• Title/Summary/Keyword: bergapten

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Chemical Constituents of the Halophyte Glehnia littoralis (염생식물 갯방풍의 화학적 성분연구)

  • Um, Young-Ran;Lee, Jung-Im;Lee, Jin-Hyeok;Kim, Hae-Jin;Yea, Sung-Su;Seo, Young-Wan
    • Journal of the Korean Chemical Society
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    • v.54 no.6
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    • pp.701-706
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    • 2010
  • Two polyacetylenes (1 and 2), four coumarins (3-6), and one sesquiterpene (7) were isolated from the halophyte Glehnia littoralis. Particularly, compound 6 and 7 were isolated for the first time from Glehnia littoralis. Their chemical structures have been determined by extensive 2-D NMR experiments such as $^1H$, COSY, HMQC and HMBC and by comparison with the reported data in the literature.

GC/MS and HPLC/PDA characterization of essential oils and phenolic compounds from the aerial parts of common rue (Ruta graveolens)

  • Chang-Dae Lee;Hak-Dong Lee;Yunji Lee;Hwan Myung Lee;Sanghyun Lee
    • Journal of Applied Biological Chemistry
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    • v.66
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    • pp.144-152
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    • 2023
  • Two different extraction methods were used to evaluate the medical value of common rue, Ruta graveolens L. (RGL). The results of our 2,2-diphenyl-1-picrylhydrazyl and 2,2'-azino-bis-3-ethylbenzothiazoline-6-sulphonic acid assays indicated that the antioxidant activity of RGL essential oil extract obtained through steam distillation was very low, whereas ethanol (EtOH) extracts of RGL showed higher antioxidant activity. RGL essential oil was extracted by steam distillation and characterized by GC/MS analysis. Furthermore, EtOH extracts of RGL were obtained under reflux and analyzed by HPLC/PDA. The GC/MS results indicated that the ketone compounds 2-undecanol acetate, nonyl cyclopropanecarboxylate, and 2-nonanone accounted for more than 70% of the composition of RGL essential oil. The HPLC/PDA analyses indicated that the RGL extracts were rich in phenolic compounds such as protocatechuic acid, rutin, psoralen, xanthotoxin, and bergapten, among which rutin was the most abundant. Collectively, our results demonstrated that RGL contains high levels of phenolic compounds and could thus be commercialized as a valuable plant-derived antioxidant.

Inhibition of Nitric Oxide Production by Coumarins from Peucedanum japonicum in LPS-Activated RAW 264.7 cells (갯기름나물의 쿠마린에 의한 RAW 264.7 세포주의 Nitric Oxide 생성 저해활성)

  • Choi, Hee-Cheol;Rho, Tae-Cheol;Kim, Bo-Yeon;Ko, Hack-Ryong;Oh, Won-Keun;Seong, Chang-Keun;Mheen, Tae-Ick;Ahn, Jong-Seog;Lee, Hyun-Sun
    • Korean Journal of Pharmacognosy
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    • v.30 no.2
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    • pp.99-104
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    • 1999
  • During the screening for inhibitors of nitric oxide production in LPS-activated macrophage, RAW 264.7 cells. Five coumarins were isolated from chloroform extract of the root of Peucedanum japonicum. They were identified as praeruptorin A (1), xanthotoxin (2), psoralen (3), isopimpinellin (4), bergapten (5) on the basis of spectroscopic methods. The $IC_{50}$ values for nitrite production by activated macrophages were about $1.5\;{\mu}g/ml$ (1), $0.3\;{\mu}g/ml$ (2), $1.0\;{\mu}g/ml$ (3), $25\;{\mu}g/ml$ (4), $25\;{\mu}g/ml$ (5), respectively. However, the inducible nitric oxide synthase (iNOS) was not inhibited by treatment with these compounds. Their inhibitory effect on nitric oxide production was resulted from the supperssion of iNOS expression.

