• Biomolecules & Therapeutics
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• v.27 no.1
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• pp.54-62
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• 2019

Cis-3-O-p-hydroxycinnamoyl ursolic acid (HCUA), a triterpenoid compound, was purified from Elaeagnus oldhamii Maxim. This traditional medicinal plant has been used for treating rheumatoid arthritis and lung disorders as well as for its anti-inflammation and anticancer activities. This study aimed to investigate the anti-proliferative and apoptotic-inducing activities of HCUA in oral cancer cells. HCUA exhibited anti-proliferative activity in oral cancer cell lines (Ca9-22 and SAS cells), but not in normal oral fibroblasts. The inhibitory concentration of HCUA that resulted in 50% viability was $24.0{\mu}M$ and $17.8{\mu}M$ for Ca9-22 and SAS cells, respectively. Moreover, HCUA increased the number of cells in the sub-G1 arrest phase and apoptosis in a concentration-dependent manner in both oral cancer cell lines, but not in normal oral fibroblasts. Importantly, HCUA induced p53-mediated transcriptional regulation of pro-apoptotic proteins (Bax, Bak, Bim, Noxa, and PUMA), which are associated with mitochondrial apoptosis in oral cancer cells via the loss of mitochondrial membrane potential. HCUA triggered the production of intracellular reactive oxygen species (ROS) that was ascertained to be involved in HCUA-induced apoptosis by the ROS inhibitors YCG063 and N-acetyl-L-cysteine. As a result, HCUA had potential antitumor activity to oral cancer cells through eliciting ROS-dependent and p53-mediated mitochondrial apoptosis. Overall, HCUA could be applicable for the development of anticancer agents against human oral cancer.

• Journal of the Korean Applied Science and Technology
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• v.18 no.1
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• pp.67-77
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• 2001

In search for several fatty acid with unusual structure in vegetable oils, we have found that unknown peaks were shown on GLC in the analysis of fatty acids of the lipids from the pulp of ripened jujube (Zizypus jujuba var. inermis) fruits. These fatty acids were identified as a series of cis-monoenoic acids with ${\omega}-5$ double bond system such as $C_{14:1{\omega}5}$, $C_{16:1{\omega}5}$ and $C_{18:1{\omega}5}$, including ${\omega}-7$ fatty acid as $C_{16:1{\omega}7}$ and $C_{18:1{\omega}7}$, by GLC, solid-phase extraction silver ion-column chromatographic, GLC-mass spectrometric and IR techniques. First of all, total fatty acid methyl esters were resolved into saturated and branched fatty acid, monoenoic acid, dienoic acid, and trienoic acid fraction, respectively, with 100% dichloromethane (DCM), DCM/acetone (9:1, v/v) 100% acetone, and acetone/ acetonitrile (97:3, v/v) solvent system. Unknown fatty acids were included in the monoenoic fraction and were confirmed to have cis-configuration by IR. Picolinyl esters of monoenoic fatty acids gave distinct molecular ion peak and dominant diagnostic peaks, for example, m/z 317, 220 and 260 fragment for $cis-C_{14:1{\omega}5}$, m/z 345, m/z 248 and 288 fragment for $cis-C_{16:1{\omega}5}$ and m/z 373, m/z 276 and 316 fragment for $cis-C_{18:1{\omega}5}$. In this way the occurrence of $cis-C_{16:1{\omega}7}$ and $cis-C_{18:1{\omega}7}$ could be deduced from the appearance of prominent fragments as m/z 345, 220 and 260, and m/z 373, 248 and 280. Level of total ${\omega}-5$ fatty acids amounted to about 30% in the fatty acid composition with the predominance of $C_{16:1{\omega}5}$ $ (18.7{\sim}25.0%)$, in the semi-ripened and/or ripened samples collected in September 14 ($C_{16:1{\omega}5}$ ; 18.7%, $C_{14:1{\omega}5}$ ; 3.6% and $C_{18:1{\omega}5}$ ; 3.0%), September 22 ($C_{16:1{\omega}5}$ ; 25.0%, $C_{14:1{\omega}5}$ ; 1.4% and $C_{18:1{\omega}5}$ ; 2.6%), and October $7 (C_{16:1{\omega}5}$ ; 24.7%, $C_{14:1{\omega}5}$ ; 7.7% and $C_{18:1{\omega}5}$ ; 2.5%). However, the lipids extracted from unripened jujube in July and August contain these unusual fatty acids as low as negligible. It could be observed that the level of ${\omega}-5$ fatty acids in the pulps increased sharply with an elapse of ripening time of jujube fruits. Other monoenoic fatty acids with ${\omega}-7$ series, $C_{16:1{\omega}7}$ (palmitoleic acid) and $C_{18:1{\omega}7}$ (cis-vaccenic acid) could be detected. And in the lipids of the kernel and leaf of jujube, none of ${\omega}-5$ fatty acids could be detected.

