New limonoids isolated from the bark of Melia toosendan

Zhang, Qiong; Zheng, Qinghong; Sang, Yi-Shu; Sung, Herman H.-Y.; Min, Zhi-Da

doi:10.1016/s1875-5364(18)30136-5

Cited by 5 publications

(4 citation statements)

References 8 publications

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“…Compounds 1 and 2 were isolated from 100% n-hexane fraction while compound 3was isolated from ethyl acetate: methanol (60:40 v/v). 13 C-NMR data were in agreement with previous studies [33], so that the compound was established as 1αhydroxyl-3α-acetyl-7α-tigloyl-12β-ethoxyl-nimbolinin (12-ethoxynimbolininH)which was previously isolated from the bark of other Melia species [33,34]. C-NMRand UV spectral data with different shift reagents were in accordance with previous study [35], confirming that compound was genistein 7-O-glucoside.…”

Section: Isolation and Characterization Of A Indica L Compoundssupporting

confidence: 88%

Bioactive Azadirachta indica and Melia azedarach leaves extracts with anti-SARS-CoV-2 and antibacterial activities

et al. 2023

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The leaves of Azadirachta indica L. and Melia azedarach L., belonging to Meliaceae family, have been shown to have medicinal benefits and are extensively employed in traditional folk medicine. Herein, HPLC analysis of the ethyl acetate fraction of the total methanolic extract emphasized the enrichment of both A. indica L., and M. azedarach L. leaves extracts with phenolic and flavonoids composites, respectively. Besides, 4 limonoids and 2 flavonoids were isolated using column chromatography. By assessing the in vitro antiviral activities of both total leaves extracts against Severe Acute Respiratory Syndrome Corona virus 2 (SARS-CoV-2), it was found that A. indica L. and M. azedarach L. have robust anti-SARS-CoV-2 activities at low half-maximal inhibitory concentrations (IC50) of 8.451 and 6.922 μg/mL, respectively. Due to the high safety of A. indica L. and M. azedarach L. extracts with half-maximal cytotoxic concentrations (CC50) of 446.2 and 351.4 μg/ml, respectively, both displayed extraordinary selectivity indices (SI>50). A. indica L. and M. azedarach L. leaves extracts could induce antibacterial activities against both Gram-negative and positive bacterial strains. The minimal inhibitory concentrations of A. indica L. and M. azedarach L. leaves extracts varied from 25 to 100 mg/mL within 30 min contact time towards the tested bacteria. Our findings confirm the broad-spectrum medicinal value of A. indica L. and M. azedarach L. leaves extracts. Finally, additional in vivo investigations are highly recommended to confirm the anti-COVID-19 and antimicrobial activities of both plant extracts.

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Section: Isolation and Characterization Of A Indica L Compoundssupporting

confidence: 88%

Bioactive Azadirachta indica and Melia azedarach leaves extracts with anti-SARS-CoV-2 and antibacterial activities

et al. 2023

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“…Several limonoids also possessed noticeable hepatotoxicity. Among them, 12-ethoxynimbolinins G and 1,12-diacetyltrichilin B were toxic to SMMC-7721 cells, with IC 50 values of 27.6 and 0.36 µM, respectively, and trichilinin E had cytotoxicity against HepG2 cell ( Yuan et al, 2013 ; Zhou et al, 2016 ; Zhang et al, 2018 ).…”

Section: Biological Activities Of Limonoidsmentioning

confidence: 99%

Limonoids From the Genus Melia (Meliaceae): Phytochemistry, Synthesis, Bioactivities, Pharmacokinetics, and Toxicology

Fan

Wang

et al. 2022

Front. Pharmacol.

