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MedKoo Cat#: 573110 | Name: Aloesin
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Description:

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

Aloesin is a competitive tyrosinase inhibitor. As an Aloe chromone, Aloesin has previously been formulated with an aloe polysaccharide to give a composition called Loesyn, where it showed significant impact in reducing glycosylated hemoglobin, fasting blood glucose, fructosamine and plasma insulin level in humans. This molecule has also been shown to modulate melanogenesis and have some anti-inflammatory effects in rats.

Chemical Structure

Aloesin
CAS#30861-27-9

Theoretical Analysis

MedKoo Cat#: 573110

Name: Aloesin

CAS#: 30861-27-9

Chemical Formula: C19H22O9

Exact Mass: 394.1264

Molecular Weight: 394.38

Elemental Analysis: C, 57.87; H, 5.62; O, 36.51

Price and Availability

Size Price Availability Quantity
1mg USD 350.00 2 Weeks
5mg USD 850.00 2 Weeks
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Related CAS #
No Data
Synonym
Aloesin, Aloe resin B, Aloeresin B
IUPAC/Chemical Name
4H-1-Benzopyran-4-one, 8-beta-D-glucopyranosyl-7-hydroxy-5-methyl-2-(2-oxopropyl)-
InChi Key
HKIKAXXIWJHWLY-ZIIYPAMZSA-N
InChi Code
1S/C19H22O9/c1-7-3-10(22)14(19-17(26)16(25)15(24)12(6-20)28-19)18-13(7)11(23)5-9(27-18)4-8(2)21/h3,5,12,15-17,19-20,22,24-26H,4,6H2,1-2H3/t12-,15-,16+,17-,19+/m1/s1
SMILES Code
CC(=O)CC1=CC(=O)c2c(C)cc(O)c([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c2O1
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
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Aloesin (Aloeresin) displays anti-inflammatory activity, ultraviolet protection, and antibacterium effects. Aloesin exerts its anticancer effect through the MAPK signaling pathway.
In vitro activity:
MTT assay showed that aloesin exhibited a concentration-dependent and time-dependent killing of diverse ovarian cancer cell lines (Figures 1(a) and 1(b)). The SKOV3 cell line was more sensitive to aloesin than other cell lines. Aloesin had a significantly potent toxic effect with an IC50 value of around 5 μM in SKOV3 cell lines. Therefore, SKOV3 cell lines were chosen as the optimal cell models for subsequent functional analyses. SKOV3 cell line was treated with aloesin in dosages ranging from 2.5 to 10 μM in vitro. This study adopted the doses 0, 2.5, 5, and 10 μM of aloesin and performed colony formation assays. It was visually observed that colonies were smaller in size with increasing doses of aloesin (Figure 1(c)). Quantitative analysis further revealed that colony numbers also decreased with increasing doses of aloesin (Figure 1(d)). Consistently, the average area of a single clone was also decreasingly smaller as the aloesin dose increased (Figure 1(e)). These data suggest that aloesin inhibits ovarian cancer cells growth in a dose- and time-dependent manner. Reference: Anal Cell Pathol (Amst). 2017; 2017: 8158254. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5494088/
In vivo activity:
Hairless mice treated with vehicle showed a slower rate of wound closure and dermal regeneration than did mice treated with different concentrations of aloesin solution over a period of 10 days (Fig. 3A). There were significant differences in wound size between treatment groups from day 4 postinjury onwards (Fig. 3B). Wounds were almost completely closed by day 8 in aloesin-treated mice, whereas the wounds in mice treated with vehicle only were not completely healed until day 8. H&E staining of skin tissue samples at different time points after wound creation also showed faster and better neoepithelium and granulation tissue formation in aloesin-treated groups compared with vehicle-treated groups (Fig. 3C). Aloesin treatment resulted in generation of dermis and epidermis and reorganization as well as granulation tissue formation significantly faster than did vehicle treatment (Fig. 3D and E). Reference: Phytomedicine. 2017 May 15;28:19-26. https://pubmed.ncbi.nlm.nih.gov/28478809/
