• Toxicological Research
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• v.4 no.2
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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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• v.7 no.3
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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.

• Korean Journal of Food Science and Technology
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• v.37 no.3
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• pp.360-363
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• 2005

To detect falcarinol in Acanthopanax senticosus, its stem and bark were extracted with methanol fractionated with petroleum ether and diethyl ether, and separated by silica gel column chromatography, Resulting six crude samples were compared with standard falcarinol through TLC on silica gel plates. Fraction 6 showed $R_{f}$ value of 0.46 similar to that of standard falcarinol. Through analytical reverse phase HPLC/PDA, UV spectra of standard falcarinol and traction 6 recorded between 200 and 340 nm showed identical peaks and UV spectra patterns. GC/MS revealed standard falcarinol and fraction 6 have equal retention times of 7.4 and 8.5 min before and after TMS-derivatization, respectively. Standard falcarinol and fraction 6 showed more similar spectrum patterns after TMS-derivatization than before. These results confirm presence of falcarinol in A. senticosus.

• Korean Journal of Agricultural Science
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• v.35 no.1
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• pp.11-17
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• 2008

This study was conducted to isolate polyacetylenes from the Acanthopanax senticosus and to identify the chemical structure of the polyacetylenes by UV, IR, $^1H$-NMR and $^{13}C$-NMR. One of the liposoluble materials was extracted with petroleum ether. Polyacetylene compounds were collected through solvent fractionation at silica gel column chromatograph. The HPLC was used for the semi-preparative separation IR spectra of fraction 5 showed triple bonds at $2256cm^{-1}$ and double bond at $1654cm^{-1}$, respectively, $^1H$-NMR spectra of Fraction 5 showed the double bond at 5.35-5.48 ppm. Triple bond at 64.0. 71.2, 74.2, 80.2 ppm and double bond at 121.89, 133.0 ppm were observed in the $^{13}C$-NMR spectra.

• IMMUNE NETWORK
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• v.12 no.5
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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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• v.15 no.1
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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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• v.19 no.1
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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.

• The Korea Journal of Herbology
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• v.31 no.5
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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.

• Journal of Pharmacopuncture
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• v.20 no.4
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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.

• Proceedings of the Ginseng society Conference
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• 1988.08a
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• pp.122-128
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• 1988

Several major polyacetylene compounds were isolated from the petroleum-ether fraction of fresh Korean ginseng roots through solvent fractionation. partition and silica gel column chromatography. Further separation of acetylenic compounds was accomplished by bonded normal phase HPLC utilizing a moderately nonpolar microparticulate column. The preparative separation for the various spectral measurements was carried out by low pressure preparative liquid chromatography. The chemical structure of these polyacetylenes separated was determined by UV. IR/FTIR. $^{1}H$ NMR. mass spectral and elemental analysis. These are identified to be heptadeca-1-en-4.6-diyn-3.9.l0.-triol [1] heptadeca-1.9-dien-4.6-diyn-3-ol. heptadeca-1.8-dien-4.6-diyn-3.10-diol and the 4th was denatured polyacetylene. heptadeca-1.4-dien-6.8-diyn-3.10-diol. Two different p-substituted benzoates of panaxynol were synthesized for the determination of exciton chirality. The circular dichroism spectra in the UV region show that panaxynol p-bromobenzoate and p-dimethyl-aminobenzoate constitute negative exciton chirality [2]. Isolated major polyacetylene compounds were irradiated in aerated solution with 300 nm UV light to obtain the oxidized product at the allylic alcohol center to corresponding carbonyl compounds such as heptadeca-1-en-4.6-diyn-9.10-diol-3-one and heptadeca-1.9-dien-4.6-diyn-3-one. These photooxidation compounds have en-on-diyne chromophore and undergo nucleophilic addition reaction with methanol to yield ${\beta}-methoxy$ carbonyl compounds such as heptadeca-9-en-4.6-diyn-1-methoxy-3-one and heptadeca-4.6-diyn-1-methoxy-9.10-diol-3-one.