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

doi:10.1016/j.ibmb.2018.03.002

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 language	English
Journal	Insect Biochemistry and Molecular Biology
Volume	96
Pages (from-to)	51-61
Number of pages	11
ISSN	0965-1748
DOIs	https://doi.org/10.1016/j.ibmb.2018.03.002
Publication status	Published - May 2018

Keywords

Anthraquinones
Biosynthesis
Carmine
Carminic acid
Coccid pigment
Dactylopius coccus
Insects
Polyketide

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Open Access articleFinal published version, 2.58 MBLicence: CC BY-NC-ND 4.0

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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

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title = "On the biosynthetic origin of carminic acid",

abstract = "The chemical composition of the scale insect Dactylopius coccus was analyzed with the aim to discover newpossible intermediates in the biosynthesis of carminic acid. UPLC-DAD/HRMS analyses of fresh and dried insectsresulted in the identification of three novel carminic acid analogues and the verification of several previouslydescribed 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 adetailed biosynthetic scheme that accounts for the formation of carminic acid (CA) in D. coccus and all describedcoccid pigments which share a flavokermesic acid (FK) core. Detection of coccid pigment intermediates inmembers of the Planococcus (mealybugs) and Pseudaulacaspis genera shows that the ability to form these pigmentsis taxonomically more widely spread than previously documented. The shared core-FK-biosyntheticpathway and wider taxonomic distribution suggests a common evolutionary origin for the trait in all coccid dyeproducing insect species.",

keywords = "Anthraquinones, Biosynthesis, Carmine, Carminic acid, Coccid pigment, Dactylopius coccus, Insects, Polyketide",

author = "Rasmussen, {Silas Anselm} and Kongstad, {Kenneth Thermann} and Paiman Khorsand-Jamal and Kannangara, {Rubini Maya} and Majse Nafisi and {Van Dam}, Alex and Mads Bennedsen and Bj{\o}rn Madsen and Finn Okkels and Gotfredsen, {Charlotte Held} and Dan Staerk and Ulf Thrane and Mortensen, {Uffe Hasbro} and Larsen, {Thomas Ostenfeld} and Frandsen, {Rasmus John Normand}",

year = "2018",

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doi = "10.1016/j.ibmb.2018.03.002",

language = "English",

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pages = "51--61",

journal = "Insect Biochemistry and Molecular Biology",

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AU - Rasmussen, Silas Anselm

AU - Kongstad, Kenneth Thermann

AU - Khorsand-Jamal, Paiman

AU - Kannangara, Rubini Maya

AU - Nafisi, Majse

AU - Van Dam, Alex

AU - Bennedsen, Mads

AU - Madsen, Bjørn

AU - Okkels, Finn

AU - Gotfredsen, Charlotte Held

AU - Staerk, Dan

AU - Thrane, Ulf

AU - Mortensen, Uffe Hasbro

AU - Larsen, Thomas Ostenfeld

AU - Frandsen, Rasmus John Normand

PY - 2018/5

Y1 - 2018/5

N2 - The chemical composition of the scale insect Dactylopius coccus was analyzed with the aim to discover newpossible intermediates in the biosynthesis of carminic acid. UPLC-DAD/HRMS analyses of fresh and dried insectsresulted in the identification of three novel carminic acid analogues and the verification of several previouslydescribed 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 adetailed biosynthetic scheme that accounts for the formation of carminic acid (CA) in D. coccus and all describedcoccid pigments which share a flavokermesic acid (FK) core. Detection of coccid pigment intermediates inmembers of the Planococcus (mealybugs) and Pseudaulacaspis genera shows that the ability to form these pigmentsis taxonomically more widely spread than previously documented. The shared core-FK-biosyntheticpathway and wider taxonomic distribution suggests a common evolutionary origin for the trait in all coccid dyeproducing insect species.

AB - The chemical composition of the scale insect Dactylopius coccus was analyzed with the aim to discover newpossible intermediates in the biosynthesis of carminic acid. UPLC-DAD/HRMS analyses of fresh and dried insectsresulted in the identification of three novel carminic acid analogues and the verification of several previouslydescribed 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 adetailed biosynthetic scheme that accounts for the formation of carminic acid (CA) in D. coccus and all describedcoccid pigments which share a flavokermesic acid (FK) core. Detection of coccid pigment intermediates inmembers of the Planococcus (mealybugs) and Pseudaulacaspis genera shows that the ability to form these pigmentsis taxonomically more widely spread than previously documented. The shared core-FK-biosyntheticpathway and wider taxonomic distribution suggests a common evolutionary origin for the trait in all coccid dyeproducing insect species.

KW - Anthraquinones

KW - Biosynthesis

KW - Carmine

KW - Carminic acid

KW - Coccid pigment

KW - Dactylopius coccus

KW - Insects

KW - Polyketide

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U2 - 10.1016/j.ibmb.2018.03.002

DO - 10.1016/j.ibmb.2018.03.002

M3 - Journal article

SN - 0965-1748

VL - 96

SP - 51

EP - 61

JO - Insect Biochemistry and Molecular Biology

JF - Insect Biochemistry and Molecular Biology

ER -

On the biosynthetic origin of carminic acid

Abstract

Keywords

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