• Natural Product Sciences
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• 제12권4호
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• pp.210-213
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• 2006

A 4,5-dioxoaporphine type alkaloid, cepharadione B (1), a phenolic acid, protocatechuic acid (2), and flavonols, quercetin (3), afzelin (4), and quercitrin (5), were isolated from the EtOAc-soluble extract of the whole plants of Houttuynia cordata. All the isolates (1-5) were subjected to in vitro bioassays to evaluate advanced glycation end products (AGEs) formation and rat lens aldose reductase (RLAR) inhibitory activity. The three flavonols 3-5 exhibited a significant inhibitory activity on AGEs formation with $IC_{50}$ values of 66.9, 58.9, and $32.3{\mu}M$, respectively. While the two flavonol rhamnosides 4 and 5 showed a remarkable inhibitory activity against RLAR with $IC_{50}$ values of 0.81 and $0.16{\mu}M$, respectively.

• Natural Product Sciences
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• 제24권4호
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• pp.272-283
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• 2018

The root-knot nematode, Meloidogyne incognita caused a serious damage to many plants. The phenolic components of the leaves of Schinus terebinthifolius were investigated as potential nematicidal agents for M. incognita. Nine compounds were isolated and characterized as viz., 1,2,3,4,6-pentagalloyl glucose (1), kaempferol-3-O-${\alpha}$-L-rhamnoside (Afzelin) (2), quercetin-3-O-${\alpha}$-L-rhamnoside (Quercetrin) (3), myricetin (4), myricetin-3-O-${\alpha}$-L-rhamnoside (Myricetrin) (5), methylgallate (6), protocatechuic acid (7), quercetin (8), and gallic acid (9) using nuclear magnetic resonance (NMR) spectroscopy. Compound 1 showed pronounced nematicidal activity compared to Oxamyl as a positive control. It showed the lowest eggs-hatchability (34%) and the highest mortality in nematode population (21% after 72 hours of treatment) at a concentration of $200{\mu}g/mL$. It exhibited the best suppressed total nematode population, root galling and number of eggmasses in infected tomato plants. The total carbohydrates and proteins were also significantly induced by 1 with reduction in total phenolics and increase in defense-related proteins. Thus, compound 1 could be a promising, more safe and effective natural nematicidal agent for the control of root-knot nematodes.

• Journal of Applied Biological Chemistry
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• 제65권3호
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• pp.153-158
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• 2022

This study aimed to identify the phytochemical constituents of Lactuca serriola leaves and perform quantitative analysis of the methanol (MeOH) extract of L. serriola, L. indica, L. raddeana, L. sativa, and L. triangulata. Six compounds were isolated from the MeOH extracts of L. serriola using open column chromatography and identified as protocatechuic acid (1), caffeic acid (2), cynaroside (3), apigenin 7-glucuronide (4), luteolin (5), and apigenin (6) using ¹H-, ¹³C-nuclear magnetic resonance, and mass spectrometry. Quantitative analysis of the six compounds was performed on the MeOH extract of Lactuca species using high-performance liquid chromatography (HPLC) and an ultraviolet (UV). A reverse-phased column was used, and the UV absorbance was set to 280 nm. The contents of compounds 2 and 3 were the highest (1.58 and 2.64 mg/g ext., respectively) in L. serriola extracts. However, compounds 4 and 6 were higher (1.46 and 0.40 mg/g ext., respectively) in L. triangulata. These results provide quantitative data for the application of Lactuca species in the pharmaceutical and functional food industries.

