Synthesis and cellular effects of cycloterpenals: cyclohexadienal-based activators of neurite outgrowth.
An unusual class of diterpenoid natural products, 'cycloterpenals' (with a central cyclohexadienal core), that arise in nature by condensation of retinoids and other isoprenes, have been isolated from a variety of organisms including marine sponges as well as from the human eye. A milk whey protein has also demonstrated the formation of a cycloterpenal derived from beta-ionylidineacetaldehyde. Here, we generate a synthetic library of these molecules where we detail reaction conditions required to effect cross condensation of alpha,beta-unsaturated aldehydes as opposed to homodimerization. The ability of this class of molecules to activate neurite outgrowth activity is reported.
Bench
Bennie J
BJ
Department of Chemistry, Texas A&M University, TAMU-3255, College Station, TX 77843, USA.
Tichy
Shane E
SE
Perez
Lisa M
LM
Benson
Jenna
J
Watanabe
Coran M H
CM
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D002454:Cell Differentiation / Q000187:drug effects; D053138:Cyclohexenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D019169:Jurkat Cells; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D016501:Neurites / Q000187:drug effects*; D016716:PC12 Cells; D051381:Rats; D021241:Spectrometry, Mass, Electrospray Ionization
D000447:Aldehydes; D053138:Cyclohexenes