• Proceedings of the Korean Society of Precision Engineering Conference
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• 2006.05a
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• pp.543-544
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• 2006

3-methyl-2-cyclopentenone is a valuable reaction intermediate for various high value added products. 3-methyl-2-cyclopentenone is not only expensive but also difficult to produce. 3-methyl-2-cyclopentenone can be synthesized by base catalyzed intermolecular aldol condensation. In this work, we studied a simple and practical method for synthesizing 3-methyl-2-cyclopentenone. Experimental results showed the advantages of the continuous flow process using a microreactor with kenic mixers for the synthesis of 3-methyl-2-cyclopentenone.

• Archives of Pharmacal Research
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• v.16 no.3
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• pp.205-208
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• 1993

($\pm$)-Myodesmone was synthesized, starting from 2-cyclopentenone. The key reaction involved $\alpha$-dimethoxymethylation of 2-cyclopentenone and organocopper conjugate addition reaction.

• Archives of Pharmacal Research
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• v.25 no.5
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• pp.590-599
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• 2002

Eight rigid compounds designed as esterase-stable analogues of methyl 2,5-dihydroxycinnamate (1) were synthesized. These derivatives include 2-(2',5'-dihydroxybenzylidene)cyclopentenone (3a), 2-(2',5'-dihydroxybenzylidene)cyclohexanone (3b), 2,6-bis(2',5'-dihydroxybenzy-lidene)cyclohexanone (4b), 2,6-bis(2',5'-dihydroxybenzylidene)cyclopentenone (4a), (E)-3-(2',5'-dihydroxybenzylidene)pyrrolidin-2-one (5), (E)-5-(2',5'-dihydroxybenzylidene )-1,2-isothiazolidine-1,1-dioxide (6), 4-(2',5'-dihydroxyphenyl)-5H-furan-2-one (7), and 3-(2',5'-dihydroxyphenyl)cyclopent-2-ene-1-one (8). Among the eight compounds, the furanone 7 and cyclopentenone 8 showed the most potent cytotoxicity with $IC_{50}$ values of 0.39-0.98 $\mu\textrm{g}$/mL. Compound 8 was further brominated, phenylated and methylated at the a position to give three corresponding analogues, including 2-bromo-3-(2',5'-dihydroxyphenyl)cyclopent-2-ene-1-one (24), 3-(2',5'-dihydroxyphenyl)-2-phenylcyclopent-2-ene-1-one (27), and 3-(2',5'-dihydroxyphenyl)-2-methylcyclopent-2-ene-1-one (28). Among the three, the most enhanced activity was observed with the phenylated compound 27.

• Proceedings of the PSK Conference
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• 2003.10b
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• pp.190.3-190.3
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• 2003

Three new butenolides (1-3), and a new cyclopentenone derivative (4) were isolated from a marine sponge Homaxinella sp. by bioactivity guided fractionation. The gross structures were established on the basis of NMR and MS analyses. The stereochemistry of the butenolides and cyclopentenone derivative was defined on the basis of optical rotation and CD spectroscopy. The compounds were tested against a panel of five human solid tumor cell lines and displayed marginal to significant cytotoxicity.

• The Korean Journal of Pesticide Science
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• v.5 no.1
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• pp.24-29
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• 2001

This study was conducted to investigate insecticidal activities of Ginkgo biloba (L.) leaves-derived bilobalide and its hydrolysis and oxidation products against adults of Nilaparavata lugens Stal. To find out active insecticidal moiety of bilobalide, decomposed intermediates and derivatives of bilobalide were made by hydrolysis, oxidation, and acetylation. The structures of hydrolysis product by base and oxidation product by acid were identified as cyclopentenone analogues and trilactone sesquiterpene from dehydration of bilobalide, respectively. Insecticidal activities of the decomposed intermediates and the derivatives of bilobalide decreased in the order of bilobalide, monoacetate, ginkgolide C, oxidation product, diacetate, and hydrolysis product. Therefore, trilactone structure of bilobalide may be essential for its insecticidal activity.

• Bulletin of the Korean Chemical Society
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• v.30 no.10
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• pp.2345-2350
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• 2009

As part of an effort to discover bioactive natural products from marine sources, we investigated the bioactive secondary metabolites from two marine isolates of the fungi, Trichoderma viride and Rhizopus stolonifer. Three cyclopentenones, myrothenones A (1) and B (2) and trichodenone A (3), were isolated from T. viride and two cyclopentenones, 2-bromomyrothenone B (4) and botrytinone (5), were isolated from R. stolonifer. The molecular structures and absolute stereochemistries of the cyclopentenones were determined from chemical and physicochemical evidence, including quantum chemistry calculations, X-ray analysis, and the circular dichroism (CD) exciton chirality method. Myrothenone A (1) displays tyrosinase inhibitory activity, with an I$C_{50}$ value of 6.6 ${\mu}M$, and is therefore more active than the positive control, kojic acid.