• Journal of Applied Biological Chemistry
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• 제66권
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• pp.144-152
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• 2023

Two different extraction methods were used to evaluate the medical value of common rue, Ruta graveolens L. (RGL). The results of our 2,2-diphenyl-1-picrylhydrazyl and 2,2'-azino-bis-3-ethylbenzothiazoline-6-sulphonic acid assays indicated that the antioxidant activity of RGL essential oil extract obtained through steam distillation was very low, whereas ethanol (EtOH) extracts of RGL showed higher antioxidant activity. RGL essential oil was extracted by steam distillation and characterized by GC/MS analysis. Furthermore, EtOH extracts of RGL were obtained under reflux and analyzed by HPLC/PDA. The GC/MS results indicated that the ketone compounds 2-undecanol acetate, nonyl cyclopropanecarboxylate, and 2-nonanone accounted for more than 70% of the composition of RGL essential oil. The HPLC/PDA analyses indicated that the RGL extracts were rich in phenolic compounds such as protocatechuic acid, rutin, psoralen, xanthotoxin, and bergapten, among which rutin was the most abundant. Collectively, our results demonstrated that RGL contains high levels of phenolic compounds and could thus be commercialized as a valuable plant-derived antioxidant.

• Natural Product Sciences
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• 제22권3호
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• pp.154-161
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• 2016

Phytochemical investigation on the leaves of Pileostegia viburnoides Hook.f.et Thoms led to the isolation of twenty-five compounds, and their structures were identified as n-dotriacontane (1), taraxeryl acetate (2), friedelin (3), epifriedelinol (4), canophyllal (5), stigmast-4-en-3-one (6), stigmasterol (7), (24R)-5A-stigmastane-3,6-dione (8), ursolic acid (9), pomolic acid (10), umbelliferone (11), 4-epifriedelin (12), n-octatriacontanol (13), ${\beta}$-amyrin (14), ${\alpha}$-amyrin (15), taraxerol (16), nonadecanol (17), friedelane (18), arachic acid (19), protocatechuic acid (20), n-pentatriacontanol (21), hexadecanoic acid (22), vincosamide (23), daucosterol (24), and skimming (25), respectively. To our best knowledge, compounds 1, 2, 12, 13, 17 - 19 and 21-23 were new within Saxifragaceae family. Compounds 15, 16, and 20 were produced from this genus for the first time. Compounds 4, 14 and 25 were first obtained from species P. viburnoides and compounds 3, 5 - 11, and 24 were achieved from the leaves of P. viburnoides for the first time. Furthermore, the anti-neuroinflammatory activity of these isolates was evaluated.

• 한국버섯학회지
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• 제16권3호
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• pp.131-139
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• 2018

큰느타리버섯은 에르고스테롤 및 글루칸과 같은 기능성 물질의 함량이 높아 항산화 활성 및 프리바이오틱 효과를 일으키는 버섯이다. 큰느타리버섯은 향이 강하며 단단해 기호도가 높지만 장기간 소요되는 선박수출 등에서는 선도유지 기간 확보가 필요하다. 버섯의 품질에 영향을 미치는 외부요인은 온도, 상대습도, 공기조성 및 통풍 상태가 있으며 이로 인해 버섯의 호흡량, 수분 함량, 경도, 색도, pH 및 이취 등에 영향을 준다. 큰느타리버섯의 주요 장해는 갈변, 이취, 부패가 있으며, 이를 막기 위해 상품성이 높은 품종을 개발하거나 저장성을 높이는 처리 방법이 고안되고 있다. 버섯의 품질을 유지하기 위한 방법으로는 건조, 감마선 조사, 키토산 처리와 같은 수확 후 처리 방법과 CA 저장과 MA 포장을 통한 저장 방법이 있다. 버섯의 건조는 자연건조, 열풍건조, 동결건조, 진공건조, 전자파진공건조 방법이 있으며 동결건조 방법을 사용한 버섯의 성분저하가 비교적 낮았다. 1 kGy 감마선 조사가 고선량에 비해 저장기간 연장에 효과적이었으며 오일, protocatechuic acid, 왁스 등의 친수성 colloid를 키토산에 첨가하여 코팅처리 하였을 때 경도유지, 호흡 및 갈변이 억제되었다. 큰느타리버섯의 CA 저장조건은 $10^{\circ}C$ 이하의 온도에서 5kPa $O_2$ + 10~15kPa $CO_2$의 공기 조성이 제시되었으며 MA 포장으로는 미세천공을 갖는 PP필름을 이용한 능동적 기체조성 방법이 저장 중 품질유지에 효과적이었다.

