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Journal articles on the topic 'Limonoid'

Author: Grafiati

Published: 4 June 2021

Last updated: 21 February 2023

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1

Tambunan, Ghina Uli Felicia, Nurlelasari Nurlelasari, and Shabarni Gaffar. "Senyawa Golongan Limonoid dari Tanaman Genus Chisocheton dan Aktivitas Antikankernya." ALCHEMY Jurnal Penelitian Kimia 17, no. 1 (2021): 10. http://dx.doi.org/10.20961/alchemy.17.1.41279.10-26.

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<p>Indonesia merupakan negara yang kaya akan keanekaragaman hayati. Terdapat banyak tanaman yang mengandung senyawa metabolit sekunder yang memiliki aktivitas biologi sehingga berpotensi untuk digunakan sebagai obat, salah satunya adalah genus <em>Chisocheton</em>. Tanaman genus <em>Chisocheton </em>sudah banyak dilaporkan mengandung senyawa triterpenoid, seskuiterpenoid, limonoid, steroid, dan fenol. Limonoid merupakan turunan triterpenoid yang paling banyak ditemukan pada tanaman genus <em>Chisocheton</em>. Lebih dari tiga puluh senyawa golongan limo

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2

Dandekar, Deepak V., Guddadarangavvanahally K. Jayaprakasha, and Bhimanagouda S. Patil. "Simultaneous Extraction of Bioactive Limonoid Aglycones and Glucoside from Citrus aurantium L. Using Hydrotropy." Zeitschrift für Naturforschung C 63, no. 3-4 (2008): 176–80. http://dx.doi.org/10.1515/znc-2008-3-403.

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Citrus limonoids were demonstrated to possess potential biological activities in reducing the risk of certain diseases. Limonoids are present in citrus fruits in the form of aglycones and glucosides. At present, limonoid aglycones and limonoid glucosides are extracted in multiple steps using different solvents. In order to understand their potential bioactivity, it may be beneficial to isolate and purify these compounds using environment friendly methods. A new method of extraction and purification of limonoids was established using a hydrotrope polystyrene adsorbent resin. Extraction of aglyc

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3

Hodgson, Hannah, Ricardo De La Peña, Michael J. Stephenson, et al. "Identification of key enzymes responsible for protolimonoid biosynthesis in plants: Opening the door to azadirachtin production." Proceedings of the National Academy of Sciences 116, no. 34 (2019): 17096–104. http://dx.doi.org/10.1073/pnas.1906083116.

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Limonoids are natural products made by plants belonging to the Meliaceae (Mahogany) and Rutaceae (Citrus) families. They are well known for their insecticidal activity, contribution to bitterness in citrus fruits, and potential pharmaceutical properties. The best known limonoid insecticide is azadirachtin, produced by the neem tree (Azadirachta indica). Despite intensive investigation of limonoids over the last half century, the route of limonoid biosynthesis remains unknown. Limonoids are classified as tetranortriterpenes because the prototypical 26-carbon limonoid scaffold is postulated to b

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4

De La Peña, Ricardo, Hannah Hodgson, Jack Chun-Ting Liu, et al. "Complex scaffold remodeling in plant triterpene biosynthesis." Science 379, no. 6630 (2023): 361–68. http://dx.doi.org/10.1126/science.adf1017.

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Triterpenes with complex scaffold modifications are widespread in the plant kingdom. Limonoids are an exemplary family that are responsible for the bitter taste in citrus (e.g., limonin) and the active constituents of neem oil, a widely used bioinsecticide (e.g., azadirachtin). Despite the commercial value of limonoids, a complete biosynthetic route has not been described. We report the discovery of 22 enzymes, including a pair of neofunctionalized sterol isomerases, that catalyze 12 distinct reactions in the total biosynthesis of kihadalactone A and azadirone, products that bear the signature

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5

Dandekar, Deepak, G. K. Jayaprakasha, and Bhimanagouda Patil. "Citrus Bioactive Limonoid Extraction using Environment-friendly Hydrotropy." HortScience 41, no. 4 (2006): 1008C—1008. http://dx.doi.org/10.21273/hortsci.41.4.1008c.

