Asiaticoside | CAS#16830-15-2 | MITF inhibition | apoptosis inducer

MedKoo Cat#: 540035 | Name: Asiaticoside

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Description:

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

Asiaticoside is a skin whiening agent found in Cetella. It decreases DNA binding by MITF. It also induces apoptosis in breast cancer cells, improves memory and learning deficits, decreases release of pro-inflammatory cytokines, and suppresses LPS-induced inflammation and fever.

Chemical Structure

Asiaticoside

CAS#16830-15-2

Theoretical Analysis

MedKoo Cat#: 540035

Name: Asiaticoside

CAS#: 16830-15-2

Chemical Formula: C48H78O19

Exact Mass: 958.5137

Molecular Weight: 959.13

Elemental Analysis: C, 60.11; H, 8.20; O, 31.69

Price and Availability

Size	Price	Availability
10mg	USD 250.00	2 Weeks
50mg	USD 650.00	2 Weeks
100mg	USD 950.00	2 Weeks

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Synonym

Asiaticoside; Ba 2742; BRN0078195; CCRIS8995; NSC166062; BRN-0078195; CCRIS-8995; NSC-166062; BRN 0078195; CCRIS 8995; NSC 166062; Emdecassol; Madecassol;

IUPAC/Chemical Name

(2S,3R,4S,5S,6R)-6-((((2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)methyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl (1S,2R,4aS,6aS,6bR,8aR,9R,10R,11R,12aR,12bR,14bS)-10,11-dihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate

InChi Key

WYQVAPGDARQUBT-FGWHUCSPSA-N

InChi Code

InChI=1S/C48H78O19/c1-20-10-13-48(15-14-46(6)23(29(48)21(20)2)8-9-28-44(4)16-24(51)39(60)45(5,19-50)27(44)11-12-47(28,46)7)43(61)67-42-36(58)33(55)31(53)26(65-42)18-62-40-37(59)34(56)38(25(17-49)64-40)66-41-35(57)32(54)30(52)22(3)63-41/h8,20-22,24-42,49-60H,9-19H2,1-7H3/t20-,21+,22+,24-,25-,26-,27-,28-,29+,30+,31-,32-,33+,34-,35-,36-,37-,38-,39+,40-,41+,42+,44+,45+,46-,47-,48+/m1/s1

SMILES Code

C[C@@H]1CC[C@]2(C(O[C@@H]3O[C@@H]([C@H]([C@@H]([C@H]3O)O)O)CO[C@@H]4O[C@@H]([C@H]([C@@H]([C@H]4O)O)O[C@@H]5O[C@H]([C@@H]([C@H]([C@H]5O)O)O)C)CO)=O)CC[C@@]6(C([C@@H]2[C@H]1C)=CC[C@@H]7[C@]8(C[C@H]([C@@H]([C@@](CO)([C@@H]8CC[C@@]67C)C)O)O)C)C

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

>2 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:

Asiaticoside suppresses TGF-β/Smad signaling through inducing Smad7 and inhibiting TGF-βRI and TGF-βRII in keloid fibroblasts.

In vitro activity:

As shown in Figure 2A, AC (Asiaticoside) reduced proliferation and diminished the viability of fibroblasts when the concentration of AC was more than 400 μg/mL, whereas lower than 200 μg/ mL did not affect cell viability of fibroblasts. However, pretreatment of fibroblasts with 200 μg/mL AC before radiation significantly promoted survival rates compared to fibroblasts treated with radiation alone at 6 Gy doses (Figure 2B). Similarly, AC enhanced H2O2 treatment-mediated decline in fibroblast cell viability (Figure 2C). These data suggest that AC attenuates cell apoptosis in irradiated fibroblasts. Reference: Open Life Sci. 2020; 15: 145–151. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8114779/

In vivo activity:

The results of tumor formation in nude mice (Figure 5A,B) showed that when the ATS (Asiaticoside) concentration was 5 mg/kg and 10 mg/kg, the tumor’s weight and volume decreased significantly (P<0.05). The TUNEL results (Figure 5C,D) showed that when the ATS concentration was 5 mg/kg, the cell apoptosis rate of the tumor tissue increased significantly (P<0.05). The results of immunohistochemistry (Figure 5C,E,F) showed that the positive expression rates of vimentin and SOX2 proteins in tumor tissues significantly decreased (P<0.05). Reference: J Gastrointest Oncol. 2021 Feb; 12(1): 196–206. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7944148/

	Solvent	mg/mL	mM
Solubility
	DMSO	53.3	55.60
	DMF	25.0	26.07
	Ethanol	5.0	5.21
	PBS (pH 7.2)	10.0	10.43

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 959.13 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.

