• 제목/요약/키워드: Lactone

검색결과 336건 처리시간 0.031초

The Inhibitory Principle of Lipopolysaccharide-Induced Nitric Oxide Production from Inula Britannica var. Chinensis

  • Je, Kang-Hoon;Han, Ah-Reum;Lee, Hyun-Tai;Mar, Woong-Chon;Seo, Eun-Kyoung
    • Archives of Pharmacal Research
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    • 제27권1호
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    • pp.83-85
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    • 2004
  • A sesquiterpene lactone, 1-O-acetyl-4R,6S-britannilactone (1) isolated from the flowers of Inula britannica L. var. chinensis (Rupr.) Reg. (Compositae), was found as an iNOS inhibitory constituent for the first time with an $IC_{50}$ value of 22.1 $\mu$ M which is more potent than the positive control, L-$N^6$-(1-iminoethyl)lysine ($IC_{50} =33.7 \mu$ M). Structure of compound 1 was identified by 1D and 2D NMR experiments and by comparison with the reference standard.

Cytotoxic Lactones from the Pericarps of Litsea japonica

  • Ngo, Quynh-Mai Thi;Cao, Thao Quyen;Woo, Mi Hee;Min, Byung Sun
    • Natural Product Sciences
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    • 제25권1호
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    • pp.23-27
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    • 2019
  • From the pericarps of Litsea japonica (Thunb.) Jussieu, eighteen butanolide derivatives (1 - 18) were evaluated for their cytotoxic activity against HeLa, HL-60, and MCF-7 cells. Compounds 1-9 with 2-alkylidene-3-hydroxy-4-methylbutanolides structure exhibited cytotoxic activities against cancer-cell lines. Among them, compound 8 (litsenolide $D_2$) exhibited the most potent cytotoxicity against the tested cell lines, including HeLa, HL-60, and MCF-7, with $IC_{50}$ values of $17.6{\pm}1.3$, $4.2{\pm}0.2$, and $12.8{\pm}0.0{\mu}M$, respectively. Compound 8 induced apoptosis in a dose-dependent manner. Annexin V/Propidium Iodide (PI) double staining confirmed that 8 effectively induced apoptosis in MCF-7 cells. To the best of our knowledge, we have reported cytotoxic activity of butanolides from L. japonica against these cancer-cell lines for the first time.

Suppressoin of NF-$_k$B signaling pathways by ergolide in HeLa cells

  • Yoon, Jong-Woo;Chun, Jae-Kwang;Cho, Eun-Jung;Han, Jeung-Whan;Lee, Hyang-Woo
    • 대한약학회:학술대회논문집
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    • 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.1
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    • pp.217.1-217.1
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    • 2003
  • In previous study, we investigated the mechanism of suppression of inducible nitric oxide synthase (iNOS) and cyclo-oxygenase-2 (COX-2) by ergolide, sesquiterpene lactone from Inula Britannica. In this study, the suppression of iNOS and COX-2 by ergolide might be attributed to selective inhibition of NF-$\_$K/B signaling pathways. Here, we investigated the suppressionmechanism of NF-$\_$K/B signaling pathways by ergolide in TPA-stimulated HeLa cells. (omitted)

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Total Synthesis of Bacillariolide III

  • Suh, Young-Ger;Seo, Seung-Yong;Paek, Seung-Mann;Jung, Jae-Kyung;Han, Young-Taek;Kim, Seok-Ho
    • 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.65.3-66
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    • 2003
  • Bacillariolide III was isolated from the culture medium of the marine diatom, Pseudonitzschia multi series, a causative organism of amnesic shellfish poisoning by Shimizu et al. This extracellular metabolite features bicyclic system of hydroxycyclopentane and (Z)-pentenoic acid-bearing lactone ring. Bacillariolide I is known to possess significant inhibitory activity against phospholipase A$_2$, but the biological function of bacillariolide III is still under investigation. The unique structural feature as well as the promising biological activity led us to the total synthesis of bacillariolide III. (omitted)

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함박꽃나무(Magnolia sieboldii)의 추출성분 (Extractives from Magnolia siebildii)

  • 최인호;이학주;최돈하;박재인;최태호
    • Journal of the Korean Wood Science and Technology
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    • 제32권2호
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    • pp.33-39
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    • 2004
  • 함박꽃나무 수피 및 목부의 EtOH 조추출물로부터 prep. TLC, silica gel 및 Sephadex LH-20 칼럼 크로마토그라피를 이용하여 4종의 화합물을 단리하였다. 이들 화합물들은 NMR, MS 등의 기기분석에 의해 sesquiterpene lactone 구조의 costunolide (I)를 비롯하여, 리그난 배당체 화합물인 syringin (II)과 1, 2-dihydroxyxanthone (III) 및 vanillic acid (IV)으로 각각 동정하였다.

