• Title/Summary/Keyword: sesquiterpene lactones

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Antimicrobial Activities of Sesquiterpene Lactones Isolated from Hemisteptia lyrata, Chrysanthemum zawadskii and Chrysanthemum boreale (지칭개, 구절초 및 산국에서 분리한 Sesquiterpene lactones의 항균활성)

  • Jang, Dae-Sik;Park, Ki-Hun;Lee, Jong-Rok;Ha, Tae-Joung;Park, Yun-Bae;Nam, Sang-Hae;Yang, Min-Suk
    • Applied Biological Chemistry
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    • v.42 no.2
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    • pp.176-179
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    • 1999
  • In the bioactivity test of nine sesquiterpene lactons isolated from Hemisteptia lyrata, Chrysanthemum zawadskii and Chrysanthemum boreale, we investigated their antimicrobial activities against ten bacteria and six phytopathogenic fungi. Hemistepsin A and hemistepsin B isolated from H. lyrata and tulipinolide isolated from C. boreale exhibited strong antibacterial activity. In the antifungal test, hemistepsin B, angeloylcumambrin B, tigloylcumambrin B and costunolide showed broad activity. Both antibacterial and antifungal experiments exhibited quite clear specificity against microbial strains.

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Isolation of Guaianolides with ACAT Inhibitory Activity from the Leaves and Stems of Chrysanthemum boreale Makino (산국의 잎과 줄기에서 ACAT 저해활성을 가지는 Guaianolides의 분리)

  • Lee, Jong Rok;Park, Moon Ki
    • Journal of Environmental Science International
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    • v.26 no.11
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    • pp.1275-1284
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    • 2017
  • Acyltransferase (AT) catalyzes the transfer of an acyl moiety from acyl-coenzyme A (acyl-CoA) to an acceptor. ATs play important roles in the maintenance of homeostasis in the human body and have been linked to various diseases; therefore, several ATs have been proposed as potential targets for the treatment or prevention of such diseases. The AT family includes acyl-CoA:cholesterol AT (ACAT), diacylglycerol AT, and monoacylglycerol AT for the metabolism of lipids. Furthermore, recent molecular biological studies revealed the existence of their isozymes with distinct functions in the body. ACAT plays a critical role in the formation of cholesteryl esters from cholesterol and fatty acids, and is a potential target for treating hypercholesterolemia. During an experiment designed to discover biologically active compounds from herbal medicines, we isolated two known guaianolide sesquiterpene lactones from Chrysanthemum boreale Makino (Compositae). The lactones were characterized from their spectroscopic data (NMR, IR, MASS). These compounds were subjected to ACAT inhibition assay. Here, we report the isolation and structural elucidation of the compounds 8-o-acetyl-2-methoxy-10-hydroxy-3,11(13)-guaiadiene-12,6-olide and 8-acetyl-3,10-hydroxy-4(15),11(13)-guaiadiene-12,6-olide. In the ACAT inhibition assay, compound 1 showed strong inhibitory activity, with an $IC_{50}$ value $45{\mu}g/mL$, whereas compound 2 did not exhibit significant inhibitory activity with an over $100{\mu}g/mL$.

Variation of Selected Phenotypic Characteristics, Anthocyanins and Bitter Sesquiterpene Lactones in Lettuce (Lactuca sativa L.) Germplasm (상추(Lactuca sativa L.)유전자원의 형태 특성 및 Anthocyanins과 Bitter Sesquiterpene Lactones 변이)

