title: A general synthetic strategy and the anti-proliferation properties on prostate cancer cell lines for natural phenylethanoid glycosides.
abstract: 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.
authors.affiliation: Applied Chemistry Department, National Chiao Tung University of Taiwan, 1001, Ta Hsueh Road, Hsinchu, Taiwan, Republic of China. tmong@mail.ncut.edu.tw.
authors.forename: Shaheen K
authors.initials: SK
authors.lastname: Mulani
authors.forename: Jih-Hwa
authors.initials: JH
authors.lastname: Guh
authors.forename: Kwok-Kong Tony
authors.initials: KK
authors.lastname: Mong
mesh_terms: D002109:Caffeic Acids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002625:Chemistry, Organic / Q000379:methods*; D005960:Glucosides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D008297:Male; D010636:Phenols / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D010626:Phenylethyl Alcohol / Q000737:chemistry / Q000494:pharmacology*; D011471:Prostatic Neoplasms / Q000473:pathology*; D059808:Polyphenols
chemical_list: D002109:Caffeic Acids; D005960:Glucosides; D006027:Glycosides; D010636:Phenols; D010626:Phenylethyl Alcohol; C529019:calceolarioside B; C058956:acteoside; D059808:Polyphenols; C083066:calceolarioside A; C060297:echinacoside