산국에서의 Terpenes 함량의 변이

김종희 한국생태학회 1997 Journal of Ecology and Environment Vol.20 No.6

The monoterpenes and sesquiterpenes are analysed in the leaf and stem of Chrysanthemum boreale using gas chromaltography-mass spectrometry (GC-MS). The total amount of sesquiterpenes are always higher than monoterpenes in both leaf (2.0-3.4 times) and stem (1.6-8.3 times). The mono- and sesquiterpenes yields of the leaf are higher than the stem. There was no significant difference among the leaf developmental stages, while those of stem were varied. Seventeen monoterpenes and 9 sesquiterpenes compound in this plants comprised more than 5% of the mean total monoterpenes and the total sesquiterpenes in each dates. Among leaf monoterpenes, the concentration of (+)-Limonene and unknown compound no. 13 (Retention time, R.T.=17.28) varied significantly during leaf growing season, and the concentrafion of unknown compound no. 7 (R.T.=35.04) and no. 9(R.T.=35.71) varied in the leaf sesquiterpenes. Similarly the results from the leaf, the concentration of five monoterpenes in stem also varied significantly during maturing period, and much varied in seven compounds of stem sesquiterpene. The major sesquiterpenes of leaf and stem were ${\alpha}-Humulene$ and compound no. 2(R.T.=26.19).

약용식물유래 sesquiterpene계 화합물의 담수조류 생육억제활성 특성

황현진(Hyun Jin Hwang),서보람(Bo-Ram Seo),김재덕(Jae Deog Kim),장현우(Hyun Woo Jang),최정섭(Jung Sup Choi),김진석(Jin-Seog Kim) 韓國雜草學會 2009 Weed&Turfgrass Science Vol.29 No.4

본 연구에서는 창출, 호초 및 강황으로부터 분리된 sesquiterpene계 화합물의 조류종별 살조특성(algicidal spectrum)을 알아보기 위해서는 녹조류 5종(Botryococcus braunii UTEX 572, Botryococcus braunii UTEX 2441, Chlamydomonas spp., Chlorella vulgaris UTEX 265, Scenedesmus spp.)과 남조류 4종(Anabaena affinis Lem, Microcystis aeruginosa UTEX 2388, Oscillatoria tenuis UTEX1566, Spirulina platensis)을 대상으로 살조활성 정도를 조사하였다. 약용식물 헥산추출물들의 M. aeruginosa에 대한 90% 이상 방제활성은 2.5~10㎍ mL-1 수준이었으나, C. vulgaris에 대해서는 50㎍ mL-1 수준에서 나타나 M. aeruginosa를 상대적으로 잘 방제하였다. 추출물로부터 분리 furanodiene과 β-bisabolene도 같은 경향을 보였다. 호초로부터 분리한 trans-caryophyllene은 유해남조류 3종(A. affinis., M. aeruginosa., O. tenuis)에 대해서는 민감한 반을을 보이고, S. platensis와 녹조류에 대해서는 상대적으로 둔감한 반응을 보여 뚜렷한 선택성을 가졌지만, caryophyllene oxide는 남조류와 녹조류간에 뚜렷한 선택성 없이 모두 비슷한 억제활성을 가지되 유해 남조류 3종 방제에 있어서는 trans- caryophyllene보다 고농도 처리가 요구되었다. 한편, a-curcumene은 2.5-5.0㎍ mL-1 처리 범위에서 녹조류 및 S. platensis 생장에 심각한 저해를 주지 않으면서 유해 남조류 3종을 잘 방제할 수 있었다. 이들의 결과는 화합물에 대한 조류 종의 생육억제반응은 종(種)에 따라 다르며, 천연물을 활용하여 생태계에서 유해 남조류를 선택적으로 방제하거나, 특정 유용조류 재배시 다른 조류종으로부터의 오염을 방지하는 것이 가능함을 보여준다. The inhibition of algae growth to n-hexane fractions of methanol extracts of Atractylodes chinensis, Piper nigrum, and Curcuma aromatica and sesquiterpenes compounds isolated from medicinal plants, were investigated with 5 species of green algae (Botryococcus braunii UTEX 572, B. braunii UTEX 2441, Chlamydomonas spp., Chlorella vulgaris UTEX 265, Scenedesmus spp.) and 4 species of blue-green algae (Anagaena affinis Lem, Microcystis aeruginosa UTEX 2388, Oscillatoria tenuis UTEX1566, Spirulina platensis) in the laboratory. n-Hexane fractions of methanol extracts inhibited more than 90% the M. aeruginosa in a range of 2.5 to 10 ㎍ mL-1 and the C. vulgaris in a range of 50 ㎍ mL-1. The isolated componds, furanodiene and β-bisabolene also showed a same tendency with more higher control to M. aeurginosa. The trans-caryophyllene isolated from P. nigrum showed higher activity in the control of three harmful algae A. affinis, M. aeruginosa, and O. tenuis. However, S. platensis and 5 species of green algae were fairly tolerant to trans-caryophyllene. Caryphyllene oxide showed a similar algicidal activity without a significant selectivity between green algae and bule-green algae and had an activity at higher application rate than one of trans-caryophyllene. On the other hand, a-curcumene isolated from C. aromatica was able to control three harmful algae A. affinis, M. aeruginosa, and O. tenuis without interrupting the growth of S. platensis and 5 species of green algae in a range of 2.5 to 10 ㎍ mL-1. These results show that the responses of algae growth inhibition to compounds is likely different in every species, and sesquiterpene compinds prepared from this study seemed to have a potential as natural algicide for the control of harmful algae and to solve partly a contamination problem in industrial cultivation of a certain algae.

