title: Total Syntheses of (-)-Spirooliganones A and B and Their Diastereoisomers: Absolute Stereochemistry and Inhibitory Activity against Coxsackie Virus B3.
abstract: To investigate the effects of configuration on bioactivity, spirooliganones A and B and their six diastereoisomers (1-8) were synthesized in 11 steps. The key benzopyran core was assembled by intermolecular [4 + 2] hetero-Diels-Alder cycloaddition between (-)-sabinene and o-quinone methide, which was generated from the corresponding o-hydroxybenzyl alcohol. After establishing the absolute configuration, the inhibitory activities of spirooliganones 1-8 against Coxsackie virus B3 were evaluated, and the primary structure-activity relationships were analyzed. Compound 3 was the most potent compound, with an IC50 of 0.41 μM.
authors.affiliation: †State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China.
authors.forename: Nan
authors.initials: N
authors.lastname: Zhao
authors.affiliation: †State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China.
authors.forename: Xiaodong
authors.initials: X
authors.lastname: Ren
authors.affiliation: †State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China.
authors.forename: Jinhong
authors.initials: J
authors.lastname: Ren
authors.affiliation: †State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China.
authors.forename: Haining
authors.initials: H
authors.lastname: Lü
authors.affiliation: †State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China.
authors.forename: Shuanggang
authors.initials: S
authors.lastname: Ma
authors.affiliation: ‡Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China.
authors.forename: Rongmei
authors.initials: R
authors.lastname: Gao
authors.affiliation: ‡Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China.
authors.forename: Yuhuan
authors.initials: Y
authors.lastname: Li
authors.affiliation: †State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China.
authors.forename: Song
authors.initials: S
authors.lastname: Xu
authors.affiliation: †State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China.
authors.forename: Li
authors.initials: L
authors.lastname: Li
authors.affiliation: †State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China.
authors.forename: Shishan
authors.initials: S
authors.lastname: Yu
mesh_terms: D000081008:Bicyclic Monoterpenes; D061565:Cycloaddition Reaction; D029822:Enterovirus B, Human / Q000737:chemistry* / Q000187:drug effects*; D045563:Indolequinones / Q000737:chemistry*; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D039821:Monoterpenes / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000081008:Bicyclic Monoterpenes; D045563:Indolequinones; D039821:Monoterpenes; D013141:Spiro Compounds; C586354:spirooliganone A; C068040:quinone methide; C035127:sabinene