title: Novel O-glycosidic gossypol isomers and their bioactivities.
abstract: Novel glycosidic gossypol analogs, 7,7'-gossypol diglucoside tetraacetate GS1, 6,7'-gossypol diglucoside tetraacetate GS2, 7,7'-gossypol diglycoside GS1', 6,7'-gossypol diglycoside GS2' were obtained by the ultrasound-assisted reaction of the potassium salt of gossypol with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide under PTC conditions and were fully characterized by 1D NMR ((1)H NMR, (13)C NMR, DEPT, 1D NOE), 2D NMR (HMBC, HMQC), FTIR, HRMS and HPLC. The anticancer activities, cytotoxic effects as well as anti-trypanosomal activities of these novel glycosidic gossypols were explored and suggest that gossypol glycosides could be used to develop new candidates for anticancer drugs and anti-trypanosomal agents.
authors.affiliation: Department of Food, Nutrition and Packaging Sciences, Clemson University, Clemson, SC 29634, USA.
authors.forename: Juanjuan
authors.initials: J
authors.lastname: Yin
authors.forename: Limei
authors.initials: L
authors.lastname: Jin
authors.forename: Feng
authors.initials: F
authors.lastname: Chen
authors.forename: Xi
authors.initials: X
authors.lastname: Wang
authors.forename: Alex
authors.initials: A
authors.lastname: Kitaygorodskiy
authors.forename: Yueming
authors.initials: Y
authors.lastname: Jiang
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000981:Antiprotozoal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D005947:Glucose / Q000031:analogs & derivatives / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry*; D006072:Gossypol / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D006868:Hydrolysis; D007536:Isomerism; D011188:Potassium / Q000737:chemistry; D014346:Trypanosoma brucei brucei / Q000187:drug effects; D014465:Ultrasonics
chemical_list: C529108:2,3,4,6-tetra-O-acetylglucopyranosyl bromide; D000970:Antineoplastic Agents; D000975:Antioxidants; D000981:Antiprotozoal Agents; D006027:Glycosides; D005947:Glucose; D006072:Gossypol; D011188:Potassium