• 제목/요약/키워드: xanthotoxin

검색결과 19건 처리시간 0.023초

Monoamine Oxidase Inhibitory Coumarins from the Aerial Parts of Dictamnus albus

  • Jeong, Seon-Hwa;Han, Xiang Hua;Hong, Seong-Su;Hwang, Ji-Sang;Hwang, Ji-Hye;Lee, Dong-Ho;Lee, Myung-Koo;Ro,, Jai-Seup;Hwang, Bang-Yeon
    • Archives of Pharmacal Research
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    • 제29권12호
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    • pp.1119-1124
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    • 2006
  • The methanol extract from the aerial parts of Dictamnus albus was active in inhibiting monoamine oxidase (MAO) from the mouse brain. Activity-guided fractionation led to the isolation of four known coumarins, 7-(6'R-hydroxy-3', 7'-dimethyl-2'E, 7'-octadienyloxy) coumarin (1), auraptene (2), umbelliferone (3), and xanthotoxin (4), as active compounds along with an inactive alkaloid, skimmianine (5). Compounds 1 and 2 inhibited MAO activity in a concentration-dependent manner with $IC_{50}$ values of 0.7 and $1.7\;{\mu}M$, respectively. Compounds 1 and 2 showed a slight and potently selective inhibitory effect against MAO-B ($IC_{50}\;0.5\;and\;0.6\;{\mu}M,\;respectively$) compared to MAO-A ($IC_{50}\;1.3\;and\;34.6\;{\mu}M,\;respectively$). According to kinetic analyses derived by Lineweaver-Burk reciprocal plots, compounds 1 and 2 exhibited a competitive inhibition to MAO-B.

The Constituents Isolated from Peucedanum japonicum Thunb. and their Cyclooxygenase (COX) Inhibitory Activity

  • Zheng, Mingshan;Jin, Wenyi;Son, Kun-Ho;Chang, Hyeun-Wook;Kim, Hyun-Pyo;Bae, Ki-Hwan;Kang, Sam-Sik
    • 한국약용작물학회지
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    • 제13권2호
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    • pp.75-79
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    • 2005
  • Five coumarins, psoralen (1), scopoletin (2), isoimperatorin (4), (+)-marmesin (5) and xanthotoxin (6), three chromones, cimifugin (3), hamaudol (7) and sec-O-glucosylhamaudol (10), one sterol, daucosterol (8) and one aliphatic alcohol, galactitol (9) were isolated from the root of Peucedanum japonicum. Their chemical structures were identified by the physicochemical and spectroscopic data by comparing literature values. Among them, compounds 9 and 10 were isolated for the first time from this plant. The anti-inflammatory effects of isolated compounds were examined on cyclooxygenase (COX), compounds 1, 2 and 7 showed inhibitory activity on COX-1 with $IC_{50}$ values of 0.88, 0.27 and 0.30 mM, respectively. In the test for COX-2 activity, only compound 7 showed significant inhibitory activity with the $IC_{50}$ value of 0.57 mM. The other compounds exhibited weak inhibitory or no inhibitory activity.

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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    • 제66권
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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.

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

  • 최희철;노태철;김보연;고학룡;오원근;성창근;민태익;안종석;이현선
    • 생약학회지
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    • 제30권2호
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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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쿠마린에 의한 RAW 264.7 세포주의 Nitric Oxide 생성 저해활성 (Inhibitory Effect of Coumarins on Nitric Oxide Production in LPS-Activated Murine Macrophages)

  • 노태철;최희철;김보연;김영호;안종석;김영국;이현선
    • 생약학회지
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    • 제30권4호
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    • pp.413-416
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    • 1999
  • During the screening for inhibitors on nitric oxide (NO) production in LPS-activated murine macrophage, RAW 264.7 cells, two coumarins were isolated from chloroform extract of Ponciri Fructus. They were identified as imperatorin (10), phellopterin (11) on the basis of spectroscopic methods. The $IC_{50}$ values for NO formatiom were about $5.4\;{\um}M$ and $35.0\;{\um}M$, respectively, and then eleven coumarins were tested for the inhibitory effects on NO production in activated macrophages. All the test coumarins inhibited NO production in concentration-dependent manner and furanocoumarins (6-11) showed much more potent inhibitory effect than simple coumarins. Among the compounds examined xanthotoxin (8) was the most potent inhibitors of NO production $(IC_{50}=1.4\;{\mu}M)$. Analysis of the structure-activity relationship among these coumarins led to the conclusion that the substitution of C-5 position in furanocoumarins reduces greatly their inhibitory potency although the substitution of C-8 does not almost affect it.

