title: Chromane derivatives of small aromatic molecules: Chemoenzymatic synthesis and growth inhibitory activity on human tumor cell line LoVo WT.
abstract: Aromatic substrates tyrosol (p-hydroxyphenylethanol) and 2,6-dihydroxynaphthalene (2,6-DHN) were converted into chromane derivatives by means of chemoenzymatic reactions catalyzed by the aromatic prenyltransferase of bacterial origin NovQ, using dimethylallyl bromide as allylic substrate instead of the natural isoprenyl pyrophosphate substrate. Stereoselective prenylation occurred in o-position with respect to the phenol hydroxyl in both compounds. Prenylated derivatives were readily converted into chromane products via a selective 6-endo-trig cyclization involving the oxygen atom from the phenol moiety and the double bond of the prenyl substituent, a process catalyzed by FeCl(3). These findings set up the basis of a most convenient two-step, one-pot process which allows for easy recovery of the chromane products in high yields. The chromane derivatives thus obtained were tested for cytotoxicity and pro-apoptotic activity using LoVo WT cells, a line of human colon adenocarcinoma.
authors.affiliation: Dipartimento di Scienze Biochimiche, Sapienza Università di Roma, Italy.
authors.forename: Alberto
authors.initials: A
authors.lastname: Macone
authors.forename: Eugenio
authors.initials: E
authors.lastname: Lendaro
authors.forename: Alessandra
authors.initials: A
authors.lastname: Comandini
authors.forename: Irene
authors.initials: I
authors.lastname: Rovardi
authors.forename: Rosa Marina
authors.initials: RM
authors.lastname: Matarese
authors.forename: Antonio
authors.initials: A
authors.lastname: Carraturo
authors.forename: Alessandra
authors.initials: A
authors.lastname: Bonamore
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry* / Q000378:metabolism / Q000633:toxicity; D055162:Biocatalysis; D045744:Cell Line, Tumor; D002839:Chromans / Q000737:chemistry* / Q000633:toxicity; D003110:Colonic Neoplasms / Q000188:drug therapy; D004122:Dimethylallyltranstransferase / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*; D006131:Growth Inhibitors / Q000096:biosynthesis* / Q000737:chemistry / Q000633:toxicity; D006801:Humans; D011994:Recombinant Proteins / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism
chemical_list: D000970:Antineoplastic Agents; D002839:Chromans; D006131:Growth Inhibitors; D011994:Recombinant Proteins; D004122:Dimethylallyltranstransferase