• Title/Summary/Keyword: inhibitory compounds

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Various Bioactivities of Two Polyphenolic Compounds from the Brown Alga Grateoupia elliptica

  • Kim, Eun-Sook;Kim, Chan-Sook;Lee, Bong-Ho;Choi, Byoung-Wook;Ryu, Geon-Seek
    • Proceedings of the PSK Conference
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    • 2003.10b
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    • pp.190.2-190.2
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    • 2003
  • In the course of search for various bioactive compounds from marine algae, we found strong antioxidant activity of the methanolic extract of the brown alga G. elliptica. Chromatographic purification [ODS flash, gel-filtration on Sephadex LH-20, HPLC] of the BuOH layer of the methanolic extract afforded two known polyphenolic compounds, 6,6'-bieckol (1) and dieckol (2). Compound 1 showed acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitory activities, free radical scavenging activity on DPPH (1,1-diphenyl-2-picryl-hydazyl) with IC$\_$50/ values of 91.2, 45.6 and 15.5 $\mu\textrm{g}$/$m\ell$, respectively. (omitted)

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A Cipadesin Limonoid and a Tirucallane Triterpene from the Fruit of Sandoricum koetjape and their Inhibitory Properties against Receptor Tyrosine Kinases

  • Rachmadhaningtiyas, Dyah Ayu;Heliawati, Leny;Hermawati, Elvira;Syah, Yana Maolana
    • Natural Product Sciences
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    • v.27 no.2
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    • pp.134-139
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    • 2021
  • A new cipadesin limonoid, i.e. 3-epi-cipadonoid C (1), and a new tirucallane triterpene, i.e. hispidol B 3-palmitate (3), have been isolated from the seeds and fruit peels extract of Sandoricum koetjape, respectively. Along with these compounds the known limonoid, cipaferen G (2), and two pentacyclic triterpenes, bryonolic (4) and bryononic (5) acids, were also isolated. The strucrures of the new compounds were elucidated by the analysis of NMR and mass spectral data. Compounds 1 - 5 were evaluated as the inhibitor of receptor tyrosine kinases (EGFR, Epidermal Growth Factor Receptor; HER2, HER4, Human Epidermal growth factor Receptor 2, -4; IGFR, Insulin-like Growth Factor Receptor; InsR, Insulin Receptor; KDR, Kinase insert Domain Receptor; PDGFRα, and PDGFRβ, Platelet-Derived Growth Factor Receptor-α and -β). The results showed only 1 and 3 that have weak activity against InsR.

Meliasendanins E-J, Nor-neolignan Constituents from Melia toosendan and their Anti-inflammatory Activity

  • Jin Woo Lee
    • Natural Product Sciences
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    • v.29 no.1
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    • pp.17-23
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    • 2023
  • A phytochemical investigation of the fruits extract of Melia toosendan afforded the isolation of two new nor-neolignans, meliasendanins E (1) and F (2), as well as twelve known compounds (3 - 14) using various separation technique such as Diaion HP20, silica, RP-18 gel column chromatography and semi-preparative HPLC. Their chemical structures were elucidated by extensive NMR spectroscopic data including 2D-NMR, and HR-ESI-MS as well as ECD data. Among the twelve known compounds, the absolute structures of 3 - 6 were determined first, and given the trivial names as meliasendanins G-J (3 - 6). Based on the evaluation of anti-inflammatory activity, compounds 7 - 8 exhibited inhibitory effects on LPS-induced nitric oxide production in RAW 264.7 macrophages with IC50 values of 34.6 and 39.5 µM, respectively.

Phenolic compounds from the flowers of Cosmos bipinnatus and their anti-atopic activity (코스모스(Cosmos bipinnatus) 꽃으로부터 phenolic 화합물의 분리 동정과 항아토피 효과)

