Ionization Neutralizes the Allergy-Inducing Property of 3-Pentadecylcatechol: A Urushiol Derivative

정항연,이태호,이형재,조정용,문재학 한국식품영양과학회 2020 Journal of medicinal food Vol.23 No.7

Urushiols are amphipathic compounds found in Rhus verniciflua Stokes that exhibit various biological activities. However, their practical use is very restricted due to their contact dermatitis-inducing property. Therefore, we applied the ionization method to remove the allergenic properties of the urushiols and to increase their usability. One of the natural urushiols, 3-pentadecylcatechol (PDC), was heated for 30 min with a solution of H2O and sodium carbonate (Na2CO3). The reaction product was analyzed by electrospray ionization mass spectrometry (ESI-MS). Ionized PDC with an m/z value of 316.9 and complexed PDCs with Na+ of 1 − 3 atoms with m/z values of 340.8, 365.2, and 380.8 were detected. PDC and ionized PDC (3 μmol/3 mg of Vaseline) treatments were applied on the rear of left ear of Sprague-Dawley rats once daily for 10 days. Erythema and swelling were observed on the ear skin treated with PDC, but not in case of ionized PDC. Compared with control, contact hypersensitivity-related biomarkers (neutrophils, eosinophils, immunoglobulin E, and histamine) in the blood were significantly higher only in the PDC-treated group. In addition, Il-1b, Il-6, Tnfα, and Cox-2 mRNA expression levels were dramatically increased in the ear tissue of PDC-treated rats, but in the ionized PDC-treated group, they were similar to those in the control group. Overall, it was confirmed that the allergenic property of the urushiol PDC was removed by ionization. This method is expected to be useful for preventing allergy induction in cooking and food processing using R. verniciflua Stokes.

Does 3-pentadecylcatechol, an urushiol derivative, get absorbed in the body? A rat oral administration experiment

정항연,이형재,조정용,문제학 한국식품과학회 2020 Food Science and Biotechnology Vol.29 No.7

Urushiols are important active compounds foundin the sap of the lacquer tree (Rhus verniciflua Stokes). Recently, various biological effects of urushiols, such asantioxidant, antimicrobial, and anticancer activities, havebeen reported. However, urushiols can also induce skinallergies. Nevertheless, the lacquer tree has traditionallybeen used in Korea as a folk medicine. In this study, weevaluated the absorption and metabolism of 3-pentadecylcatechol(PDC), a natural urushiol. PDC (48.0 mg/kg bodywt.) in 1 mL propylene glycol was orally administered torats (Sprague-Dawley, male, 6 weeks old). Blood plasma,urine, and feces were collected, separately. PDC was notdetected in the extracts from rat blood plasma and urine. However, 89.4 ± 5.2% of the orally administered PDCwas detected in the feces extracts, indicating that PDC waspredominantly excreted and not absorbed.

Flavonoid의 흡수·대사

정항연(Hang Yeon Jeong),조정용(Jeong Yong Cho),문제학(Jae Hak Moon) 한국차학회 2016 한국차학회지 Vol.22 No.4

Catechins are one group of the most characteristic constituents containing in tea, fruits, and vegetables. A lot of studies have shown that catechin intake is associated with lower risk of various diseases such as cardiovascular, diabetes, and cancer. Recently, various researches on absorption and metabolism of flavonoids including catechins have been reported. Absorption and metabolic studies have shown that the in vivo circulating form of most flavonoids is conjugates such as sulfate and/or glucuronide with or without O-methylation, with a few notable exceptions. It is very important to know the absorption and metabolic conversion of flavonoids involving bioavailability, pharmacokinetics, and urinary excretion in order to evaluate their in vivo bioactivities after intake. This review provides details on the absorption and metabolism of catechins including several flavonoids.

