Rugulosin | CAS#23537-16-8 | pigment

MedKoo Cat#: 461143 | Name: Rugulosin

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Description:

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

Rugulosin is bis-anthraquinoid pigment produced by fungi such as Penicillium rugulosum Thom, P. tardum and others.

Chemical Structure

Rugulosin

CAS#23537-16-8

Theoretical Analysis

MedKoo Cat#: 461143

Name: Rugulosin

CAS#: 23537-16-8

Chemical Formula: C30H22O10

Exact Mass: 542.1213

Molecular Weight: 542.50

Elemental Analysis: C, 66.42; H, 4.09; O, 29.49

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1mg	USD 350.00

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Synonym

Rugulosin; Radicalisin;

IUPAC/Chemical Name

(5aS,6S,13aR,14S,17R,18S,19R,20R)-1,7,9,15,17,20-hexahydroxy-3,11-dimethyl-14-hydro-5H,6H-6,13a,5a,14-(epibutane[1,2,3,4]tetrayl)cycloocta[1,2-b:5,6-b']dinaphthalene-5,8,13,16-tetraone

InChi Key

OYNIPTDPTUSUAY-WGZAVFAOSA-N

InChi Code

InChI=1S/C30H22O10/c1-7-3-9-13(11(31)5-7)21(33)17-25(37)20-23(35)15-16-24(36)19(29(15,17)27(9)39)26(38)18-22(34)14-10(28(40)30(16,18)20)4-8(2)6-12(14)32/h3-6,15-16,19-20,23-24,31-32,35-38H,1-2H3/t15-,16+,19-,20-,23+,24+,29-,30+/m0/s1

SMILES Code

Cc1cc(O)c(C(C2=C(O)[C@@H]3[C@@H]4O)=O)c(C([C@]52[C@H]4[C@H]6[C@@]3(C(c7c(C8=O)c(O)cc(C)c7)=O)C8=C(O)[C@@H]5[C@@H]6O)=O)c1

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

To be determined

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:

(+)-Rugulosin inhibits HIV-1 integrase activity with IC50 values of 19 and 25 µM in coupled and strand transfer assays, respectively. It also inhibits ribonuclease H in rat liver. (+)-Rugulosin leads to hepatic injury and liver cell hyperplasia in mice. It is cytotoxic to insect cells but not mammalian C6/36, L929, and HepG2 cells (ID50s = 1.2, >200, 23.7, and >200 µg/ml, respectively).

In vitro activity:

Rugulosin inhibited the penetration of phage RNA into host bacteris, preventing the phage's genetic material from entering and infecting the bacterial cells. Rugulosin also inhibits the in vitro RNA synthesis by Qβ replicase. Reference: Jpn J Microbiol. 1971 Mar;15(2):121-9. https://pubmed.ncbi.nlm.nih.gov/4930807/

In vivo activity:

Rugulosin exhibited hepatocarcinogenic potential in male mice. When exposed to a diet containing rugulosin, mice experienced acute hepatic injury characterized by fatty degeneration and liver cell necrosis, with some succumbing to these effects. Additionally, long-term exposure to rugulosin resulted in the development of hepatocellular carcinoma in a subset of surviving mice, while lower doses led to the formation of hyperplastic nodules in liver cells.. Reference: J Toxicol Sci. 1980 Nov;5(4):295-302. https://pubmed.ncbi.nlm.nih.gov/7218376/

Preparing Stock Solutions

The following data is based on the product molecular weight 542.50 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. Nakamura S, Nii F, Shimizu M, Watanabe I, Haruna I. Inhibition of phage growth by an antibiotic rugulosin isolated from Myrothecium verucaria. II. The mechanism of action. Jpn J Microbiol. 1971 Mar;15(2):121-9. doi: 10.1111/j.1348-0421.1971.tb00561.x. PMID: 4930807. 2. Ueno Y, Sato N, Ito T, Ueno I, Enomoto M, Tsunoda H. Chronic toxicity and hepatocarcinogenicity of (+) rugulosin, an anthraquinoid mycotoxin from penicillium species: preliminary surveys in mice. J Toxicol Sci. 1980 Nov;5(4):295-302. doi: 10.2131/jts.5.295. PMID: 7218376.

In vitro protocol:

In vivo protocol:

1. Ueno Y, Sato N, Ito T, Ueno I, Enomoto M, Tsunoda H. Chronic toxicity and hepatocarcinogenicity of (+) rugulosin, an anthraquinoid mycotoxin from penicillium species: preliminary surveys in mice. J Toxicol Sci. 1980 Nov;5(4):295-302. doi: 10.2131/jts.5.295. PMID: 7218376.

