Retinoylserine and retinoylalanine, 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, B, Itagaki, Y, Fishkin, N, Levi, E, Ruhl, R, Yi, S.S, Nakanishi, K, Hammerling, U
• Format: Article
• Language: English
• Subjects: alanine; Alanine - analogs & derivatives; Alanine - chemical synthesis; Alanine - chemistry; Alanine - isolation & purification; Animals; Biological and medical sciences; chemical structure; Chromatography; Fundamental and applied biological sciences. Psychology; Insecta; Invertebrates; Molecular Structure; moths; Moths - chemistry; Physiology. Development; retinoic acid; retinoylalanine; retinoylserine; serine; Serine - analogs & derivatives; Serine - chemical synthesis; Serine - chemistry; Serine - isolation & purification; spectral analysis; Spectrometry, Mass, Electrospray Ionization; Stereoisomerism; Tretinoin - analogs & derivatives; Tretinoin - chemical synthesis; Tretinoin - chemistry; Tretinoin - isolation & purification; Trichoplusia ni
• 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), 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.