• Title, Summary, Keyword: Chrysanthemum boreale Makino

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Germacranolides from Flowers of Chrysanthemum boreale Makino (산국 꽃의 Germacranolides)

  • Jang, Dae-Sik;Park, Ki-Hun;Yang, Min-Suk
    • Korean Journal of Pharmacognosy
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    • v.29 no.2
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    • pp.67-70
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    • 1998
  • Two sesquiterpene lactones were isolated from the flowers of Chrysanthemum boreale Makino by the silica gel column chromatography and recrystallization. On the basis of spectrometric studies including $^1H-NMR,\;^{13}C-NMR,\;DEPT,\;^1H-^1H\;COSY,\;{13}C-^1H\;COSY$, IR and Mass, compounds 1 and 2 were identified as germacranolide, tulipinolide and costunolide, respectively. And they showed antibacterial activity against Vibrio parahaemolyticus, Bacillus subtilis, Bacillus cereus and Staphylococcus aureus. This is the first report that Chrysanthemum boreale contained tulipinolide and costunolide.

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Structural Analysis and Biological Activities of Sesquiterpene Lactones Isolated from the Leaves and Stems of Chrysanthemum boreale Makino (산국의 잎과 줄기에서 분리한 Sesquiterpene Lactone들의 구조규명 및 생리활성)

  • Lee, Jong Rok;Park, Moon Ki
    • Journal of Environmental Science International
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    • v.26 no.11
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    • pp.1285-1295
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    • 2017
  • Chrysanthemum boreale Makino is widely distributed in Korea, China, Japan and Southeast Asian countries. C. boreale is one of the herbs used for treating various inflammatory diseases in oriental medicine. The present study was conducted to identify biologically active compounds from the leaves and stems of C. boreale. We isolated two sesquiterpene sactones from the leaves and stems of C. boreale using silica gel column chromatography and recyclic high perfomance liquid chromatography. The lactones were characterized by their spectroscopic data (NMR, IR, MASS). These compounds were subjected to Farnesyl Protein Transferase (FPTase) inhibition, Nitric Oxide (NO) release inhibition and apoptosis inhibition. The structur of the following isolated compound were elucidated 8,10-${\small{O}$-Acetyl-2-methoxy-10-hydroxy-3,11(13)-guaiadiene-12,6-olide and 4,10-dihydroxy-8-${\small{O}$-Acetyl-2,11(13)-guaiadiene-12,6-olide. In the NO release inhibition assay, compound 2 showed strong activities, with an $IC_{50}$ value of $7{\mu}g/mL$, whereas compound 1 did not exhibit significant activity with an $IC_{50}$ value of over $14{\mu}g/mL$ against murine macrophage.

Induction of Apoptosis in Human Oral Epidermoid Carcinoma Cells by Essential Oil of Chrysanthemum boreale Makino

  • Cha, Jeong-Dan;Jeong, Mi-Ran;Lee, Young-Eun
    • Food Science and Biotechnology
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    • v.14 no.3
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    • pp.350-354
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    • 2005
  • The effect of the essential oil obtained from Chrysanthemum boreale Makino on the apoptosis of KB cells was investigated. Cytotoxicity and cellular DNA content were analyzed by MTT assay, flow cytometry, agarose gel electrophoresis, and Hoechst 33258 staining. The caspase-3 and poly (ADP-ribose) polymerase (PARP) proteins were estimated by Western blotting method. The various cytotoxic effects of the essential oil which are hallmarks of apoptosis, including DNA fragmentation, apoptotic body formation, and sub-G1 DNA content, all progressed in a dose-dependent manner. Treatment with an apoptosis-inducing concentration of the essential oil caused rapid and transient induction of caspase 3 activity. Further, the efficacious induction of PARP cleavage and caspase-3 activation was observed at an essential oil concentration of 0.1 and 0.2 mg/mL for 12 hr.

Cumambrin A in Chrysanthemum boreale Makino Preparation, X-ray Crystal Structure and $^{13}C-$ and $^1H$-NMR Study of Cumambrin A

  • Park, Ki-Hun;Jang, Dae-Sik;Choi, Sang Uk;Nam, Sang-Hae;Shiro, Mooto;Yang, Min-Suk
    • Korean Journal of Pharmacognosy
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    • v.27 no.3
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    • pp.207-211
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    • 1996
  • Cumambrin A has been isolated from the dried flowers of Chrysanthemum boreale Makino. The complete $^1H$ and $^{13}C$ NMR assignment of cumambrin A was achieved from two-dimensional $^1H$-$^1H$ COSY and $^{13}C$-$^1H$ COSY spectra with the aid of homonuclear and heteronuclear double resonance experiments. The its structure has been verified by single crystal X-ray diffraction.

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Isolation and Characterization of Constituent Compounds from Leaves and Stems of Chrysanthemum boreale Makino (산국 잎과 줄기의 유효성분 분리 및 특성 연구)