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Citrus consumption has been shown to promote human health due to presence of several bioactive compounds. In the process of understanding the health benefits of citrus, we need to isolate and characterize these compounds. Limonoids are one of such prominent, but lesser-known phytonutrients that have been shown to prevent cancers of the mouth, skin, lung, breast, and colon. With the growing interest in the health-promoting properties of citrus limonoids, the demand for these bioactives has significantly increased. It has been critical to explore environment-friendly extraction methods rather th

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6

Mandadi, Kranthi K., Guddadarangavvanahally K. Jayaprakasha, Narayan G. Bhat, and Bhimanagouda S. Patil. "Red Mexican Grapefruit: A Novel Source for Bioactive Limonoids and their Antioxidant Activity." Zeitschrift für Naturforschung C 62, no. 3-4 (2007): 179–88. http://dx.doi.org/10.1515/znc-2007-3-405.

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Abstract Citrus limonoids have shown to inhibit the growth of cancer in colon, lung, mouth, stomach and breast in animal and cell culture studies. For the first time in the present study, an attempt has been made to isolate antioxidant fractions and five limonoids from red Mexican grapefruit seeds. Defatted seed powder was successively extracted with hexane, ethyl acetate (EtOAc), acetone, methanol (MeOH) and MeOH/water and the extracts were concentrated under vacuum. Radical scavenging activity of 1,1-diphenyl-2-picrylhydrazyl (DPPH) and total phenolic content were also measured for compariso

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7

Jogia, Madhu K., and Raymond J. Andersen. "Limonoids from the Fijian medicinal plant Dysoxylumrichii." Canadian Journal of Chemistry 67, no. 2 (1989): 257–60. http://dx.doi.org/10.1139/v89-042.

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Three new limonoids have been isolated from the Fijian medicinal plant Dysoxylumrichii. Dried D. richii leaves collected at Suva yielded the known limonoid dysoxylin (1) as well as the previously unreported dysoxylone (2). A Taveuni collection of leaves contained the two new metabolites tigloyldysoxylin (3) and 6α-acetoxyobacunol acetate (4). The structures of all three new compounds were determined by spectroscopic analysis. Keywords: Dysoxylumrichii, limonoid, dysoxylone, tigloyldysoxylin, 6α-acetoxyobacunol acetate.

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8

Poulose*, Shibu M., Jennifer S. Brodbelt, Leonard M. Pike, and Bhimanagouda S. Patil. "Chromatographic Techniques to Purify Individual Limonoids from Seeds and Molasses of Citrus Fruits." HortScience 39, no. 4 (2004): 752D—752. http://dx.doi.org/10.21273/hortsci.39.4.752d.

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Limonoids, chemically related triterpinoids predominantly found in citrus and neem relatives, are known to play a pivotal role in the prevention of different types of cancer and cardiovascular diseases. Since the concentrations of these compounds are low in the plant tissues, the isolation of pure compounds is the limiting factor for the individual activity studies in animal models. In this study, combinations of chromatographic techniques were used to isolate limonoid aglycones and limonoid glucosides from citrus byproducts such as seeds and molasses. The compounds were initially extracted wi

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9

Oliveira, Iara dos Santos da Silva, Carla Junqueira Moragas Tellis, Maria do Socorro dos Santos Chagas, et al. "Carapa guianensis Aublet (Andiroba) Seed Oil: Chemical Composition and Antileishmanial Activity of Limonoid-Rich Fractions." BioMed Research International 2018 (September 6, 2018): 1–10. http://dx.doi.org/10.1155/2018/5032816.

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Leishmaniasis is a complex of diseases caused by protozoa of the genus Leishmania and affects millions of people around the world. Several species of plants are used by traditional communities for the treatment of this disease, among which is Carapa guianensis Aubl. (Meliaceae), popularly known as andiroba. The objective of the present work was to conduct a chemical study of C. guianensis seed oil and its limonoid-rich fractions, with the aim of identifying its secondary metabolites, particularly the limonoids, in addition to investigating its anti-Leishmania potential. The chemical analyses o

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10

Minamisawa, Mayumi, Takuma Suzumura, Sudeep Bose, et al. "Effect of Yuzu (Citrus junos) Seed Limonoids and Spermine on Intestinal Microbiota and Hypothalamic Tissue in the Sandhoff Disease Mouse Model." Medical Sciences 9, no. 1 (2021): 17. http://dx.doi.org/10.3390/medsci9010017.

