Absolute configuration of sesquiterpenes from Crossopetalum tonduzii and their inhibitory effects on Epstein-Barr virus early antigen activation in Raji cells.
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.
Jiménez
Ignacio A
IA
Instituto Universitario de Bio-Orgánica Antonio González, Universidad de La Laguna, Avenida Astrofísico Francisco Sánchez 2, La Laguna, 38206 Tenerife, Canary Islands, Spain.
Bazzocchi
Isabel L
IL
Núñez
Marvin J
MJ
Mukainaka
Teruo
T
Tokuda
Harukuni
H
Nishino
Hoyoku
H
Konoshima
Takao
T
Ravelo
Angel G
AG
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
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