  • Park, Sook Jahr;Park, Moon Ki;Lee, Jong Rok
    • Journal of Environmental Science International
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    • v.28 no.11
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    • pp.993-1004
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    • 2019
  • Chrysanthemum boreale Makino (C. boreale) is widely distributed in Asian countries, and has traditionally been used to treat various inflammatory diseases including bronchitis. In this study, we aimed to isolate biologically active compounds from leaves and stems of C. boreale. Chemical components were purified by column chromatograpy and recyclic HPLC, and characterized from their spectral data (IR, MS, NMR). Biological activity experiments were conducted for Farnesyl-protein transferase (FPTase) activity, apoptosis and nitirc oxide (NO) release. As a results, three sesquiterpene lactones were isolated. Compound 1 (4-methoxy-8-O-acetyl-10-hydroxy-2,11(13)-guaiadiene-12,6-olide) showed strong cytotoxic activities having an average growth inhibition of 50% ($GI_{50}$) value of $1.89{\mu}g/m{\ell}$ against human colon adenocarcinoma cells. Compound 1 also showed a low half maximal inhibitory concentration ($IC_{50}$) value of $10{\mu}g/m{\ell}$ for NO release. In the caspase 3 activity, compound 1 and compound 2 (8-O-(2-carbonyl-2-butyl)-3,10-dihydroxy-4,11(13) -guaiadiene-12,6-olide) exhibited 94% and 90% apoptosis inhibition activity, respectively. Compound 3 (4,8-O-diacetyl -10-hydroxy-2(3),11(13)-guaiadiene-12,6-olide) showed a strong inhibitory effect on FPTase activity with 90% inhibitory activity at a concentration of $100{\mu}g/m{\ell}$. These results clearly show the presence of lactone compounds in the leaves and stems, which may partially contribute to the pharmacological activity of C. boreale.

Isolation of ${\beta}-sitosterol$, Phytol and Zingerone $4-O-{\beta}-D-glucopyranoside$ from Chrysanthemum Boreale Makino

  • Kim, Dong-Hyun;Bang, Myun-Ho;Song, Myoung-Chong;Kim, Soon-Un;Chang, Young-Jin;Baek, Nam-In
    • Korean Journal of Medicinal Crop Science
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    • v.13 no.5
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    • pp.284-287
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    • 2005
  • The flowers of Chrysanthemum boreale Makino were extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with n-hexane, EtOAc, n-BuOH and $H_2O$. Two compounds from the n-hexane fraction and one glucoside from the n-BuOH fraction were isolated through the repeated silica gel and ODS column chromatographies. From the result of physico-chemical data including NMR, MS and IR, the chemical structures of the compounds were determined as ${\beta}-sitosterol$ (1), phytol (2) and zingerone $4-O-{\beta}-D-glucopyranoside$ (3). Compounds 2 and 3 were isolated for the first time from this plant.

Analysis of aroma components from flower tea of German chamomile and Chrysanthemum boreale Makino (국화과 허브류인 수입산 캐모마일차와 국내산 국화차의 향기성분 비교)

  • Im, Sung-Im;Bae, Jung-Eun;Choi, Sung-Hee
    • Korean journal of food and cookery science
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    • v.22 no.6
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    • pp.768-773
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    • 2006
  • The aroma components of german chamomile tea in Europe and kukwha (Chrysanthemum boreale Makino) tea in Korea belonging to genus chrysanthemum were analyzed and compared. The volatile components of chamomile tea and kukwha tea were collected by a simultaneous steam distillation-solvent extraction method (SDE). The extracted components were analyzed gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). Forty-six compounds, including cubebene(14.59%), ${\beta}$-elememe(4.88%) and ${\delta}$-cadinol(1.54%) were identified in chamomile tea. Forty-five compounds including santalol(6.25%), bomyl acetate(3.47%), farnesene(3.37%), 1,8-nonadiene (2.80%), caryophyllene oxide(2.77%) and thymol (2.16%) were identified in kukwha tea. Twenty-two compounds including 4-terpineol, ${\alpha}$-terpineol, thymol, phenylacetaldehyde, V-terpinene were found in both samples.

Isolation and Structure Elucidation of Radical Scavengers from Chrysanthemum boreale Makino (산국(山菊)의 자유라디칼 소거 물질 분리 및 동정)

  • Han, Wan-Soo
    • Korean Journal of Medicinal Crop Science
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    • v.11 no.1
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    • pp.1-4
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    • 2003
  • Two antioxidative compounds in Chrysanthemum boreale were isolated by a bioassay using a 2, 2-diphenyl-1-picrydrazyl(DPPH) free radical. They were identified as apigenin, linarin(acacetin-7-O-rutinoside) on the basis of $^1H\;and\;^{13}C-NMR$ and MS data. The DPPH radical scavenging activity$(RC_{50}:\;13.3{\mu}g)$ of apigenin was similar to that of ${\alpha}-tocopherol\;(12.1{\mu}g)$ and L-ascorbic acid$(13.1{\mu}g)$

Isolation of Angiotensin Converting Enzyme Inhibitors from Compositae Plants

  • Song, Kyung-Bin;Kim, Ji-youn;Jung, Hye-young
    • Preventive Nutrition and Food Science
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    • v.7 no.2
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    • pp.157-161
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    • 2002
  • Thirty plants of the Compositae family were screened for inhibitory activity of angiotensin converting enzyme (ACE). Among them, Chrysanthemum boreale Makino and Ixeris dentate Nakai were selected for further investigation since they had the highest inhibitory activity. Crude water extracts of the flowers of Chrysanthemum boreale Makino and the roots of Ixeris dentate Nakai were prepared by heating at 95$^{\circ}C$ and 6$0^{\circ}C$ for 2 hr, respectively, followed by centrifugation at 8000$\times$ g far 30 min. Crude extracts were then filtered using YM-3 and YM-1 membranes. The ACE inhibitors were isolated using consecutive chromatographic methods including: Sephadex G-15, ion exchange, FPLC, and reverse phase HPLC. The inhibitors were identified to have molecular masses of 204 and 283 daltons, respectively, by mass spectrometry. These results demonstrate that crude extracts of Compositae plants may be useful as functional food ingredients with anti-hypertensive properties.