• Analytical Science and Technology
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• v.34 no.4
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• pp.172-179
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• 2021

Oleanane-type triterpenoids exist as secondary metabolites in various plants. In particular, soyasaponin, an oleanane-type triterpenoid, is abundant in the hypocotyl of soybean, one of the most widely cultivated crops in the world. Depending on their chemical structure, soyasaponins are categorized as group A saponins or group DDMP (2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one) saponins. The different soyasaponin chemical structures present different health functionalities and taste characteristics. However, conventional phenotype screening of soybean requires a substantial amount of time for functionality of soyasaponins. Therefore, we attempted to use liquid chromatography with a photodiode array detector and tandem mass spectrometry (LC-PDA/MS/MS) for accurately predicting the phenotype and chemical structure of soyasaponins in the hypocotyl of five common soybean natural mutants. In this method, the aglycones (soyasapogenol A [SS-A] and soyasapogenol B [SS-B]) were detected after acid hydrolysis. These results indicated that the base peak and fragmentation differ depending on the chemical structure of soyasaponin with aglycone. Thus, a fragmentation database can help predict the chemical structure of soyasaponins in soyfoods and plants.

• Proceedings of the Plant Resources Society of Korea Conference
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• 2020.12a
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• pp.14-14
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• 2020

In December 2019, the COVID-19 epidemic was discovered in Wuhan, China, and since has disseminated around the world impacting human health for millions. Herein, in-silico drug discovery approaches were utilized to identify potential candidates as Severe Acute Respiratory Syndrome coronavirus 2 (SARS-CoV-2) main protease (M^pro) inhibitors. We investigated several databases including natural and natural-like products (>100,000 molecules), DrugBank database (10,036 drugs), major metabolites isolated from daily used spices (32 molecules), and current clinical drug candidates for the treatment of COVID-19 (18 drugs). All tested compounds were prepared and screened using molecular docking techniques. Based on the calculated docking scores, the top ones from each project under investigation were selected and subjected to molecular dynamics (MD) simulations followed by molecular mechanics-generalized Born surface area (MM-GBSA) binding energy calculations. Combined long MD simulations and MM-GBSA calculations revealed the potent compounds with prospective binding affinities against M^pro. Structural and energetic analyses over the simulated time demonstrated the high stabilities of the selected compounds. Our results showed that 4-bis([1,3]dioxolo)pyran-5-carboxamide derivatives (natural and natural-like products database), DB02388 and Cobicistat (DB09065) (DrugBank database), salvianolic acid A (spices secondary metabolites) and TMC-310911 (clinical-trial drugs database) exhibited high binding affinities with SARS-CoV-2 M^pro. In conclusion, these compounds are up-and-coming anti-COVID-19 drug candidates that warrant further detailed in vitro and in vivo experimental estimations.

• Journal of Microbiology and Biotechnology
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• v.27 no.4
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• pp.785-790
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• 2017

Two piloquinone derivatives isolated from Streptomyces sp. CNQ-027 were tested for the inhibitory activities of two isoforms of monoamine oxidase (MAO), which catalyzes monoamine neurotransmitters. The piloquinone 4,7-dihydroxy-3-methyl-2-(4-methyl-1-oxopentyl)-6H-dibenzo[b,d]pyran-6-one (1) was found to be a highly potent inhibitor of human MAO-B, with an $IC_{50}$ value of $1.21{\mu}M$; in addition, it was found to be highly effective against MAO-A, with an $IC_{50}$ value of $6.47{\mu}M$. Compound 1 was selective, but not extremely so, for MAO-B compared with MAO-A, with a selectivity index value of 5.35. Compound 1,8-dihydroxy-2-methyl-3-(4-methyl-1-oxopentyl)-9,10-phenanthrenedione (2) was moderately effective for the inhibition of MAO-B ($IC_{50}=14.50{\mu}M$) but not for MAO-A ($IC_{50}$ > $80{\mu}M$). There was no time-dependency in inhibition of MAO-A or -B by compound 1, and the MAO-A and -B activities were almost completely recovered in the dilution experiments with an excess amount of compound 1. Compound 1 showed competitive inhibition for MAO-A and -B, with $K_i$ values of 0.573 and $0.248{\mu}M$, respectively. These results suggest that piloquinones from a microbial source could be potent reversible MAO inhibitors and may be useful lead compounds for developing MAO enzyme inhibitors to treat related disorders, such as depression, Parkinson's disease, and Alzheimer's disease.

