• Title/Summary/Keyword: Isoimperatorin

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Antifungal activities of coumarins isolated from Angelica gigas and Angelica dahurica against Plant pathogenic fungi (당귀와 백지로부터 분리한 Coumarin계 물질들의 식물병원균에 대한 항균활성)

  • Ryu, Shi-Yong;Kim, Young-Sup;Kim, Heung-Tae;Kim, Seong-Ki;Choi, Gyung-Ja;Kim, Jeoung-Seob;Lee, Seon-Woo;Heor, Jung-Hee;Cho, Kwang-Yun;Kim, Jin-Cheol
    • The Korean Journal of Pesticide Science
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    • v.5 no.3
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    • pp.26-35
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    • 2001
  • In order to search potent antifungal substances from domestic plants, 40 plants cultivated in Korea were collected. After extracting with methanol (MeOH) and concentrating to dryness, the MeOH extracts were screened for in vivo antifungal activity against six plant diseases at a concentration of $2000{\mu}g/mL$. Fourteen extracts showed disease-controlling activity more than 90% against at least one of the 6 plant diseases tested; eight, seven, and three extracts controlled more than 90% the development of rice blast, tomato late blight, and wheat leaf rust, respectively. However, none of the extracts exhibited in vivo antifungal activity more than 90% against rice sheath blight, tomato gray mold, and barley powdery mildew. From the MeOH extracts of Angelica gigas and A. dahurica showing potent controlling activity against rice blast, 1 and 2 antifungal substances, respectively, were isolated by solvent partitioning and column chromatography. The three compounds were identified to be coumarins, namely, decursin, imperatorin, and isoimperatorin, by mass spectrometry and NMR spectroscopy. They were examined for in vitro and in vivo antifungal activities together with umbelliferone (7-bydroxycournarin) and scopoletin (6-methoxy-7-hydroxycoumarin) containing a free hydroxyl group at position 7 to investigate the structure-activity relationship. In vitro, most of 50% growth inhibitory concentrations ($IC_{50}$) were over $200{\mu}g/mL$, indicating that they have relatively weak antifungal activity. The antifungal activity of decursin and scopoletin, containing cyclic alkoxy groups instead of free hydroxyl group at position 7, was stronger than umbelliferone and scopoletin. Especially, decursin and imperatorin showed potent antifungal activities against Pythium ultimum and Magnaporthe grisea, respectively, with $IC_{50}$ values less than $25{\mu}g/mL$. In vivo, decursin and imperatorin showed potent antifungal activity against rice blast, whereas other coumarins hardly controlled the development of 6 plant diseases tested. These results suggest that the antifungal activity of 7-hydroxycoumarin derivative is substantially increased when the hydroxyl group at position 7 is protected by a stable cyclic alkoxy grouping.

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Method validation of marker compounds from Angelicae Dahuricae Radix as functional food ingredients (건강기능식품 원료로서 구릿대의 지표성분 분석법 검증)

  • Bo-Ram Choi;Dahye Yoon;Hyeon Seon Na;Geum-Soog Kim;Kyung-Sook Han;Sookyeong Lee;Dae Young Lee
    • Journal of Applied Biological Chemistry
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    • v.65 no.4
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    • pp.343-348
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    • 2022
  • This study was performed to establish an analytical method for the standardization of Angelicae Dahuricae Radix as a functional ingredient. We established six compounds including oxypeucedanin hydrate (1), byakangelcol (2), oxypeucedanin (3), imperatorin (4), phellopterin (5) and isoimperatorin (6) as marker compounds of Angelicae Dahuricae Radix. An analytical method using Ultra Performance Liquid Chromatography (UPLC) was established and validated for marker compounds of Angelicae Dahuricae Radix. The specificity was confirmed by the chromatogram from UPLC and the value of coefficient determination was also higher than 0.999, indicating high linearity. The relative standard deviation (RSD) and recovery of marker compounds were less than 5% and in the range of 90- 110%, respectively, which means that this method has high accuracy and precision. Therefore, this analytical method could be used as basic data for the development of functional ingredients for health functional food of Angelicae Dahuricae Radix.

