title: Hyperuralones A and B, new acylphloroglucinol derivatives with intricately caged cores from Hypericum uralum.
abstract: Hyperuralone A (1), a polycyclic polyprenylated acylphloroglucinol possessing an unprecedented tetracyclo-[5.3.1.1(4,9).0(4,11)]-dodecane core, was characterized from Hypericum uralum together with hyperuralone B (2), a congener with another complex caged skeleton. Their structures were determined by extensive spectroscopic analysis and ECD calculations. A plausible biosynthetic pathway of their intriguing architectures via intramolecular Diels-Alder reactions was also proposed. Compound 1 exhibited obviously cytotoxic activities against five human cancer cell lines in vitro (IC50 4.6-14.4 μM).
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, Yunnan, P. R. China.
authors.forename: Jing-Jing
authors.initials: JJ
authors.lastname: Zhang
authors.forename: Jing
authors.initials: J
authors.lastname: Yang
authors.forename: Yang
authors.initials: Y
authors.lastname: Liao
authors.forename: Xing-Wei
authors.initials: XW
authors.lastname: Yang
authors.forename: Jun-Zeng
authors.initials: JZ
authors.lastname: Ma
authors.forename: Qiu-Li
authors.initials: QL
authors.lastname: Xiao
authors.forename: Li-Xin
authors.initials: LX
authors.lastname: Yang
authors.forename: Gang
authors.initials: G
authors.lastname: Xu
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D018922:HL-60 Cells; D006801:Humans; D020902:Hypericum / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010696:Phloroglucinol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology
chemical_list: D000972:Antineoplastic Agents, Phytogenic; C000599335:hyperuralone A; C000599336:hyperuralone B; D010696:Phloroglucinol