제주도 방선균 유래 oxazolomycin 계열 KSM-2690 B의 구조 결정과 항균활성에 관한 연구 (Structure Elucidation and Antibacterial Activity of Oxazolomycin Family KSM-2690 B Derived from Actinomycete Collected in Jeju Island)

  • 정형주;김주영;엄수현;문규호
    • 생약학회지
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    • 제54권1호
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    • pp.16-20
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    • 2023
  • KSM-2690 B (1), a peptide-polyketide hybrid compound, was discovered from an actinomycete strain (CJD 1) isolated from Dong-Baek hill on Jeju Island, Republic of Korea. The chemical structure of 1 was identified by using NMR, MS, and UV spectroscopic analyses. Careful analysis of 1D and 2D NMR data revealed that KSM-2690 (1) has an oxazole ring, a β-lactone-γ-lactam spirocycle ring, and both triene and diene structures. KSM-2690 B (1) showed inhibitory activities against E. coli at 200 ㎍/mL.

Sesquiterpenoids Bioconversion Analysis by Wood Rot Fungi

  • Lee, Su-Yeon;Ryu, Sun-Hwa;Choi, In-Gyu;Kim, Myungkil
    • 한국균학회소식:학술대회논문집
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    • 한국균학회 2016년도 춘계학술대회 및 임시총회
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    • pp.19-20
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    • 2016
  • Sesquiterpenoids are defined as $C_{15}$ compounds derived from farnesyl pyrophosphate (FPP), and their complex structures are found in the tissue of many diverse plants (Degenhardt et al. 2009). FPP's long chain length and additional double bond enables its conversion to a huge range of mono-, di-, and tri-cyclic structures. A number of cyclic sesquiterpenes with alcohol, aldehyde, and ketone derivatives have key biological and medicinal properties (Fraga 1999). Fungi, such as the wood-rotting Polyporus brumalis, are excellent sources of pharmaceutically interesting natural products such as sesquiterpenoids. In this study, we investigated the biosynthesis of P. brumalis sesquiterpenoids on modified medium. Fungal suspensions of 11 white rot species were inoculated in modified medium containing $C_6H_{12}O_6$, $C_4H_{12}N_2O_6$, $KH_2PO_4$, $MgSO_4$, and $CaCl_2$ for 20 days. Cultivation was stopped by solvent extraction via separation of the mycelium. The metabolites were identified as follows: propionic acid (1), mevalonic acid lactone (2), ${\beta}$-eudesmane (3), and ${\beta}$-eudesmol (4), respectively (Figure 1). The main peaks of ${\beta}$-eudesmane and ${\beta}$-eudesmol, which were indicative of sesquiterpene structures, were consistently detected for 5, 7, 12, and 15 days These results demonstrated the existence of terpene metabolism in the mycelium of P. brumalis. Polyporus spp. are known to generate flavor components such as methyl 2,4-dihydroxy-3,6-dimethyl benzoate; 2-hydroxy-4-methoxy-6-methyl benzoic acid; 3-hydroxy-5-methyl phenol; and 3-methoxy-2,5-dimethyl phenol in submerged cultures (Hoffmann and Esser 1978). Drimanes of sesquiterpenes were reported as metabolites from P. arcularius and shown to exhibit antimicrobial activity against Gram-positive bacteria such as Staphylococcus aureus (Fleck et al. 1996). The main metabolites of P. brumalis, ${\beta}$-Eudesmol and ${\beta}$-eudesmane, were categorized as eudesmane-type sesquiterpene structures. The eudesmane skeleton could be biosynthesized from FPP-derived IPP, and approximately 1,000 structures have been identified in plants as essential oils. The biosynthesis of eudesmol from P. brumalis may thus be an important tool for the production of useful natural compounds as presumed from its identified potent bioactivity in plants. Essential oils comprising eudesmane-type sesquiterpenoids have been previously and extensively researched (Wu et al. 2006). ${\beta}$-Eudesmol is a well-known and important eudesmane alcohol with an anticholinergic effect in the vascular endothelium (Tsuneki et al. 2005). Additionally, recent studies demonstrated that ${\beta}$-eudesmol acts as a channel blocker for nicotinic acetylcholine receptors at the neuromuscular junction, and it can inhibit angiogenesis in vitro and in vivo by blocking the mitogen-activated