• Title/Summary/Keyword: ${\beta}-sitosterol(2)$

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Chemical Constituents of the Root of Dystaenia takeshimana and Their Anti-Inflammatory Activity

  • Kim, Ju-Sun;Kim, Jin-Cheul;Shim, Sang-Hee;Lee, Eun-Ju;Jin, Wen-Yi;Bae, Ki-Hwan;Son, Kun-Ho;Kim, Hyun-Pyo;Kang, Sam-Sik;Chang, Hyeun-Wook
    • Archives of Pharmacal Research
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    • v.29 no.8
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    • pp.617-623
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    • 2006
  • In our ongoing search for bioactive compounds originating from the endemic species in Korea, we found that the hexane and EtOAc fractions of the MeOH extract from the root of Dystaenia takeshimana (Nakai) Kitagawa (Umbelliferae) showed cyclooxygenase-2 (COX-2) and 5- lipoxygenase (5-LOX) dual inhibitory activity by assessing their effects on the production of prostaglandin $D_2\;(PGD_2)$ and leukotriene $C_4\;(LTC_4)$ in mouse bone marrow-derived mast cells. By activity-guided fractionation, five coumarins, viz. psoralen (2), xanthotoxin (3), scopoletin (4), umbelliferone (5), and (+)-marmesin (6), together with ${\beta}-sitosterol$ (1), were isolated from the hexane fraction, and two phenethyl alcohol derivatives, viz. 2-methoxy-2-(4'-hydroxyphenyl)ethanol (7) and 2-hydroxy-2-(4'-hydroxyphenyl)ethanol (8), three flavonoids, viz. apigenin (9), luteolin (10), and cynaroside (11), as well as daucosterol (12) were isolated from the EtOAc fraction using silica gel column chromatography. In addition, D-mannitol (13) was isolated from the BuOH fraction by recrystallization. Two of the coumarins, scopoletin (4) and (+)- marmesin (6), the two phenethyl alcohol derivatives (7, 8) and the three flavonoids (9-11) were isolated for the first time from this plant. Among the compounds isolated from this plant, the five coumarins as well as the three flavonoids showed COX-2/5-LOX dual inhibitory activity. These results suggest that the anti-inflammatory activity of D. takeshimana might in part occur via the inhibition of the generation of eicosanoids.

Isolation and Identification of Bioactive Compounds from the Tuber of Brassica oleracea var. gongylodes

  • Prajapati, Ritu;Seong, Su Hui;Kim, Hyeung Rak;Jung, Hyun Ah;Choi, Jae Sue
    • Natural Product Sciences
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    • v.26 no.3
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    • pp.214-220
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    • 2020
  • Brassica oleracea var. gongylodes (red kohlrabi) is a biennial herbaceous vegetable whose edible bulbotuber-like stem and leaves are consumed globally. Sliced red kohlrabi tubers were extracted using methanol and the concentrated extract was partitioned successively with dichloromethane (CH2Cl2), ethyl acetate (EtOAc), n-butanol (n-BuOH) and water (H2O). Repeated column chromatography of EtOAc fraction through silica, sephadex LH-20 and RP-18 gel led to isolation of eleven compounds of which compound 1 was a new glycosylated indole alkaloid derivative, 1-methoxyindole 3-carboxylic acid 6-O-β-D-glucopyranoside. Others were known compounds namely, β-sitosterol glucoside (4), 5-hydroxymethyl-2-furaldehyde (5), methyl-1-thio-β-D-glucopyranosyl disulfide (6), 5-hydroxy-2-pyridinemethanol (7), (3S,4R)-2-deoxyribonolactone (8), n-butyl-β-D-fructopyranoside (9), uridine (10) and three fructose derivatives, D-tagatose (11), β-D-fructofuranose (12) and β-D-fructopyranose (13). Similarly, isolation from CH2Cl2 fraction gave two known indole alkaloids, indole 3-acetonitrile (2) and N-methoxyindole 3-acetonitrile (3). The structure elucidation and identification of these compounds were conducted with the help of 13C and 1H NMR, HMBC, HMQC, EIMS, HR-ESIMS and IR spectroscopic data, and TLC plate spots visualization. Compounds 2, 3, 4, 5, 6, 7, 8 and 9 are noted to occur in kohlrabi for the first time. Different bioactivities of these isolated compounds have been reported in literature.

