Destruxin E | CAS#76689-14-0 | Cyclodepsipeptide mycotoxin

MedKoo Cat#: 463276 | Name: Destruxin E

Description:

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

Destruxin E is a cyclodepsipeptide mycotoxin from entomopathogenic fungus Metarhyzium anisopliae.

Chemical Structure

Destruxin E

CAS#76689-14-0

Theoretical Analysis

MedKoo Cat#: 463276

Name: Destruxin E

CAS#: 76689-14-0

Chemical Formula: C29H47N5O8

Exact Mass: 593.3425

Molecular Weight: 593.72

Elemental Analysis: C, 58.67; H, 7.98; N, 11.80; O, 21.56

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

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Synonym

Destruxin E; Destruxin-E; Destruxin DE; Destruxin-DE; E-Destruxin; E Destruxin;

IUPAC/Chemical Name

(3S,6S,9S,16R,21aS)-3-((S)-sec-butyl)-6-isopropyl-5,8,9-trimethyl-16-(((S)-oxiran-2-yl)methyl)dodecahydropyrrolo[1,2-d][1]oxa[4,7,10,13,16]pentaazacyclononadecine-1,4,7,10,14,17(11H,16H)-hexaone

InChi Key

NIAYGGCQOYIHAF-OHOJESAGSA-N

InChi Code

InChI=1S/C29H47N5O8/c1-8-17(4)23-28(39)33(7)24(16(2)3)29(40)32(6)18(5)25(36)30-12-11-22(35)42-21(14-19-15-41-19)27(38)34-13-9-10-20(34)26(37)31-23/h16-21,23-24H,8-15H2,1-7H3,(H,30,36)(H,31,37)/t17-,18-,19-,20-,21+,23-,24-/m0/s1

SMILES Code

CC[C@@H]([C@@H]1NC([C@@H]2CCCN2C([C@H](OC(CCNC([C@@H](N(C([C@@H](N(C1=O)C)C(C)C)=O)C)C)=O)=O)C[C@H]3CO3)=O)=O)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

>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

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 593.72 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