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Chemical Constituents of Saposhnikovia divaricata (방풍의 화학 성분)

  • Kim, So-Jun;Chin, Young-Won;Yoon, Kee-Dong;Ryu, Min-Youl;Yang, Min-Hye;Lee, Je-Hyun;Kim, Jin-Woong
    • Korean Journal of Pharmacognosy
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    • v.39 no.4
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    • pp.357-364
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    • 2008
  • The roots of Saposhnikovia divaricata Schischk. (Umbelliferae) have been known to possess analgesic, anti-inflammatory, anti-parasitic and anti-bacterial activities, and used for curing headaches, fever and arthralgia. In this study, we aimed to isolate active constituents to provide phytochemical data for the quality control of this plant. Nine coumarins, eight chromones, three sterols and a coumarolignan were isolated from EtOAc-soluble fraction of the roots of S. divaricata through repetive column chromatography method using silica gel, ODS gel, Sephadex-LH 20, MPLC and HPLC. By analyses of spectroscopic data and comparison of their data with those of published values, the compounds were identified as 3'-O-angeloylhamaudol (1), ${\beta}$-sitosterol (2), marmesin (3), phellopterin (4), anomalin (5), imperatorin (6), xanthotoxin (7), deltoin (8), bergapten (9), stigmasterol (10), ledebouriellol (11), hamaudol (12), 8'-epicleomiscosin A (13), xanthoarnol (14), cimifugin (15), 5-O-methylvisamminol (16), daucosterol (17), 4'-O-${\beta}$-D-glucosyl-5-O-methylvisamminol (18), nodakenin (19), sec-O-glucosylhamaudol (20), prim-O-glucosylcimifugin (21). Among them, 8'-epicleomiscosin (13) was firstly reported from Umbelliferae family and xanthoarnol (14) and nodakenin (19) were isolated from this plant for the first time.

Simultaneous Determination of 11 Marker Compounds in Gumiganghwal-tang by HPLC-DAD and LC-MS

  • Weon, Jin Bae;Jung, Youn Sik;Ryu, Gahee;Yang, Woo Seung;Ma, Choong Je
    • Natural Product Sciences
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    • v.22 no.4
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    • pp.238-245
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    • 2016
  • Gumiganghwal-tang has been used for the treatment of common cold for a long-time. We developed an accurate and sensitive high performance liquid chromatography-diode array detection (HPLC-DAD) and electrospray ionization mass spectrometry method for the simultaneous determination of ferulic acid, baicalin, bergapten, methyl eugenol, glycyrrhizin, oxypeucedanin, wogonin, nodakenin, atractylenolide III, imperatorin, and atractylenolide I in Gumiganghwal-tang samples. The analytes were separated on a Shiseido C18 column ($5{\mu}m$, $4.6mm\;I.D.{\times}250mm$) with gradient elution with acetonitrile and 0.1% trifluoroacetic acid. Eleven compounds were quantitatively determined by HPLC-DAD and identified by LC-MS data. We also validated this method. The calibration curves of all the compounds showed good linear regression. The limits of detection and the limits of quantification ranged from 0.04 to 0.63 and from 0.12 to $1.92{\mu}g/mL$, respectively. The relative standard deviation values of intra- and inter-days of this method represented less than 2.9%. The recoveries were found to be in the range of 90.06 - 107.66%. The developed method has been successfully applied to the analysis of Gumiganghwaltang samples. The established HPLC method could be used to quality control of Gumiganghwal-tang.

5-Lipoxygenase Inhibition of the Fructus of Foeniculum vulgare and Its Constituents

  • Lee, Je-Hyeong;Lee, Dong-Ung;Kim, Yeong-Shik;Kim, Hyun-Pyo
    • Biomolecules & Therapeutics
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    • v.20 no.1
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    • pp.113-117
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    • 2012
  • The fruits of Foeniculum vulgare (Foeniculi Fructus) have been widely used in Chinese medicine as an antiemetic, ameliorating stomach ailments and as an analgesic. In order to establish its potential for antiallergic use, inhibitory actions of the fruit on 5-lipoxgenase (5-LOX) and ${\beta}$-hexosaminidase release were evaluated. The 70% ethanol extract of this plant material (FR) considerably inhibited 5-LOX-catalyzed leukotriene production from A23187-induced rat basophilic leukemia (RBL)-1 cells. The $IC_{50}$ was $3.2{\mu}g/ml$. From this extract, 12 major compounds including sabinene, fenchone, ${\gamma}$-terpinene, ${\alpha}$-pinene, limonene, p-anisylacetone, panisylaldehyde, estragole (4-allylanisole), trans-anethole, scopoletin, bergapten and umbelliferone were isolated. And it was found that several terpene derivatives including ${\gamma}$-terpinene and fenchone as well as phenylpropanoid, trans-anethole, showed considerable inhibitory action of 5-LOX. In particular, the $IC_{50}$ of trans-anethole was $51.6{\mu}M$. In contrast, FR and the isolated compounds did not show considerable inhibitory activity on the degranulation reaction of ${\beta}$-hexosaminidase release from antigen-treated RBL-2H3 cells. Against arachidonic acid-induced ear edema in mice, FR and trans-anethole showed significant inhibition by oral administration at doses of 100-400 mg/kg. In conclusion, FR and several major constituents are 5-LOX inhibitors and they may have potential for treating 5-LOX-related disorders.

