Retinoylserine and retinoylalanine, natural products of the moth Trichoplusia ni Journal Article
| Authors: | Rogge, B.; Itagaki, Y.; Fishkin, N.; Levi, E.; Rühl, R.; Yi, S. S.; Nakanishi, K.; Hammerling, U. |
| Article Title: | Retinoylserine and retinoylalanine, natural products of the moth Trichoplusia ni |
| Abstract: | Insect cells convert vitamin A into a number of retinoids that are evolutionary 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. © 2005 American Chemical Society and American Society of Pharmacognosy. |
| Keywords: | signal transduction; controlled study; unclassified drug; nonhuman; animal cell; mammalia; animals; serine; culture medium; animalia; biosynthesis; nuclear magnetic resonance spectroscopy; amino acid; chemical structure; molecular structure; alanine; retinol; natural product; structure analysis; retinoic acid; genetic conservation; stereochemistry; proton nuclear magnetic resonance; stereoisomerism; chemical bond; amide; amino acid analysis; extraction; peptide derivative; insect cell; electrospray mass spectrometry; tretinoin; amino acid synthesis; light absorption; spectrometry, mass, electrospray ionization; lepidoptera; serine derivative; chromatography; moths; moth; retinoid derivative; vitamin metabolism; alanine derivative; retinoic acid derivative; retinoylalanine; retinoylserine; insect cell culture; trichoplusia ni; insecta |
| Journal Title: | Journal of Natural Products |
| Volume: | 68 |
| Issue: | 10 |
| ISSN: | 0163-3864 |
| Publisher: | American Chemical Society |
| Date Published: | 2005-10-01 |
| Start Page: | 1536 |
| End Page: | 1540 |
| Language: | English |
| DOI: | 10.1021/np0496791 |
| PUBMED: | 16252921 |
| PROVIDER: | scopus |
| PMCID: | PMC2532592 |
| DOI/URL: | |
| Notes: | --- - "Export Date: 24 October 2012" - "CODEN: JNPRD" - "Source: Scopus" |
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