• 한국정밀공학회:학술대회논문집
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• 한국정밀공학회 2006년도 춘계학술대회 논문집
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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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• 제16권3호
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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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• 제25권5호
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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.

• 대한약학회:학술대회논문집
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• 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2-2
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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.

• 농약과학회지
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• 제5권1호
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• pp.24-29
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• 2001

은행잎함유 살충성분인 bilobalide의 활성부위를 조사하기 위해 bilobalide를 가수분해 및 산화를 시킨 후 구조를 확인하고 살충활성을 검정하였다. 분해물의 분석 결과, 염기에 의한 가수분해물은 cyclopentenone 계열의 화합물로 밝혀졌고, 산화물은 trilactone 형태를 유지한 sesquiterpene 구조로써 dehydration된 형태로 추정되었다. 분해물의 살충활성을 검정한 결과, 살충력의 크기는 bilobalide, monoacetyl 유도체, ginkgolide C, 산화분해물, diacetyl 유도체, 가수분해물의 순으로 감소하여 bilobalide의 살충력을 나타내는데에는 trilactone의 구조를 유지하는 것이 중요한 것으로 나타났다.

• Bulletin of the Korean Chemical Society
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• 제30권10호
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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.

• 한국가구학회지
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• 제20권3호
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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.

• 생명과학회지
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• 제18권11호
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• pp.1485-1492
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• 2008

Prostaglandin $A_2$ ($PGA_2$)는 사람 골육종 세포인 U2OS 세포주에서 apoptosis와 heme oxygenase (HO)-1의 발현을 함께 유도하였다. $PGA_2$에 의한 apoptosis는 HO-1의 과도한 발현이나 HO-1에 대한 small interfering RNA에 의한 발현저하에 의하여 변동되지 않았으나 $H_2O_2$에 의한 세포사망은 HO-1의 발현 수준에 반비례하여 변동되었다. 또한 thiol antioxidant인 N-acetyl-L-cysteine (NAC)은 $PGA_2$에 의한 세포사망과 HO-1의 발현 증가를 모두 차단하였지만, non-thiol antioxidant인 butylated hydroxyanisole (BHA)과 ascorbic acid는 세포사망과 HO-1의 발현 유도를 차단하지 않았다. 이와 같은 결과들은 $PGA_2$는 산화성 손상에 의해서가 아니라 $PGA_2$의 thiol-reactivity에 의하여 apoptosis와 HO-1의 발현을 유도하며, HO-1의 발현은 $PGA_2$에 의한 apoptosis와는 독립적인 현상이거나 기능적으로 apoptosis 유도의 하부에 위치하고 apoptosis의 진행에는 기여하지 않을 것이라는 것을 시사해 준다.

• ALGAE
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• 제27권1호
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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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• 제14권6호
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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.