Solvent mg/mL mM comments
Solubility
DMSO 122.7 311.05
DMF 20.0 50.71
Ethanol 10.0 25.36
PBS (pH 7.2) 5.0 12.68
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 394.38 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. Zhang LQ, Lv RW, Qu XD, Chen XJ, Lu HS, Wang Y. Aloesin Suppresses Cell Growth and Metastasis in Ovarian Cancer SKOV3 Cells through the Inhibition of the MAPK Signaling Pathway. Anal Cell Pathol (Amst). 2017;2017:8158254. doi: 10.1155/2017/8158254. Epub 2017 Jun 18. PMID: 28702312; PMCID: PMC5494088. 2. Wahedi HM, Jeong M, Chae JK, Do SG, Yoon H, Kim SY. Aloesin from Aloe vera accelerates skin wound healing by modulating MAPK/Rho and Smad signaling pathways in vitro and in vivo. Phytomedicine. 2017 May 15;28:19-26. doi: 10.1016/j.phymed.2017.02.005. Epub 2017 Mar 4. PMID: 28478809.
In vitro protocol:
1. Zhang LQ, Lv RW, Qu XD, Chen XJ, Lu HS, Wang Y. Aloesin Suppresses Cell Growth and Metastasis in Ovarian Cancer SKOV3 Cells through the Inhibition of the MAPK Signaling Pathway. Anal Cell Pathol (Amst). 2017;2017:8158254. doi: 10.1155/2017/8158254. Epub 2017 Jun 18. PMID: 28702312; PMCID: PMC5494088. 2. Wahedi HM, Jeong M, Chae JK, Do SG, Yoon H, Kim SY. Aloesin from Aloe vera accelerates skin wound healing by modulating MAPK/Rho and Smad signaling pathways in vitro and in vivo. Phytomedicine. 2017 May 15;28:19-26. doi: 10.1016/j.phymed.2017.02.005. Epub 2017 Mar 4. PMID: 28478809.
In vivo protocol:
1. Zhang LQ, Lv RW, Qu XD, Chen XJ, Lu HS, Wang Y. Aloesin Suppresses Cell Growth and Metastasis in Ovarian Cancer SKOV3 Cells through the Inhibition of the MAPK Signaling Pathway. Anal Cell Pathol (Amst). 2017;2017:8158254. doi: 10.1155/2017/8158254. Epub 2017 Jun 18. PMID: 28702312; PMCID: PMC5494088. 2. Wahedi HM, Jeong M, Chae JK, Do SG, Yoon H, Kim SY. Aloesin from Aloe vera accelerates skin wound healing by modulating MAPK/Rho and Smad signaling pathways in vitro and in vivo. Phytomedicine. 2017 May 15;28:19-26. doi: 10.1016/j.phymed.2017.02.005. Epub 2017 Mar 4. PMID: 28478809.
1: Sánchez M, González-Burgos E, Iglesias I, Gómez-Serranillos MP. Pharmacological Update Properties of Aloe Vera and its Major Active Constituents. Molecules. 2020 Mar 13;25(6):1324. doi: 10.3390/molecules25061324. PMID: 32183224; PMCID: PMC7144722. 2: Yimam M, Brownell L, Jia Q. Aloesin as a medical food ingredient for systemic oxidative stress of diabetes. World J Diabetes. 2015 Aug 10;6(9):1097-107. doi: 10.4239/wjd.v6.i9.1097. PMID: 26265996; PMCID: PMC4530323. 3: Zaid AN, Al Ramahi R. Depigmentation and Anti-aging Treatment by Natural Molecules. Curr Pharm Des. 2019;25(20):2292-2312. doi: 10.2174/1381612825666190703153730. PMID: 31269882. 4: Zhang LQ, Lv RW, Qu XD, Chen XJ, Lu HS, Wang Y. Aloesin Suppresses Cell Growth and Metastasis in Ovarian Cancer SKOV3 Cells through the Inhibition of the MAPK Signaling Pathway. Anal Cell Pathol (Amst). 2017;2017:8158254. doi: 10.1155/2017/8158254. Epub 2017 Jun 18. PMID: 28702312; PMCID: PMC5494088. 5: Wahedi HM, Jeong M, Chae JK, Do SG, Yoon H, Kim SY. Aloesin from Aloe vera accelerates skin wound healing by modulating MAPK/Rho and Smad signaling pathways in vitro and in vivo. Phytomedicine. 2017 May 15;28:19-26. doi: 10.1016/j.phymed.2017.02.005. Epub 2017 Mar 4. PMID: 28478809. 