• YAKHAK HOEJI
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• v.41 no.5
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• pp.554-558
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• 1997

Two alkaloidal components were isolated from the ether soluble part of the MeOH extract of the root bark of Euonymus japonica. Their structures were elucidated by the spe ctroscopic analylses as the sesquiterpene pyridine alkaloids derived from polyester sesquiterpenes which are characteristically detected in Celastraceae plants. These include macrocycle formed by two ester linkages between dihydro-${\beta}$-agarofuran nucleus and pyridinic dibasic acid(compound 1:evoninic acid, compound 2:wilfordic acid). The structure of compound $1[C_{47}H_{50}N_2O_{17},\;mp\;161{\sim}163^{circ}C$. $[{\alpha}]_D^{28}=+31.6^{\circ}$(c, 0.1 in EtOH)] was determined as novel structure named as euojaponine N, and compound $2[C_{48}H_{57}NO_{18},\;mp\;142{\sim}145^{circ}C,\;[{\alpha}_D^{27}=+27.0^{\circ}$(c, 0.1 in EtOH)] was identified as ebenifoline W-I reported from Maytenus ebenifolia.

• The Korean Journal of Physiology and Pharmacology
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• v.17 no.3
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• pp.217-222
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• 2013

We reported that ailanthoidol, a neolignan from Zanthoxylum ailanthoides and Salvia miltiorrhiza Bunge, inhibited inflammatory reactions by macrophages and protected mice from endotoxin shock. We examined the anti-inflammatory activity of six synthetic ailanthoidol derivatives (compounds 1-6). Among them, compound 4, 2-(4-hydroxyphenyl)-5-(3-hydroxypropenyl)-7-methoxybenzofuran, had the lowest $IC_{50}$ value concerning nitric oxide (NO) release from lipopolysaccharide (LPS)-stimulated RAW264.7 cells. Compound 4 suppressed the generation of prostaglandin (PG) $E_2$ and the expression of inducible NO synthase and cyclooxygenase (COX)-2 induced by LPS, and inhibited the release of LPS-induced pro-inflammatory cytokines from RAW264.7 cells. The underlying mechanism of compound 4 on anti-inflammatory action was correlated with the down-regulation of mitogen-activated protein kinase and activator protein-1 activation. Compound 4 is potentially an effective functional chemical candidate for the prevention of inflammatory diseases.

• Journal of the Korean Chemical Society
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• v.57 no.6
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• pp.755-760
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• 2013

The present study is synthesis of derivatives of N'-(4-amino-5-sulfanyl-4H-1,2,4-triazole-3-yl)-2-(1H-benzimidazole-2-ylsulfanyl) acetohydrazide (IV). Antibacterial activity tested against the E. coli and A. Substilis. Biological activities conducted by disc diffusion method. Compound $2MB_1$, $2MB_3$, $2MB_5$ inhibit the appreciable microbial growth while rest of the compound possess the moderate activities. Anti-inflammatory activity tested by reduces local edema induced in the rat paw by injection of phlogestic agent. Compound $2MB_1$, $2MB_8$, $2MB_5$, $2MB_3$ and $2MB_6$ exhibit satisfying anti-inflammatory activity while analgesic activity conducted by acetic acid induced writhing effect in mice while compound $2MB_1$, $2MB_4$ and $2MB_7$ having the good analgesic activity. The chemical structures of all newly synthesized compounds were confirmed by their IR, $^1H$ NMR and mass spectral data.

• Journal of Microbiology and Biotechnology
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• v.33 no.7
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• pp.941-948
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• 2023

Metabolites from medicinal plants continue to hold significant value in the exploration and advancement of novel pharmaceuticals. In the search for plants containing compounds with anti-inflammatory effects, we observed that the ethanol (EtOH) extract obtained from the aerial components of Gouania leptostachya DC. var. tonkinensis Pit. exhibited substantial suppression of nitric oxide (NO) in vitro. In a phytochemical study on an EtOH extract of G. leptostachya, 11 compounds were purified, including one unreported compound namely gouanioside A (1). Their chemical structures were unambiguously determined through the use of various spectroscopic techniques, such as 1 and 2D NMR, IR, and HR-ESI-MS, and by producing derivatives via chemical reactions. The EtOH extract, fractions, and a new compound exerted inflammatory effects by altering NO synthesis in murine RAW264.7 macrophage cells stimulated with lipopolysaccharide. The underlying inflammatory mechanism of the new compound 1 was also explored through various in vitro experiments. The results of this study indicate the potential usefulness of new compound 1 from G. leptostachya as a treatment for inflammatory diseases.

• Bulletin of the Korean Chemical Society
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• v.33 no.11
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• pp.3571-3575
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• 2012

A number of novel small molecules, safrole oxide derivatives 4a-c, 6a-c, 9a-h, were synthesized by the reaction of safrole oxide with anilines 3 and 5, or its alkyl allyl ether derivative 7 with alkyl bromide 8 in moderate yields. The antiproliferative effects of all the target molecules on A549 cell growth were investigated and it was found that the 14 novel compounds could suppress A549 lung cancer cell growth. Among them, compound 6b was the most effective compound in inhibiting the proliferation of A549 cells.

