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MedKoo Cat#: 464953 | Name: Turkesterone hydrate
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Description:

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

Turkesterone is a phytoecdysteroid that has been found in A. turkestanica and has diverse biological activities. It binds to the ecdysteroid receptor (KD = 0.491 µM for the C. tentans receptor) and induces pupariation in G. mellonella, S. bullata, and D. vulpinus last instar larvae (ED50s = 10, 0.03, and 0.2 µg/larvae, respectively). Turkesterone scavenges DPPH radicals in a cell-free assay (IC50 = 140.92 µg/ml) and is cytotoxic to HeLa cervical, HepG2 hepatic, and MCF-7 breast cancer cells (IC50s = 75.2, 63.01, and 105.2 µg/ml, respectively). It decreases serum glucose levels and increases serum insulin and C-peptide levels in a rat model of diabetes induced by alloxan when administered at a dose of 10 mg/kg. Turkesterone prevents immobilization stress-induced stomach ulcers in mice.

Chemical Structure

Turkesterone hydrate
Turkesterone hydrate
CAS#unknown

Theoretical Analysis

MedKoo Cat#: 464953

Name: Turkesterone hydrate

CAS#: unknown

Chemical Formula: C27H46O9

Exact Mass: 514.3142

Molecular Weight: 514.66

Elemental Analysis: C, 63.01; H, 9.01; O, 27.98

Price and Availability

Size Price Availability Quantity
1mg USD 450.00 2 Weeks
5mg USD 750.00 2 Weeks
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Related CAS #
41451-87-0 (free base)
Synonym
Turkesterone hydrate;
IUPAC/Chemical Name
(2S,3R,5R,9R,10R,11R,13R,14S,17S)-2,3,11,14-tetrahydroxy-10,13-dimethyl-17-((2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl)-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-6H-cyclopenta[a]phenanthren-6-one hydrate
InChi Key
KPDDBZPCPQHPNZ-ZSNHUFKWSA-N
InChi Code
InChI=1S/C27H44O8.H2O/c1-23(2,33)8-7-21(32)26(5,34)20-6-9-27(35)15-11-16(28)14-10-17(29)18(30)12-24(14,3)22(15)19(31)13-25(20,27)4;/h11,14,17-22,29-35H,6-10,12-13H2,1-5H3;1H2/t14-,17+,18-,19+,20-,21+,22+,24-,25+,26+,27+;/m0./s1
SMILES Code
O[C@]12C([C@@]([H])([C@]3(C)[C@@](C[C@@H](O)[C@@H](O)C3)4[H])[C@H](O)C[C@]1(C)[C@]([H])(CC2)[C@@](O)([C@@H](CCC(O)(C)C)O)C)=CC4=O.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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 514.66 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
1: Janeczko A, Oklestkova J, Tarkowská D, Drygaś B. Naturally Occurring Ecdysteroids in Triticum aestivum L. and Evaluation of Fenarimol as a Potential Inhibitor of Their Biosynthesis in Plants. Int J Mol Sci. 2021 Mar 11;22(6):2855. doi: 10.3390/ijms22062855. PMID: 33799719; PMCID: PMC7999220. 2: Zughdani M, Yusufoğlu HS, Ekiz G, Linden A, Çalış İ. Ecdysteroids from the underground parts of Rhaponticum acaule (L.) DC. Phytochemistry. 2020 Dec;180:112530. doi: 10.1016/j.phytochem.2020.112530. Epub 2020 Oct 10. PMID: 33049649. 3: Guibout L, Mamadalieva N, Balducci C, Girault JP, Lafont R. The minor ecdysteroids from Ajuga turkestanica. Phytochem Anal. 2015 Sep- Oct;26(5):293-300. doi: 10.1002/pca.2563. Epub 2015 May 8. PMID: 25953625. 4: Syrov VN, Islamova ZhI, Égamova FR, Iuldasheva NKh, Khushbaktova ZA. [Stress- protective properties of phytoecdysteroids]. Eksp Klin Farmakol. 2014;77(7):35-8. Russian. PMID: 25322653. 5: Eresen Yazıcıoğlu C, Karatosun V, Kızıldağ S, Ozsoylu D, Kavukçu S. ACVR1 gene mutations in four Turkish patients diagnosed as fibrodysplasia ossificans progressiva. Gene. 2013 Feb 25;515(2):444-6. doi: 10.1016/j.gene.2012.12.005. Epub 2012 Dec 20. PMID: 23260810. 6: Syrov VN, Iuldasheva NKh, Égamova FR, Ismailova GI, Abdullaev ND, Khushbaktova ZA. [Estimation of the hypoglycemic effect of phytoecdysteroids]. Eksp Klin Farmakol. 2012;75(5):28-31. Russian. PMID: 22834126. 7: Aytaç S, Dursun S. The effect on employees of violence climate in the workplace. Work. 2012;41 Suppl 1:3026-31. doi: 10.3233/WOR-2012-0559-3026. PMID: 22317180. 