Helen Frankenthaler Foundation

Ecdysterone and Analogs

Ecdysterone | 20-Hydroxyecdysone | CAS#5289-74-7 | Caspase Inhibitor

Description

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

20-Hydroxyecdysone (ecdysterone or 20E) is a naturally occurring ecdysteroid hormone which controls the ecdysis (moulting) and metamorphosis of arthropods. It is therefore one of the most common moulting hormones in insects, crabs, etc. It is also a phytoecdysteroid produced by various plants, including Cyanotis vaga, where its purpose is presumably to disrupt the development and reproduction of insect pests. In arthropods, 20-hydroxyecdysone acts through the ecdysone receptor. Although mammals lack this receptor, 20-hydroxyecdysone may affect mammalian (including human) biological systems in vitro, but there is uncertainty whether any in vivo or physiological effects occur. 20-Hydroxyecdysone is an ingredient of some supplements that aim to enhance physical performance, but there is no clinical evidence for this effect. (Source: https://www.frankenthalerfoundation.org

Related CAS #

No Data

Synonym

20Hydroxyecdysone; 20-Hydroxyecdysone; 20 Hydroxyecdysone; 20E; Ecdysterone; Isoinokosterone; Crustecdysone; beta-Ecdysone; NSC629484; NSC 629484; NSC-629484

IUPAC/Chemical Name

(2b,3b,5b,22R)-2,3,14,20,22,25-Hexahydroxycholest-7-en-6-one

InChi Key

NKDFYOWSKOHCCO-YPVLXUMRSA-N

InChi Code

InChI=1S/C27H44O7/c1-23(2,32)9-8-22(31)26(5,33)21-7-11-27(34)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h12,15,17,19-22,29-34H,6-11,13-14H2,1-5H3/t15-,17-,19+,20-,21-,22+,24+,25+,26+,27+/m0/s1

SMILES Code

CC(C)(O)CC[C@@H](O)[C@](C)(O)[C@H]1CC[C@@]2(O)C3=CC([C@]4([H])C[C@@H](O)[C@@H](O)C[C@]4(C)[C@@]3([H])CC[C@]12C)=O

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
Instruction
Biological target:

Ecdysterone inhibits caspase activity and induces autophagy via the 20E nuclear receptor complex, EcR-USP.

In vitro activity:

Results shown in Figures 1A–C clearly demonstrate that in othis study’s case the treatment with Ecdy has down-regulated all three cell lines starting with a concentration of 250–750 µM. No increase in cell proliferation was detected. Reference: Front Pharmacol. 2020; 11: 561537. https://www.frankenthalerfoundation.org

In vivo activity:

As shown in Figure 6A, significant cartilage degeneration, with proteoglycan depletion, loss of surface lamina and fibrillations were observed on OA model rats and OA rats treated with 3-methyladenine. These OA-like symptoms were greatly improved in OA rats treated with rapamycin and β-ecdysterone, especially with 100 nM rapamycin and 40 μM β-ecdysterone. As shown in Figure 6B, the concentration of IL-1β, IL-6, NO and TNF-α were found to be significantly decreased in rapamycin and β-ecdysterone treated rats, compared with control. On the contrary, IL-1β, IL-6, NO and TNF-α were excessively secreted in the cartilage tissue in OA rats treated with 3-methyladenine (*P < 0.05, vs. Control, **P < 0.01, vs. Control). These data indicated that the pathological and inflammatory states of OA rats were remarkably improved by β-ecdysterone in a dose dependent manner. Reference: Am J Transl Res. 2020; 12(11): 7174–7186. https://www.frankenthalerfoundation.org

Solventmg/mLmMcomments
Solubility
DMSO75.3156.73
DMF30.062.42
Ethanol60.5125.88
PBS (pH 7.2)10.020.81

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 480.63 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 / Mass1 mg5 mg10 mg
1 mM1.15 mL5.76 mL11.51 mL
5 mM0.23 mL1.15 mL2.3 mL
10 mM0.12 mL0.58 mL1.15 mL
50 mM0.02 mL0.12 mL0.23 mL
Formulation protocol:

1. Shuvalov O, Fedorova O, Tananykina E, Gnennaya Y, Daks A, Petukhov A, Barlev NA. An Arthropod Hormone, Ecdysterone, Inhibits the Growth of Breast Cancer Cells via Different Mechanisms. Front Pharmacol. 2020 Oct 30;11:561537. doi: 10.3389/fphar.2020.561537. PMID: 33192507; PMCID: PMC7663021. 2. Wen F, Yu J, He CJ, Zhang ZW, Yang AF. β‑ecdysterone protects against apoptosis by promoting autophagy in nucleus pulposus cells and ameliorates disc degeneration. Mol Med Rep. 2019 Mar;19(3):2440-2448. doi: 10.3892/mmr.2019.9861. Epub 2019 Jan 15. PMID: 30664184. 3. Yang L, Friedemann T, Pan J. Ecdysterone Attenuates the Development of Radiation-Induced Oral Mucositis in Rats at Early Stage. Radiat Res. 2021 Jul 8. doi: 10.1667/RADE-21-00042.1. Epub ahead of print. PMID: 34237140. 4. Tang Y, Mo Y, Xin D, Zeng L, Yue Z, Xu C. β-ecdysterone alleviates osteoarthritis by activating autophagy in chondrocytes through regulating PI3K/AKT/mTOR signal pathway. Am J Transl Res. 2020 Nov 15;12(11):7174-7186. PMID: 33312358; PMCID: PMC7724317.

In vitro protocol:

1. Shuvalov O, Fedorova O, Tananykina E, Gnennaya Y, Daks A, Petukhov A, Barlev NA. An Arthropod Hormone, Ecdysterone, Inhibits the Growth of Breast Cancer Cells via Different Mechanisms. Front Pharmacol. 2020 Oct 30;11:561537. doi: 10.3389/fphar.2020.561537. PMID: 33192507; PMCID: PMC7663021. 2. Wen F, Yu J, He CJ, Zhang ZW, Yang AF. β‑ecdysterone protects against apoptosis by promoting autophagy in nucleus pulposus cells and ameliorates disc degeneration. Mol Med Rep. 2019 Mar;19(3):2440-2448. doi: 10.3892/mmr.2019.9861. Epub 2019 Jan 15. PMID: 30664184.

In vivo protocol:

1. Yang L, Friedemann T, Pan J. Ecdysterone Attenuates the Development of Radiation-Induced Oral Mucositis in Rats at Early Stage. Radiat Res. 2021 Jul 8. doi: 10.1667/RADE-21-00042.1. Epub ahead of print. PMID: 34237140. 2. Tang Y, Mo Y, Xin D, Zeng L, Yue Z, Xu C. β-ecdysterone alleviates osteoarthritis by activating autophagy in chondrocytes through regulating PI3K/AKT/mTOR signal pathway. Am J Transl Res. 2020 Nov 15;12(11):7174-7186. PMID: 33312358; PMCID: PMC7724317.

1: Cahlíková L, Macáková K, Chlebek J, Host'álková A, Kulhánková A, Opletal L. Ecdysterone and its activity on some degenerative diseases. Nat Prod Commun. 2011 May;6(5):707-18. Review. PubMed PMID: 21615037.