Isolation, semi-synthesis and bio-evaluation of spatane derivatives from the brown algae Stoechospermum marginatum

  • Bioorg Med Chem Lett. 2015 Jun 15;25(12):2479-83. doi: 10.1016/j.bmcl.2015.04.061.
B Chinnababu  1 ,  S Purushotham Reddy  1 ,  P Sankara Rao  1 ,  V Loka Reddy  2 ,  B Sudheer Kumar  3 ,  J Venkateswara Rao  2 ,  R S Prakasham  3 ,  K Suresh Babu  4
Affiliations
  • 1. Division of Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 607, India.
  • 2. Biology and Biotechnology Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 607, India.
  • 3. BEEC Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 607, India.
  • 4. Division of Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 607, India. Electronic address: [email protected].
PMID: 25978960 DOI: 10.1016/j.bmcl.2015.04.061
Abstract

A comprehensive investigation of chemical constituents from brown algae Stoechospermum marginatum yielded ten known spatane compounds (1-10). To develop the compound libraries on these scaffolds, a series of semi synthetic derivatives was prepared (1a-1d, 2a, 4a, 11 and 12) and investigated for their anti-microbial and Anticancer activities. The results indicated that compounds 2a, 4, 1b and 4a exhibited potent cytotoxic activities against B16F10 Cancer cell line with IC50 values of 3.28, 3.45, 3.62 and 4.11 μg/ml respectively, which are comparable to the standard drug (etoposide IC50=4.12 μg/ml). In addition, 4 and 1b were also manifested potent antimicrobial activities against tested Bacterial and Fungal strains. This is the first Letter on the synthesis and biological activities of these novel derivatives.

Keywords
Anti-cancer activity; Anti-microbial activity; Brownseaweed; Dictyotaceae; Semi-synthesis; Spatane diterpenoids; Stochospermum marginatum.