5Beta-Scymnol.
INCI name: Scymnol
| File:5beta Scymnol | |
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| IUPAC name
(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-17-[(2R,5R)-5,7-dihydroxy-6-(hydroxymethyl)heptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7,12-triol
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| ECHA InfoCard | Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). |
| E number | Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C27H48O6 | |
| Molar mass | 468.675 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
5Beta-Scymnol, also known as Scymnol, is a synthetic INCI-listed skin conditioning ingredient[1]. The molecule is a hydroxyl radical scavenger used for oily and combination skin. Manufactured synthetically, it is used for the treatment of skin blemishes such as blocked pores and acne. Published data has shown 5Beta-Scymnol to be a powerful antioxidant and free radical scavenger, which promotes the restoration of skin, protecting it from free radical damage associated with blemishes and acne.
History
The molecule was identified and isolated from shark tissues by Professor Takuo Kosuge, Shizuoka College of Pharmacy, Shizuoka, Japan during the 1980s. Kosuge screened hundreds of ingredients found in traditional Chinese medicine and tested each for efficacy and drug discovery using Western methods. Based on traditional usage, it was hypothesised the ingredient may be effective for the treatment of scalds, blemishes and acne.[2]
Clinical testing
Following Kosuge’s discovery, a sulfated form of Scymnol (Sodium Scymnol Sulfate, INCI name Isolutrol) was clinically evaluated for hyperseborrhea. This is a condition that occurs when the sebaceous glands (https://en.wikipedia.org/wiki/Sebaceous_gland) produce excess oil in the skin. In 1988 Dr Pierre Fabre (https://en.wikipedia.org/wiki/Pierre_Fabre_(businessman)) conducted a double-blind, placebo controlled clinical trial of 40 subjects which was published in La Gazette Medicale. The control group showed no change in skin oiliness but the Scymnol sulfate group had a near 40% reduction.[3]
Given Scymnol’s properties and the relationship between seborrhoea, skin oiliness and acne,[4] the molecule was further investigated for the treatment of acne. Dr David Fenton of St Thomas’ Hospital, London trialled a formulation containing Scymnol Sulfate over two months. 14 of the 15 participants showed improvement in their acne condition over the course of the trial. [5]
A comparative study of Sodium Scymnol Sulfate versus Benzoyl Peroxide was published in 1995. Sodium Scymnol Sulfate significantly improved patients’ acne by reducing the number of inflamed lesions. It did not significantly reduce the numbers of non-inflamed lesions. Fewer side effects were experienced by patients treated with Sodium Scymnol Sulfate than those treated with benzoyl peroxide. The study concluded Scymnol was a useful adjunct in the treatment of acne, particularly in patients with inflamed lesions.
Free Radicals’ role in acne
Free radicals are highly reactive, unstable oxygen-containing molecules that chemically react with other cells in the body. In doing so they cause destruction to cell membranes, proteins and DNA when stealing their electrons. This stealing process is called oxidation, and the damage caused by free radicals is called oxidative damage or oxidative stress. (wikipedia link to free radicals)
Research has shown that in acne the normal antioxidant defense system operations appear to be overwhelmed. Free radical damage and oxidative stress to the skin are implicated in development of acne vulgaris.[6]
Squalene, a component of sebum secreted by the sebaceous glands, is oxidised by free radicals which leads to inflammation and damage to surrounding tissues, and triggers the sebaceous glands to overproduce more sebum, which can exacerbate the acne condition. Acne pathogenesis is characterized by excessive sebum production, follicular epithelial hyperkeratosis, rupture of follicular epithelium, and colonization by P. acnes. Free radicals can be implicated in each of the abnormalities associated with acne vulgaris.[7]
Scymnol Mode of Action
5Beta-Scymnol is a powerful hydroxyl (OH) free radical scavenger, more potent than the known OH scavengers dimethyl sulfoxide and mannitol, the peroxyl radical scavenger Trolox, and markedly more potent than pycnogenol formulations.[8] Scymnol’s role in quenching free radicals may play a role in inhibiting acne. Scymnol’s hydroxyl radical scavenging properties also point to utility as an anti-aging cosmetic ingredient, given the role oxidative stress has in premature ageing of skin.