• KOREAN JOURNAL OF CROP SCIENCE
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• v.48
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• pp.49-57
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• 2003

There is much evidence suggesting that compounds present in soybean can prevent cancer in many different organ systems. Especially, soybean is one of the most important source of dietary saponins, which have been considered as possible anticarcinogens to inhibit tumor development and major active components contributing to the cholesterol-towering effect. Also they were reported to inhibit of the infectivity of the AIDS virus (HIV) and the Epstein-Barr virus. The biological activity of saponins depend on their specific chemical structures. Various types of triterpenoid saponins are present in soy-bean seeds. Among them, group B soyasaponis were found as the primary soyasaponins present in soybean, and th e 2, 3-dihydro-2, 5-dihydroxy-6- methyl-4H-pyran-4-one(DDMP)-conjugated soyasaponin $\alpha\textrm{g}$, $\beta\textrm{g}$, and $\beta$ a were the genuine group B saponins, which have health benefits. On the other hand, group A saponins are responsible for the undesirable bitter and astringent taste in soybean. The variation of saponin composition in soybean seeds is explained by different combinations of 9 alleles of 4 gene loci that control the utilization of soyasapogenol glycosides as substrates. The mode of inheritance of saponin types is explained by a combination of co-dominant, dominant and recessive acting genes. The funtion of theses genes is variety-specific and organ specific. Therefore distribution of various saponins types was different according to seed tissues. Soyasaponin $\beta\textrm{g}$ was detected in both parts whereas $\alpha\textrm{g}$ and $\beta$ a was detected only in hypocotyls and cotyledons, respectively. Soyasaponins ${\gamma}$g and $\gamma\textrm{g}$ were minor saponin constituents in soybean. In case group A saponins were mostly detected in hypocotyls. Also, the total soyasaponin contents varied among different soy-bean varieties and concentrations in the cultivated soy-beans were 2-fold lower than in the wild soybeans. But the contents of soyasaponin were not so influenced by environmental effects. The composition and concentration of soyasaponins were different among the soy products (soybean flour, soycurd, tempeh, soymilk, etc.) depending on the processing conditions.

• Asian Pacific Journal of Cancer Prevention
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• v.17 no.2
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• pp.615-618
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• 2016

Ethyl acetate extracts obtained from culture of endophytic fungi Aspergillus sp isolated from Piper crocatum Ruiz & Pav, have been shown to possess cytotoxic activity against T47D breast cancer cells. Investigations were here conducted to determine bioactive compounds responsible for the activity. Bioassay guided fractionation was employed to obtain active compounds. Structure elucidation was performed based on analysis of LC-MS, $^1H$-NMR, $^{13}C$-NMR, COSY, DEPT, HMQC, HMBC data. Cytotoxity assays were conducted in 96 well plates against T47D and Vero cell lines. Bioassay guided isolation and chemical investigation led to the isolation of pyrophen, a 4-methoxy-6-(1'-acetamido-2'-phenylethyl)-2H-pyran-2-one. Further analysis of its activity against T47D and Vero cells showed an ability to inhibit the growth of T47D cells with IC50 values of $9.2{\mu}g/mL$ but less cytotoxicity to Vero cells with an $IC_{50}$ of $109{\mu}g/mL$. This compound at a concentration of 400 ng/mL induced S-phase arrest in T47D cells.

• 한국정보디스플레이학회:학술대회논문집
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• 2005.07b
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• pp.1416-1418
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• 2005

A new DCM derivative containing a phenothiazine moiety, 4-(dicyanomethylene)-2-t-butyl-6-(9-ethylphenothiazine-2- enyl)-4H-pyran (DCPTZ), has been synthesized as an orange-red fluorescent dye molecule for organic lightemitting diodes (OLEDs). EL devices with the structure of $ITO/PEDOT-PSS/{\alpha}-NPD/Alq_3:DCPTZ/Alq_3/LiF/Al$ have been fabricated with changing the doping concentration of the DCPTZ. Maximum EL spectra of the devices ranged from $580{\sim}620$ nm depending on the doping concentration of the dye molecule. An EL device with 0.5 % doping concentration showed CIE coordinate (0.51, 0.47) at luminance of 100 $cd/m^2$. White light-emitting devices with the structure of $ITO/PEDOT-PSS/{\alpha}-NPD/{\alpha}-NPD:DCPTZ/DPVBi/Alq_3/$ LiF/Al have been also fabricated. The thickness of blue light-emitting 1,4-bis(2,2- diphenylvinyl)benzene (DPVBi) layer was changed to obtain a white light-emission. A white light-emission from the device was observed when the thickness of the DPVBi layer became thicker than 10 nm.

