Royleanone | CAS#6812-87-9 | anticancer

MedKoo Cat#: 585019 | Name: Royleanone

Description:

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

Royleanone is a diterpenoid that exhibits potent anticancer effects in LNCaP human prostate carcinoma cells by inducing mitochondrial mediated apoptosis, cell cycle arrest, suppression of cell migration and downregulation of mTOR/PI3K/AKT signalling pathway.

Chemical Structure

Royleanone

CAS#6812-87-9

Theoretical Analysis

MedKoo Cat#: 585019

Name: Royleanone

CAS#: 6812-87-9

Chemical Formula: C20H28O3

Exact Mass: 316.2038

Molecular Weight: 316.44

Elemental Analysis: C, 75.91; H, 8.92; O, 15.17

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Royleanone

IUPAC/Chemical Name

1,4-Phenanthrenedione, 4b,5,6,7,8,8a,9,10-octahydro-3-hydroxy-4b,8,8-trimethyl-2-(1-methylethyl)-, (4bs-trans)-

InChi Key

KZAPVZIQILABNM-RBZFPXEDSA-N

InChi Code

InChI=1S/C20H28O3/c1-11(2)14-16(21)12-7-8-13-19(3,4)9-6-10-20(13,5)15(12)18(23)17(14)22/h11,13,22H,6-10H2,1-5H3/t13-,20-/m0/s1