• YAKHAK HOEJI
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• v.59 no.6
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• pp.266-269
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• 2015

Coccidiosis is induced by Toxoplasma gondii and Eimeria tenella and novel anticoccidial drugs have been requested. In this study, the anticoccidial effect of 3-(4-methoxybenzylaminomethylene)-1,3-dihydroindole-2-one (5-108) on T. gondii and E. tenella was evaluated. Novel synthetic derivative 5-108 showed 1.44 fold higher relative selectivity compared to pyrimethamine against T. gondii in vitro assay. In chicken study, compound 5-108 significantly decreased the number of oocytes of E. tenella in feces, obtained from E. tenella-infected chickens, by $33{\pm}2.64%$ and $23{\pm}3.60%$ (P<0.001) at $7^{th}$ day and $9^{th}$ day p.i.. Conclusively, compound 5-108 was effective against T. gondii and E. tenella.

• Bulletin of the Korean Chemical Society
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• v.34 no.8
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• pp.2297-2304
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• 2013

A series of novel benzimidazole derivatives bearing a heterocyclic ring as oxadiazole (21-32), thiadiazole (33-34), triazole (35-36) were synthesized and evaluated for their activities against Coxsackie virus B3 and B6 in Vero cells. Compounds 21-26, 31-36 with moieties of 2'-pyridyl, 3'-pyridyl and 4'-pyridyl at the 2-position and oxadiazoles, thiadiazole, or triazole substituent at the 4- or 5-position generally displayed activities against CVB3 and CVB6. Especially compound 24 ($IC_{50}=1.08{\mu}g/mL$, SI = 61.7 against CVB3) was the promising candidate as lead compound for anti-enteroviral drug. It was observed in the incorporation of heterocyclic rings in benzimidazole at the 5-position could enhance their biological activities.

• Archives of Pharmacal Research
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• v.25 no.6
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• pp.790-794
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• 2002

A series of novel exomethylene cyclopropyl nucleosides have been synthesized starting from Feist's acid. Classical nucleophilic substitution conditions ($K_2CO_3$, 18-crown-6) of the tosylate 2 as well as Mitsunobu reaction (DEAD, $PPh_3$) of alcohol 1 with pyrimidine bases afforded a series of novel cyclopropyl nucleosides. Compound 4b displayed moderate anti-HBV activity without any cytotoxicity up to $100{\;}{\mu}M$.

• Journal of the Society of Cosmetic Scientists of Korea
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• v.27 no.1
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• pp.111-118
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• 2001

A novel melanogenic inhibitory compound, Phytoclear-EL1 (5,10-diacetyl-3-benzoyllathyrol) was isolated from Euphorbiae lathyridis. The effects of EL1 on culture normal human melanocytes (NHM) were assessed. EL1 reduced the melanin synthesis of NHM by 40% at a concentration of 2 $\square$g/ml without any apparent cytotoxicity. We also have found that the treatment of the cells with EL1 decreased the tyrosinase activity by 29% in situ. To elucidate the action mechanism of EL1, we investigated the changes in mRNA levels of tyrosinase, TRP-1 and TRP-2 using RT-PCR technique. AS a result, the mRNA levels of tyrosinase, TRP-1 and TRP-2 were markedly reduced by EL1 treatment. These results suggest that Phytoclear-EL1 is a novel whitening agent that is effective in human melanocytes.

• Journal of Microbiology and Biotechnology
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• v.25 no.7
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• pp.1047-1055
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• 2015

For the search of a potent first-in-class compound to inactivate macrophages responsible for inflammatory responses, in the present study, we investigated the anti-nflammatory effects of YH-1118, a novel synthetic compound, in a lipopolysaccharide (LPS)-stimulated mouse macrophage cell line, Raw 264.7. YH-1118 inhibited LPS-induced nitric oxide (NO) production and inducible NO synthase (iNOS) expression at both the protein and mRNA levels. The suppression of LPS-induced iNOS expression by YH-1118 was mediated via nuclear factor kappa B (NF-κB), but not activator protein-1 (AP-1) transcription factor. This was supported by the finding that YH-1118 attenuated the phosphorylation of inhibitor of κBα (IκBα) and nuclear translocation and DNA binding activity of NF-κB. Through the mechanisms that YH-1118 inhibited the activation of IκB kinases (IKKs), upstream activators of NF-κB, or p38 MAPK, YH-1118 significantly suppressed LPS-induced production of pro-inflammatory cytokines, tumor necrosis factor-α, interleukin-1β (IL-1β), and IL-6 (p < 0.05). In conclusion, our results suggest that YH-1118 inhibits LPS-induced inflammatory responses by blocking IKK and NF-κB activation in macrophages, and may be a therapeutic candidate for the treatment of various inflammatory diseases.