title: Steroids glycosylated with both D- and L-arabinoses from the South China Sea gorgonian Dichotella gemmacea.
abstract: Three new 19-hydroxy steroidal glycosides, namely, junceellosides E-G (2-4), were isolated together with the known analogue junceelloside C (1) from the South China Sea gorgonian Dichotella gemmacea. The structures of these compounds were elucidated by a combination of detailed spectroscopic analyses, chemical methods, and comparison with reported data. These glycosides are found to have sugar moieties of both β-l- and β-d-arabinopyranoses by HPLC analysis of their thiocarbamoyl-thiazolidine derivatives and those of authentic d- and l-arabinoses, leading to the structure revision of junceelloside C (1). This is the first report of steroidal glycosides from the gorgonian D. gemmacea and the first report of glycosides with β-l-arabinopyranose from marine sources.
authors.affiliation: Research Center for Marine Drugs and Department of Pharmacology, School of Pharmacy, Second Military Medical University, 325 Guo-He Road, Shanghai 200433, People's Republic of China.
authors.forename: Mei
authors.initials: M
authors.lastname: Jiang
authors.forename: Peng
authors.initials: P
authors.lastname: Sun
authors.forename: Hua
authors.initials: H
authors.lastname: Tang
authors.forename: Bao-Shu
authors.initials: BS
authors.lastname: Liu
authors.forename: Tie-Jun
authors.initials: TJ
authors.lastname: Li
authors.forename: Cui
authors.initials: C
authors.lastname: Li
authors.forename: Wen
authors.initials: W
authors.lastname: Zhang
mesh_terms: D000818:Animals; D037421:Anthozoa / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001089:Arabinose / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006031:Glycosylation; D008386:Marine Biology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009792:Oceans and Seas; D013237:Stereoisomerism; D013256:Steroids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; D006027:Glycosides; D013256:Steroids; C582678:junceelloside C; D001089:Arabinose