Qizhi Wang

Euodia rutaecarpa (Juss.) Benth., commonly known as Wu Zhu Yu in traditional Chinese medicine (TCM), is a widely used medicinal plant belonging to the Rutaceae family. With a rich history spanning thousands of years, it is primarily valued for its fruits, which have been utilized in East Asia to treat a variety of ailments. E. rutaecarpa exhibits a broad range of pharmacological effects, including the ability to inhibit gastrointestinal motility, relieve diarrhea, prevent ulcers, and exert anti-tumor and anti-inflammatory properties. Modern pharmacological studies have further revealed its anti-tumor activity, immune-modulating effects, and potential role in weight management. Given its diverse therapeutic applications, there has been a significant increase in research related to E. rutaecarpa in recent years. According to the investigation, research on E. rutaecarpa began as early as 1915. This review systematically examines the latest research progress on the bioactive chemical constituents, pharmacological activities, and clinical applications of E. rutaecarpa. It comprehensively summarizes the bioactive compounds identified in this plant genus, including 58 indolo quinazoline alkaloids, 85 quinolone alkaloids, and 21 limonoid components. Additionally, it provides an in-depth analysis of the specific mechanisms underlying the pharmacological activities of E. rutaecarpa. Finally, the review discusses the limitations of current research, such as the risk of neurotoxicity, and outlines future research directions, including toxicity optimization through structural modification and the development of novel drug delivery systems. This work provides a theoretical foundation for the in-depth development of E. rutaecarpa and offers innovative perspectives for the research paradigm of multi-target natural medicine.

The Euodia genus comprises numerous untapped medicinal plants that warrant thorough evaluation for their potential as valuable natural sources of herbal medicine or food flavorings. In this study, untargeted metabolomics and in vitro functional methods were employed to analyze fruit extracts from 11 significant species of the Euodia genus. An investigation of the distribution of metabolites (quinolone and indole quinazoline alkaloids) in these species indicated that E. rutaecarpa (Euodia rutaecarpa) was the most widely distributed species, followed by E. compacta (Euodia compacta), E. glabrifolia (Euodia glabrifolia), E. austrosinensis (Euodia austrosinensis), and E. fargesii (Euodia fargesii). There have been reports on the close correlation between indole quinazoline alkaloids and their anti-tumor activity, especially in E. rutaecarpa fruits which exhibit effectiveness against various types of cancer, such as SGC-7901, Hela, A549, and other cancer cell lines. Additionally, the E. rutaecarpa plant contains indole quinazoline alkaloids, which possess remarkable antibacterial properties. Our results offer novel insights into the utilization of Euodia resources in the pharmaceutical industry.

Background: Atractylodes lanceapossesses immense potential for application in pharmaceuticals, food and health products, cosmetics, and agricultural production. However, due to the depletion of natural resources, researchers are investigating high-yield and efficient cropping models for Atractylodes. Until now, the differences and changes of chemical constituents in Atractylodes under different cropping patterns and growth years have been very limited, so further exploration and research are needed. Materials and methods: Raw materials for Atractylodes are supplied by Maoshan Traditional Chinese Medicine Planting Company, a laboratory cooperative planting site. The standard product is provided by China Institute of Food and Drug Control. The samples and standards were dissolved in methanol for analysis during October-December 2022. Tests were performed by utrl high performance liquid chromatography-mass spectrometry (UPLC-Q/TOF-MS) and gas chromatography-mass spectrometry (GC-MS) for quantitative and metabolomic analysis. Stoichiometric analysis and metabolic pathway analysis were conducted based on mass spectrometry Results: After conducting content tests, it was discovered that the intercropped biennial Atractylodescontained the required 3% or more atractylodin. After testing, Atractylodes lancea samples did not contain phorate pesticides. On this basis, 411 volatile metabolites were extracted and identified, while 111 secondary metabolites were identified. 36 volatile metabolites and 26 secondary metabolites showed significant differences between the two cropping patterns and different growth years. Through metabolic pathway enrichment analysis, it was found that volatile metabolites had significant differences in the biosynthesis of unsaturated fatty acids pathway. Conclusions: The biennial intercropping approach, yielded Atractylodes extracts with content levels that were 1.8, 1.9, and 2.3 times higher than those derived from biennial monocrop, annual intercrop, and annual monocrop, respectively. It was also found that secondary metabolites more accurately reflected the distinctions brought about by the different cropping patterns and growth periods in Atractylodes. Hence, this experiment holds significant value as a reference for developing environmentally sustainable agricultural practices for growing this herb. It can also be used to establish an authentic production area model and for the evaluation of herb quality.

