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Trichilianones A-D, Novel Cyclopropane-Type Limonoids from Trichilia adolfi

Limachi, Ivan LU ; Gonzalez-Ramirez, Mariela LU ; Manner, Sophie LU ; Ticona, Juan C. ; Salamanca, Efrain ; Gimenez, Alberto and Sterner, Olov LU (2021) In Molecules (Basel, Switzerland) 26(4).
Abstract

The fractionation of an ethanol extract of the bark of Trichilia adolfi yielded four novel limonoids (trichilinones A-D, 1-4), with five fused rings and related to the hortiolide-type limonoids. Starting with an ε-lactone, which is α,β-unsaturated in trichilinones A and D (1 and 4), attached to a tetrahydrofuran ring that is connected to an unusual bicyclo [5.1.0] hexane system, joined with a cyclopentanone with a 3-furanyl substituent [(2-oxo)-furan-(5H)-3-yl in trichilinone D (4)], the four compounds isolated display a new 7/5/3/5/5 limonoid ring system. Their structures were established based on extensive analysis of NMR spectroscopic data. As the crude extract possessed anti-leishmanial properties, the compounds were assayed for... (More)

The fractionation of an ethanol extract of the bark of Trichilia adolfi yielded four novel limonoids (trichilinones A-D, 1-4), with five fused rings and related to the hortiolide-type limonoids. Starting with an ε-lactone, which is α,β-unsaturated in trichilinones A and D (1 and 4), attached to a tetrahydrofuran ring that is connected to an unusual bicyclo [5.1.0] hexane system, joined with a cyclopentanone with a 3-furanyl substituent [(2-oxo)-furan-(5H)-3-yl in trichilinone D (4)], the four compounds isolated display a new 7/5/3/5/5 limonoid ring system. Their structures were established based on extensive analysis of NMR spectroscopic data. As the crude extract possessed anti-leishmanial properties, the compounds were assayed for cytotoxic and anti-parasitic activities in vitro in murine macrophages cells (Raw 264.7) and leishmania promastigotes (L. amazoniensis and L. braziliensis), respectively. The compounds showed moderate cytotoxicity (approximately 70 μg/mL), but are not responsible for the leishmanicidal effect of the extract.

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author
; ; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
cyclopropane-limonoids, cytotoxicity, leishmanicidal activity, Trichilia adolfi
in
Molecules (Basel, Switzerland)
volume
26
issue
4
article number
1019
publisher
MDPI AG
external identifiers
  • pmid:33671969
  • scopus:85102605724
ISSN
1420-3049
DOI
10.3390/molecules26041019
language
English
LU publication?
yes
id
c927e6ba-5e72-4915-a436-ae75972a34bf
date added to LUP
2021-03-26 10:27:14
date last changed
2025-03-09 10:09:14
@article{c927e6ba-5e72-4915-a436-ae75972a34bf,
  abstract     = {{<p>The fractionation of an ethanol extract of the bark of Trichilia adolfi yielded four novel limonoids (trichilinones A-D, 1-4), with five fused rings and related to the hortiolide-type limonoids. Starting with an ε-lactone, which is α,β-unsaturated in trichilinones A and D (1 and 4), attached to a tetrahydrofuran ring that is connected to an unusual bicyclo [5.1.0] hexane system, joined with a cyclopentanone with a 3-furanyl substituent [(2-oxo)-furan-(5H)-3-yl in trichilinone D (4)], the four compounds isolated display a new 7/5/3/5/5 limonoid ring system. Their structures were established based on extensive analysis of NMR spectroscopic data. As the crude extract possessed anti-leishmanial properties, the compounds were assayed for cytotoxic and anti-parasitic activities in vitro in murine macrophages cells (Raw 264.7) and leishmania promastigotes (L. amazoniensis and L. braziliensis), respectively. The compounds showed moderate cytotoxicity (approximately 70 μg/mL), but are not responsible for the leishmanicidal effect of the extract.</p>}},
  author       = {{Limachi, Ivan and Gonzalez-Ramirez, Mariela and Manner, Sophie and Ticona, Juan C. and Salamanca, Efrain and Gimenez, Alberto and Sterner, Olov}},
  issn         = {{1420-3049}},
  keywords     = {{cyclopropane-limonoids; cytotoxicity; leishmanicidal activity; Trichilia adolfi}},
  language     = {{eng}},
  number       = {{4}},
  publisher    = {{MDPI AG}},
  series       = {{Molecules (Basel, Switzerland)}},
  title        = {{Trichilianones A-D, Novel Cyclopropane-Type Limonoids from Trichilia adolfi}},
  url          = {{http://dx.doi.org/10.3390/molecules26041019}},
  doi          = {{10.3390/molecules26041019}},
  volume       = {{26}},
  year         = {{2021}},
}