ergocalciferol

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Ergocalciferol may be used as a vitamin D supplement, whereas cholecalciferol (vitamin D₃) is produced naturally by the skin when exposed to ultraviolet light.{{cite journal | vauthors = Holick MF, Binkley NC, Bischoff-Ferrari HA, Gordon CM, Hanley DA, Heaney RP, Murad MH, Weaver CM | display-authors = 6 | title = Evaluation, treatment, and prevention of vitamin D deficiency: an Endocrine Society clinical practice guideline | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 96 | issue = 7 | pages = 1911–1930 | date = July 2011 | pmid = 21646368 | doi = 10.1210/jc.2011-0385 | doi-access = free }} Ergocalciferol (D₂) and cholecalciferol (D₃) are considered to be equivalent for vitamin D production, as both forms appear to have similar efficacy in ameliorating rickets{{cite journal | vauthors = Thacher TD, Fischer PR, Obadofin MO, Levine MA, Singh RJ, Pettifor JM | title = Comparison of metabolism of vitamins D2 and D3 in children with nutritional rickets | journal = Journal of Bone and Mineral Research | volume = 25 | issue = 9 | pages = 1988–1995 | date = September 2010 | pmid = 20499377 | pmc = 3153403 | doi = 10.1002/jbmr.99 }} and reducing the incidence of falls in elderly patients.{{cite journal | vauthors = Fosnight SM, Zafirau WJ, Hazelett SE | title = Vitamin D supplementation to prevent falls in the elderly: evidence and practical considerations | journal = Pharmacotherapy | volume = 28 | issue = 2 | pages = 225–234 | date = February 2008 | pmid = 18225968 | doi = 10.1592/phco.28.2.225 | s2cid = 37034292 | doi-access = free }} Conflicting reports exist, however, concerning the relative effectiveness, with some studies suggesting that ergocalciferol has less efficacy based on limitations in absorption, binding, and inactivation.{{cite journal | vauthors = Tripkovic L, Lambert H, Hart K, Smith CP, Bucca G, Penson S, Chope G, Hyppönen E, Berry J, Vieth R, Lanham-New S | display-authors = 6 | title = Comparison of vitamin D2 and vitamin D3 supplementation in raising serum 25-hydroxyvitamin D status: a systematic review and meta-analysis | journal = The American Journal of Clinical Nutrition | volume = 95 | issue = 6 | pages = 1357–1364 | date = June 2012 | pmid = 22552031 | pmc = 3349454 | doi = 10.3945/ajcn.111.031070 }} A meta-analysis concluded that evidence usually favors cholecalciferol in raising vitamin D levels in blood, although it stated more research is needed.

Ergocalciferol is a secosteroid formed by a photochemical bond breaking of a steroid, specifically, by the action of ultraviolet light (UV-B or UV-C) on ergosterol, a form of provitamin D₂.{{cite journal | vauthors = Cardwell G, Bornman JF, James AP, Black LJ | title = A Review of Mushrooms as a Potential Source of Dietary Vitamin D | journal = Nutrients | volume = 10 | issue = 10 | page = 1498 | date = October 2018 | pmid = 30322118 | pmc = 6213178 | doi = 10.3390/nu10101498 | doi-access = free }}

Like cholecalciferol, ergocalciferol is inactive by itself. It requires two hydroxylations to become active: the first in the liver by CYP2R1 to form 25-hydroxyergocalciferol (ercalcidiol or 25-OH D₂{{cite journal | vauthors = Suda T, DeLuca HF, Schnoes H, Blunt JW | title = 25-hydroxyergocalciferol: a biologically active metabolite of vitamin D2 | journal = Biochemical and Biophysical Research Communications | volume = 35 | issue = 2 | pages = 182–185 | date = April 1969 | pmid = 5305760 | doi = 10.1016/0006-291X(69)90264-2 }}), and the second in the kidney by CYP27B1, to form the active 1,25-dihydroxyergocalciferol (ercalcitriol or 1,25-(OH)₂D₂), which activates the vitamin D receptor.{{cite journal | vauthors = | title = IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN): Nomenclature of vitamin D. Recommendations 1981 | journal = European Journal of Biochemistry | volume = 124 | issue = 2 | pages = 223–227 | date = May 1982 | pmid = 7094913 | doi = 10.1111/j.1432-1033.1982.tb06581.x | doi-access = free }} Unlike cholecalciferol, 25-hydroxylation is not performed by CYP27A1 for ergocalciferol.