• 한국식품저장유통학회지
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• 제20권2호
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• pp.242-249
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• 2013

(+)-Catechin을 $121^{\circ}C$에서 0, 1, 2, 3, 6, 12 h 동안 가열처리 하여 각각의 결과물에 대하여 DPPH 및 $ABTS^+$ radical 소거능 및 pancreatic lipase 저해활성을 평가하였다. DPPH 라디칼 소거능은 (+)-catechin의 3 h 가열결과물에서 가장 강한 활성인 $6.3{\pm}0.4{\mu}g/mL$의 $IC_{50}$값을 나타내었으며 6 h 가열결과물에서 $6.5{\pm}0.3{\mu}g/mL$의 $IC_{50}$ 값을 나타내었으며, 이들 활성은 (+)-catechin과 비교하였을 경우에도 높은 활성을 나타냄을 확인하였다. 또한 $ABTS^+$ 라디칼 소거능은 (+)-catechin의 3 h 가열결과물에서 가장 강한 활성인 $1.8{\pm}0.1{\mu}g/mL$의 $IC_{50}$값을 나타내었으며, 3 h 가열반응물로부터 분리한 화합물 중 화합물(1)과 화합물(2)가 이들 활성에 관여함을 시사하였다. 항비만 활성평가에 활용되고 있는 pancreatic lipase를 이용한 효능 평가에서 3 h 반응물의 $IC_{50}$값이 $377.1{\pm}11.1{\mu}g/mL$임을 확인하였고, 가열처리군별 HPLC 크로마토그램 및 상대함량으로 부터 (+)-catechin의 가열처리에 의해서 생성됨을 물질분리를 통해 구조결정한 (+)-epicatechin 및 protocatechuic acid 이외에 pancreatic lipase 저해활성을 나타내는 물질의 존재가 시사되었다. 향후 식품 및 음료에 광범위하게 존재하는 (+)-catechin의 가열조건에 따른 활성변화에 대한 보다 다양한 조건에서의 체계적인 연구가 필요하며 본 연구결과는 화합물의 구조변환을 통한 활성물질 개발을 위한 기초자료로 이용될 수 있을 뿐만 아니라 단일물질의 화학적 변화와 관련된 성분연구에 대한 기초자료로 활용가능하리라 사료된다.

• 대한본초학회지
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• 제30권3호
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• pp.19-24
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• 2015

Objectives : HPL-1, a novel herbal medicine which is composed of five herbs such as Kalopanacis Cortex, Chaenomelis Fructus, Raphani Semen, Atractylodis Rhizoma and Pulvis Aconiti Tuberis Purificatum, was developed for treatment of osteoarthritis. This study is aimed to develop analytical method for consistent quality control of HPL-1 and validate chromatographic method. Methods : Chromatographic analysis was performed using ultra-high performance liquid chromatography - diode array detector (UHPLC-DAD) equipped with RP-amide column, column oven, and auto sampler. Marker compounds [protocatechuic acid, chlorogenic acid, liriodendrin, 3,5-dicaffeoylquinic acid, ${\beta}$-D-(3-O-sinapoyl)-fructofuranosyl-$\alpha$-D-(6-O-sinapoyl)glucopyranoside and benzoylmesaconine] were separated by step gradient elution of acetonitrile and 0.1% phosphoric acid/water. The method validation was evaluated by quantitative validation parameters of linearity, accuracy, precision, limit of detection (LOD) and limit of quantification (LOQ) according to KFDA guideline.Results : An optimized method for six marker compounds in HPL-1 was established by UHPLC-DAD. The correlation coefficient (R²) with each calibration curve was greater than 0.99. The LOD and LOQ were within the range of 0.008-0.090 and $0.023-0.274{\mu}g/mL$, respectively. The relative standard deviation (RSD) of intra- and inter-day variability were less than 4.0%. The result of recovery test was range from 93.3-106.3% with RSD < 4.0%.Conclusions : These results suggest that the quantitative UHPLC method is precise, accurate, effective for quality evaluation of HPL-1. The method may also contribute to improve quality of crude drug preparations used for treatment of various diseases.

