• Natural Product Sciences
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• v.26 no.4
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• pp.345-350
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• 2020

In recent years, tyrosine kinases (TKs) have been the target to combat cancers, and most of the developed inhibitors are of synthetic origin. Natural compounds that have the properties as the TK's inhibitors are very limited. This paper described the isolation of a new dammarane triterpene from the tree bark of Sandoricum koetjape, along with three known related dammaranes from the damar resin of Shorea javanica, as well as their inhibitory properties against eight receptor TKs (RTKs: EGFR, HER2, HER4, IGF1R, InsR, KDR, PDGFRα, and PDGFRβ). Based on the NMR and mass spectral data the new compound was identified as (12β,20S)-12,20-dihydroxy-3,4-seco-dammaran-4,24-dien-3-oic acid (12β-hydroxydammarenolic acid) (1), while the three known compounds were identified as (20S)-20-hydroxy-3,4-seco-dammaran-4,24-dien-3-oic acid (dammarenolic acid) (2), (3β,20S)-3,20-dihydroxydammaran-24-ene (3), and (20S)-3-oxo-20-hydroxydammaran-24-ene (4). The tyrosine kinase assay of the four compounds resulted only 1 and 2 at concentration of 10 μM that had weak activity against EGFR and InsR, with their % inhibitory were 30%, 27% (1), 45%, and 32% (2), respectively. The results suggested that the presence of a linear carboxylic acid group in both compounds could be of significance to the inhibitory properties against the two RTKs.

• Asian Pacific Journal of Cancer Prevention
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• v.16 no.16
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• pp.7179-7188
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• 2015

Cancer is a major health obstacle around the world, with hepatocellular carcinoma (HCC) and colorectal cancer (CRC) as major causes of morbidity and mortality. Nowadays, there isgrowing interest in the therapeutic use of natural products for HCC and CRC, owing to the anticancer activity of their bioactive constituents. Boswellia serrata oleo gum resin has long been used in Ayurvedic and traditional Chinese medicine to alleviate a variety of health problems such as inflammatory and arthritic diseases. The current study aimed to identify and explore the in vitro anticancer effect of B. Serrata bioactive constituents on HepG2 and HCT 116 cell lines. Phytochemical analysis of volatile oils of B. Serrata oleo gum resin was carried out using gas chromatography-mass spectrometry (GC/MS). Oleo-gum-resin of B. Serrata was then successively extracted with petroleum ether (extract 1) and methanol (extract 2). Gas-liquid chromatography (GLC) analysis of the lipoidal matter was also performed. In addition, a methanol extract of B. Serrata oleo gum resin was phytochemically studied using column chromatography (CC) and thin layer chromatography (TLC) to obtain four fractions (I, II, III and IV). Sephadex columns were used to isolate ${\beta}$-boswellic acid and identification of the pure compound was done using UV, mass spectra, $^1H$ NMR and $^{13}C$ NMR analysis. Total extracts, fractions and volatile oils of B. Serrata oleo-gum resin were subsequently applied to HCC cells (HepG2 cell line) and CRC cells (HCT 116 cell line) to assess their cytotoxic effects. GLC analysis of the lipoidal matter resulted in identification of tricosane (75.32%) as a major compound with the presence of cholesterol, stigmasterol and ${\beta}$-sitosterol. Twenty two fatty acids were identified of which saturated fatty acids represented 25.6% and unsaturated fatty acids 74.4% of the total saponifiable fraction. GC/MS analysis of three chromatographic fractions (I,II and III) of B. Serrata oleo gum resin revealed the presence of pent-2-ene-1,4-dione, 2-methyl- levulinic acid methyl ester, 3,5- dimethyl- 1-hexane, methyl-1-methylpentadecanoate, 1,1- dimethoxy cyclohexane, 1-methoxy-4-(1-propenyl)benzene and 17a-hydroxy-17a-cyano, preg-4-en-3-one. GC/MS analysis of volatile oils of B. Serrata oleo gum resin revealed the presence of sabinene (19.11%), terpinen-4-ol (14.64%) and terpinyl acetate (13.01%) as major constituents. The anti-cancer effect of two extracts (1 and 2) and four fractions (I, II, III and IV) as well as volatile oils of B. Serrata oleo gum resin on HepG2 and HCT 116 cell lines was investigated using SRB assay. Regarding HepG2 cell line, extracts 1 and 2 elicited the most pronounced cytotoxic activity with $IC_{50}$ values equal 1.58 and $5.82{\mu}g/mL$ at 48 h, respectively which were comparable to doxorubicin with an $IC_{50}$ equal $4.68{\mu}g/mL$ at 48 h. With respect to HCT 116 cells, extracts 1 and 2 exhibited the most obvious cytotoxic effect; with $IC_{50}$ values equal 0.12 and $6.59{\mu}g/mL$ at 48 h, respectively which were comparable to 5-fluorouracil with an $IC_{50}$ equal $3.43{\mu}g/mL$ at 48 h. In conclusion, total extracts, fractions and volatile oils of B. Serrata oleo gum resin proved their usefulness as cytotoxic mediators against HepG2 and HCT 116 cell lines with different potentiality (extracts > fractions > volatile oil). In the two studied cell lines the cytotoxic acivity of each of extract 1 and 2 was comparable to doxorubicin and 5-fluorouracil, respectively. Extensive in vivo research is warranted to explore the precise molecular mechanisms of these bioactive natural products in cytotoxicity against HCC and CRC cells.

