• Title/Summary/Keyword: Hydrophobic compounds

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Gut microbiota-mediated pharmacokinetics of ginseng saponins

  • Kim, Dong-Hyun
    • Journal of Ginseng Research
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    • v.42 no.3
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    • pp.255-263
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    • 2018
  • Orally administered ginsengs come in contact with the gut microbiota, and their hydrophilic constituents, such as ginsenosides, are metabolized to hydrophobic compounds by gastric juice and gut microbiota: protopanxadiol-type ginsenosides are mainly transformed into compound K and ginsenoside Rh2; protopanaxatriol-type ginsenosides to ginsenoside Rh1 and protopanaxatriol, and ocotillol-type ginsenosides to ocotillol. Although this metabolizing activity varies between individuals, the metabolism of ginsenosides to compound K by gut microbiota in individuals treated with ginseng is proportional to the area under the blood concentration curve for compound K in their blood samples. These metabolites such as compound K exhibit potent pharmacological effects, such as antitumor, anti-inflammatory, antidiabetic, antiallergic, and neuroprotective effects compared with the parent ginsenosides, such as Rb1, Rb2, and Re. Therefore, to monitor the potent pharmacological effects of ginseng, a novel probiotic fermentation technology has been developed to produce absorbable and bioactive metabolites. Based on these findings, it is concluded that gut microbiota play an important role in the pharmacological action of orally administered ginseng, and probiotics that can replace gut microbiota can be used in the development of beneficial and bioactive ginsengs.

Molecular Docking Studies of p21-Activated Kinase-1 (PAK1) Inhibitors

  • Balupuri, Anand;Balasubramanian, Pavithra K.;Cho, Seung Joo
    • Journal of Integrative Natural Science
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    • v.9 no.3
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    • pp.161-165
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    • 2016
  • The p21-activated kinase-1 (PAK1) has emerged as a potential target for anticancer therapy. It is overexpressed in ovarian, breast and bladder cancers. This suggests that PAK1 may contribute to tumorigenesis. 4-azaindole derivatives are reported as potent PAK1 inhibitors. The present work deals with the molecular docking studies of 4-azaindoles with PAK1. Probable binding mode of these inhibitors has been identified by molecular modeling. Docking results indicated that hydrogen bonding interactions with Glu345 and Leu347 are responsible for governing inhibitor potency of the compounds. Additionally, Val284, Val328, Met344 and Leu396 were found to be accountable for hydrophobic interactions inside the active site of PAK1.

Synthesis and Cytotoxic Properties of 3,4-dihydro-3-oxo-2H-1,2,4-benzothiadiazine-1,1-dioxides (3,4-디히드로-3-옥소-2H-1,2,4-벤조치아디아진-1,1-디옥사이드 유도체의 합성 및 세포 독성)

  • 박혜영;한윤정;이정옥
    • YAKHAK HOEJI
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    • v.39 no.6
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    • pp.631-635
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    • 1995
  • A series of 3, 4-dihydro-3-oxo-2H-1, 2, 4-benzothiadiazine-1, 1, dioxides with cytotoxic activity against human solid tumors is described. Synthesized compounds showed mild but broad spectrum cytotoxicity in vitro. The lipophilic substituents like alkyl, alkoxy and chloro on benzene ring increased the activity. Also hydrophobic group on 3 or 4 position of benzothiadiazine was important for the activity.

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Suppressive Effects of Coumarins on Pumpkin Seedling Growth and Glutathione S-Transferase Activity

  • Hossain, Md. Daud;Li, Jing;Guo, Shirong;Fujita, Masayuki
    • Journal of Crop Science and Biotechnology
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    • v.11 no.3
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    • pp.187-192
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    • 2008
  • The effects of some coumarins(coumarin, 7-hydroxycoumarin, scopoletin and esculetin) were investigated on pumpkin(Cucurbita maxima Duch.) seedlings and on pumpkin glutathione S-transferases(GSTs). Coumarin and esculetin suppressed the growth of seedlings, especially the elongation of roots as well as hypocotyls. Among the compounds tested, only esculetin inhibited the activity of a particular pumpkin GST by 50%, CmGSTU3 toward 1-chloro-2, 4- dinitrobenzene(CDNB) and at a concentration of 22 ${\mu}M$. Both ethylacetae(EtOAc) and water fractions in pumpkin seedlings and different organs of one-month-old pumpkin plants contained esculetin or similar hydrophobic fluorescent substances as well as hydrophilic substances, which showed different degrees of inhibitory effects on CmGSTU3 activity.

