• Title/Summary/Keyword: Dihydroxy Compound

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Chemical Constituents from Agrimonia pilosa with Inhibitory Activity against Interleukin 1β Production via NLRP3 and NLRC4 Inflammasomes

  • Nhoek, Piseth;Chae, Hee-Sung;An, Chae-Yeong;Pel, Pisey;Kim, Young-Mi;Chin, Young-Won
    • Natural Product Sciences
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    • v.27 no.4
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    • pp.228-233
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    • 2021
  • Bioactivity-guided fractionation by preliminary screening using interleukin-1β production in lipopolysaccharides (LPS)-induced J774A.1 cell line led to the isolation of fourteen structures including chromone, isocoumarins, flavanoids, and triterpenes from the aerial part of Agrimonia pilosa Ledeb. All structures were determined by measuring their spectroscopic data and comparing their spectroscopic data with the literatures. All the isolates were tested for their inhibitory activities against interleukin-1β production in LPS-induced J774A.1 cell. Of the tested compounds, (S)-(+)-5,7-dihydroxy-2-(1-methylpropyl)chromone (1), agrimonolide-6-O-β-D-glucopyranoside (5), agrimonolide-6-O-α-L-arabinofuranosyl-(1→6)-β-D-glucopyranoside (6), and catechin (10) were found to be active. Furthermore, compound 1 suppressed the protein expressions of NLRP3 and NLRC4 in murine macrophage.

Phytochemical Constituents of Climacium dendroides (곧은 나무이끼(Climacium dendroides)의 식물 화학적 성분연구)

  • Nam, Jung-Hwan;Cho, In-Sook;Kim, Su-Jeong;Nam, Chun-Woo;Seo, Jong-Taek;Yoo, Dong-Lim;Kim, Won-Bae;Ryu, Seung-Yeol;Lee, Eung-Ho;Kim, Min-Young;Yoo, Young-Min;Park, Hee-Juhn;Jung, Hyun-Ju
    • Applied Biological Chemistry
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    • v.51 no.2
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    • pp.136-141
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    • 2008
  • The chromatographic separation of organic solvent extracts of liverwort led to the isolation of six compounds. 2-Chromenone (1), 3, 4-dihydroxy-cinnamic acid (2), 3, 3', 4', 5, 7-pentahydroxy-2-phenylchromen-4-one (3), kaemperol-3-O-${\beta}$-D-glucopyranoside (4), 3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1, 4, 5-trihydroxycyclohexane carboxylic acid (5) and quercetin-3-O-rutinoside (6) were isolated from the methanolic extracts of the all part of Climacium dendroides. Their structure were established by chemical and spectroscopic methods. All compounds were isolated for the first time from this plant Climacium dendroides.

Application as a Cosmeceutical Ingredient of Euryale ferox Seed Extract (가시연꽃 종자 추출물의 화장품 원료로서의 특성)

  • Choo, Soo-Jin;Kim, Young-Hee;Ryoo, In-Ja;Xu, Guang-Hua;Yoo, Ick-Dong
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.35 no.4
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    • pp.309-315
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    • 2009
  • In our search for the natural cosmetic ingredients, we found that Euryale ferox seed extract exhibited the strong antioxidative activity. Five active compounds were isolated from the ethyl acetate extract through various chromatographic methods and their structures were determined by NMR and MS spectral analysis. These compounds were identified as fucosterol (1), 3-(4-hydroxy-3-methoxybenzyl)-4-[(7'R),5'-dihydroxy-3'-methoxybenzyl]tetrahydrofuran (2), resorcinol (3), pyrogallol (4) and 4-O-methylgallic acid (5).We evaluated the antioxidative, antielastase activities and melanogenesis inhibitory effects of these compounds. The $SC_{50}$ values of compounds 2 ~ 5 for free radical scavenging activity were $17.0\;{\sim}\;100.2\;{\mu}M$ and especially compounds 4 and 5 were 6-fold more effective than ferulic acid as a positive control. And compounds 2 ~ 4 inhibited human neutrophil elastase with $IC_{50}$ values of $18.8\;{\sim}\;78.2\;{\mu}M$ and compound 3 also inhibited melanin synthesis in B16F10 melanoma cells with an $IC_{50}$ value of $492.8\;{\mu}M$. These results suggest that Euryale ferox extract having a lot of various active ingredients may be useful as a natural multi-functioning agent.

