• Natural Product Sciences
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• v.6 no.4
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• pp.179-182
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• 2000

Nine compounds were isolated from the fruit Citrus junos. Their structures were elucidated as 9-hydroxy-4-methoxypsoralen, auraptene, limonin, deacetylnomilin, cirsimaritin, narirutin, naringin, hesperidin and neohesperidin by physico-chemical evidences. 9-Hydroxy-4-methoxypsoralen and auraptene have not been reported from C. junos yet.

• Korean Journal of Pharmacognosy
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• v.27 no.1
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• pp.47-52
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• 1996

A triterpenoid(melianone) and a limonoid(28-deacetyl sendanin) were isolated from the chloroform fraction of Meliae toosendan Fructus, the rippen fruits of Melia toosendan SIEB. et ZUCC.(Meliaceae) and were applied to serial experiments to clarify the liver protective activities. We found that the compounds promoted slightly the drug metabolizing enzyme activities and decreased serum transaminase activities which was elevated by carbon tetrachloride intoxication. And also they slightly increased the secretion of bile juice in rat.

• Journal of Applied Biological Chemistry
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• v.48 no.2
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• pp.93-96
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• 2005

Three limonoids and two phenolics were isolated from stem bark of Pellodendron amurense Rupr. (Rutaceae) and were defined clearly as calodendrolide (1), obacunone (2), limonin (3), methyl 4-hydroxybenzoate (4), and syringin (5) based on NMR spectroscopy results obtained with the aid of X-ray crystallographic analysis. This is the first report on the isolation of calodendrolide (1) from this plant.

• Natural Product Sciences
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• v.29 no.1
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• pp.17-23
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• 2023

A phytochemical investigation of the fruits extract of Melia toosendan afforded the isolation of two new nor-neolignans, meliasendanins E (1) and F (2), as well as twelve known compounds (3 - 14) using various separation technique such as Diaion HP20, silica, RP-18 gel column chromatography and semi-preparative HPLC. Their chemical structures were elucidated by extensive NMR spectroscopic data including 2D-NMR, and HR-ESI-MS as well as ECD data. Among the twelve known compounds, the absolute structures of 3 - 6 were determined first, and given the trivial names as meliasendanins G-J (3 - 6). Based on the evaluation of anti-inflammatory activity, compounds 7 - 8 exhibited inhibitory effects on LPS-induced nitric oxide production in RAW 264.7 macrophages with IC₅₀ values of 34.6 and 39.5 µM, respectively.

• Applied Biological Chemistry
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• v.50 no.3
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• pp.238-243
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• 2007

The contents of limonin, nomilin and limonin glucoside in different tissues of dangyuja (Citrus spp.) were measured during fruit growth and maturation by liquid chromatography-mass spectrometry(LC-MS). Both nomilin and limonin contents increased from June, peaked in October and in December, respectively, and then decreased afterwards. In contrast, the content of limonin glucoside increased from October and remained at high levels throughout the maturation. The contents of limonin, nomilin and limonin glucoside in peel decreased gradually throughout the growth and the trends of changes were similar to each other. However, all three limonoid contents in juice sac increased dramatically at the end of fruit maturation. The highest concentration of limonin and nomilin was observed in seed, followed by segment membrane, whereas the highest limonin glucoside concentration was observed in segment membrane, followed by juice sac.

• Food Science and Biotechnology
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• v.17 no.2
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• pp.373-378
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• 2008

Contents of phytochemicals in citron (Citrus junos Sieb. ex Tanaka) seeds and their effects on antioxidant activities were investigated. Methanol extract of defatted citron seeds contained the highest amounts of total polyphenols followed by 70% ethanol and water extracts. Neohesperidin was the most predominant citrus flavanones in these extracts. The highest amounts of limonoids were found in methanol extract, and this extract was the most efficient in scavenging both DPPH and ABTS radicals. All 3 extracts also exhibited good antioxidant activities against attack of linoleate free radicals on $\beta$-carotene. When methanol extract was sequentially fractionated into ether, ethyl acetate, n-butanol, and water fractions, butanol fraction contained the highest amounts of polyphenols otherwise most of limonoids were concentrated in ethyl acetate fraction. A positive relationship between radical scavenging activities and total polyphenol contents in fractions was observed while antioxidant activity on $\beta$-carotene seemed more related with contents of limonoids and other hydrophobic polyphenols.

• Preventive Nutrition and Food Science
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• v.18 no.3
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• pp.196-202
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• 2013

Citron seed extracts (CSEs) were made using distilled water (CSEW), ethanol (CSEE), and n-hexane (CSEH), to measure the total polyphenol contents, DPPH and ABTS radical scavenging activities, and anti-complementary activity. The total polyphenol content was observed the highest in CSEE (188.71 ${\mu}g/mL$), and occurred in the following order: CSEE>CSEW (141.11 ${\mu}g/mL$)>CSEH (26.19 ${\mu}g/mL$) at 10 mg/mL. CSEE (63.56%) and CSEW (56.61%) showed significantly higher DPPH radical scavenging activities when compared with CSEH (28.57%). ABTS radical scavenging activities of CSEE (45.53%) and CSEW (40.02%) were also observed to be higher, whereas CSEH did not show ABTS radical scavenging activity. Anti-complementary activity of CSEE (26.85%) showed a greater activity than that of CSEW (7.84%) at 1,000 ${\mu}g/mL$. Limonin and nomilin contents had the highest values (1.882% and 2.089%) in CSEE, and with 0.327% and 0.139% in CSEW; however, CSEH showed relatively very low values at 0.061% and 0.026%, respectively. Among the CSEs tested, CSEE as a by-product from citron may provide an important source of dietary antioxidant compounds with rich polyphenol and limonoid contents, and immunopotentiating activity, including the complement activation factor.

