• Journal of Microbiology and Biotechnology
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• 제16권7호
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• pp.1111-1119
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• 2006

Beauvericins and enniatins are cyclohexadepsipeptides exhibiting various biological activities on animal systems, including humans. Fusarium oxysporum FB1501 (KFCC 11363P) that produces four different cyclohexadepsipeptides was isolated from soil in Korea and the structures of the four cyclohexadepsipeptides elucidated by HPLC, MS, IR, and NMR analyses. The molecular weights for compounds 1,2,3, and 4 were determined to be 654.5, 784.5, 668.6, and 682.5, respectively, on the basis of ESI-MS measurements. The IR spectra for all the compounds exhibited absorptions for ester $(1,733-1,743\;cm^{-1})$ and amide $(1,649-1,655\;cm^{-1})$ bonds that were very similar to those for beauvericin and enniatins with ester and amide absorptions. The results of the NMR analysis $(^{1}H,\;^{13}C,\;135-DEPT,\;COSY,\;HMQC,\;and\;HMBC;\;in\;COCl_{3})$ revealed that compounds 1,3, and 4 consisted of $_{L}-N-methyl\;valine$ (N-MeVal), $_{D}-{\alpha}-hydroxyisovaleic\;acid$ (Hiv), and 2-hydroxy-3-methylpentanoic acid (Hmp) residues (compound 1: three N-MeVal residues, two Hiv residues, and one Hmp residue; compound 3: three N-MeVal residues, one Hiv, and two Hmp residues; compound 4: three N-MeVal residues and three Hmp residues). Therefore, the compounds were identified as enniatin H (compound 1), enniatin I (compound 3), and enniatin MK1688 (compound 4). Compound 2 was analyzed as beauvericin according to 1D and 2D NMR analyses. This study is the first report related to the co-production of beauvericin with other unusual enniatins, such as enniatin H, enniatin I, and enniatin MK1688, by Fusarium oxysporum.

• Bulletin of the Korean Chemical Society
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• 제31권1호
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• pp.146-150
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• 2010

A distinguished class of hydrophobic ionic liquids bearing a Br${\o}$nsted acidic character derived from amide-like compounds were prepared by a neutralization reaction of N,N-diethylformamide, N,N-dibutylformamide, 1-formylpiperidine, and $\varepsilon$-caprolactam with trifluoroacetic acid and physical absorptions of $CO_2$ in these ionic liquids were demonstrated and evaluated. $CO_2$ solubilities in these ionic liquids were influenced by the molecular structure of the cation and were apparently increased with the molar volume. Comparison based on a volume unit reveals that $CO_2$ solubilities in these liquids are relatively higher than those in imidazolium-based ionic liquids. Henry's coefficients calculated from low-pressure solubility tests at 313 to 333 K were used to derive the thermodynamics quantities. Enthalpy and entropy of solvation may share equal contributions in solubility.

• Archives of Pharmacal Research
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• 제28권6호
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• pp.637-647
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• 2005

This work includes the synthesis of 15 final compounds (6a-h and 7b-h) as prod rugs of 5-ASA in the form of the acid itself, esters and amides linked by an amide linkage through a spacer to the endocyclic ring N of nicotinamide. Also, 15 new intermediate compounds were prepared. The target compounds (6b, 6f, 7b, and 7e-h) revealed potent analgesic and anti-inflammatory activities in comparison to sulfasalazine and 5-ASA. In addition, ulcerogenicity, $LD_{50}$, in vivo and in vitro metabolism of compound 7f were determined.

• Bulletin of the Korean Chemical Society
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• 제11권4호
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• pp.333-339
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• 1990

A series of new dimesogenic compounds whose mesogens are of aromatic ester or amide type having a trifluoromethyl $(CF_3)$ substituent at the para-position of each terminal phenolic rings were prepared and their liquid crystalline properties were studied by differential scanning calorimetry (DSC) and on a cross-polarizing microscope. The compounds have two identical mesogenic units bracketing a central decamethylene spacer. Trifluoromethyl group appears to favor the formation of smectic phases when it is attached to a phenoxy or anilide terminal. Its group efficiency for mesophase formation seems to be inferior to other common substituents. A thermodynamic analysis of the phase transitions was made and the results were explained in relation to the structures of the compounds.

• 대한화학회지
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• 제24권6호
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• pp.457-462
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• 1980

Phosphoryl chloride와 allyl alcohol, 2,3-dibromopropanol, 2-pyrrolidone, ethylenimine을 반응하여 여러가지 phosphate와 phospshoric amide를 합성하였다. 합성한 화합물은 모두 열에 불안정하였으며, allyl phosphorodichloridate와 diallyl phosphorochloridate는 증류하면 상당량의 중합체가 생겼다. IR 스펙트라에서는 $1,300∼1,200 cm^{-1}$에서 P=O stretching의 특성밴드가 나타났으며 NMR 스펙트라는 인원자의 long range coupling 효과로 인해 복잡한 피이크를 보였다. 2,3-dibromopropyl phosphordichloridate의 mass 스펙트럼에서는 분자이온 피이크를 볼 수 없었다.

• Journal of Microbiology and Biotechnology
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• 제12권6호
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• pp.1006-1009
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• 2002

The biological activities of farnesoic acid derivatives against pathogenic fungi and bacteria were investigated. Farnesoic acid and its derivatives showed growth inhibitory activities against various bacteria. Among the compounds tested, geranylgeranoic acid (3) had potent antibacterial activity against Salmonella typhimurium, Proteus vulgaris, and Bacillus subtilis with minimum inhibitory concentration (MIC) in the range of $6.25-12.5{\mu}g/ml$. On the other hand, amide derivatives of farnesoic acid showed some antifungal activities. In particular, 3,7,11-trimethyl-dodeca-2,6,10-trienoic acid amide (5a) had a potent antifungal activity against Aspergillus niger, Candida albicans, and Trichophyton sp. with MIC in the range of $6.25-12.5{\mu}g/ml$.

