Rohitukine | CAS#71294-60-5 | anti-cancer agent

MedKoo Cat#: 561338 | Name: Rohitukine

Description:

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

Rohitukine is an anti-cancer agent. It acts through gastrin antagonism and H(+) K (+)-ATPase inhibition to modulate apoptosis pathways. Rohitukine ia an antidyslipidemic, antiadipogenic, gastroprotective, antifertility, and antileishmanial compound.

Chemical Structure

Rohitukine

CAS#71294-60-5

Theoretical Analysis

MedKoo Cat#: 561338

Name: Rohitukine

CAS#: 71294-60-5

Chemical Formula: C16H19NO5

Exact Mass: 305.1263

Molecular Weight: 305.33

Elemental Analysis: C, 62.94; H, 6.27; N, 4.59; O, 26.20

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

Rohitukine; NSC623611; NSC-623611; NSC 623611;

IUPAC/Chemical Name

5,7-Dihydroxy-8-[(3R,4S)-3-hydroxy-1-methylpiperidin-4-yl]-2-methylchromen-4-one

InChi Key

MOCVYVBNJQIVOV-RNCFNFMXSA-N

InChi Code

InChI=1S/C16H19NO5/c1-8-5-10(18)15-12(20)6-11(19)14(16(15)22-8)9-3-4-17(2)7-13(9)21/h5-6,9,13,19-21H,3-4,7H2,1-2H3/t9-,13+/m1/s1

