Trichilones A–E: New Limonoids from Trichilia adolfi (original) (raw)
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Trichilianones A-D, Novel Cyclopropane-Type Limonoids from Trichilia adolfi
Molecules, 2021
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 re...
Natural Product Research
One new limonoid, trigilgianin (1), one new phenyl alkene, epoxy gilgialkene (2), together with five known compounds: scopoletin (3), sitosteryl-6'-O-undecanoate-β-Dglucoside (4), sitosteryl-O-β-D-glucopyranoside (5), cinchonain A (6) and cinchonain B (7) were isolated from the stem bark of Trichilia gilgiana Harms. (Meliaceae). All compounds were isolated for the first time from this species. The structures were elucidated on the basis of spectral studies and by comparison of these data with those from the literature. Compounds 1, 2, 3, 6 and 7 were tested for in vitro antileishmanial activity against visceral leishmaniasis parasite Leishmania donovani and cytotoxicity against macrophage RAW 264.7 cell line. Compounds 1 and 3 showed the highest antileishmanial activity (IC 50 values of 6.044 and 6.804 µg/mL, respectively) with low cytotoxicity (CC 50 values of > 200 and 47.47 µg/mL, respectively), while compound 2 was moderately active on L. donovani promastigotes (IC 50 56.81 µg/mL).
UPLC-MSE Guided Isolation of New Antifeedant Limonoids from Fruits of Trichilia connaroides
UPLC-MS E guided isolation of CHCl 3 extract from the fruits of Trichilia connaroides yielded two new mexicanolide-type limonoidstrichanolide F (1) and trichanolideG (2) along with a known compound carapanolide U (3). The structures of the limonoids werecharacterized by extensive spectroscopic analysis (MS, IR, 2D NMR).These limonoids (1-3) were evaluated for their antifeedancyagainst Spodoptera litura F. To further explore and draw the meaningful structure activity relationship studies, secophragmalin-type limonoids namely secotrichagmalin B, C (4, 5) and semi-synthetic derivatives (5a-5l) were also screened for antifeedancy. The results revealed that trichanolide F (1) displayed highest antifeedant index (AFI) and caused larval mortality at 24 h.Derivative 5b caused larval toxicity, whereas 3, 5a, 5d and 5g lead to pupal mortality and 2, 5f, 5k and 5l caused adult deformities. Overall, the study provided new insights into the antifeedant potential of isolated and chemically modified limonoids from T. connaroides for the control of spodopteranpests.
Rubescins F–H, new vilasinin-type limonoids from the leaves of Trichilia rubescens (Meliaceae)
Zeitschrift für Naturforschung C, 2019
Three new limonoids, designated as rubescins F (1), G (2), and H (3), together with two known compounds of this type, TS1 (4) and trichirubine A (5), were isolated from methylene chloride/methanol extracts of Trichilia rubescens leaves. The structures of these compounds were elucidated based on 1D and 2D nuclear magnetic resonance (NMR) analysis and complemented by electrospray ionization high-resolution mass spectrometry results and by comparison to data of related compounds described in the literature and ab initio calculations. Rubescin F (1) is the first limonoid from Trichilia spp. with an oxetane ring between C-7 and C-14, which seems to be formed by the isomerization of TS1 (4). The γ-hydroxybutenolide rubescin G (2) is a potential precursor of trichirubine A (5), whereas rubescin H (3) is the first example of a triterpenoid with a single bond between C-7/C-14, forming a cyclopropane ring. The absolute configuration of these limonoids was derived from biosynthetic considerati...
Limonoids from the West African Trichilia welwitschii (Meliaceae)
Biochemical Systematics and Ecology, 2013
The seeds of Trichilia welwitschii C.DC. (Meliaceae) yielded three limonoids, dregeanin DM4 (1), reported here from a natural source for the first time, the known rohituka 3 (2) and trichilia lactone D5 (3). The bark yielded 28,29-dinorcycloart-24-ene-3,4,6-triol (4), sitosterol-3-O-b-D-glucoside, 4-hydroxy-N-methyl-L-proline, stigmasterol and sitosterol.