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방풍의 화학 성분 (Chemical Constituents of Saposhnikovia divaricata)

  • 김소준;진영원;윤기동;류민열;양민혜;이제현;김진웅
    • 생약학회지
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    • 제39권4호
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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.

Chemical Constituents of the Root of Dystaenia takeshimana and Their Anti-Inflammatory Activity

  • Kim, Ju-Sun;Kim, Jin-Cheul;Shim, Sang-Hee;Lee, Eun-Ju;Jin, Wen-Yi;Bae, Ki-Hwan;Son, Kun-Ho;Kim, Hyun-Pyo;Kang, Sam-Sik;Chang, Hyeun-Wook
    • Archives of Pharmacal Research
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    • 제29권8호
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    • pp.617-623
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    • 2006
  • In our ongoing search for bioactive compounds originating from the endemic species in Korea, we found that the hexane and EtOAc fractions of the MeOH extract from the root of Dystaenia takeshimana (Nakai) Kitagawa (Umbelliferae) showed cyclooxygenase-2 (COX-2) and 5- lipoxygenase (5-LOX) dual inhibitory activity by assessing their effects on the production of prostaglandin $D_2\;(PGD_2)$ and leukotriene $C_4\;(LTC_4)$ in mouse bone marrow-derived mast cells. By activity-guided fractionation, five coumarins, viz. psoralen (2), xanthotoxin (3), scopoletin (4), umbelliferone (5), and (+)-marmesin (6), together with ${\beta}-sitosterol$ (1), were isolated from the hexane fraction, and two phenethyl alcohol derivatives, viz. 2-methoxy-2-(4'-hydroxyphenyl)ethanol (7) and 2-hydroxy-2-(4'-hydroxyphenyl)ethanol (8), three flavonoids, viz. apigenin (9), luteolin (10), and cynaroside (11), as well as daucosterol (12) were isolated from the EtOAc fraction using silica gel column chromatography. In addition, D-mannitol (13) was isolated from the BuOH fraction by recrystallization. Two of the coumarins, scopoletin (4) and (+)- marmesin (6), the two phenethyl alcohol derivatives (7, 8) and the three flavonoids (9-11) were isolated for the first time from this plant. Among the compounds isolated from this plant, the five coumarins as well as the three flavonoids showed COX-2/5-LOX dual inhibitory activity. These results suggest that the anti-inflammatory activity of D. takeshimana might in part occur via the inhibition of the generation of eicosanoids.

Antibacterial compounds against fish pathogenic bacteria from a combined extract of Angelica gigas and Artemisia iwayomogi and their quantitative analyses

  • Lim, Jae-Woong;Kim, Na Young;Seo, Jung-Soo;Jung, Sung-Hee;Kang, So Young
    • Fisheries and Aquatic Sciences
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    • 제24권10호
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    • pp.319-329
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    • 2021
  • In the search for antibiotic alternatives from safe and effective medicinal plants against fish pathogenic bacteria, we found that a combined extract (CE) of 1:1 (w/w) ratio of Angelica gigas Nakai roots and aerial parts of Artemisia iwayomogi Kitamura showed antibacterial activity against the fish pathogenic bacteria. By antibacterial activity-guided fractionations and isolations, five compounds were isolated and identified as decursinol angelate (1), decursin (2), xanthotoxin (3), demethylsuberosin (4), and 2,4-dihydroxy-6-methoxyacetophenone (5) through spectroscopic analyses, such as nuclear magnetic resonance (NMR) and mass spectrometry (MS). Among the compounds, 1 and 2 showed the highest antibacterial activities against Streptococcus iniae and Vibrio anguillarum, showing minimum inhibitory concentrations (MICs) of 62.5-250 ㎍/mL. Compounds 3, 4, and 5 were also found to be active, with MICs of 31.25-1,000 ㎍/mL for those strains. Furthermore, active compounds, 1 and 2 in CE were simultaneously quantified using high-performance liquid chromatography-tandem MS (HPLC-MS/MS). The average contents of 1 and 2 in CE was 3.68% and 6.14%, respectively. The established method showed reliable linearity (r2 > 0.99), good precision, accuracy, and specificity with intra- and inter-day variations of < 2 % and recoveries of 90.13%-108.57%. These results may be helpful for establishing the chemical profile of CE for its commercialization as an antibiotic alternative in aquaculture.

