Ultra-high performance liquid chromatography Q-Orbitrap MS/MS–based profiling and quantification of limonoids in Meliaceae plants

Mulani, Fayaj A.; Nandikol, Sharvani S; Kajjihundi, Jagadeesh S; Niranjana, Pathappa; Sharanappa, P.; Thulasiram, Hirekodathakallu V.

doi:10.1007/s00216-022-04169-2

Cited by 4 publications

(6 citation statements)

References 33 publications

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“…Four known compounds, 12α-acetoxyphragmalin 3,30-di-isobutyrate (6), 12α-acetoxyphragmalin 3-isobutyrate 30-propionate (7), phragmalin 3-isobutyrate 30-propionate (8) and phragmalin 3,30-di-isobutyrate (9) [19], were identified through the comparison of their spectroscopic data with the literature data.…”

Section: Resultsmentioning

confidence: 99%

“…Compounds 1-9 were characterized as chuktabumalin A (1), chuktabumalin B (2), chuktabumalin C (3), chuktabumalin D (4), chuktabumalin E (5), 12α-acetoxyphragmalin 3,30-di-isobutyrate (6), 12α-acetoxyphragmalin 3-isobutyrate 30-propionate (7), phragmalin 3-isobutyrate 30-propionate (8) and phragmalin 3,30-di-isobutyrate (9), respectively. Compounds 1-5 were structurally determined to be new phragmalin-type limonoids.…”

Section: Discussionmentioning

confidence: 99%

“…The further investigation of limonoids from this plant, provided five new phragmalintype limonoids, chuktabamalins A-E (1-5) (Figure 1) and four known compounds (6)(7)(8)(9), which were isolated from the EtOH extracts of the fruits of Chukrasia tabularis. Herein, the isolation and structure elucidation of the new compounds as well as their anti-inflammatory evaluation are reported.…”

Section: Introductionmentioning

confidence: 99%

“…Limonoids as the major secondary metabolites from Meliaceae family, are well-known for their abundance, structural diversity and a wide range of antifeedant, antimalarial, antimicrobial, cytotoxic and growth-regulating activities [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 ]. The genus Chukrasia (Meliaceae) comprises only Chukrasia tabularis A. Juss and Chukrasia tabularis var.…”

Section: Introductionmentioning

confidence: 99%

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Phragmalin-Type Limonoids from the Fruits of Chukrasia tabularis and Their Anti-Inflammatory Activity

Dai

Xin

et al. 2023

Molecules

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Phytochemical investigation on the fruits of C. tabularis led to the isolation of five new phragmalin-type limonoids (1–5) and four known ones (6–9). The structures of the new compounds 1–5, named chuktabamalins A–E, were elucidated via spectroscopic techniques (HRESIMS, 1D and 2D NMR) and were comparable with the literature data of known compounds. In addition, new compounds were evaluated for in vitro anti-inflammatory activity. Compounds 1, 2, 3 and 5 showed moderate anti-inflammatory activity with IC50 values of 21.72 ± 2.79, 23.29 ± 1.00, 47.08 ± 3.47 and 66.67 ± 2.89 μM, respectively.

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Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Phragmalin-Type Limonoids from the Fruits of Chukrasia tabularis and Their Anti-Inflammatory Activity

Dai

Xin

et al. 2023

Molecules

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“…The elucidation of the neem genome was a gradual process, culminating in its completion in 2011 [7] . Rapid advancements in sequencing technology have propelled comprehensive analysis of the neem genome and Leaves, fruits, flowers Liquid-solid extraction -Acetone, Ethanol, Methanol UHPLC Q-Orbitrap [91] Seed, Leaf Ultrasonic-assisted method 40 min acetonitrile LC-Q-TOF-MS [76] Seed Liquid-solid extraction 48 h n-Hexane HPLC-UV [92] Seed Schroeder and Nakanishi Method 30 min Alcohol SFC [93] Kernels Soxhlet extraction 2 h n-Hexane HPLC [79] Leaves, bark, roots Soxhlet extraction -Water LC-MS [94] Fruit Reflux extraction 48 h Alcohol HPLC-UV [92] Seed Thorns extraction 24-72 h Carbinol HPLC-UV [72] Seed Screw press 20 min -- [95] Leaf Pressurized liquid extraction -Carbinol HPLC-UV [71] Bark Shaking -Methanol Spectrophotometric [96] Seed Supercritical fluid extraction 150 min Methanol HPLC [97] Kernels Cold extraction -Ethanol HPLC [98] Leaf Cold extraction 48 h Petroleum ether - [99] Seeds Cold-pressing -Hexane HPLC-UV [100] Fruits Ultrasound-assisted extraction 30 min Ethanol HPLC-UV [82] Seeds Maceration 3 d Methanol HPLC-UV [71] Leaf Percolation, decoction, freeze drying or spray drying 6 h Water TLC [101] Fruits Percolation -Hexane HPLC-UV [102] HPLC: High performance liquid chromatography; LC-MS: Liquid chromotography with mass spectrometry; LC-Q-TOF-MS: Ultra-high performance liquid chromatography coupled with quadrupole/ time of flight mass spectrometry; SFC: Supercritical fluid chromatography; TLC: Thin layer chromatography; UHPLC: Ultra high performance liquid chromatography; UPLC-QTOF: Ultra performance liquid chromatography-quadrupole-time-of-flight mass spectrometry.…”

