Detection of 7-Dehydrocholesterol and Vitamin D3 Derivatives in Honey

Tae-Kang Kim; Venkatram Atigadda; Pawel Brzeminski; Adrian Fabisiak; Edith K. Y. Tang; Robert C. Tuckey; Andrzej T. Slominski

doi:10.3390/molecules25112583

Molecules (Jun 2020)

Detection of 7-Dehydrocholesterol and Vitamin D3 Derivatives in Honey

Tae-Kang Kim,
Venkatram Atigadda,
Pawel Brzeminski,
Adrian Fabisiak,
Edith K. Y. Tang,
Robert C. Tuckey,
Andrzej T. Slominski

Affiliations

Tae-Kang Kim: Department of Dermatology, University of Alabama at Birmingham, Birmingham, AL 35294, USA
Venkatram Atigadda: Department of Dermatology, University of Alabama at Birmingham, Birmingham, AL 35294, USA
Pawel Brzeminski: Department of Dermatology, University of Alabama at Birmingham, Birmingham, AL 35294, USA
Adrian Fabisiak: Department of Dermatology, University of Alabama at Birmingham, Birmingham, AL 35294, USA
Edith K. Y. Tang: School of Molecular Sciences, The University of Western Australia, Perth, WA 6009, Australia
Robert C. Tuckey: School of Molecular Sciences, The University of Western Australia, Perth, WA 6009, Australia
Andrzej T. Slominski: Department of Dermatology, University of Alabama at Birmingham, Birmingham, AL 35294, USA

DOI: https://doi.org/10.3390/molecules25112583
Journal volume & issue: Vol. 25, no. 11
p. 2583

Abstract

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20(S)-Hydroxyvitamin D3 (20(OH)D3) is an endogenous metabolite produced by the action of CYP11A1 on the side chain of vitamin D3 (D3). 20(OH)D3 can be further hydroxylated by CYP11A1, CYP27A1, CYP24A1 and/or CYP27B1 to several hydroxyderivatives. CYP11A1 also hydroxylates D3 to 22-monohydroxyvitamin D3 (22(OH)D3), which is detectable in the epidermis. 20-Hydroxy-7-dehydrocholesterol (20(OH)-7DHC) has been detected in the human epidermis and can be phototransformed into 20(OH)D3 following the absorption of ultraviolet B (UVB) energy by the B-ring. 20(OH)D3 and its hydroxyderivatives have anti-inflammatory, pro-differentiation and anti-proliferative effects, comparable to 1,25-dihydroxyvitamin D3 (1,25(OH)2D3). Since cytochromes P450 with 20- or 25-hydroxylase activity are found in insects participating in ecdysone synthesis from 7-dehydrocholesterol (7DHC), we tested whether D3-hydroxyderivatives are present in honey, implying their production in bees. Honey was collected during summer in the Birmingham area of Alabama or purchased commercially and extracted and analyzed using LC-MS. We detected a clear peak of m/z = 423.324 [M + Na]+ for 20(OH)D3 corresponding to a concentration in honey of 256 ng/g. We also detected peaks of m/z = 383.331 [M + H − H2O]+ for 20(OH)-7DHC and 25(OH)D3 with retention times corresponding to the standards. We further detected species with m/z = 407.329 [M + Na]+ corresponding to the RT of 7DHC, D3 and lumisterol3 (L3). Similarly, peaks with m/z = 399.326 [M + H − H2O]+ were detected at the RT of 1,25(OH)2D3 and 1,20-dihydroxyvitamin D3 (1,20(OH)2D3). Species corresponding to 20-monohydroxylumisterol3 (20(OH)L3), 22-monohydroxyvitamin D3 (22(OH)D3), 20,23-dihydroxyvitamin D3 (20,23(OH)2D3), 20,24/25/26-dihydroxyvitamin D3 (20,24/25/26(OH)2D3) and 1,20,23/24/25/26-trihydroxyvitamin D3 (1,20,23/24/25/26(OH)3D3) were not detectable above the background. In conclusion, the presence of 7DHC and D3 and of species corresponding to 20(OH)-7DHC, 20(OH)D3, 1,20(OH)2D3, 25(OH)D3 and 1,25(OH)2D3 in honey implies their production in bees, although the precise biochemistry and photochemistry of these processes remain to be defined.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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