• Korean Journal of Pharmacognosy
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• v.39 no.2
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• pp.86-90
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• 2008

Two decursin derivatives were synthesized from decursinol. Compounds 1 and 2 were determined as 7-{3-[4-(2-Methoxy-phenyl)-piperazin-1-yl]-propoxy}-8,8-dimethyl-7,8-dihydro-6H-pyranochromen-2-one (1) and decursinol 3'-O-E-pmethoxycinnamic acid ester (2), respectively and newly reported. Compounds 1 and 2 significantly inhibited AChE activity and ameliorated memory impairment induced in mice by scopolamine (1.0 mg/kg body weight s.c.) as measured in passive avoidance test. We suggest, therefore, that compounds 1 and 2 has both anti-AChE and anti-amnesic activities that may ultimately hold significant therapeutic value in alleviating certain memory impairment observed in Alzheimer's disease.

• Korean Journal of Pharmacognosy
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• v.35 no.4 s.139
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• pp.315-319
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• 2004

Three coumarin derivatives, which stimulate collagen biosynthesis in human fibroblasts were isolated from Angelica dahurica root which has been used in traditional medicine for cold, headache, discharging blood and women's diseases. Three coumarin derivatives were identified as 5-benzofuranacrylic acid, $6,7-dihydroxy-4-(3-methyl-2-butenyl)-{\delta}-lactone\;(prangenidin)$, 5-benzofuranacrylic acid, $6,7-dihydroxy-4-methoxy-{\delta}-lactone\;(8-hydroxybergapten)$ and 5-benzofuranacrylic acid, 8-hydroxypsoralen(xanthotoxol) from their spectral data.

• Microbiology and Biotechnology Letters
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• v.45 no.3
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• pp.200-208
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• 2017

Actinobacteria are prolific producers of a large number of natural products with diverse biological activities. In the present study, an actinobacterium isolated from sunflower rhizosphere soil sample collected from Medak, Andhra Pradesh, South India was identified as Amycolatopsis thermoflava strain SFMA-103. A pigmented secondary metabolite in culture broth was extracted by using methanol and it was further purified by silica gel column chromatography with methanol-chloroform solvent system. Structural elucidation studies based on UV-visible, 1D and 2D-NMR, FT-IR, and mass spectroscopic analyses confirmed the structure as 1-methoxy-3-methyl-8-hydroxy-anthraquinone. It showed significant in vitro anticancer activity against lung cancer and lymphoblastic leukemia cells with $IC_{50}$ values of 10.3 and $16.98{\mu}M$, respectively. In addition, 1-methoxy-3-methyl-8-hydroxy-anthraquinone showed good free radical scavenging activity by DPPH method with an $EC_{50}$ of $18.2{\mu}g/ml$. It also showed other promising superoxide radical scavenging, nitric oxide radical scavenging and inhibition of lipid peroxidation activities. This is a first report of anti-proliferative and antioxidant activities of 1-methoxy-3-methyl-8-hydroxy-anthraquinone isolated from A. thermoflava strain SFMA-103 which may find potential application in biotechnological and pharmaceutical fields.

• Archives of Pharmacal Research
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• v.20 no.1
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• pp.88-90
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• 1997

Two compounds were newly isolated from the leaves of Aloe barbadensis Mill. Their strucutres were identified as 3, 4-dihydro-3, 9-dihydroxy-8-methoxy-3-methyl-1(2H)-anthracenone(1) and 10-.betha.-D-glucopyranosyl-1, 80, 10-trihydroxy-3-(hydroxymethyl)-(R)-9(10H)-anth racenone(2) by chemical and spectral evidences.

• Bulletin of the Korean Chemical Society
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• v.17 no.8
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• pp.693-695
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• 1996

The steric effect on the first order hyperpolarizability of the β-nitrostyrene derivatives has been investigated by comparing the β values and the dihedral angles between the aryl and nitroalkenyl groups. In general the β value increased with the electron-donating ability of the substituent. The larger β value for 3,4-dimethoxy-β-nitrostyrene than that for p-methoxy-β-nitrostyrene has been attributed to the lower charge transfer energy for the former. The most striking substituent effect was observed in the β-methyl-β-nitrostyrene derivatives. Thus the β values for 3,4-dimethoxy- and p-methoxy derivatives of the latter decreased to near zero, probably because of the large distortion from planarity caused by the steric repulsion between the β-methyl and the aryl groups. The larger β value for p-dimethylamino-β-methyl-β-nitrostyrene has been interpreted with an increased electron-donating ability of the substituent and increased co-planarity.

• Bulletin of the Korean Chemical Society
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• v.32 no.spc8
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• pp.2938-2940
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• 2011

Novel C-aryl glucoside SGLT2 inhibitors containing triazine motif were designed and synthesized for biological evaluation. Among the compounds assayed, triazine containing methoxy moiety 18 demonstrated the best in vitro inhibitory activity against hSGLT2 in this series to date ($IC_{50}$ = 24.9 nM).

• Journal of the Korean Society of Food Science and Nutrition
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• v.23 no.2
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• pp.232-237
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• 1994

Changes of volatile components in modified oleoresin red pepper during cooking at high temperature were investigated. Dried red pepper was milled to 100mesh of size particle and oily compounds were extracted by reduced pressure steam distrillation. The rest part was reextracted and concentrated. The extracts were combined. The same volume of water and 4% of polyglycerol condensed ricinoleate (PGDR) were added to the combined extract, and emulsified to make oleoresin red pepper 119 volatile compounds were separated from the dried red pepper and oleoresin and 35 components were identified in both samples. The major flavor compounds were identified to be 2-methoxy-phenol, 2, 6-bis(1, 1-dimethylethyl)-4-methyl-phenol, 1, 4-dimethylbenzene, thylbenzene, 1, 2-benzenedicarboxylic acid, 2-methoxyl-4-methylphenol, 4-ethyl-2-methoxy-phenol, and 5- methyl-2-furancarboxyaldehyde, and their transferal from raw red pepper to oleresin was low. 93 voltilie compounds were isolated after 3 hours cooking at 100 and 82 volitile compounds were separated after that at $150^{\circ}C$. Degeneration of volatile compounds was peculiarly proportional to the temperature of cooling. Capsaicin was relatively stable during cooking and remaining ratio after cooking at 100 and $150^{\circ}C$ was 84.7% and 73.3%. respectively. Oleoresin from red pepper had a little antioxidation effect at $100^{\circ}C$ cooking, but, antioxidation effect at $150^{\circ}C$ cooking was not shown due to degradation of capsaicin.

