On the biosynthetic origin of carminic acid

Silas Anselm Rasmussen, Kenneth Thermann Kongstad, Paiman Khorsand-Jamal, Rubini Maya Kannangara, Majse Nafisi, Alex Van Dam, Mads Bennedsen, Bjørn Madsen, Finn Okkels, Charlotte Held Gotfredsen, Dan Staerk, Ulf Thrane, Uffe Hasbro Mortensen, Thomas Ostenfeld Larsen, Rasmus John Normand Frandsen

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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 - May 2018

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., Bennedsen, M., Madsen, B., Okkels, F., Gotfredsen, C. H., Staerk, D., Thrane, U., Mortensen, U. H., Larsen, T. O., & 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