• Toxicological Research
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• 제4권2호
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• pp.95-105
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• 1988

The effects of polyacetylenes on living membrances, rat erythrocyte and murine leukemic L1210 cell as well as artificial lipid bilayer were determined to investigate the cytotoxic mechanism of polyacetylenes against cancer cell lines. As results, panaxydol and panaxynol caused erythrocyte hemolysis dose-dependently while panaxytriol had no lysis. For liposomes composed of phosphatidyl choline (PC) and phosphatidic acid(PA), all three polyacetylenes supressed the osmotic behavior at the same degree.

• Bulletin of the Korean Chemical Society
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• 제7권3호
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• pp.179-182
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• 1986

A major polyacetylene compound from Panax ginseng roots, heptadeca-1-en-4,6-diyn-3,9,10-triol, was irradiated with 300 nm UV light to obtain a photooxidized acetylenic compound having the conjugated en-on-diyne chromophore, heptadeca-1-en-4,6-diyn-9,10-diol-3-one. The same oxidation product was obtained exclusively by 4-(dimethylamino) pyridinium chlorochromate at room temperature.

• 한국식품과학회지
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• 제37권3호
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• pp.360-363
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• 2005

가시오가피에서 Polyacetylene 성분 중 falcarinol을 탐색하기 위해 TLC, HPLC/PDA, GC, GC/MS를 이용하여 falcarinol 표준품과 소분획물 사이의 비교 분석을 통하여 가시오가피에서 falcarinol을 동정하였다. 가시오가피 추출물을 silica gel column상에서 용매의 극성차이에 의해 6개의 분획물을 얻었고, 6개의 분획물과 falcarinol 표준품과의 TLC 상에서 전개시킨 결과 fraction 6 분획물에서 falcarinol과 동일 band의 물질을 분리하였다. Fraction 6의 분획물과 falcarinol 표준품을 HPLC/PDA로 분석한 결과 falcarinol 표준품의 peak와 동일 retention time의 peak를 fraction 6에서 분리하여 200-340nm 상에서 UV spectrum을 관찰한 결과 동일한 UV spectrum pattern을 보이는 것을 확인하였다. 이는 전형적인 polyacetylene 화합물의 UV spectrum pattern이었으며, 기존에 보고된 falcarinol의 UV spectrum과도 동일하였다. GC로 TMS 유도체화 전,후의 retention time을 확인한 결과 표준품과 fraction 6에서 동일한 결과를 보였다. TMS 유도체화 후에는 7.5분에서 8.5분으로 약 1분 정도 retention time이 증가하였고, detection 감도 또한 증가하였다. Falcarinol 표준품과 fiaction 6 분획물을 TMS 유도체화 후에 GC/MS로 mass fragment ion을 분석한 결과 표준품과 동일한 경향을 보였고 이는 기존의 보고와도 일치하였다(16). 본 실험결과들로 미루어 가시오가피에도 polyacetylene 성분인 falcarinol 존재하는 것으로 확인되었다.

• 농업과학연구
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• 제35권1호
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• pp.11-17
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• 2008

가시오가피를 실온에서 petroleum ether로 추출한 polyacetylene의 동정하기 위하여 TLC, HPLC, UV spectrum, IR, NMR로 수행하였다. TLC에 전개시킨 결과, polyacetylene 표준품과 동일한 band가 fraction 5에서 확인되었으며, HPLC에서 fraction 5를 분리시킨 결과 retention time이 4.40, 5.36, 6.40분이었다. 이를 UV spectrum에서 확인한 결과, 6.40분의 peak(compound 3)에서 polyacetylenes의 파장인 231.0nm, 239.0nm, 257.0nm을 나타내었다. IR spetrum에서 triple bond $2256cm^{-1}$과 double bond $1654cm^{-1}$의 전형적인 peak를 나타내었으며, $^{13}C$-NMR(400MHz, $CDCl_3$)에서 polyacetylenes 전형적인 64.0, 71.2, 74.2, 80.2ppm은 2개의 triple bond에 의한 peak와 121.89, 133.0ppm에서 internal double bond로 결합된 2개의 peak를 확인 할 수 있었다.

• IMMUNE NETWORK
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• 제12권5호
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• pp.213-216
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• 2012

Our previous report showed that polyacetylene compound, 1-Heptadecene-11, 13-diyne-8, 9, 10-triol (PA) from the root of Cirsium japonicum var. ussuriense has anti-inflammatory activity. In this study we investigated the role of the PA as inhibitor of caspase-1, which converts prointerleukin-$1{\beta}$ (proIL-$1{\beta}$) to active IL-$1{\beta}$ and is activated by inflammasome involved in the inflammatory process. We tested the effect of PA on the production of pro-inflammatory cytokines, IL-$1{\beta}$ in murine macrophage cell line, RAW264.7. PA inhibited lipopolysaccharide (LPS)-induced IL-$1{\beta}$ production by macrophages at a dose dependent manner. PA also suppressed the activation of caspase-1. The mRNA level of ASC (apoptosis-associated spec-like protein containing a CARD), an important adaptor protein of inflammasome, was decreased in the PA treated group. Therefore our results suggest that the anti-inflammatory effect of PA is due to inhibit the caspase-1 activation.