• Proceedings of the KACD Conference
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• 2008.05a
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• pp.177-183
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• 2008

It was reported that esthetic composite resin restoration reinforces the strength of remaining tooth structure with preserving the natural tooth structure. However, it is unknown how much the strength would be recovered. The purpose of this study was to compare the fracture resistance of three types of undermined cavity filled with composite resin with that of non-cavitated natural tooth. Forty sound upper molars were allocated randomly into four groups of 10 teeth. After flattening occlusal enamel. undermined cavities were prepared in thirty teeth to make three types of specimens with various thickness of occlusal structure (Group $1{\sim}3$). All the cavity have the 5 mm width mesio-distally and 7 mm depth bucco-lingually. Another natural 10 teeth (Group 4) were used as a control group. Teeth in group 1 have remaining occlusal structure about 1 mm thickness, which was composed of mainly enamel and small amount of dentin. In Group 2, remained thickness was about 1.5 mm, including 0.5 mm thickness dentin. In Group 3, thickness was about 2.0 mm, including 1 mm thickness dentin. Every effort was made to keep the remaining dentin thickness about 0.5 mm from the pulp space in cavitated groups. All the thickness was evaluated with radiographic Length Analyzer program. After acid etching with 37% phosphoric acid, one-bottle adhesive (Single $Bond^{TM}$, 3M/ESPE, USA) was applied following the manufacturer's recommendation and cavities were incrementally filled with hybrid composite resin (Filtek $Z-250^{TM}$, 3M/ESPE, USA). Teeth were stored in distilled water for one day at room temperature, after then, they were finished and polished with Sof-Lex system. All specimens were embedded in acrylic resin and static load was applied to the specimens with a 3 mm diameter stainless steel rod in an Universal testing machine and cross-head speed was 1 mm/min. Maximum load in case of fracture was recorded for each specimen. The data were statistically analyzed using one-way analysis of variance (ANOVA) and a Tukey test at the 95% confidence level. The results were as follows: 1. Fracture resistance of the undermined cavity filled with composite resin was about 75% of the natural tooth. 2. No significant difference on fracture loads of composite resin restoration was found among the three types of cavitated groups. Within the limits of this study, it can be concluded the fracture resistance of the undermined cavity filled with composite resin was lower than that of natural teeth, however remaining tooth structure may be supported and saved by the reinforcement with adhesive restoration, even of that portion consists of mainly enamel and a little dentin structure.