protein kinase (MAPK) signaling pathway (Seo et al. 2011). Variation of nutrients was conducted to determine an optimum condition for the biosynthesis of sesquiterpenes by P. brumalis. Genes encoding terpene synthases, which are crucial to the terpene synthesis pathway, generally respond to environmental factors such as pH, temperature, and available nutrients (Hoffmeister and Keller 2007, Yu and Keller 2005). Calvo et al. described the effect of major nutrients, carbon and nitrogen, on the synthesis of secondary metabolites (Calvo et al. 2002). P. brumalis did not prefer to synthesize sesquiterpenes under all growth conditions. Results of differences in metabolites observed in P. brumalis grown in PDB and modified medium highlighted the potential effect inorganic sources such as $C_4H_{12}N_2O_6$, $KH_2PO_4$, $MgSO_4$, and $CaCl_2$ on sesquiterpene synthesis. ${\beta}$-eudesmol was apparent during cultivation except for when P. brumalis was grown on $MgSO_4$-free medium. These results demonstrated that $MgSO_4$ can specifically control the biosynthesis of ${\beta}$-eudesmol. Magnesium has been reported as a cofactor that binds to sesquiterpene synthase (Agger et al. 2008). Specifically, the $Mg^{2+}$ ions bind to two conserved metal-binding motifs. These metal ions complex to the substrate pyrophosphate, thereby promoting the ionization of the leaving groups of FPP and resulting in the generation of a highly reactive allylic cation. Effect of magnesium source on the sesquiterpene biosynthesis was also identified via analysis of the concentration of total carbohydrates. Our current study offered further insight that fungal sesquiterpene biosynthesis can be controlled by nutrients. To profile the metabolites of P. brumalis, the cultures were extracted based on the growth curve. Despite metabolites produced during mycelia growth, there was difficulty in detecting significant changes in metabolite production, especially those at low concentrations. These compounds may be of interest in understanding their synthetic mechanisms in P. brumalis. The synthesis of terpene compounds began during the growth phase at day 9. Sesquiterpene synthesis occurred after growth was complete. At day 9, drimenol, farnesol, and mevalonic lactone (or mevalonic acid lactone) were identified. Mevalonic acid lactone is the precursor of the mevalonic pathway, and particularly, it is a precursor for a number of biologically important lipids, including cholesterol hormones (Buckley et al. 2002). Farnesol is the precursor of sesquiterpenoids. Drimenol compounds, bi-cyclic-sesquiterpene alcohols, can be synthesized from trans-trans farnesol via cyclization and rearrangement (Polovinka et al. 1994). They have also been identified in the basidiomycota Lentinus lepideus as secondary metabolites. After 12 days in the growth phase, ${\beta}$-elemene caryophyllene, ${\delta}$-cadiene, and eudesmane were detected with ${\beta}$-eudesmol. The data showed the synthesis of sesquiterpene hydrocarbons with bi-cyclic structures. These compounds can be synthesized from FPP by cyclization. Cyclic terpenoids are synthesized through the formation of a carbon skeleton from linear precursors by terpene cyclase, which is followed by chemical modification by oxidation, reduction, methylation, etc. Sesquiterpene cyclase is a key branch-point enzyme that catalyzes the complex intermolecular cyclization of the linear prenyl diphosphate into cyclic hydrocarbons (Toyomasu et al. 2007). After 20 days in stationary phase, the oxygenated structures eudesmol, elemol, and caryophyllene oxide were detected. Thus, after growth, sesquiterpenes were identified. Per these results, we showed that terpene metabolism in wood-rotting fungi occurs in the stationary phase. We also showed that such metabolism can be controlled by magnesium supplementation in the growth medium. In conclusion, we identified P. brumalis as a wood-rotting fungus that can produce sesquiterpenes. To mechanistically understand eudesmane-type sesquiterpene biosynthesis in P. brumalis, further research into the genes regulating the dynamics of such biosynthesis is warranted.

