Elsinochrome A | CAS#24568-67-0 | Anticancer fungal metabolite

MedKoo Cat#: 464092 | Name: Elsinochrome A

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Description:

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

Elsinochrome A is a perylenequinone fungal metabolite that has been found in Hypomyces and has anticancer activity. Photoactivation of elsinochrome A induces the production of singlet oxygen and apoptosis in R366.4 rhesus monkey embryonic stem cells and HCe-8693 colorectal carcinoma cells when used at concentrations ranging from 1 to 100 µM.

Chemical Structure

Elsinochrome A

CAS#24568-67-0

Theoretical Analysis

MedKoo Cat#: 464092

Name: Elsinochrome A

CAS#: 24568-67-0

Chemical Formula: C30H24O10

Exact Mass: 544.1369

Molecular Weight: 544.51

Elemental Analysis: C, 66.17; H, 4.44; O, 29.38

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 550.00	2 Weeks
5mg	USD 1,400.00	2 Weeks

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Related CAS #

No Data

Synonym

Elsinochrome A; Elsinochrome-A; NSC 623609; NSC623609; NSC-623609;

IUPAC/Chemical Name

(1R,2R)-1,2-diacetyl-5,10-dihydroxy-3,7,8,12-tetramethoxy-1,2-dihydrobenzo[ghi]perylene-4,11-dione

InChi Key

WTZSLZBEQHGTRK-HZPDHXFCSA-N

InChi Code

InChI=1S/C30H24O10/c1-9(31)15-16(10(2)32)26-24-22-18(28(36)30(26)40-6)12(34)8-14(38-4)20(22)19-13(37-3)7-11(33)17-21(19)23(24)25(15)29(39-5)27(17)35/h7-8,15-16,33-34H,1-6H3/t15-,16-/m1/s1

SMILES Code

CC([C@H]1C(C2=C(C3=C4C(OC)=CC(O)=C5C4=C2C([C@@H]1C(C)=O)=C(C5=O)OC)C6=C(O)C=C3OC)=C(C6=O)OC)=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

