Chemical Structures and Biological Activities of Limonoids from the Genus Swietenia (Meliaceae)

Sun, Yun Peng; Jin, Wen Fang; Wang, Yong Yue; Wang, Gang; Morris‐Natschke, Susan L.; Liu, Jin Song; Wang, Guo Kai; Lee, Kuo Hsiung̀

doi:10.3390/molecules23071588

Cited by 26 publications

(22 citation statements)

References 77 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Until now, they are reported to distribute mainly in Rutaceae and Meliaceae plant resources. Previous studies suggested that limonoids exhibited strong anti-inflammatory activity (Akihisa et al, 2017;Hu et al, 2018;Sun et al, 2018).…”

Section: Introductionmentioning

confidence: 99%

Anti-inflammatory Limonoids From Cortex Dictamni

et al. 2020

View full text Add to dashboard Cite

The root barks of perennial herb Dictamnus dasycarpus (Cortex Dictamni) were reported to be rich in anti-inflammation activity constituents, limonoids. Then, the investigation of anti-inflammation therapeutic limonoids from this plant was developed in the present study. Through the combination of various chromatographies isolation, six new limonoids, named dictamlimonol A (1), dictamlimonoside B (2), and dictamlimonols C-F (3-6), along with seven known ones (7-13), were obtained. Their structures were ascertained based on the extensive spectroscopic methods and ECD data analysis. Among them, compound 1 was the first 7,19-epoxy limonoid found in natural products. The anti-inflammatory effects of all limonoids were evaluated in lipopolysaccharide (LPS)-treated RAW 264.7 cell lines. Compounds 5, 7-11, and 13 were found to inhibit LPS-induced nitric oxide (NO) production. Moreover, dictamlimonol D (5), fraxinellone (11), and dasylactone A (13) were found to reduce the LPS-induced expressions of interleukin-6 (IL-6), tumor necrosis factor (TNF-α), inducible nitric oxide synthase (iNOS), nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB), and cyclooxygenase-2 (COX-2) at the protein levels in a dose-dependent manner. These findings support that the administration of Cortex Dictamni may be beneficial for inflammation.

show abstract

Section: Introductionmentioning

confidence: 99%

Anti-inflammatory Limonoids From Cortex Dictamni

et al. 2020

View full text Add to dashboard Cite

show abstract

“…Phytochemical studies have revealed a great variety of pharmacological activities [ 22 , 23 , 24 ] as well as health-promoting and disease-preventing properties exhibited by limonoids [ 25 , 26 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Degraded Limonoid Analogs as New Antibacterial Scaffolds against Staphylococcus aureus

et al. 2020

View full text Add to dashboard Cite

Staphylococcus aureus and methicillin-resistant Staphylococcus aureus (MRSA) have become serious infections in humans and ruminants. S. aureus strains are showing rapid changes to develop resistance in traditional antibiotic-containing systems. In the continuous fierce fight against the emergent multi-drug resistant bacterial strains, straightforward and scalable synthetic procedures to produce new active molecules are in demand. Analysis of molecular properties points to degraded limonoids as promising candidates. In this article, we report a simple synthetic approach to obtain degraded limonoid analogs as scaffolds for new antibacterial molecules. The minimum inhibitory concentrations against S. aureus were evaluated for the stereoisomer mixtures by the broth microdilution method. Analysis of results showed that the acetylated derivatives were the most active of them all.

show abstract

“…e Meliaceous plant S. macrophylla grows widely in Central and South American countries, India, Malaysia, and China [1,4]. It is rare to see in Vietnam, and the phytochemical investigation, as well as antifungal properties of the local species, has not been reported much.…”

Section: Discussionmentioning

confidence: 99%

“…From the fruits of K. senegalensis, Abdelgaleil et al (2004) also successfully isolated bioactive limonoids such as seneganolide A, 2-acetoxyseneganolide A, and methyl 6-hydroxyangolensate with antifungal effects on B. cinerea [9]. In our ongoing research studies on bioactive limonoids from Meliaceous plants growing in Vietnam, we successfully isolated and identified nine limonoids from Melia dubia (1-2), Aphanamixis polystachya (3)(4)(5), and Swietenia macrophylla (6)(7)(8)(9). e antifungal potential of the isolated limonoids against various phytopathogenic fungi including F. oxysporum, M. oryzae, S. rolfsii, R. solani, Alternaria spp., B. cinerea, and oomycetes Phytophthora species was evaluated in vitro.…”

Section: Introductionmentioning

confidence: 99%

Characterization and Antifungal Activity of Limonoid Constituents Isolated from Meliaceae Plants Melia dubia, Aphanamixis polystachya, and Swietenia macrophylla against Plant Pathogenic Fungi In Vitro

Tan

Trung

Dang

et al. 2021

Journal of Chemistry

View full text Add to dashboard Cite

The plants of Meliaceae are native to tropical and subtropical regions as the Americas, west India, Southeast Asia, and Southern China. Many species of the genera Khaya, Swietenia, Aphanamixis, and Melia in this family are known as medicinal plants and have biological activities such as antiviral, antimicrobial, antifeeding, insecticidal, and cytotoxic properties. The objectives of this research are to characterize and evaluate the bioactive limonoids from several plants of Meliaceae against phytopathogenic fungi. During the search of antifungal compounds from the plants of Meliaceae, the three methanol extracts of Melia dubia, Aphanamixis polystachya, and Swietenia macrophylla were found to suppress the mycelial growth of several phytopathogenic fungi. Nine limonoids isolated from M. dubia (1–2), A. polystachya (3–5), and S. macrophylla (6–9) were evaluated, for the first time, their antifungal effectiveness against nine phytopathogenic fungi Fusarium oxysporum, Magnaporthe oryzae, Sclerotium rolfsii, Rhizoctonia solani, Alternaria spp., and Botrytis cinerea, and three oomycetes Phytophthora species. Limonoids 2, 3, 6, and 8 displayed a remarkable broad-spectrum antifungal activity against all the test fungi. Sclerotium rolfsii was highly sensitive to the four limonoids with IC50 values ranging from 79.4 to 128.0 µg/mL. Notably, chisocheton compound G (3) isolated from A. polystachya and khayanolide B (8) isolated from S. macrophylla were the most potent antifungal limonoids and exhibited a dose-dependent activity against Phytophthora species. Compounds 2 and 9 displayed moderate activity against M. oryzae. Our study results demonstrated the discovery of antifungal and lead compounds from the group of limonoids for application in the control of fungal plant diseases.

show abstract

Chemical Structures and Biological Activities of Limonoids from the Genus Swietenia (Meliaceae)

Cited by 26 publications

References 77 publications

Anti-inflammatory Limonoids From Cortex Dictamni

Anti-inflammatory Limonoids From Cortex Dictamni

Synthesis of Degraded Limonoid Analogs as New Antibacterial Scaffolds against Staphylococcus aureus

Characterization and Antifungal Activity of Limonoid Constituents Isolated from Meliaceae Plants Melia dubia, Aphanamixis polystachya, and Swietenia macrophylla against Plant Pathogenic Fungi In Vitro

Contact Info

Product

Resources

About