Retinoylserine and retinoylalanine, new natural products of the moth, Trichoplusia ni

• Published in: Journal of natural products (Washington, D.C.) D.C.), 2005-10, Vol.68 (10), p.1536-1540
• Main Authors: Rogge, Barbara, Itagaki, Yasuhiro, Fishkin, Nathan, Levi, Ester, Rühl, Ralph, Yi, San-San, Nakanishi, Koji, Hammerling, Ulrich
• Format: Article
• Language: English
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np0496791

Insect cells convert vitamin A into a number of retinoids that are evolutionarily conserved with those of mammalian cells. However, insect cells also produce additional natural retinoids. Namely, two retinoic acid peptides, N- trans -retinoylserine ( 1 ) and N- trans -retinoylalanine ( 2 ) ( Figure 1 ), have been isolated from a cell line of the common cabbage looper, Trichoplusia ni . These are the first examples of naturally occurring retinoic acid linked to amino acids through an amide bond; the amino acid moieties are depicted in the more common L-configuration although the absolute configuration was not determined due to the minuscule sample amount.