title: Caeruleanone A, a rotenoid with a new arrangement of the D-ring from the fruits of Millettia caerulea.
abstract: Caeruleanone A (1), a novel rotenoid with an unprecedented arrangement of the D-ring, was isolated with another two new analogues, caeruleanones B (2) and C (3), together with 11 known rotenoids from the fruits of Millettia caerulea. The structures of the new compounds were determined by spectroscopic data analysis, with that of 1 being confirmed by single-crystal X-ray diffraction. Compounds 2 and 3 displayed potent mitochondrial transmembrane potential inhibitory and quinone reductase induction activities.
authors.affiliation: Division of Medicinal Chemistry and Pharmacognosy, ‡Division of Pharmacy Practice and Administration, College of Pharmacy, §Department of Chemistry and Biochemistry, The Ohio State University , Columbus, Ohio 43210, United States.
authors.forename: Lynette
authors.initials: L
authors.lastname: Bueno Pérez
authors.forename: Li
authors.initials: L
authors.lastname: Pan
authors.forename: Ulyana
authors.initials: U
authors.lastname: Muñoz Acuña
authors.forename: Jie
authors.initials: J
authors.lastname: Li
authors.forename: Hee-Byung
authors.initials: HB
authors.lastname: Chai
authors.forename: Judith C
authors.initials: JC
authors.lastname: Gallucci
authors.forename: Tran Ngoc
authors.initials: TN
authors.lastname: Ninh
authors.forename: Esperanza J
authors.initials: EJ
authors.lastname: Carcache de Blanco
authors.forename: Djaja D
authors.initials: DD
authors.lastname: Soejarto
authors.forename: A Douglas
authors.initials: AD
authors.lastname: Kinghorn
mesh_terms: D005638:Fruit / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D033641:Millettia / Q000737:chemistry*; D008928:Mitochondria / Q000187:drug effects*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012402:Rotenone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: D006576:Heterocyclic Compounds, 4 or More Rings; C000588728:caeruleanone A; C000588727:caeruleanone B; C000588729:caeruleanone C; D012402:Rotenone