Constituents from the Roots of Hemerocallis fulva (원추리 지하부의 성분 연구)

  • Kim, Ju-Sun;Son, Kun-Ho;Chang, Hyeun-Wook;Kim, Hyun-Pyo;Bae, Ki-Hwan;Kang, Sam-Sik
    • Korean Journal of Pharmacognosy
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    • v.33 no.2 s.129
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    • pp.105-109
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    • 2002
  • Besides chrysophanol and friedelin, mixtures of n-hydrocarbons [pentacosane (72.6%), heptacosane (14.6%), tetracosane (5.8%), nonacosane (4.1 %) and hexacosane (2.9%)], n-hydrocarbon alcohols [octacosanol (70.5%) and hexacosanol (29.5%)], l-monoacyl glycerols [acyl part; behenic acid (43.5%), lignoceric acid (32.4%), cerotic acid (9.3%), tricosanoic acid (8.9%), pentacosanoic acid (2.6%), octacosanoic acid (2.3%), heneicosanoic acid (1.0%)], wax esters [behenic acid (56.3%), lignoceric acid (23.0%), cerotic acid (19.8%), tricosanoic acid (4.6%), octacosanoic acid (4.0%), pentacosanoic acid (1.7%), triacontanoic acid (0.6%)/ octacosanol (33.7%), hexacosanol (21.0%), tetracosanol (15.6%), triacontanol (10.5%), docosanol (6.0%), tricosanol (6.0%), heptacosanol (4.2%), nonacosanol (3.0%)] and sterols [${\beta}-sitosterol$ (73.2%), stigmasterol (14.6%), campesterol (12.2%)] were isolated from the roots of Hemerocallis fulva. The acid : alcohol combinations of the major wax esters were $C_{48}$: 22 : 26, 24 : 24, $C_{46}$: 22 : 24, and $C_{44}$: 22 : 22. This is the first report of l-monoacyl glycerols and friedelin from this plant. All isolates were identified on the basis of spectral data and chemical reactions.

Isolation, Identification and Characterization of Phytophthora katsurae, Causing Chestnut Ink Disease in Korea

  • Lee, Jong-Kyu;Jo, Jong-Won;Shin, Keum-Chul;Lee, Sang-Hyun;Lee, Sang-Yong
    • The Plant Pathology Journal
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    • v.25 no.2
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    • pp.121-127
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    • 2009
  • Since July 2005, survey of chestnut ink disease was carried out in chestnut stands located at southern parts of Korea. Dead chestnut trees showing inky ooze on necrotic trunks were found in two different locations. In order to isolate and identify the causal fungus, infected tissues and soil samples around dead or dying trees were collected and placed on Phytophthora-selective medium. Rhododendron and chestnut tree leaves were used as a bait to isolate the fungus from soil samples by attracting zoospores in soil suspensions. On V-8 culture medium, the isolates produced homothallic oogonia with protuberances ($34.0-46.2{\times}21.9-26.7{\mu}m$) abundantly, but did not produced sporangia. Mass production of sporangia was possible by immersing agar plugs with actively growing mycelium in the creek water at $18^{\circ}C$ for 3 days. Sporangia were papillate, and ovoid to obpyriform ($17.0-38.9{\times}14.6-29.2{\mu}m$) in shape. Comparison of the ITS sequences revealed that the isolates had 100% identity to the P. katsurae isolates from Japan and New Zealand and 99.6% identity to other P. katsurae isolates. All of the examined isolates from Korea were completely identical to each other in ITS sequence. Numerous sporangia were formed in filtered as well as unfiltered creek water, but no sporangia formed in sterilized distilled water. Light induced sporangia formation, but has no influence on oospore formation. Amendments of ${\beta}$-sitosterol in culture media have no significant effect on mycelial growth but significantly stimulate oospore and sporangia formation.