A New Sesquiterpene and Other Terpenoid Constituents of Chisocheton penduliflorus

Phongmaykin, Jarinporn,Kumamoto, Takuya,Ishikawa, Tsutomu,Suttisri, Rutt,Saifah, Ekarin 대한약학회 2008 Archives of Pharmacal Research Vol.31 No.1

A new aromadendrane sesquiterpene, allo-aromadendrane-10${\alpha}$, 14-diol (3), was isolated from Chisocheton penduliflorus (Meliaceae), along with two known sesquiterpenes: allo-aromadendrane-10${\beta}$, 13, 14-triol (7). Six dammarane triterpenoids, including cabraleadiol (1), eichlerialactone (4), cabraleahydroxylactone (5), cabralealactone (6), hollongdione (8) and dammaradienone (9), the coumarins scoparone and scopoletin, and vanillic acid were also isolated from the wood and leaves of this plant. Compounds 1-7 displayed antimycobacterial activity against Mycobacterium tuberculosis. Compounds 1, 4, 5 and 6 were weakly cytotoxic to a breast cancer (BC) cell line; whereas, compound 6 was moderately active against a small-cell lung cancer (NCI-H187) cell line.

A New Sesquiterpene and Other Terpenoid Constituents ofChisocheton penduliflorus

Jarinporn Phongmaykin,Takuya Kumamoto,Rutt Suttisri,Tsutomu Ishikawa,Ekarin Saifah 대한약학회 2008 Archives of Pharmacal Research Vol.31 No.1

A new aromadendrane sesquiterpene, allo-aromadendrane-10α, 14-diol (3), was isolated from Chisocheton penduliflorus (Meliaceae), along with two known sesquiterpenes: allo-aromadendrane- 10 β, 14-diol (2) and allo-aromadendrane-10 β, 13, 14-triol (7). Six dammarane triterpenoids, including cabraleadiol (1), eichlerialactone (4), cabraleahydroxylactone (5), cabralealactone (6), hollongdione (8) and dammaradienone (9), the coumarins scoparone and scopoletin, and vanillic acid were also isolated from the wood and leaves of this plant. Compounds 1-7 displayed antimycobacterial activity against Mycobacterium tuberculosis. Compounds 1, 4, 5 and 6 were weakly cytotoxic to a breast cancer (BC) cell line; whereas, compound 6 was moderately active against a small-cell lung cancer (NCI-H187) cell line.