• Journal of the Korea Furniture Society
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• v.20 no.3
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• pp.198-204
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• 2009

Less used small diameter logs of black locust were heated at $250^{\circ}C$ for improving utilization. The volatile compounds emitted by the heated logs were analyzed. Their effect of formaldehyde absorption was evaluated with PB. Ester and acid compounds were dominant in content. Especially, methyl acetate and acetic acid showed the highest contents. The total content of aromatic compounds decreased as heating time increased. Amoung ketone compounds, The contents of 2-propanone, 2-pentanone, 3-petanone, 3-hexanone and cyclopentenone decreased with the increase of heating time, but the others did not. The contents of the chemicals, furfural and 3-pentanol, increased with heating time, while that of 2-methyl butanal decreased. It was hard to say that formaldehyde was absorbed by the heated black locust samples. Some decorative goods were designed with the heated logs.

• Journal of Life Science
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• v.18 no.11
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• pp.1485-1492
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• 2008

Prostaglandin $A_2$ ($PGA_2$), one of cyclopentenone PGs, induced both apoptosis and heme oxygenase (HO)-1 expression in U2OS cells. $PGA_2$-induced apoptosis was not perturbed by either over-expression or knock-down of HO-1, whereas $H_2O_2$-induced cell death was inversely modulated by the expression level of HO-1. In addition, N-acetyl-L-cysteine (NAC), a thiol antioxidant, blocked both apoptosis and HO-1 expression induced by $PGA_2$. But, non-thiol antioxidants like butylated hydorxyanisole (BHA) and ascorbic acid did not block either apoptosis or HO-1-induction. Taken together, these results suggest that $PGA_2$ induces both apoptosis and HO-1 expression, which are critically related to the thiol- reactivity of $PGA_2$, but not oxidative stress, and HO-1 expression may be independent or functionally located downstream of apoptosis by $PGA_2$ without contribution to apoptosis progression.

• ALGAE
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• v.27 no.1
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• pp.21-32
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• 2012

We report an oxidative burst triggered by prostaglandin $A_2(PGA_2)$ in the brown algal kelp Laminaria digitata, constituting the first such discovery in an alga and the second finding of an oxidative burst triggered by a prostaglandin in a living organism. The response is more powerful than the oxidative burst triggered by most other chemical elicitors in Laminaria. Also, it is dose-dependent and cannot be inhibited by diphenylene iodonium, suggesting that another source than NAD(P)H oxidase is operational in the production of reactive oxygen species. Despite the very strong oxidative response, rather few effects at other levels of signal transduction pathways could be identified. $PGA_2$ does not increase lipolysis (free fatty acids) in Laminaria, and only one oxylipin (15-hydroxyeicosatetraenoic acid; 15-HETE) was found to be upregulated in Laminaria. In a subsequent set of experiments in the genome model Ectocarpus siliculosus, none of 5 selected candidate genes, all established participants in various stress responses, showed any significant differences in their expression profiles.

• Asian Pacific Journal of Cancer Prevention
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• v.14 no.6
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• pp.3909-3919
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• 2013

The aim of the present investigation was to evaluate the effect of A ferruginea extract on Dalton's lymphoma ascites (DLA) induced tumours in BALB/c mice. Experimental animals received A ferruginea extract (10 mg/kg.b.wt) intraperitoneally for 14 consecutive days after DLA tumor challenge. Treatment with extract significantly increased the life span, total white blood cell (WBC) count and haemoglobin (Hb) content and decreased the level of serum aspartate transaminase (AST), alanine transaminase (ALT), alkaline phosphatase (ALP), gamma glutamyl transferase (${\gamma}$-GT) and nitric oxide (NO) in DLA bearing ascites tumor models. In addition, administration of extract significantly decreased the tumour volume and body weight in a DLA bearing solid tumor model. The levels of pro-inflammatory cytokines such as tumor necrosis factor-alpha (TNF-${\alpha}$), interleukin-1 beta (IL-$1{\beta}$), interleukin-6 (IL-6) and granulocyte monocyte-colony stimulating factor (GM-CSF), as well as pro-angiogenic growth factors such as vascular endothelial growth factor (VEGF) and inducible nitric oxide synthase (iNOS) were elevated in solid tumour controls, but significantly reduced by A ferruginea administration. On the other hand, the extract stimulated the production of interleukin-2 (IL-2) and interferon-gamma (IFN-${\gamma}$) in animals with DLA induced solid tumours. Increase in $CD4^+$ T-cell population suggested strong immunostimulant activity for this extract. GC/MS and LC/MS analysis showed quinone, quinoline, imidazolidine, pyrrolidine, cyclopentenone, thiazole, pyrazole, catechin and coumarin derivatives as major compounds present in the A ferruginea methanolic extract. Thus, the outcome of the present study suggests that A ferruginea extract has immunomodulatory and tumor inhibitory activities and has the potential to be developed as a natural anticancer agent.