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Chem Pharm Bull (Tokyo). 2016;64(7):988-90. doi: 10.1248/cpb.c16-00220. PMID: 27373660. 4: Yoshida M, Ishida Y, Adachi K, Murase H, Nakagawa H, Doi T. Solid-Phase Combinatorial Synthesis and Biological Evaluation of Destruxin E Analogues. Chemistry. 2015 Dec 7;21(50):18417-30. doi: 10.1002/chem.201502970. Epub 2015 Nov 4. PMID: 26531322. 5: Yoshida M. [Total Synthesis of Biologically Active Natural Products toward Elucidation of the Mode of Action]. Yakugaku Zasshi. 2015;135(10):1099-108. Japanese. doi: 10.1248/yakushi.15-00184. PMID: 26423864. 6: Taibon J, Sturm S, Seger C, Werth M, Strasser H, Stuppner H. Supercritical Fluid Chromatography as an Alternative Tool for the Qualitative and Quantitative Analysis of Metarhizium brunneum Metabolites from Culture Broth. Planta Med. 2015 Dec;81(18):1736-43. doi: 10.1055/s-0035-1557823. Epub 2015 Sep 14. Erratum in: Planta Med. 2015 Dec;81(18):E6. PMID: 26366754. 7: Taibon J, Sturm S, Seger C, Strasser H, Stuppner H. Quantitative Assessment of Destruxins from Strawberry and Maize in the Lower Parts per Billion Range: Combination of a QuEChERS-Based Extraction Protocol with a Fast and Selective UHPLC-QTOF-MS Assay. J Agric Food Chem. 2015 Jun 17;63(23):5707-13. doi: 10.1021/acs.jafc.5b01562. Epub 2015 Jun 8. PMID: 26005897. 8: Golo PS, Gardner DR, Grilley MM, Takemoto JY, Krasnoff SB, Pires MS, Fernandes ÉK, Bittencourt VR, Roberts DW. Production of destruxins from Metarhizium spp. fungi in artificial medium and in endophytically colonized cowpea plants. PLoS One. 2014 Aug 15;9(8):e104946. doi: 10.1371/journal.pone.0104946. PMID: 25127450; PMCID: PMC4134251. 9: Dong C, Yu J, Zhu Y, Dong C. Inhibition of hepatitis B virus gene expression & replication by crude destruxins from Metarhizium anisopliae var. dcjhyium. Indian J Med Res. 2013 Dec;138(6):969-76. PMID: 24521644; PMCID: PMC3978990. 10: Yoshida M, Sato H, Ishida Y, Nakagawa H, Doi T. Scalable solution-phase synthesis of the biologically active cyclodepsipeptide destruxin E, a potent negative regulator of osteoclast morphology. J Org Chem. 2014 Jan 3;79(1):296-306. doi: 10.1021/jo402437z. Epub 2013 Nov 22. PMID: 24251640. 11: Dornetshuber-Fleiss R, Heffeter P, Mohr T, Hazemi P, Kryeziu K, Seger C, Berger W, Lemmens-Gruber R. Destruxins: fungal-derived cyclohexadepsipeptides with multifaceted anticancer and antiangiogenic activities. Biochem Pharmacol. 2013 Aug 1;86(3):361-77. doi: 10.1016/j.bcp.2013.05.022. Epub 2013 Jun 6. PMID: 23747344; PMCID: PMC5850990. 12: Yoshida M, Takeuchi H, Ishida Y, Yashiroda Y, Yoshida M, Takagi M, Shin-ya K, Doi T. Synthesis, structure determination, and biological evaluation of destruxin E. Org Lett. 2010 Sep 3;12(17):3792-5. doi: 10.1021/ol101449x. PMID: 20672849. 13: Hutwimmer S, Wang H, Strasser H, Burgstaller W. Formation of exudate droplets by Metarhizium anisopliae and the presence of destruxins. Mycologia. 2010 Jan-Feb;102(1):1-10. doi: 10.3852/09-079. PMID: 20120222. 14: Itoh N, Okochi M, Tagami S, Nishitomi K, Nakayama T, Yanagida K, Fukumori A, Jiang J, Mori K, Hosono M, Kikuchi J, Nakano Y, Takinami Y, Dohi K, Nishigaki A, Takemoto H, Minagawa K, Katoh T, Willem M, Haass C, Morihara T, Tanaka T, Kudo T, Hasegawa H, Nishimura M, Sakaguchi G, Kato A, Takeda M. Destruxin E decreases Beta-amyloid generation by reducing colocalization of beta-amyloid-cleaving enzyme 1 and beta-amyloid protein precursor. Neurodegener Dis. 2009;6(5-6):230-9. doi: 10.1159/000236902. Epub 2009 Sep 9. PMID: 19738368. 15: Male KB, Tzeng YM, Montes J, Liu BL, Liao WC, Kamen A, Luong JH. Probing inhibitory effects of destruxins from Metarhizium anisopliae using insect cell based impedance spectroscopy: inhibition vs chemical structure. Analyst. 2009 Jul;134(7):1447-52. doi: 10.1039/b822133b. Epub 2009 Apr 15. PMID: 19562214. 16: Sowjanya Sree K, Padmaja V, Murthy YL. Insecticidal activity of destruxin, a mycotoxin from Metarhizium anisopliae (Hypocreales), against Spodoptera litura (Lepidoptera: Noctuidae) larval stages. Pest Manag Sci. 2008 Feb;64(2):119-25. doi: 10.1002/ps.1480. PMID: 17935266. 17: Vázquez MJ, Albarrán MI, Espada A, Rivera-Sagredo A, Díez E, Hueso-Rodríguez JA. A new destruxin as inhibitor of vacuolar-type H+-ATPase of Saccharomyces cerevisiae. Chem Biodivers. 2005 Jan;2(1):123-30. doi: 10.1002/cbdv.200490163. PMID: 17191925. 18: Lira SP, Vita-Marques AM, Seleghim MH, Bugni TS, LaBarbera DV, Sette LD, Sponchiado SR, Ireland CM, Berlinck RG. New destruxins from the marine-derived fungus Beauveria felina. J Antibiot (Tokyo). 2006 Sep;59(9):553-63. doi: 10.1038/ja.2006.76. PMID: 17136888. 19: Rao YK, Tsou CH, Tzeng YM. Antioxidants enhanced production of destruxin E from cultivation of Metarhizium anisopliae. Appl Microbiol Biotechnol. 2006 Dec;73(3):519-24. doi: 10.1007/s00253-006-0493-4. Epub 2006 Jul 5. PMID: 16820952. 20: Skrobek A, Butt TM. Toxicity testing of destruxins and crude extracts from the insect-pathogenic fungus Metarhizium anisopliae. FEMS Microbiol Lett. 2005 Oct 1;251(1):23-8. doi: 10.1016/j.femsle.2005.07.029. PMID: 16102914.