• 약학회지
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• 제23권2호
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• pp.105-110
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• 1979

A simple total synthesis of the sesquiterpene, .alpha.-trans-atlantone which belongs to bisabolane family, is described. The kinetic enolate of mesityl oxide is used as nucleophilic synthon for an intermediate ($\alpha$-bisabololone) synthesis.

• 한국생명과학회:학술대회논문집
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• 한국생명과학회 2001년도 제31회 학술심포지움 및 춘계학술대회
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• pp.69-69
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• 2001

• 생약학회지
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• 제30권1호
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• pp.74-78
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• 1999

Nine sesquiterpene lactones, which were isolated from Hemisteptia lyrata Bunge, Chrysanthemum zawadskii Herbich var. latilobum Kitamura and Chrysanthemum boreale Makino were evaluated for the inhibition upon the nitric oxide release from the Raw cell and for the ACAT (acyl Co A: cholesterol acyltransferase) inhibitory assay. In the nitric oxide release inhibitory experiment, hemistepsin B $(IC_{50}\;=\;0.05\;{\mu}g/ml,\;0.15\;{\mu}M),$ cumambrin B, tulipinolide and costunolide exhibited strong inhibition with $IC_{50}$ values $0.05\;{\mu}g/ml\;(0.15\;{\mu}M),\;0.1\;{\mu}g/ml\;(0.38\;{\mu}M),\;0.2\;{\mu}g/ml\;(0.69\;{\mu}M)$ and $0.2\;{\mu}g/ml(0.86\;{\mu}M),$ respectively. In the ACAT inhibitory assay, angeloylcumambrin B, tigloylcumambrin B, tulipinolide and costunolide exhibited strong inhibition with $IC_{50}$ values $33\;{\mu}g/ml\;(95.4\;{\mu}M),\;22\;{\mu}g/ml\;(63.6\;{\mu}M),\;38\;{\mu}g/ml\;(151\;{\mu}M)$ and $17\;{\mu}g/ml(73.3\;{\mu}M),$ respectively, whereas other compounds did not exhibit significant activity against ACAT above $100\; {\mu}g/ml.$.

• 한국식품영양학회지
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• 제30권1호
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• pp.156-165
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• 2017

This study investigated the chemical composition of Petasites japonicus (S. et Z.) Maxim essential oil. During the period 2011~2013, P. japonicus (S. et Z.) Maxim plant was investigated for composition of the essential oil. Chemical composition and characteristic compounds of the essential oils from the aerial parts of the plant according to the crop year studied. The essential oils consisted of sesquiterpene compounds, which were the most abundant components. Samples collected in 2011 were found to be richer in oxygenated sesquiterpenes, while samples collected in 2012 and 2013 were richer in diterpene alcohols and sesquiterpene hydrocarbons, respectively. Ninety-two compounds were identified in the P. japonicus (S. et Z.) Maxim essential oil of 2011, and caryophyllene oxide (20.49%), ${\beta}$-caryophyllene (10.28%), ${\beta}$-bisabolene (6.80%), and alloaromadendrene (6.50%) were the major compounds. Seventy-four compounds were identified in the plant essential oil of 2012, and phytol (17.22%), ${\alpha}$-farnesene (15.31%), ${\alpha}$-caryophyllene (9.93%), and ${\beta}$-caryophyllene (6.12%) were the major compounds. Ninety-two compounds were identified in the plant essential oil of 2013, and ${\alpha}$-farnesene (22.42%), ${\alpha}$-caryophyllene (21.49%), pentadecane (15.35%), and germacrene (5.70%) were the major compounds. The content of most of the chemical constituents varied significantly with different harvesting time. The content of ${\alpha}$-caryophyllene and caryophyllene oxide was increased significantly from 2011 to 2013. The content of ${\alpha}$-caryophyllene and isocaryophyllene was decreased significantly from 2011 to 2013.

• 생명과학회지
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• 제14권4호
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• pp.657-663
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• 2004

고추에서 클로닝된 sesquiterpene cyclase (CASC) promoter에 cinnamic acid 4-hydroxylase (C4H)유전자를 클로닝하여 담배에 형질전환하였다. 형질전환체의 분석은 PCR, Southern blot분석으로 하였으며, CASC promoter의 작동여부를 조사하기 위하여 GUS histochemical assay를 하였다. 스트레스에 반응한다고 알려진 CASC promoter를 C4H gene과 fusion하여 C4H activity를 조사하여 스트레스에 반응하는 정도를 조사하였다. 최종적인 형질전환체로 확인된 개체는 평균 16.4% 정도였으며, 각 promoter별로 약간의 편차를 보였다. C4H activity 조사시 스트레스를 주지 않았을 때 대조구가 비슷한 양상을 나타내었다. 스트레스를 주었을 때 대조구와 비교하여 promoter 3번은 1.3배 activity가 높아졌으며 4번은 1.4배, 6은 2배, cyc 600은 1.1배 높아졌다. 이런 결과로 보아 이 promoter들은 UV에 반응하는 promoter이며 앞으로 stress에 저항하는 유전자의 적당한 promoter로, 타작물에 적용하여 stress저항성 작물의 육성 시 매우 유용하게 사용될 것으로 사료된다.

