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Absolute Configuration of Dihydro-β-agarofuran Sesquiterpenes from Maytenus jelskii and Their Potential Antitumor-Promoting Effects. | LitMetric

Absolute Configuration of Dihydro-β-agarofuran Sesquiterpenes from Maytenus jelskii and Their Potential Antitumor-Promoting Effects.

J Nat Prod

Instituto Universitario de Bio-Orgánica Antonio González, Departamento de Química Orgánica, and Instituto Canario de Investigación del Cáncer, Universidad de La Laguna , Avenida Astrofísico Francisco Sánchez 2, 38206 La Laguna, Tenerife, Spain.

Published: September 2016

AI Article Synopsis

  • Chemoprevention shows potential for cancer control, especially during early stages of cancer development, through the use of specific agents.
  • The study focused on isolating and testing 10 new and 3 known sesquiterpenes from Maytenus jelskii, using advanced techniques to determine their structures.
  • Six of the tested compounds demonstrated better antitumor activity compared to the standard β-carotene, with compound 5 showing promising effects at low concentrations, suggesting certain chemical groups enhance effectiveness.

Article Abstract

Chemoprevention of human cancer appears to be a feasible strategy for cancer control, especially when chemopreventive intervention is involved during early stages of the carcinogenesis process. As a part of our ongoing research program into new chemopreventive agents, herein are reported the isolation, structural elucidation, and biological evaluation of 10 new (1-10) and three known (11-13) sesquiterpenes with a dihydro-β-agarofuran skeleton from the leaves of Maytenus jelskii Zahlbr. Their stereostructures have been elucidated by means of spectroscopic analysis, including 1D and 2D NMR techniques, ECD studies, and biogenetic considerations. The isolated metabolites and eight previously reported sesquiterpenes (14-21) were screened for their antitumor-promoting activity using a short-term in vitro assay for Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). Six compounds from this series (4, 5, 11, and 13-15) were found to exhibit higher efficacies than β-carotene, used as reference inhibitor for EBV-EA activation. In particular, promising antitumor activity was observed for compound 5, exhibiting inhibition even at the lowest concentration assayed (10 mol ratio/TPA). Preliminary structure-activity relationship analysis revealed that the acetate, benzoate, and hydroxy groups are the most desirable substituents on the sesquiterpene scaffold for activity in the EBV-EA activation assay.

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Source
http://dx.doi.org/10.1021/acs.jnatprod.6b00469DOI Listing

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