• Macromolecular Research
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• 제15권1호
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• pp.5-9
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• 2007

The attenuated total reflection infrared (ATR-IR) spectra of trans-polyacetylene (trans-PA) film doped with sodium (n-doping) were observed in the range of 1900 to $700cm^{-1}$. The observed IR bands were attributed to negatively charged domains created by n-doping electrons. The doping-induced IR bands showed considerable difference from its pristine film. After doping, the out-of-plane CH deformation band of the strong $1010cm^{-1}$ region in the pristine film disappeared while several new bands were observed at 1600 (due to C=C stretching), 1400 (due to in-plane CH bending), 1290 and 1174 (due to CH stretching), and $880cm^{-1}$ (due to CC stretching) regions for Na-doped PA. In particular, a weak band of C=C stretching at $1600cm^{-1}$ was newly obtained for the first time in the present study. The electro conductivity of the doped trans-PA film was $10^2S/cm$ and the origins of doping-induced IR bands are discussed in terms of solitons and polarons.

• Biomolecules & Therapeutics
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• 제19권1호
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• pp.97-101
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• 2011

Cirsium japonicum var. ussuriense is known to have a variety of biological activities, including anti-inflammatory, analgesic activity and antipyretic activity. In this study we investigated the role of polyacetylene compound, 1-Heptadecene-11, 13-diyne-8, 9, 10-triol (PA) from the root of Cirsium japonicum var. ussuriense as an immune-modulator. PA was evaluated as inhibitors of some macrophage functions involved in the inflammatory process. We tested the effect of PA on the production of pro-inflammatory cytokines, interleukin-1beta (IL-$1{\beta}$) and tumor necrosis factor-alpha (TNF-$\alpha$), and nitric oxide (NO) in murine macrophage cell line, RAW264.7. There was no effect on cytokine production of macrophages by PA itself. However, PA inhibited lipopolysaccharide (LPS)-induced IL-$1{\beta}$ and TNF-$\alpha$ production by macrophages at a dose dependent manner. PA also suppressed the NO production of macrophages by LPS. LPS-induced NF-${\kappa}B$ activity was decreased by treatment of PA. Therefore, these results suggest that PA has anti-inflammatory effect by inhibiting the NF-${\kappa}B$ activation.

• 대한본초학회지
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• 제31권5호
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• pp.25-39
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• 2016

Objectives : Atractylodes rhizomes, which have been widely used to treat gastrointestinal disorders, consist of numerous chemical compounds. Polyacetylenes are the parts of characteristic compounds of importance required to understand the therapeutic properties of Atractylodes rhizomes. It is necessary to understand the physicochemical and pharmacological properties of polyacetylenes in the Atractylodes rhizomes.Methods : The literatures from 1970 to January 2016 were searched using Korean and international electronic databases. The chemical structures of polyacetylenes were drawn by structure-drawing software.Results : The reported polyacetylenes were classified by their chemical skeletons and original resources, and their physicochemical and pharmacological features were discussed. Polyacetylenes with skeletal moieties were reported, such as diene-diyne types (two double and two triple carbon-bonds), triene-diyne types (three double carbon bonds and two triple carbon bonds), and monoene-diyne types (one double carbon bonds and two double carbon bonds), with various functional groups. Atractylodin was most frequently reported from many Atractylodes species. Atractylodin-related polyacetylenes showed chemical instability in both high and freezing temperatures. Processing of the Atractylodes rhizomes by stir-frying with bran could affect the contents of polyacetylenes and their bioavailability in vivo. Several polyacetylenes showed structure-related anti-inflammatory activities and gastrointestinal activities.Conclusion : Polyacetylene compounds in Atractylodes rhizomes were based on three chemical backbones and showed diverse physicochemical and pharmacological features. The present study provides structural, physicochemical, and pharmacological information of polyacetylene from Atractylodes rhizomes. This information provides fundamental data for further research.

• 대한약침학회지
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• 제20권4호
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• pp.274-279
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• 2017

Objective: SanYangSam and SanYangSanSam are traditional Korea-medical herbs that are grown from Panax ginseng C.A. Meyer. In our previous studies, we found that the functional compounds in SanYangSam and SanYangSanSam were different and depended on the type and the cultivation environment of ginseng. This study aimed to profile the functional constituents in SanYangSam and SanYangSanSam. Methods: To profile the functional aspects of the many compounds that have therapeutic activities in SanYangSam and SanYangSanSam extracts, we used liquid chromatography tandem mass spectrometry and quadrupole orthogonal acceleration time-of-flight mass spectrometry. Results: A total of four major compounds were detected; two of which were the natural flavonoids kaempferol and quercetin. Among others, two polyacetylene compounds, including panaxydol and panaxynol, were detected. Conclusion: In this study, we found that panaxydol, one of the polyacetylene constituents of ginseng, is a candidate anti-cancer agent in SanYangSam and SanYangSanSam pharmacopuncture. In addition, we found that the panaxydol levels in the SanYangSanSam extract were over 30 times those in the SanYangSam extract.

• 고려인삼학회:학술대회논문집
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• 고려인삼학회 1988년도 학술대회지
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• pp.122-128
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• 1988

폴리아세칠랜계 화합물이 함유된 인삼의 석유 에텔 추출물은 시험관내 실험에서 Sarcoma 180, Walker carcinosarcoma 256, $L_{1210}leukemic$ lympocyte의 성장을 억제한다. 우리는 석유 ether 추출물로 부터 몇가지 포리아세틸렌계 화합물을 분리하여 화학구조를 밝혔다. UV, IR $^{1}H$ NMR, $^{13}C$ NMR, EI mass, CI mas, 원소분석과 산화 또는 산촉매 가수분해와 같은 화학적인 방법으로 얻어진 자료에 근거하여 이들은 heptadeca-1,9-dien-4,6-diyn-3-ol, hepatadeca-l-en-4.6-diyn-9,10-epoxy-3-ol 및 hepatadeca-1,8-dien-4,6-diyn-3,10-diol로 밝혀 졌다.