• Bulletin of the Korean Chemical Society
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• 제29권5호
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• pp.993-997
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• 2008

Two directional ring-closing metathesis (RCM) was applied successfully to the synthesis of 4'-vinylated carbocyclic nucleoside analogues from the trivinyl intermediate 12, which was readily made using a sequential Claisen rearrangement and ring-closing metathesis (RCM) starting from Weinreb amide 5. An antiviral evaluation of the synthesized compounds against various viruses such as HIV, HSV-1, HSV-2 and HCMV revealed that the guanine analogue 20 have moderate anti-HIV activity in the MT-4 cell line ($EC_{50}$ = 10.2 $\mu$ M).

• Archives of Pharmacal Research
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• 제25권4호
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• pp.433-437
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• 2002

A new phenolic amide, dihydro-N-caffeoyltyramine (1) was isolated from the root bark of Lycium chinense Miller, along with known compounds, trans-N-caffeoyltyramine (2), cis-N-caffeoyltyramine (3), and lyoniresinol $3{\alpha}-Ο-{\beta}-D-glucopyranoside$ (4). Their structures were determined by spectroscopic analysis. A NBT superoxide scavenging assay revealed that three phenolic amides showed potent antioxidative activity.

• 한국동물학회지
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• 제13권3호
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• pp.75-84
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• 1970

蛋白質의 放射線分解의 기작을 밝히는 연구의 일환으로, 특히 peptide 結合의 분해의 기작을 구명하기 위하여 Glycylglycylglycine의 水溶液과 固體를 酸素의 존재하에서와 無酸素하에서 r 線을 조사하여 分解生成物을 여지크로마토그라프로 분리하였고, carbonyl 化合物과 amide를 각각 分光光度法과 微凉摘定法으로 정량하였으나 放射線障害를 평가하기 위하여 赤外線 spectrum과 紫外線 spectrum을 얻어 검토하였다. 水溶液과 固體에 있어서의 peptide 結合의 분해기작은 근본적인 차이가 있는 것으로 여겨지며, 전자에서는 월등하게 분해가 많이 일어난데 반해서 후자에서는 무시할 정도에 지나지 않았다. 한편, 水溶液의 경우 酸素의 유무에 따라 현저한 영향은 보이지 않았으나 無酸素하에서는 遊離基의 再結合이 일어나는 점이 특기할만 하였다. 水溶液에 있어서의 peptide 結合의 분해기구는 Garrison 一派가 주장한 기작에 의해서 일어나는 것이 분명하여 脫水素反應에 뒤이어 加水分解反應에 의해서 amide 와 carbonyl 이 생성되는 것으로 보이며, 固體의 경우도 $\\alpha$-炭素의 부위가 방사선의 공격을 가장 많이 받는 것으로 추정되나 그 정도는 미미한 것에 지나지 않는 것으로 생각되었다.

• 한국응용약물학회:학술대회논문집
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• 한국응용약물학회 1993년도 제2회 신약개발 연구발표회 초록집
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• pp.71-71
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• 1993

Carboxylesterase is widely distributed in the tissues of vertebrates, insects, plants and mycobacteria. Among various tissues of animals and humans, the highest esterase activity with various substrates is found in the liver. Kidney has moderate carboxylesterase activity in the proximal tubules. Considerable esterase activity is also found in the small intestine epithet elial cells and serum of mammals. Besides these tissues, carboxylesterase has been found in the lung, testis, adipose tissue, nasal mucosa and even in the central nervous system. Hepatic microsomal carboxylesterase catalyzes the hydrolysis of a wide variety of endogenous and exogenous compounds such as carboxylester, thioester and aromatic amide. Since carboxylesterases are important for metabolic activation of prodrugs and detoxification of xenobiotics, differences in substrate specificity and immunological properties of this enzyme are important in connection with choosing a suitable laboratory animal for the evaluation of biotransformation and toxicity of drugs. On the other hand, liver, kidney, intestine and serum were found to contain multiple forms of carboxylesterases in animal species and humans. In fact, we have purified more than fifteen isoforms of carboxylesterases from microsomes of liver, kidney and intestinal mucosa of nine animal species and humans. and characteristics of these isoforms were compared each other in terms of their physical and immunochemical properties. On the other hand, we have reported that hepatic microsomal carboxylesterases are induced by many exogenous compounds such as phenobarbital, polycyclic aromatic hydrocarbons, Aroclor 1254, aminopyrine and clofibrate. Later, we showed that some isoforms of hepatic carboxylesterase were induced by glucocorticoids such as dexamethasone and 16 ${\alpha}$-carbonitrile, but other isoforms were rather inhibited by these compounds. These findings indicate that involvement of carboxylesterases in the metabolism and toxicity of drugs should be explained by the isoforms involved. Since 1991, we have carried out detailed research investigating the types of carboxylesterases involved in the metabolic activation of CPT-11, a derivative of camptothecin, to the active metabolite, SN-38. The results obtained strongly suggest that some isoforms of carboxylesterase of liver microsomes and intestinal mucosal membrane are exclusively involved in CPT-11 metabolism. In this symposium, the properties of carboxylesterase isoforms purified from liver, kidney and intestine of animal species and humans are outlined. In addition, metabolism of CPT-11, a novel antitumor agent, by carboxylesterases in relation to the effectiveness will also be discussed.