title: Absolute configuration of sesquiterpenes from Crossopetalum tonduzii and their inhibitory effects on Epstein-Barr virus early antigen activation in Raji cells.
abstract: Two new sesquiterpenoids (1 and 2) with a dihydro-beta-agarofuran skeleton were isolated from Crossopetalum tonduzii. Their structures were elucidated on the basis of spectral analysis, including homonuclear and heteronuclear correlation NMR experiments (COSY, ROESY, HSQC, and HMBC). Their absolute configurations were determined by CD studies on 3, the benzoylated derivative of 1. Chemical correlations have allowed the absolute configurations of 4 and 5, two previously known dihydro-beta-agarofuran analogues, to be reported for the first time. Compounds 1, 2, and 5 showed strong antitumor-promoting effects on Epstein-Barr virus early antigen (EBV-EA) activation.
authors.affiliation: Instituto Universitario de Bio-Orgánica Antonio González, Universidad de La Laguna, Avenida Astrofísico Francisco Sánchez 2, La Laguna, 38206 Tenerife, Canary Islands, Spain.
authors.forename: Ignacio A
authors.initials: IA
authors.lastname: Jiménez
authors.forename: Isabel L
authors.initials: IL
authors.lastname: Bazzocchi
authors.forename: Marvin J
authors.initials: MJ
authors.lastname: Núñez
authors.forename: Teruo
authors.initials: T
authors.lastname: Mukainaka
authors.forename: Harukuni
authors.initials: H
authors.lastname: Tokuda
authors.forename: Hoyoku
authors.initials: H
authors.lastname: Nishino
authors.forename: Takao
authors.initials: T
authors.lastname: Konoshima
authors.forename: Angel G
authors.initials: AG
authors.lastname: Ravelo
mesh_terms: D000107:Acetylation; D016588:Anticarcinogenic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000956:Antigens, Viral / Q000187:drug effects*; D029753:Celastraceae / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010176:Panama; D010946:Plants, Medicinal / Q000737:chemistry*; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: C479723:(1R,2S,4S,5S,6R,7R,8S,9S,10S)-1,2-diacetoxy-9-benzoyloxy-15-(2-methylbutyroyloxy)-4,6,8-trihydroxydihydro-beta-agarofuran; C479721:(1R,2S,4S,5S,6R,7R,8S,9S,10S)-1,6,8-triacetoxy-9-benzoyloxy-15-(2-methylbutyroyloxy)-2,4-dihydroxydihydro-beta-agarofuran; D016588:Anticarcinogenic Agents; D000956:Antigens, Viral; C033305:Epstein-Barr virus early antigen; D012717:Sesquiterpenes