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The effect of limonoids and spermine (Spm) extracted from yuzu (Citrus junos) seeds on the gut and the brain in a mouse model with Sandhoff disease (SD) was investigated. Wild-type and SD mice were fed a normal diet, or a diet supplemented with limonoid, Spm, or limonoid + Spm for 14–18 weeks, and then 16S rRNA gene amplicon sequencing with extracted DNA from their feces was executed. For SD control mice, intestinal microbiota was mostly composed of Lactobacillus and linked to dysbiosis. For SD and wild-type mice fed with limonoids + Spm or limonoids alone, intestinal microbiota was rich in mu

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11

Laphookhieo, Surat, Wisanu Maneerat, Sorwaporn Koysomboon, Rattana Kiattansakul, Kan Chantrapromma, and John Keith Syers. "A novel limonoid from the seeds of Chisocheton siamensis." Canadian Journal of Chemistry 86, no. 3 (2008): 205–8. http://dx.doi.org/10.1139/v07-155.

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Analysis of an acetone/hexane (1:1) extract of the seeds of Chisocheton siamensis led to the isolation of a novel limonoid, chisosiamensin (1), along with five known limonoids, dysobinin (2), azadiradione (3), mohinin (4), epoxyazadiradione (5), and 6α-acetoxyepoxyazadiradione (6). Their structures were characterized by spectroscopic methods, including UV, IR, NMR, and MS. All isolated limonoids were reported for the first time as secondary metabolites of C. siamensis.Key words: Chisocheton siamensis, Meliaceae, chisosiamensin, limonoids.

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12

Fu, Shaomin, and Bo Liu. "Recent progress in the synthesis of limonoids and limonoid-like natural products." Organic Chemistry Frontiers 7, no. 14 (2020): 1903–47. http://dx.doi.org/10.1039/d0qo00203h.

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Recent progress in syntheses of limonoids and limonoid-like natural products is reviewed. The current “state-of-art” advance on novel synthetic strategy are summarized and future outlook will be presented.

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13

Hamdan, Dalia, Mahmoud Zaki El-Readi, Ahmad Tahrani, et al. "Secondary Metabolites of Ponderosa Lemon (Citrus pyriformis) and their Antioxidant, Anti-Inflammatory, and Cytotoxic Activities." Zeitschrift für Naturforschung C 66, no. 7-8 (2011): 385–93. http://dx.doi.org/10.1515/znc-2011-7-810.

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Column chromatography of the dichloromethane fraction from an aqueous methanolic extract of fruit peel of Citrus pyriformis Hassk. (Rutaceae) resulted in the isolation of seven compounds including one coumarin (citropten), two limonoids (limonin and deacetylnomilin), and four sterols (stigmasterol, ergosterol, sitosteryl-3-β-D-glucoside, and sitosteryl-6ʹ- O-acyl-3-β-D-glucoside). From the ethyl acetate fraction naringin, hesperidin, and neohesperidin were isolated. The dichloromethane extract of the defatted seeds contained three additional compounds, nomilin, ichangin, and cholesterol. The i

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14

Biavatti, Maique W., Paulo C. Vieira, M. Fatima G. F. da Silva, João B. Fernandes, and Sérgio Albuquerque. "Limonoids from the Endemic Brazilian Species Raulinoa echinata." Zeitschrift für Naturforschung C 56, no. 7-8 (2001): 570–74. http://dx.doi.org/10.1515/znc-2001-7-815.

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Phytochemical survey of stems and leaves of the South Brazilian endemic Raulinoa echinata Cowan, Rutaceae led to the isolation of five limonoid derivatives: the widespread limonin, limonexic acid, kihadalactone B, a methoxylated limonexic acid derivative and a degraded limonoid structurally related to fraxinellone. The two latter compounds have been isolated for the first time. These compounds displayed weak inhibitory activity when assayed in vitro against trypomastigote forms of Trypanosoma cruzi. In this paper, the isolation, structure elucidation and bioactivity of these compounds are repo

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15

Liu, Shengyu, Linping Hu, Dong Jiang, and Wanpeng Xi. "Effect of Post-Harvest LED and UV Light Irradiation on the Accumulation of Flavonoids and Limonoids in the Segments of Newhall Navel Oranges (Citrus sinensis Osbeck)." Molecules 24, no. 9 (2019): 1755. http://dx.doi.org/10.3390/molecules24091755.

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To investigate the effect of post-harvest light irradiation on the accumulation of flavonoids and limonoids, harvested Newhall navel oranges were continuously exposed to light-emitting diode (LED) and ultraviolet (UV) light irradiation for 6 days, and the composition and content of flavonoids and limonoids in the segments were determined using UPLC-qTOF-MS at 0, 6, and 15 days after harvest. In total, six polymethoxylated flavonoids (PMFs), five flavone-O/C-glycosides, seven flavanone-O-glycosides, and three limonoids were identified in the segments. The accumulation of these components was al

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16

Hilmayanti, Erina, Nurlelasari Nurlelasari, Dewa Gede Katja, et al. "Azadirone-Type Limonoids from the Fruit of Chisocheton lasiocarpus and Their Cytotoxic Activity Against MCF-7 Breast Cancer Lines." Molekul 17, no. 1 (2022): 60. http://dx.doi.org/10.20884/1.jm.2022.17.1.5593.

