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

Author(s):Show less -

Gimenes, Leila ^{[1, 2]} ; Batista Junior, Joao Marcos ^{[1, 3]} ; dos Santos Junior, Fernando Martins ^{[1, 4]} ; Souza, Matheus da Silva ^[5] ; Luna-Dulcey, Liany ^[6] ; Ellena, Javier Esteves ^[5] ; Cominetti, Marcia Regina ^[6] ; das Gracas Fernandes da Silva, Maria Fatima ^[1] ; Vieira, Paulo Cezar ^{[7, 1]} ; Fernandes, Joao Batista ^[1] ; Staerk, Dan ^[2]

Affiliation

^[1] Fed Univ Sao Carlos UFSCar, Dept Chem, BR-13565905 Sao Carlos, SP - Brazil

^[2] Univ Copenhagen, Dept Drug Design & Pharmacol, DK-2100 Copenhagen - Denmark

^[3] Univ Fed Sao Paulo, Inst Sci & Technol, BR-12231280 Sao Jose Dos Campos, SP - Brazil

^[4] Fluminense Fed Univ UFF, Chem Inst, Dept Organ Chem, Niteroi, RJ - Brazil

^[5] Univ Sao Paulo, Sao Carlos Inst Phys, BR-13566590 Sao Carlos, SP - Brazil

^[6] Univ Fed Sao Carlos, Dept Gerontol, BR-13565905 Sao Carlos, SP - Brazil

^[7] Univ Sao Paulo, Sch Pharmaceut Sci Ribeirao Preto, BR-14040903 Ribeirao Preto, SP - Brazil

• Document type: Journal article
• Source: Phytochemistry; v. 163, p. 38-45, JUL 2019.
• Web of Science Citations: 3

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. (AU)

• FAPESP's process: 13/20458-1 - Control of leaf-cutting ants through biomonitored phytochemical study of Picramnia glazioviana and Picramnia bahiensis - Search of insecticides and fungicides substances and development of nanoencapsulation processes.
• Grantee: Leila Gimenes
• Support Opportunities: Scholarships in Brazil - Doctorate
• FAPESP's process: 15/07089-2 - Vibrational chiroptical spectroscopy for stereochemical characterization of small molecules and macromolecules
• Grantee: João Marcos Batista Junior
• Support Opportunities: Scholarships in Brazil - Young Researchers
• FAPESP's process: 16/18024-1 - Study of Picramnia using hyphenated high-resolution bioassay/HPLC-HRMS-SPE-NMR technology platform
• Grantee: Leila Gimenes
• Support Opportunities: Scholarships abroad - Research Internship - Doctorate
• FAPESP's process: 14/25222-9 - Vibrational chiroptical spectroscopy for stereochemical characterization of small molecules and macromolecules
• Grantee: João Marcos Batista Junior
• Support Opportunities: Research Grants - Young Investigators Grants
• FAPESP's process: 12/25299-6 - Integrated studies for leaf cutting control
• Grantee: João Batista Fernandes
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 16/23794-0 - Stereochemistry of complex natural compounds by vibrational optical activity: acetogenins
• Grantee: Fernando Martins dos Santos Junior
• Support Opportunities: Scholarships in Brazil - Post-Doctoral