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

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Trichilianones A-D, Novel Cyclopropane-Type Limonoids from Trichilia adolfi. / Limachi, Ivan; Gonzalez-Ramirez, Mariela; Manner, Sophie; Ticona, Juan C.; Salamanca, Efrain; Gimenez, Alberto; Sterner, Olov.

In: Molecules (Basel, Switzerland), Vol. 26, No. 4, 1019, 2021.

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TY - JOUR

T1 - Trichilianones A-D, Novel Cyclopropane-Type Limonoids from Trichilia adolfi

AU - Limachi, Ivan

AU - Gonzalez-Ramirez, Mariela

AU - Manner, Sophie

AU - Ticona, Juan C.

AU - Salamanca, Efrain

AU - Gimenez, Alberto

AU - Sterner, Olov

PY - 2021

Y1 - 2021

N2 - 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.

AB - 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.

KW - cyclopropane-limonoids

KW - cytotoxicity

KW - leishmanicidal activity

KW - Trichilia adolfi

U2 - 10.3390/molecules26041019

DO - 10.3390/molecules26041019

M3 - Article

C2 - 33671969

AN - SCOPUS:85102605724

VL - 26

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 4

M1 - 1019

ER -