• Restorative Dentistry and Endodontics
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• v.33 no.3
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• pp.177-183
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• 2008

It was reported that esthetic composite resin restoration reinforces the strength of remaining tooth structure with preserving the natural tooth structure. However, it is unknown how much the strength would be recovered. The purpose of this study was to compare the fracture resistance of three types of undermined cavity filled with composite resin with that of non-cavitated natural tooth. Forty sound upper molars were allocated randomly into four groups of 10 teeth. After flattening occlusal enamel, undermined cavities were prepared in thirty teeth to make three types of specimens with various thickness of occlusal structure (Group $1{\sim}3$). All the cavity have the 5 mm width mesiodistally and 7 mm depth bucco-lingually. Another natural 10 teeth (Group 4) were used as a control group. Teeth in group 1 have remaining occlusal structure about 1 mm thickness, which was composed of mainly enamel and small amount of dentin. In Group 2, remained thickness was about 1.5 mm, including 0.5 mm thickness dentin. In Group 3, thickness was about 2.0 mm, including 1 mm thickness dentin. Every effort was made to keep the remaining dentin thickness about 0.5 mm from the pulp space in cavitated groups. All the thickness was evaluated with radiographic Length Analyzer program. After acid etching with 37% phosphoric acid, one-bottle adhesive (Single $Bond^{TM}$, 3M/ESPE, USA) was applied following the manufacturer's recommendation and cavities were incrementally filled with hybrid composite resin (Filtek $Z-250^{TM}$, 3M/ESPE, USA). Teeth were stored in distilled water for one day at room temperature, after then, they were finished and polished with Sof-Lex system. All specimens were embedded in acrylic resin and static load was applied to the specimens with a 3 mm diameter stainless steel rod in an Universal testing machine and cross-head speed was 1 mm/min. Maximum load in case of fracture was recorded for each specimen. The data were statistically analyzed using one-way analysis of variance (ANOVA) and a Tukey test at the 95% confidence level. The results were as follows: 1. Fracture resistance of the undermined cavity filled with composite resin was about 75% of the natural tooth. 2. No significant difference in fracture loads of composite resin restoration was found among the three types of cavitated groups. Within the limits of this study, it can be concluded the fracture resistance of the undermined cavity filled with composite resin was lower than that of natural teeth, however remaining tooth structure may be supported and saved by the reinforcement with adhesive restoration, even if that portion consists of mainly enamel and a little dentin structure.

• Bulletin of the Korean Chemical Society
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• v.33 no.2
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• pp.473-482
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• 2012

A novel malemide epoxy containing Co(II), Ni(II) and Cu(II) ions have been synthesized by curing malemide epoxy resin (MIEB-13) and Co(II), Ni(II) and Cu(II) complexes of macrocyclic bis-hydrazone Schiff base. The Schiff base was synthesized by reacting 1,4-dicarbnyl phenyl dihydrazide with 2,6-diformyl-4-methyl phenol. The Schiff base and its Co(II), Ni(II) and Cu(II) complexes have been characterized by elemental analyses, spectral (IR, $^1H$ NMR, UV-vis., FAB mass, ESR), thermal and magnetic data. The curing reaction of maleimide epoxy compound with metal complexes was studied as curing agents. The stability of cured samples was studied by thermo-gravimetric analyses and which have excellent chemical (acid/alkali/solvent) and water absorption resistance. Further, the scanning electron microscopy (SEM) and definitional scanning colorimetric (DSC) techniques were confirmed the phase homogeneity of the cured systems.

• Bulletin of the Korean Chemical Society
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• v.27 no.10
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• pp.1542-1548
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• 2006

Maleimide modified epoxy compounds were prepared by reacting N-(4-hydroxyphenyl) maleimide (HPM) with diglycidylether of bisphenol-A. Triphenylphosphine was used as catalyst and methylethylketone as solvent. The resulting compound possessed both the oxirane ring and maleimide group. The curing reaction of the maleimide epoxy compound with amine curing agents such as 1-(2-aminoethyl) piperazine (AEP) and 5-amino-1,3,3-trimethylcyclohexane methylamine isophorone diamine, IPDA) were studied. Incorporation of maleimide groups in the epoxy resin provides cyclic imide structure and high cross-linking density to the cured resins. The cured samples were found to have good thermal stability, chemical resistance (acid/alkali/solvent) and water absorption resistance.

