• Title/Summary/Keyword: sub-compounds

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Cytotoxic compounds against adenocarcinoma alveolar epithelial A549 cells from Paeoniae Radix (작약 뿌리에서 분리한 폐포 선암 세포주 A549에 대한 세포독성 화합물)

  • Ji Won Park;Sang-Eun Shin;Haewon Park;Jeong Ah Kim;Eun-Ju Yang;Kyung-Sik Song
    • Journal of Applied Biological Chemistry
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    • v.66
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    • pp.272-281
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    • 2023
  • It has been known that Paeoniae Radix (PR) contains monoterpene glycosides showing a variety of biological activities such as anti-spasmodic, anti-inflammatory, anti-viral, neuroprotective, and sedative effects. This study aimed to find the cytotoxic compounds isolated from the dichloromethane (CH2Cl2)- and ethyl acetate-soluble fractions of PR. As results, thirteen compounds (1-13) were isolated and the chemical structures were identified. In addition, the human alveolar adenocarcinoma cell line (A549) was treated with isolated compounds to determine the cytotoxic effect via evaluation of cell viability. The reduction of A549 cell viability was shown as following order; gallic acid (8) > (2S)-naringenin (9) > methyl gallate (10)>6'-O-benzoylpaeoniflorin (7) > palmitic acid (3). Especially, 7 did not show the cytotoxicity in the human lung fibroblast cell line (MRC-5). The effect of 7 on the cell viabilities in A549 and MRC-5 is firstly reported in this study. Further study is required to find out the cytotoxic mechanism and the selectivity for the cancer cells of 7 in detail.

Gas Phase Proton Affinity, Basicity, and pKa Values for Nitrogen Containing Heterocyclic Aromatic Compounds

  • Hwang, Sun-Gu;Jang, Yun-Hee;Chung, Doo-Soo
    • Bulletin of the Korean Chemical Society
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    • v.26 no.4
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    • pp.585-588
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    • 2005
  • Bipyridine and its derivatives have been widely used as the ligands in transition metal complexes. The proton affinities of pyridine derivatives were calculated using an ab initio quantum mechanical method (B3LYP with various double zeta and triple zeta basis sets) in combination with the Poisson-Boltzmann continuum solvation model. Van der Waals radii of the atoms in the heterocyclic rings for the solvation energy calculation were set to values determined to reproduce the $pK_a$ values of guanine and oxoguanine derivatives and that of chlorine was optimized to reproduce the experimental values of relating compounds. The $pK_a$ values for the heterocyclic ring compounds were in agreement with the experimental values with a mean unsigned error of 0.45 $pK_a$ units.

Two New Caffeoyl Threonate Esters from the Leaves of Toxicodendron vernicifluum

  • Jang, Jae Young;Ahn, Jong Hoon;Jo, Yang Hee;Turk, Ayman;Kang, So Young;Hwang, Bang Yeon;Lee, Mi Kyeong
    • Natural Product Sciences
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    • v.25 no.4
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    • pp.354-357
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    • 2019
  • Toxicodendron vernicifluum, also called as Rhus verniciflua is a deciduous tree belonging to Anacardiaceae family. Two new caffeoyl threonate esters, rhuseols A (1) and B (2), together with 5-O-(E)-caffeoylquinic acid methyl ester (3) were isolated from the leaves of T. vernicifluum. The structures of isolated compounds were established by using 1D and 2D NMR in combination with HR-ESI-MS. Compounds 1 - 3 showed DPPH radical scavenging effects with IC50 values of 47.9, 107.8 and 15.4 μM, respectively. Taken together, these compounds might contribute to the antioxidant properties of the leaves of T. vernicifluum, which will be useful for various oxidative stress mediated diseases.

Novel Sesquiterpenoid Compounds from Culture Broth of Stereum hirsutum

  • Cho, Yang-Rae;Yun, Bong-Sik;Lee, In-Kyoung;Lee, Tae-Ho;Yoo, Ick-Dong
    • Proceedings of the Korean Society of Applied Pharmacology
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    • 1998.11a
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    • pp.130-130
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    • 1998
  • Two novel compounds SSC1 and SSC2 were isolated from culture broth produced from the strain of Stereum hirsutum by using of YM broth. They were isolated through HP-20 column chromatography, silica gel column chromatography and preparative HPLC, successively. The molecular formulas of SSC1 and SSC2. were determined as C$\sub$15/H$\sub$22/O$_3$ by high resolution EI -mass. The chemical structures of SSC1 and SSC2 were determined as sesquiterpenoid compounds by spectroscopic analysis of UV, IR, $^1$H NMR, $\^$13/C NMR, DEPT, HMQC and HMBC spectrum.

