• 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.

• Korean Journal of Pharmacognosy
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• v.44 no.1
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• pp.6-9
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• 2013

Two fraxinellone-based hydrogenated derivatives were prepared from fraxinellone, a well-known degraded limonin, via catalytic hydrogenation in the presence of $PtO_2$ in HOAc. Their structures were confirmed as (3S,3aR,3'R)-3a,7-dimethyl-3-(tetrahydrofuran-3-yl)-3a,4,5,6-tetrahydroisobenzofuran-1(3H)-one and (3S,3aR,2'R)-3-((R)-1-hydroxybutan-2-yl)-3a,7-dimethyl-3a,4,5,6-tetrahydroisobenzofuran-1(3H)-one on the basis of 2D NMR assignments. The $^{13}C$ NMR assignments of two quaternary carbons in the ${\alpha}$,${\beta}$-unsaturated carbonyl moiety of ${\gamma}$-butyrolactone core of fraxinellone should be revised.

• Natural Product Sciences
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• v.26 no.2
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• pp.176-181
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• 2020

Two new compounds, 3-methyl-but-2-en-1-yl-1-O-β-xylopyranosyl-(1"→2')-O-β-glucopyranoside (1) and 1-O-β-glucopyranosyl-6-hydroxy-2-methyl-hep-2-enoic acid (2), along with sixteen known terpenoids were isolated from the peels of Citrus unshiu Markov. Their structures were elucidated based on extensive NMR analyses (¹H NMR, ¹³C NMR, DEPT, COSY, HMQC, and HMBC) and high-resolution mass spectrometry. In addition, all isolates (1 - 18) were tested their effects on nitric oxide (NO) production in RAW264.7 cells. Limonin (15) showed to inhibit LPS-induced NO production in a concentration-dependent manner without cytotoxicity.

• Korean Journal of Pharmacognosy
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• v.43 no.2
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• pp.122-126
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• 2012

The MeOH extract of Evodiae Fructus exhibited a significant inhibition on the acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), in a dose dependent manner, respectively. The extensive bioactivity-guided fractionation process with the MeOH extract finally isolated four compounds, as rutaecarpine (1), evodiamine (2), limonin (3) and dehydroevodiamine (4). Among them, compound 2 exhibited specific inhibitory activity on BChE with the $IC_{50}$ values 1.7 ${\mu}g/ml$, whereas compound 4 showed the potent inhibition upon both AChE and BChE.

• Archives of Pharmacal Research
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• v.25 no.6
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• pp.824-830
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• 2002

Four flavonoid glycosides, flavaprin (7), evodioside B (8), vitexin (11), and hesperidin (12), as well as the coumarins bergapten (1), xanthotoxin (2), and isopimpinellin (3), the lignan simplexoside (10), the steroids ${\beta}-sitosterol$ (4) and daucosterol (5), the limonoids isolimonexic acid (6) and limonin (9), and uracil (13) and myo-inositol (14) have been isolated from Euodia daniellii. The structures of these compounds were established from spectral data. Among the isolates, bergapten showed cyclooxygenase-2 inhibitory activity with an $IC_{50}$ value of $6.2{\;}{\mu\textrm{g}}/ml. Flavonoids isolated from this plant exhibited no cytotoxic activity against the human tumor cell lines, A549, SKOV-3, SKMEL-2, XF498, and HCT15.

• Food Science and Biotechnology
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• v.18 no.5
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• pp.1224-1229
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• 2009

The main objective of this study was to investigate possible application of citron (Citrus junos Sieb. ex TANAKA) seeds, which are massively produced as by-products during citron tea process, into functional food materials. First of all, citron seeds were germinated and produced citron shoots were examined for their functional properties. When contents of flavonoids in citron seeds and their germinated shoots were compared, naringenin, neohesperitin, and hesperitin were remarkably increased in shoots after germination while naringin and didymin were decreased. Concentrations of limonin and nomilin were decreased by germination otherwise their unidentified derivatives were newly formed. A methanol extract of citron shoot had lower $IC_{50}$ values [0.13 and 0.07 mg/mL for 2,2-diphenyl-1-picryl-hydrazyl (DPPH) and ABTS, respectively] than citron seed extract in radical scavenging activities. Addition of 500 mg/mL of citron shoot extract suppressed fat accumulation in 3T3-L1 adipocytes by 36.9%. Oral administration of olive oil along with citron shoot extract (33 mg/kg body weight) to Sprague Dawley rats effectively inhibited absorption of lipid into a body by decreasing blood triglyceride levels from 105.1 to 74.9 mg/dL 2 hr after olive oil administration. According to these results, citron shoot extract as a rich source of flavonoids can be utilized for functional food ingredients with effective antioxidant and anti-adipogenic properties.

