Trichilones A–E: New Limonoids from Trichilia adolfi

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Trichilones A–E: New Limonoids from Trichilia adolfi. / Gonzales-Ramirez, Mariela; Limachi, Ivan; Manner, Sophie; Ticona, Juan C.; Salamanca, Efrain; Gimenez, Alberto ; Sterner, Olov.

In: Molecules, Vol. 26, No. 11, 3070, 21.05.2021.

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Gonzales-Ramirez, Mariela ; Limachi, Ivan ; Manner, Sophie ; Ticona, Juan C. ; Salamanca, Efrain ; Gimenez, Alberto ; Sterner, Olov. / Trichilones A–E: New Limonoids from Trichilia adolfi. In: Molecules. 2021 ; Vol. 26, No. 11.

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TY - JOUR

T1 - Trichilones A–E: New Limonoids from Trichilia adolfi

AU - Gonzales-Ramirez, Mariela

AU - Limachi, Ivan

AU - Manner, Sophie

AU - Ticona, Juan C.

AU - Salamanca, Efrain

AU - Gimenez, Alberto

AU - Sterner, Olov

PY - 2021/5/21

Y1 - 2021/5/21

N2 - 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.

AB - 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.

KW - Trichilia adolfi

KW - Limonoid

KW - Trichilones A-E

KW - Cytotoxicity

KW - Leishmanicidal activity

U2 - 10.3390/molecules26113070

DO - 10.3390/molecules26113070

M3 - Article

C2 - 34063814

VL - 26

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 11

M1 - 3070

ER -