• Title/Summary/Keyword: Sesquiterpene

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Molecular Cloning of a Partial Cadinane Synthase Gene from Artemisia annua

  • Song, Seung-hwan;Chang, Yung-jin;Kim, Jeong-gu;Kim, Soo-Un
    • Proceedings of the Korean Society of Applied Pharmacology
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    • 1998.11a
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    • pp.121-121
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    • 1998
  • Artemisia annua, an indigenous plant in Korea, contains a clinically important potent antimalarial principle, artemisinin. Artemisinin is a cadinane-type sesquiterpene endoperoxide. Cadinane synthase catalyzes the first committed step in artemisinin biosynthesis by cyclizing farnesyldiphosphate. In hopes of finding a cadinane synthase gene involved in artemisinin biosynthesis, oligonucleotides were synthesized on. the basis of the consensus nucleotide sequences and Nco I restriction sites for convenience in cloning. Specifically, nucleotide sequences of two highly conserved regions were deduced from the genes of similar function of Hyoscyamus muticus, Nicotiana tabacum, Abies grandis, Lycopersicon esculentum, and Gossypium hirsutum to construct a set of primers for polymerase chain reation (PCR). A 184 bp fragment was found to be amplified by PCR, and subsequently cloned. The gene revealed 62.8% identity in nucleotide and 55.6% in amino acid sequence to correspondent gene of N. tabacum. The gene was different from another sesquiterpene cyclase gene of A. annua, germacranadiene synthase gene, recently reported by Mercke and Bordelius (1998).

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VOLATILE FLAVOR COMPONENTS OF FRESH GINSENG (수삼의 휘발성 향기 성분)

  • Kim Man-Wook;Choi Kang-Ju;Wee Jae-Joon
    • Proceedings of the Ginseng society Conference
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    • 1984.09a
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    • pp.185-190
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    • 1984
  • Volatile flavor components of fresh ginseng (Panax ginseng C.A. Meyer) were studied by a combination of SE-54 fused silica capillary gas chromatography and mass spectrometry. Steam distillate of fresh ginseng roots was extracted with oxygen-free diethylether and concentrated. This aroma concentrate was separated into neutral, acidic, phenolic, and basic fractions. The neutral fraction, containing over two hundred compounds, was aromatically the closest to fresh ginseng with the key-flavor components predominantly being monoterpenes and sesquiterpenes. The sesquiterpene compounds were identified as being azulenic, menthenic, and napthalenic with a mass of 204.

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Sesquiterpene Pyridine Alkaloids from Euonymus japonica (사철나무의 알칼로이드 성분)

  • Ryu, Jae-Ha;Eun, Jin-Hee;Lee, So-Young;Chang, Joon-Shik;Park, Man-Ki;Park, Jeong-Hill;Han, Yong-Nam;Han, Byung-Hoon
    • YAKHAK HOEJI
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    • v.41 no.5
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    • pp.554-558
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    • 1997
  • Two alkaloidal components were isolated from the ether soluble part of the MeOH extract of the root bark of Euonymus japonica. Their structures were elucidated by the spe ctroscopic analylses as the sesquiterpene pyridine alkaloids derived from polyester sesquiterpenes which are characteristically detected in Celastraceae plants. These include macrocycle formed by two ester linkages between dihydro-${\beta}$-agarofuran nucleus and pyridinic dibasic acid(compound 1:evoninic acid, compound 2:wilfordic acid). The structure of compound $1[C_{47}H_{50}N_2O_{17},\;mp\;161{\sim}163^{circ}C$. $[{\alpha}]_D^{28}=+31.6^{\circ}$(c, 0.1 in EtOH)] was determined as novel structure named as euojaponine N, and compound $2[C_{48}H_{57}NO_{18},\;mp\;142{\sim}145^{circ}C,\;[{\alpha}_D^{27}=+27.0^{\circ}$(c, 0.1 in EtOH)] was identified as ebenifoline W-I reported from Maytenus ebenifolia.