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Absorption and Fluorescence Studies of 3-Ethenylindoles

  • Singh, Anil K.;Hota, Prasanta K.
    • Journal of Photoscience
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    • v.11 no.3
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    • pp.107-113
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    • 2004
  • Synthesis, absorption and fluorescence properties of 3-methyl indole (1), N-(benzenesulfonyl)-3-(3-oxo-but-1-enyl)-indole (2) and 1H-3-(3-oxo-but-1-enyl)-indole (3) are described. Extended conjugation at C-3 of indole as in 3 causes moderate resolution of $^1L_a$ and $^1L_b$ bands. However, 2 having an electron-withdrawing group at indolic nitrogen shows only the $^1L_a$ band. While the $^1L_b$ band largely remains solvent polarity independent, the $^1L_a$ band undergoes moderate red shift in polar solvents. The fluorescence in 2 and 3 originates from the $L_b$ transition. Additionally, interaction of 2 and 3 with BSA indicates that these compounds bind to the hydrophobic site of BSA with the formation of a highly fluorescent BSA-probe complex.

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Studies on the Gemini Type Amphipathic Surfactants(3);Synthesis of Amphipathic Compound with Two Sulfate Groups and Two Lipophilic Alkyl Chains (제미니형 양친매성 계면활성제에 관한 연구(제3보);두 개의 술폰산염과 소수성알킬기를 갖는 양친매성 화합물의 합성)

  • Yun, Y.K.;Kim, Y.Ch.;Jeong, H.K.;Nam, K.D.
    • Journal of the Korean Applied Science and Technology
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    • v.15 no.1
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    • pp.99-108
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    • 1998
  • Novel type surfactants containing two long-chain hydrophobic alkyl groups and two hydrophilic sulfonate groups were successfully synthesized by reactions of ethylene glycol diglycidyl ether with long-chain fatty alcohols, after then by reactions with 1,3-propane sultone and sodium hydride under THF solvent. All these compounds, so called Gemini surfactants, were purified by thin layer chromatography and column chromatography. Their structures were identified by FT-IR and $^{1}H$-NMR.

Bioisosterism: Interchange of 4-OH to 4-NH2 in Vanillin or Homovanillin Ring of Capsaicinoids

  • Cho, Sung-Ju;Jung, Young-Sik;Seong, Churl-Min;Park, Woo-Kyu;Kong, Jae-Yang;Park, No-Sang
    • Archives of Pharmacal Research
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    • v.22 no.2
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    • pp.184-188
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    • 1999
  • A series of 4-amino Capsaincin anallogs 15, 17 and 19 were prepared to investigate the bioisosteric effect of 4-amino group, and all these compounds exhibited moderate or weak potency from their analgesic test. From our previous results and others, 4-hydroxyl group as well as 3-methoxy substituent could be crucial for high analgesic activity. This biological results also shows that the activity is sensitive to alkyl chain length in hydrophobic region and the phenylacetic amides 19 are more active than the corresponding urea derivatives 17.