PHOTOCHEMISTRY AND PHOTOBIOLOGY OF PSORALENS

  • Shim, Sang-Chul;Jeon, Young Hee;Kim, DongWon;Han, GyuSeok;Yoo, Dong Jin
    • Journal of Photoscience
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    • v.2 no.1
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    • pp.37-45
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    • 1995
  • INTRODUCTION : Psoralens are planar tricyclic furocoumarins present in numerous plants and fungi found throughout the world.' Naturally occurring and synthesized psoralen derivatives(see Figure 1) are photosensitizers of UVA especially from 320 nm to 400 nm, a range at which cellular nucleic acids and proteins are weakly absorbing if any at all. Because of their skinphotosensitizing properties, these compounds have been used in the photochemotherapy of psoriasis and vitiligo. However, undesirable side effects such as carcinoma development in hairless mice as well as possible liver damage from the use of 8-methoxypsoralen(8-MOP) have been reported. The other photobiological effects include inactivation of DNA viruses, killing and mutagenesis of bacteria, inhibition of tumor transmitting capacity of various cells, and hyperpigmentation on human and guinea pig skin. PUVA(psoralen+UVA) photochemotherapy is in fact thousands of years old, having been used in Egypt and India since B.C. 1200-2000. Photochemotherapy for a common disfiguring disease, vitiligo, was practiced in the ancient world by physicians and herbalists who used boiled extracts of the fruits of certain umbelliferous plants, e.g. Ammi majus Linnaeus in Egypt or the leguminous plants, Psoralea corylifolia L. in India. It was first described by Kuske in 19388 that photosensitization of skin by plants was related to the presence of psoralen. He identified natural psoralens in plants as photosensitizers and isolated bergapten(5methoxypsoralen) from the oil of bergamot. The scientific interest in photosensitizing psoralens, however, has grown considerably after the introduction into clinics of the psoralen photochemotherapy for the treatment of psoriasis and of other skin (abbreviation)

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Anti-proliferative effect of methanolic extracts from Citrus junos seeds and seed oils on HT-29 human colon cancer cells and identification of their major bioactive compounds (유자(Citrus junos)씨와 유자씨 유지의 메탄올 추출물에 의한 HT-29 대장암 세포 생장 억제 효과 및 유효 성분 분석)

  • Kim, Kyungeun;Cho, Hyunnho;Jung, Hana;Lee, Hee Jae;Hwang, Keum Taek
    • Korean Journal of Food Science and Technology
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    • v.49 no.3
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    • pp.242-251
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    • 2017
  • The purpose of this study was to investigate the anti-proliferative effect of methanolic extracts from Citrus junos (yuja) seeds and yuja seed oils against HT-29 human colon cancer cells and to identify the key compounds responsible for this effect. Extracts from yuja seeds, yuja seed oil prepared using hexane, and cold-pressed yuja seed oil were prepared using 60% methanol (ES, EHO, and ECO, respectively). The key compounds in the extracts were determined using HPLC-MS. Among the extracts, EHO and ECO inhibited proliferation of HT-29 cells. EHO and ECO were fractionated using preparative LC and the bioactive compounds were determined. Five of the fractions showed a significant anti-proliferative effect and the main compounds in the fractions were isopimpinellin, bergapten, and ichangensin. These compounds showed anti-proliferative effects on HT-29 cells when treated individually, and ichangensin showed the highest anti-proliferative activity. These results suggest that these compounds may be responsible for the anti-cancer effect of EHO and ECO.