• 대한화학회지
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• 제34권2호
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• pp.179-183
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• 1990

배추좀나방의 성 페로몬을 새로운 방법으로 합성하여 EAG감응반응을 수행하였다. 프로파길알코올의 이중음이온을 알킬화하여 2-도데신-1-올을 얻고 이를 아세틸렌-지퍼반응에 의해 11-도데신-1-올로 전환시킨 다음, 다시 이중음이온 알킬화반응에 의해 11-헤사데신-1올을 얻었다. 이를 수소환원시켜 (Z)-11-헥사데센-1-올 (3)을 얻었고 이 알코올을 산화시켜 (Z)-11-헥사데센-1-알(1)을, 아세틸화시켜 (Z)-11-헥사데센-1-일 아세테이트(2)를 각각 얻었다. 이렇게 합성하여 얻어진 화합물 각각 또는 혼합물에 대해 배추좀나방의 ESG감응반응을 측정하였다.

• Applied Biological Chemistry
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• 제32권1호
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• pp.57-63
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• 1989

담배저장해충은 숙성된 엽연초에 가장 심각한 해를 끼치는 것으로 알려져 있다. 이 해충의 성유인 물질들 중에서 serricornin이 가장 강한 생리활성을 보여주고 다른 유인물질들은 교접시 이것에 대한 보조역할을 한다. 분광학적인 증거와 합성에 관한 연구로부터 이 화합물의 구조는 (4S,6S,7S)-4,6-dimethyl-7-hydroxynonan-3-one임이 밝혀졌다. 담배저장 해충으로부터 얻어진 성유인 물질들은 모두 polyketide 생합성의 과정에서 생성된다고 제안되었다. 두 가지 nonasymmetric 합성과 열가지 asymmetric 합성이 상세하게 고찰되었다.

• Bulletin of the Korean Chemical Society
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• 제29권5호
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• pp.959-962
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• 2008

We have performed FlexX docking experiments to predict the best docking poses of 5-androst-16-en-3-ol or 5-androst-16-en-3-one to Boar salivary lipocalin (SAL). Since no steroids were found inside of the binding pocket of the X-ray structure of 1GM6, we tried to find docking structures after opening the pocket using the random tweak option implemented in SYBYL. This operation allowed the ligand to enter the pocket. The best poses generated from FlexX were different from the structures reported earlier, which calculated docking poses by manual docking followed by minimization. Analysis of docking poses allowed us to identify pharmacophores. From this information, virtual screening experiments using UNITY were performed. Among six candidates, 3-(3,7-dimethyloct-6-enylamino)propane-1,2-diol (Leadquest code name: 5755) was chosen for further development. Future work will involve synthesis of some derivatives of 5755 and biological experiments if any derivatives can control the biostimulation and improve reproductive efficiency in pigs.

• The Korean Journal of Physiology and Pharmacology
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• 제19권3호
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• pp.269-274
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• 2015

Chronic inflammation has been proposed as one of the main molecular mechanisms of aging and age-related diseases. Although evidence in humans is limited, short-term calorie restriction (CR) has been shown to have anti-inflammatory effects in aged experimental animals. We reported on the long-term treatment of daumone, a synthetic pheromone secreted by Caenorhabditis elegans in an energy deficient environment, extends the life-span and attenuates liver injury in aged mice. The present study examined whether late onset short-term treatment of daumone exerts anti-inflammatory effects in the livers of aged mice. Daumone was administered orally at doses of 2 or 20 mg/kg/day for 5 weeks to 24-month-old male C57BL/6J mice. Increased liver macrophage infiltration and gene expression of proinflammatory cytokines in aged mice were significantly attenuated by daumone treatment, suggesting that short-term oral administration of daumone may have hepatoprotective effects. Daumone also dose-dependently suppressed tumor necrosis factor-${\alpha}$ (TNF-${\alpha}$ )-induced nuclear factor-${\kappa}B$ (NF-${\kappa}B$) phosphorylation in HepG2 cells. The present data demonstrated that short-term treatment of daumone has anti-inflammatory effects in aged mouse livers possibly through suppression of NF-${\kappa}B$ signaling and suggest that daumone may become a lead compound targeting aging and age-associated diseases.

• Entomological Research
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• 제48권5호
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• pp.448-452
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• 2018

The aggregation pheromone of Monochamus (Coleoptera: Cerambycidae) beetles, 2-(undecyloxy) ethanol (hereafter referred to as monochamol), has gained considerable attention because of its usefulness in monitoring and population control of pine sawyer beetles. The hydroxyether structural motif is conserved in pheromones of the subfamily Lamiinae of the Cerambycidae. In this study, we investigated the effects of C10- and C12-chain length alkyl analogs of monochamol, 2-(decyloxy) ethanol and 2-(dodecyloxy) ethanol, on attracting M. saltuairus in Andong, Gyeongsangbuk-do, Korea. The C10 and C12 analogs attracted M. saltuarius when used in combination with ${\alpha}$-pinene and ethanol, but the responses of these alkyl chain analogs were lower than those of monochamol. Furthermore, the addition of either C10 or C12 analog to the use of monochamol with ${\alpha}$-pinene and ethanol had no effect on attraction of M. saltuarius, indicating high sensitivity of M. saltuarius to monochanol. Taken together, the results of this study suggest that chemical communication within a Monochamus species depends not only on monochamol, but also on other semiochemicals.