6: Choi S, Lee SK, Kim JE, Chung MH, Park YI. Aloesin inhibits hyperpigmentation induced by UV radiation. Clin Exp Dermatol. 2002 Sep;27(6):513-5. doi: 10.1046/j.1365-2230.2002.01120.x. PMID: 12372097. 7: Lynch B, Simon R, Roberts A. In vitro and in vivo assessment of the genotoxic activity of aloesin. Regul Toxicol Pharmacol. 2011 Nov;61(2):215-21. doi: 10.1016/j.yrtph.2011.07.011. Epub 2011 Jul 29. PMID: 21821088. 8: Kong XY, Chen TT, Zhang HW, Jia HM, Yu M, Zou ZM. Characterization of the metabolism of aloin A/B and aloesin in rats using ultra-high performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry. Biomed Chromatogr. 2022 Dec;36(12):e5483. doi: 10.1002/bmc.5483. Epub 2022 Sep 9. PMID: 35975594. 9: Yagi A, Takeo S. [Anti-inflammatory constituents, aloesin and aloemannan in Aloe species and effects of tanshinon VI in Salvia miltiorrhiza on heart]. Yakugaku Zasshi. 2003 Jul;123(7):517-32. Japanese. doi: 10.1248/yakushi.123.517. PMID: 12875235. 10: Añibarro-Ortega M, Pinela J, Ćirić A, Lopes E, Molina AK, Calhelha RC, Soković M, Ferreira O, Ferreira ICFR, Barros L. Extraction of Aloesin from Aloe vera Rind Using Alternative Green Solvents: Process Optimization and Biological Activity Assessment. Biology (Basel). 2021 Sep 23;10(10):951. doi: 10.3390/biology10100951. PMID: 34681050; PMCID: PMC8533118. 11: Steenkamp L, Mathiba K, Steenkamp P, Phehane V, Mitra R, Heggie S, Brady D. Biocatalytic conversion of aloeresin A to aloesin. J Ind Microbiol Biotechnol. 2012 Jul;39(7):1091-7. doi: 10.1007/s10295-012-1101-5. Epub 2012 Feb 29. PMID: 22374229. 12: Jones K, Hughes J, Hong M, Jia Q, Orndorff S. Modulation of melanogenesis by aloesin: a competitive inhibitor of tyrosinase. Pigment Cell Res. 2002 Oct;15(5):335-40. doi: 10.1034/j.1600-0749.2002.02014.x. PMID: 12213089. 13: Lee KY, Park JH, Chung MH, Park YI, Kim KW, Lee YJ, Lee SK. Aloesin up- regulates cyclin E/CDK2 kinase activity via inducing the protein levels of cyclin E, CDK2, and CDC25A in SK-HEP-1 cells. Biochem Mol Biol Int. 1997 Feb;41(2):285-92. doi: 10.1080/15216549700201291. PMID: 9063568. 14: Jin YH, Lee SJ, Chung MH, Park JH, Park YI, Cho TH, Lee SK. Aloesin and arbutin inhibit tyrosinase activity in a synergistic manner via a different action mechanism. Arch Pharm Res. 1999 Jun;22(3):232-6. doi: 10.1007/BF02976355. PMID: 10403123. 15: Lynch B, Simon R, Roberts A. Subchronic toxicity evaluation of aloesin. Regul Toxicol Pharmacol. 2011 Nov;61(2):161-71. doi: 10.1016/j.yrtph.2011.07.005. Epub 2011 Jul 19. PMID: 21784118. 16: Dell'Agli M, Giavarini F, Ferraboschi P, Galli G, Bosisio E. Determination of aloesin and aloeresin A for the detection of aloe in beverages. J Agric Food Chem. 2007 May 2;55(9):3363-7. doi: 10.1021/jf070182h. Epub 2007 Apr 10. PMID: 17419646. 17: Hollinger JC, Angra K, Halder RM. Are Natural Ingredients Effective in the Management of Hyperpigmentation? A Systematic Review. J Clin Aesthet Dermatol. 2018 Feb;11(2):28-37. Epub 2018 Feb 1. PMID: 29552273; PMCID: PMC5843359. 18: Wang Z, Li X, Yang Z, He X, Tu J, Zhang T. Effects of aloesin on melanogenesis in pigmented skin equivalents. Int J Cosmet Sci. 2008 Apr;30(2):121-30. doi: 10.1111/j.1468-2494.2008.00432.x. PMID: 18377621. 19: Mikayoulou M, Mayr F, Temml V, Pandian A, Vermaak I, Chen W, Komane B, Stuppner H, Viljoen A. Anti-tyrosinase activity of South African Aloe species and isolated compounds plicataloside and aloesin. Fitoterapia. 2021 Apr;150:104828. doi: 10.1016/j.fitote.2021.104828. Epub 2021 Jan 9. PMID: 33434632. 20: Yang ZQ, Wang ZH, Tu JB, Li P, Hu XY. [The effects of aloesin and arbutin on cultured melanocytes in a synergetic method]. Zhonghua Zheng Xing Wai Ke Za Zhi. 2004 Sep;20(5):369-71. Chinese. PMID: 15623110.