Antioxidant and anticancer activities of Adenophora triphylla leaf and root extracts (새싹 잔대 잎과 뿌리의 항산화 및 항암 효과)

  • Seon Young Yoon;Ki Hyun Kim;Tae Kyung Hyun
    • Journal of Plant Biotechnology
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    • v.50
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    • pp.137-141
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    • 2023
  • The root of Adenophora triphylla is a highly valued medicinal resource that is used to prevent human obesity, cancer, and inflammation, whereas young leaves or sprouts of A. triphylla are used as food ingredients. In this study, we compared the antioxidant and anticancer activities of 70% ethanol extracts of A. triphylla roots and leaves. The leaf extract exhibited stronger 2,2-diphenyl-1-picrylhydrazyl (DPPH)-radical scavenging activity, reducing power, and oxygen radical absorbance capacity (ORAC) than the root extract. Furthermore, the leaf extract was observed to be a potent source of anticancer compounds that were effective against A549 (lung cancer), LNcaP (prostate cancer), SKOV3 (ovarian cancer), and Caco-2 (colorectal cancer) cells. These results indicate that not only the roots but also the leaves of A. triphylla can serve as valuable sources of functional materials in the pharmaceutical industry.

Evaluation of Sewage Pollution by Coprostanol in the Sediments from Jinhae Bay, Korea (퇴적물내 Coprostanol을 이용한 진해만의 도시하수오염 평가)

  • CHOI Minkyu;MOON Hyo-Bang;KIM Sang-Soo;PARK Jong-Soo
    • Korean Journal of Fisheries and Aquatic Sciences
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    • v.38 no.2
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    • pp.118-128
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    • 2005
  • Surface sediment samples from 31 stations in Jinhae Bay were analyzed to evaluate the pollution by sewage from the spatial distribution of the fecal sterol, coprostanol. The sums of eight sterols (coprostanol, epicholestanol, epicoprostanol, cholesterol, cholestanol, brassicasterol, stigmasterol and $\beta$-sitosterol) were in the range of $2,703-27,154{\cal}ng/{\cal}g$ dry weight. The concentrations of the coprostanol in the sediments, which is a good tracer of sewage-derived organic contamination, were in the range of $76-3,964{\cal}ng/{\cal}g$ dry weight. The levels of coprostanol were much higher (almost one order of magnitude) at stations close to the big cities such as Masan and Jinhae. However, those levels were comparable to or lower than those previously reported in other foreign locations. Some ratios of coprostanol to other sterols and multivariate analysis could provide us with the information on the origin of the sterols being from sewage, plankton, and/or benthos. Those showed sewage dominance at the stations near the cities Masan and Jinhae, plankton dominance at the center of Jinhae Bay and mainly marine fauna origin at the mouth of Jinhae Bay. These results suggest that the contents of sterols and some ratios of these components are quite powerful tracer for the detection of the origin of the organic contaminants in the coastal environments.

Characterization of Lipophilic Nutraceutical Compounds in Seeds and Leaves of Perilla frutescens

