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MedKoo Cat#: 559009 | Name: Lumisterol
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Steroid compound produced when ergosterol is exposed to ultraviolet radiation.

Chemical Structure

Lumisterol
Lumisterol
CAS#474-69-1

Theoretical Analysis

MedKoo Cat#: 559009

Name: Lumisterol

CAS#: 474-69-1

Chemical Formula: C28H44O

Exact Mass: 396.3392

Molecular Weight: 396.66

Elemental Analysis: C, 84.79; H, 11.18; O, 4.03

Price and Availability

Size Price Availability Quantity
5mg USD 1,050.00 2 Weeks
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Related CAS #
No Data
Synonym
IUPAC/Chemical Name
(3S,9R,10S,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
InChi Key
DNVPQKQSNYMLRS-YAPGYIAOSA-N
InChi Code
InChI=1S/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,26+,27+,28+/m0/s1
SMILES Code
CC(C)[C@@H](C)\C=C\[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@@]4(C)[C@@H]3CC[C@]12C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Lumisterol (9β,10α-Ergosterol), a steroid compound, is the (9β,10α)-stereoisomer of Ergosterol (HY-N0181).
In vitro activity:
This study tested whether novel CYP11A1-derived vitamin D3- and lumisterol-hydroxyderivatives, including 1,25(OH)2D3, 20(OH)D3, 1,20(OH)2D3, 20,23(OH)2D3, 1,20,23(OH)3D3, lumisterol, 20(OH)L3, 22(OH)L3, 20,22(OH)2L3, and 24(OH)L3, can protect against UVB-induced damage in human epidermal keratinocytes. Treatment of cells with the above compounds at concentrations of 1 or 100 nM showed a dose-dependent reduction in oxidant formation. At 100 nM they inhibited the proliferation of cultured keratinocytes. Reference: Redox Biol. 2019 Jun;24:101206. https://pubmed.ncbi.nlm.nih.gov/31039479/
In vivo activity:
Here, LH-1, a kind of ergosterol from the secondary metabolites of the marine fungus Pestalotiopsis sp., was extracted, isolated, purified, and further investigated the biological activities against melanoma. In vivo mouse assays confirmed that LH-1 could suppress melanoma growth by inducing cell apoptosis and reducing cell proliferation, and it did not have any notable toxic effects on normal tissues. Reference: Front Microbiol. 2022 Oct 12;13:1008053. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9608767/

Preparing Stock Solutions

The following data is based on the product molecular weight 396.66 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Qayyum S, Mohammad T, Slominski RM, Hassan MI, Tuckey RC, Raman C, Slominski AT. Vitamin D and lumisterol novel metabolites can inhibit SARS-CoV-2 replication machinery enzymes. Am J Physiol Endocrinol Metab. 2021 Aug 1;321(2):E246-E251. doi: 10.1152/ajpendo.00174.2021. Epub 2021 Jun 28. PMID: 34181461; PMCID: PMC8328521. 2. Chaiprasongsuk A, Janjetovic Z, Kim TK, Jarrett SG, D'Orazio JA, Holick MF, Tang EKY, Tuckey RC, Panich U, Li W, Slominski AT. Protective effects of novel derivatives of vitamin D3 and lumisterol against UVB-induced damage in human keratinocytes involve activation of Nrf2 and p53 defense mechanisms. Redox Biol. 2019 Jun;24:101206. doi: 10.1016/j.redox.2019.101206. Epub 2019 Apr 20. PMID: 31039479; PMCID: PMC6488822. 3. Xia T, Lei H, Wang J, He Y, Wang H, Gao L, Qi T, Xiong X, Liu L, Zhu Y. Identification of an ergosterol derivative with anti-melanoma effect from the sponge-derived fungus Pestalotiopsis sp. XWS03F09. Front Microbiol. 2022 Oct 12;13:1008053. doi: 10.3389/fmicb.2022.1008053. PMID: 36312981; PMCID: PMC9608767. 4. Hu Z, Hu H, Hu Z, Zhong X, Guan Y, Zhao Y, Wang L, Ye L, Ming L, Riaz Rajoka MS, He Z, Wang Y, Song X. Sanguinarine, Isolated From Macleaya cordata, Exhibits Potent Antifungal Efficacy Against Candida albicans Through Inhibiting Ergosterol Synthesis. Front Microbiol. 2022 Jun 15;13:908461. doi: 10.3389/fmicb.2022.908461. PMID: 35783394; PMCID: PMC9240711.
In vitro protocol:
1. Qayyum S, Mohammad T, Slominski RM, Hassan MI, Tuckey RC, Raman C, Slominski AT. Vitamin D and lumisterol novel metabolites can inhibit SARS-CoV-2 replication machinery enzymes. Am J Physiol Endocrinol Metab. 2021 Aug 1;321(2):E246-E251. doi: 10.1152/ajpendo.00174.2021. Epub 2021 Jun 28. PMID: 34181461; PMCID: PMC8328521. 2. Chaiprasongsuk A, Janjetovic Z, Kim TK, Jarrett SG, D'Orazio JA, Holick MF, Tang EKY, Tuckey RC, Panich U, Li W, Slominski AT. Protective effects of novel derivatives of vitamin D3 and lumisterol against UVB-induced damage in human keratinocytes involve activation of Nrf2 and p53 defense mechanisms. Redox Biol. 2019 Jun;24:101206. doi: 10.1016/j.redox.2019.101206. Epub 2019 Apr 20. PMID: 31039479; PMCID: PMC6488822.
In vivo protocol:
1. Xia T, Lei H, Wang J, He Y, Wang H, Gao L, Qi T, Xiong X, Liu L, Zhu Y. Identification of an ergosterol derivative with anti-melanoma effect from the sponge-derived fungus Pestalotiopsis sp. XWS03F09. Front Microbiol. 2022 Oct 12;13:1008053. doi: 10.3389/fmicb.2022.1008053. PMID: 36312981; PMCID: PMC9608767. 2. Hu Z, Hu H, Hu Z, Zhong X, Guan Y, Zhao Y, Wang L, Ye L, Ming L, Riaz Rajoka MS, He Z, Wang Y, Song X. Sanguinarine, Isolated From Macleaya cordata, Exhibits Potent Antifungal Efficacy Against Candida albicans Through Inhibiting Ergosterol Synthesis. Front Microbiol. 2022 Jun 15;13:908461. doi: 10.3389/fmicb.2022.908461. PMID: 35783394; PMCID: PMC9240711.
1. Lumisterol to Tachysterol Photoisomerization in EPA Glass at 77 K. A Comparative Study PMID 28234492; The journal of physical chemistry. A 2017 Mar; 121(12):2331-2342 2.The Role of Classical and Novel Forms of Vitamin D in the Pathogenesis and Progression of Nonmelanoma Skin Cancers PMID 32918223; Advances in experimental medicine and biology 2020; 1268(?):257-2 3.Photoprotective Properties of Vitamin D and Lumisterol Hydroxyderivatives PMID 32441029; Cell biochemistry and biophysics 2020 Jun; 78(2):165-180 (Review Article) 4. Generation of potentially bioactive ergosterol-derived products following pulsed ultraviolet light exposure of mushrooms (Agaricus bisporus) PMID 22868105; Food chemistry 2012 Nov; 135(2):396-401

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