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Trichilones A–E: New Limonoids from Trichilia adolfi

Gonzales-Ramirez, Mariela LU ; Limachi, Ivan LU ; Manner, Sophie LU ; Ticona, Juan C. ; Salamanca, Efrain ; Gimenez, Alberto and Sterner, Olov LU (2021) In Molecules 26(11).
Abstract
In addition to the trichilianones A–D recently reported from Trichilia adolfi, a continuing investigation of the chemical constituents of the ethanol extract of the bark of this medicinal plant yielded the five new limonoids 1–5. They are characterized by having four fused rings and are new examples of prieurianin-type limonoids, having a ε-lactone which in 4 and 5 is α, β- unsaturated. The structures of the isolated metabolites were determined by high field NMR spectroscopy and HR mass spectrometry. The new metabolites were shown to have the ε-lactone fused with a tetrahydrofuran ring which is connected to an oxidized hexane ring joined with a cyclo-pentanone having a 3-furanyl substituent. As the crude... (More)
In addition to the trichilianones A–D recently reported from Trichilia adolfi, a continuing investigation of the chemical constituents of the ethanol extract of the bark of this medicinal plant yielded the five new limonoids 1–5. They are characterized by having four fused rings and are new examples of prieurianin-type limonoids, having a ε-lactone which in 4 and 5 is α, β- unsaturated. The structures of the isolated metabolites were determined by high field NMR spectroscopy and HR mass spectrometry. The new metabolites were shown to have the ε-lactone fused with a tetrahydrofuran ring which is connected to an oxidized hexane ring joined with a cyclo-pentanone having a 3-furanyl substituent. As the crude extract possesses antileishmanial activity, the compounds were assayed for cytotoxic and antiparasitic activities in vitro in murine macrophage cells (raw 264.7 cells) and in Leishmania amazoniensis as well as L. braziliensis promastigotes. Metabolites 1–3 and 5 showed moderate cytotoxicity (between 30–94 μg/mL) but are not responsible for the antileishmanial effect of the extract. (Less)
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author
; ; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Trichilia adolfi, Limonoid, Trichilones A-E, Cytotoxicity, Leishmanicidal activity
in
Molecules
volume
26
issue
11
article number
3070
pages
15 pages
publisher
MDPI AG
external identifiers
  • pmid:34063814
  • scopus:85107141640
ISSN
1420-3049
DOI
10.3390/molecules26113070
language
English
LU publication?
yes
id
7a334a24-fc5e-457a-b93c-bce259ce7495
date added to LUP
2021-06-07 09:19:42
date last changed
2022-04-27 02:14:32
@article{7a334a24-fc5e-457a-b93c-bce259ce7495,
  abstract     = {{In addition to the trichilianones A–D recently reported from <i>Trichilia adolfi</i>, a continuing investigation of the chemical constituents of the ethanol extract of the bark of this medicinal plant yielded the five new limonoids <b>1</b>–<b>5</b>. They are characterized by having four fused rings and are new examples of prieurianin-type limonoids, having a ε-lactone which in <b>4</b> and <b>5</b> is α, β- unsaturated. The structures of the isolated metabolites were determined by high field NMR spectroscopy and HR mass spectrometry. The new metabolites were shown to have the ε-lactone fused with a tetrahydrofuran ring which is connected to an oxidized hexane ring joined with a cyclo-pentanone having a 3-furanyl substituent. As the crude extract possesses antileishmanial activity, the compounds were assayed for cytotoxic and antiparasitic activities in vitro in murine macrophage cells (raw 264.7 cells) and in <i>Leishmania amazoniensis</i> as well as <i>L. braziliensis</i> promastigotes. Metabolites <b>1</b>–<b>3</b> and <b>5</b> showed moderate cytotoxicity (between 30–94 μg/mL) but are not responsible for the antileishmanial effect of the extract.}},
  author       = {{Gonzales-Ramirez, Mariela and Limachi, Ivan and Manner, Sophie and Ticona, Juan C. and Salamanca, Efrain and Gimenez, Alberto and Sterner, Olov}},
  issn         = {{1420-3049}},
  keywords     = {{Trichilia adolfi; Limonoid; Trichilones A-E; Cytotoxicity; Leishmanicidal activity}},
  language     = {{eng}},
  month        = {{05}},
  number       = {{11}},
  publisher    = {{MDPI AG}},
  series       = {{Molecules}},
  title        = {{Trichilones A–E: New Limonoids from <i>Trichilia adolfi</i>}},
  url          = {{http://dx.doi.org/10.3390/molecules26113070}},
  doi          = {{10.3390/molecules26113070}},
  volume       = {{26}},
  year         = {{2021}},
}