• The Korean Journal of Pesticide Science
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• v.19 no.2
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• pp.88-92
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• 2015

This study investigated the thermal stabilities of the four limonoidal active compounds like azadirachtin A, azadirachtin B, deacetylsalannin and salannin and of the two alkaloidal active compounds like matrine and oxymatrine in commercial biopesticides at incubated conditions ($30^{\circ}C$, $35^{\circ}C$, $40^{\circ}C$, $45^{\circ}C$, and $54^{\circ}C$). Half-lives of the limonoidal compounds in biopesticide ranged from 25.6 to 220 days. And the total limonoid contents changed over 15% after 14 days at all the conditions in the tested biopesticide containing neem extract. On the contrary, half-lives of the alkaloidal compounds in biopesticide showed the ranges from 231 to 346 days. And total alkaloidal compounds in all the tested biopesticides containing Sophora flavescens extracts decomposed below 15% after 14 days incubation at $54^{\circ}C$.

• Proceedings of the Plant Resources Society of Korea Conference
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• 2019.04a
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• pp.33-33
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• 2019

The AKT signaling pathway is a highly regulated cell signaling system that forms a network with other cell signaling pathways. Hence, the AKT signaling pathway mediates several important cellular functions that include cell survival, proliferation, cell migration, and et cetera. Irregularities that led overactive AKT signaling have been linked to many diseases such as cancer and metabolic-associated diseases. Hence, modulating the overactive AKT signaling pathway via inhibitor is a tantalizing prospect for treatment of cancer and metabolic-associated diseases. Two inhibitors of the AKT signaling pathway will be presented in this symposium: 1) Bisleuconothine A (BisA), a bisindole alkaloid that inhibit autophagy and 2) Ceramicine B (CerB), a limonoid that inhibit adipogenesis. The first topic is on a bisindole alkaloid, BisA and its mechanism in inducing autophagosome formation in lung cancer cell line, A549.(1) Since most autophagy inducing agents generally induce apoptosis, we found that BisA does not induce apoptosis even in high dose. BisA up-regulation of LC3 lipidation is achieved through mTOR inactivation. The phosphorylation of PRAS40, a mTOR repressor was suppressed by BisA. This observation suggested that BisA inactivates mTOR via suppression of PRAS40 phosphorylation. Interestingly, the phosphorylation of AKT, an upstream regulator of PRAS40 phosphorylation was also down-regulated by BisA. These findings suggested that Bis-A induces autophagosomes formation by interfering with the AKT-mTOR signaling pathway. The second topic is on CerB and its mechanism in inhibiting adipogenesis in preadipocytes cell line, MC3T3-G2/PA6.(2,3) CerB inhibits the phosphorylation of protein kinase B (AKT) at the Thr308 position but not the Ser473. Consequently, the phosphorylation of FOXO3 which is located downstream of AKT is also inhibited. Considering that FOXO3 is an important regulator of PPARγ which is a key factor in adipogenesis, CerB may inhibit adipogenesis via the AKT-FOXO3 signaling pathway. Taken together, both BisA and CerB highlighted the potential of AKT signaling pathway modulation as an approach to induce autophagy and inhibit the formation of fat cells, respectively.

• Journal of Plant Biotechnology
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• v.48 no.4
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• pp.289-303
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• 2021

Covid-19 is an ongoing pandemic as we speak in 2022. This infectious disease is caused by the SARS-CoV-2 virus, which infects cells by binding to the angiotensin-converting enzyme 2 (ACE2) receptor on the cell surface. Thus, strategies that inhibit the binding of SARS-CoV-2 to the ACE2 receptor can stop this contagion. Hanjeli (Coix lacryma-jobi) essential oil contains many bioactive compounds, including dodecanoic acid; tetradecanoic acid; 7-Amino-8-imino-2-(2-imino-2H-chromen-3-yl); and 1,5,7,10-tetraaza-phen-9-one. These compounds suppress viral replication and may prevent Covid-19. Accordingly, this study assessed whether, these four limonoid compounds can block the ACE2 receptor. To this end, their physicochemical properties were predicted using Lipinski's "rule of five" on the SwissADME website, and their toxicity was assessed using the online tools ProTox and pkCSM. Additionally, their interactions with the ACE2 receptor were predicted via molecular docking using Autodock Vina. All the four compounds satisfied the "rule of five" and tetradecanoic acid was predicted to have a higher affinity than the comparison compound remdesivir and the original ligand of ACE2. Molecular docking results suggested that the compounds from hanjeli essential oil interact with the active site of the ACE2 receptor similarly as the original ligand and remdesivir. In conclusion, hanjeli essential oil contains compounds predicted hinder the interaction of SARS-CoV-2 with the ACE2 receptor. Accordingly, our data may facilitate the development of a phytomedical strategy against SARS-CoV-2 infection.