Biological Research, 2015
Background: Limonoids are highly oxygenated compounds with a prototypical structure. Their occurrence in the plant kingdom is mainly confined to plant families of Meliaceae and Rutaceae. Owing to their wide range of pharmacological and therapeutic properties, this study was aimed at investigating the potential nitric oxide (NO) and acetylcholinesterase (AChE) inhibitory activity and the cytotoxicity of three limonoids: trichilia lactone D5 (1), rohituka 3 (2) and dregeanin DM4 (3), isolated from Trichilia welwitschii C.DC. Results: Results indicated that the three limonoids had low cytotoxicity towards Vero cells with LC 50 values ranging from 89.17 to 75.82 μg/mL. Compounds (2) and (3) had lower cytotoxicity compared to puromycin and doxorubicin used as reference cytotoxic compounds. Compound (1) (LC 50 of 23.55 μg/mL) had good antiproliferative activity against RAW 264.7 cancer cells. At the lowest concentration tested (0.5 µg/mL), compound (2) and (3) released the lowest amount of nitric oxide (2.97 and 2.93 µM, respectively). The three limonoids had anti-AChE activity with IC 50 values ranged of 19.13 μg/mL for (1), 34.15 μg/mL for (2) and 45.66 μg/mL for (3), compared to galantamine (IC 50 of 8.22 μg/mL) used as positive control. Conclusion: The limonoid compounds studied in this work inhibited nitric oxide production in LPS-stimulated macrophages and had anti-AChE activity. Trichilia lactone D5 had potential antiproliferative activity against RAW 264.7 cancer cells. The limonoids had low cytotoxicity towards Vero cells lines. This study provided further examples of the importance of limonoids compounds as potential AChE inhibitors and anti-inflammatory agents targeting the inhibition of NO production.
Limonoids from Trichilia elegans ssp. elegans
Phytochemistry, 1997
From the seeds of Trichilia eleyans ssp. elegans, six new limonoids, four of which possess the uncommon seco-A, B and D carbocyclic rings, have been isolated, together with two known limonoids-kihadanin A and B and 3-O-fl-D-glucopyranosyl-sitosterol. The structures of these compounds have been established on the basis of 1D and 2D NMR spectroscopic techniques.
Natural product research, 2018
Two new tetranorterpenoid derivatives named rubescins I (1) and J (2), were isolated along with six known compounds including rubescin D (3), lichexanthone (4), scopoletin (5), scopoletin O-glycoside (6), β-sitosterol (7) and stigmasterol (8) from the stem bark of Trichilia rubescens (Meliaceae). The structures of the compounds were determined by means of MS, different NMR and by comparison with related data reported in the literature.
Chemical constituents from leaves and root bark of Trichilia monadelpha (Meliaceae)
Phytochemistry Letters, 2018
Two new limonoid derivatives designated, monadelphin A (1) and monadelphin B (2) and two new sesquiterpene derivatives named trichins A (3) and B (4) were isolated together with six known compounds (5-10) from the mixture of methylene chloride/methanol (1:1) extract of leaves and root bark of Trichilia monadelpha (Meliaceae) collected in Cameroon. The structures of the new compounds were unambiguously established by detailed spectroscopic analysis including 1D and 2D NMR data in conjunction with high resolution mass spectrometry data and by comparison of these data with those of related compounds described in the literature. Compounds 1-4 were screened for their cytotoxic potential. Compound 1 showed strong cytotoxicity against the mouse lymphoma L5178Y cell line with an IC 50 value of 0.62 μg/mL. The biogenetic origin of trichin B (4) from trichin A (3) was also postulated.
ChemInform, 2014
Three new limonoids, rubescins A-C (1-3), and three known compounds including, havanensin type limonoid TS3 (4), β-sitosterol, and stigmasterol were isolated from the root bark of Trichilia rubescens. Their structures were elucidated by means of extensive spectroscopic analyses, particularly one dimensional (1D)and 2D-NMR techniques in conjunction with mass spectrometry. Rubescins A-C (1-3) and limonoid TS3 (4) were evaluated for their protective effects against oxidative stress induced in HC-04 cells by H 2 O 2 . Compound (1) showed strong inhibitory effects on lactase dehydrogenase (LDH) leakage, being as active (IC 50 value of 0.0026 µM) as the positive control quercetin (IC 50 value of 0.0030 µM).