Pyrenophorol | CAS# 22248-41-5 | Fungal Metabolite

MedKoo Cat#: 574006 | Name: Pyrenophorol

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Description:

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

Pyrenophorol is a fungal metabolite that has been found in Alternaria and has diverse biological activities. It inhibits human topoisomerase II α when used at concentrations of 75 and 100 μM. It is active against S. cerevisiae (MIC = 4 μM) and M. violaceum. Pyrenophorol induces leaf necrosis and chlorophyll retention in wild oats when used at a concentration of 64 μM.

Chemical Structure

Pyrenophorol

CAS#22248-41-5

Theoretical Analysis

MedKoo Cat#: 574006

Name: Pyrenophorol

CAS#: 22248-41-5

Chemical Formula: C16H24O6

Exact Mass: 312.1573

Molecular Weight: 312.36

Elemental Analysis: C, 61.52; H, 7.74; O, 30.73

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 400.00

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Synonym

Pyrenophorol

IUPAC/Chemical Name

(3E,5S,8R,11E,13S,16R)-5,13-dihydroxy-8,16-dimethyl-1,9-dioxacyclohexadeca-3,11-diene-2,10-dione

InChi Key

RBQNDQOKFICJGL-UTBFYLPBSA-N

InChi Code

InChI=1S/C16H24O6/c1-11-3-5-13(17)8-10-16(20)22-12(2)4-6-14(18)7-9-15(19)21-11/h7-14,17-18H,3-6H2,1-2H3/b9-7+,10-8+/t11-,12-,13+,14+/m1/s1

SMILES Code

O=C(O[C@H](C)CC[C@H](O)/C=C/1)/C=C/[C@@H](O)CC[C@@H](C)OC1=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

>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 312.36 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: Chibuye B, Singh IS, Chimuka L, Maseka KK. In silico and ADMET molecular analysis targeted to discover novel anti-inflammatory drug candidates as COX-2 inhibitors from specific metabolites of Diospyros batokana (Ebenaceae). Biochem Biophys Rep. 2024 Jul 13;39:101758. doi: 10.1016/j.bbrep.2024.101758. PMID: 39108619; PMCID: PMC11301067. 2: Zhang X, Pang X, Zhang L, Li Y, Song Y, Xiao H, Liu Y, Wang J, Yan Y. Genome Mining Uncovers a Flavoenzyme-Catalyzed Isomerization Process during the Maturation of Pyrenophorol Dilactones. Org Lett. 2024 Mar 1;26(8):1612-1617. doi: 10.1021/acs.orglett.4c00008. Epub 2024 Feb 20. PMID: 38377309. 3: Narala SG, Nagalatha G, Venkat Narsaiah A. Stereoselective total synthesis of C2-symmetric natural products pyrenophorol and its derivatives. Nat Prod Res. 2020 Aug;34(15):2173-2178. doi: 10.1080/14786419.2019.1577843. Epub 2019 Mar 1. PMID: 30822134. 4: Alluraiah G, Sreenivasulu R, Chandrasekhar C, Raju RR. An alternative stereoselective total synthesis of (-)-pyrenophorol. Nat Prod Res. 2019 Oct;33(19):2738-2743. doi: 10.1080/14786419.2018.1499636. Epub 2018 Sep 17. PMID: 30220222. 5: Jarolim K, Del Favero G, Ellmer D, Stark TD, Hofmann T, Sulyok M, Humpf HU, Marko D. Dual effectiveness of Alternaria but not Fusarium mycotoxins against human topoisomerase II and bacterial gyrase. Arch Toxicol. 2017 Apr;91(4):2007-2016. doi: 10.1007/s00204-016-1855-z. Epub 2016 Sep 28. PMID: 27682608; PMCID: PMC5364253. 6: Risi RM, Maza AM, Burke SD. Asymmetric hydroformylation-initiated tandem sequences for syntheses of (+)-patulolide C, (-)-pyrenophorol, (+)-decarestrictine L, and (+)-prelog djerassi lactone. J Org Chem. 2015 Jan 2;80(1):204-16. doi: 10.1021/jo502301k. Epub 2014 Dec 1. PMID: 25398097. 7: Chatterjee S, Ghadigaonkar S, Sur P, Sharma A, Chattopadhyay S. A chemoenzymatic synthesis of hept-6-ene-2,5-diol stereomers: application to asymmetric synthesis of decarestrictine L, pyrenophorol, and stagonolide E. J Org Chem. 2014 Sep 5;79(17):8067-76. doi: 10.1021/jo5012575. Epub 2014 Aug 19. PMID: 25116794. 8: Liu S, Guo L, Che Y, Liu L. Pestaloficiols Q-S from the plant endophytic fungus Pestalotiopsis fici. Fitoterapia. 2013 Mar;85:114-8. doi: 10.1016/j.fitote.2013.01.010. Epub 2013 Jan 23. PMID: 23353656. 9: Trost BM, Quintard A. Asymmetric catalytic alkynylation of acetaldehyde: application to the synthesis of (+)-tetrahydropyrenophorol. Angew Chem Int Ed Engl. 2012 Jul 2;51(27):6704-8. doi: 10.1002/anie.201203035. Epub 2012 Jun 5. PMID: 22674869; PMCID: PMC3428070. 10: Sumarah MW, Kesting JR, Sørensen D, Miller JD. Antifungal metabolites from fungal endophytes of Pinus strobus. Phytochemistry. 2011 Oct;72(14-15):1833-7. doi: 10.1016/j.phytochem.2011.05.003. Epub 2011 May 31. PMID: 21632082. 11: Aliferis KA, Materzok S, Paziotou GN, Chrysayi-Tokousbalides M. Lemna minor L. as a model organism for ecotoxicological studies performing 1H NMR fingerprinting. Chemosphere. 2009 Aug;76(7):967-73. doi: 10.1016/j.chemosphere.2009.04.025. Epub 2009 May 13. PMID: 19443011. 12: Chrysayi-Tokousbalides M, Machera K, Kyriakopoulou K, Aliferis KA, Schrader KK, Tsoutsanis I, Anastasiadou P. Comparative toxicity of the phytotoxins (8R,16R)-(-)-pyrenophorin and (5S,8R,13S,16R)-(-)-pyrenophorol on aquatic organisms. Bull Environ Contam Toxicol. 2007 Nov;79(5):499-503. doi: 10.1007/s00128-007-9223-6. Epub 2007 Sep 25. PMID: 17898918. 13: Aliferis KA, Chrysayi-Tokousbalides M. Metabonomic strategy for the investigation of the mode of action of the phytotoxin (5S,8R,13S,16R)-(-)-pyrenophorol using 1H nuclear magnetic resonance fingerprinting. J Agric Food Chem. 2006 Mar 8;54(5):1687-92. doi: 10.1021/jf0527798. PMID: 16506820. 14: Kastanias MA, Chrysayi-Tokousbalides M. Bioactivity of the fungal metabolite (8R,16R)-(-)-pyrenophorin on graminaceous plants. J Agric Food Chem. 2005 Jul 27;53(15):5943-7. doi: 10.1021/jf050792m. PMID: 16028978.