Pathogenic plant oomycetes cause devastating damage to fruits and vegetables worldwide. Plant essential oils (EOs) are known to be promising candidates for the development of fungicides. In this study, we isolated twelve EOs from Tetradium ruticarpum, Tetradium daniellii, Tetradium fraxinifolium, Zanthoxylum armatum, Ruta graveolens, and Citrus medica leaves and fruits. We then investigated their chemical composition and antifungal activity against phytopathogenic oomycetes. Our results demonstrated that Z. armatum fruit essential oil (ZFO) in particular substantially inhibited the mycelial growth of Phytophthora capsici. Similarly, ZFO also strongly suppressed spore production and germination of P. capsici, and the application of ZFO significantly reduced disease symptoms caused by P. capsici in pepper. Furthermore, results from microscopic and biochemical studies indicated that ZFO damaged the ultrastructure and destroyed the membrane integrity of P. capsici, leading to the leakage of the cellular contents and ultimately causing cell death. It was concluded that ZFO could enhance the activities of defense-related enzymes in pepper fruits, which may also be responsible for the inhibition of phytophthora disease. Moreover, linalool and D-limonene were proven to be the primary effective components of ZFO. Our results collectively indicate that ZFO could be a potential candidate for the management of disease caused by P. capsici.

Secoatractylohexone A (1), an unprecedented secoguaiane lactone glycoside featuring 6/7 cores and dihydroxy-9-guaine-3-one 11-O-β-d-glucopyranoside (2), a 9,10-unsaturated guaiene-type glycoside possessing an uncommon scaffold, were isolated from the water-soluble portion of the ethanolic extract of Atractylodes lancea rhizomes together with five known compounds (3–7). The structures of 1 and 2 were elucidated on the basis of extensive spectroscopic data and application of the CD technique. The potential biological activities of secoatractylohexone A were predicted by network pharmacology in silico, the result of which indicated that secoatractylohexone A may be used to treat type II diabetes.

Tetradium ruticarpum (Juss.) Benth. belong to the family of Rutaceae. The complete and nearly ripe fruits of T. ruticarpum is used as traditional Chinese medicine and phytochemical investigations have been conducted on extracts of the seeds of T. ruticarpum to provide scientific validation of its properties. In this study, we successfully isolated two new quinolone alkaloids (1-2) from the MeOH extractive of nearly ripe fruits of T. ruticarpum. The structure elucidation of these compounds was determined by one- and two-dimensional nuclear magnetic resonance, ultraviolet and electrospray ionisation time-of-flight mass spectrometry. This finding expands the understanding of the natural constituents of the Rutaceae, in particular, the Tetradium genera.

A rare new quinolone alkaloid containing three degrees of unsaturation in the side chain, named as 1-methyl-2-[(6Z,9Z,12Z)-6,9,12-pentadecatriene]-4(1H)-quinolone (1), together with three known quinolone alkaloids 1-methyl-2-[(6Z,9Z)-6,9-pentadecadienyl]-4(1H)-quinolone (2), 1-methyl-2-[(4Z,7Z)-4,7-tridecadienyl]-4(1H)-quinolone (3), 1-methyl-2-[(Z)-8-tridecenyl]-4(1H)-quinolone (4), were isolated from the fruits of Tetradium ruticarpum (A.Juss.) T.G.Hartley. Their structures were elucidated by physicochemical properties and spectroscopic data. All compounds were evaluated for their cytotoxic activities against three human tumor cell lines, including Lovo, MDA-MB-231, HeLa cells, by MTT method in 96-well microplates, and compounds 1 exhibited potent activity against MDA-MB-231 cells with IC50 values of 7.95 μM.

Tetradium trichotomum Lour., is a plant species endemic to tropical South East Asia with particular medicinal importance. However, very little analysis in this plant has been studied up to now from a phytochemical viewpoint. One new amide alkaloid (wuchuyuamide V, 1), as well as two known amide alkaloids-wuchuyuamide III (2), and wuchuyuamide I (3) were obtained from the fruits of T. trichotomum for the first time. The structures of wuchuyuamide V (1) and wuchuyuamide III (2) were unambiguously elucidated by 1D and 2D-NMR spectra, mass spectrometry, and single-crystal X-ray diffraction. Graphical Abstract