• Journal of the Korean Society of Food Science and Nutrition
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• v.31 no.2
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• pp.177-183
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• 2002

Cerebroside fatty acids, sugars and long-chain sphingoid bases in raw soybean and soybean fermented foods (chongkukjang and deunjang) were analyzed using gas chromatography-mass spectrometry (GC-MS) and high-pH anion exchange chromatography with pulsed amerometric detection (HPAEC-PAD). Fatty acids of acid-hydrolyzed cerebrosides were derivatized to O-TMS methylester and analysed. The major fatty acids in raw soybean and chongkukjang cerebrosides were identified as 2-hydroxyhexadecanoic acid (16 : 0h), 2-hydroxydocosanoic acid (22 : 0h) and 2-hydroxytetracosanoic acid (24 : 0h). In the case of deunjang cerebroside, 24 : 0h (40.9%) and 22 : 0h (23.4%) were major fatty acids, but 16 : 0h, 23 : 0h, 25 : 0h and 26 : 0h were also detected. Long-chain sphingoid bases of acid-hydrolyzed cerebrosides from raw soybean, chongkukjang and deunjang consisted primarily of 4-tracts, 8-tracts-sphingadienine (dihydroxy base, d18 : 2$\Delta$$^{4trans, 8trans}$) and sis-tracts isomers of 4-hydroxy-sphingenine (trihydroxy base, tl8:1$\Delta$$^{4trans or cis}$) with much less amounts of phytosphingosine (tl8: 0) and isomers of sphingenine (d18 : 1). Although deunjang is a soybean food fermented by fungi and microorganisms for a long period, 2-hydroxyoctadec-3-enoic acid (18 : 1h) and branched 9-methyl-4,8-sphingadienine known as compositional cerebroside fatty acids in Aspergillus species were not detected. Mass spectrum for sugar derivatives in cerebrosides of soybean foods including raw soybean and fermented soybean showed that C-1 of glucose moiety was linked to ceramide backbone as like a monoglucosylceramide.

• Asian Pacific Journal of Cancer Prevention
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• v.15 no.3
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• pp.1291-1298
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• 2014

Background: Evidence for associations between dietary factors and breast cancer risk is inconclusive among Chinese females. To evaluate this question, we conducted a systematic review of relevant case-control and cohort studies. Methods: Studies were systematically searched among 5 English databases (PudMed, ScienceDirect, Wiley, Clinicaltrials.gov, and Cochrane) and 3 Chinese databases (CNKI, WanFang, and VIP) until November 2012. Random effects models were used to estimate summary odds ratios (ORs) and the corresponding 95% confidence intervals (CIs). Results: Thirty one case-control studies and two cohort studies involving 9,299 cases and 11,413 controls were included. Consumption of both soy and fruit was significantly associated with decreased risk of breast cancer, with summary ORs of 0.65 (95% CIs: 0.43-0.99; I2=88.9%, P<0.001; N=13) and 0.66 (95% CIs: 0.47-0.91; $I^2$=76.7%, P<0.001; N=7), respectively. Consumption of fat was significantly associated with increased risk of breast cancer (OR=1.36; 95% CIs: 1.13-1.63; $I^2$=47.9%, P=0.088; N=6). There was nonsignificant association between consumption of vegetables and breast cancer risk (OR=0.72; 95% CIs: 0.51-1.02; $I^2$= 74.4%, P<0.001; N=9). However, sensitivity analysis based on adjusted ORs showed decreased risk of breast cancer was also associated with consumption of vegetables (OR=0.49; 95% CIs: 0.30-0.67). Conclusion: Both soy food and fruit are significantly associated with decreased risk of breast cancer among Chinese females, and vegetables also seems to be protective while dietary fatexerts a promoting influence.