• 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.

• Applied Biological Chemistry
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• v.48 no.1
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• pp.1-15
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• 2005

Pathogens, insects and weeds have significantly reduced agricultural productivity. Thus, to increase the productivity, synthetic agricultural chemicals have been overused. However, these synthetic compounds that are different from natural products cannot be broken down easily in natural systems, causing the destruction of soil quality and agricultural environments and the gradually difficulty in continuous agriculture. Now agriculture is faced with the various problems of minimizing the damage in agricultural environments, securing the safety of human health, while simultaneously increasing agricultural productivity. Meanwhile, plants produce secondary metabolites to protect themselves from external invaders and to secure their region for survival. Plants infected with pathogens produce antibiotics phytoalexin; monocotyledonous plants produce flavonoids and diterpenoids phytoalexins, and dicotylodoneous plant, despite of infected pathogens, produce family-specific phytoalexin such as flavonoids in Leguminosae, indole derivatives in Cruciferae, sesquitepenoids in Solanaceae, coumarins in Umbelliferae, making the plant resistant to specific pathogen. Growth inhibitor or antifeedant substances to insects are terpenoids pyrethrin, azadirachtin, limonin, cedrelanoid, toosendanin and fraxinellone/dictamnine, and terpenoid-alkaloid mixed compounds sesquiterpene pyridine and norditerpenoids, and azepine-, amide-, loline-, stemofoline-, pyrrolizidine-alkaloids and so on. Also plants produces the substances to inhibit other plant growths to secure the regions for plant itself, which is including terpenoids essential oil and sesquiterpene lactone, and additionally, benzoxazinoids, glucosinolate, quassinoid, cyanogenic glycoside, saponin, sorgolennone, juglone and lots of other different of secondary metabolites. Hence, phytoalexin, an antibiotic compound produced by plants infected with pathogens, can be employed for pathogen control. Terpenoids and alkaloids inhibiting insect growth can be utilized for insect control. Allelochemicals, a compound released from a certain plant to hinder the growth of other plants for their survival, can be also used directly as a herbicides for weed control as well. Therefore, the use of the natural secondary metabolites for pest control might be one of the alternatives for environmentally friendly agriculture. However, the natural substances are destroyed easily causing low the pest-control efficacy, and also there is the limitation to producing the substances using plant cell. In the future, effects should be made to try to find the secondary metabolites with good pest-control effect and no harmful to human health. Also the biosynthetic pathways of secondary metabolites have to be elucidated continuously, and the metabolic engineering should be applied to improve transgenics having the resistance to specific pest.

• Food Science and Preservation
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• v.11 no.3
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• pp.417-423
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• 2004

Botanical antimicrobial agent-grapefruit seed extract mixture (BAAG) have an unknown compounds which exhibit the antibiotic activities aganist microorganisms including bacteria and fungi. We have examined the effects of BAAG on the physiological function of Botrytis cinerea which was isolated from necrotic lesions of decayed fruits and vegetables such as cucumbers, grapes, tomatoes, and red peppers during storage. In the results of enzymatic activities related to the energetic metabolism there was no inhibitory effect of BAAG on the activities of several enzymes in vitro including glucose 6-phosphate dehydrogenase and malate dehydrogenase, while there was inhibitory effect of BAAG on the activities of hexokinase and succinate dehydrogenase. O-nitrophenyl-$\beta$-D-galactopyranoside(ONPG), the artificial substrate of $\beta$-galactosidase was hydrolyzed in the presence of BAAG, indicating that the membrane was pertubated by the BAAG. From the results we suggested that the antibiotic activity of BAAG is due to the change of membrane permeability of the cell. BAAG was fractionated and purified by silica gel and sephadex column chromatography. Among active fractions two peaks were identified as naringin and limonin when they were analyzed by by NMR and Fast atomic bombardment.