On the biosynthetic origin of carminic acid

Silas A. Rasmussen, Kenneth T Kongstad, Paiman Khorsand-Jamal, Rubini Maya Kannangara, Majse Nafisi, Alex Van Dam, Mads Bennedsen, Bjørn Madsen, Finn Okkels, Charlotte H. Gotfredsen, Dan Stærk, Ulf Thrane, Uffe H. Mortensen, Thomas O. Larsen, Rasmus J. N. Frandsen*

*Corresponding author for this work

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Abstract

The chemical composition of the scale insect Dactylopius coccus was analyzed with the aim to discover new possible intermediates in the biosynthesis of carminic acid. UPLC-DAD/HRMS analyses of fresh and dried insects resulted in the identification of three novel carminic acid analogues and the verification of several previously described intermediates. Structural elucidation revealed that the three novel compounds were desoxyerythrolaccin-O-glucosyl (DE-O-Glcp), 5,6-didehydroxyerythrolaccin 3-O-β-D-glucopyranoside (DDE-3-O-Glcp), and flavokermesic acid anthrone (FKA). The finding of FKA in D. coccus provides solid evidence of a polyketide, rather than a shikimate, origin of coccid pigments. Based on the newly identified compounds, we present a detailed biosynthetic scheme that accounts for the formation of carminic acid (CA) in D. coccus and all described coccid pigments which share a flavokermesic acid (FK) core. Detection of coccid pigment intermediates in members of the Planococcus (mealybugs) and Pseudaulacaspis genera shows that the ability to form these pigments is taxonomically more widely spread than previously documented. The shared core-FK-biosynthetic pathway and wider taxonomic distribution suggests a common evolutionary origin for the trait in all coccid dye producing insect species.
Original languageEnglish
JournalInsect Biochemistry and Molecular Biology
Volume96
Pages (from-to)51-61
Number of pages11
ISSN0965-1748
DOIs
Publication statusPublished - 2018

Bibliographical note

© 2018 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/BY-NC-ND/4.0/)

Keywords

  • Anthraquinones
  • Biosynthesis
  • Carmine
  • Carminic acid
  • Coccid pigment
  • Dactylopius coccus
  • Insects
  • Polyketide

Cite this

Rasmussen, S. A., Kongstad, K. T., Khorsand-Jamal, P., Kannangara, R. M., Nafisi, M., Van Dam, A., ... Frandsen, R. J. N. (2018). On the biosynthetic origin of carminic acid. Insect Biochemistry and Molecular Biology, 96, 51-61. https://doi.org/10.1016/j.ibmb.2018.03.002