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탈지 대두분을 이용하여 제조한 두부의 품질 특성에 영향을 미치는 인자 (A Study on the Soybean Curd(Tofu) made from Defatted Soybean Flour)

  • 김진희;우은열;김강성;김명희
    • 한국식품영양학회지
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    • 제19권1호
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    • pp.22-27
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    • 2006
  • 탈지 대두분을 이용하여 두부를 제조함에 있어 각 공정의 최적조건을 알아보았다. 탈지 대두분을 물과 1:9 (wt/wt)의 비율로 혼합하고 용액을 교반하면서 가열하였다. 탈지 대두분 두유를 $80^{\circ}C$ 이상으로 가열해야 응고제를 가할 경우 단백질이 응고현상을 보였으며 두부의 형태로 만들 수 있었다. 한편 탈지 대두분 두유의 가열 온도 $80^{\circ}C$에서 가장 높은 수율로 두부가 제조되었다. 두부의 수분 함량 역시 탈지 대두분 두유 가열 온도에 의해 영향을 받는 것으로 나타났다. $85{\sim}90^{\circ}C$에서 77%로 가장 높은 수분 함량을 나타내었다. 따라서 $80^{\circ}C$이상으로 탈지 대두분 두유를 가열하는 과정이 두부 제조에 필수적인 과정인 것으로 판단된다. 탈지 대두분 두유의 가열시간의 경우, 5분 미만일 때 응고현상을 나타내지 않았고 가열시간이 $5{\sim}10$분일때 두부의 무게가 증가하는 경향을 보였으며 수분함량은 $1{\sim}10$분 사이일 경우 80% 정도로 유지되었으나 10분을 초과할 경우 수분함량이 감소하는 것으로 나타났다. 따라서 두부를 $5{\sim}10$분 가량 가열하는 것이 대두 단백질의 변성이 충분하게 일어나고 두부의 수분 함랑도 적절하게 유지되는 것으로 사료된다. 지방질을 20 g 첨가하였을 때 두부의 무게와 수분함량이 가장 높았으며 그 이상으로 첨가하였을 때는 두부의 무게와 수분 함량이 감소하는 경향을 나타냈다. 이는 높은 지방 함량이 두부 조직과 물 분자 사이의 결합을 방해하기 때문인 것으로 사료된다. 글루코노 델타 락톤 첨가량이 증가함에 따라 제조된 두부의 무게는 비례하게 증가되었고 12 g 이상 첨가된 두부의 무게는 일정한 수준을 유지하였다. 글루코노 델타 락톤 첨가량은 견고성에 영향을 끼치는데 첨가량이 5 g일 때 가장 단단한 두부가 만들어졌으며 그 이상을 첨가하면 견고성은 감소하다 추가적인 글루코노 델타 락톤 첨가에도 거의 일정한 수준을 유지하는 경향을 보였다. 응고제 첨가온도에 따른 두부의 무게는 $75^{\circ}C$일 때 가장 많은 두부가 제조되었으며 $65^{\circ}C$의 낮은 온도나, $85^{\circ}C$의 높은 온도에서는 무게가 감소하는 경향을 나타내었다. 수분함량 역시 $75^{\circ}C$에서 가장 높은 수분함량을 나타내었고 낮은 온도와 높은 온도에서는 비교적 수분함량이 감소하는 경향을 보였다. 두부의 저장성은 실온과 $4^{\circ}C$ 모두 저장시간이 경과할수록 colony 수가 증가하였다.