약용식물로부터 살조(殺藻)활성을 갖는 sesquiterpene계 화합물의 분리 및 동정

최정섭(Jung Sup Choi),황현진(Hyun Jin Hwang),서보람(Bo-Ram Seo),김재덕(Jae Deog Kim),장현우(Hyun Woo Jang),김진석(Jin-Seog Kim) 韓國雜草學會 2009 Weed&Turfgrass Science Vol.29 No.2

본 연구에서는 천열 살조제(natural algicide)를 탐색하는 과정 중에서 창출 뿌리, 호초 열매, 강황 뿌리의 메탄올추출물이 M. aeruginosa에 대해 우수한 살조활성을(10-25㎍ mL-1 처리농도에서 90% 이상 생육억제) 보였다. 세 식물 공히 메탄올 추출물을 n-hexane층, EtOAc 층, BuOH 층, 물 층으로 분획하였을 때, n-hexane 층에서 가장 높은 살조활성을 나타냈다(2.5-10㎍ mL-1 처리농도에서 90% 이상 생육억제). n-Hexane 분획물을 가지고 생물활성 조사를 하면서 silica gel column chromatography, Sephades LH-20 column chromatography, preparative TLC 등을 통해 유효성분을 분리하였다. TLC 등을 통해 단일성분으로 확인된 것을 GC-MS 분석과 MS spectrum data base 일치를 통해 분리물질을 동정한 결과, 창출로부터 furanodiene, 호초로부터 trans-caryophyllene과 caryophyllene oxide, 강황으로부터 alpha-curcumene과 beta-bisabolene 등 sesquiterpene류 화합물들임을 밝혔다. 분리된 sesquiterpene류 화합물들의 M. aeruginosa에 대한 생육억제활성을 조사한 결과, caryophyllene oxide를 제외한 나머지 화합물은 1.3㎍ mL-1 처리 농도에서 90% 이상의 방제활성을 가졌다. 한편, 분리물질과 헥산분획층간에는 2배 내외의 활성 차이만 나타나므로 상황에 따라 추출물 분획을 천연살조제로서 이용할 수 있을 것이며 이의 활용방안에 대해서는 추가연구가 필요하다. During the search for natural algicidal compound, we found that the methanol extract of dried rhizome of Atractylodes chinensis, dried seed of Piper nigrum, and dried root of Curcuma aromatica strongly inhibited the growth of Microcystis aeruginosa. When algicidal activity of n-hexane, EtOAc, BuOH and aqueous fractions obtained by solvent partitioning of the methanol extracts was investigated, n-hexane fractions showed the highest activity in the control of Microcystis aeruginosa, and inhibited more than 90% the growth of M. aeruginosa in a range of 2.5 to 10 ㎍ mL-1. According to bioassay guide, algicidal compounds were isolated from the hexane fraction through silica gel column chromatography, Sephadex LH-20 column chromatography and preparative TLC. The isolated substances were analysed by GC-MS and identified by a comparison of mass spectra with literature data (WILEY8 library). As a results, furanodiene was isolated from Atractylodes chinensis, trans-caryophyllene and caryophyllene oxide from Piper nigrum, and alpha-curcumene and beta-bisabolene from Curcuma aromatica, which are known as a sesquiterpene compounds. The compounds except caryophyllene oxide inhibited more than 90% the growth of M. aeruginosa in a range of 1.3 to 5.0 ㎍ mL-1. After all, extracts and sesquiterpene compounds, prepared from this study were likely to have a potential as natural algicides for the control of harmful algae. For practical use, further research is required.

Olefin Metathesis를 이용한 황칠 Essential Oil의 경화 반응에 관한 연구

김미리 ( Mi Ri Kim ),이원휘 ( Won Hwi Lee ),유혜진 ( Hye Jin Yoo ),김종상 ( Jong Sang Kim ),정인우 ( In Woo Cheong ) 한국접착및계면학회 2015 접착 및 계면 Vol.16 No.4