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Flavonoids as Novel Therapeutic Agents Against Chikungunya Virus Capsid Protein: A Molecular Docking Approach

  • E. Vadivel;Gundeep Ekka;J. Fermin Angelo Selvin
    • Journal of the Korean Chemical Society
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    • v.67 no.4
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    • pp.226-235
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    • 2023
  • Chikungunya fever has a high morbidity rate in humans and is caused by chikungunya virus. There are no treatments available until now for this particular viral disease. The present study was carried out by selecting 19 flavonoids, which are available naturally in fruits, vegetables, tea, red wine and medicinal plants. The molecular docking of selected 19 flavonoids was carried out against the Chikungunya virus capsid protein using the Autodock4.2 software. Binding affinity analysis based on the Intermolecular interactions such as Hydrogen bonding and hydrophobic interactions and drug-likeness properties for all the 19 flavonoids have been carried out and it is found that the top four molecules are Chrysin, Fisetin, Naringenin and Biochanin A as they fit to the chikungunya protein and have binding energy of -8.09, -8.01, -7.6, and 7.3 kcal/mol respectively. This result opens up the possibility of applying these compounds in the inhibition of chikungunya viral protein.

Synthesis of Novel Ester Quaternary Ammonium Cationic Surfactants via Michael Addition Reaction (Michael Addition Reaction을 이용한 신규 Ester Quaternary Ammonium Salt 양이온 계면활성제의 합성)

  • Kang, Eun-kyung;Jung, Seon Hwa;Jung, GaYoung;Lee, Byung Min
    • Journal of the Korean Applied Science and Technology
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    • v.34 no.1
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    • pp.142-151
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    • 2017
  • Cationic surfactants have a bactericidal effect and the study for effective development of them became important parts in the industry. There have been increasing researches that focus on the development of products having not only outstanding features but also safety and biodegradability. In this work, novel ester-type cationic surfactants were obtained via Michael addition reaction. Intermediates were quantitatively prepared by the Michael addition reaction between alkyl acrylate and amine compounds under mild conditions without solvent and catalyst. The intermediates were quaternized with dimethyl sulfate. HQ21 with two hydrophobic groups and a hydrophilic group and HQ22 with two hydrophobic groups and two hydrophilic groups were obtained. The structures of the products were characterized by 1H-NMR, HR-MS and FT-IR and biodegradability of the products were tested.

An influence on EDC/PPCPs adsorption onto single-walled carbon nanotubes with cationic surfactant (단일벽 탄소나노튜브의 미량유해물질 흡착거동에서 양이온 계면활성제의 영향에 관한 연구)

  • Heo, Jiyong;Lee, Heebum;Han, Jonghun;Son, Mihyang;Her, Namguk
    • Journal of Korean Society of Water and Wastewater
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    • v.28 no.4
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    • pp.419-429
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    • 2014
  • Recent studies have been reported the presence of Endocrine Disrupting Compounds, Pharmaceuticals and Personal Care Products (EDC/PPCPs) in surface and wastewater, which could potentially affect to the complicate behavior in coupled presence of nano-colloid particles and surfactants (adsorption, dispersion, and partitioning). In this study, the adsorption of EDC/PPCPs by Single Walled Carbon Nanotubes (SWNTs) as a representative of nano-particles in cationic surfactant solutions were investigated. Hydrophobic interactions (${\pi}-{\pi}$ Electron Donor-Acceptor) have been reported as a potential adsorption mechanisms for EDC/PPCPs onto SWNTs. Generally, the adsorptive capacity of the relatively hydrophobic EDC/PPCPs onto SWNTs decreased in the presence of cationic surfactant (Cetyltrimethyl Ammonium Bromide, CTAB). This study revealed that the competitive adsorption occurred between CTAB cations and EDC/PPCPs by occupying the available SWNT surface (CTAB adsorption onto SWNTs shows five-regime and maximum adsorption capacity of 370.4 mg/g by applying the BET isotherm). The adsorption capacity of $17{\alpha}$-ethinyl estradiol (EE2) on SWNT showed the decrease of 48% in the presence of CTAB. However, the adsorbed naproxen (NAP) surely increased by forming hemimicelles and resulted in a favorable media formation for NAP partition to increase SWNTs adsorption capacity. The adsorbed NAP increased from 24 to 82.9 mg/g after the interaction of CTAB with NAP. The competitive adsorption for EDC/PPCPs onto SWNTs is likely to be a key factor in the presence of cationic surfactant, however, NAP adsorption showed a slight competition through $CH_3-CH_3$ interaction by forming hemimicelles on SWNT surface.