Tenellin | CAS# 53823-15-7 | Fungal Metabolite

MedKoo Cat#: 574172 | Name: Tenellin

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Description:

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

Tenellin is a fungal secondary metabolite that inhibits Mg2+-, Ca2+-, and Na+/K+-ATPase activities in erythrocytes. Tenellin is cytotoxic to Sf9 and Sf21 insect cells.

Chemical Structure

Tenellin

CAS#53823-15-7

Theoretical Analysis

MedKoo Cat#: 574172

Name: Tenellin

CAS#: 53823-15-7

Chemical Formula: C21H23NO5

Exact Mass: 369.1576

Molecular Weight: 369.42

Elemental Analysis: C, 68.28; H, 6.28; N, 3.79; O, 21.65

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 700.00
5mg	USD 1,950.00

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Related CAS #

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Synonym

Tenellin

IUPAC/Chemical Name

3-[(2E,4E,6R)-4,6-dimethyl-1-oxo-2,4-octadien-1-yl]-1,4-dihydroxy-5-(4-hydroxyphenyl)-2(1H)-pyridinone

InChi Key

YELFBSBOFKWHSL-UCFWAISOSA-N

InChi Code

InChI=1S/C21H23NO5/c1-4-13(2)11-14(3)5-10-18(24)19-20(25)17(12-22(27)21(19)26)15-6-8-16(23)9-7-15/h5-13,23,25,27H,4H2,1-3H3/b10-5+,14-11+/t13-/m1/s1

SMILES Code

OC1=CC=C(C(C(O)=C2C(/C=C/C(C)=C/[C@H](C)CC)=O)=CN(O)C2=O)C=C1

Appearance

Solid powder

Purity

>95% (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 369.42 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

