Picraviane A and B: Nortriterpenes with limonoid-like skeletons containing a heptanolide E-ring system from Picramnia glazioviana

Leila Gimenes; Joao Marcos Batista Junior; Fernando Martins Dos Santos Junior; Matheus da Silva Souza; Liany Luna-Dulcey; Javier Esteves Ellena; Marcia Regina Cominetti; Maria Fatima das Graças Fernandes da Silva; Paulo Cezar Vieira; Joao Batista Fernandes; Dan Staerk

doi:10.1016/j.phytochem.2019.03.024

Picraviane A and B: Nortriterpenes with limonoid-like skeletons containing a heptanolide E-ring system from Picramnia glazioviana

Phytochemistry. 2019 Jul:163:38-45. doi: 10.1016/j.phytochem.2019.03.024. Epub 2019 Apr 16.

Affiliations

¹ Department of Chemistry, Federal University of Sao Carlos (UFSCar), 13565-905, Sao Carlos, SP, Brazil; Department of Drug Design and Pharmacology, University of Copenhagen, DK-2100, Copenhagen, Denmark.
² Department of Chemistry, Federal University of Sao Carlos (UFSCar), 13565-905, Sao Carlos, SP, Brazil; Institute of Science and Technology, Federal University of Sao Paulo, 12231-280, Sao Jose dos Campos, SP, Brazil.
³ Department of Chemistry, Federal University of Sao Carlos (UFSCar), 13565-905, Sao Carlos, SP, Brazil; Department of Organic Chemistry, Chemistry Institute, Fluminense Federal University (UFF), Niterói, RJ, Brazil.
⁴ São Carlos Institute of Physics, University of São Paulo, 13566-590, São Carlos, SP, Brazil.
⁵ Department of Gerontology, Federal University of Sao Carlos, 13565-905, Sao Carlos, SP, Brazil.
⁶ Department of Chemistry, Federal University of Sao Carlos (UFSCar), 13565-905, Sao Carlos, SP, Brazil.
⁷ Department of Chemistry, Federal University of Sao Carlos (UFSCar), 13565-905, Sao Carlos, SP, Brazil; School of Pharmaceutical Sciences of Ribeirao Preto, University of Sao Paulo, 14040-903, Ribeirao Preto, SP, Brazil.
⁸ Department of Drug Design and Pharmacology, University of Copenhagen, DK-2100, Copenhagen, Denmark. Electronic address: [email protected].

PMID: 31003042
DOI: 10.1016/j.phytochem.2019.03.024

Abstract

Two highly oxygenated nortriterpenes, picraviane A and B, were isolated from the ethanolic extract of Picramnia glazioviana Engl. The structures were determined by analysis of HRMS and 2D NMR spectroscopic data. Single-crystal X-ray diffraction data was also obtained for picraviane B. The absolute configuration of both compounds were assigned by comparison of experimental and calculated vibrational and electronic circular dichroism spectroscopy, respectively. Picraviane A showed a moderate cytotoxic activity against the triple negative MDA-MB-231 breast cancer cell line. These compounds represent an undescribed class of natural products with limonoid-like skeletons containing a heptanolide as the E-ring.

Keywords: Electronic circular dichroism; Nortriterpenes; Picramnia glazioviana Engl. (Picramniaceae); Picravianes A and B; Triple negative breast cancer; Vibrational circular dichroism.

MeSH terms

Antineoplastic Agents, Phytogenic / chemistry
Antineoplastic Agents, Phytogenic / isolation & purification
Antineoplastic Agents, Phytogenic / pharmacology*
Biological Products / chemistry
Biological Products / isolation & purification
Biological Products / pharmacology*
Cell Line, Tumor
Cell Proliferation / drug effects
Cell Survival / drug effects
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Humans
Models, Molecular
Molecular Conformation
Simaroubaceae / chemistry*
Stereoisomerism
Structure-Activity Relationship
Triterpenes / chemistry
Triterpenes / isolation & purification
Triterpenes / pharmacology*

Substances

Antineoplastic Agents, Phytogenic
Biological Products
Triterpenes