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Limonoid is derivatives of triterpenoid compound that have a wide variety of structures due to various ring-opening, rearrangements, and high-degree of oxidation. Limonoid is known as compounds that have wide-range of biological activities, including anticancer activity. This research was aimed to determine the chemical structure and cytotoxic activity of limonoid in the n-hexane extract of Chisocheton lasiocarpus fruit. Dried powder of C. lasiocarpus fruit was extracted using methanol followed by fractionated using n-hexane, ethyl acetate, and n-butanol. Five azadirone-type limonoids, 6α-(ace

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17

MacLeod, John K., Peter D. R. Moeller, B. M. Ratnayake Bandara, A. A. Leslie Gunatilaka, and E. M. Kithsiri Wijeratne. "Acidissimin, a New Limonoid from Limonia acidissima." Journal of Natural Products 52, no. 4 (1989): 882–85. http://dx.doi.org/10.1021/np50064a040.

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18

Pessoa, Luiz Gustavo Antunes, Leonardo Antunes Pessoa, Éverton da Silva Santos, et al. "Limonoid detection and profile in callus culture of sweet orange." Acta Scientiarum. Biological Sciences 43 (April 19, 2021): e53075. http://dx.doi.org/10.4025/actascibiolsci.v43i1.53075.

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Plant tissue culture has emerged as an important tool to produce bioactive compounds from various plant species, including the sustainable production of limonoids that are receiving considerable attention due to the benefits associated with human health such as anticancer activities. The purpose of the present study was to evaluate the capacity of limonoids aglycone production from callus culture from sweet orange cv. Pera (Citrus sinensis) seeds and identify the compounds produced in this cell line. Callus induction occurred in Murashige and Skoog medium supplemented with 2,4-dichlorophenoxya

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19

Saini, Manpreet Kaur, Neena Capalash, Eldho Varghese, Charanjit Kaur, and Sukhvinder Pal Singh. "A Targeted Metabolomics Approach to Study Secondary Metabolites and Antioxidant Activity in ‘Kinnow Mandarin’ during Advanced Fruit Maturity." Foods 11, no. 10 (2022): 1410. http://dx.doi.org/10.3390/foods11101410.

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In this study, we investigated the impact of harvest maturity stages and contrasting growing climates on secondary metabolites in Kinnow mandarin. Fruit samples were harvested at six harvest maturity stages (M1–M6) from two distinct growing locations falling under subtropical–arid (STA) and subtropical–humid (STH) climates. A high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) technique was employed to identify and quantify secondary metabolites in the fruit juice. A total of 31 polyphenolics and 4 limonoids, with significant differences (p < 0.05) in their concentr

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Khalil, Ashraf T., Galal T. Maatooq, and Khalid A. El Sayed. "Limonoids from Citrus reticulata." Zeitschrift für Naturforschung C 58, no. 3-4 (2003): 165–70. http://dx.doi.org/10.1515/znc-2003-3-403.

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The seeds of Citrus reticulata afforded the new limonoid derivative, isolimonexic acid methyl ether, in addition to the the previously isolated limonin, deacetylnomilin, obacunone and ichangin. The structure elucidation was achieved primarily through 1D and 2-D-NMR analyses. The marginal antimalarial activity of isolimonexic acid methyl ether is reported.

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21

Álvarez-Caballero, Juan Manuel, and Ericsson Coy-Barrera. "Chemical and Antifungal Variability of Several Accessions of Azadirachta indica A. Juss. from Six Locations Across the Colombian Caribbean Coast: Identification of Antifungal Azadirone Limonoids." Plants 8, no. 12 (2019): 555. http://dx.doi.org/10.3390/plants8120555.

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Plant materials (i.e., leaves, fruits, and seeds) from 40 trees of Azadirachta indica A. Juss. were collected from six different locations across the Colombian Caribbean coast. Eighty-four ethanolic extracts were prepared and the total limonoid contents (TLiC) and the antifungal activity against Fusarium oxysporum conidia were measured. Their chemical profiles were also recorded via liquid chromatography-electrospray ionization interface-mass spectrometry (LC-ESI-MS) analysis and the top-ranked features were then annotated after supervised multivariate statistics. Inter-location chemical varia

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22

AYANO, Shigeru, Yoshihiko OZAKI, Nobuya INABA, et al. "Extraction of Limonoids and Limonoid Glucosides with Supercritical Carbon Dioxide." NIPPON SHOKUHIN KOGYO GAKKAISHI 39, no. 8 (1992): 684–89. http://dx.doi.org/10.3136/nskkk1962.39.684.

