• Korean Journal of Pharmacognosy
• /
• v.44 no.4
• /
• pp.336-343
• /
• 2013

In a continuation of investigation on Cordyceps militaris, thirteen compounds were isolated from the $CH_2Cl_2$ and n-BuOH-soluble fraction of C. militaris. They were identified as twelve diketopiperazines such as cyclo($\small{L}$-Gly-$\small{L}$-Pro) (1), cyclo($\small{L}$-Ala-$\small{L}$-Pro) (2), cyclo($\small{L}$-Ser-$\small{L}$-Pro) (3), cyclo($\small{L}$-Val-$\small{L}$-Pro) (4), cyclo($\small{L}$-Thr-$\small{L}$-Pro) (5), cyclo($\small{L}$-Pro-$\small{L}$-Pro) (6), cyclo($\small{L}$-Thr-$\small{L}$-Leu) (7), cyclo($\small{L}$-Tyr-$\small{L}$-Ala) (8), cyclo($\small{L}$-Phe-$\small{L}$-Ser) (9), cyclo($\small{L}$-Phe-$\small{L}$-Pro) (10), cyclo($\small{L}$-Tyr-$\small{L}$-Pro) (11) and brevianamide F (13), and an amino acid, tryptophan (12). Their structures were identified on the basis of chemical evidences and spectroscopic analysis including 1D-NMR ($^1H$, $^{13}C$), 2D-NMR (HSQC, HMBC) and MS spectral data. Among the isolated compounds, compounds 1, 2, 6-11 are first reported from C. militaris.

• Korean Journal of Microbiology
• /
• v.52 no.4
• /
• pp.415-420
• /
• 2016

Chemical study of an Arctic bacterium, Pseudomonas aeruginosa (Pseudomonadaceae) led to the isolation of two diketopiperazines 1 and 2, two phenazine alkaloids 3 and 4, and an indole carbaldehyde 5, along with a benzoic acid derivative 6. The structures of the compounds were confirmed by 1D and 2D NMR, and MS experiments, as well as by comparison of their data with published values. Among the isolates, compounds 5 and 6 were isolated for the first time from P. aeruginosa of the seawater of Arctic Chuckchi Sea. Antimicrobial activities of compounds 1‒6 against a Staphylococcus aureus and Candida albicans were evaluated.

• Journal of the Korean Chemical Society
• /
• v.59 no.6
• /
• pp.545-550
• /
• 2015

• Proceedings of the Korean Society of Applied Pharmacology
• /
• 1997.11a
• /
• pp.19-25
• /
• 1997

Bicyclomycin(BCM)은 1972년에 일본 Hokkaido, Sapporo지방의 토양균중의 하나인 Streptomyces Sapporoneosis의 배양액으로부터 최초로 분리된 항생물질로서 특히 Gram(-) 박테리아인 Escherichia coli. Klebsiella, Shigella, Salmonella, Citrobacter, Enterobacter cloacae, Neisseria gonorrhoeae등에 대한 선택적인 항균효과를 가지고 있고 Streptomycin, Kanamycin, Chloramphenicol, Tetracyclin, Aminobenzylpenicillin 및 naldixic acid 등에 대해 교차내성을 가지고 있지 않다. BCM은 구조적인 면에서 [4.2.2]bicyclic구조를 가지고있는 특이한 항생물질로서 C(1)-triol부분, diketopiperazine부분 그리고 C(5)-C(5a)exomethylene의 3 부분으로 크게 나눌수 있다(Fig. 1). BGM은 E. coli에 대한 항균력으로서 250-500 $\mu\textrm{g}$/mL의 MIC value를 가지고 있고 급성독성으로서 LD$_{50}$가 4g/kg 이상으로 거의 독성이 없는 것이 특징이다. 현재 Fujisawa pharmaceutical Ltd.로부터 Bicozamycin이라는 상품명으로 설사치료제 용도로 시판되고 있다.

• Korean Journal of Microbiology
• /
• v.44 no.2
• /
• pp.85-92
• /
• 2008

Pseudomonas aeruginosa is an opportunistic human pathogen, causing a wide variety of infections including cystic fibrosis, microbial keratitis, and burn wound infections. The cell-to-cell signaling mechanism known as quorum sensing (QS) plays a key role in these infections and the QS systems of P. aeruginosa have been most intensively studied. While many literatures that introduce the QS systems of P. aeruginosa have mostly focused on two major acyl-homo serine lactone (acyl-HSL) QS signals, N-3-oxododecanoyl homoserine lactone (3OC12) and N-butanoyl homoserine lactone (C4), several new signal molecules have been discovered and suggested for their significant roles in signaling and virulence of P. aeruginosa. One of them is PQS (Pseudomonas quinolone signal; 2-heptyl-3-hydroxy-4-quinolone), which is now considered as a well-characterized major signal meolecule of P. aeruginosa. In addition, recent researches have also suggested some more putative signal molecules of P. aeruginosa, which are diketopiperazines (DKPs) and pyocyanin. DKPs are cyclic dipeptides and structurally diverse depending on what amino acids are involved in composition. Some DKPs from the culture supernatant of P. aeruginosa are suggested as new diffusible signal molecules, based on their ability to activate Vibrio fischeri LuxR biosensors that are previously considered specific for acyl-HSLs. Pyocyanin (1-hydroxy-5-methyl-phenazine), one of phenazine derivatives produced by P. aeruginosa is a characteristic blue-green pigment and redox-active compound. This has been recently suggested as a terminal signaling factor to upregulate some QS-controlled genes during stationary phase under the mediation of a transcription factor, SoxR. Here, details about these newly emerging signaling molecules of P. aeruginosa are discussed.