Elution Profiles of Volatile Compounds and Free Amino Acids during Alcohol Soaking of Garlic(Allum sativum L.) (마늘의 alcohol 침지 중 휘발성 향기성분과 침출유리아미노산 함량)

  • Lee, Young-Guen
    • Journal of Life Science
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    • v.17 no.2 s.82
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    • pp.286-292
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    • 2007
  • Free amino acids and volatile compounds of fresh garlic and its liqueur were investigated to search elution profile of those components as basic data for development of garlic liqueur. The garlic was soaked in 20% alcohol solution and then sampled every week for 5 weeks. The major free amino acids were L-aspartic acid, L-glutamic acid, L-arginine, L-alanine, L-proline, L-asparagine and L-serine. Neutral amino acids such as L-threonine, L-proline, L-valine and L-leucine, and aromatic amino acids such as tyrosine and phenylalanine were eluted over 80% of those content in fresh garlic after 3 weeks of soaking, but acidic, basic and sulfur containing amino acids were below 80% even after 5 weeks. Sulfide compounds such as diallyl trisulfide, diallyl disulfide, methyl allyl disulfide, 2-vinyl-4H-1,3-dithi in, 3-vinyl-3,4-dihydro-1,2-dithiin, 3,5-diethyl-1,24-trithiolane, isobutyl isothiocyanate and diallyl sulfide were identified as major volatile compounds of fresh garlic by using GC/MS. Among volatile compounds of fresh garlic, allyl alcohol, diallyl disulfide, 3,5-diethyl-1,2,4-trithiolane, diallyl trisulfide and 3,4-dimethoxy furan were eluted to liqueur, but those compounds except 3,5-diethyl-1,2,4-trithiolane were lowered in liqueur during soaking. Furfural, 5-methylfurfural, 5-hydroxymethylfurfural, dimethyl pyrazine, furfuryl alcohol, 3-hydroxy-2-bytanone and 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyr-an-4-one were generated newly and their content increased in liqueur during soaking.

Identification of Antioxidative Components from Ethanol Extracts of Dalbergia odorifera T.CHEN (강진향(Dalbergia odorifera T.CHEN) 에탄올 추출물로부터 항산화 활성물질의 구조동정)

  • Choi, Ung;Kim, In-Won;Baek, Nam-In;Shin, Dong-Hwa
    • Korean Journal of Food Science and Technology
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    • v.34 no.5
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    • pp.893-897
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    • 2002
  • The chloroform layer from 75% ethanol extract of Dalbergia odorifera T.CHEN showed strong antioxidative activity on lard and palm oil as tested by Rancimat method. Antioxidative active compound isolated and identified by silica gel column chromatography, thin layer chromatography, mass spectrophotometer, $^1H-NMR$ and $^{13}C-NMR$ was identified as mucronulatol (3(R&S)-3,7-Dihydroxy-2',4-dimethoxyisoflavan). Results of Rancimat method revealed the induction period of Mucronulatol increased longer than those of synthetic antioxidant, BHA and BHT, at the same concentration. Mucronulatol combined with ${\delta}-tocopherol(200ppm)$, and with ascorbic acid (200 ppm) and citric acid (200 ppm) on lard and palm oil, respectively, showed strong synergistic effects.

Allelopathic Effects of Extracts of Trifolium repens on the Seed Germination and Seedling Growth of Zoysia japonica (토끼풀(Trifolium repens) 추출액이 잔디(Zoysia japonica)의 발아와 생장에 미치는 알레로파시 효과)

  • Lee, Ji-Hun;Kim, In-Taek;Lee, Ho-Jun;Kim, Yong-Ok
    • The Korean Journal of Ecology
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    • v.24 no.3
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    • pp.125-130
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    • 2001
  • The allelopathic effects of aqueous extracts from Trifolium repens were studied. Aqueous extracts of leaves, stems, roots and flowers of T. repens strongly inhibited the seed germination and seedling growth of Zoysia japonica. In general, the higher concentration of the extracts showed the more great inhibition effect. The phenolic compounds extracted from T repens were analysed and identified using gas chromatography. 14 phenolic compounds were isolated from the leaves, stems, roots and flowers: caffeic acid, p-hydroxy benzoic acid, ferulic acid, gallic acid, p-coumaric acid, vanillic acid, trans-cinnamic acid, 2,5 dihydroxy benzoic acid, syringic acid, 2-hydroxy cinnamic acid, benzoic acid, salicylic acid, phloroglucinol and phanylacetic acid. The seed germination and relative growth ratio of Z. japonica by 14 phenolic compounds were inhibited in whole treatment. Stronger growth inhibitor were benzoic acid, salicylic acid and trans-cinnamic acid. From these results it is suggested that the phenolic compounds from T. repens seemed to be responsible for the allelopathic potential.

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Neuroprotective and Anti-Neuroinflammatory Activities of Anthraquinones Isolated from Photorhabdus temperata Culture Broth

  • Yang, Eun-Ju;Kim, Seo-Hyun;Lee, Kyeong-Yeoll;Song, Kyung-Sik
    • 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.