• Molecules and Cells
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• 제26권5호
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• pp.503-513
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• 2008

The vomeronasal organ (VNO) is a sensory organ that influences social and/or reproductive behavior and, in many cases, the survival of an organism. The VNO is believed to mediate responses to pheromones; however, many mechanisms of signal transduction in the VNO remain elusive. Here, we examined the expression of proteins involved in signal transduction that are found in the main olfactory system in the VNO. The localization of many signaling molecules in the VNO is quite different from those in the main olfactory system, suggesting differences in signal transduction mechanisms between these two chemosensory organs. Various signaling molecules are expressed in distinct areas of VNO sensory epithelium. Interestingly, we found the expressions of groups of these signaling molecules in glandular tissues adjacent to VNO, supporting the physiological significance of these glandular tissues. Our finding of high expression of signaling proteins in glandular tissues suggests that neurohumoral factors influence glandular tissues to modulate signaling cascades that in turn alter the responses of the VNO to hormonal status.

• Reproductive and Developmental Biology
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• 제31권1호
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• pp.15-20
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• 2007

가축의 번식과 수요를 조절할 수 있는 생물학적 자극 통제 수단으로 새로운 돼지 페르몬성 냄새 물질를 탐색하고자, 기질 분자로서 2-cyclohexyloxytetrahydrofurane (A), 2-phenoxytetrahydrofurane (B) 유도체들의 설명인자인 물리화학 파라미터와 돼지 페로몬의 수용체 (pOBP)에 대한 결합 친화력 상수($p[Od.]_{50}$) 간의 2D-QSAR 모델을 유도하고 검토하였다. 2D-QSAR 모델은 결합 친화력 상수를 약 96.4% 설명하는 매우 양호한 모델($r^{2}=0.964$)로서 분자내 치환기의 소수성 (SL) 상수에 관한 적정값이 $(SL)_{opt.}=1.418$일 때 가장 높은 결합 친화력을 나타냄을 알았다. 그러므로 분자내 치환기의 소수성 인자가 결합 친화력 상수에 가장 큰 영향을 미치는 중요한 요소이었다.

• 한국발생생물학회지:발생과생식
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• 제6권1호
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• pp.31-35
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• 2002

생쥐에서 페르몬으로 알려진 소수성의 분자와 결합하는 major urinary proteins(MUPs)는 부분적으로 성장 호르몬(GH)의 조절을 받는다. 본 연구에서는 MT-GRF로 형질전환되어 성장호르몬이 증가된 생쥐에서 MUP의 발현을 조사하였다. 이 MT-GRF로 형질전환된 생쥐의 소변에서 MUP이 대조군보다 심하게 저하되어 나타났고, 암컷보다 수컷에서 더 저하되어 나타났다. 또한 MT-GRF를 근육에 주사한 생쥐에서도 MUP는 저하되어 나타났다. 부가하여, MT-GRF로 형질전환시킨 생쥐의 소변에서 전기영동상에서 albumin과 동일하게 이동하는 고분자의 단백질이 다량으로 관찰되었는데 신장의 사구체 여과가 손상되었음을 암시하고 있다. 이 혈장 단백질의 손실도 암컷보다 수컷에서 심하게 나타났다. 결과적으로 GRF의 과다생성은 성별에 차별화된 영향을 미치면서 GH로 형질전환된 동물모델에서 관찰되는 MUP의 발현과 사구체 기능의 변화를 동일하게 유발하고 있었다.

• Journal of Ginseng Research
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• 제34권1호
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• pp.17-22
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• 2010

Sesquiterpenes are found naturally in plants and insects as defensive agents or pheromones. They are produced in the cytosolic acetate/mevalonate pathway for isoprenoid biosynthesis. The inducible sesquiterpene synthases (STS), which are responsible for the transformation of the precursor farnesyl diphosphate, appear to generate very few olefinic products that are converted to biologically active metabolites. In this study, we isolated the STS gene from Panax ginseng C.A. Meyer, designated PgSTS, and investigated the correlation between its expression and various abiotic stresses using real-time PCR. PgSTS cDNA was observed to be 1,883 nucleotides long with an open reading frame of 1,707 bp, encoding a protein of 568 amino acids. The molecular mass of the mature protein was determined to be 65.5 kDa, with a predicted isoelectric point of 5.98. A GenBank BlastX search revealed the deduced amino acid sequence of PgSTS to be homologous to STS from other plants, with the highest similarity to an STS from Lycopersicon hirsutum (55% identity, 51% similarity). Real-time PCR analysis showed that different abiotic stresses triggered significant induction of PgSTS expression at different time points.

• Reproductive and Developmental Biology
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• 제28권1호
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• pp.45-52
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• 2004

To search a new porcine pheromonal odorants, this research for biostimulation and role of pheromone was augmented by means of "control system technologies" to offer a potentially useful and practical way to improve reproductive efficiency in livestock species. Therefore the 13 physicochemical parameters such as similarity indice (S), hydrophobicity (logP) and van der Waals molecule volume (MV) etc. of 54 steroid analogues, which are analogous of substrate molecules, 5$\alpha$-androst-16-en-3-one (P1) and 5$\alpha$-androst-16-en-3-ol (P2) of lipocalin as receptor of pig pheromones were calculated and discussed. The physicochemical properties of these steroid analogues were mainly followed by steric dissimilar of A and D ring in steroid nucleus. And we found that from correlation with S values and MV constants of molecules, the more MV constants are small, the more S values tend to approach 1. Based on this results, the S-values of 4-androsten-3,17-dione (P1-1) and 5 $\alpha$ -androstan-3-one (P2-1) were 1.0, respectively. The two compounds of them were chosen because they showed the same value each other at a side of hydrophobicity, molar refractivity and molecular volume. It is expected that the new two compounds will be able to substitute for P1 and P2, porcine pheromonal odorants.