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Keywords = α,β-unsaturated ε-lactone

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11 pages, 2709 KiB  
Article
Cembranolides and Related Constituents from the Soft Coral Sarcophyton cinereum
by Chih-Hua Chao, Yi-Ju Chen, Chiung-Yao Huang, Fang-Rong Chang, Chang-Feng Dai and Jyh-Horng Sheu
Molecules 2022, 27(6), 1760; https://doi.org/10.3390/molecules27061760 - 8 Mar 2022
Cited by 6 | Viewed by 2430
Abstract
In an attempt to explore the bioactive metabolites of the soft coral Sarcophyton cinereum, three new cembranolides, cinerenolides A–C (1–3), and 16 known compounds were isolated and identified from the EtOAc extract. The structures of the new cembranolides [...] Read more.
In an attempt to explore the bioactive metabolites of the soft coral Sarcophyton cinereum, three new cembranolides, cinerenolides A–C (1–3), and 16 known compounds were isolated and identified from the EtOAc extract. The structures of the new cembranolides were elucidated on the basis of spectroscopic analysis, and the NOE analysis of cinerenolide A (1) was performed with the assistance of the calculated lowest-energy molecular model. The relative configuration of cinerenolide C (3) was determined by the quantum chemical NMR calculation, followed by applying DP4+ analysis. In addition, the cytotoxic assays disclosed that some compounds exhibited moderate to potent activities in the proliferation of P388, DLD-1, HuCCT-1, and CCD966SK cell lines. Full article
(This article belongs to the Special Issue Innovative Marine Molecules: Chemistry, Biology and Analysis)
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15 pages, 1059 KiB  
Article
Trichilones A–E: New Limonoids from Trichilia adolfi
by Mariela Gonzalez-Ramirez, Ivan Limachi, Sophie Manner, Juan C. Ticona, Efrain Salamanca, Alberto Gimenez and Olov Sterner
Molecules 2021, 26(11), 3070; https://doi.org/10.3390/molecules26113070 - 21 May 2021
Cited by 7 | Viewed by 2512
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 [...] Read 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. Full article
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13 pages, 1003 KiB  
Article
Trichilianones A-D, Novel Cyclopropane-Type Limonoids from Trichilia adolfi
by Ivan Limachi, Mariela Gonzalez-Ramirez, Sophie Manner, Juan C. Ticona, Efrain Salamanca, Alberto Gimenez and Olov Sterner
Molecules 2021, 26(4), 1019; https://doi.org/10.3390/molecules26041019 - 15 Feb 2021
Cited by 7 | Viewed by 2306
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 [...] Read 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. Full article
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