  • Jeon, Hyeong-Ju;Kim, Hyoung-Geun
    • Journal of Applied Biological Chemistry
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    • v.65 no.3
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    • pp.215-219
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    • 2022
  • The flowers of Cosmos bipinnatus were extracted with solvent made with methanol:water (4:1) and the concentrates were partitioned into ethyl acetate (EtOAc), n-butanol (n-BuOH), and water (H2O) fractions. The octadecyl silica gel (ODS) and silica gel (SiO2) column chromatographies were repeated for the EtOAc fraction to isolated of two phenolic compounds. The chemical structure of the isolated compounds were identified as benzyl O-β-ᴅ-glucopyranoside (1), and 2-phenylethyl O-β-ᴅ-glucopyranoside (2) through spectroscopic datas such as nuclear magnetic resornance, infrarad spectroscopy, and mass spectroscopy. These two compounds were first isolated from C. bipinnatus flowers through this study. To evaluate the anti-atopic activity of the two isolated compounds using a HaCaT cell line induced by ultraviolet light, several experiments were conducted and neither both compounds showed toxicity in the concentration range of 1 to 1,000 ㎍/mL. In the results of anti-atopic activity through Thymus and activation regualted chemokine (TARC) assay, both compounds showed dose-dependent TARC inhibitory activity. In particular, compound 1 showed significant activity even in a low concentration range of 10 ㎍/mL, and in different concentration ranges. Also compound 1 showed higher inhibitory activity than other compound, confirming that the anti-atopic activity was the most excellent. Based on these results, it is considered that it can be used as a functional cosmetic material.

Antimicrobial and Antioxidative Effects of Isoflavonoids on Skin Microbial Inflammation Pathogens (Isoflavonoid의 피부염증균에 대한 항균 및 항산화효과)

  • Shin, Jung-Mi;Yu, Hung-Won;Lee, Hyun-Ok;Lee, Mi-Hee;Baek, Seung-Hwa
    • YAKHAK HOEJI
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    • v.50 no.1
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    • pp.15-20
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    • 2006
  • Puerarin and daidzin have been isolated from Puerariae thunbergiana Benth. Structures were determined by spectroscopic methods. Compounds showed weak antimicrobial activity against S. mutans, S. epidermidis, S. aureus, and C. albicans (MIC, $800{\mu}g/ml$). However, these compounds were not antioxidative. Puerariae thunbergiana Benth. extracts against microorganisms were evaluated in terms of the minimum inhibitory concentrations (MIC). In general, C. albicans was stronger antimicrobial activity than the other microorganisms. The antioxidative activity of was observed in the etyl acetate extract ($IC_{50},\;119.87{\pm}0.16\;{\mu}g/ml$). The DPPH radical scavenging effect ($IC_{50},\;1,673.3{\pm}0.54\;{\mu}M$) of the puerarin was comparable with that of synthetic antioxidant, BHA $(IC_{50},\;88.39{\pm}1.1){\times}10^{3}{\mu}M$. These results suggest that puerarin and daidzin have a potential antimicrobial activity.

Constituents of Cynanchum auriculatum and their Inhibitory Effect on Melanogenesis in B16 Mouse Melanoma Cell Lines (이엽우피소의 성분 및 멜라닌 생성 억제활성)

  • Choi, Hyun-Gyu;Jiang, Yanfu;Roh, Eun-Mi-Ri;Kim, Young-Soo;Xu, Guang-Hua;Na, Min-Kyun;Lee, Seung-Ho
    • Korean Journal of Pharmacognosy
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    • v.41 no.4
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    • pp.238-244
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    • 2010
  • Fourteen compounds were isolated from the roots of Cynanchum auriculatum and their chemical structures were identified as ${\beta}$-sitosterol (1), acetovanillone (2), p-hydroxyacetophenone (3), 2,4-dihydroxyacetophenone (4), 2,5-dihydroxyacetophenone (5), cynandione A (6), methyleugenol (7), daucosterol (8), Succinic acid (9), cynauriculoside A (10), wilfoside C3N (11), wilfoside C1N (12), wilfoside K1N (13) and wilfoside C1G (14). Among them, compounds 2-5 were isolated from this plant for the first time. And 2, 5-dihydroxyacetophenone (5) showed the most potent inhibitory effect on melanogenesis in B-16 mouse melanoma cell lines with $IC_{50}$ value of $20\;{\mu}M$.

Isolation of Melanogenesis Inhibitors from Cinnamomi Cortex (계피로부터 멜라닌 생성 억제 성분의 분리)

  • Jung, Hee-Wook;Choi, Ji-Young;Lee, Jong-Gu;Choi, Eun-Hyang;Oh, Joon-Seok;Kim, Dong-Chun;Kim, Jeong-Ah;Park, Seong-Hee;Son, Jong-Keun;Lee, Seung-Ho
    • Korean Journal of Pharmacognosy
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    • v.38 no.4
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    • pp.382-386
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    • 2007
  • Cinnamomi Cortex (Lauraceae), the dried bark of Cinnamomum cassia BLUME, has been used as traditional Chinese medicine for its stomachic, astringent, carminative, antispasmodic, antibacterial, antifungal properties. Four compounds were isolated from the MeOH extract of Cinnamomi Cortex, and their structures were identified as trans-cinnamic acid (1), ${\beta}-sitosterol$ (2), bis(2-methylheptyl)phthalate (3), coumarin (4) by comparison of their physical and spectral data with those reported in the literature. These compounds were tested melanogenesis inhibitory effect on B-16 mouse melanoma cell lines. Among them, trans-cinnamic acid (1) showed the most potent inhibitory effect on melanogenesis with $IC_{50}$ value of $13{\mu}g/ml$. Arbutin, positive control, exhibited an $IC_{50}$ value of $29{\mu}g/ml$.

