title: "Mirror-image" manipulation of curdione stereoisomer scaffolds by chemical and biological approaches: development of a sesquiterpenoid library.
abstract: The sesquiterpenoid curdione is one of the main bioactive components in the essential oil of Rhizoma Curcumae (Curcuma wenyujin, Curcuma phaeocaulis, and Curcuma kwangsiensis), which has been clinically used for the treatment of cancer in mainland China. Recently it was reported that natural curdione could be hydroxylated by Aspergillus niger and transferred to its corresponding curcumalactones under acidic conditions. Based on this study, the development of a sesquiterpenoid library through the "mirror-image" manipulation of bioactive (non)natural curdione scaffolds by chemical and biological approaches is presented herein. A. niger induced the hydroxylation of two pairs of curdione enantiomers, yielding the corresponding mirror-image hydroxylated curdiones. Simultaneously, the acid-mediated intramolecular "ene" rearrangements of these curdiones and hydroxylated curdione enantiomers yielded the corresponding mirror-image curcumalactones and hydroxylated curcumalactones. Among the 16 pairs of enantiomers obtained in this study, 23 compounds are new sesquiterpenoids. These curdione and curcumalactone derivatives are of particular interest, as they have the potential to be used as lead compounds and scaffolds in drug discovery.
authors: School of Life Science and Biopharmaceutical Sciences and ‡School of Pharmaceutical Engineering, Shenyang Pharmaceutical University , Shenyang 110016, People's Republic of China.
authors: Bin
authors: B
authors: Qin
authors: Yuxin
authors: Y
authors: Li
authors: Lingxin
authors: L
authors: Meng
authors: Jingping
authors: J
authors: Ouyang
authors: Danni
authors: D
authors: Jin
authors: Lei
authors: L
authors: Wu
authors: Xin
authors: X
authors: Zhang
authors: Xian
authors: X
authors: Jia
authors: Song
authors: S
authors: You
mesh_terms: D001234:Aspergillus niger / Q000378:metabolism; D002681:China; D020650:Combinatorial Chemistry Techniques; D030024:Curcuma / Q000737:chemistry*; D055808:Drug Discovery; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009822:Oils, Volatile / Q000737:chemistry*; D027343:Rhizome / Q000737:chemistry; D012717:Sesquiterpenes; D045788:Sesquiterpenes, Germacrane / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D009822:Oils, Volatile; D012717:Sesquiterpenes; D045788:Sesquiterpenes, Germacrane; C577164:curcumalactone; C504126:curdione