• Applied Biological Chemistry
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• v.50 no.1
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• pp.57-62
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• 2007

The fruiting body of Phellinus linteus was extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH and $H_2$O. The repeated silica gel and ODS column chromatographies of the EtOAc fraction led to isolation of four sterols. From the result of spectral data including NMR, MS and IR, the chemical structures of the sterols were determined as ergosta-7,24(28)-dien-3${\beta}$-ol (episterol, 1), 5${\alpha}$,8${\alpha}$-epidioxyergosta-6,9(11),22-trien-3${\beta}$-ol (dehydrop-eroxyergosterol, 2), 5${\alpha}$,8${\alpha}$-epidioxyergosta-6,22-dien-3${\beta}$-ol (ergoterol peroxide, 3), and $3{\beta}$,$5{\alpha}$-dihydroxy-6${\beta}$-methoxyergosta-7,22-diene (6-O-methylcerevisterol, 4). The ergosterols have been first isolated from this mushroom in this study.

• Advances in Traditional Medicine
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• v.10 no.4
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• pp.319-321
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• 2010

Plant saponins are widely distributed amongst plants and have a wide range of biological properties. Icosahydropicenic acid, $C_{51}H_{80}O_{19}$ ((4S,6bS)-8a-((4,5-dihydroxy-6-methyl-3-((3R)-3,4,5-trihydroxy-6-methyl-tetrahydro-2H-pyran-2-yloxy)-tetrahydro-2H-pyran-2-yloxy)carbonyl)-2-hydroxy-4, 6a, 6b, 11, 14b-pentamethyl-11-(2-methylprop-1-enyl)-3-(3,4,5-trihydroxy-6-(hydroxymethyl) - tetrahydro-2Hpyran-2-yloxy)-1, 2, 3, 4, 4a, 5, 6, 6a, 6b, 7, 8, 8a, 9, 10, 11, 12, 12a, 14, 14a, 14b-icosahydropicene-4-carboxylic acid), a new saponin was first time isolated from the roots of Clerodendrum Serratum (L) Moon (Verbenaceae). The structure elucidation of the compound was carried out by $^1H$ NMR and DART-MS studies.

• Archives of Pharmacal Research
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• v.28 no.5
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• pp.534-540
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• 2005

Activity-guided fractionation of the CH$_2Cl_2$-soluble fraction of the roots of Sophora flavescens furnished five 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scaveng ers: trans-hexadecyl ferulic acid (1) cis-octadecyl ferulic acid (2), trans-hexadecyl sinapic acid (3), (-)-4-hydroxy-3-methoxy-(6aR,11aR)-8, 9-methylenedioxypterocarpan (4) and desmethylanhydroicaritin (8), along with nine known inactive compounds: (-)-maackiain (5), xanthohumol (6), formononetin (7), (2S)-2'-methoxykurarinone (9), (2S)-3${\beta}$,7,4'-trihydroxy-5-methoxy-8-(${\gamma},{\gamma}$- imethylallyl )-flavanone (10), (2S)-7,4'-dihydroxy-5-methoxy-8- (${\gamma},{\gamma}$-dimethylallyl ) -flavanone (11), umbelliferone (12), kuraridin (13), and trifolirhizin (14). Compounds 1-4 and 8 exhibited DPPH free radical scavenging effects at IC$_{50}$ values of 33.01 ${\pm}$ 0.20, 57.06 ${\pm}$ 0.16, 39.84 ${\pm}$ 0.36, 35.83 ${\pm}$ 0.47, and 18.11 ${\pm}$ 0.04${\mu}$M, respectively. L-Ascorbic acid, when used as a positive control, exhibited an IC$_{50}$ value of 7.39 ${\pm}$ 0.01 ${\mu}$M. Compounds 1-4 and 8 also appeared to exert significant scavenging effects on authentic ONOO-, with IC$_{50}$ values of 5.76 ${\pm}$ 1.19, 15.06 ${\pm}$ 1.64, 8.17 ${\pm}$ 4.97, 1.95 ${\pm}$ 0.29 and 4.06 ${\pm}$ 2.41 ${\mu}$M, respectively. Penicillamine (IC$_{50}$= 2.36 ${\pm}$ 0.79${\mu}$M) was used as a positive control. In addition, compounds 2,4,6,8, and 10 were isolated from this plant for the first time.

