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Journal of Natural Products 2005-Oct

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

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Barbara Rogge
Yasuhiro Itagaki
Nathan Fishkin
Ester Levi
Ralph Rühl
San-San Yi
Koji Nakanishi
Ulrich Hammerling

Keywords

Abstract

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.

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