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Scalarane-type Sesterterpenes from the Philippines Sponge Hyrtios sp.

  • Choi, Jae-Hyeong;Lee, Hyi-Seung;Campos, Wilfredo L.
    • Ocean and Polar Research
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    • v.42 no.1
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    • pp.15-20
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    • 2020
  • The marine sponge Hyrtios sp. collected in the Philippines was extracted and partitioned. The resulting organic layer was purified by C18 reversed-phase column chromatography and HPLC to achieve the separation of nine scalarane-type sesterterpenes, including one new compound with eight known scalarane analogs. The chemical structures of the isolated compounds 1-9 were elucidated by 1D and 2D NMR and MS data analysis. All nine compounds were evaluated for their antibacterial activities against three Gram-positive and three Gram-negative bacteria. The compound 3 exhibited potent antibacterial activities against Bacillus subtilis and Micrococcus luteus. The compounds 7 and 9 displayed considerable activities against Bacillus subtilis and the others had moderate results.

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.

Anti-thrombotic effects of ginsenoside Rk3 by regulating cAMP and PI3K/MAPK pathway on human platelets

  • Hyuk-Woo Kwon ;Jung-Hae Shin ;Man Hee Rhee ;Chang-Eun Park ;Dong-Ha Lee
    • Journal of Ginseng Research
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    • v.47 no.6
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    • pp.706-713
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    • 2023
  • Background and objective: The ability to inhibit aggregation has been demonstrated with synthetically derived ginsenoside compounds G-Rp (1, 3, and 4) and ginsenosides naturally found in Panax ginseng 20(S)-Rg3, Rg6, F4, and Ro. Among these compounds, Rk3 (G-Rk3) from Panax ginseng needs to be further explored in order to reveal the mechanisms of action during inhibition. Methodology: Our study focused to investigate the action of G-Rk3 on agonist-stimulated human platelet aggregation, inhibition of platelet signaling molecules such as fibrinogen binding with integrin αIIbβ3 using flow cytometry, intracellular calcium mobilization, dense granule secretion, and thromboxane B2 secretion. In addition, we checked the regulation of phosphorylation on PI3K/MAPK pathway, and thrombin-induced clot retraction was also observed in platelets rich plasma. Key Results: G-Rk3 significantly increased amounts of cyclic adenosine monophosphate (cAMP) and led to significant phosphorylation of cAMP-dependent kinase substrates vasodilator-stimulated phosphoprotein (VASP) and inositol 1,4,5-trisphosphate receptor (IP3R). In the presence of G-Rk3, dense tubular system Ca2+ was inhibited, and platelet activity was lowered by inactivating the integrin αIIb/β3 and reducing the binding of fibrinogen. Furthermore, the effect of G-Rk3 extended to the inhibition of MAPK and PI3K/Akt phosphorylation resulting in the reduced secretion of intracellular granules and reduced production of TXA2. Lastly, G-Rk3 inhibited platelet aggregation and thrombus formation via fibrin clot. Conclusions and implications: These results suggest that when dealing with cardiovascular diseases brought upon by faulty aggregation among platelets or through the formation of a thrombus, the G-Rk3 compound can play a role as an effective prophylactic or therapeutic agent.

The effects of Hemistepta lyrata Bunge (Bunge) fractionated extract on liver X receptor α-dependent lipogenic genes in hepatocyte-derived cells (간 실질세포주에서 니호채(泥胡菜) 분획물이 liver X receptor α 의존적 지방 생성 유전자의 발현에 미치는 효과)

