Sclerotiorin | CAS#549-23-5 | antiplatelet

MedKoo Cat#: 461937 | Name: Sclerotiorin

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Description:

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

Sclerotiorin is a compound isolated from the fermented broth of Penicillium frequentans that exhibited potent inhibition against human polymorphonuclear leukocytes 5-lipoxygenase and human platelet aggregation.

Chemical Structure

Sclerotiorin

CAS#549-23-5

Theoretical Analysis

MedKoo Cat#: 461937

Name: Sclerotiorin

CAS#: 549-23-5

Chemical Formula: C21H23ClO5

Exact Mass: 390.1234

Molecular Weight: 390.86

Elemental Analysis: C, 64.53; H, 5.93; Cl, 9.07; O, 20.47

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 1,100.00	2 weeks
10mg	USD 1,750.00	2 weeks

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Related CAS #

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Synonym

Sclerotiorin;

IUPAC/Chemical Name

(R)-5-chloro-3-((S,1E,3E)-3,5-dimethylhepta-1,3-dien-1-yl)-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl acetate

InChi Key

SWJLTKXURNHVHE-UPWXJBBJSA-N

InChi Code

InChI=1S/C21H23ClO5/c1-6-12(2)9-13(3)7-8-15-10-16-17(11-26-15)19(24)21(5,27-14(4)23)20(25)18(16)22/h7-12H,6H2,1-5H3/b8-7+,13-9+/t12-,21+/m0/s1

SMILES Code

O=C1[C@](C)(OC(C)=O)C(C2=COC(/C=C/C(C)=C/[C@@H](C)CC)=CC2=C1Cl)=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, DMF, and ethanol

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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Sclerotiorin inhibits soybean lipoxygenase-1 with an IC50 value of 4.2 µM.1 Sclerotiorin also exhibits a number of other activities including inhibition of cholesterol ester transfer protein (IC50 = 19.4 µM), inhibition of Grb2-Shc interaction (IC50 = 22 µM), and antagonism of endothelin receptors (IC50 = 114 and 152 µM for human ETA and ETB, respectively).

In vitro activity:

Sclerotiorin may have potential in Alzheimer’s disease treatment. In vitro, sclerotiorin potently delayed both seeded and nonseeded Aβ42 polymerization in cell-free assays. Sclerotiorin kinetically stabilize small Aβ42 oligomers, which inhibits fibrillogenesis. The self-assembly of Aβ42 into fibrillar aggregates is associated with neuronal dysfunction and toxicity in Alzheimer's patient brains, suggesting that small molecules, like sclerotiorin, acting on this process might interfere with pathogenesis. Reference: J Mol Biol. 2020 Mar 27;432(7):2080-2098. https://pubmed.ncbi.nlm.nih.gov/32061932/

In vivo activity:

To be determined

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	76.75
	DMSO	20.0	51.17
	Ethanol	3.0	7.68

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 390.86 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

Formulation protocol:

1. Wiglenda T, Groenke N, Hoffmann W, Manz C, Diez L, Buntru A, Brusendorf L, Neuendorf N, Schnoegl S, Haenig C, Schmieder P, Pagel K, Wanker EE. Sclerotiorin Stabilizes the Assembly of Nonfibrillar Abeta42 Oligomers with Low Toxicity, Seeding Activity, and Beta-sheet Content. J Mol Biol. 2020 Mar 27;432(7):2080-2098. doi: 10.1016/j.jmb.2020.01.033. Epub 2020 Feb 13. PMID: 32061932. 2. Chen D, Ma S, He L, Yuan P, She Z, Lu Y. Sclerotiorin inhibits protein kinase G from Mycobacterium tuberculosis and impairs mycobacterial growth in macrophages. Tuberculosis (Edinb). 2017 Mar;103:37-43. doi: 10.1016/j.tube.2017.01.001. Epub 2017 Jan 12. PMID: 28237032.

In vitro protocol:

In vivo protocol:

To be determined

1: Chidananda C, Vasantha KY, Sattur AP. Sclerotiorin is non-mutagenic and inhibits human PMNL 5-lipoxygenase and platelet aggregation. Indian J Exp Biol. 2015 Apr;53(4):228-31. PubMed PMID: 26011984. 2: Corrêia Gomes D, Takahashi JA. Sequential fungal fermentation-biotransformation process to produce a red pigment from sclerotiorin. Food Chem. 2016 Nov 1;210:355-61. doi: 10.1016/j.foodchem.2016.04.057. Epub 2016 Apr 26. PubMed PMID: 27211658. 3: Lin L, Mulholland N, Huang SW, Beattie D, Irwin D, Gu YC, Clough J, Wu QY, Yang GF. Design, synthesis and fungicidal activity of novel sclerotiorin derivatives. Chem Biol Drug Des. 2012 Nov;80(5):682-92. doi: 10.1111/cbdd.12005. Epub 2012 Aug 31. PubMed PMID: 22834771. 4: Giridharan P, Verekar SA, Khanna A, Mishra PD, Deshmukh SK. Anticancer activity of sclerotiorin, isolated from an endophytic fungus Cephalotheca faveolata Yaguchi, Nishim. & Udagawa. Indian J Exp Biol. 2012 Jul;50(7):464-8. PubMed PMID: 22822525. 5: Lin L, Mulholland N, Wu QY, Beattie D, Huang SW, Irwin D, Clough J, Gu YC, Yang GF. Synthesis and antifungal activity of novel sclerotiorin analogues. J Agric Food Chem. 2012 May 9;60(18):4480-91. doi: 10.1021/jf300610j. Epub 2012 Apr 25. PubMed PMID: 22439963. 6: Germain AR, Bruggemeyer DM, Zhu J, Genet C, O'Brien P, Porco JA. Synthesis of the azaphilones (+)-sclerotiorin and (+)-8-O-methylsclerotiorinamine utilizing (+)-sparteine surrogates in copper-mediated oxidative dearomatization. J Org Chem. 2011 Apr 15;76(8):2577-84. doi: 10.1021/jo102448n. Epub 2011 Mar 14. PubMed PMID: 21401026; PubMed Central PMCID: PMC3086581. 7: Bao L, Xu Z, Niu SB, Namikoshi M, Kobayashi H, Liu HW. (-)-Sclerotiorin from an unidentified marine fungus as an anti-meiotic and anti-fungal agent. Nat Prod Commun. 2010 Nov;5(11):1789-92. PubMed PMID: 21213982. 8: Chidananda C, Sattur AP. Sclerotiorin, a novel inhibitor of lipoxygenase from Penicillium frequentans. J Agric Food Chem. 2007 Apr 18;55(8):2879-83. Epub 2007 Mar 27. PubMed PMID: 17385879. 9: Kabbaj FZ, Lu S, Faouzi Mel A, Meddah B, Proksch P, Cherrah Y, Altenbach HJ, Aly AH, Chadli A, Debbab A. Bioactive metabolites from Chaetomium aureum: structure elucidation and inhibition of the Hsp90 machine chaperoning activity. Bioorg Med Chem. 2015 Jan 1;23(1):126-31. doi: 10.1016/j.bmc.2014.11.021. Epub 2014 Nov 20. PubMed PMID: 25482429; PubMed Central PMCID: PMC4274242. 10: Raina S, Odell M, Keshavarz T. Quorum sensing as a method for improving sclerotiorin production in Penicillium sclerotiorum. J Biotechnol. 2010 Jul 20;148(2-3):91-8. doi: 10.1016/j.jbiotec.2010.04.009. Epub 2010 May 7. PubMed PMID: 20438771. 11: BIRKINSHAW JH, CHAPLEN P. Studies in the biochemistry of micro-organisms. 105. Chemical degradation of sclerotiorin. Biochem J. 1958 Aug;69(4):505-9. PubMed PMID: 13572310; PubMed Central PMCID: PMC1196590. 12: Chidananda C, Rao LJ, Sattur AP. Sclerotiorin, from Penicillium frequentans, a potent inhibitor of aldose reductase. Biotechnol Lett. 2006 Oct;28(20):1633-6. Epub 2006 Aug 10. PubMed PMID: 16900332. 13: Chen D, Ma S, He L, Yuan P, She Z, Lu Y. Sclerotiorin inhibits protein kinase G from Mycobacterium tuberculosis and impairs mycobacterial growth in macrophages. Tuberculosis (Edinb). 2017 Mar;103:37-43. doi: 10.1016/j.tube.2017.01.001. Epub 2017 Jan 12. PubMed PMID: 28237032. 14: Takenaka Y, Tanahashi T, Nagakura N, Hamada N. Production of xanthones with free radical scavenging properties, emodin and sclerotiorin by the cultured lichen mycobionts of Pyrenula japonica. Z Naturforsch C. 2000 Nov-Dec;55(11-12):910-4. PubMed PMID: 11204195. 15: Cheung RC, Wong JH, Pan WL, Chan YS, Yin CM, Dan XL, Wang HX, Fang EF, Lam SK, Ngai PH, Xia LX, Liu F, Ye XY, Zhang GQ, Liu QH, Sha O, Lin P, Ki C, Bekhit AA, Bekhit Ael-D, Wan DC, Ye XJ, Xia J, Ng TB. Antifungal and antiviral products of marine organisms. Appl Microbiol Biotechnol. 2014 Apr;98(8):3475-94. doi: 10.1007/s00253-014-5575-0. Epub 2014 Feb 23. Review. PubMed PMID: 24562325; PubMed Central PMCID: PMC5300219. 16: Xiao BH, She ZG, Lei XL, Chen B, Huang CH, Xu J. [Secondary metabolites of seaweed endophytic fungi ZJ27 in the South China Sea coast]. Zhong Yao Cai. 2011 Apr;34(4):544-6. Chinese. PubMed PMID: 21809538. 17: BIRKINSHAW JH. Studies in the biochemistry of micro-organisms. Metabolic products of Penicillium multicolor G.-M. and P. with special reference to sclerotiorin. Biochem J. 1952 Oct;52(2):283-8. PubMed PMID: 13018222; PubMed Central PMCID: PMC1197983. 18: Ellestad GA, Whalley WB. The chemistry of fungi. LII. Sclerotiorin. J Chem Soc Perkin 1. 1965 Dec:7260-1. PubMed PMID: 5892027. 19: Somoza AD, Lee KH, Chiang YM, Oakley BR, Wang CC. Reengineering an azaphilone biosynthesis pathway in Aspergillus nidulans to create lipoxygenase inhibitors. Org Lett. 2012 Feb 17;14(4):972-5. doi: 10.1021/ol203094k. Epub 2012 Feb 1. PubMed PMID: 22296232; PubMed Central PMCID: PMC3350772. 20: Chong R, King RR, Whalley WB. The chemistry of fungi. LXI. The synthesis of ( )-sclerotiorin, of ( )-4,6-dimethylocta-trans-2,trans-4-dienoic acid, and of an analogue of rotiorin. J Chem Soc Perkin 1. 1971;21:3566-71. PubMed PMID: 5167264.