• Journal of the Korean Ceramic Society
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• v.22 no.1
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• pp.35-39
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• 1985

Synthetic mica $NaMg_{2.5}(Si_4O_{10})F_2 (Na-TSM)$ was treated with HCl solution and H-type exchange resin to investigate the chemical stability and the ion exchange by measuring the dissolution of chemical components and the exchanged $H^+$ ion. The replacement of $Na^+$ ion occurred in contact with HCl solution and H-type ion exchange resin at the surface of Na-TSM particles reached $Na^+$ ions at maximum value of 70~80%. $Mg^{2+}$ ion of octahedral layer became to dissolve from the pH2 solution and th amount of it dissolved in-creased almost proportional to $H^+$ ion concentration from around 0.02N $H^+$ ion equilibrium concentration. The crystalline structure of Na-TSM was destructed by dissolution of Mg2+ ion in cncentrated hydrochloric acid solution and resulted silica gel precipitation.

• Proceedings of the Korean Printing Society Conference
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• 2001.06a
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• pp.91-91
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• 2001

환경문제에 대해 오래 전부터 관심을 가져온 선진국은 잉크의 수성화에 주력하여 왔으며, 그 결과 이미 수용성 소재의 양산체재에 들어가 수성 원료 사업을 대형화하는 추세에 있다. 이에 한화석유화학 중앙연구소에선 스티렌/아크릴계 수용성 High Solid 수지를 개발하여, 수성 잉크용 분산제, Resin Fortified Emulsion (RFE), UV Resist 잉크, 수성코팅제, 바닥광택제 등에 적요하기 위한 응용기술을 개발하였다. 본 연구는 수성 잉크의 주요 구성 성분인 grinding vehicle. let-down vehicle로 사용되는 수용성 High Solid 수지 (SAA 수지) 및 이를 이용한 에멀젼 수지의 합성과 수성 잉크로의 응용에 대한 것이다. SAA(HCC Soluryl Resin) 수지는 구조적으로 Styrene, Alpha-methyl Styrene, crylic Acid의 삼원공중합체이며 약 70%의 소수성 물질과 30%의 친수성 물질이 Random 하게 중합되어 있으며 약 5000∼15000정도의 낮은 분자량을 가진 물질로, 고고형분에서도 낮은 점도를 유지하기 위하여 분자량과 좁은 분자량과 좁은 분자량을 가지는 수지를 연속벌크중합방법으로 합성하였다. 또한 이를 고분자 유화제로서 사용하여 수지보강 에멀젼수지 (RFE 수지, HCC Soluryl Emulsion) 를 제조하는데 사용하였으며, SAA수지 및 RFE수지를 수성잉크용 분산제, 잉크 바인더용으로 적용하였다.

• Nuclear Engineering and Technology
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• v.13 no.4
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• pp.237-244
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• 1981

The preliminary concentration of trace elements in uranium dioxide using an anion exchange resin is presented for neutron activation analysis. The uranyl solution in sulfuric acid is adjusted to the acidity of about pH 2.7 and loaded on a column of the anion exchange resin. An appropriate volume of eluates obtained from the column shows good recoveries of trace elements. By combining this preconcentration with a radiochemical separation scheme, which was developed for the determinations of impurities in aluminum, it is possible to determine 21 trace elements in reactor grade uranium dioxide.

• Bulletin of the Korean Chemical Society
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• v.31 no.8
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• pp.2272-2278
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• 2010

A new hybrid thermosetting maleimido epoxy compound 4-(N-maleimidophenyl) glycidylether (N-MPGE) is prepared by reacting N-(4-hydroxyphenyl) maleimide (HPM) with Epichlorohydrin by using benzyltrimethylammonium chloride as a catalyst. The resulting compound possesses both the oxirane ring and maleimide group. The curing reaction of these maleimidophenyl glycidylether epoxy compound (N-MPGE) with amines as curing agents such as ethylendiamine (EDA), diethylentriamine (DETA) and triethylenetetramine (TETA), aminoethylpiperazine (AEP) and isophoronediamine, IPDA), are studied. Incorporation of maleimide groups in the epichlorohydrin provides cyclic imide structure and high cross-linking density to the cured resins. The cured samples exhibited good thermal stability, excellent chemical (acid/alkali/solvent) and water absorption resistance. Morphological studies by the SEM technique further confirmed the phase homogeneity net work of the cured systems.