Effects of Furanocoumarins from Angelica Dahurica on Aldose Reductase and Galactosemic Cataract Formation in Rats

  • Shin, Kuk-Hyun;Chung, Myung-Sook;Cho, Tae-Soon
    • Archives of Pharmacal Research
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    • v.17 no.5
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    • pp.331-336
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    • 1994
  • The ether extract from the roots of angelica clahurica was found to inhibit bovine lens aldose reductase (BLAR0 activity in vitro by 100% at 100.mu.g/ml. Systematic fractionation of the ether soluble fraction and subsequent active frctions monitorede by bioassy led to isolation of four furanocoumarins, isoimperatorin (I0, imperatorin (II), ter-O-methyl byakangelicin (III) and byakangelicin (IV), among which compound III and IV were identified as potential AR inhibitors, their $IC_{50}$ values being $2.8{\mu}M{\;}and{\;}6.2{\mu}M$, respectively. Galactosemic cataract formation tors, in rats treated with 40 g/kg/day of galactose was blocked almost completely throughout the exeprimental periods up to 44 days by i.p. administrations of byakangelicin (IV) at 50 mg/kg/day. In coincidence with the inhibitory action on cataract formation, the galactitol accumulation in rats treated with byakangelicin (IV) was found to be markedly prevented by approximately 80.5% compared to those of the contro. These results indicate that byakangelicin (IV), as a main principle of this plant, possesses high potential for a clinically useful drug of the future which prevents and/or improves sugar cataract as well as diabetic complications.

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Coumarins and Chromones from Angelica genuflexa

  • An, Ren-Bo;Park, Bo-Young;Kim, Jung-Hee;Kwon, Ok-Kyoung;Lee, Joong-Ku;Min, Byung-Sun;Ahn, Kyung-Seop;Oh, Sei-Ryang;Lee, Hyeong-Kyu
    • Natural Product Sciences
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    • v.11 no.2
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    • pp.79-84
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    • 2005
  • Thirteen compounds were isolated from the roots of Angelica genuflexa through repeated silica gel column chromatography. Nine coumarins, isoimperatorin (1), osthol (2), demethylsuberosin (3), oxypeucedanin (4), heraclenin (5), pabulenol (7), umbelliferone (8), oxypeucedanin hydrate (9) and marmesinin (11), and four chromones, hamaudol (6), cimifugin (10), sec-O-glucosylhamaudol (12) and prim-O-glucosylcimifugin (13), were identified by physicochemical and spectroscopic analysis. Among these, compounds 3, 5, 6, 8, 12, and 13 were isolated for the first time from the roots of Angelica genuflexa. These coumarins and chromones were examined for their anticomplement activity. Demethylsuberosin (3) showed a weak anticomplement activity with an $IC_{50}$ value of $390\;{\mu}M$.

Screening of Bioconversion Components from Gumiganghwal-tang on Fermentation by Lactobacillus Strains

  • Liang, Chun;Lee, Kwang Jin;Cho, Chang-Won;Ma, Jin Yeul
    • Natural Product Sciences
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    • v.20 no.2
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    • pp.102-106
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    • 2014
  • Gumiganghwal-tang (GMT) is a traditional herbal prescription used for treatment of the common cold, pain, and inflammatory diseases. Variations in the amounts of bioactive components of GMT and GMT fermented with 10 Lactobacillus strains were investigated by high-performance liquid chromatography coupled with diode array detection (HPLC-DAD). Simultaneous qualitative and quantitative analyses of eleven bioactive compounds (prim-O-glucosylcimifugin, liquiritin, cimifugin, baicalin, liquiritigenin, wogonoside, baicalein, wogonin, butylphthalide, imperatorin, and isoimperatorin) were performed, with comparison of their retention times (tR) and UV spectra with those of standard compounds. The amounts of baicalin (8.71 mg/g), liquiritigenin (5.28 mg/g) and butylphthalide (5.10 mg/g) were the major compounds in GMT. We found that L. fermentum KFRI 145 fermented wogonoside and baicalin to their aglycones, wogonin and baicalein, respectively. These results indicated that L. fermentum KFRI 145 has potential as a functional starter culture for manufacturing fermented GMT.

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
    • Korean Journal of Medicinal Crop Science
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    • v.13 no.2
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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.