• Proceedings of the Korean Society of Life Science Conference
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• 2006.09a
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• pp.71.1-71.1
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• 2006

• Proceedings of the Korean Society of Applied Pharmacology
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• 2002.07a
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• pp.210-210
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• 2002

• Proceedings of the Korea Environmental Mutagen Society Conference
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• 2002.05a
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• pp.91-91
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• 2002

• Bulletin of the Korean Chemical Society
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• v.19 no.8
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• pp.862-868
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• 1998

The Lewis acid mediated intramolecular additions of allylsilanes to acetal substrates are described. Excellent regio- and diastereoselectivity are achieved by boron trifluoride promoted cyclization of allysilane-acetals 5 and 8 derived from hydroxy allysilances 3. Cyclizations occur in moderate to high yields, providing directr routes to cis-2, 6-disubstituted 4-methylenetetrahydropyrans 6 and 9.

• Bulletin of the Korean Chemical Society
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• v.16 no.10
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• pp.981-984
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• 1995

New diamineplatinum(Ⅱ) complexes of cyclohexylidenemalonate (chm) ligand, A2Pt(OOC)2C=C(CH2)4CH2 (1, A2=ethylenediamine (en); 2, A2=propylenediamine (pn); 3, A=NH3; 4, A=isopropylamine (ipa)) have been prepared. Their oxidation with H2O2 has led to the corresponding dihydroxoplatinum(Ⅳ) complexes: cis, cis, trans-A2Pt((OOC)2C=C(CH2)4CH2)(OH)2 (5, A2=en; 6, A2=pn; 7, A=NH3; 8, A=ipa). The title complexes have been characterized by means of various spectroscopies and X-ray crystallography. 5 crystallizes in the monoclinic space group P21/a (Z=4) with a=12.098(7) Å, b=9.552(2) Å, c=16.258(4) Å, β=98.03(5)° and V=1860(1) Å3. The structure was refined to R=0.074. The local geometry around platinum atom is approximately octahedral with each hydroxide group in trans position. These platinum complexes are stable in aqueous solution. Pt(Ⅳ) complexes are readily reduced to the corresponding Pt(Ⅱ) complexes by ascorbic acid.

• Bulletin of the Korean Chemical Society
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• v.19 no.10
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• pp.1059-1063
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• 1998

Regiospecific total syntheses of (±)-11-deoxy-4-methoxy-10-oxo-βrhodomycinone (21a) and (±)-11-deoxy-1-methoxy-10-oxo-β-rbodomycinone (21b) are described. 2-(2-Bromoethyl)-1,3-dioxane (6) was transformed to naphthalenone 12, which was condensed with (phenylsulfonyl)-isobenzofuranone 13 to afford 7,8-dihydro-9-ethyl-6-hydroxy-4-methoxynaphthacen-5,12-dione (15). Epoxide 16 prepared from olefinic compound 15, reacted with HF/Pyr (7:3) to give 17. Dihydroxylation of 17 with t-BuOK/P(OMe)3/O2, selective cis-diol protection of mixed compounds 18 with phenylboronic acid in toluene, separation of cis-boronate 19 and trans-diol 20 by column chromatography on silica gel, and cleavage of the boronate group of 19 with 2-methylpentane-2,4-diol in acetic acid completed the construction of 21.