title: Generation of structurally novel short carotenoids and study of their biological activity.
abstract: Recent research interest in phytochemicals has consistently driven the efforts in the metabolic engineering field toward microbial production of various carotenoids. In spite of systematic studies, the possibility of using C30 carotenoids as biologically functional compounds has not been explored thus far. Here, we generated 13 novel structures of C30 carotenoids and one C35 carotenoid, including acyclic, monocyclic, and bicyclic structures, through directed evolution and combinatorial biosynthesis, in Escherichia coli. Measurement of radical scavenging activity of various C30 carotenoid structures revealed that acyclic C30 carotenoids showed higher radical scavenging activity than did DL-α-tocopherol. We could assume high potential biological activity of the novel structures of C30 carotenoids as well, based on the neuronal differentiation activity observed for the monocyclic C30 carotenoid 4,4'-diapotorulene on rat bone marrow mesenchymal stem cells. Our results demonstrate that a series of structurally novel carotenoids possessing biologically beneficial properties can be synthesized in E. coli.
authors.affiliation: The Novo Nordisk Foundation Center for Biosustainability, Technical University of Denmark, Kogle Alle 6, 2970 Hørsholm, Denmark.
authors.forename: Se H
authors.initials: SH
authors.lastname: Kim
authors.affiliation: Department of Molecular Science and Technology and Department of Applied Chemistry and Biological Engineering, Ajou University, Woncheon-dong, Yeongtong-gu, Suwon 443-749, South Korea.
authors.forename: Moon S
authors.initials: MS
authors.lastname: Kim
authors.affiliation: Department of Molecular Science and Technology and Department of Applied Chemistry and Biological Engineering, Ajou University, Woncheon-dong, Yeongtong-gu, Suwon 443-749, South Korea.
authors.forename: Bun Y
authors.initials: BY
authors.lastname: Lee
authors.affiliation: Department of Molecular Science and Technology and Department of Applied Chemistry and Biological Engineering, Ajou University, Woncheon-dong, Yeongtong-gu, Suwon 443-749, South Korea.
authors.forename: Pyung C
authors.initials: PC
authors.lastname: Lee
mesh_terms: D000818:Animals; D001713:Biphenyl Compounds / Q000037:antagonists & inhibitors*; D001854:Bone Marrow Cells / Q000166:cytology / Q000187:drug effects / Q000378:metabolism; D002338:Carotenoids / Q000096:biosynthesis* / Q000737:chemistry / Q000494:pharmacology; D002454:Cell Differentiation / Q000187:drug effects*; D004305:Dose-Response Relationship, Drug; D004926:Escherichia coli / Q000235:genetics / Q000378:metabolism*; D016166:Free Radical Scavengers / Q000378:metabolism / Q000494:pharmacology; D005609:Free Radicals / Q000037:antagonists & inhibitors*; D059630:Mesenchymal Stem Cells / Q000166:cytology / Q000187:drug effects / Q000378:metabolism; D060847:Metabolic Engineering; D009474:Neurons / Q000166:cytology / Q000187:drug effects / Q000378:metabolism; D010851:Picrates / Q000037:antagonists & inhibitors*; D051381:Rats; D013329:Structure-Activity Relationship; D024502:alpha-Tocopherol / Q000494:pharmacology
chemical_list: D001713:Biphenyl Compounds; D016166:Free Radical Scavengers; D005609:Free Radicals; D010851:Picrates; D002338:Carotenoids; C004931:1,1-diphenyl-2-picrylhydrazyl; D024502:alpha-Tocopherol