• Korean Journal of Pharmacognosy
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• v.17 no.2
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• pp.153-160
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• 1986

We have isolated two new metabolites of territrem, designated as territrem $A'\;(TRA';\;C_{28}H_{30}O_{10})$ and $B'\;(TRB';\; C_{29}H_{34}O_{10})$ from chloroform extract of rice culture of Aspergillus terreus 23-1, using the same isolation procedure as that for territrem A, B and C(TRA, TRB, TRC). The present isolation procedure gave about 5 mg of TRA' and 10 mg of TRB' from 4 kg of rice culture per batch. Analysis of the high resolution mass spectrum showed that the molecular composition of TRA' and TRB' are $C_{28}H_{30}O_{10}$ and $C_{29}H_{34}O_{10}$ respectively, Some results of physicochemical properties were presented in this paper. Single crystal X-ray diffractometry of TRB' showed that the three dimensional structure of TRB' has not changed significantly from that of $TRB\;(C_{29}H_{34}O_9)$, except for the insertion of one oxygen atom into TRB to make additional pyran in the E-ring. It is also suggested that the aromatic moiety of TRA' is similar to that of $TRA\;(C_{28}H_{30}O_9)$ and the rest non-aromatic portions resemble to those of TRB'. The tremorgenic activity, lethality and inhibitory effect on acetylcholine esterase of TRA' and TRB' are greatly reduced comparing to that of TRA and TRB.

• 한국정보디스플레이학회:학술대회논문집
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• 2002.08a
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• pp.773-776
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• 2002

Efficient organic white light-emitting diodes are fabricated by doping [bis(2-methyl-8-quinolinolato) (tripheny-siloxy)aluminium (III)] (SAlq), a blue-emitting layer, with a red fluorescent dye of 4-dicyanomethylene-2-methyl-6-{2-(2,3,6,7-tetrahydro-1H,5H-benzo[i,j]quinolizin-8-yl)vinyl}-4H-pyran (DCM2). The incomplete energy transfer from blue-emitting SAlq to red-emitting DCM2 enables to obtain a balanced white light-emission. A device with the structure of ITO/TPD (50 nm)/SAlq:DCM2 (30 nm, 0.5 %)/$Alq_3$ (20 nm)/LiF (0.5 nm)/AI shows emission peaks at 456 nm and 482 nm from SAlq and at 570 nm from DCM2. The white light-emitting device shows an external quantum efficiency of about 2.3 %, a luminous efficiency of about 2.4 lm/W, and the CIE chromaticity coordinates of (0.32, 0.37) at 100 cd/m^2. A maximum luminance of about 23,800 cd/m^2. is obtained at 15 V and the current density of 782 mA/cm^2.

• Korean Journal of Fisheries and Aquatic Sciences
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• v.19 no.1
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• pp.45-51
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• 1986

Equimolar aqueous solutions of D-glucose and glycine were heated at $50^{\circ}C\;and\;95^{\circ}C$ at pH 6.7. The headspace volatiles and the ether extracts from the reaction mixture were analyzed by gas chromatography and gas chromatography-mass spectrometry using a fused silica capillary column. The major components formed were identified as diacetyl, three furfurals, two pyrroles, one furanone, two pyranones and two amides. In order to elucidate the formation mechanisms of the amides formed front amino-carbonyl reaction, two model systems were adopted. N-butylacetamide were formed as major components from diacetyl-butylamine ana glyoxal-butylamine systems, respectively. The results obtained suggest that such ${\alpha}-dicarbonyls$ as 3-deoxy-D-erythro-2,3-hexodiulose and diacetyl generated in the amino-carbonyl reaction react with amino compounds, amides then being formed by cleavage of the C-C bond in the ${\alpha}-dicarbonyls$.

• Polymer(Korea)
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• v.26 no.1
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• pp.18-27
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• 2002

Poly(ο-hydroxyamide)s as polybenzoxazoles precursors were synthesized by polycondensation from 2,2'-bis(3-amino-4-hydroxyphenyl) hexafluoropropane and various bis-acids. And the polymers were modified to acid-sensitive polyamides by introducing tetrahydropyran in order to impart photosensitivity. A study of optical transmittance at 365 nm, according to the chemical structure of bis-acid, revealed that the polymer derived from 4,4'-oxydibenzoic acid showed better optical transparency than those from other bis-acids. This tendency of optical transmittance could be explained by formation of charge transfer complex. In case of the polymer derived from 4,4'-oxydibenzoic acid, the electron accepting characteristic of bis-acid is reduced by introduction of electron donating group, -O-. Thus, optical transmittance increased due to the diminished formation of intramolecular charge transfer complex. In addition, the optical transmittance increased with increasing the THP content in the polymer. This is attributed to the reduced intermolecular interaction by the loosening of the packing density of the polymer chain.