title: γ-Hydroxynitrile glucosides from the seeds of Prinsepia utilis.
abstract: γ-Hydroxynitrile glucosides (prinsepicyanosides A-E) were isolated alongside 11 known compounds from seeds of Prinsepia utilis Royle. Their structures were determined by detailed analysis of NMR and MS spectroscopic data. The relative configuration of prinsepicyanoside C was established by Cu-Kα X-ray crystallography. Prinsepicyanoside A, osmaronin, and 4-(hydroxylmethyl)-5H-furan-2-one exhibited borderline antibacterial activity against Salmonella gallinarum, Vibrio parahaemolyticus, and Vibrio cholera with MIC values of 30.1, 20.7, and 22.8μg/mL, respectively.
authors: School of Pharmacy, Shanghai Jiao Tong University, Shanghai, PR China; Department of Pharmacy, Wuxi Infectious Disease Hospital, Wuxi, Jiangsu Province, PR China.
authors: Bin
authors: B
authors: Guan
authors: Key Laboratory of Animal Parasitology, Ministry of Agriculture, Shanghai Veterinary Research Institute, Shanghai, PR China.
authors: Tao
authors: T
authors: Li
authors: Department of Natural Product Chemistry, School of Pharmacy, Second Military Medical University, Shanghai, PR China.
authors: Xi-Ke
authors: XK
authors: Xu
authors: School of Pharmacy, Shanghai Jiao Tong University, Shanghai, PR China.
authors: Xu-Feng
authors: XF
authors: Zhang
authors: School of Pharmacy, Shanghai Jiao Tong University, Shanghai, PR China.
authors: Pan-Lei
authors: PL
authors: Wei
authors: School of Pharmacy, Shanghai Jiao Tong University, Shanghai, PR China.
authors: Cheng-Cheng
authors: CC
authors: Peng
authors: School of Pharmacy, Shanghai Jiao Tong University, Shanghai, PR China.
authors: Jian-Jun
authors: JJ
authors: Fu
authors: School of Pharmacy, Shanghai Jiao Tong University, Shanghai, PR China.
authors: Qi
authors: Q
authors: Zeng
authors: School of Pharmacy, Shanghai Jiao Tong University, Shanghai, PR China.
authors: Xiang-Rong
authors: XR
authors: Cheng
authors: School of Pharmacy, Shanghai Jiao Tong University, Shanghai, PR China.
authors: Shou-De
authors: SD
authors: Zhang
authors: School of Pharmacy, Shanghai Jiao Tong University, Shanghai, PR China.
authors: Shi-Kai
authors: SK
authors: Yan
authors: School of Pharmacy, Shanghai Jiao Tong University, Shanghai, PR China. Electronic address: kimhz@sjtu.edu.cn.
authors: Hui-Zi
authors: HZ
authors: Jin
authors: School of Pharmacy, Shanghai Jiao Tong University, Shanghai, PR China; Department of Natural Product Chemistry, School of Pharmacy, Second Military Medical University, Shanghai, PR China. Electronic address: wdzhangy@hotmail.com.
authors: Wei-Dong
authors: WD
authors: Zhang
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018360:Crystallography, X-Ray; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005663:Furans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry / Q000302:isolation & purification*; D019906:Nuclear Magnetic Resonance, Biomolecular; D027824:Rosaceae / Q000737:chemistry*; D012475:Salmonella / Q000187:drug effects; D012639:Seeds / Q000737:chemistry*; D013237:Stereoisomerism; D014733:Vibrio / Q000187:drug effects
chemical_list: D000900:Anti-Bacterial Agents; D004365:Drugs, Chinese Herbal; D005663:Furans; D005960:Glucosides; D009570:Nitriles; C000594520:prinsepicyanoside A
keywords: Antibacterial activity; Prinsepia utilis Royle; Rosaceae; γ-Hydroxynitrile glucosides