2. Academic Validation
  3. Total synthesis of Calebin-A, preparation of its analogues, and their neuronal cell protectivity against beta-amyloid insult

Total synthesis of Calebin-A, preparation of its analogues, and their neuronal cell protectivity against beta-amyloid insult

  • Bioorg Med Chem Lett. 2001 Sep 17;11(18):2541-3. doi: 10.1016/s0960-894x(01)00489-9.
D S Kim 1,  J Y Kim
Affiliations

Affiliation

  • 1 The Program for Collaborative Research in Pharmaceutical Science and the Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 South Wood Street, Chicago, IL 60612, USA. [email protected]
PMID: 11549465 DOI: 10.1016/s0960-894x(01)00489-9
Abstract

A total synthesis of Calebin-A (1), a novel curcuminoid isolated from turmeric (Curcuma longa, Zingiberaceae) that has been demonstrated to protect neuronal cells from beta-amyloid insult, was successfully achieved in four steps. Elaborating on this synthetic route, 13 analogues were prepared for a structure-activity relationship (SAR) study. It was found that the parent compound 1 and derivatives 21, 28, and 30 protect PC12 rat pheocromocytoma and IMR-32 human neuroblastoma cells from beta-amyloid(25-35) insult. These results suggest that hydroxy group at para-position is most critical for the expression of biological activity.

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