Isolation of Melanin Biosynthesis Inhibitory Compounds from the Roots of Asarum sieboldii (세신으로부터 멜라닌 생성 억제 성분의 분리)

  • Choi, Eun-Hyang;Choi, Ji-Young;Lee, Jong-Gu;Oh, Joon-Seok;Kim, Dong-Chun;Lee, Hee-Sang;Son, Jong-Keun;Son, Ae-Ryang;Kim, Jeong-Ah;Lee, Seung-Ho
    • Korean Journal of Pharmacognosy
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    • v.38 no.4
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    • pp.394-399
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    • 2007
  • Eight compounds were isolated from the roots of Asarum sieboldii and their structures were identified as $({\pm})$-car-3-ene-2,5-dione (1), (-)-asarinin (2), (-)-sesamin (3), eucarvone (4), methyleugenol (5), ${\gamma}-asarone$ (6), pellitorine (7) and asarinol A (8) by analysis of spectral data. Among them, (-)-asarinin (2) showed the most potent inhibitory effect on melanogenesis, with inhibition rate of 66%.

$^{31}p$ Nuclear Magnetic Resonance Studies of Acetic Acid Inhibition of Ethanol Production by Strains of Zymomonas mobilis

  • Kim, In-Seop;Barrow, Kevin D.;Rogers, Peter L.
    • Journal of Microbiology and Biotechnology
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    • v.13 no.1
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    • pp.90-98
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    • 2003
  • In vivo $^31p$ Nuclear Magnetic Resonance ($^31p$NMR) and metabolic studies were carried out on an acetic acid tolerant mutant, Zymomonas mobilis $ZM4/Ac^R$, and compared to those of the parent strain, Z. mobilis ZM4, to evaluate possible mechanisms of acetic acid resistance. This investigation was initiated to determine whether or not the mutant strain might be used as a suitable recombinant host far ethanol production from lignocellulose hydrolysates containing various inhibitory compounds. $ZM4/Ac^R$ showed multiple resistance to other lignocellulosic toxic compounds such as syringaldehyde, furfural, hydroxymethyl furfural, vanillin, and vanillic acid. The mutant strain was resistant to higher concentrations of ethanol or lower pH in the presence of sodium acetate, compared to ZM4 which showed more additive inhibition. in vivo $^31p$ NMR studies revealed that intracellular acidification and de-energization were two mechanisms by which acetic acid exerted its inhibitory effect. For $ZM4/Ac^R$, the internal pH and the energy status were less affected by sodium acetate compared to the parent strain. This resistance to pH change and de-energization caused by acetic acid is a possible explanation for the development of resistance by this strain.

Melanin Biosynthesis Inhibitory Activities of Coumarins Isolated from Angelica polymorpha MAXIM (궁궁이(Angelica polymorpha MAXIM)로부터 분리한 Coumarin 계열 화합물의 Melanin 생합성 억제 활성)

  • 이충환;백승화;김진희;김현아;이상명;이찬용;고영희
    • Microbiology and Biotechnology Letters
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    • v.31 no.2
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    • pp.135-139
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    • 2003
  • During the screening for inhibitors of melanin biosynthesis from plant extract, Angelica polymorpha MAXIM which showed a high level of inhibition was selected. The inhibiting substances were purified form methanol extract of Angelica polymorpha MAXIM followed by silica gel column chromatography and HPLC. The inhibitors were identified as heraclenin, isosaxalin and heraclenol 3'-Me ether, by spectrescopic methods of ESI-MS, H-NMR, C-NMR, DEPT, HMQC and HMBC. These compounds did not have mushroom tyrosinase inhibitory activity, but showed a highly potent melanin biosynthesis inhibition zone in the plate culture of Streptomyces bikiniensis, a bacterium used as an indicator organism in this work. These compounds did not show any growth inhibition against S. bikiniensis at the same concentration of melanin biosynthesis test.