황칠원액을 에탄올로 추출한 황칠의 essential oil을 올레핀 메타테시스(olefin metathesis) 반응의 하나인 ROMP(ring opening metathesis polymerization)법을 이용하여 경화 반응을 수행하였으며, 자연 경화 및 UV 광경화법의 경화 특성 및 경화된 필름의 물성에 대해서 비교 연구하였다. 경화 전후의 황칠의 조성 변화에 대해서 가스 크로마토그래피 질량분석법(GC-MS, gas chromatography mass spectrometry)을 통해 연구하였으며, ROMP법에 의해 경화된 필름의 겔 함량(gel contents, 40%)은 자연 경화(8%)나 UV 광경화법(25%)에 비해 높은 값을 보여주었다. 100°C의 온도 및 2 wt%의 Grubbs’catalyst 조건에서 ROMP 경화반응은 2 h 이내의 경화 반응이 완료되어 자연 경화에 비해 비교적 빠른 경화 속도를 보여주었으며, UV 광경화법에 비해 주름이 없으며 외관상 균일한 도막이 형성됨을 확인하였다. 또한 기존에 경화반응에 참여하는 것으로 알려져 있는 폴리아세틸렌계 성분 이외에 sesquiterpene류인 α-selinene, β-selinene, δ-cadinene 등도 ROMP 경화 반응에 참여함을 확인하였다. Raw sap of essential oil in Korean Dendropanax lacquer was extracted with ethanol, and which was cured by using ROMP (ring opening metathesis polymerization, one of olefin metathesis). Curing behavior with subsequent film properties were studied and compared with conventional curing (under ambient conditions) and UV photo curing. The compositional changes of major ingredients in the lacquer before and after curing were studied by using GC-MS (gas chromatography mass spectrometry). ROMP-cured coating film showed higher gel contents (40%) as compared to those of conventional (8%) and UV curing (25%). ROMP curing with 2 wt% Grubbs’ catalyst at 100°C completed curing reaction within 2 h, which was much faster than that of conventional curing. The quality of coating film prepared with ROMP was more homogeneous and wrinkle-free as compared with that with UV curing. It was found that major ingredients of sesquiterpenes, such as α-selinene, β-selinene, and δ-cadinene were reacted in ROMP, as well as polyacetylenes.

Dimeric- and trimeric sesquiterpenes from the flower of <i>Inula japonica</i>

Jin, Qinghao,Lee, Jin Woo,Jang, Hari,Lee, Hye Lim,Kim, Jun Gu,Wu, Wanying,Lee, Dongho,Kim, Eun-Hee,Kim, Youngsoo,Hong, Jin Tae,Lee, Mi Kyeong,Hwang, Bang Yeon Elsevier 2018 Phytochemistry Vol.155 No.-

<P><B>Abstract</B></P> <P>An undescribed unusual sesquiterpene trimer and three sesquiterpene dimers were isolated from the flowers of <I>Inula japonica</I>. Their structures were elucidated by extensive analysis of 1D and 2D NMR spectroscopic data as well as HRESIMS data. Inulajaponicolide A has an undescribed carbon skeleton comprising of one xanthanolide and two guaianolide units with the linkage mode of C-11/C-3ʹ and C-11ʹ/C-1ʹʹ via a Diels-Alder cycloaddition reaction. Inulajaponicolides C and D exhibited moderate cytotoxic activity against A 549 and NCI-H460 human cancer cell lines with IC<SUB>50</SUB> values ranging from 8.5 to 17.8 μM. Inulajaponicolides A-D and lineariifolianoid A possessed significant inhibitory potency against nitric oxide production in LPS-induced RAW264.7 cells with IC<SUB>50</SUB> values ranging from 1.0 to 4.1 μM.</P> <P><B>Highlights</B></P> <P> <UL> <LI> Four sesquiterpenes were isolated from <I>Inula japonica.</I> </LI> <LI> Inulajaponicolide A is an unprecedented sesquiterpene trimer formed by both endo- and exo-type 1,3-linked Diels-Alder cycloaddition. </LI> <LI> Inulajaponicolides B-D are biogenetically related sesquiterpene dimers. </LI> <LI> Some of the isolates were showed cytotoxic and NO inhibitory activities. </LI> </UL> </P> <P><B>Graphical abstract</B></P> <P>An undescribed unusual sesquiterpene trimer and three sesquiterpene dimers were isolated from the flowers of <I>Inula japonica</I>. Some of the isolates were showed cytotoxic and NO inhibitory activities.</P> <P>[DISPLAY OMISSION]</P>

Sesquiterpene Derivatives Isolated from Cyperus rotundus L. Inhibit Inflammatory Signaling Mediated by NF-kB