Section: Progress In Transcriptome/genome Researchmentioning

confidence: 99%

A comprehensive review of azadirachtin: physicochemical properties, bioactivities, production, and biosynthesis

Su,

Liang,

Xue

et al. 2023

Acupuncture and Herbal Medicine

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Azadirachtin, a complex tetratriterpenoid limonin with potent insecticidal properties, is the most widely used biological pesticide worldwide. Its versatile pharmacological applications include the inhibition of tumor growth and anti-malarial, anti-bacterial, and anti-inflammatory properties. Azadirachtin plays a pivotal role in pest control and novel drug development. The primary source of azadirachtin is the neem tree (Azadirachta indica A. Juss), with an azadirachtin content ranging from 0.3% to 0.5%. Despite the market demand for botanical pesticides reaching approximately 100,000 tons per year, the annual neem production in China is only 1.14 tons. Although azadirachtin can be obtained through plant extraction or chemical synthesis, the quantity obtained does not meet the market demand in China. The sluggish pace of azadirachtin biosynthesis results from the limited availability of genetic information and the complexity of the synthetic pathway. Recent advancements in azadirachtin biosynthesis hold promise as an efficient collection method. In this study, we explored the physicochemical properties, biological activities, mechanisms of action, and acquisition methods of azadirachtin. We also delved into recent progress in azadirachtin biosynthesis and assessed potential future usage challenges. This study aims to establish a theoretical foundation for the scientific application and efficient synthesis of azadirachtin, offering valuable reference information to the industry.

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Limonoids isolated from Chisocheton ceramicus Miq. and the antiadipogenic mechanism of action of ceramicine B

Bailly

2024

Archiv der Pharmazie

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Different types of limonoids have been isolated from plants of the Chisocheton genus, notably from the species Chisocheton ceramicus Miq. which is largely distributed in the Indonesian archipelago and Malaysia region. A variety of natural products have been found in the bark of the tree and characterized as antimicrobial and/or antiproliferative agents. The isolated limonoids include chisomicines A–E, proceranolide, and a few other compounds. A focus is made on a large series of limonoids designated ceramicines A to Z including derivatives with antiparasitic activities, antioxidant, antimelanogenic, and antiproliferative effects and/or acting as regulators of lipogenesis. The lead compound in the series is ceramicine B functioning as a potent inhibitor of lipid droplet accumulation (LDA). Extracts from Chisocheton ceramicus and ceramicines have shown anti‐LDA effects, with little or no cytotoxic effects. Ceramicine B is the most active compound functioning as a regulator of lipid storage in cells and tissues. Ceramicine B is a transcriptional repressor of peroxisome proliferator‐activated receptor γ (PPARγ) and an inhibitor of phosphorylation of the transcription factor FoxO1, acting via an upstream molecular target. Targeting of glycogen synthase kinase‐3β is proposed, based on the analogy with structurally related limonoids known to target this enzyme, and supported by a molecular docking analysis. The target and pathway implicated in ceramicine B activity are discussed. The analysis shed light on ceramicine B as a natural product precursor for the design of novel compounds capable of reducing LDA in cells and of potential interest for the treatment of obesity, liver diseases, and other pathologies.

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Ultra-high performance liquid chromatography Q-Orbitrap MS/MS–based profiling and quantification of limonoids in Meliaceae plants

Cited by 4 publications

References 33 publications

Phragmalin-Type Limonoids from the Fruits of Chukrasia tabularis and Their Anti-Inflammatory Activity

Phragmalin-Type Limonoids from the Fruits of Chukrasia tabularis and Their Anti-Inflammatory Activity

A comprehensive review of azadirachtin: physicochemical properties, bioactivities, production, and biosynthesis

Limonoids isolated from Chisocheton ceramicus Miq. and the antiadipogenic mechanism of action of ceramicine B

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