8: Budesínský M, Vokác K, Harmatha J, Cvacka J. Additional minor ecdysteroid components of Leuzea carthamoides. Steroids. 2008 May;73(5):502-14. doi: 10.1016/j.steroids.2007.12.021. Epub 2007 Dec 28. Erratum in: Steroids. 2009 Nov;74(12):1003-4. PMID: 18243263. 9: Dinan L, Bourne P, Whiting P, Tsitsekli A, Saatov Z, Dhadialla TS, Hormann RE, Lafont R, Coll J. Synthesis and biological activities of turkesterone 11alpha-acyl derivatives. J Insect Sci. 2003;3:6. doi: 10.1093/jis/3.1.6. Epub 2003 Feb 24. PMID: 15841223; PMCID: PMC524646. 10: Bourne PC, Whiting P, Dhadialla TS, Hormann RE, Girault JP, Harmatha J, Lafont R, Dinan L. Ecdysteroid 7,9(11)-dien-6-ones as potential photoaffinity labels for ecdysteroid binding proteins. J Insect Sci. 2002;2:11. doi: 10.1093/jis/2.1.11. PMID: 15455045; PMCID: PMC355911. 11: Suksamrarn A, Kumpun S, Yingyongnarongkul BE. Ecdysteroids of Vitex scabra stem bark. J Nat Prod. 2002 Nov;65(11):1690-2. doi: 10.1021/np020199o. PMID: 12444704. 12: Syrov VN, Khushbaktova ZA. Farmakoterapevticheskiĭ éffekt fitoékdisteroidov i nerobola pri toksicheskom porazhenii pochek v éksperimente [Experimental study of pharmacotherapeutic effect of phytoecdisteroids and nerobol in toxic liver damage]. Eksp Klin Farmakol. 2001 Jul-Aug;64(4):56-8. Russian. PMID: 11589113. 13: dos Santos TC, Delle Monache F, Leitão SG. Ecdysteroids from two Brazilian Vitex species. Fitoterapia. 2001 Mar;72(3):215-20. doi: 10.1016/s0367-326x(00)00304-x. PMID: 11295296. 14: Najmutdinova DK, Saatov Z. Lung local defense in experimental diabetes mellitus and the effect of 11,20-dihydroxyecdysone in combination with maninil. Arch Insect Biochem Physiol. 1999;41(3):144-7. doi: 10.1002/(SICI)1520-6327(1999)41:3<144::AID-ARCH5>3.0.CO;2-0. PMID: 10398337. 15: Syrov VN, Nasyrova SS, Khushbaktova ZA. Rezul'taty eksperimental'nogo izucheniia fitoékdisteroidov v kachestve stimuliatorov eritropoéza u laboratornykh zhivotnykh [The results of experimental study of phytoecdysteroids as erythropoiesis stimulators in laboratory animals]. Eksp Klin Farmakol. 1997 May-Jun;60(3):41-4. Russian. PMID: 9324397. 16: Syrov VN, Tashmukhamedova MA, Khushbaktova ZA, Mirtalipov DT, Mamatkhanov AU. Vliianie fitoékdisteroidov i nerobola na pokazateli uglevodnogo i lipidnogo obmenov i fosfolipidnyĭ spektr membran mitokhondriĭ pecheni krys pri éksperimental'nom sakharnom diabete [Effect of phytoecdysteroids and nerobol on parameters of carbohydrate and lipid metabolism and phospholipid spectrum of liver mitochondrial membrane in experimental diabetes mellitus of rats]. Ukr Biokhim Zh (1978). 1992 Jul-Aug;64(4):61-7. Russian. PMID: 1448876. 17: Syrov VN, Khushbaktova ZA, Nabiev AN. Eksperimental'noe izuchenie gepatoprotektornykh svoĭstv fitoékdisteroidov i nerobola pri porazhenii pecheni chetyrekhkhloristym uglerodom [An experimental study of the hepatoprotective properties of phytoecdysteroids and nerobol in carbon tetrachloride-induced liver lesion]. Eksp Klin Farmakol. 1992 May-Jun;55(3):61-5. Russian. PMID: 1458171. 18: Guo DA, Lou ZC, Gao CY, Qiao L, Peng JR. [Phytoecdysteroids of Rhaponticum uniflorum root]. Yao Xue Xue Bao. 1991;26(6):442-6. Chinese. PMID: 1789111. 19: Kubo I, Asaka Y, Stout MJ, Nakatsu T. Structure of a novel phytoecdysteroid, vitexirone, and efficient isolation of phytoecdysteroids fromVitex fisherii. J Chem Ecol. 1990 Aug;16(8):2581-8. doi: 10.1007/BF01017480. PMID: 24264222. 20: Tashmukhamedova MA, Almatov KT, Syrov VN, Sultanov MB, Abidov AA. Sravnitel'noe izuchenie deĭstviia ékdisterona, turkesterona i nerobola na funktsii mitokhondriĭ pecheni krys pri éksperimental'nom diabete [Comparative study of the effect of ecdysterone, turkesterone and nerobol on the function of rat liver mitochondria in experimental diabetes]. Vopr Med Khim. 1986 Sep- Oct;32(5):24-8. Russian. PMID: 3776112.