Comparison of Bioactive Compound Contents and In vitro and Ex vivo Antioxidative Activities between Peel and Flesh of Pear (Pyrus pyrifolia Nakai)

이상현,조정용,정항연,정다은,김두운,조세영,김월수,문제학 한국식품과학회 2015 Food Science and Biotechnology Vol.24 No.1

We compared chemical constituents and antioxidative activities between the flesh and peel of two Asian pears (Pyrus pyrifolia Nakai cv. Niitaka and Chuhwangbae). Total phenolic, flavonoid, and ascorbic acid contents in the peels were higher than those in the flesh. However, total tocopherol content between peels and flesh was not different. The peels exhibited higher free radical scavenging activities in the in vitro models of DPPH, ABTS+, nitrite radicals, and reducing capabilities than those of the flesh. Pear fruit extracts significantly prevented 3T3-L1 cells from undergoing H2O2-induced oxidation and the effect was higher by the peel extract than by the flesh extract. In addition, blood plasma of rats administered the peel extract showed higher antioxidative activity than that of rats administered the flesh extract. These results suggest that consumption of unpeeled Asian pear fruit may effectively increase antioxidant activity in the body.

Enhancement of antioxidative and antimicrobial activities of immature pear (Pyrus pyrifolia cv. Niitaka) fruits by fermentation with Leuconostoc mesenteroides

이상원,조정용,정항연,나태웅,이상현,문제학 한국식품과학회 2016 Food Science and Biotechnology Vol.25 No.6

Immature pear (Pyrus pyrifolia cv. Niitaka) fruits were fermented with Leuconostoc mesenteroides and Aspergillus oryzae, which are commonly used as starters for manufacturing fermented foods. Fermented immature pear fruit extracts (FIPF) by L. mesenteroides showed significantly higher radical-scavenging activity using DPPH, ABTS, superoxide anion, and hydroxyl radicals and reducing power capacity than unfermented immature pear fruit extracts. L. mesenteroides-FIPF more effectively inhibited the formation of cholesteryl ester hydroperoxide in copper ion-induced rat blood plasma. In addition, the L. mesenteroides-FIPF strongly inhibited tyrosinase activity and the growth of pathogenic skin bacteria. In contrast, enhanced antioxidative and antibacterial activities were not apparent in A. oryzae-FIPF. The antioxidative and antimicrobial activities of the fermented and unfermented immature pear fruits were correlated with the flavonoid contents. These results indicate that fermentation enhances antioxidative and antimicrobial activities of immature pear fruits.

Isolation of five proanthocyanidins from pear (Pyrus pyrifolia Nakai) fruit peels

정다은,조정용,이유건,정항연,이형재,문제학 한국식품과학회 2017 Food Science and Biotechnology Vol.26 No.5

Five proanthocyanidins, two B-type dimers and three A-type trimers, were purified and isolated from the fruit peels of Pyrus pyrifolia Nakai cv. Chuhwangbae. The isolated compounds were identified as (–)-epicatechin gallate-(4β → 8)-(–)-epicatechin (Hahashi et al. in Ann Biol Res 3:3200–3207, 2012), (–)-epicatechin-(4β → 8)-(–)-epicatechin (procyanidin B2) (Tanrioven and Eksi in Food Chem 93:89–93, 2005), (–)-epicatechin-(4β → 8, 2β → O-7)-(–)-epicatechin-(4β → 8)-(–)-epicatechin (cinnamtannins B1) (Salta et al. in J. Fun. Food 2: 153–157, 2010), (–)-epicatechin-(4β → 8)-(–)-epicatechin-(4β → 8, 2β → O-7)-(–)-epicatechin (aesculitannin A) (Challice and Westwood in Phytochemistry 11: 37–44, 1972), and (–)-epicatechin-(4β → 6)-(–)-epicatechin-(4β → 8, 2β → O→7)-(–)-epicatechin (Es-Safi et al. in J Agric Food Chem 54: 6969–6977, 2006). Their structures were determined by nuclear magnetic resonance and mass spectrometry. The three A-type proanthocyanidin trimers were identified for the first time from pear.