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 M, Liu S, Fang L, Wang G, Yin L. Asiaticoside inhibits renal fibrosis development by regulating the miR-142-5p/ACTN4 axis. Biotechnol Appl Biochem. 2021 Jan 14. doi: 10.1002/bab.2110. Epub ahead of print. PMID: 33444480. 2. Shen H, Zhu F, Li J, Tang S, Zhang Y, Zhang J. Protective Effect of Asiaticoside on Radiation-induced Proliferation Inhibition and DNA Damage of Fibroblasts and Mice Death. Open Life Sci. 2020 Apr 6;15:145-151. doi: 10.1515/biol-2020-0015. PMID: 33987471; PMCID: PMC8114779. 3. Guo M, Xu J, Wang S, Dong B. Asiaticoside reduces autophagy and improves memory in a rat model of dementia through mTOR signaling pathway regulation. Mol Med Rep. 2021 Sep;24(3):645. doi: 10.3892/mmr.2021.12284. Epub 2021 Jul 19. PMID: 34278477. 4. He Y, Peng X, Zheng L, Tang Y, Li J, Huang X. Asiaticoside inhibits epithelial-mesenchymal transition and stem cell-like properties of pancreatic cancer PANC-1 cells by blocking the activation of p65 and p38MAPK. J Gastrointest Oncol. 2021 Feb;12(1):196-206. doi: 10.21037/jgo-20-533. PMID: 33708436; PMCID: PMC7944148.

In vitro protocol:

In vivo protocol:

1. Guo M, Xu J, Wang S, Dong B. Asiaticoside reduces autophagy and improves memory in a rat model of dementia through mTOR signaling pathway regulation. Mol Med Rep. 2021 Sep;24(3):645. doi: 10.3892/mmr.2021.12284. Epub 2021 Jul 19. PMID: 34278477. 2. He Y, Peng X, Zheng L, Tang Y, Li J, Huang X. Asiaticoside inhibits epithelial-mesenchymal transition and stem cell-like properties of pancreatic cancer PANC-1 cells by blocking the activation of p65 and p38MAPK. J Gastrointest Oncol. 2021 Feb;12(1):196-206. doi: 10.21037/jgo-20-533. PMID: 33708436; PMCID: PMC7944148.