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23

Nurlelasari, Nurlelasari, Desi Harneti P. Huspa, Rani Maharani, et al. "Nimonol from Chisocheton macrophyllus (Meliaceae) Seeds and Their Cytotoxic Activity against P-388 Leukaemia Cells." Jurnal Kimia Valensi 8, no. 2 (2022): 263–68. http://dx.doi.org/10.15408/jkv.v8i2.27782.

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The Chisocheton genus belongs to the Meliaceae family which produces various structures and activities of compounds, such as antimalarial, antimicrobial, antitumor, anti-inflammatory, and cytotoxic. This plant has 53 species that are spread in tropical and sub-tropical forests, including Indonesia. Chisocheton plants have been known as plants that produce limonoids, namely triterpenoid compounds that have been modified to lose four terminal carbons (tetranortriterpenoids). One of the species whose phytochemical reports are still few and interesting for research on limonoid content is Chisochet

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24

Nadi, Roya, Behrouz Golein, Aurelio Gómez-Cadenas, and Vicent Arbona. "Developmental Stage- and Genotype-Dependent Regulation of Specialized Metabolite Accumulation in Fruit Tissues of Different Citrus Varieties." International Journal of Molecular Sciences 20, no. 5 (2019): 1245. http://dx.doi.org/10.3390/ijms20051245.

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Flavor traits in citrus are the result of a blend of low molecular weight metabolites including sugars, acids, flavonoids and limonoids, these latter being mainly responsible for the characteristic bitter flavor in citrus. In this work, the genotype- and developmental stage-dependent accumulation of flavonoids and limonoids is addressed. To fulfill this goal, three models for citrus bitterness: bitter Duncan grapefruit, bittersweet Thomson orange and sweet Wase mandarin were selected from a total of eight different varieties. Compounds were annotated from LC/ESI-QqTOF-MS non-targeted metabolit

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Vikram, Amit, G. K. Jayaprakasha, and Bhimanagouda S. Patil. "(88) Sour Orange: A Source of Unique Bioactive Limonoid Glucosides." HortScience 41, no. 4 (2006): 1022A—1022. http://dx.doi.org/10.21273/hortsci.41.4.1022a.

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Our recent studies have shown that certain citrus limonoids protect from colon cancer based on cell and animal studies. Animal studies also suggest that citrus juice protects from osteoporosis. To understand the structure–function relationship through animal studies requires a large amount of purified limonoids. Since certain limonoids are present in low concentration, it is a challenge to obtain the required quantity of different limonoids. In this context, we report the purification of limonin 17-ß-D glucopyranosides (LG), and deacetylnomilinic acid 17-ß-D glucopyranoside (DNAG). However, DN

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Widayanti, Setyo, Rudiyansyah Rudiyansyah, and Andi Hairil Alimuddin. "PENENTUAN STRUKTUR SENYAWA ANTIOKSIDAN LIMONOID DARI BIJI JERUK SAMBAL (Citrus microcarpa Bunge) KALIMANTAN BARAT." Indonesian Journal of Pure and Applied Chemistry 1, no. 3 (2019): 77. http://dx.doi.org/10.26418/indonesian.v1i3.34193.

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Limonoid has been isolated from orange seeds of Citrus microcarpa Bunge using extraction and partitioning methods. It is a yellowish-white crystal with a melting point of 276-277 oC. Based on the phytochemical analysis and FTIR spectroscopy, 1H NMR and compared with the literature, the compound is limonin which is a triterpenoid. The purpose of this study was to determine the structure and evaluate antioxidant activity of the limonin. The antioxidant activity by DPPH obtained IC50 value of limonin was 199.18 ppm. Whereas, the test antioxidant activity by FRAP method using a comparative solutio

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Fernández-Mateos, A., P. Herrero Teijón, G. Pascual Coca, R. Rubio González, and M. S. J. Simmonds. "Synthesis of limonoid CDE fragments related to limonin and nimbinim." Tetrahedron 66, no. 36 (2010): 7257–61. http://dx.doi.org/10.1016/j.tet.2010.07.020.