Salman Khan,최란주,이동웅,김영식 한국생약학회 2011 Natural Product Sciences Vol.17 No.3

The immune system is finely balanced by the activities of pro-inflammatory and anti-inflammatory mediators or cytokines. Unregulated activities of these mediators can lead to the development of various inflammatory diseases. A variety of safe and effective anti-inflammatory agents are available with many more drugs under development. Of the natural compounds, the sesquiterpenes (nootkatone, a-cyperone, valencene and b-selinene) isolated from C. rotundus L. have received much attention because of their potential anti-inflammatory effects. However, limited studies have been reported regarding the influence of sesquiterpene structure on anti-inflammatory activity. In the present study, the anti-inflammatory potential of four structurally divergent sesquiterpenes was evaluated in lipopolysaccaride (LPS)-stimulated RAW 264.7 cells, murine macrophages. Among the four sesquiterpenes, a-cyperone and nootkatone, showed stronger anti-inflammatory and a potent NF-kB inhibitory effect on LPS-stimulated RAW 264.7 cells. Molecular analysis revealed that various inflammatory enzymes (iNOS and COX-2) were reduced significantly and this correlated with down-regulation of the NF-kB signaling pathway. Additionally, electrophoretic mobility shift assays (EMSA) elucidated that nootkatone and a-cyperone dramatically suppressed LPS-induced NF-kB-DNA binding activity using 32P-labeled NF-kB probe. Hence, our data suggest that a-cyperone and nootkatone are potential therapeutic agents for inflammatory diseases.

Accumulation of Sesquiterpenes and Polysaccharides in Cells of Zedoary (Curcuma zedoaria Roscoe) Cultured in a 10 L Bioreactor

Nguyen Hoang Loc,Vo Chau Tuan,Doan Huu Nhat Binh,Truong Thi Bich Phuong,김태금,양문식 한국생물공학회 2009 Biotechnology and Bioprocess Engineering Vol.14 No.5

We developed a cell suspension culture system for zedoary Curcuma zedoaria Roscoe), using 100 g fresh weight inoculum in a batch culture. The maximum cell biomass of 68.46 g/L fresh weight was obtained after 14 days of culture in a 10 L bioreactor with a pitch-blade impeller maintained at an agitation speed of 150 rpm and an aeration rate of 2.5 L/min. The accumulation of sesquiterpenes and polysaccharide in zedoary cells from 2 to 18 days was measured by HPLC and a phenol-sulfuric acid assay, respectively. The total polysaccharide concentration increased between 2 to 10 days of culture and reached a maximum value of 6.55%. HPLC revealed several eluted peaks of sesquiterpenes, which increased in amplitude from days 2 to 10. Furthermore, our results indicated that biotransformation occurred in the cell suspension, transforming certain sesquiterpenes into other types during culture

Atractylodes 屬 식물의 根莖에 함유된 휘발성 terpene 성분

김정훈 한약정보연구회 2018 한약정보연구회지 Vol.6 No.1

Volatile terpenes are characteristic chemical compounds contained in the rhizomes of genus Atractylodes plants and their chemical structure have been identified using gas chromatography-mass spectrometry (GC-MS). The present study aimed to classify volatile terpenes analyzed by GC-MS in Atractylodes rhizomes by their chemical structures. The articles published from 2007 to 2017 were searched using electronic databases. The reported volatile terpenes identified by GC-MS were classified by their chemical skeletons. Volatile terpenes were divided into C10-based monoterpenes and C15-based sesquiterpenes and they were subdivided into acyclic, monocyclic, polycyclic (bicyclic and tricyclic) terpenes. Particularly, monocyclic sesquiterpenes included Elemene-type, Olefinic, and Bisabolene-type; bicyclic sesquiterpenes included Eudesmane-type, Guaiane-type, Germacrene-type, Cadinene-type, Humulene-type, Caryophyllene-type, Himachalane-type, Eremophilane-type, Spirovetivane-type, Hydroazulene-type, Marasmane-type, Olefinic, and Valencane-type; and tricyclic sesquiterpenes included Longifolene-type, Aristolene-type, Patchoulane-type, Isocomene-type, Cedrene-type, Copaene-type, Longipinane-type, Neoclovene-type, and Panasinsane-type. The present study provides structural information of volatile terpenes from Atractylodes rhizomes, which would be fundamental data for further structural researches.