1: Rugulosin. IARC Monogr Eval Carcinog Risk Chem Hum. 1986;40:99-106. PubMed PMID: 3473019. 2: Snider BB, Gao X. Efficient syntheses of rugulosin analogues. J Org Chem. 2005 Aug 19;70(17):6863-9. PubMed PMID: 16095306. 3: Nicolaou KC, Lim YH, Papageorgiou CD, Piper JL. Total synthesis of (+)-rugulosin and (+)-2,2'-epi-cytoskyrin A through cascade reactions. Angew Chem Int Ed Engl. 2005 Dec 9;44(48):7917-21. PubMed PMID: 16342134. 4: Sumarah MW, Miller JD, Adams GW. Measurement of a rugulosin-producing endophyte in white spruce seedlings. Mycologia. 2005 Jul-Aug;97(4):770-6. PubMed PMID: 16457346. 5: Miller JD, Sumarah MW, Adams GW. Effect of a rugulosin-producing endophyte in Picea glauca on Choristoneura fumiferana. J Chem Ecol. 2008 Mar;34(3):362-8. doi: 10.1007/s10886-007-9412-0. Epub 2008 Feb 12. PubMed PMID: 18266038. 6: Nicolaou KC, Lim YH, Piper JL, Papageorgiou CD. Total syntheses of 2,2'-epi-cytoskyrin A, rugulosin, and the alleged structure of rugulin. J Am Chem Soc. 2007 Apr 4;129(13):4001-13. Epub 2007 Mar 14. PubMed PMID: 17355133. 7: Walker AK, Frasz SL, Seifert KA, Miller JD, Mondo SJ, LaButti K, Lipzen A, Dockter RB, Kennedy MC, Grigoriev IV, Spatafora JW. Full Genome of Phialocephala scopiformis DAOMC 229536, a Fungal Endophyte of Spruce Producing the Potent Anti-Insectan Compound Rugulosin. Genome Announc. 2016 Feb 25;4(1). pii: e01768-15. doi: 10.1128/genomeA.01768-15. Erratum in: Genome Announc. 2016;4(3). pii: e00510-16. doi: 10.1128/genomeA.00510-16. PubMed PMID: 26950333; PubMed Central PMCID: PMC4767923. 8: Lu RL, Bao GH, Hu FL, Huang B, Li CR, Li ZZ. Comparison of cytotoxic extracts from fruiting bodies, infected insects and cultured mycelia of Cordyceps formosana. Food Chem. 2014 Feb 15;145:1066-71. doi: 10.1016/j.foodchem.2013.09.001. Epub 2013 Sep 13. PubMed PMID: 24128585. 9: BREEN J, DACRE JC, RAISTRICK H, SMITH G. Studies in the biochemistry of micro-organisms. 95. Rugulosin, a crystalline colouring matter of Penicillium rugulosum Thom. Biochem J. 1955 Aug;60(4):618-26. PubMed PMID: 13249956; PubMed Central PMCID: PMC1216160. 10: Sumarah MW, Adams GW, Berghout J, Slack GJ, Wilson AM, Miller JD. Spread and persistence of a rugulosin-producing endophyte in Picea glauca seedlings. Mycol Res. 2008 Jun;112(Pt 6):731-6. doi: 10.1016/j.mycres.2008.01.007. Epub 2008 Feb 3. PubMed PMID: 18487038. 11: SHIBATA S, MURAKAMI T, TANAKA O, CHIHARA G, KITAGAWA I, SUMIMOTO M, KANEKO C. The respective identities of endothianin and radicalisin with skyrin and rugulosin; and the structure of skyrin. Pharm Bull. 1955 Apr;3(2):160-1. PubMed PMID: 14394822. 12: Ueno Y, Sato N, Ito T, Ueno I, Enomoto M, Tsunoda H. Chronic toxicity and hepatocarcinogenicity of (+) rugulosin, an anthraquinoid mycotoxin from penicillium species: preliminary surveys in mice. J Toxicol Sci. 1980 Nov;5(4):295-302. PubMed PMID: 7218376. 13: Walker AK, Frasz SL, Seifert KA, Miller JD, Mondo SJ, LaButti K, Lipzen A, Dockter RB, Kennedy MC, Grigoriev IV, Spatafora JW. Erratum for Walker et al., Full Genome of Phialocephala scopiformis DAOMC 229536, a Fungal Endophyte of Spruce Producing the Potent Anti-Insectan Compound Rugulosin. Genome Announc. 2016 May 26;4(3). pii: e00510-16. doi: 10.1128/genomeA.00510-16. PubMed PMID: 27231381; PubMed Central PMCID: PMC4882962. 14: Nakamura S, Nii F, Inoue S, Nakanishi I, Shimizu M. Antiinfluenzal effect of rugulosin. Jpn J Microbiol. 1974 Jan;18(1):1-7. PubMed PMID: 4546729. 15: SHIBATA S, MURAKAMI T, KITAGAWA I, KISHI T. Metabolic products of fungi. VIII. Rugulosin: the structure of dianhydrorugulosin and its relation to the structure of iridoskyrin. Pharm Bull. 1956 Apr;4(2):111-6. PubMed PMID: 13335475. 16: Nakamura S, Nii F, Shimizu M, Watanabe I, Haruna I. Inhibition of phage growth by an antibiotic rugulosin isolated from Myrothecium verucaria. II. The mechanism of action. Jpn J Microbiol. 1971 Mar;15(2):121-9. PubMed PMID: 4930807. 17: Nirma C, Eparvier V, Stien D. Reactivation of antibiosis in the entomogenous fungus Chrysoporthe sp. SNB-CN74. J Antibiot (Tokyo). 2015 Sep;68(9):586-90. doi: 10.1038/ja.2015.36. Epub 2015 Apr 15. PubMed PMID: 25873318. 18: SHIBATA S, SHOJI J, OHTA A, WATANABE M. Metabolic products of fungi. XI. Some observation on the occurrence of skyrin and rugulosin in mold metabolites, with a reference to structural relationship between penicilliopsin and skyrin. Pharm Bull. 1957 Aug;5(4):380-2. PubMed PMID: 13494139. 19: Kobayashi N, Iitaka Y, Shibata S. X-ray structure determination of (+)-dibromodehydrotetrahydrorugulosin, a heavy atom derivative of (+)-rugulosin. Acta Crystallogr B. 1970 Mar 31;26(3):188-201. PubMed PMID: 5467311. 20: Mori S, Kawai K, Nozawa Y, Ogihara Y. The redox reaction and biotransformation of rubroskyrin, a modified bis-anthraquione from Penicillium islandicum Sopp. Nat Toxins. 1998;6(2):85-90. PubMed PMID: 9888634.