  • Choi, Susanna;Assefa, Awraris Derbie;Lee, Jae-Eun;Hur, On-Sook;Ro, Na-Young;Lee, Ho-Sun;Noh, Jae-Jong;Hwang, Ae-Jin;Kim, Yeong-Jee;Kim, Bich-Saem;Ko, Ho-Cheol;Rhee, Ju-Hee
    • Proceedings of the Plant Resources Society of Korea Conference
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    • 2019.10a
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    • pp.95-95
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    • 2019
  • 상추(Lactuca sativa L.)는 대표적인 쌈 및 샐러드 채소로 우리나라 기준(2016년) 3,387 ha의 면적에서 86,128톤을 생산하여 엽채류 중 배추, 양배추 다음으로 많이 생산되는 작물이다. 안토시아닌(Anthocyanins)은 열매, 꽃, 줄기, 잎 등 식물계에 널리 분포되어 있는 페놀 화합물 중 하나로 적색, 자색 등의 색을 나타내는 수용성 flavonoid계 색소이다. BSLs (Bitter sesquiterpene lactones)는 항암, 항균, 해열과 염증완화에 효과가 있는 것으로 알려져 있다. 본 연구는 농촌진흥청 농업유전자원센터에서 보유 중인 상추 66자원의 형태학적 특성 및 액체크로마토그래피(HPLC, UPLC)를 이용한 안토시아닌과 BSLs성분을 분석하여 함량이 높은 자원을 선발하고자 한다. 상추시료 0.05 g을 $MeOH/H_2O/AcAc$로 추출 한 후, UPLC를 사용하여 안토시아닌 함량을 분석하였으며, 상추시료 0.25 g을 100% MeOH로 추출 한 후 HPLC를 사용하여 BSLs 함량을 분석하였다. 연구 결과, 상추 유전자원의 안토시아닌 함량 범위는 0 mg/100 g에서 371.94 mg/100 g이고, BSLs성분 함량 범위는 $60.28{\mu}g/g\;DW$에서 $2821.92{\mu}g/g\;DW$ 이었다. 상추 66자원 중 안토시아닌함량이 200 mg/100 g이상인 자원은 IT217012, IT218395, IT231524, IT231525, IT260852이며, BSLs 함량이 $1700{\mu}g/g\;DW$이상인 자원은 IT231524, IT231525, IT231527, IT264971, IT271118이다. 두 성분의 함량이 모두 높은 자원 IT231524와 IT231525 이었다. 이 두자원의 형태적 특성은 초형이 잎상추로 잎이 넓은 타원형에 가장자리 결각이 강한 자주색이다. 따라서 본 연구는 다양한 상추 유전자원의 형태학적 특성 및 BSLs, 안토시아닌 성분이 높은 자원을 선발하여 육종소재로 활용하고자 한다.

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Variation in Phenotypic Characteristics and Contents of Sesquiterpene Lactones in Lettuce (Lactuca sativa L.) Germplasm

  • Sung, Jung-Sook;Hur, On-Sook;Ryu, Kyoung-Yul;Baek, Hyung-Jin;Choi, Susanna;Kim, Sang-Gyu;Luitel, Binod Prasad;Ko, Ho-Cheol;Gwak, Jae-Gyun;Rhee, Ju-Hee
    • Korean Journal of Plant Resources
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    • v.29 no.6
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    • pp.679-689
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    • 2016
  • Lettuce is an important annual leafy vegetable and bitterness is its potent flavor character. Lettuce germplasm differ their phenotypic characters and sesquiterpene lactones (SLs) contents which are important for consumer's acceptance. This study was carried out to evaluate the phenotypic characters and SLs contents in one hundred lettuce germplasm in Jeonju, Korea. Twenty-three agro-morphological (16 qualitative and 7 quantitative) traits and two SLs (lactucin and lactucopicrin) contents were studied in these germplasm. Germplasm exhibited the variation in qualitative and quantitative characters. Average plant weight was 423.9 g with a range from 116.0 to 905.0 g. Lactucin content was varied from 19.7 (IT 294226) to $194.4{\mu}g/g$ (IT 294298) with an average concentration of $84.7{\mu}g/g$. Lactucopicrin ranged from 82.5 (IT 300134) to $2228.6{\mu}g/g$ (IT 294210) with an average concentration of $586.3{\mu}g/g$. Total SLs content was ranged from 120.1 (IT 300134) to 2286.6 (IT 294210)${\mu}g/g$ with the average concentration of $671.0{\mu}g/g$. Significant ($p{\leq}0.05$) differences were found between crisp head and butter head germplasm for lactucin, lactucopicrin and total SLs content. Crisp head germplasm revealed the highest average lactucin ($112.9{\mu}g/g$), lactucopicrin ($734.8{\mu}g/g$) and total SLs content ($847.7{\mu}g/g$). Crisp head and leafy type germplasm exhibited more total SLs content (847.7 and $744.7{\mu}g/g$, respectively) than cos ($524.9{\mu}g/g$) and butter head type ($519.4{\mu}g/g$). Principal component analyses of the quantitative traits indicated that the first principal component axis accounted more than 91% of the total variation. This study revealed the ample genetic variation in the agro-morphological traits and SLs contents to support the selection for improved lettuce varieties.

