CC BY ND NC 4.0 · SynOpen 2017; 01(01): 0125-0128
DOI: 10.1055/s-0036-1591507
paper
Copyright with the author

An Expeditious, Green and Protecting-Group-Free Synthesis of a Potent Secondary Metabolite Calebin-A and Its Analogues

Anju Majeed
Sami Labs Ltd., 19/1 & 19/2, I Main, II Phase, Peenya Industrial Area, Bangalore-560058, India
,
Sabinsa Corporation, 20 Lake Drive, East Windsor, NJ 08520, USA   Email: kalyanam@sabinsa.com
,
Muhammed Majeed
Sami Labs Ltd., 19/1 & 19/2, I Main, II Phase, Peenya Industrial Area, Bangalore-560058, India
Sabinsa Corporation, 20 Lake Drive, East Windsor, NJ 08520, USA   Email: kalyanam@sabinsa.com
,
Samuel Manoharan Thomas
Sami Labs Ltd., 19/1 & 19/2, I Main, II Phase, Peenya Industrial Area, Bangalore-560058, India
,
Nooruddin Thajuddin
Department of Microbiology, Faculty of Science, Engineering & Technology, Bharathidasan University, Thiruchirapalli-620024, Tamil Nadu, India
› Author Affiliations
Further Information

Publication History

Received: 18 August 2017

Accepted after revision: 04 October 2017

Publication Date:
20 October 2017 (online)

Abstract

The synthesis of Calebin-A (10a) and analogues (10bd), which are minor but pharmacologically active components (<0.01% of the oleoresin) of curcuma longa, is described. This flexible synthesis is achieved under near neutral conditions in water/solvent biphasic medium at room temperature without involving any protecting groups.

 
  • References

  • 1 Kumar A. Chetia H. Sharma S. Kabiraj D. Talukdar NC. Bora U. Database (Oxford). 2015: 1-6, DOI: DOI: 10.1093/database/bav070 http://www.crdb.in
    • 2a Li S. Yuan W. Deng G. Wang P. Yang P. Aggarwal BB. Pharm. Crops 2011; 2: 28
    • 2b Aggarwal BB. Yuan W. Li S. Gupta SC. Mol. Nutr. Food Res. 2013; 57: 1529
  • 3 Park SY. Kim DS. H. L. J. Nat. Prod. 2002; 65: 1227
    • 4a Li N.-G. Shi Z.-H. Tang Y.-P. Li B.-Q. Duan J.-A. Molecules 2009; 14: 2118
    • 4b Ferulate esters are important components of rice bran oil, see: Bao Y. Yanase E. Nakatsuka S. Biosci., Biotechnol., Biochem. 2013; 77: 877
  • 5 Zeng YC. Qiu F. Takahashi K. Liang JM. Qu GX. Yao XS. Chem. Pharm. Bull. 2007; 55: 940
  • 6 Kim DS. H. L. Kim JY. Bioorg. Med. Chem. Lett. 2001; 11: 2541
  • 7 Li Y. Li S. Han Y. Liu J. Zhang JL. F. Wang Y. Liu X. Yao L. Eur. J. Pharmacol. 2008; 591: 252
  • 8 Liou WS. Lin C. Lee PS. Kalyanam N. Ho CT. Pan MH. J. Funct. Foods 2016; 26: 781
  • 9 Chen L. Li S. Liu C. Guo H. Li Y. Disi Junyi Daxue Xuebao 2009; 30: 7
  • 10 Majeed M. Kalyanam N. Anju M. Bani S. Anjali P. US 20140249219 A1 20140904, 2014
  • 11 Kalyanam N. Majeed A. Majeed M. US 20160199340 A1 20160714, 2014
  • 12 Kalyanam N. Majeed A. Majeed M. Jpn. Kokai Tokkyo Koho JP 2015214542 A 20151203, 2015
  • 13 Majeed M. Pandey A. US 20130012579 A1 20130110, 2013
  • 14 Lai CS. Liao SN. Tsai ML. Kalyanam N. Majeed M. Majeed A. Ho CT. Pan MH. Mol. Nutr. Food Res. 2015; 59: 1883
  • 15 Majeed M. Kalyanam N. Bani S. Pandey A. EP 2893926 A1 20150715, 2015
  • 16 Kalyanam N. Majeed A. Bani S. Pandey A. Majeed M. NZ 624269 A 20141224, 2014
  • 17 Majeed M. Kalyanam N. Natarajan S. Bani S. Pandey A. Karri SK. Toxicol. Rep. 2015; 2: 580
  • 18 Tyagi AK. Prasad S. Majeed M. Aggarwal BB. Arch. Biochem. Biophys. 2016; 593: 80
  • 19 Oliveira AL. P. Martinez SE. Nagabushnam K. Majeed M. Alrushaid S. Sayre CL. Davies NM. J. Pharm. Pharm. Sci. 2015; 18: 494
  • 20 Schneider C. Gordon ON. Edwards RL. Luis PB. J. Agric. Food Chem. 2015; 63: 7606
  • 21 Wang Z. Yin G. Qin J. Gao M. Cao L. Wu A. Synthesis 2008; 3675
  • 22 Majeed M. Kalyanam N. Majeed A. Manoharan TS. US 7,253,324, 2007 EP 2963007 A1 20160106, 2016 Korean Pat. 10-1629561