• Natural Product Sciences
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• 제12권4호
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• pp.221-225
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• 2006

Phytochemical examination of the fruits of Actinidia arguta has led to the isolation three organic acids, one coumarin, and three flavonoids. Structures of these compounds were elucidated as protocatechuic acid (1), caffeic acid (2), $caffeoyl-\beta-D-glucopyranoside$ (3), esculetin (4), quercetin (5), quercetin $3-O-\beta-D-galactopyranoside$ (6), and quercetin $3-O-\alpha-L-rhamnopyranosyl$ $(1\rightarrow6)-O-\beta-D-glucopyranoside$ (7) by comparisons with previously reported spectral data. To investigate the anti-inflammatory and anti-oxidative effects of these compounds, nitric oxide production inhibitory activity in LPS-stimulated RAW 264.7 cells and DPPH radical scavenging activities were examined. Nitric oxide productions were reduced significantly by the addition of compounds $[1(IC_{50}=59.27{\mu}g/ml),\;2(IC_{50}=27.95{\mu}g/ml),\;3(IC_{50}=73.09{\mu}g/ml),\;4(IC_{50}=67.44{\mu}g/ml),\;5(IC_{50}=17.40{\mu}g/ml),\;6(IC_{50}=41.99{\mu}g/ml),\;7(IC_{50}=54.46{\mu}g/ml)]$, and extracts $(IC_{50}=56.21{\mu}g/ml)$ compared with positive control, L-NMMA $(IC_{50}=14.48{\mu}g/ml)$. The phenolic compounds also showed anti-oxidative activities. Especially, Compounds $1(IC_{50}=8.87{\mu}g/ml),\;4(IC_{50}=3.41{\mu}g/ml),\;and\;5(IC_{50}=6.06{\mu}g/ml),\;$, showed potent anti-oxidative activities similar to L-ascorbic acid $(IC_{50}=5.89{\mu}g/ml)$.

• 한국식생활문화학회지
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• 제20권5호
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• pp.603-607
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• 2005

충치원인균인 Streptococcus mutans에 대한 페놀성 화합물(14종)의 항미생물활성은 hydroxybenzoic acid group에서는 syringic acid를 제외한 모든 화합물이 5와 10 mg/disc 함유량에서 $8.5{\sim}18mm$까지의 생육저해환을 나타내었다. 기타 phenolics 화합물에서는 catechol과 L-ascorbic acid가 저해능을 나타냈는데, 특히 catechol은 10 mg/disc 함유량은 $18.5{\sim}19.5mm$로 강한 항미생물활성을 나타냈다. Phenolic compounds의 최소저해농도는 S. mutans, M1 및 M2 균 모두에서 2,000 ppm의 농도에서 MIC 값을 나타내어 큰 차이를 보이지 않았으며, catechol만 1,000 ppm의 농도에서 높은 MIC 값을 나타내었다. 충치 관련 미생물인 S. mutans에 대해 항미생물활성이 인정된 7종의 페놀성 화합물을 대상으로 S. mutans가 생산하는 glucosyltransferase(GTase)의 활성저해능은 benzoic acid와 p-hydroxybenzoic acid 처리구에서는 100과 500 ppm 농도에서 약하게나마 GTase활성을 저해하는 경향을 나타냈으며, gallic acid 처리구는 10 ppm부터 활성을 나타내기 시작해서 100 ppm과 500 ppm에서 약 50%의 저해 활성을 나타냈다. 한편 catechol 처리구에서는 10 ppm에서 58.7%의 저해활성을 나타내었고, 50 ppm에서 60.7%, 100 ppm에서 88.4%, 그리고 500 ppm에서 89.6%의 높은 활성을 나타내어 catechol의 S. mutans에 대한 생육저해능 측정에서 높은 항미생물활성을 나타낸 결과와 동일한 경향을 나타냈다.