1: Fong LY, Ng CT, Zakaria ZA, Baharuldin MT, Arifah AK, Hakim MN, Zuraini A. Asiaticoside Inhibits TNF-α-Induced Endothelial Hyperpermeability of Human Aortic Endothelial Cells. Phytother Res. 2015 Oct;29(10):1501-8. doi: 10.1002/ptr.5404. Epub 2015 Jul 14. PubMed PMID: 26171791. 2: Sun T, Liu B, Li P. Nerve Protective Effect of Asiaticoside against Ischemia-Hypoxia in Cultured Rat Cortex Neurons. Med Sci Monit. 2015 Oct 8;21:3036-41. doi: 10.12659/MSM.894024. PubMed PMID: 26447863; PubMed Central PMCID: PMC4603616. 3: Luo Y, Fu C, Wang Z, Zhang Z, Wang H, Liu Y. Asiaticoside attenuates the effects of spinal cord injury through antioxidant and anti inflammatory effects, and inhibition of the p38 MAPK mechanism. Mol Med Rep. 2015 Dec;12(6):8294-300. doi: 10.3892/mmr.2015.4425. Epub 2015 Oct 9. PubMed PMID: 26458544. 4: Qi FY, Yang L, Tian Z, Zhao MG, Liu SB, An JZ. Neuroprotective effects of Asiaticoside. Neural Regen Res. 2014 Jul 1;9(13):1275-82. doi: 10.4103/1673-5374.137574. PubMed PMID: 25221579; PubMed Central PMCID: PMC4160853. 5: Hossain S, Hashimoto M, Katakura M, Al Mamun A, Shido O. Medicinal value of asiaticoside for Alzheimer's disease as assessed using single-molecule-detection fluorescence correlation spectroscopy, laser-scanning microscopy, transmission electron microscopy, and in silico docking. BMC Complement Altern Med. 2015 Apr 14;15:118. doi: 10.1186/s12906-015-0620-9. PubMed PMID: 25880304; PubMed Central PMCID: PMC4422550. 6: Al-Saeedi FJ. Study of the cytotoxicity of asiaticoside on rats and tumour cells. BMC Cancer. 2014 Mar 25;14:220. doi: 10.1186/1471-2407-14-220. PubMed PMID: 24667059; PubMed Central PMCID: PMC3986932. 7: Phaechamud T, Yodkhum K, Charoenteeraboon J, Tabata Y. Chitosan-aluminum monostearate composite sponge dressing containing asiaticoside for wound healing and angiogenesis promotion in chronic wound. Mater Sci Eng C Mater Biol Appl. 2015 May;50:210-25. doi: 10.1016/j.msec.2015.02.003. Epub 2015 Feb 9. PubMed PMID: 25746264. 8: Wang XB, Wang W, Zhu XC, Ye WJ, Cai H, Wu PL, Huang XY, Wang LX. The potential of asiaticoside for TGF-β1/Smad signaling inhibition in prevention and progression of hypoxia-induced pulmonary hypertension. Life Sci. 2015 Sep 15;137:56-64. doi: 10.1016/j.lfs.2015.07.016. Epub 2015 Jul 22. PubMed PMID: 26209140. 9: Luo L, Liu XL, Mu RH, Wu YJ, Liu BB, Geng D, Liu Q, Yi LT. Hippocampal BDNF signaling restored with chronic asiaticoside treatment in depression-like mice. Brain Res Bull. 2015 May;114:62-9. doi: 10.1016/j.brainresbull.2015.03.006. Epub 2015 Apr 7. PubMed PMID: 25857945. 10: Joy J, Alarifi S, Alsuhaibani E, Nair CK. Protection of DNA From Ionizing Radiation-Induced Lesions by Asiaticoside. J Environ Pathol Toxicol Oncol. 2015;34(4):353-61. PubMed PMID: 26756427. 11: Yin Z, Yu H, Chen S, Ma C, Ma X, Xu L, Ma Z, Qu R, Ma S. Asiaticoside attenuates diabetes-induced cognition deficits by regulating PI3K/Akt/NF-κB pathway. Behav Brain Res. 2015 Oct 1;292:288-99. doi: 10.1016/j.bbr.2015.06.024. Epub 2015 Jun 18. PubMed PMID: 26097002. 12: Nowwarote N, Osathanon T, Jitjaturunt P, Manopattanasoontorn S, Pavasant P. Asiaticoside induces type I collagen synthesis and osteogenic differentiation in human periodontal ligament cells. Phytother Res. 2013 Mar;27(3):457-62. doi: 10.1002/ptr.4742. Epub 2012 May 25. PubMed PMID: 22628285. 13: Zhang CZ, Niu J, Chong YS, Huang YF, Chu Y, Xie SY, Jiang ZH, Peng LH. Porous microspheres as promising vehicles for the topical delivery of poorly soluble asiaticoside accelerate wound healing and inhibit scar formation in vitro &in vivo. Eur J Pharm Biopharm. 2016 Dec;109:1-13. doi: 10.1016/j.ejpb.2016.09.005. Epub 2016 Sep 8. PubMed PMID: 27614186. 14: Wang Z, Liu J, Sun W. Effects of asiaticoside on levels of podocyte cytoskeletal proteins and renal slit diaphragm proteins in adriamycin-induced rat nephropathy. Life Sci. 2013 Sep 3;93(8):352-8. doi: 10.1016/j.lfs.2013.07.010. Epub 2013 Jul 18. PubMed PMID: 23871990. 15: Kwon KJ, Bae S, Kim K, An IS, Ahn KJ, An S, Cha HJ. Asiaticoside, a component of Centella asiatica, inhibits melanogenesis in B16F10 mouse melanoma. Mol Med Rep. 2014 Jul;10(1):503-7. doi: 10.3892/mmr.2014.2159. Epub 2014 Apr 16. PubMed PMID: 24756377. 16: Hou SQ, Fang M, Chen SS, Cong XP, Zhang DD, Li XM. [Biochemical regulatory mechanism of asiaticoside in preventing and treating stent restenosis]. Zhongguo Zhong Yao Za Zhi. 2014 Apr;39(8):1479-84. Chinese. PubMed PMID: 25039186. 17: Loc NH, Nhat NT. Production of asiaticoside from centella (Centella asiatica L. Urban) cells in bioreactor. Asian Pac J Trop Biomed. 2013 Oct;3(10):806-10. doi: 10.1016/S2221-1691(13)60159-8. Epub 2013 Sep 4. PubMed PMID: 24075346; PubMed Central PMCID: PMC3761140. 18: Qiu J, Yu L, Zhang X, Wu Q, Wang D, Wang X, Xia C, Feng H. Asiaticoside attenuates lipopolysaccharide-induced acute lung injury via down-regulation of NF-κB signaling pathway. Int Immunopharmacol. 2015 May;26(1):181-7. doi: 10.1016/j.intimp.2015.03.022. Epub 2015 Mar 30. PubMed PMID: 25835778. 19: Ozdemir O, Ozkan K, Hatipoglu F, Uyaroglu A, Arican M. Effect of Asiaticoside, Collagenase, and Alpha-chymotrypsin on Wound Healing in Rabbits. Wounds. 2016 Aug;28(8):279-86. PubMed PMID: 27560471. 20: Guo T, Fang M, Zhang D, Li X. Combination treatment with asiaticoside and rapamycin: A new hope for in-stent restenosis. Exp Ther Med. 2013 Aug;6(2):557-561. Epub 2013 Jun 13. PubMed PMID: 24137226; PubMed Central PMCID: PMC3786836.

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