• Korean Journal of Microbiology
• /
• v.54 no.1
• /
• pp.18-23
• /
• 2018

A new naturally occurring benzoic acid derivative, benzyl 2,4-di(benzyloxy)benzoate (1) and six known compounds (2-7) were isolated from the fungus, Preussia sp. found in frozen soil of the Himalaya Mountain. The structures of the new compound, together with the known compounds were determined by 1D-and 2D-NMR experiments, as well as comparison with published values. In addition, to the best of our knowledge, the known compounds 2-7 were isolated for the first time from the genus Preussia and the family Sporormiaceae. The isolates were evaluated for cancer chemopreventive potential based on their ability to inhibit nitric oxide (NO) production induced by lipopolysaccharide (LPS) in mouse macrophage RAW 264.7 cells in vitro. Compounds 1 and 2 inhibited NO production by 50.7% and 88.5% at a concentration of 100 mg/ml, respectively.

• Bulletin of the Korean Chemical Society
• /
• v.35 no.8
• /
• pp.2299-2303
• /
• 2014

Two diastereoisomers of cyclo(Pro-Tyr) have been synthesized simultaneously. The crystal structures and conformations of both cyclo($\small{L}$-Pro-$\small{L}$-Tyr) and a racemic mixture of cyclo($\small{D}$-Pro-$\small{L}$-Tyr) and cyclo($\small{L}$-Pro-$\small{D}$-Tyr), abbreviated as rac-cyclo($\small{D}$-Pro-$\small{L}$-Tyr/$\small{L}$-Pro-$\small{D}$-Tyr), have been determined by a single-crystal X-ray diffraction study at low temperature. The crystals of rac-cyclo($\small{D}$-Pro-$\small{L}$-Tyr/$\small{L}$-Pro-$\small{D}$-Tyr) belong to orthorhombic space group $Pna2_1$ with a = 10.755 (1), b = 12.699 (1), c = 9.600 (1) ${\AA}$ and Z = 4. The tyrosine side chain is folded towards the diketopiperazine (DKP) ring. The DKP ring adopts a twist boat conformation with pseudo symmetry $C_{2v}$. The pyrrolidine ring has an envelope conformation with the N5, C4, C7 and C8 atoms in a plane. The crystal of rac-cyclo($\small{D}$-Pro-$\small{L}$-Tyr/$\small{L}$-Pro-$\small{D}$-Tyr) is stabilized by hydrogen bonds between amide N2-H2 and carbonyl oxygen O2 in the neighbor. The hydroxyl group of tyrosine residue is also hydrogen bonded to the oxygen of the carbonyl group of the DKP ring in the next molecule. The spectroscopic properties of both isomers are also described.

• KSBB Journal
• /
• v.28 no.4
• /
• pp.217-224
• /
• 2013

A bacterium CGH18 exhibiting antioxidizing and chitin-degrading activities in the colloidal chitin culture medium was isolated from salt-fermented crab. This strain was identified as Bacillus idriensis based on 16S rDNA sequence homology search. Its crude extract was partitioned between n-BuOH and $H_2O$. The organic layer was further partitioned between $CH_2$ $Cl_2$ and $H_2O$. Antioxidant activities of crude extract and its solvent fractions were evaluated using five different bioassay methods, including the degree of occurrence of intracellular reactive oxygen species (ROS), peroxynitrite scavenging (ONOO), and oxidative damage of genomic DNA. All fractions exhibited significant antioxidant activity in bioassay systems used.

• Korean Journal of Food Science and Technology
• /
• v.28 no.2
• /
• pp.311-315
• /
• 1996

Thermal stability of aspartame was investigated as affected by the temperature and pH during heating. The thermal stability study of aspartame heated at $60-100^{\circ}C$ showed that aspartame was degraded more rapidly as the heating temperature increased. Activation energy for thermal degradation was 20.77 kcal/mol. The thermal degradation products, a diketopiperazine (DKP) and ${\alpha}$-aspartylphenylalanine (${\alpha}$-AP), were rapidly increased while the aspartame concentration decreased. The pH change of aspartame solution was rapidly decreased during initial three hours of heating and more significant at high temperature. In the pH range ()』 3-7, aspartame was the most unstable at pH 7 and stable at pH 4. The thermal degradation rate contants were 0.827 at pH 7, 0.286 at pH 6, 0.072 at pH 5 and 0.045 at pH 4 during initial heating at $100^{\circ}C$.