On the biosynthetic origin of carminic acid

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

doi:10.1016/j.ibmb.2018.03.002

On the biosynthetic origin of carminic acid

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

Section for Plant Biochemistry

4 Citations (Scopus)

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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

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On the biosynthetic origin of carminic acidFinal published version, 2.58 MBLicence: CC BY-NC-ND

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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. T., Gotfredsen, C. H., Stærk, 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 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.",

author = "Rasmussen, {Silas A.} 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 Okkels, {Finn T.} and Gotfredsen, {Charlotte H.} and Dan St{\ae}rk and Ulf Thrane and Mortensen, {Uffe H.} and Larsen, {Thomas O.} and Frandsen, {Rasmus J. N.}",

year = "2018",

month = may,

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

language = "English",

volume = "96",

pages = "51--61",

journal = "Insect Biochemistry and Molecular Biology",

issn = "0965-1748",

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T1 - On the biosynthetic origin of carminic acid

AU - Rasmussen, Silas A.

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 T.

AU - Gotfredsen, Charlotte H.

AU - Stærk, Dan

AU - Thrane, Ulf

AU - Mortensen, Uffe H.

AU - Larsen, Thomas O.

AU - Frandsen, Rasmus J. N.

PY - 2018/5

Y1 - 2018/5

N2 - 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.

AB - 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.

U2 - 10.1016/j.ibmb.2018.03.002

DO - 10.1016/j.ibmb.2018.03.002

M3 - Journal article

C2 - 29551461

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

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