Phenolics and eudesmanolide from aged common sage exudate with sugar

김태연,조정용,이유건,정항연,이형재,문제학 한국식품과학회 2017 Food Science and Biotechnology Vol.26 No.6

Nineteen compounds including one new flavanone were isolated from the juice of aged common sage exudate with sugar (ACSE). The isolated compounds were identified by NMR and MS analyses as levodopa methyl ester (1), 3,4-dihydroxybenzoic acid (2), (S)-8-hydroxy-4- hydroxy-phenylpropanoic acid (3), 4-hydroxybenzoic acid ethyl ester (4), cis-caffeic acid (5), trans-caffeic acid (6), esculetin (7), (S)-8-hydroxy-3,4-dihydroxy-phenylpropanoic acid ethyl ester (8), cis-rosmarinic acid (9), trans-rosmarinic acid (10), trans-rosmarinic acid methyl ester (11), 6-methoxy- 7,8,30,50-tetrahydroxyflavanone (12), nepetin (13), trans-caffeic acid ethyl ester (14), luteolin (15), cis-caffeic acid ethyl ester (16), 6-methoxynaringenin (17), 1a-acetoxy- 2-oxo-eudesman-3,7(11)-dien-8b,12-olide (18), and hispidulin (19). Compound 12 was isolated for the first time from nature and seven compounds (1, 3, 4, 7, 8, 14, and 18) were newly identified from common sage. Of them, 15 isolated phenolic compounds (1–3, 5–8, 10–15, 17, and 19) were detected in ACSE juice, while only 10 was detected in the fresh common sage.

관행 및 유기재배 현미의 생리활성 성분의 함량 및 항산화활성 비교

김기안,조정용,이유석,이형재,정항연,이유건,문제학,Kim, Gee An,Cho, Jeong-Yong,Lee, You Seok,Lee, Hyoung Jae,Jeong, Hang Yeon,Lee, Yu Geon,Moon, Jae-Hak The Korean Society of Food Preservation 2017 한국식품저장유통학회지 Vol.17 No.5

The content of bioactive substances and antioxidative activity in conventionally grown brown rice (CGBR) and organically grown brown rice (OGBR) were compared. Minerals (mg/100 g) such as magnesium (OGBR, $168.59{\pm}2.62$; CGBR, $121.43{\pm}2.22$), copper (OGBR, $0.50{\pm}0.06$; CGBR, $0.41{\pm}0.05$), and manganese (OGBR, $4.70{\pm}0.04$; CGBR, $2.49{\pm}0.02$) were higher in OGBR than in CGBR (p<0.05). In addition, levels of (${\mu}g/100g$) vitamins B2 (OGBR, $27.22{\pm}2.56$; CGBR, $22.12{\pm}2.24$) and B6 (OGBR, $46.32{\pm}2.66$; CGBR, $39.91{\pm}3.32$) were higher in OGBR than in CGBR (p<0.05). The contents (mg/100 g) of ${\beta}$-sitosterol (OGBR, $27.40{\pm}2.79$; CGBR, $24.75{\pm}1.06$), total phenolic (OGBR, $6.72{\pm}0.02$; CGBR, $6.64{\pm}0.02$), and ferulic acid (OGBR, $1.75{\pm}0.45$; CGBR, $1.11{\pm}0.14$) as well as the antioxidative activity (OGBR, $53.09{\pm}1.90%$; CGBR, $48.29{\pm}3.38%$) evaluated using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging assay were higher in OGBR than in CGBR, although no significant differences between samples were observed. In comparison to the control group, brown rice samples significantly inhibited cholesteryl ester hydroperoxide formation in rat plasma subjected to copper ion-induced lipid peroxidation. The inhibitory effect of OGBR was higher than that of CGBR. These results indicate that OGBR showed higher levels of bioactive substances and enhanced antioxidative activity than CGBR, although the differences were not statistically significant.