• Journal of Ginseng Research
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• 제34권1호
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• pp.17-22
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• 2010

Sesquiterpenes are found naturally in plants and insects as defensive agents or pheromones. They are produced in the cytosolic acetate/mevalonate pathway for isoprenoid biosynthesis. The inducible sesquiterpene synthases (STS), which are responsible for the transformation of the precursor farnesyl diphosphate, appear to generate very few olefinic products that are converted to biologically active metabolites. In this study, we isolated the STS gene from Panax ginseng C.A. Meyer, designated PgSTS, and investigated the correlation between its expression and various abiotic stresses using real-time PCR. PgSTS cDNA was observed to be 1,883 nucleotides long with an open reading frame of 1,707 bp, encoding a protein of 568 amino acids. The molecular mass of the mature protein was determined to be 65.5 kDa, with a predicted isoelectric point of 5.98. A GenBank BlastX search revealed the deduced amino acid sequence of PgSTS to be homologous to STS from other plants, with the highest similarity to an STS from Lycopersicon hirsutum (55% identity, 51% similarity). Real-time PCR analysis showed that different abiotic stresses triggered significant induction of PgSTS expression at different time points.

• Archives of Pharmacal Research
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• 제29권11호
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• pp.937-941
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• 2006

Ixeris dentata forma albiflora was extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH and $H_{2}O$. Eight sesquiterpenes were isolated through repeated silica gel and octadecyl silica gel ($C_{18},\;ODS$) column chromatography of the EtOAc and n-BuOH fractions. Physicochemical analysis using NMR, MS and IR revealed the chemical structures of the sesquiterpenes, which were zaluzanin (1), 9a-hydroxyguaian-4(15), 10(14), 11 (13)-triene-6, 12-olide(2), $3{\beta}-O-{\beta}-D-glucopyranosyl-8{\beta}-hydroxyguaian$-4(15), 10(14)-diene-6, 12-olide (3), $3-O-{\beta}-D-glucopyranosyl-8{\beta}-hydroxyguauan$-10(14)-ene-6, 12-olide (4), ixerin M (5), glucozaluzanin C (6), crepiside I (7), and ixerin D (8). This is the first time that these sesquiterpene lactones have been isolated from this plant. Compounds 1, 2 and 7 revealed relatively high cytotoxicities on human colon carcinoma cell and lung adeno-carcinoma cell, while compounds 5 and 7 showed acyl-CoA: cholesterol acyltransferase (ACAT) inhibitory activity.

• Journal of Applied Biological Chemistry
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• 제49권1호
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• pp.16-20
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• 2006

The flowers of Hemisteptia lyrata B. afforded two known acylglycerylgalactosides, 2',3'-di-O-(9Z,12Z,15Z-octadecatrienoyl)glyceryl ${\beta}$-D-galactopyranoside (1) and 2'-O-(9Z,12Z,15Z-octadecatrienoyl)glyceryl ${\beta}$-D-galactopyranoside (2), and a new sesquiterpene galactopyranoside, 7-eudesmene-1${\beta}$,4${\beta}$-diol-1-O-${\beta}$-D-galactopyranoside (3). This is the first time that galactopyranosides (1-3) have been isolated from the genus Hemisteptia. Their structures and stereochemistry were elucidated by 1D and 2D NMR data, including COSY, NOESY and HMBC experiments.

• 생명과학회지
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• 제31권4호
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• pp.430-441
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• 2021

세스퀴테르펜 락톤(Sesquiterpene lactones; STL) 화합물은 테르페노이드의 일종으로 주로 국화과에서 발견이 되고 강한 세포 독성을 나타내는 생리학적 특성을 지니고 있다. 이러한 세스퀴테르펜 락톤은 강한 세포 독성으로 인해 연구가 미미하였으나, 최근 화학적 변형을 통해 독성이 적은 형태로 합성하여 새로운 의약품 개발로서의 연구가 활발히 진행되고 있다. 세스퀴테르펜 락톤 화합물인 artemisinin 및 mipsagargin 화합물은 현재 말라리아 및 종양성장에 대한 약물로 사용되고 있다. 또한 항산화, 간보호, 항바이러스, 항균, 항종양 및 항노화 등의 생리활성 효능이 보고되어 있으며, 종양세포에서 자멸사를 유도하여 항암제로서의 연구가 진행되고 있다. 본 연구에서는 세스퀴테르펜 락톤 화합물인 artemisinin, costunolide, thapsigargin, arglabin, parthenolide, alantolactone, cynaropicrin, helenalin, 및 santonin의 생리활성 효능에 대한 연구 동향을 검토하고자 한다.

• Bulletin of the Korean Chemical Society
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• 제34권7호
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• pp.2215-2217
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• 2013