  • Kim, Jae Kwang;Cho, Il Je;Kim, Eun Ok;Jung, Dae Hwa;Ku, Sae Kwang;Kim, Sang Chan
    • Herbal Formula Science
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    • v.28 no.3
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    • pp.255-269
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    • 2020
  • Objectives : Hemistepta lyrata Bunge (Bunge) is a wild herb that has been used for managing fever and wound in Korean Traditional Medicine. The present study explored the effects of H. lyrata extract on liver X receptor (LXR) α-dependent lipogenic genes in hepatocyte-derived cells. Methods : After HepG2 cells or Huh7 cells were pre-treated with 1-10 ㎍/mL of H. lyrata extract or its fractionated extract for 0.5 h, the cells were subsequently exposed to LXR ligand for 6-24 h. Cell viability, LXR response element (LXRE)-driven luciferase activity, sterol regulatory element binding protein-response element (SREBP-RE)-driven luciferase activity, SREBP-1c expression, and mRNA levels of LXRα and its-dependent target genes were determined. In addition, LC-MS/MS analysis was conducted to explore major compounds in H. lyrata-chloroform fractionated extract #4 (HL-CF4). Results : Of various H. lyrata extracts tested, chloroform extract and its fractionated extract #4, HL-CF4, significantly decreased T0901317-mediated SREBP-1c expression. In addition, HL-CF4 significantly reduced LXRE atransactivation and LXRα mRNA expression without any cytotoxicity. Moreover, HL-CF4 prevented the SREBP-RE-driven luciferase activity and mRNA levels of fatty acid synthase and stearoyl-CoA desaturase-1 induced by T0901317. Results from LC-MS/MS analysis at positive/negative mode indicated that HL-CF4 contained several compounds showing m/z 197.1176 (C11H17O3), 693.2913/227.1069 (C38H45O12/C15H15O2), 203.1797 (C15H23), 181.1225 (C11H17O2), 591.2957 (C35H43O8), 379.1040 (C18H19O9), 409.1509 (C20H25O9), 309.1348 (C16H21O6), 391.1404 (C20H23O8), and 669.2924/389.1248 (C36H45O12/C20H21O8). Conclusion : Based on its inhibition of the LXRα-dependent signaling pathway, H. lyrata chloroform extract and HL-CF4 have prophylactic potentials for managing non-alcoholic fatty liver.

Quantitative Analytical Method for Eighteen Marker Compounds in Ongyeong-tang, a Traditional Herbal Formula, Using High-Performance Liquid Chromatography for Quality Assessment

  • Kim, Jung-Hoon;Shin, Hyeun-Kyoo;Seo, Chang-Seob
    • The Korea Journal of Herbology
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    • v.30 no.4
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    • pp.11-20
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    • 2015
  • Objectives : Ongyeong-tang (OGT) is a traditional herbal formula used to cure gynaecological disorders. OGT consists of 12 herbal medicines containing various bioactive components. Therefore, the development of suitable analytical method for the marker compounds is necessary for the quality control of OGT. Methods : Determination of the 18 marker compounds in OGT preparations was quantitatively performed by high-performance liquid chromatography-photodiode array detection analysis. The marker compounds were separated on a reversed-phase C 18 column and the analytical method was successfully validated, which was applied to compare OGT extracts from laboratory preparation and commercial OGT granules. Results : Limit of detection and limit of quantification values were in the ranges of $0.001-0.016{\mu}g/mL$ and $0.003-0.047{\mu}g/mL$, respectively. Precision was 0.03-3.71 % within a day and 0.03-3.81 % over four consecutive days. Recovery of marker compounds ranged from 90.63-108.26 %, with relative standard deviation (RSD) values < 4.0 %. Reproducibility was < 2.5 % of the RSD value. The 18 marker compounds were stable within 16 h at $10^{\circ}C$, with the RSD value < 3.5 %. Quantitative analysis results showed that the quantities of the 18 marker compounds varied among OGT samples. Pearson coefficient evaluation and principal component analysis demonstrated that an OGT water extract produced by a laboratory method clearly differed from commercial OGT granules. Conclusions : The developed analytical method was simple, precise, and reliable. Therefore, it can be used for the quality assessment of OGT preparations.

Analysis on Optical Properties of Transition-metal Substituted Ferromagnetic T0.2Fe2.8O4 (T = V, Cr, Mn) Compounds (전이금속 원소가 치환된 준강자성체 T0.2Fe2.8O4(T = V, Cr, Mn) 화합물의 광학적 성질 분석)

  • Kim, Kwang-Joo
    • Journal of the Korean Magnetics Society
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    • v.21 no.2
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    • pp.56-60
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    • 2011
  • Optical properties of $T_{0.2}Fe_{2.8}O_4$ (T = V, Cr, Mn) thin films derived from ferrimagnetic $Fe_3O_4$ were investigated by spectroscopic ellipsometry in the 1~8 eV photon-energy range. The difference in optical-absorption spectrum between the ternary compounds and $Fe_3O_4$ was analyzed based on preferable sites in spinel structure and iconicity of the doped V, Cr, and Mn ions. The observed absorption spectra from $Fe_3O_4$ and the ternary compounds can be interpreted as mainly due to charge-transfer transitions of Fe d electrons characterized by absorption structures with wide energy width. Also, the observed absorption structures with narrow energy width can be interpreted as due to crystal-field transitions between different d electron configurations of tetrahedral $Fe^{3+}(d^5)$ ion. The transitions were described in terms of spin-polarized electronic states of $Fe_3O_4$.