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Antifungal Activities of Hemistepsin A and B Isolated from Hemistepita lyrata Bunge against Dandruff-causing Microbe Malassezia obutusa (지칭개에서 분리한 Hemistepsin A와 B의 비듬균에 대한 항균효과)

  • Lee, Jong Rok;Jung, Dae Hwa;Park, Moon Ki
    • KSBB Journal
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    • v.28 no.2
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    • pp.74-79
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    • 2013
  • There are a large number of bioactive sesquiterpene lactones from compositae plants including Hemistepita lyrata Bunge. In the present study, we purified two sesquiterpene lactones, Hemistepsin A and B, from H. lyrata and evaluated their antimicrobial activities against Malassezia obutusa. Chromatographic separation was used for the preparation of Hemistepsin A and B, and the identity of these compounds was confirmed by NMR. Strong inhibition of growth of M. obutusa was obtained with all doses of Hemistepsin A tested. Moreover, antifungal activity of Hemistepsin A occurred in a dose-dependent manner. Hemistepsin B also showed potent antifungal activity at the dose of $800{\mu}m/disc$. From these results, it was suggested that Hemistepsin A and B be beneficial for the preparation of the useful agent for treating scalp diseases occurred by dandruff-causing Malassezia species.

Cloning and Functional Characterization of the Germacradienol Synthase (spterp13) from Streptomyces peucetius ATCC 27952

  • Ghimire, Gopal Prasad;Oh, Tae-Jin;Lee, Hei-Chan;Kim, Byung-Gee;Sohng, Jae-Kyung
    • Journal of Microbiology and Biotechnology
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    • v.18 no.7
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    • pp.1216-1220
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    • 2008
  • Sequence analysis of the metabolically rich genome of Streptomyces peucetius ATCC 27952 revealed a 2,199 bp sesquiterpene alcohol (germacradienol) synthase-encoding gene from the germacradienol synthase/terpene cyclase gene cluster. The gene was named spterp13, and its putative function is as a germacradienol synthase/terpene cyclase. The amino acid sequence of Spterp13 shows 66% identity with SAV2163 (GeoA) from S. avermitilis MA4680 and 65% identity with SCO6073 from S. coelicolor A3(2), which produces germacradienol/geosmin. The full-length recombinant protein was heterologously expressed as a his-tagged fusion protein in Escherichia coli, purified, and shown to catalyze the $Mg^{2+}$-dependent conversion of farnesyl diphosphate to the germacradienol, which was verified by gas chromatography/mass spectrometry.

Anti-inflammatory Activity of Standardized Fraction from Inula helenium L. via Suppression of NF-κB Pathway in RAW 264.7 Cells

  • Chun, Jaemoo;Song, Kwangho;Kim, Yeong Shik
    • Natural Product Sciences
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    • v.25 no.1
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    • pp.16-22
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    • 2019
  • Inula helenium L. is rich source of eudesmane-type sesquiterpene lactones, mainly alantolactone and isoalantolactone, which have the various pharmacological functions. In this study, we examined the inhibitory effects of nitric oxide (NO) production of hexane, methylene chloride, ethyl acetate, butanol, and water fractions from I. helenium and investigated the anti-inflammatory effect of hexane fraction of I. helenium (HFIH) in LPS-induced RAW 264.7 cells. Quantification of alantolactone and isoalantolactone from HFIH was carried out for the standardization by multiple reaction monitoring using triple quadrupole mass spectrometer. HFIH significantly inhibited inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2) protein as well as their downstream products NO and prostaglandin $E_2$ ($PGE_2$) in LPS-stimulated RAW 264.7 cells. Moreover, HFIH suppressed $NF-{\kappa}B$ transcriptional activity by decreasing the translocation of p65 to the nucleus. The in vivo study further confirmed that HFIH attenuated the paw edema induced by carrageenan in an acute inflammation model. These findings suggest that HFIH may be useful as a promising phytomedicine for inflammatory-associated diseases.

A Sesquiterpene, Dehydrocostus Lactone, Inhibits the Expression of inducible Nitric Oxide Synthase and TNF$\alpha$ in LPS- Activated Macrophages

  • Lee, H.J.;Kim, N.Y.;D.H. Sohn;Lee, S.H.;J.H. Ryu
    • Proceedings of the Korean Society of Applied Pharmacology
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    • 1998.11a
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    • pp.176-176
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    • 1998
  • An enhanced formation of nitric oxide (NO) is an important mediator of hypotention, peripheral vasodilation and vascular hyporeactivity to vasoconstrictor agents in endotoxaemia. And tumor necrosis factor (TNF${\alpha}$), as a primary mediator of circulatory shock has been known to induce inducible nitric oxide synthase (i-NOS), leading to excessive production of NO. We isolated two sesquiterpene lactone compounds from Saussurea lappa and their structures were elucidated as dehydrocostus lactone and costunolide. These compounds inhibit the production of both NO and TNF${\alpha}$ by LPS (1 $\mu\textrm{g}$/$m\ell$)-activated Raw 264.7 cells. NO was measured spectropho-tometrically as nitrite by the Griess reagent and TNF${\alpha}$ by ELISA. Dehydrocostus lactone (IC$\sub$50/ : 3.0 ${\mu}$M) and costunolide (IC$\sub$50/ : 4.5 ${\mu}$M) inhibited the production of NO in LPS-activated Raw 264.7 cells by suppressing inducible nitric oxide synthase enzyme expression. These compounds also decreased the TNF${\alpha}$ levels in LPS-activated system in vitro and in vivo.

