title: Synthesis of a novel phosphate analog of 20-hydroxylecdysone with potent hypoglycemic activity.
abstract: A novel, water-soluble 20-hydroxylecdysono-20,22-phosphoric acid 2 and its sodium salt 3 were designed and synthesized from 20-hydroxylecdysone 1 in six steps and with 67% overall yield. The synthesized phosphoric acid 2 exhibited hypoglycemic activity >40-fold more potent than that of 20-hydroxylecdysone 1 at concentrations between 2 × 10⁻⁷ and 2 × 10⁻⁸ mol/l in a glucose consumption test in HepG2 cells. At a concentration of 2 × 10⁻⁹ mol/l, phosphoric acid 2 was still active, causing a maximum increase in glucose consumption of more than 500%, while 20-hydroxylecdysone 1 was inactive.
authors.affiliation: Department of Medicinal Natural Products and Key Laboratory of Drug Targeting & Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy, Sichuan University, Chengdu, China.
authors.forename: Dan
authors.initials: D
authors.lastname: Zhang
authors.forename: Min
authors.initials: M
authors.lastname: Zhang
authors.forename: Bao
authors.initials: B
authors.lastname: Ding
authors.forename: Xiao-Lin
authors.initials: XL
authors.lastname: Wang
authors.forename: Zong-Yin
authors.initials: ZY
authors.lastname: Qiu
authors.forename: Yong
authors.initials: Y
authors.lastname: Qin
mesh_terms: D004440:Ecdysone / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D056945:Hep G2 Cells; D006801:Humans; D007004:Hypoglycemic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012995:Solubility; D014867:Water / Q000737:chemistry
chemical_list: C558550:20-hydroxylecdysono-20,22-phosphoric acid; D007004:Hypoglycemic Agents; D014867:Water; D004440:Ecdysone