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Matsumoto, Chihiro, Atsushi Koike, Reiko Tanaka, and Ko Fujimori. "A Limonoid, 7-Deacetoxy-7-Oxogedunin (CG-1) from Andiroba (Carapa guianensis, Meliaceae) Lowers the Accumulation of Intracellular Lipids in Adipocytes via Suppression of IRS-1/Akt-Mediated Glucose Uptake and a Decrease in GLUT4 Expression." Molecules 24, no. 9 (2019): 1668. http://dx.doi.org/10.3390/molecules24091668.

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Limonoids are phytochemicals with a variety of biological properties. In the present study, we elucidated the molecular mechanism of suppression of adipogenesis in adipocytes by a limonoid, 7-deacetoxy-7-oxogedunin (CG-1) from Carapa guianensis (Meliaceae), known as andiroba. CG-1 reduced the accumulation of intracellular triglycerides in a concentration-dependent manner. The expression levels of the adipogenic, lipogenic, and lipolytic genes were decreased by CG-1 treatment, whereas the glycerol release level was not affected. When CG-1 was added into the medium during days 0-2 of 6-days-adip

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Ferrera-Suanzes, Marta, Victoria Prieto, Antonio J. Medina-Olivera, et al. "Synthesis of Degraded Limonoid Analogs as New Antibacterial Scaffolds against Staphylococcus aureus." Antibiotics 9, no. 8 (2020): 488. http://dx.doi.org/10.3390/antibiotics9080488.

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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 limon

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Rind, Nadir Ali, Khalid Hussain Rind, Muhammad Umar Dahot, et al. "Production of Limonoids Through Callus and Cell Suspension Cultures of Chinaberry (Melia Azedarach L.)." Bangladesh Journal of Botany 50, no. 2 (2021): 301–9. http://dx.doi.org/10.3329/bjb.v50i2.54086.

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To study the in vitro production of limonoid contents through callus and cell suspension cultures of chinaberry (Melia azedarach L.) in different explants were inoculated in Murashige and Skoog (MS) medium for the callus induction with various plant growth regulators (PGRs) separately as well as in combinations. The highest callus induction (73.3%) was observed in nodular stem sections and further callus was subcultured for multiplication and finally transferred to cell suspension medium. The optimized parameters for the production of total limonoids were adjusted and UV-visible spectrophotome

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Nurhaliza, Nurhaliza Nurhaliza, Rudiyansyah Rudiyansyah, and Harlia Harlia. "PERBANDINGAN METODE EKSTRAKSI TERHADAP KANDUNGAN LIMONIN PADA EKSTRAK METANOL BIJI JERUK SAMBAL (Citrus microcarpa Bunge) (COMPARISON OF EXTRACTION METHODS FOR LIMONIN CONTENT IN METHANOL EXTRACT OF SEEDS OF Citrus microcarpa Bunge)." Indonesian Journal of Pure and Applied Chemistry 5, no. 1 (2022): 20. http://dx.doi.org/10.26418/indonesian.v5i1.53663.

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Limonin is a limonoid compound belonging to a terpenoid and it is found in Citrus plants including in the seeds of C. microcarpa. According to literature, limonin has been isolated by different methods from various Citrus plants with variable concentration. In this study, three extraction methods, maceration, soxhletation, and sonication were compared to examine a limonin concentration from the seeds of C. microcarpa. The purpose of this study is to determine the best extraction method which is able to give the highest concentration of limonin in the methanol extract. On the basis of phytochem

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Byrne, LT, M. Vantri, NM Phuong, MV Sargent, BW Skelton, and AH White. "Perforatin: a Novel Tetranortriterpenoid From Harrisonia perforata." Australian Journal of Chemistry 44, no. 1 (1991): 165. http://dx.doi.org/10.1071/ch9910165.

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Extraction of the dried leaves of Harrisonia perforata (Blanco) Merr ., (Simaroubaceae) has yielded a novel tetranortriterpenoid ( limonoid ), perforatin (1), of the obacunol class. The structure was determined by a combination of spectroscopic analysis and the X-ray method. Comments are made on the stereochemistry of the related limonoid harrisonin.

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Limachi, Ivan, Mariela Gonzalez-Ramirez, Sophie Manner, et al. "Trichilianones A-D, Novel Cyclopropane-Type Limonoids from Trichilia adolfi." Molecules 26, no. 4 (2021): 1019. http://dx.doi.org/10.3390/molecules26041019.