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Changes in Volatile Constituents of Zingiber officinale Roscoe Rhizomes During Storage (생강 저장 중의 향기성분 변화)

  • Kim, Myung-Kon;Lee, Byung-Eun;Yun, Se-Eok;Kim, Young-Hoi;Kim, Young-Kyu;Hong, Jai-Sik
    • Applied Biological Chemistry
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    • v.37 no.1
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    • pp.1-8
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    • 1994
  • This study was carried out to investigate the changes in volatile constituents concerning with the flavor of the green ginger (Zingiber officinale Roscoe) during storage in underground pit ($15^{\circ}C$, RH 95%). And the constituents of essential oil of etiolated shoots formed on the mother rhizomes during the five months storage in the dark under same conditions were compared with those of mother rhizomes. The essential oils of Korean domestic ginger (Bong-dong cultivar) were isolated by simultaneous steam distillation and extraction method (SDE). Then the compositions of the essential oils were analysed by GC and GC-MS spectrometry. The major compounds of essential oil from the fresh rhizomes were zingiberene, $citronellol+{\beta}-sesquiphellandrene$, ${\beta}-phellandrene$, camphene, geranial, ${\gamma}-bisabolene$, ar-curcumene+geranyl acetate, ${\alpha}-pinene$, ${\beta}-gurjunene$, limonene and neral. The content of monoterpene hydrocarbons increased with a concomitant lowering in the amounts of sesquiterpene hrdrocarbons and oxygenated sesquiterpenes during storage of rhizomes although contents of the oxygenated monoterpens changed little or slightly during the storage. During the storage the content of such monoterpenes as camphene, ${\beta}-phellandrene$ and citral (neral and geranial) increased whereas the content of such sesquiterpenes as zingiberene and $citronellol+{\beta}-sesquiphellandrene$ decreased. The composition of shoot oil differed from that of mother rhizome oil in having higher content of terpene hydrocarbons and also in the higher content of bornyl acetate, ${\beta}-gurjunene$ and ar-curcumene+geranyl acetate and lower in citral (neral and geranial).

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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.

Volatile Aroma Compounds and Their Characteristics of Labiatae by Solid-Phase Microextraction (SPME) (Solid-Phase Microextraction (SPME)에 의한 꿀풀과 약초의 향기성분과 그 특성)

  • Song, Yong-Eun;Ku, Chang-Sub;Mun, Sung-Phil;Ryu, Ji-Sung;Kim, Dae-Hyang;Choi, Joung-Sik;Choi, Yeong-Geun
    • Korean Journal of Medicinal Crop Science
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    • v.10 no.2
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    • pp.120-125
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    • 2002
  • This study was carried out to find the possibility of use of Solid Phase Microextraction (SPME) for extracting the volatile aroma compounds in the five aromatic plants (Agastache rugosa O. Kuntze, Mentha arvensis Linne, Thymus quinquecostatus Celakovsky, Elsholtzia splendens Nakai, Schizonepta tenuifolia Briquet) belongs to the Labiatae. In the result of the analysis, the volatile aroma compounds were mainly composed monoterpene alcohol (linanol, menthol, ${\alpha}-terpineol$, borneol), monoterpene ketone (limonene, menthone) and sesquiterpene (trans-caryophyllene,${\delta}-cadinene)$. The volatile aroma compounds of Agastache rugosa O. Kuntze and Mentha arvensis Linne were extracted by SPME more identified than the SDE. However, Schizonepta tenuifolia Briquet more identified by the SDE and in Elsholtzia splendens Nakai similar to the SDE. Especially, the SPME showed the sesquiterpene contents was more than the SDE. The major volatile aroma compounds were difference but the composition of those between the SPME and the SDE showed no difference. Within the results, the SPME showed the most convenient and a rapid extraction method to analysis of the volatile aroma compounds.