Ergocalciferol and metabolites have lower affinity to the vitamin D-binding protein compared to the D₃ counterparts. The binding affinity of ercalcitriol to the vitamin D receptor is similar to that of calcitriol.{{cite journal | vauthors = Bikle DD | title = Vitamin D metabolism, mechanism of action, and clinical applications | journal = Chemistry & Biology | volume = 21 | issue = 3 | pages = 319–329 | date = March 2014 | pmid = 24529992 | pmc = 3968073 | doi = 10.1016/j.chembiol.2013.12.016 }} Ergocalciferol itself and metabolites can be deactivated by 24-hydroxylation.{{cite journal | vauthors = Houghton LA, Vieth R | title = The case against ergocalciferol (vitamin D2) as a vitamin supplement | journal = The American Journal of Clinical Nutrition | volume = 84 | issue = 4 | pages = 694–697 | date = October 2006 | pmid = 17023693 | doi = 10.1093/ajcn/84.4.694 | doi-access = free }}

Fungus, from USDA nutrient database (per 100g), D₂ + D₃:{{cite web |url=http://www.nal.usda.gov/fnic/foodcomp/search/index.html |title=USDA nutrient database – use the keyword 'portabello' and then click submit |url-status=live |archive-url=https://web.archive.org/web/20150222164135/http://www.nal.usda.gov/fnic/foodcomp/search/index.html |archive-date=22 February 2015 }}{{cite web|author=Haytowitz DB|title=Vitamin D in mushrooms|url=https://www.ars.usda.gov/ARSUserFiles/80400525/Articles/AICR09_Mushroom_VitD.pdf|publisher=Nutrient Data Laboratory, US Department of Agriculture|access-date=16 April 2018|date=2009|archive-date=1 February 2021|archive-url=https://web.archive.org/web/20210201181749/https://www.ars.usda.gov/ARSUserFiles/80400525/Articles/AICR09_Mushroom_VitD.pdf|url-status=live}}

• Mushrooms, Agaricus bisporus:
• raw portobello: 0.3 μg (10 IU); exposed to ultraviolet light: 11.2 μg (446 IU)
• raw crimini: 0.1 μg (3 IU); exposed to ultraviolet light: 31.9 μg (1276 IU)
• Mushrooms, shiitake:
• raw: Vitamin D (D₂ + D₃): 0.4 μg (18 IU)
• dried: Vitamin D (D₂ + D₃): 3.9 μg (154 IU)

Lichen

• Cladina arbuscula specimens grown under different natural conditions contain provitamin D₂ and vitamin D₂, ranges 89–146 and 0.22–0.55 μg/g dry matter respectively. They also contain vitamin D₃ (range 0.67 to 2.04 μg/g) although provitamin D₃ could not be detected. Vitamin D levels correlate positively with UV irradiation.

Plantae

• Alfalfa (Medicago sativa subsp. sativa), shoot: 4.8 μg (192 IU) vitamin D₂, 0.1 μg (4 IU) vitamin D₃{{cite web |url=http://sun.ars-grin.gov:8080/npgspub/xsql/duke/plantdisp.xsql?taxon=606 |title=Dr. Duke's Phytochemical and Ethnobotanical Databases |url-status=dead |archive-url=https://web.archive.org/web/20151016051622/http://sun.ars-grin.gov:8080/npgspub/xsql/duke/plantdisp.xsql?taxon=606 |archive-date=16 October 2015 }}

The vitamin D₂ content in mushrooms and C. arbuscula increase with exposure to ultraviolet light.{{cite journal | vauthors = Wang T, Bengtsson G, Kärnefelt I, Björn LO | title = Provitamins and vitamins D₂and D₃in Cladina spp. over a latitudinal gradient: possible correlation with UV levels | journal = Journal of Photochemistry and Photobiology. B, Biology | volume = 62 | issue = 1–2 | pages = 118–122 | date = September 2001 | pmid = 11693362 | doi = 10.1016/S1011-1344(01)00160-9 | url = http://lup.lub.lu.se/record/133512 | access-date = 27 January 2019 | url-status = live | archive-url = https://web.archive.org/web/20200528231009/https://lup.lub.lu.se/search/publication/133512 | archive-date = 28 May 2020 }}{{cite web|author=Haytowitz DB|title=Vitamin D in mushrooms|url=https://www.ars.usda.gov/ARSUserFiles/80400525/Articles/AICR09_Mushroom_VitD.pdf|publisher=Nutrient Data Laboratory, US Department of Agriculture|access-date=16 April 2018|date=2009|archive-date=1 February 2021|archive-url=https://web.archive.org/web/20210201181749/https://www.ars.usda.gov/ARSUserFiles/80400525/Articles/AICR09_Mushroom_VitD.pdf|url-status=live}} Ergosterol (provitamin D₂) found in these fungi is converted to previtamin D₂ on UV exposure, which then turns into vitamin D₂. As cultured mushrooms are generally grown in darkness, less vitamin D₂ is found compared to those grown in the wild or dried in the sun.

