• Natural Product Sciences
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• 제6권4호
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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.

• 생약학회지
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• 제27권1호
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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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• 제48권2호
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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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• 제29권1호
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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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• 제50권3호
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• pp.238-243
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• 2007

Limonoid계 화합물인 limonin, nomilin, limonin glucoside의 함량을 당유자 과실의 성숙시기별 조직부위별로 liquid chromatography-mass spectrometry(LC-MS)를 이용하여 정량하였다. Nomilin과 limonin의 함량은 6월 미성숙기부터 증가하였으며 nomilin은 10월 성숙기, limonin은 12월 성숙후기에서 그 함량이 최고치를 나타냈으며, 두 가지 화합물 모두 3월 완숙후기에는 함량이 현저하게 감소하였다. 이와 대조적으로 limonin glucoside 함량은 10월 성숙기부터 완숙 후기에 이르기까지 지속적으로 증가하였다. 세 가지 성분 모두 과실이 완숙함에 따라 peel에서의 함량은 감소하는 경향을 보인 반면, juice sac에서의 함량은 증가하는 경향을 보였다. 완숙후기에 채취한 당유자 과실의 조직부위별 limonin, nomilin 및 limonin glucoside의 함량을 분석한 결과, limonin과 nomilin은 씨앗에서 함량이 가장 높게 나타났고, 다음으로는 segment membrane가 높게 나타났다. 반면 limonin glucoside는 segment membrane에서 함량이 가장 높은 것으로 확인되었으며, 그 다음은 juice sac에서 함량이 높게 나타났다.

• Food Science and Biotechnology
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• 제17권2호
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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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• 제18권3호
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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.

• 농약과학회지
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• 제19권2호
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• pp.88-92
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• 2015

님 추출물 또는 고삼 추출물을 주원료로 하는 유기농업자재의 유효성분인 limonoid계 4성분 (azadirachtin A, azadirachtin B, deacetylsalannin, salannin)과 alkaloid계 2성분 (matrine, oxymatrine)을 중심으로 열 안정성을 평가하였다. 시험은 $30^{\circ}C$, $35^{\circ}C$, $40^{\circ}C$, $45^{\circ}C$, $54^{\circ}C$에서 각각 진행하였으며, 님 추출물을 주성분으로 하는 유기농업자재 3종에서 유효성분 반감기는 25.6-220일로 제품에 따라 열 안정성의 차이가 큰 것을 확인하였다. 반면, 고삼 추출물을 주성분으로 하는 유기농업자재의 유효성분 반감기는 231-346일로 님 추출물에 비해 상대적으로 열 안정성이 높은 것으로 나타났다.

• 한국자원식물학회:학술대회논문집
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• 한국자원식물학회 2019년도 춘계학술대회
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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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• 제48권4호
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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.