1: Schmidt K, Cox RJ. Investigation of chain-length selection by the tenellin iterative highly-reducing polyketide synthase. RSC Adv. 2024 Mar 15;14(13):8963-8970. doi: 10.1039/d3ra08463a. PMID: 38495992; PMCID: PMC10941261. 2: Toshe R, Charria-Girón E, Khonsanit A, Luangsa-Ard JJ, Khalid SJ, Schrey H, Ebada SS, Stadler M. Bioprospection of Tenellins Produced by the Entomopathogenic Fungus Beauveria neobassiana. J Fungi (Basel). 2024 Jan 15;10(1):69. doi: 10.3390/jof10010069. PMID: 38248978; PMCID: PMC10821025. 3: Kim JC, Hwang IM, Kim HM, Kim S, Shin TS, Woo SD, Park HW. Rapid analysis of insecticidal metabolites from the entomopathogenic fungus Beauveria bassiana 331R using UPLC-Q-Orbitrap MS. Mycotoxin Res. 2024 Feb;40(1):123-132. doi: 10.1007/s12550-023-00509-y. Epub 2023 Nov 16. Erratum in: Mycotoxin Res. 2024 Feb;40(1):133. doi: 10.1007/s12550-023-00516-z. PMID: 37968430. 4: Chiang CY, Ohashi M, Tang Y. Deciphering chemical logic of fungal natural product biosynthesis through heterologous expression and genome mining. Nat Prod Rep. 2023 Jan 25;40(1):89-127. doi: 10.1039/d2np00050d. PMID: 36125308; PMCID: PMC9906657. 5: Chen B, Sun Y, Li S, Yin Y, Wang C. Inductive Production of the Iron- Chelating 2-Pyridones Benefits the Producing Fungus To Compete for Diverse Niches. mBio. 2021 Dec 21;12(6):e0327921. doi: 10.1128/mbio.03279-21. Epub 2021 Dec 14. PMID: 34903054; PMCID: PMC8669486. 6: Wang H, Peng H, Li W, Cheng P, Gong M. The Toxins of Beauveria bassiana and the Strategies to Improve Their Virulence to Insects. Front Microbiol. 2021 Aug 26;12:705343. doi: 10.3389/fmicb.2021.705343. PMID: 34512581; PMCID: PMC8430825. 7: Yang XL, Friedrich S, Yin S, Piech O, Williams K, Simpson TJ, Cox RJ. Molecular basis of methylation and chain-length programming in a fungal iterative highly reducing polyketide synthase. Chem Sci. 2019 Jul 30;10(36):8478-8489. doi: 10.1039/c9sc03173a. PMID: 31803427; PMCID: PMC6839510. 8: Lin X, Yuan S, Chen S, Chen B, Xu H, Liu L, Li H, Gao Z. Heterologous Expression of Ilicicolin H Biosynthetic Gene Cluster and Production of a New Potent Antifungal Reagent, Ilicicolin J. Molecules. 2019 Jun 18;24(12):2267. doi: 10.3390/molecules24122267. PMID: 31216742; PMCID: PMC6631495. 9: Lobo LS, Luz C, Fernandes ÉK, Juárez MP, Pedrini N. Assessing gene expression during pathogenesis: Use of qRT-PCR to follow toxin production in the entomopathogenic fungus Beauveria bassiana during infection and immune response of the insect host Triatoma infestans. J Invertebr Pathol. 2015 Jun;128:14-21. doi: 10.1016/j.jip.2015.04.004. Epub 2015 Apr 22. PMID: 25912088. 10: Liu L, Zhang J, Chen C, Teng J, Wang C, Luo D. Structure and biosynthesis of fumosorinone, a new protein tyrosine phosphatase 1B inhibitor firstly isolated from the entomogenous fungus Isaria fumosorosea. Fungal Genet Biol. 2015 Aug;81:191-200. doi: 10.1016/j.fgb.2015.03.009. Epub 2015 Apr 6. PMID: 25857260. 11: Jirakkakul J, Cheevadhanarak S, Punya J, Chutrakul C, Senachak J, Buajarern T, Tanticharoen M, Amnuaykanjanasin A. Tenellin acts as an iron chelator to prevent iron-generated reactive oxygen species toxicity in the entomopathogenic fungus Beauveria bassiana. FEMS Microbiol Lett. 2015 Jan;362(2):1-8. doi: 10.1093/femsle/fnu032. Epub 2014 Dec 4. PMID: 25670702. 12: Pahirulzaman KA, Williams K, Lazarus CM. A toolkit for heterologous expression of metabolic pathways in Aspergillus oryzae. Methods Enzymol. 2012;517:241-60. doi: 10.1016/B978-0-12-404634-4.00012-7. PMID: 23084942. 13: Fisch KM, Bakeer W, Yakasai AA, Song Z, Pedrick J, Wasil Z, Bailey AM, Lazarus CM, Simpson TJ, Cox RJ. Rational domain swaps decipher programming in fungal highly reducing polyketide synthases and resurrect an extinct metabolite. J Am Chem Soc. 2011 Oct 19;133(41):16635-41. doi: 10.1021/ja206914q. Epub 2011 Sep 26. PMID: 21899331. 14: Yakasai AA, Davison J, Wasil Z, Halo LM, Butts CP, Lazarus CM, Bailey AM, Simpson TJ, Cox RJ. Nongenetic reprogramming of a fungal highly reducing polyketide synthase. J Am Chem Soc. 2011 Jul 20;133(28):10990-8. doi: 10.1021/ja204200x. Epub 2011 Jun 28. PMID: 21675761. 15: Heneghan MN, Yakasai AA, Halo LM, Song Z, Bailey AM, Simpson TJ, Cox RJ, Lazarus CM. First heterologous reconstruction of a complete functional fungal biosynthetic multigene cluster. Chembiochem. 2010 Jul 26;11(11):1508-12. doi: 10.1002/cbic.201000259. PMID: 20575135. 16: Halo LM, Heneghan MN, Yakasai AA, Song Z, Williams K, Bailey AM, Cox RJ, Lazarus CM, Simpson TJ. Late stage oxidations during the biosynthesis of the 2-pyridone tenellin in the entomopathogenic fungus Beauveria bassiana. J Am Chem Soc. 2008 Dec 31;130(52):17988-96. doi: 10.1021/ja807052c. PMID: 19067514. 17: Halo LM, Marshall JW, Yakasai AA, Song Z, Butts CP, Crump MP, Heneghan M, Bailey AM, Simpson TJ, Lazarus CM, Cox RJ. Authentic heterologous expression of the tenellin iterative polyketide synthase nonribosomal peptide synthetase requires coexpression with an enoyl reductase. Chembiochem. 2008 Mar 3;9(4):585-94. doi: 10.1002/cbic.200700390. PMID: 18266306. 18: Eley KL, Halo LM, Song Z, Powles H, Cox RJ, Bailey AM, Lazarus CM, Simpson TJ. Biosynthesis of the 2-pyridone tenellin in the insect pathogenic fungus Beauveria bassiana. Chembiochem. 2007 Feb 12;8(3):289-97. doi: 10.1002/cbic.200600398. PMID: 17216664. 19: Jeffs LB, Khachatourians GG. Toxic properties of Beauveria pigments on erythrocyte membranes. Toxicon. 1997 Aug;35(8):1351-6. doi: 10.1016/s0041-0101(97)00025-1. PMID: 9278984. 20: Wright JL, Vining LC, McInnes AG, Smith DG, Walter JA. Use of 13C in biosynthetic studies. The labelling pattern in tenellin enriched from isotope- labelled acetate, methionine, and phenylalanine. Can J Biochem. 1977 Jul;55(7):678-85. doi: 10.1139/o77-098. PMID: 560900.