When fresh mushrooms or dried powders are purposely exposed to ultraviolet light, vitamin D₂ levels can be concentrated to much higher levels.{{cite journal | vauthors = Keegan RJ, Lu Z, Bogusz JM, Williams JE, Holick MF | title = Photobiology of vitamin D in mushrooms and its bioavailability in humans | journal = Dermato-Endocrinology | volume = 5 | issue = 1 | pages = 165–176 | date = January 2013 | pmid = 24494050 | pmc = 3897585 | doi = 10.4161/derm.23321 }}{{cite journal | vauthors = Simon RR, Borzelleca JF, DeLuca HF, Weaver CM | title = Safety assessment of the post-harvest treatment of button mushrooms (Agaricus bisporus) using ultraviolet light | journal = Food and Chemical Toxicology | volume = 56 | pages = 278–289 | date = June 2013 | pmid = 23485617 | doi = 10.1016/j.fct.2013.02.009 }} The irradiation procedure does not cause significant discoloration, or whitening, of mushrooms.{{cite journal | vauthors = Koyyalamudi SR, Jeong SC, Song CH, Cho KY, Pang G | title = Vitamin D2 formation and bioavailability from Agaricus bisporus button mushrooms treated with ultraviolet irradiation | journal = Journal of Agricultural and Food Chemistry | volume = 57 | issue = 8 | pages = 3351–3355 | date = April 2009 | pmid = 19281276 | doi = 10.1021/jf803908q | bibcode = 2009JAFC...57.3351K }} Claims have been made that a normal serving (approx. 2 oz or 60 grams) of fresh mushrooms treated with ultraviolet light have increased vitamin D content to levels up to 80 micrograms or 3200 IU if exposed to just five minutes of UV light after being harvested.{{Cite news |title=Bringing Mushrooms Out of the Dark |date=18 April 2006 |url=http://www.nbcnews.com/id/12370708 |work=NBC News |access-date=6 August 2007 |archive-date=7 November 2017 |archive-url=https://web.archive.org/web/20171107112253/http://www.nbcnews.com/id/12370708 |url-status=dead }}

Button mushrooms with enhanced vitamin D₂ content produced this way functions similarly to a vitamin D₂ supplement; both effectively improves vitamin D status.{{cite journal | vauthors = Urbain P, Singler F, Ihorst G, Biesalski HK, Bertz H | title = Bioavailability of vitamin D₂ from UV-B-irradiated button mushrooms in healthy adults deficient in serum 25-hydroxyvitamin D: a randomized controlled trial | journal = European Journal of Clinical Nutrition | volume = 65 | issue = 8 | pages = 965–971 | date = August 2011 | pmid = 21540874 | doi = 10.1038/ejcn.2011.53 | doi-access = free }} Vitamin D₂ from UV-irradiated yeast baked into bread or mushrooms is bioavailable and increases blood levels of 25(OH)D.

Viosterol, the name given to early preparations of irradiated ergosterol, is essentially synonymous with ergocalciferol.{{cite journal | date = 1930 | title = Viosterol official name for irradiated ergosterol | journal = Journal of Chemical Education | volume = 7 | issue = 1 | pages = 166 | doi = 10.1021/ed007p166 | last1 = Science Service | bibcode = 1930JChEd...7..166S }}See "Viosterol" and "Calciferol" at Merriam-Webster Medical Dictionary, e.g., {{cite web |url=http://www.merriam-webster.com/medical/viosterol |title=Medical Definition of VIOSTEROL |access-date=10 July 2014 |url-status=live |archive-url=https://web.archive.org/web/20140714154919/http://www.merriam-webster.com/medical/viosterol |archive-date=14 July 2014 }} and {{cite web |url=http://www.merriam-webster.com/medical/calciferol |title=Definition of CALCIFEROL |access-date=10 July 2014 |url-status=live |archive-url=https://web.archive.org/web/20140714212827/http://www.merriam-webster.com/medical/calciferol |archive-date=14 July 2014 }}, accessed 10 July 2014. However, currently, Viosterol is also the brand name for cholecalciferol (vitamin D₃) in some countries.{{cite web |url=https://www.vademecum.es/equivalencia-lista-viosterol+comprimido+5000+ui-uruguay-a11cc05--uy_1 |title=Viosterol comprimido 5000 UI |access-date=5 September 2022 |archive-date=5 September 2022 |archive-url=https://web.archive.org/web/20220905231617/https://www.vademecum.es/equivalencia-lista-viosterol+comprimido+5000+ui-uruguay-a11cc05--uy_1 |url-status=dead }}{{cite web |url=https://www-eticos-com-py.translate.goog//producto/247/viosterol-1000?_x_tr_sch=http&_x_tr_sl=es&_x_tr_tl=en&_x_tr_hl=en&_x_tr_pto=wapp |title=Viosterol 1000 |access-date=6 September 2022 |archive-date=6 September 2022 |archive-url=https://web.archive.org/web/20220906000655/https://www-eticos-com-py.translate.goog//producto/247/viosterol-1000?_x_tr_sch=http&_x_tr_sl=es&_x_tr_tl=en&_x_tr_hl=en&_x_tr_pto=wapp |url-status=dead }}

Ergocalciferol is manufactured and sold under various brand names, including Deltalin (Eli Lilly and Company), Drisdol (Sanofi-Synthelabo), and Calcidol (Patrin Pharma).{{cn|date=August 2024}}

{{reflist}}

• [https://webbook.nist.gov/cgi/cbook.cgi?ID=C50146 NIST Chemistry WebBook page for ergocalciferol]

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