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Nutraceuticals and Functional Foods
Published in Robert E.C. Wildman, Richard S. Bruno, Handbook of Nutraceuticals and Functional Foods, 2019
Several triterpenes (examples in Figure 1.6) have been reported to have nutraceutical properties. These compounds include plant sterols; however, some of these structures may have been modified to contain fewer than 30 carbons. One of the most recognizable triterpene families is the limonoids. These triterpenes are found in citrus fruit and impart most of their bitter flavor. Limonin and nomilin are two triterpenoids that may have nutraceutical application, limonin more so than nomilin.20 Both of these molecules contain a furan component. In citrus fruit, limonoids can also be found with an attached glucose, forming a limonoid glycoside.21 As discussed above, the addition of the sugar group reduces the bitter taste tremendously and makes the molecule more water soluble. These properties may make it more attractive as a functional food ingredient. Saponins are also triterpene derivatives, and their nutraceutical potential is attracting interest.22,23
The Widening Panorama of Natural Products Chemistry in Brazil
Published in Luzia Valentina Modolo, Mary Ann Foglio, Brazilian Medicinal Plants, 2019
Maria Fátima das Graças Fernandes da Silva, João Batista Fernandes, Moacir Rossi Forim, Michelli Massaroli da Silva, Jéssica Cristina Amaral
Analyzing all the chemical data recorded in the NuBBe database for the species of a plant family, we verified that the Rutaceae were the most studied in Brazil with 12.5% of the total metabolites reported, followed by Meliaceae (9.1%), and a large part of the work was developed by da Silva's group. There is a general agreement between taxonomists that both these families should be placed in the same order, Sapindales (da Silva et al., 2010). The Rutaceae family includes about 150 genera with more than 1,500 species, which are distributed throughout the tropical and temperate regions of the world, being most abundant in tropical America, South Africa, Asia and Australia. Rutaceae constitute the largest group of Sapindales and are characterized by a great diversity of secondary metabolites not common in other families of the order. The most representative are alkaloids derived from anthranilic acid, coumarins, flavonoids and limonoids. There are 32 genera with about 200 species currently recognized in Brazil, and species of 24 genera have already been studied by da Silva's group. Meliaceae consists of about 550 species distributed between approximately 51 genera. There are six genera currently recognized in Brazil, and species of all genera have already been studied by the da Silva group. Limonoids, biosynthetically related compounds, are found in Meliaceae and Rutaceae. There are consistent differences between the limonoids of the Rutaceae and those of the Meliaceae.
Phytonutrients
Published in Parimelazhagan Thangaraj, Medicinal Plants, 2018
Ranganathan Kumar, Sulaxana Kumari Chauhan, Subramanian Vijayalakshmi, Shanmugam Nadanasabapathi
Limonoids. Limonoids are terpenes present in citrus fruit. Limonoids appear to provide chemotherapeutic activity by impeding the phase I enzymes and inducing phase II detoxification enzymes in the liver. D-Limonene, the most common monocyclic monoterpene, is found within orange peel oil, which inhibits pancreatic carcinogenesis induced in hamsters by N-nitrosobis(2-oxopropyl)amine and gastric carcinogenesis induced in Wistar rats by N-methyl-Nʹ-nitro-N-nitrosoguanidine. Limonoids may also provide protection to lung tissue (Nakaizumi et al. 1997; Uedo et al. 1999).
Integrated serum pharmacochemistry and investigation of the anti-gastric ulcer effect of Zuojin pill in rats induced by ethanol
Published in Pharmaceutical Biology, 2022
Jiaying Zhang, Yi Yin, Qianqian Xu, Xiaoqing Che, Chen Yu, Yan Ren, Dongsheng Li, Juanjuan Zhao
Limonoids are highly oxygenated and polycyclic triterpenoids and are also the main constituents of TR (Shi et al. 2020). They have variable chemical structures and exhibit a wide spectrum of bioactivities, including anticancer, anti-inflammatory, neuroprotection, antibacterial, antioxidant activities (Fan et al. 2019). Limonin (54), a compound characterised by TR, was first analysed using HRMS to find the typical fragment ions of limonoids (Figure 7A). Limonin displayed quasi-molecular ions [M + H]+ and other intense fragment ions, such as, [M + H-H2O]+, [M + H-2H2O]+ and [M + H-CO2]+. Moreover, the fragment ion at m/z 161.0595 (C10H9O2) was deemed the diagnostic ion for limonoids according to our study and references. Based on the diagnostic fragmentation ions [M-17]+, [M-35]+, [M-43]+, [M-45]+, m/z 161.0595, and accurate mass measurements, peaks 29, 49, 53, 57, 60, 65, and 66 were assigned to graucin A, evodirutaenin, 12α-hydroxylimonin, evodol, jangomolide, rutaevineacetate and calodendrolide, respectively. Typical mass spectra of evodol and its fragmentation pathways are presented in Figure 7B.
Toxicity of Suaeda maritima (L) against the Scirpophaga incertulas (W) and Xanthomonas oryzae pv. oryzae (Xoo) disease and its non-target effect on earthworm, Eisenia fetida Savigny
Published in Toxin Reviews, 2022
Haridoss Sivanesh, Narayanan Shyam Sundar, Sengottayan Senthil-Nathan, Vethamonickam Stanley-Raja, Ramakrishnan Ramasubramanian, Sengodan Karthi, Kanagaraj Muthu-Pandian Chanthini, Hesham Saleh M. Almoallim, Sulaiman Ali Alharbi
Many researchers have identified several novel plant phytochemical compounds which have toxic effects against insect pests, but which may be nontoxic or safer for humans and vertebrate animals (Zaka et al.2014, Bahrami et al.2016, Amala et al.2020). Exposure to phytochemicals ingested by herbivores can have large effects on the pest community composition (Vasantha-Srinivasan et al.2016). Isolation of novel plant essential oils botanicals, which are the odorous components, and secondary metabolites, can be separated from plant tissues through steam distillation. Some plant derived essential oil has even been reported to have significant impact on the development of S. litura (Shahriari et al.2017; Ponsankar et al.2016). Sublethal concentrations of ethyl acetate extract of S. maritima against S. incertulas extended the larval development. Methanol extracts and sterols from Myrtillocactus geometrizans produced abnormalities in the larvae and pupae of S. frugiperda and Tenebrio molitor (Céspedes et al. 2005). Senthil-Nathan et al. (2005, 2006) demonstrated that neem limonoids and azadirachtin inhibited the growth and development of larva and pupae of S. litura and C. medinalis.
Effects and mechanisms of natural plant active compounds for the treatment of osteoclast-mediated bone destructive diseases
Published in Journal of Drug Targeting, 2022
Qiang Xu, Zhiyou Cao, JiaQiang Xu, Min Dai, Bin Zhang, Qi Lai, Xuqiang Liu
7-Oxo-7-deacetoxygedunin, a gedunin-type limonoid derived from seeds of the mangrove plant, Xylocarpus moluccensis, inhibits the RANKL-stimulated recruitment of osteoclast precursor cells and TRAP activity in RAW 264.7 cells by downregulating the expression of NFATc1, CTSK, and interferon regulatory factor 8 by suppressing the RANKL-induced activation of p38 and ERK, and by inhibiting the nuclear localisation of NF-κB p65 subunit [140]. In summary, limonoids are less commonly used in the treatment of osteoclast-related diseases, despite their potent pharmacological effects.