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The fractionation of an ethanol extract of the bark of Trichilia adolfi yielded four novel limonoids (trichilinones A-D, 1–4), with five fused rings and related to the hortiolide-type limonoids. Starting with an ε-lactone, which is α,β-unsaturated in trichilinones A and D (1 and 4), attached to a tetrahydrofuran ring that is connected to an unusual bicyclo [5.1.0] hexane system, joined with a cyclopentanone with a 3-furanyl substituent [(2-oxo)-furan-(5H)-3-yl in trichilinone D (4)], the four compounds isolated display a new 7/5/3/5/5 limonoid ring system. Their structures were established bas

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34

Inoue, Takanobu, Shoko Ohmori, Takashi Kikuchi, Takeshi Yamada, and Reiko Tanaka. "Carapanosins D—F from the Seeds of Andiroba (Carapa guianensis, Meliaceae) and Their Effects on LPS-Activated NO Production." Molecules 23, no. 7 (2018): 1778. http://dx.doi.org/10.3390/molecules23071778.

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A novel nor-phragmalin-type limonoid, named carapanosin D (1), and two novel mexicanolide-type limonoids, carapanosins E (2) and F (3), were isolated from the seed oil of andiroba (Carapa guianensis Aublet), a traditional medicine in Brazil and Latin American countries. Their structures were unambiguously determined on the basis of spectroscopic analyses using one-dimensional (1D) and two-dimensional (2D) NMR techniques and High resolution Fast Atom Bombardment Mass Spectrometry (HRFABMS). Compounds 1–3 were evaluated for their effects on the production of nitric oxide (NO) in Lipopolysacchari

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35

Piyapolrungroj, Nusara, Panadda Phattanawasin, Uthai Sotanaphun, and May Phyu Thein Maw. "Role of Citrus Limonoid as a Possible Bioavailability Enhancer." Key Engineering Materials 859 (August 2020): 132–38. http://dx.doi.org/10.4028/www.scientific.net/kem.859.132.

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The oral delivery is the most practical route to deliver drugs into the body, however drug-metabolizing enzymes and drug transporters can play important roles in modulating drug absorption. This study intended to find a natural bioenhancer for improving drug bioavailability. Two limonoids, including limonin deepoxy and nomilin, isolated from pomelo pulp were studied and the inhibition effects on human CYP3A4 and P-gp were investigated. Testosterone 6β-hydroxylation was performed in recombinant human CYP3A4 to discover the effects on CYP activity. Daunorubicin transport in Caco-2 and calcein-AM

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36

Bentley, Michael D., Mohammed S. Rajab, Michael J. Mendel, and A. Randall Alford. "Limonoid model insect antifeedants." Journal of Agricultural and Food Chemistry 38, no. 6 (1990): 1400–1403. http://dx.doi.org/10.1021/jf00096a022.

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37

Hasegawa, Shin, Raymond D. Bennett, Zareb Herman, Chi H. Fong, and Peter Ou. "Limonoid glucosides in citrus." Phytochemistry 28, no. 6 (1989): 1717–20. http://dx.doi.org/10.1016/s0031-9422(00)97831-2.

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38

Toscano, Rubén A., Rachel Mata, José Calderon, and Rosabel Segura. "Gedunin, ad-seco limonoid." Journal of Chemical Crystallography 26, no. 10 (1996): 707–11. http://dx.doi.org/10.1007/bf01991968.

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39

Bennett, Raymond D., Masaki Miyake, Yoshihiko Ozaki, and Shin Hasegawa. "Limonoid glucosides inCitrus aurantium." Phytochemistry 30, no. 11 (1991): 3803–5. http://dx.doi.org/10.1016/0031-9422(91)80116-i.

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40

Nagatomo, Akifumi, Kiyofumi Ninomiya, Shinsuke Marumoto, et al. "A Gedunin-Type Limonoid, 7-Deacetoxy-7-oxogedunin, from Andiroba (Carapa guianensis Aublet) Reduced Intracellular Triglyceride Content and Enhanced Autophagy in HepG2 Cells." International Journal of Molecular Sciences 23, no. 21 (2022): 13141. http://dx.doi.org/10.3390/ijms232113141.