녹차 추출물 첨가 김 스낵의 항산화 활성

박정희(Jeong Hee Park),정항연(Hang Yeon Jeong),조정용(Jeong Yong Cho),문제학(Jae Hak Moon) 한국차학회 2017 한국차학회지 Vol.23 No.4

본 연구에서는 녹차의 항산화 활성이 증진된 김 스낵을 제조하고자, 데리야끼소스와 칠리소스를 기반으로 8% 녹차 추출물을 첨가하여 김 스낵을 제조하였으며, 이들을 대상으로 총 페놀성 화합물의 함량을 조사하고, DPPH 및 ABTS+ radical-scavenging 활성과 환원력을 평가하였다. 칠리소스를 이용하여 제조된 김 스낵은 총 페놀성 화합물함량 및 항산화 활성이 데리야끼소스를 이용한 김 스낵보다 월등히 높았으며, 특히 칠리소스에 녹차 추출물을 첨가하였을 때 그 함량 및 활성이 더욱 높아졌다. 그러나 데리야끼소스를 이용하여 제조한 김 스낵의 경우 녹차 추출물을 첨가하더라도 총 페놀성 화합물 및 항산화 활성의 증가는 매우 미미한 수준이었다. 녹차 추출물이 첨가된 김 스낵의 항산화 활성 및 환원력 향상 정도는 총 페놀성 화합물의 함량 향상 정도와 비슷한 경향을 보여 녹차 추출물 첨가 데리야끼소스와 칠리소스를 기반으로 한 김 스낵의 항산화 활성 향상은 catechin류를 포함한 녹차에 함유된 항산화 화합물에 의한 효과로 판단되었다. This study was conducted to investigate the total phenolic contents and antioxidative activities of laver snacks prepared with the addition of 8% green tea hot water extract, based on teriyaki and chili sauces. The chili sauce-based laver snacks exhibited a higher total phenolic content than the teriyaki sauce-based ones. In addition, compared to the teriyaki sauce-based laver snacks, the chili sauce-based ones showed higher antioxidative activities in assays using 1,1-diphenyl-2-picrylhydrazyl and 2,2 -azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radicals as well as reducing power. Especially, when green tea extract was added to the chili sauce-based laver snack, its total phenolic content and antioxidative activities were significantly increased. The addition of green tea extract to the teriyaki sauce-based laver snack resulted in a slight increase in the total phenolic content and antioxidant activities. The antioxidant activities of the laver snacks were correlated with the total phenolic contents.

Comparison of the content of bioactive substances and antioxidative activity between conventionally and organically cultivated brown rice (Oryza sativa L.)

김기안,조정용,이유석,이형재,정항연,이유건,문제학 한국식품저장유통학회 2017 한국식품저장유통학회지 Vol.24 No.3

The content of bioactive substances and antioxidative activity in conventionally grown brown rice (CGBR) and organically grown brown rice (OGBR) were compared. Minerals (mg/100 g) such as magnesium (OGBR, 168.59±2.62; CGBR, 121.43±2.22), copper (OGBR, 0.50±0.06; CGBR, 0.41±0.05), and manganese (OGBR, 4.70±0.04; CGBR, 2.49±0.02) were higher in OGBR than in CGBR (p<0.05). In addition, levels of (μg/100 g) vitamins B2 (OGBR, 27.22±2.56; CGBR, 22.12±2.24) and B6 (OGBR, 46.32±2.66; CGBR, 39.91±3.32) were higher in OGBR than in CGBR (p<0.05). The contents (mg/100 g) of β-sitosterol (OGBR, 27.40±2.79; CGBR, 24.75±1.06), total phenolic (OGBR, 6.72±0.02; CGBR, 6.64±0.02), and ferulic acid (OGBR, 1.75±0.45; CGBR, 1.11±0.14) as well as the antioxidative activity (OGBR, 53.09±1.90%; CGBR, 48.29±3.38%) evaluated using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging assay were higher in OGBR than in CGBR, although no significant differences between samples were observed. In comparison to the control group, brown rice samples significantly inhibited cholesteryl ester hydroperoxide formation in rat plasma subjected to copper ion-induced lipid peroxidation. The inhibitory effect of OGBR was higher than that of CGBR. These results indicate that OGBR showed higher levels of bioactive substances and enhanced antioxidative activity than CGBR, although the differences were not statistically significant.