Enhancing Effects of Indole-3-carbinol on Hepatocarcinogenesis and Thyroid Tumorigenesis in a Rat Multi-Organ Carcinogenesis Model

  • Kim, Dae-Joong;Han, Beom-Seok;Ahn, Byeong-Woo;Kim, Chang-Ok;Choi, Kwang-Sik;Lee, Joon-Sup
    • Proceedings of the Korean Society of Applied Pharmacology
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    • 1994.04a
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    • pp.339-339
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    • 1994
  • It has been reported that Indole-3-carbinol (I3C), a naturally occurring compound In cruclferous vegetables, exerts anticarcinogenic activity In several organs In rodents. The modifying effects of I3C were therefore assessed uging a rat multi-organ carcinogenesis model. A total of 100 male Sprague-Dawley rats were divided Into 3 groups. Animals of groups 1 and 2 were sequentially treated with diethylnitrosamine (DEN; 100 mg/kg b.w., i.p.), N-methylnitrosourea (NNU; 20 mg/kg b.w., 4 times for 2 weeks, i.p), and dihydroxy-di-N-propylnitrosauine (DHPN; 0.1% In d.w. for 2 weeks) for 4 weeks (DMD treatment). Animals of groups 1 and 3 were given the diet of 0.25% I3C for 20 weeks after DMD initiation and then were given basal diet for 28 weeks. All animals were sacrificed at week 24 and 52, respectively. I3C has been clearly demonstrated promoting effects on the development of glutathione S-transferase placental form (GST-P) positive hepatic foci at 24 weeks of the experiment. And I3C also exerted promoting potential In the hepatocellular adenoma (4/14; 29%) and the adenoma (7/14; 50%) of the thyroid gland at 52 weeks of the experiment. Therefore, I3C may promote hepatocarcinogenesis and thyroid tumorigenesis in the rat multi-organ carcinogenesis model.

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Fragrance Composition in Six Tree Peony Cultivars

  • Zhao, Jing;Hu, Zeng-Hui;Leng, Ping-Sheng;Zhang, Hui-Xiu;Cheng, Fang-Yun
    • Horticultural Science & Technology
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    • v.30 no.6
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    • pp.617-625
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    • 2012
  • Tree peony is a traditional famous flower of China, and plays an important role in Chinese traditional culture. But the floral scent of tree peony in vivo is little known. In this study, in order to explore the floral composition of tree peony, floral volatiles of six cultivars, including Paeonia suffruticosa 'Zhaofen' (ZF), P. suffruticosa 'Luoyanghong' (LYH), P. ostii 'Fengdanbai' (FDB), P. ${\times}$ lemonei 'High noon' (HN), P. ${\times}$ lemonei 'Renown' (R), and P. rockii 'Gaoyuanshenghuo' (GYSH) were collected by dynamic headspace and then identified by Automated Thermal Desorption-Gas Chromatography/Mass Spectometry. The results showed that floral fragrances of the six cultivars were qualitatively and quantitatively distinct. A total of 105 volatiles involving ten categories were detected. But not all volatile categories were emitted from these cultivars. The six peony cultivars emitted some shared compounds and peculiar compounds. The total released amounts of volatiles emitted from six cultivars were found significantly different, which was greatest for 'GYSH'. The most abundant volatile compounds detected from 'ZF', 'LYH', 'FDB', 'HN', 'R', and 'GYSH' were respectively ${\alpha}$-pinene, 2,3-dihydroxy propanal, 3-methyl-1-butanol, 2-ethyl-1-hexanol, acetic acid 1-methylethyl ester, and 5-ethyl-2,2,3-trimethyl heptane. This result may contribute to exploring the biosynthesis and emission mechanism of floral scent in tree peony.

Inhibitory Constituents against Cyclooxygenases from Aralia cordata Thunb

  • Dang Nguyen Hai;Zhang XinFeng;Zheng MingShan;Son Kun Ho;Chang Hyeun Wook;Kim Hyun Pyo;Bae KiHwan;Kang Sam Sik
    • Archives of Pharmacal Research
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    • v.28 no.1
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    • pp.28-33
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    • 2005
  • Seven diterpenes, four polyacetylenes, a lipid glycerol, and two sterols were isolated from the methylene chloride fraction of the root of Aralia cordata. Their chemical structures were determined as (-)-pimara-8(14), 15-dien-19-oic acid (2), pimaric acid (3), (-)-kaur-16-en-19-oic acid (4), 17-hydroxy-ent-kaur-15-en-19-oic acid (9), $7{\alpha}$-hydroxy-(-)-pimara-8(14), 15-dien-19-oic acid (10), $16\alpha$, 17 -dihydroxy-(-)-kauran-19-oic acid (11), 16-hydroxy-17-isovaleroyloxy-ent-kauran-19­oic acid (12), falcarindiol (5), dehydrofalcarindiol (6), dehydrofalcarindiol-8-acetate (7), falcarin­diol-8-acetate (8), alpha-mono palmitin (13), stigmasterol (1), and daucosterol (14) by the spectral evidences. These compounds were tested with COX-1 and COX-2 inhibition assays. This study found that compounds 2, 4, 5, 6, 7, 8, and 10 inhibited COX-1 dependent conversion of the exogenous arachidonic acid to $PGE_2$ in a dose-dependent manner with $IC_{50}$ values of $134.2{\mu}M$, $121.6{\mu}M$, $170{\mu}M$, $50.4{\mu}M$, $11.7{\mu}M$, $99.6{\mu}M$, and $69.6{\mu}M$, respectively. But, most of these compounds weakly inhibited COX-2 dependent $PGE_2$ generation. Among them, only compound 4 showed relatively significant inhibitory activity $(IC_{50}\;:\;127.6{\mu}M)$.