4종류 목향류(木香類)의 외부(外部) 및 내부형태(內部形態)와 이화학패턴연구 (A Study on external and internal morphology and pattern analysis in 4 kinds of Mok-Hyaeng Radix)

  • 김홍준;강경식;최고야;김호경;정승일;주영승
    • 한국한의학연구원논문집
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    • 제12권3호통권18호
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    • pp.117-130
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    • 2006
  • The purpose of this study was to introduce the differential standard of Mok-Hyaeng Radix species. We established the classificatory standard according to the external and internal morphology and the pattern in 4 kinds of Mok-Hyaeng Radix. The results follow: 1. On the external morphology, Radix of Vladimiria souliei had a sticky material in the head of roots and it was yellowish white in the cut surface. It attached to teeth during chewing. Radix of Aucklandia lappa (=Saussurea lappa) was dark grayish brown and was grayish brown in the cut surface. It had special odor and was not attache to teeth chewing it. On the other hand, Radix of Inula helenium was dark brown. In the cut surface, cortical layer was different from wood layer. Radix of Aristolochia contorta was yellowish brown. In the cut surface, it was not smooth and cortical layer was different from wood layer. 2. On the internal morphology, Radix of Vladimiria souliei had many fascicular fibers and scattered large oil chambers in the bast ray, xylem ray, and parenchyma. On Radix of Aucklandia lappa (=Saussurea lappa), it was difficult to find out the trace when the cork layer was exfoliated. The cambium formed circle and the large oil chambers were scattered in the phloem and xylem. On the other hand, external cortical layer of Radix of Inula helenium was detached and cambium was formed to indistinct circle and large oil chambers were scattered in the phloem and xylem. On Radix of Arustolochia contorta, the large oil chambers were scattered in the surface later, bast part was relatively broad and cambium formed circle. 3. On the TLC pattern, Radix of Aristolochia contorta, Inula helenium, Aucklandia lappa, and Vladimiria souliei were chromogenic to violet and purple according to sulfuric acid colour pattern, especially faint on Aristolochia contorta. 4. On the pattern analysis of HPLC, we compared the content and the pattern of constunolide and dehydrocostus lactone, Radix of Aucklandia lappa was similar to Radix of Vladimiria souliei and Radix of Aristolochia contorta was similar to Radix of Inula helenium. On the total HPLC component pattern, constunolide and dehydrocostus lactone were similar in all four types, but it showed the Rf 5-6 peak was only in Radix of Aristolochia contorta, not in Radix of Inula helenium, Aucklandia lappa, and Vladimiria souliei. It is considered the results of this study will be furnished the basis to succeeding studies and it is needed to extensive comparative study for the same genus-degree of relatedness.

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Elucidation of the Biosynthetic Pathway of Vitamin B Groups and Potential Secondary Metabolite Gene Clusters Via Genome Analysis of a Marine Bacterium Pseudoruegeria sp. M32A2M

  • Cho, Sang-Hyeok;Lee, Eunju;Ko, So-Ra;Jin, Sangrak;Song, Yoseb;Ahn, Chi-Yong;Oh, Hee-Mock;Cho, Byung-Kwan;Cho, Suhyung
    • Journal of Microbiology and Biotechnology
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    • 제30권4호
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    • pp.505-514
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    • 2020
  • The symbiotic nature of the relationship between algae and marine bacteria is well-studied among the complex microbial interactions. The mutual profit between algae and bacteria occurs via nutrient and vitamin exchange. It is necessary to analyze the genome sequence of a bacterium to predict its symbiotic relationships. In this study, the genome of a marine bacterium, Pseudoruegeria sp. M32A2M, isolated from the south-eastern isles (GeoJe-Do) of South Korea, was sequenced and analyzed. A draft genome (91 scaffolds) of 5.5 Mb with a DNA G+C content of 62.4% was obtained. In total, 5,101 features were identified from gene annotation, and 4,927 genes were assigned to functional proteins. We also identified transcription core proteins, RNA polymerase subunits, and sigma factors. In addition, full flagella-related gene clusters involving the flagellar body, motor, regulator, and other accessory compartments were detected even though the genus Pseudoruegeria is known to comprise non-motile bacteria. Examination of annotated KEGG pathways revealed that Pseudoruegeria sp. M32A2M has the metabolic pathways for all seven vitamin Bs, including thiamin (vitamin B1), biotin (vitamin B7), and cobalamin (vitamin B12), which are necessary for symbiosis with vitamin B auxotroph algae. We also identified gene clusters for seven secondary metabolites including ectoine, homoserine lactone, beta-lactone, terpene, lasso peptide, bacteriocin, and non-ribosomal proteins.