title: Geleganidines A-C, Unusual Monoterpenoid Indole Alkaloids from Gelsemium elegans.
abstract: The first rotameric monoterpenoid indole alkaloids (MIAs), 1a and 1b, and two unusual dimeric MIAs, 2 and 3, with new dimerization patterns, together with their putative biosynthetic intermediates 4-7, were isolated from the roots of Gelsemium elegans. Compounds 2 and 3 represent the first natural aromatic azo- and the first urea-linked dimeric MIAs, respectively. Their structures and absolute configurations were elucidated by means of NMR spectroscopy, single-crystal X-ray diffraction, and electronic circular dichroism data analyses. The interconverting mechanism of rotamers 1a and 1b was studied by density functional theory computation. Compounds 2 and 3 showed moderate cytotoxic activity against MCF-7 and PC-12 cells, respectively. In addition, a plausible biosynthesis pathway for the new alkaloids was proposed on the basis of the coexistence of their biosynthetic precursors.
authors.affiliation: Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University , Guangzhou 510632, PR China.|Department of Natural Medicinal Chemistry, China Pharmaceutical University , Nanjing 210009, PR China.
authors.forename: Wei
authors.initials: W
authors.lastname: Zhang
authors.affiliation: Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University , Guangzhou 510632, PR China.
authors.forename: Xiao-Jun
authors.initials: XJ
authors.lastname: Huang
authors.affiliation: Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University , Guangzhou 510632, PR China.
authors.forename: Sheng-Yuan
authors.initials: SY
authors.lastname: Zhang
authors.affiliation: Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University , Guangzhou 510632, PR China.
authors.forename: Dong-Mei
authors.initials: DM
authors.lastname: Zhang
authors.affiliation: Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University , Guangzhou 510632, PR China.
authors.forename: Ren-Wang
authors.initials: RW
authors.lastname: Jiang
authors.affiliation: Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University , Guangzhou 510632, PR China.
authors.forename: Jian-Yang
authors.initials: JY
authors.lastname: Hu
authors.affiliation: Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University , Guangzhou 510632, PR China.
authors.forename: Xiao-Qi
authors.initials: XQ
authors.lastname: Zhang
authors.affiliation: Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University , Guangzhou 510632, PR China.
authors.forename: Lei
authors.initials: L
authors.lastname: Wang
authors.affiliation: Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University , Guangzhou 510632, PR China.|Department of Natural Medicinal Chemistry, China Pharmaceutical University , Nanjing 210009, PR China.
authors.forename: Wen-Cai
authors.initials: WC
authors.lastname: Ye
mesh_terms: D000818:Animals; D018360:Crystallography, X-Ray; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D031450:Gelsemium / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D016716:PC12 Cells; D018517:Plant Roots / Q000737:chemistry; D051381:Rats; D046948:Secologanin Tryptamine Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013778:Tetrazolium Salts / Q000493:pharmacokinetics; D013844:Thiazoles / Q000493:pharmacokinetics
chemical_list: D004365:Drugs, Chinese Herbal; D046948:Secologanin Tryptamine Alkaloids; D013778:Tetrazolium Salts; D013844:Thiazoles; C000603011:geleganidine A; C000603012:geleganidine B; C000603013:geleganidine C; C022616:thiazolyl blue