사삼(沙蔘)에 관(關)한 문헌적(文獻的) 고찰(考察) (Bibliographical studies on the shashen(Adenophora triphylla var. Japonica Hara.))

  • 신동훈;서영배
    • 혜화의학회지
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    • 제8권2호
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    • pp.107-122
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    • 2000
  • As a result of studing on the "shashen(沙蔘)", we could reach conclusions as follows. 1. Shashen is the root of "lunyeshashen(潤葉沙蔘)", "kuoyeshashen(闊葉沙蔘)", and its same generic plants that belong to Companulaceae. In china people has used twenty-four species as a shashen together with other generic plants, in korea sixteen species as a shashen. 2. At first, in the "Shen Nong's Herbal(神農本草經)" it was recorded and then in the "Benchingfengyuan(本經逢原)" divided into "nanshashen(南沙蔘)" and "beishashen(北沙蔘)". Recently, nanshashen called shashen belongs to Companulaceae and have strong efficacies of clearing away heat from lung, resolving phlegm, beishashen belongs to Umbelliferae and have strong efficacies of nourishing stomach, nourishing yin. 3. Shashen is the root of Adenophora stricta Miq., and yangru(羊乳) is that of Codonopsis lauceolata Bentham et Hooker, jini is that of Adenophora remotiflora (SIEBOLD et ZUCCARINI.) MIQUEL. From a efficacious point of view, it is the characteristics that shashen have efficacies of nourishing yin and clearing away heat from lung, supplementing stomach and promoting production of body fluid, resolving phlegm and relieving cough, eliminating pus and abscess, expelling wind and pruritus, jini have those of clearing away heat and toxic material, resolving phlegm and yanru have those of nourishing yin and moistening lung, resolving phlegm and eliminating pus, clearing away heat and toxic material, stimulating milk secretion. 4. After being recorded as "zhimu(知母)" in Shen Nong's Herbal, the alias of shashen was recorded as kuxin(苦心), shimei(識美), huxu(虎須), baishen(白參), zhiqu(志取), wenhu(文虎), baolishen(保利參), paoshen(泡參), jibantui(鷄半腿), yangponai(羊婆妨) and so on. Moreover shashen was named after its characteristics of that it grows well in the sandy soil and as a wushen(五參) with a renshen(人蔘) its form is different from that of wushen but their chief virtues are alike. 5. In the numerous medical books, xinyeshashen(杏葉沙蔘) regarded as nanshashen. It was called as the alias of jini, so I thouhgt that it was wrong xinyeshashen to be regarded as nanshashen. 6. It was used shashen for renshen, renshen was used to treat lung-cold syndrome by its efficacy of tonifying yang and shashen lung-heat syndrome by its efficacy of nourishing yin, the reasons of that because shashen had amount of sap, its properies and flavours of herbs are light and clean. 7. The constituents of shashen were essential oil, starch, shashen-saponin, furocoumarin, xanthotoxin(ammoidin), inulin, sugar, mucus and have efficacies of resolving phlegm, promoting production of body fluid, immunomodulational and antibiotic efficacies. above results indicated that the origin of shashen and substitutional plants was various. Their efficacies are somewhat alike, but there were characteristic efficacies each other. Nowadays they are used together with, so we should know the characteristic efficacies of them and then we using them clinically, more deep discrimination and experimental support shoud be accomplished.

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