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The seed oil of Carapa guianensis Aublet (Andiroba) has been used in folk medicine for its insect-repelling, anti-inflammatory, and anti-malarial activities. This study aimed to examine the triglyceride (TG) reducing effects of C. guianensis-derived limonoids or other commercially available limonoids in human hepatoblastoma HepG2 cells and evaluate the expression of lipid metabolism or autophagy-related proteins by treatment with 7-deacetoxy-7-oxogedunin (DAOG; 1), a principal limonoid of C. guianensis. The gedunin-type limonoids, such as DAOG (% of control at 20 μM: 70.9 ± 0.9%), gedunin (2,

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41

Bruss, Hanna, Hannah Schuster, Rémi Martinez, Markus Kaiser, Andrey P. Antonchick, and Herbert Waldmann. "Synthesis of the B-seco limonoid core scaffold." Beilstein Journal of Organic Chemistry 10 (January 16, 2014): 194–208. http://dx.doi.org/10.3762/bjoc.10.15.

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Synthetic investigations towards the structurally complex and highly decorated framework of B-seco limonoid natural products by means of a [3,3]-sigmatropic rearrangement are described. Detailed model studies reveal, that an Ireland–Claisen rearrangement can be employed to construct the central C9–C10 bond thereby giving access to the B-seco limonoid scaffold. However, application of the developed strategy ended up failing in more complex and sterically demanding systems.

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42

Tsamo, Armelle Tontsa, Julio Issah Mawouma Pagna, Pamela Kemda Nangmo, Pierre Mkounga, Hartmut Laatsch, and Augustin Ephrem Nkengfack. "Rubescins F–H, new vilasinin-type limonoids from the leaves of Trichilia rubescens (Meliaceae)." Zeitschrift für Naturforschung C 74, no. 7-8 (2019): 175–82. http://dx.doi.org/10.1515/znc-2018-0187.

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Abstract Three new limonoids, designated as rubescins F (1), G (2), and H (3), together with two known compounds of this type, TS1 (4) and trichirubine A (5), were isolated from methylene chloride/methanol extracts of Trichilia rubescens leaves. The structures of these compounds were elucidated based on 1D and 2D nuclear magnetic resonance (NMR) analysis and complemented by electrospray ionization high-resolution mass spectrometry results and by comparison to data of related compounds described in the literature and ab initio calculations. Rubescin F (1) is the first limonoid from Trichilia sp

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43

Pandreka, Avinash, Patil S. Chaya, Ashish Kumar, et al. "Limonoid biosynthesis 3: Functional characterization of crucial genes involved in neem limonoid biosynthesis." Phytochemistry 184 (April 2021): 112669. http://dx.doi.org/10.1016/j.phytochem.2021.112669.

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44

OZAKI, Yoshitake, Chi H. FONG, Zareb HERMAN, et al. "Limonoid glucosides in citrus seeds." Agricultural and Biological Chemistry 55, no. 1 (1991): 137–41. http://dx.doi.org/10.1271/bbb1961.55.137.

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45

Ozaki, Yoshihiko, Chi H. Fong, Zareb Herman, et al. "Limonoid Glucosides in Citrus Seeds." Agricultural and Biological Chemistry 55, no. 1 (1991): 137–41. http://dx.doi.org/10.1080/00021369.1991.10870551.

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46

HASEGAWA, SHIN, CHI H. FONG, MASAKI MIYAKE, and JAMES H. KEITHLY. "Limonoid glucosides in Orange Molasses." Journal of Food Science 61, no. 3 (1996): 560–61. http://dx.doi.org/10.1111/j.1365-2621.1996.tb13157.x.

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Cortez, Diógenes A. G., João B. Fernandes, Paulo C. Vieira, M. Fátima das G.F da Silva, and A. Gilberto Ferreira. "A limonoid from Trichilia estipulata." Phytochemistry 55, no. 7 (2000): 711–13. http://dx.doi.org/10.1016/s0031-9422(00)00298-3.

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Hassanali, A., M. D. Bentley, E. N. Ole Sitayo, P. E. W. Njoroge, and M. Yatagai. "Studies on limonoid insect antifeedants." International Journal of Tropical Insect Science 7, no. 04 (1986): 495–99. http://dx.doi.org/10.1017/s1742758400009711.

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Randrianarivelojosia, Milijaona, Maria P. Kotsos, and Dulcie A. Mulholland. "A limonoid from Neobeguea mahafalensis." Phytochemistry 52, no. 6 (1999): 1141–43. http://dx.doi.org/10.1016/s0031-9422(99)00290-3.

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Mulholland, Dulcie A., Milijaona Randrianarivelojosia, Catherine Lavaud, Jean-Marc Nuzillard, and Sianne L. Schwikkard. "Limonoid derivatives from Astrotrichilia voamatata." Phytochemistry 53, no. 1 (2000): 115–18. http://dx.doi.org/10.1016/s0031-9422(99)00488-4.

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