>2 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

	Solvent	mg/mL	mM
Solubility
	Soluble in DMSO	0.0	100.00

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 544.51 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: Hu J, Sarrami F, Li H, Zhang G, Stubbs KA, Lacey E, Stewart SG, Karton A, Piggott AM, Chooi YH. Heterologous biosynthesis of elsinochrome A sheds light on the formation of the photosensitive perylenequinone system. Chem Sci. 2018 Nov 22;10(5):1457-1465. doi: 10.1039/c8sc02870b. PMID: 30809363; PMCID: PMC6354827. 2: Zhang Y, Xie J, Zhang L, Li C, Chen H, Gu Y, Zhao J. A novel elsinochrome A derivative: a study of drug delivery and photodynamic activity. Photochem Photobiol Sci. 2009 Dec;8(12):1676-82. doi: 10.1039/b9pp00046a. Epub 2009 Oct 12. PMID: 20024164. 3: Surup F, Pommerehne K, Schroers HJ, Stadler M. Elsinopirins A-D, Decalin Polyketides from the Ascomycete Elsinoё pyri. Biomolecules. 2018 Feb 5;8(1):8. doi: 10.3390/biom8010008. PMID: 29401753; PMCID: PMC5871977. 4: Chooi YH, Zhang G, Hu J, Muria-Gonzalez MJ, Tran PN, Pettitt A, Maier AG, Barrow RA, Solomon PS. Functional genomics-guided discovery of a light-activated phytotoxin in the wheat pathogen Parastagonospora nodorum via pathway activation. Environ Microbiol. 2017 May;19(5):1975-1986. doi: 10.1111/1462-2920.13711. Epub 2017 Apr 10. PMID: 28251756. 5: Chung KR. Elsinoë fawcettii and Elsinoë australis: the fungal pathogens causing citrus scab. Mol Plant Pathol. 2011 Feb;12(2):123-35. doi: 10.1111/j.1364-3703.2010.00663.x. Epub 2010 Oct 1. PMID: 21199563; PMCID: PMC6640467. 6: Yang SL, Chung KR. Transcriptional regulation of elsinochrome phytotoxin biosynthesis by an EfSTE12 activator in the citrus scab pathogen Elsinoë fawcettii. Fungal Biol. 2010 Jan;114(1):64-73. doi: 10.1016/j.mycres.2009.10.007. Epub 2009 Nov 4. PMID: 20965063. 7: Boss D, Maurhofer M, Schläpfer E, Défago G. Elsinochrome A production by the bindweed biocontrol fungus Stagonospora convolvuli LA39 does not pose a risk to the environment or the consumer of treated crops. FEMS Microbiol Ecol. 2007 Jan;59(1):194-205. doi: 10.1111/j.1574-6941.2006.00207.x. Epub 2006 Nov 9. PMID: 17092310. 8: Ma F, Zhou L, Wang W, Feng YY, Zhou JH, Wang XH, Shen J. [Spectroscopic studies on the interaction of Elsinochrome A with myoglobin]. Guang Pu Xue Yu Guang Pu Fen Xi. 2011 Jun;31(6):1601-5. Chinese. PMID: 21847942. 9: Chung KR, Liao HL. Determination of a transcriptional regulator-like gene involved in biosynthesis of elsinochrome phytotoxin by the citrus scab fungus, Elsinoë fawcettii. Microbiology (Reading). 2008 Nov;154(Pt 11):3556-3566. doi: 10.1099/mic.0.2008/019414-0. PMID: 18957608. 10: Jeffress S, Arun-Chinnappa K, Stodart B, Vaghefi N, Tan YP, Ash G. Genome mining of the citrus pathogen Elsinoë fawcettii; prediction and prioritisation of candidate effectors, cell wall degrading enzymes and secondary metabolite gene clusters. PLoS One. 2020 May 29;15(5):e0227396. doi: 10.1371/journal.pone.0227396. PMID: 32469865; PMCID: PMC7259788. 11: Meille SV, Malpezzi L, Allegra G, Nasini G, Weiss U. Structure of elsinochrome A: a perylenequinone metabolite. Acta Crystallogr C. 1989 Apr 15;45 ( Pt 4):628-32. doi: 10.1107/s0108270188012831. PMID: 2610978. 12: Ma YJ, Zheng LP, Wang JW. Inducing perylenequinone production from a bambusicolous fungus Shiraia sp. S9 through co-culture with a fruiting body- associated bacterium Pseudomonas fulva SB1. Microb Cell Fact. 2019 Jul 5;18(1):121. doi: 10.1186/s12934-019-1170-5. PMID: 31277643; PMCID: PMC6612088. 13: Liao HL, Chung KR. Genetic dissection defines the roles of elsinochrome Phytotoxin for fungal pathogenesis and conidiation of the citrus pathogen Elsinoë fawcettii. Mol Plant Microbe Interact. 2008 Apr;21(4):469-79. doi: 10.1094/MPMI-21-4-0469. PMID: 18321192. 14: Fürtges L, Obermaier S, Thiele W, Foegen S, Müller M. Diversity in Fungal Intermolecular Phenol Coupling of Polyketides: Regioselective Laccase-Based Systems. Chembiochem. 2019 Aug 1;20(15):1928-1932. doi: 10.1002/cbic.201900041. Epub 2019 Jul 8. PMID: 30868712. 15: Chen CT, Nakanishi K, Natori S. Biosynthesis of elsinochrome A, the perylenequinone from Elsinoë spp. I. Chem Pharm Bull (Tokyo). 1966 Dec;14(12):1434-7. doi: 10.1248/cpb.14.1434. PMID: 5981250. 16: Wei G, Yan M, Dong R, Wang D, Zhou X, Chen J, Hao J. Covalent modification of reduced graphene oxide by means of diazonium chemistry and use as a drug- delivery system. Chemistry. 2012 Nov 12;18(46):14708-16. doi: 10.1002/chem.201200843. Epub 2012 Sep 27. PMID: 23018420. 17: Shen L. Theoretical study on the photophysical and photochemical properties of elsinochrome A. J Biomol Struct Dyn. 2007 Dec;25(3):321-6. doi: 10.1080/07391102.2007.10507180. PMID: 17937493. 18: Favilla M, Macchia L, Gallo A, Altomare C. Toxicity assessment of metabolites of fungal biocontrol agents using two different (Artemia salina and Daphnia magna) invertebrate bioassays. Food Chem Toxicol. 2006 Nov;44(11):1922-31. doi: 10.1016/j.fct.2006.06.024. Epub 2006 Jul 13. PMID: 16935403. 19: Ma L, Tai H, Li C, Zhang Y, Wang ZH, Ji WZ. Photodynamic inhibitory effects of three perylenequinones on human colorectal carcinoma cell line and primate embryonic stem cell line. World J Gastroenterol. 2003 Mar;9(3):485-90. doi: 10.3748/wjg.v9.i3.485. PMID: 12632502; PMCID: PMC4621566. 20: Zhao N, Yu Y, Yue Y, Dou M, Guo B, Yan S, Chen S. Nitric oxide regulates perylenequinones biosynthesis in Shiraia bambusicola S4201 induced by hydrogen peroxide. Sci Rep. 2021 Jan 27;11(1):2365. doi: 10.1038/s41598-021-81990-2. PMID: 33504905; PMCID: PMC7840948.