• Molecules and Cells
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• v.25 no.2
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• pp.231-241
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• 2008

Indole glucosinolates (IG) play important roles in plant defense, plant-insect interactions, and stress responses in plants. In an attempt to metabolically engineer the IG pathway flux in Chinese cabbage, three important Arabidopsis cDNAs, CYP79B2, CYP79B3, and CYP83B1, were introduced into Chinese cabbage by Agrobacterium-mediated transformation. Overexpression of CYP79B3 or CYP83B1 did not affect IG accumulation levels, and overexpression of CYP79B2 or CYP79B3 prevented the transformed callus from being regenerated, displaying the phenotype of indole-3-acetic acid (IAA) overproduction. However, when CYP83B1 was overexpressed together with CYP79B2 and/or CYP79B3, the transformed calli were regenerated into whole plants that accumulated higher levels of glucobrassicin, 4-hydroxy glucobrassicin, and 4-methoxy glucobrassicin than wild-type controls. This result suggests that the flux in Chinese cabbage is predominantly channeled into IAA biosynthesis so that coordinate expression of the two consecutive enzymes is needed to divert the flux into IG biosynthesis. With regard to IG accumulation, overexpression of all three cDNAs was no better than overexpression of the two cDNAs. The content of neoglucobrassicin remained unchanged in all transgenic plants. Although glucobrassicin was most directly affected by overexpression of the transgenes, elevated levels of the parent IG, glucobrassicin, were not always accompanied by increases in 4-hydroxy and 4-methoxy glucobrassicin. However, one transgenic line producing about 8-fold increased glucobrassicin also accumulated at least 2.5 fold more 4-hydroxy and 4-methoxy glucobrassicin. This implies that a large glucobrassicin pool exceeding some threshold level drives the flux into the side chain modification pathway. Aliphatic glucosinolate content was not affected in any of the transgenic plants.

• Bulletin of the Korean Chemical Society
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• v.17 no.7
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• pp.643-647
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• 1996

1,2-Disubstituted chiral calix[4]arene "25-(3,5-dinitrobenzoyloxy)-26-methoxy-27,28-dihydroxycalix[4]arene" was synthesized by the reaction of 25-(3,5-dinitrobenzoyloxy)-calix[4]arene with methyl iodide in the presence of K2CO3. Methylation was occurred at the 26-position of calix[4]arene. The partial cone conformation and 1,2-substitution were characterized based on the 1H NMR, 13C NMR and X-ray diffraction analysis. The crystal structure has been determined by X-ray diffraction method. The crystals are orthorhombic, Pbca, a=10.652(1), b=17.687(1), c=32.247(3) Å, Z=8, V=6075.4(9) Å3, Dc=1.38gcm-3. The intensity data were collected on an Enraf-Nonius CAD-4 Diffractometer with a graphite monochromated Cu-Kα radiation. The structure was solved by direct method and refined by full-matrix least-squares methods to a final R value of 0.050 for 2368 observed reflections. The molecule is in the partial cone conformation. It has two strong intramolecular hydrogen bonds of O(1D)-H…O(1C)-H…O(1B).

• Archives of Pharmacal Research
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• v.25 no.6
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• pp.842-850
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• 2002

Tissue factor (TF, tissue thromboplastin or coagulation factor III) accelerates the blood clotting, activating both the intrinsic and the extrinsic pathways to serve as a cofactor. In order to isolate TF inhibitors from the fruits of Chaenomeles sinensis, an activity-guided purification utilizing a bio-assay method of prothrombin time prolongation, was carried out to yield five active flavoniods such as hovetrichoside C (1) ($IC_{50}$ = 14.0 $\mu$g), luteolin-7-Ο-$\beta$-D-glucuronide (3) ($IC_{50}$ = 31.9$\mu$g), hyperin (4) ($IC_{50}$ = 20.8 $\mu$g), avicularin (6) ($IC_{50}$ = 54.8 $\mu$g) and quercitrin (10) ($IC_{50}$ = 135.7 $\mu$g), along with other inactive compounds such as ($\pm$)-(2E,4E)-Ο-$\beta$-D-glucopyranosyl-4'-hydroxy-$\beta$-ionylideneacetic acid ester (2), genistein-7-Ο-$\beta$-D-glucopyranoside (5), luteolin-3'-methoxy-4'-Ο-$\beta$-D-glucopyranoside (7), luteolin-7-Ο-$\beta$-D-glucuronide methyl ester (8), tricetin-3'-methoxy-4'-Ο-$\beta$-D-glucopyranoside (selagin-4'-Ο-$\beta$-D-glucopyranoside) (9), (-)-epicatechin (11), luteolin-4'-Ο-$\beta$-D-glucopyranoside (12) and apigenin-7-Ο-$\beta$-D-glucuronide methyl ester (13). The structures of the isolated compounds were elucidated through spectral analysis. Among them, compounds 1 to 9, 12 and 13 were isolated for the first time from the fruits of this plant and the compound 9 is a new flavonoid.