SMILES Code

O=C1C(C(C)C)=C(O)C(C2=C1CC[C@@]3([H])C(C)(C)CCC[C@]23C)=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 316.44 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: Li CJ, Xia F, Wu R, Tan HS, Xu HX, Xu G, Qin HB. Synthesis and Cytotoxicities of Royleanone Derivatives. Nat Prod Bioprospect. 2018 Dec;8(6):453-456. doi: 10.1007/s13659-018-0173-y. Epub 2018 Jun 16. PubMed PMID: 29909523; PubMed Central PMCID: PMC6224808. 2: Wu X, He Y, Zhang G, Wu J, Hou Y, Gu Y, Chen H. Royleanone diterpenoid exhibits potent anticancer effects in LNCaP human prostate carcinoma cells by inducing mitochondrial mediated apoptosis, cell cycle arrest, suppression of cell migration and downregulation of mTOR/PI3K/AKT signalling pathway. J BUON. 2018 Jul-Aug;23(4):1055-1060. PubMed PMID: 30358211. 3: Rijo P, Duarte A, Francisco AP, Semedo-Lemsaddek T, Simões MF. In vitro antimicrobial activity of royleanone derivatives against Gram-positive bacterial pathogens. Phytother Res. 2014 Jan;28(1):76-81. doi: 10.1002/ptr.4961. Epub 2013 Mar 11. PubMed PMID: 23494919. 4: Chen L, Ma X, Deng S, Yang X, Song P. Crystal structure of 6,7-de-hydro-royleanone isolated from Taxodium distichum (L.) Rich. Acta Crystallogr E Crystallogr Commun. 2018 Jan 1;74(Pt 1):62-64. doi: 10.1107/S2056989017017935. eCollection 2018 Jan 1. PubMed PMID: 29416893; PubMed Central PMCID: PMC5778487. 5: Xu S, Ma X, Ke R, Deng S, Yang X, Song P. Crystal structure of 7β-hy-droxy-royleanone isolated from Taxodium ascendens (B.). Acta Crystallogr E Crystallogr Commun. 2017 Sep 5;73(Pt 10):1414-1416. doi: 10.1107/S2056989017011987. eCollection 2017 Oct 1. PubMed PMID: 29250348; PubMed Central PMCID: PMC5730285. 6: Ladeiras D, Monteiro CM, Pereira F, Reis CP, Afonso CA, Rijo P. Reactivity of Diterpenoid Quinones: Royleanones. Curr Pharm Des. 2016;22(12):1682-714. Review. PubMed PMID: 26654590. 7: Rijo P, Simões MF, Francisco AP, Rojas R, Gilman RH, Vaisberg AJ, Rodríguez B, Moiteiro C. Antimycobacterial metabolites from Plectranthus: royleanone derivatives against Mycobacterium tuberculosis strains. Chem Biodivers. 2010 Apr;7(4):922-32. doi: 10.1002/cbdv.200900099. PubMed PMID: 20397225. 8: Fun HK, Chantrapromma S, Salae AW, Razak IA, Karalai C. Redetermined structure, inter-molecular inter-actions and absolute configuration of royleanone. Acta Crystallogr Sect E Struct Rep Online. 2011 May 1;67(Pt 5):o1032-3. doi: 10.1107/S1600536811011457. Epub 2011 Apr 7. PubMed PMID: 21754362; PubMed Central PMCID: PMC3089143. 9: Razak IA, Salae AW, Chantrapromma S, Karalai C, Fun HK. Redetermination and absolute configuration of 7α-hy-droxy-royleanone. Acta Crystallogr Sect E Struct Rep Online. 2010 Jun 5;66(Pt 7):o1566-7. doi: 10.1107/S1600536810020544. PubMed PMID: 21587809; PubMed Central PMCID: PMC3006754. 10: Carreño MC, García Ruano JL, Toledo MA. Enantioselective synthesis of (+)-royleanone from sulfinyl quinones. Chemistry. 2000 Jan;6(2):288-91. PubMed PMID: 11931108. 11: Giacomelli E, Bertrand S, Nievergelt A, Zwick V, Simoes-Pires C, Marcourt L, Rivara-Minten E, Cuendet M, Bisio A, Wolfender JL. Cancer chemopreventive diterpenes from Salvia corrugata. Phytochemistry. 2013 Dec;96:257-64. doi: 10.1016/j.phytochem.2013.09.011. Epub 2013 Oct 10. PubMed PMID: 24120298. 12: Gómez-Rivera A, González-Cortazar M, Herrera-Ruíz M, Zamilpa A, Rodríguez-López V. Sessein and isosessein with anti-inflammatory, antibacterial and antioxidant activity isolated from Salvia sessei Benth. J Ethnopharmacol. 2018 May 10;217:212-219. doi: 10.1016/j.jep.2018.02.012. Epub 2018 Feb 16. PubMed PMID: 29458147. 13: Alegre-Gómez S, Sainz P, Simões MF, Rijo P, Moiteiro C, González-Coloma A, Martínez-Díaz RA. Antiparasitic Activity of Diterpenoids Against Trypanosoma cruzi. Planta Med. 2017 Feb;83(3-04):306-311. doi: 10.1055/s-0042-115646. Epub 2016 Sep 6. PubMed PMID: 27599261. 14: Fronza M, Lamy E, Günther S, Heinzmann B, Laufer S, Merfort I. Abietane diterpenes induce cytotoxic effects in human pancreatic cancer cell line MIA PaCa-2 through different modes of action. Phytochemistry. 2012 Jun;78:107-19. doi: 10.1016/j.phytochem.2012.02.015. Epub 2012 Mar 19. PubMed PMID: 22436445. 15: Bernardes CES, Garcia C, Pereira F, Mota J, Pereira P, Cebola MJ, Reis CP, Correia I, Piedade MFM, Minas da Piedade ME, Rijo P. Extraction Optimization and Structural and Thermal Characterization of the Antimicrobial Abietane 7α-Acetoxy-6β-hydroxyroyleanone. Mol Pharm. 2018 Apr 2;15(4):1412-1419. doi: 10.1021/acs.molpharmaceut.7b00892. Epub 2018 Mar 9. PubMed PMID: 29494159. 16: Cerqueira F, Cordeiro-Da-Silva A, Gaspar-Marques C, Simões F, Pinto MM, Nascimento MS. Effect of abietane diterpenes from Plectranthus grandidentatus on T- and B-lymphocyte proliferation. Bioorg Med Chem. 2004 Jan 2;12(1):217-23. PubMed PMID: 14697786. 17: Lin LZ, Wang XM, Huang XL, Huang Y, Yang BJ. Diterpenoids from Salvia prionitis. Planta Med. 1988 Oct;54(5):443-5. PubMed PMID: 17265309. 18: Janicsák G, Zupkó I, Nikolovac MT, Forgo P, Vasas A, Mathé I, Blunden G, Hohmann J. Bioactivity-guided study of antiproliferative activities of Salvia extracts. Nat Prod Commun. 2011 May;6(5):575-9. PubMed PMID: 21615011. 19: Saeidnia S, Ghamarinia M, Gohari AR, Shakeri A. Terpenes From the Root of Salvia hypoleuca Benth. Daru. 2012 Oct 24;20(1):66. doi: 10.1186/2008-2231-20-66. PubMed PMID: 23351362; PubMed Central PMCID: PMC3556016. 20: Liu J, Zapp J, Becker H. Comparative phytochemical investigation of Salvia miltiorrhiza and Salvia triloba. Planta Med. 1995 Oct;61(5):453-5. PubMed PMID: 17238099.