function present in target PhG compounds. A preliminary study of the anti-proliferation properties of the PhG compounds 1-4 was performed; the acteoside 2 exhibited the best inhibition on the prostatic cancer cell proliferation. This journal is the Partner Organisations 2014.
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.
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.
FOUR CAFFEOYL GLYCOSIDES FROM CALLUS TISSUE OF REHMANNIA GLUTINOSA
Shoyama, Yukihiro,Matsumoto, Masami,Nishioka, Itsuo
, p. 1633 - 1636 (2007/10/02)
From the methanolic extract of callus tissue of Rehmannia glutinosa four phenolic glycosides and one aliphatic glycoside were isolated.Two of the phenolic glycosides were identified as acteoside and forsythiaside and the structures of the other two were elucidated as 3,4-dihydroxy-β-phenethyl-O-β-D-glucopyranosyl-(1->3)-4-O-caffeoyl-β-D-glucopyranosideand 3,4-dihydroxy-O-β-D-glucopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->6)-4-O-caffeoyl-β-D-glucopyranoside.
Verbascoside and Isoverbascoside from Paulownia Tomentosa Steud
Schilling, Gerhard,Huegel, Michael,Mayer, Walter
, p. 1633 - 1635 (2007/10/02)
The structure of verbascoside and isoverbascoside, isolated from the leaves of Paulownia tomentosa Steud. have been determined by NMR spectroscopy and partially hydrolysis to be β-(3,4-dihydroxyphenyl)ethyl-O-α-1-rhamnosyl(1-->3)-β-D-(4-O-caffeoyl)-glucopyranoside (1) and β-(3,4-dihydroxyphenyl)ethyl-O-α-L-rhamnosyl(1-->3)-β-D-(6-O-caffeoyl)-glucopyranoside (2). - Key words: Paulownia tomentosa Steud., Caffeoylglycoside, Verbascoside