SMILES Code

O=C1C=C(C)OC2=C1C(O)=CC(O)=C2[C@H]3[C@@H](O)CN(C)CC3

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

Preparing Stock Solutions

The following data is based on the product molecular weight 305.33 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: Amin SA, Bhattacharya P, Basak S, Gayen S, Nandy A, Saha A. Pharmacoinformatics study of Piperolactam A from Piper betle root as new lead for non steroidal anti fertility drug development. Comput Biol Chem. 2017 Apr;67:213-224. doi: 10.1016/j.compbiolchem.2017.01.004. Epub 2017 Jan 11. PubMed PMID: 28160639. 2: Isah T. Anticancer Alkaloids from Trees: Development into Drugs. Pharmacogn Rev. 2016 Jul-Dec;10(20):90-99. doi: 10.4103/0973-7847.194047. Review. PubMed PMID: 28082790; PubMed Central PMCID: PMC5214563. 3: Kumar V, Bharate SS, Vishwakarma RA. Modulating lipophilicity of rohitukine via prodrug approach: Preparation, characterization, and in vitro enzymatic hydrolysis in biorelevant media. Eur J Pharm Sci. 2016 Sep 20;92:203-11. doi: 10.1016/j.ejps.2016.07.010. Epub 2016 Jul 12. PubMed PMID: 27422078. 4: Kumar V, Guru SK, Jain SK, Joshi P, Gandhi SG, Bharate SB, Bhushan S, Bharate SS, Vishwakarma RA. A chromatography-free isolation of rohitukine from leaves of Dysoxylum binectariferum: Evaluation for in vitro cytotoxicity, Cdk inhibition and physicochemical properties. Bioorg Med Chem Lett. 2016 Aug 1;26(15):3457-63. doi: 10.1016/j.bmcl.2016.06.046. Epub 2016 Jun 16. PubMed PMID: 27363938. 5: Mohana Kumara P, Srimany A, Arunan S, Ravikanth G, Uma Shaanker R, Pradeep T. Desorption Electrospray Ionization (DESI) Mass Spectrometric Imaging of the Distribution of Rohitukine in the Seedling of Dysoxylum binectariferum Hook. F. PLoS One. 2016 Jun 30;11(6):e0158099. doi: 10.1371/journal.pone.0158099. eCollection 2016. PubMed PMID: 27362422; PubMed Central PMCID: PMC4928942. 6: Ray B, Agarwal S, Lohani N, Rajeswari MR, Mehrotra R. Structural, conformational and thermodynamic aspects of groove-directed-intercalation of flavopiridol into DNA. J Biomol Struct Dyn. 2016 Nov;34(11):2518-35. doi: 10.1080/07391102.2015.1118708. Epub 2016 Feb 17. PubMed PMID: 26599132. 7: Safia, Kamil M, Jadiya P, Sheikh S, Haque E, Nazir A, Lakshmi V, Mir SS. The Chromone Alkaloid, Rohitukine, Affords Anti-Cancer Activity via Modulating Apoptosis Pathways in A549 Cell Line and Yeast Mitogen Activated Protein Kinase (MAPK) Pathway. PLoS One. 2015 Sep 25;10(9):e0137991. doi: 10.1371/journal.pone.0137991. eCollection 2015. PubMed PMID: 26405812; PubMed Central PMCID: PMC4583253. 8: Mohana Kumara P, Srimany A, Ravikanth G, Uma Shaanker R, Pradeep T. Ambient ionization mass spectrometry imaging of rohitukine, a chromone anti-cancer alkaloid, during seed development in Dysoxylum binectariferum Hook.f (Meliaceae). Phytochemistry. 2015 Aug;116:104-10. doi: 10.1016/j.phytochem.2015.02.031. Epub 2015 Mar 20. PubMed PMID: 25799183. 9: Mahajan V, Sharma N, Kumar S, Bhardwaj V, Ali A, Khajuria RK, Bedi YS, Vishwakarma RA, Gandhi SG. Production of rohitukine in leaves and seeds of Dysoxylum binectariferum: an alternate renewable resource. Pharm Biol. 2015 Mar;53(3):446-50. doi: 10.3109/13880209.2014.923006. Epub 2014 Dec 4. PubMed PMID: 25472605. 10: Chhonker YS, Chandasana H, Kumar A, Kumar D, Laxman TS, Mishra SK, Balaramnavar VM, Srivastava S, Saxena AK, Bhatta RS. Pharmacokinetics, Tissue Distribution and Plasma Protein Binding Studies of Rohitukine: A Potent Anti-hyperlipidemic Agent. Drug Res (Stuttg). 2015 Jul;65(7):380-7. doi: 10.1055/s-0034-1387774. Epub 2014 Sep 22. PubMed PMID: 25243649. 11: Jain SK, Meena S, Gupta AP, Kushwaha M, Uma Shaanker R, Jaglan S, Bharate SB, Vishwakarma RA. Dysoxylum binectariferum bark as a new source of anticancer drug camptothecin: bioactivity-guided isolation and LCMS-based quantification. Bioorg Med Chem Lett. 2014 Jul 15;24(14):3146-9. doi: 10.1016/j.bmcl.2014.05.001. Epub 2014 May 10. PubMed PMID: 24878199. 12: Chhonker YS, Chandasana H, Kumar D, Mishra SK, Srivastava S, Balaramnavar VM, Gaikwad AN, Kanojiya S, Saxena AK, Bhatta RS. Pharmacokinetic and metabolism studies of rohitukine in rats by high performance liquid-chromatography with tandem mass spectrometry. Fitoterapia. 2014 Sep;97:34-42. doi: 10.1016/j.fitote.2014.05.004. Epub 2014 May 16. PubMed PMID: 24840406. 13: Mishra SK, Tiwari S, Shrivastava S, Sonkar R, Mishra V, Nigam SK, Saxena AK, Bhatia G, Mir SS. Pharmacological evaluation of the efficacy of Dysoxylum binectariferum stem bark and its active constituent rohitukine in regulation of dyslipidemia in rats. J Nat Med. 2014 Mar 28. [Epub ahead of print] PubMed PMID: 24677095. 14: Varshney S, Shankar K, Beg M, Balaramnavar VM, Mishra SK, Jagdale P, Srivastava S, Chhonker YS, Lakshmi V, Chaudhari BP, Bhatta RS, Saxena AK, Gaikwad AN. Rohitukine inhibits in vitro adipogenesis arresting mitotic clonal expansion and improves dyslipidemia in vivo. J Lipid Res. 2014 Jun;55(6):1019-32. doi: 10.1194/jlr.M039925. Epub 2014 Mar 19. PubMed PMID: 24646949; PubMed Central PMCID: PMC4031934. 15: Kumara PM, Soujanya KN, Ravikanth G, Vasudeva R, Ganeshaiah KN, Shaanker RU. Rohitukine, a chromone alkaloid and a precursor of flavopiridol, is produced by endophytic fungi isolated from Dysoxylum binectariferum Hook.f and Amoora rohituka (Roxb).Wight & Arn. Phytomedicine. 2014 Mar 15;21(4):541-6. doi: 10.1016/j.phymed.2013.09.019. Epub 2013 Nov 9. PubMed PMID: 24215673. 16: Jain SK, Bharate SB, Vishwakarma RA. Cyclin-dependent kinase inhibition by flavoalkaloids. Mini Rev Med Chem. 2012 Jun;12(7):632-49. Review. PubMed PMID: 22512551. 17: Singh N, Singh P, Shrivastva S, Mishra SK, Lakshmi V, Sharma R, Palit G. Gastroprotective effect of anti-cancer compound rohitukine: possible role of gastrin antagonism and H(+) K (+)-ATPase inhibition. Naunyn Schmiedebergs Arch Pharmacol. 2012 Mar;385(3):277-86. doi: 10.1007/s00210-011-0711-1. Epub 2011 Nov 24. PubMed PMID: 22113419. 18: Mohana Kumara P, Zuehlke S, Priti V, Ramesha BT, Shweta S, Ravikanth G, Vasudeva R, Santhoshkumar TR, Spiteller M, Uma Shaanker R. Fusarium proliferatum, an endophytic fungus from Dysoxylum binectariferum Hook.f, produces rohitukine, a chromane alkaloid possessing anti-cancer activity. Antonie Van Leeuwenhoek. 2012 Feb;101(2):323-9. doi: 10.1007/s10482-011-9638-2. Epub 2011 Sep 4. PubMed PMID: 21898150. 19: Ismail IS, Nagakura Y, Hirasawa Y, Hosoya T, Lazim MI, Lajis NH, Shiro M, Morita H. Chrotacumines A-D, chromone alkaloids from Dysoxylum acutangulum. J Nat Prod. 2009 Oct;72(10):1879-83. doi: 10.1021/np9003849. PubMed PMID: 19757855. 20: Mohanakumara P, Sreejayan N, Priti V, Ramesha BT, Ravikanth G, Ganeshaiah KN, Vasudeva R, Mohan J, Santhoshkumar TR, Mishra PD, Ram V, Shaanker RU. Dysoxylum binectariferum Hook.f (Meliaceae), a rich source of rohitukine. Fitoterapia. 2010 Mar;81(2):145-8. doi: 10.1016/j.fitote.2009.08.010. Epub 2009 Aug 15. PubMed PMID: 19686817.