• Applied Biological Chemistry
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• 제50권1호
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• pp.57-62
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• 2007

상황버섯 자실체를 80% MeOH 용액으로 추출하고, 추출물을 EtOAc, n-BuOH 및 물로 분배, 추출하였다. 이 중 EtOAc 분획을 silica gel 및 octadecylsilica gel(ODS) column chromatography로 정제하여 4종의 sterol 화합물을 분리하였다. 각 화합물의 화학구조는 NMR, MS 및 IR 등의 스펙트럼 데이터를 해석하여, ergosta-7,24(28)-dien-3${\beta}$-ol (episterol, 1), 5${\alpha}$,8${\alpha}$-epidioxyergosta-6,9(11),22-trien-3${\beta}$-ol (dehydroperoxyergosterol, 2), 5${\alpha}$,8${\alpha}$-epidioxyergosta-6,22-dien-3${\beta}$-ol (ergoterol peroxide, 3), 및 $3{\beta}$,$5{\alpha}$-dihydroxy-6${\beta}$-methoxyergosta-7,22-diene (6-O-methylcerevisterol, 4)로 동정하였다. 이 화합물들은 이번에 상황에서 처음 분리 보고되었다.

• Advances in Traditional Medicine
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• 제10권4호
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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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• 제28권5호
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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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• 제27권4호
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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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• 제27권1호
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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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• 제28권1호
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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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• 제51권3호
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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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• 제26권8호
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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.

• 한국미생물·생명공학회지
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• 제37권1호
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• pp.1-9
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• 2009

식물성장촉진물질인 auxin을 비롯한 식물병원성진균을 방제하는 siderophore 그리고 식물병원성 진균의 세포벽을 분해하는 cellulase를 동시에 생산하는 생물방제균주 B. subtilis AH18의 토양내 monitoring을 위하여 각 생산물질에 관여하는 유전자를 기초로 primer(sid, aec, cel)를 제작하였다. Single PCR 및 multiplex PCR을 수행하여 800-bp(sid), 1000-bp(air), 1600-bp(cel)의 DNA fragment를 확인하였으며, 각각의 fragment는 siderophore의 생합성 key enzyme인 2,3-dihydro-2,3-dihydroxy benzoate dehydrogenase[EC : 1. 3. 1, 28]gene (sid-794bp)이며, auxin efflux carrier gene (aec - 1052 bp), 그리고 cellulase gene(cel - 1582 bp)임을 확인하고, NCBI Genbank에 등록하였다(Genbank accession sid: No. EF408238, aec: No. EF408239, cel: No. EF070194). 또한 B. subtilis AH18을 처리한 일반 경작지 토양에서 multiplex PCR을 통하여 3종의 유전자에서 증폭된 triple band를 확인하였으며, 고추를 실제 토양을 이용해 Pot에 이식 후 고추의 rhizosphere와 non-rhizosphere에서 B. subtilis AH18의 존재를 확인할 수 있다. 뿐만아니라 본 균주를 고추가 이식된 Pot의 토양에 처리 후 monitoring시 민감도는 $1.8\times10^5$ cfu/g이었고, monitoring 가능한 기간은 3주이상 확인 할 수 있었다.

• Preventive Nutrition and Food Science
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• 제21권1호
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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.