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 Ellena; Marcia Regina Cominetti; Maria Fatima das Graças Fernandes da Silva; Paulo Cezar Vieira; Joao Bastita Fernandes; Dan Stærk

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

Leila Gimenes, Joao Marcos Batista Junior, Fernando Martins dos Santos Junior, Matheus da Silva Souza, Liany Luna-Dulcey, Javier Ellena, Marcia Regina Cominetti, Maria Fatima das Graças Fernandes da Silva, Paulo Cezar Vieira, Joao Bastita Fernandes, Dan Stærk

4 Citations (Scopus)

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.

Original language	English
Journal	Phytochemistry
Volume	163
Pages (from-to)	38-45
ISSN	0031-9422
DOIs	https://doi.org/10.1016/j.phytochem.2019.03.024
Publication status	Published - Jul 2019

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Gimenes, L., Batista Junior, J. M., dos Santos Junior, F. M., Souza, M. D. S., Luna-Dulcey, L., Ellena, J., Cominetti, M. R., da Silva, M. F. D. G. F., Vieira, P. C., Fernandes, J. B., & Stærk, D. (2019). Picraviane A and B: Nortriterpenes with limonoid-like skeletons containing a heptanolide E-ring system from Picramnia glazioviana . Phytochemistry, 163, 38-45. https://doi.org/10.1016/j.phytochem.2019.03.024

Gimenes, L, Batista Junior, JM, dos Santos Junior, FM, Souza, MDS, Luna-Dulcey, L, Ellena, J, Cominetti, MR, da Silva, MFDGF, Vieira, PC, Fernandes, JB & Stærk, D 2019, 'Picraviane A and B: Nortriterpenes with limonoid-like skeletons containing a heptanolide E-ring system from Picramnia glazioviana ', Phytochemistry, vol. 163, pp. 38-45. https://doi.org/10.1016/j.phytochem.2019.03.024

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

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.",

author = "Leila Gimenes and {Batista Junior}, {Joao Marcos} and {dos Santos Junior}, {Fernando Martins} and Souza, {Matheus da Silva} and Liany Luna-Dulcey and Javier Ellena and Cominetti, {Marcia Regina} and {da Silva}, {Maria Fatima das Gra{\c c}as Fernandes} and Vieira, {Paulo Cezar} and Fernandes, {Joao Bastita} and Dan St{\ae}rk",

year = "2019",

month = jul,

doi = "10.1016/j.phytochem.2019.03.024",

language = "English",

volume = "163",

pages = "38--45",

journal = "Phytochemistry",

issn = "0031-9422",

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T1 - Picraviane A and B: Nortriterpenes with limonoid-like skeletons containing a heptanolide E-ring system from Picramnia glazioviana

AU - Gimenes, Leila

AU - Batista Junior, Joao Marcos

AU - dos Santos Junior, Fernando Martins

AU - Souza, Matheus da Silva

AU - Luna-Dulcey, Liany

AU - Ellena, Javier

AU - Cominetti, Marcia Regina

AU - da Silva, Maria Fatima das Graças Fernandes

AU - Vieira, Paulo Cezar

AU - Fernandes, Joao Bastita

AU - Stærk, Dan

PY - 2019/7

Y1 - 2019/7

N2 - 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.

AB - 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.

U2 - 10.1016/j.phytochem.2019.03.024

DO - 10.1016/j.phytochem.2019.03.024

M3 - Journal article

C2 - 31003042

SN - 0031-9422

VL - 163

SP - 38

EP - 45

JO - Phytochemistry

JF - Phytochemistry

ER -

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

Abstract

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