Isolation of Magnolialide and Artesin from Cichorium intybus: Revised Structures of Sesquiterpene Lactones

  • Park, Hee-Juhn;Kwon, Sang-Hyuk;Yoo, Ki-Oug;Jung, Won-Tae;Lee, Kyung-Tae;Kim, Joo-Il;Han, Yong-Nam
    • Natural Product Sciences
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    • v.6 no.2
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    • pp.86-90
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    • 2000
  • Two known eudesmanolides, magnolialide and artesin, were isolated from the roots of Cichorium intybus. Their structures were confirmed by HMBC and NOESY NMR spectral interpretation. Therefore, guaianolides and eudesmanolides that have been previously reported should be revised.

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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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Studies on Essential Oils of Plants of Angelica Genus in Korea(V) -Essential Oils of the Root of Angelica decursiva- (Angelica속 생약의 정유성분에 관한 연구(V) -바디나물의 정유성분-)

  • Chi, Hyung-Joon;Kim, Hyun-Soo
    • Korean Journal of Pharmacognosy
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    • v.24 no.3
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    • pp.192-196
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    • 1993
  • Essential oil of the root of Angelica decursiva(Miq.) Fr. et Sav. (Umbelliferae) was investigated. Essential oil was obtained from the dried roots by steam distillation and fractionated by column chromatography. Each isolate or fraction was identified by GC, GC-MS and spectral analysis. It was found to contain ten monoterpenes such as ${\alpha}-pinene$ (7.0%) etc. Three hydrocarbons, two aldehydes, three sesquiterpenes, two sesquiterpene alcohols, one aromatic compounds, one ketone, isobonyl acetate and two lactones were tentatively identified.

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Intraplant Variations of Sesquiterpene Lactone Content in Lettuce Genetic Resources Grown in Two Cultivation Seasons

  • Assefa, Awraris Derbie;Choi, Susanna;Sung, Jung-Sook;Hur, On-Sook;Ro, Na-Young;Lee, Sok Young;Lee, Ho-Sun;Lee, Jae Eun;Rhee, Ju-Hee
    • Korean Journal of Plant Resources
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    • v.31 no.5
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    • pp.538-546
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    • 2018
  • Inflorescence, stem, and leaf samples of lettuce grown in a greenhouse in spring and autumn seasons were assayed for sesquiterpene lactones (SLs) content by high performance liquid chromatography. The concentrations of SLs were significantly higher in the inflorescences followed by upper leaf and stem compared to the other plant parts in most of the samples. SLs content (sum of lactucin and lactucopicrin) in various tissues of lettuce cultivated in spring season varied from 5.7 to 22.5 fold ranging from $27.4{\mu}g/g$ dry weight (DW) in the upper stem (cultivar "PI 176588") as the lowest to as high as $2,292.0{\mu}g/g$ DW in the inflorescence (cultivar "709849-1"). During autumn cultivation, the concentration of SLs varied from 2.0 to 14.4 fold ranging from as low of $32.4{\mu}g/g$ DW in the lower stem (cultivar "PI176588") to as high of $838.0{\mu}g/g$ DW in the upper leaf (cultivar "Dambaesangchu"). Higher lactucin (1.2 to 5.6 fold) and lactucopicrin (1.1 to 3.9 fold) concentration was observed during spring compared to autumn cultivation in most of the samples. SLs content in various organs of lettuce increases from the basal plant part going upwards. As lactucin and lactucopicrin are the major SLs which affects the sensory property of lettuce, their quantitative variation in the lettuce cultivars is useful for breeding new varieties with better consumer acceptance.