• Archives of Pharmacal Research
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• v.27 no.4
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• pp.442-448
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• 2004

Wogonin (5,7-dihydroxy-8-methoxyflavone) is a down-regulator of cyclooxygenase-2 and inducible nitric oxide synthase expression, contributing to anti-inflammatory activity in vivo. For further characterization of modulatory activity on ploinflammatory gene expression in vivo, the effect of wogonin was examined in this experiment using animal models of skin inflammation. By topical application, wogonin inhibited an edematic response as well as ploinflammatory gene expression against contact dermatitis In mice. Wogonin inhibited ear edema ($19.4-22.6\%$) at doses of $50-200\;{\mu}g$/ear and down-regulated interleukin-$1{\beta}$ induction ($23.1\%$) at $200{\mu}g$/ear in phenol-induced simple irritation. Wogonin ($2{\times}50-2{\times}200{\mu}g$/ear) also inhibited edematic response ($51.2-43.9\%$) and down-regulated ploinflammatory gene expression of cyclooxygenase-2, interleukin-$1{\beta}$, interferon-$\gamma$, intercellular adhesion molecule-1 and inducible nitric oxide synthase with some different sensitivity against picryl chloride-induced delayed hypersensitivity reaction. All these results clearly demonstrate that wogonin is a down-regulator of ploinflammatory gene expression in animal models of skin inflammation. Therefore, wogonin may have potential for a new anti-inflammatory agent against skin inflammation.

• Biomolecules & Therapeutics
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• v.27 no.1
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• pp.41-47
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• 2019

The apoptotic effects of shikonin (5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-enyl]naphthalene-1,4-dione) on the human colon cancer cell line SNU-407 were investigated in this study. Shikonin showed dose-dependent cytotoxic activity against SNU-407 cells, with an estimated $IC_{50}$ value of $3{\mu}M$ after 48 h of treatment. Shikonin induced apoptosis, as evidenced by apoptotic body formation, sub-G_1$ phase cells, and DNA fragmentation. Shikonin induced apoptotic cell death by activating mitogen-activated protein kinase family members, and the apoptotic process was mediated by the activation of endoplasmic reticulum (ER) stress, leading to activation of the $PERK/elF2{\alpha}/CHOP$ apoptotic pathway, and mitochondrial $Ca^{2+}$ accumulation. Shikonin increased mitochondrial membrane depolarization and altered the levels of apoptosis-related proteins, with a decrease in B cell lymphoma (Bcl)-2 and an increase in Bcl-2-associated X protein, and subsequently, increased expression of cleaved forms of caspase-9 and -3. Taken together, we suggest that these mechanisms, including MAPK signaling and the ER- and mitochondria-mediated pathways, may underlie shikonin-induced apoptosis related to its anticancer effect.

• Journal of Microbiology and Biotechnology
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• v.28 no.1
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• pp.12-21
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• 2018

Photorhabdus temperata (PT), a gram-negative bacterium, lives symbiotically within entomopathogenic nematodes. The insecticidal compounds derived from Photorhabdus are used as biopesticides in agriculture. However, the physiological properties are not well characterized. In the course of our screening for neuroprotective and anti-neuroinflammatory substances from natural products, the culture broth of PT showed considerable activities. By activity-guided purification, five anthraquinones, namely, 3-methoxychrysazine (1), 1,3-dimethoxy-8-hydroxy-9,10-anthraquinone (2), 1,3,8-trihydroxy-9,10-anthraquinone (3), 3,8-dihydroxy-1-methoxy-9,10-anthraquinone (4), and 1,3,4-trimethoxy-8-hydroxy-9,10-anthraquinone (5), were isolated from the ethyl acetate fraction of the PT culture broth. Among the isolated compounds, $75{\mu}M$ 3 significantly protected mouse hippocampal neuronal cells (HT22) against 5 mM glutamate-induced cell death via the inhibition of reactive oxygen species production, $Ca^{2+}$ influx, and lipid peroxidation. Additionally, 3 and 4 effectively suppressed the interferon-${\gamma}$-induced neuroinflammation of mouse-derived microglial cells (BV2) at 10 ng/ml, via the reduction of nitric oxide, interleukin-6, and tumor necrosis factor-${\alpha}$. Anthraquinones 3 and 4 derived from the PT culture broth are a potential starting point to discover neuroprotective and anti-neuroinflammatory drug leads. The novel compound 5 is reported for the first time in this study.

