Computationally aided stereochemical assignment of undescribed bisabolenes from Calea urticifolia

Vedanjali Gogineni; Manal A Nael; Francisco León; Marvin J Núñez; Stephen J Cutler

doi:10.1016/j.phytochem.2018.10.022

Computationally aided stereochemical assignment of undescribed bisabolenes from Calea urticifolia

Phytochemistry. 2019 Jan:157:145-150. doi: 10.1016/j.phytochem.2018.10.022. Epub 2018 Nov 3.

Authors

Vedanjali Gogineni¹, Manal A Nael², Francisco León³, Marvin J Núñez⁴, Stephen J Cutler⁵

Affiliations

¹ Department of BioMolecular Sciences, School of Pharmacy, University of Mississippi, University, MS, 38677, USA.
² Department of Pharmaceutical Chemistry, Tanta University, Tanta, 31527, Egypt.
³ Department of BioMolecular Sciences, School of Pharmacy, University of Mississippi, University, MS, 38677, USA; Department of Medicinal Chemistry, College of Pharmacy, University of Florida, Gainesville, FL, 32610, USA. Electronic address: jleonoyola@cop.ufl.edu.
⁴ Laboratorio de Investigación en Productos Naturales, Facultad de Química y Farmacia, University of El Salvador, Av. Héroes y Mártires del 30 de Julio, San Salvador, El Salvador.
⁵ Department of BioMolecular Sciences, School of Pharmacy, University of Mississippi, University, MS, 38677, USA; College of Pharmacy, University of South Carolina, Columbia, SC, 29208, USA. Electronic address: sjcutler@cop.sc.edu.

PMID: 30399497
DOI: 10.1016/j.phytochem.2018.10.022

Abstract

Calea urticifolia (Mill.) DC. (Compositae) is a medicinal plant found in El Salvador. Calea is used in folkloric medicine as a psychoactive principle with calming effect, as well as in the treatment of diarrhea and fever. Three undescribed bisabolenes, named caleanolenes A-C, as well as, three known sesquiterpene lactones 2,3-epoxyjuanislamin, calealactone B, calein C, and the flavonoid acacetin, were isolated from the chloroform extract of the leaves of C. urticifolia. The chemical structures of the isolated compounds were determined on the basis of HRMS, IR, CD, and from 1D and 2D NMR spectroscopic studies. The absolute configurations of the caleanolenes have been partly established using GIAO NMR and ECD calculations. The isolated compounds were evaluated for cytotoxicity against the CA46 and Raji lymphoma, and the MCF7 breast cancer cell lines, with 2,3-epoxyjuanislamin showing the best activity in all cell lines (IC₅₀ value range 2.9-12.3 μM).

Keywords: Bisabolenes; Calea urticifolia; Compositae; Cytotoxicity; Sesquiterpenes.

MeSH terms

Antineoplastic Agents, Phytogenic / chemistry*
Antineoplastic Agents, Phytogenic / pharmacology*
Asteraceae / chemistry*
Density Functional Theory
Humans
MCF-7 Cells
Models, Molecular
Molecular Conformation
Sesquiterpenes / chemistry*
Sesquiterpenes / pharmacology*
Stereoisomerism

Substances

Antineoplastic Agents, Phytogenic
Sesquiterpenes

Grants and funding

P20 GM104932/GM/NIGMS NIH HHS/United States