Scymnol’s ancient origins
Fossil records reveal sharks have been in existence for over 420 million years, long before the evolution of trees (360 million years) and dinosaurs (230 million years). There are over 1,000 species of sharks in existence today that have evolved through numerous mass extinction events and environmental changes. This evolutionary timescale has seen sharks develop numerous unique adaptations that are now the subject of scientific investigation. Scymnol is a unique bile alcohol that differs from that found in amphibians and mammals, in that it contains three OH- groups which accounts for its free radical scavenging properties. Sharks have exceptional disease resistance, wound healing and infection fighting abilities.[9]
Molecules that are unique to sharks have been identified and synthesised, showing antiviral and anti-angiogenic activity.[10]
References
- ↑ "INCI". Personal Care Products Council.
- ↑ Kosuge, Y., Kosuge, T., Tsuji, K., Ishida, H., and Broadbent, J. M. (1989). Scymnol sulphate salts isolated from shark tissues for the treatment of liver and skin ailments (Patent: PCTInt Appl. WO 8801274-C.I. CO7J31/ 00). Chem. Abslr. 110, 88640g
- ↑ Fabre, P. “Etude contrôlée, en double aveugle contre placebo, d'une lotion à base d'isolutrol dans le traitement de l'hyperséborrhée”, Gazette médicale de France No. 36, 27 October 1989
- ↑ Burton JL, Sbuster S. The relationship between seborrboea and acne vulgaris. Br. J. Dermatol. 1971; 84: 600-1.
- ↑ Isolutrol: A new agent in acne” D. Fenton, Guest Speaker: Australasian College of Dermatologists Annual Meeting (1992) Perth
- ↑ Welch M, Caughman A, Verdicchio RJ, et al. Addressing the role of free radical oxidation in the acne paradigm. Presented at: The 67th Annual Academy of Dermatology Meeting; March 6-10, 2009; San Francisco, California
- ↑ Mills et al, Addressing Free Radical Oxidation in Acne Vulgaris, J Clin Aesthet Dermatol. 2016 Jan; 9(1): 25–30
- ↑ Macrides et al, A comparison of the hydroxyl radical scavenging properties of the shark bile steroid 5 beta-scymnol and plant pycnogenols, Biochem Mol Biol Int. 1997 Sep;42(6):1249-60
- ↑ White shark genome reveals ancient elasmobranch adaptations associated with wound healing and the maintenance of genome stability Nicholas J. Marra, Michael J. Stanhope, Nathaniel K. Jue, Minghui Wang, Qi Sun, Paulina Pavinski Bitar, Vincent P. Richards, Aleksey Komissarov, Mike Rayko, Sergey Kliver, Bryce J. Stanhope, Chuck Winkler, Stephen J.O’Brien, Agostinho Antunes, Salvador Jorgensen, Mahmood S. Shivji Proceedings of the National Academy of Sciences Mar 2019, 116 (10) 4446-4455; DOI:10.1073/pnas.1819778116
- ↑ Zasloff M, Adams AP, Beckerman B, Campbell A, Han Z, Luijten E, Meza I, Julander J, Mishra A, Qu W, Taylor JM, Weaver SC, Wong GC. Squalamine as a broad-spectrum systemic antiviral agent with therapeutic potential. Proc Natl Acad Sci U S A. 2011 Sep 20;108(38):15978-83. doi: 10.1073/pnas.1108558108. Epub 2011 Sep 19. Erratum in: Proc Natl Acad Sci U S A. 2011 Nov 1;108(44):18186. PMID: 21930925; PMCID: PMC3179074.
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