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Limonoids, as the vital bioactive chemical compounds in genus Melia plants, have attracted significant attention owing to their exclusive structural characteristics and remarkable biological activity. These compounds can be usually classified into two categories, including the ring-intact group and the ring-C-seco group. Benefiting from the development of separation and analysis technology, more than 200 limonoids have been isolated and identified from this genus. There is growing evidence that limonoids from genus Melia possess diverse pharmacological activities, especially anti-cancer effects, insecticidal activities, and anti-botulism effects. Toosendanin, one of the paramount limonoids, was considered as the pivotal bioactive marker in two medicinal herbs, including Melia toosendan Sieb. et Zucc and Melia azedarach L. In particular, limonoids are found to exhibit non-negligible toxic effects, a finding which needs further research. Besides this, the lack of clinical research data seriously hinders its further development and utilization, and necessary clinical trials should be taken into consideration. In this review, we systematically summarized the phytochemical compounds and their synthesis methods, pharmacological activities, and the structure–activity relationship, pharmacokinetics, and toxicology of genus Melia-derived limonoids. We believe that this up-to-date review could provide scientific evidence for the application of limonoids as agents beneficial to health in future clinical practice.

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“…The cleavage sites are generally located at C-3/4 in the A ring, C-7/8 in the B ring, C-12/13 in the C ring, and C-16/17 in the D ring and exist in the form of corresponding lactones . More than 2000 limonoids have been reported; however, only less than 50 ring C- seco compounds were reported mainly from the Azadirachta and Melia genera − in the past decade. In these reports, the structures of ring C- seco limonoids are either completely ring-opened to form a C-12 aldehyde or carboxylic acid branching chain (such as the salannin class) or ketalized with OH-15 to form a 12,15-ether bridge (such as the nimbolinin class) .…”

mentioning

confidence: 99%

“…More than 2000 limonoids have been reported; however, only less than 50 ring C- seco compounds were reported mainly from the Azadirachta and Melia genera − in the past decade. In these reports, the structures of ring C- seco limonoids are either completely ring-opened to form a C-12 aldehyde or carboxylic acid branching chain (such as the salannin class) or ketalized with OH-15 to form a 12,15-ether bridge (such as the nimbolinin class) . However, ring C- seco limonoids with a 12,13-ether bridge moiety obtained directly by Baeyer–Villiger oxidation have not been found yet in nature.…”

mentioning

confidence: 99%

Limonoids with Diverse Oxidation Patterns of C-12 Indicating a Complete Ring C-seco Biogenetic Pathway from Munronia unifoliolata

Sun

et al. 2021

J. Nat. Prod.

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Munrolins A–Q (1–17), 17 new ring C-seco limonoids with diverse oxidative patterns of C-12, together with nine known analogues (18–26), were isolated from the CH2Cl2 extract of Munronia unifoliolata. The planar structures were elucidated by a combination of 1D and 2D NMR and HR-MS analyses, while the absolute configurations were confirmed by ECD calculations and single-crystal X-ray diffraction. Munrolins A (1) and B (2) were first identified as ring C-seco limonoids with a 12,13-ether bridge moiety. Munrolins C–J (3–10) have a rare reduced primary alcohol fragment, while munrolin Q (17) has an unusual ketal fragment formed by dehydration of C-12/14. These limonoids with diverse alcohol and aldehyde type C11/12 branches may be generated through different degrees of reduction after the Baeyer–Villiger oxidation at the C ring, as key intermediates to supplement the biogenetic pathway of ring C-seco limonoids. Compounds 11, 19, and 26 could reverse the multidrug resistance of MCF-7/doxorubicin cells with reversal fold values of 5.2, 4.5, and 18.3, respectively.

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New limonoids isolated from the bark of Melia toosendan

Cited by 5 publications

References 8 publications

Bioactive Azadirachta indica and Melia azedarach leaves extracts with anti-SARS-CoV-2 and antibacterial activities

Bioactive Azadirachta indica and Melia azedarach leaves extracts with anti-SARS-CoV-2 and antibacterial activities

Limonoids From the Genus Melia (Meliaceae): Phytochemistry, Synthesis, Bioactivities, Pharmacokinetics, and Toxicology

Limonoids with Diverse Oxidation Patterns of C-12 Indicating a Complete Ring C-seco Biogenetic Pathway from Munronia unifoliolata

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