• Mycobiology
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• v.51 no.3
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• pp.148-156
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• 2023

Penicillium oxalicum strain can be isolated from the Bletilla striata (Thunb.) Reichb. f. tubers. Its solid-state fermentation products are concentrated by percolation extraction. Separation and purification have been conducted to the ethyl acetate extracts by preparative HPLC. Based on the use of spectrometry, we have determined 17 known compounds, 12,13-dihydroxy-fumitremorgin C (1), pseurotin A (2), tyrosol (3), cyclo-(L-Pro-L-Val) (4), cis-4-hydroxy-8-O-methylmellein (5), uracil (6), cyclo-(L-Pro-L-Ala) (7), 1,2,3,4-tetrahydro-4-hydroxy-4-quinolin carboxylic acid (8), cyclo-(Gly-L-Pro) (9), 2'-deoxyuridine (10), 1-(b-D-ribofuranosyl)thymine (11), cyclo-(L-Val-Gly) (12), 2'-deoxythymidine (13), cyclo-(Gly-D-Phe) (14), cyclo-L-(4-hydroxyprolinyl)-D-leucine (15), cyclo-(L)-4-hydroxy-Pro-(L)-Phe (16), uridine (17). Here, we report compounds 1-3, 5, 7-8, 11-12, 14-17 are first found and isolated from this endophyte.

• Archives of Pharmacal Research
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• v.26 no.8
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• pp.606-611
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• 2003

Byakangelicin, 9-(2,3-dihydroxy-2-methylbutoxy)-4-methoxy-7H- furo[3,2-g][l]benzopyran-7-one (BKG), a component of Angelicae dahuricae Radix, is considered to be an inhibitor of aldose reductase for the treatment of diabetic cataract. An analytical method for the isolation of BKG developed by high-performance liquid chromatography has been reported. No literature on the metabolism of BKG, however, has been found. With the purpose of identifying new metabolites of BKG, BKG (100 mg/kg) was orally administered to Sprague-Dawley rats via a gavage. Using a metabolic cage, urine was collected for 24 h, and the urine samples were extracted by liquid-liquid extraction. For structural identification of new urinary metabolites of BKG, various instrumental analyses were conducted by gas-chromatography/mass spectrometry, high-performance liquid chromatography/diode array detector, liquid chromatography/mass spectroscopy with thermospray interface and $^1H$ nuclear magnetic resonance spectroscopy. Two metabolites produced from the Ο-demethylation or Ο-dealkylation of BKG were newly identified, and another new but unknown metabolite was assumed to be the hydroxylated form of BKG. These results indicate that the major metabolic products of BKG are formed by Ο-demethylation or Ο-dealkylation of BKG side chains.

• Microbiology and Biotechnology Letters
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• v.37 no.1
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• pp.1-9
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• 2009

The genetic monitoring method was developed for the rapid detection of the PGPR and biocontrol agent, B. subtilis AH18 in red-pepper field soil by multiplex PCR using sid, aec and cel gene primers. The monitoring of B. subtilis AH18 in the soil was carried by amplified a 2,3-dihydro-2,3-dihydroxy benzoate dehydrogenase [EC: 1. 3. 1. 28]gene (sid - 794 bp : EF408238) which is a key enzyme of siderophore synthesis, an auxin efflux carrier gene (aec - 1,052 bp : EF408239) and a cellulase gene (cel - 1,582 bp : EF070194). The natural un sterilized soil was inoculated with B. subtilis AH18 to determine the sensitivity ($1.8\times10^5$ cfu/g) of multiplex PCR for the rapid dectection and then the strain was monitored successfully in rhizosphere or non-rhizosphere soil of red-pepper cultural soil. At 3 weeks after the treatment, density of the strain was monitored more abundantly in rhizosphere soil.

• Preventive Nutrition and Food Science
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• v.21 no.1
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• pp.68-72
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• 2016

To examine the possibility of using thiacremonone isolated from high-temperature-high-pressure treated garlic, this study investigated the physiological activities properties. The $IC_{50}$ values of hydroxyl, superoxide, hydrogen peroxide, and nitric oxide radical scavenging activities of thiacremonone were 92.50, 65.05, 12.60, and $81.53{\mu}g/mL$, respectively. On the other hand, the activities of vitamin C were 104.93, 99.43, 42.42, and $122.64{\mu}g/mL$, and the activities of butylated hydroxyanisole were 37.22, 68.45, 22.47, and $40.54{\mu}g/mL$, respectively. The $IC_{50}$ value of ACE inhibition activities of thiacremonone and captoprill were 0.265 and $0.036{\mu}g/mL$, respectively. The $IC_{50}$ value of xanthine oxidase inhibition activities of thiacremonone and allopurinol were 39.430 and $9.346{\mu}g/mL$, respectively. The $IC_{50}$ value of tyrosinase inhibition activities of thiacremonone and kojic acid were 101.931 and $65.648{\mu}g/mL$, respectively.