  • Um, Seungduk;Bhandari, Shiva Ram;Kim, Nam-Hoon;Yang, Tae-Jin;Lee, Ju Kyoung;Lee, Young-Sang
    • Horticultural Science & Technology
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    • v.31 no.2
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    • pp.231-238
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    • 2013
  • Perilla frutescens, which comprises var. frutescens and var. crispa, has been cultivated traditionally in Asian countries as an edible oil, leaf vegetable, and medicinal crop. To evaluate the lipophilic phytonutrient properties of P. frutescens, we selected 54 Perilla accessions [19 landraces of var. frutescens (FL), 22 weedy type var. frutescens (FW), 9 weedy type var. crispa (CW), 2 cultivars of var. frutescens widely cultivated for seed oil (FCS), and 2 cultivars of var. frutescens cultivated as a leaf vegetable (FCL)] and analyzed their seeds and leaves for vitamin E, squalene, and phytosterols. Among the four vitamin E isomers analyzed, ${\gamma}$-tocopherol was the major form of vitamin E in seeds, whereas ${\alpha}$-tocopherol was the major form in leaves of all types of P. frutescens. The highest total vitamin E content in seeds was present in FL ($170.0mg{\cdot}kg^{-1}$), whereas that in leaves was highest in FCL ($358.1mg{\cdot}kg^{-1}$). The highest levels of squalene in seeds and leaves were in FL ($65.5mg{\cdot}kg^{-1}$) and CW ($719.3mg{\cdot}kg^{-1}$), respectively. Among the three phytosterols, ${\beta}$-sitosterol occurred in the highest amount in both leaves and seeds of all of the crop types. Phytonutrient contents were comparatively higher in leaves than in seeds of all crop types. All of these results suggest that the consumption of leaves and seeds of Perilla crops could be beneficial to human health, as Perilla possesses considerable amounts of various lipophilic compounds.

Isolation of Melanin Biosynthesis Inhibitory Compounds from the Phellodendri Cortex (황백(黃柏)으로부터 멜라닌 생합성 억제 물질의 분리)

  • Lee, Jong-Gu;Choi, Ji-Young;Oh, Joon-Seok;Jung, Hee-Wook;Choi, Eun-Hyang;Lee, Hee-Sang;Kim, Jeong-Ah;Chang, Tae-Soo;Son, Jong-Keun;Lee, Seung-Ho
    • Korean Journal of Pharmacognosy
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    • v.38 no.4
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    • pp.387-393
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    • 2007
  • By screening inhibitory activities on the melanin polymer biosynthesis in B-16 mouse melanoma cell lines, MeOH extract of Phellodendri Cortex was found to have inhibitory effect on melanin polymer biosynthesis. Twelve compounds were isolated from the MeOH extract of P. Cortex. They were identified as obacunone (1), limonin (2), ${\beta}-sitosterol$ (3), bis(2-methylheptyl) phthalate (4), cycloeucalenol (5), berberine (6), palmatine (7), jatrorrhizine (8), syringin (9), umbelliferone (10), rutaecarpine (11) and scopoletin (12) by comparison of their physical and spectral data with those of authentic samples. Among the isolated compounds, berberine (6) and palmatine (7) showed potent inhibitory effect on the melanin polymer biosynthesis in cultured B-16 mouse melanoma cell lines, with Inhibition rate of 96% and 90%, respectively. As a positive control, arbutin exhibited an inhibition rate of 56%.

Distribution of sewage-derived organic matter using fecal sterol in Masan Bay, Korea (마산만의 하수기인 유기물 fecal sterol의 분포)

  • Choi Min-Kyu;Moon Hyo-Bang;Kim Sang-Soo;Lee Yoon
    • Journal of Environmental Science International
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    • v.14 no.5
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    • pp.481-490
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    • 2005
  • Surface sediments and seawater were sampled at Masan and Haengam Bays of Korea, to evaluate contamination by sewage-derived organic matter using fecal sterols, Six stream-water samples into Masan and Haengam Bays were also sampled. Total concentrations of eight sterols (coprostanol, epichloestanol, epicoprostanol, cholesterol, cholestanol, brassicasterol, stigmasterol and $\beta-sitosterol$) were in the range of $1,274\~4,768{\mu}g/g$ dry weight in suspended particulate from the stream-water, $292\~2,244{\mu}g/g$ dry weight in suspended particulate from the seawater and $4.5\~27.2{\mu}g/g$ dry weight in the sediments. Although sterol compositions in sediments, seawater and stream-water were different, cholesterol was the predominant sterol in all samples. The proportion and concentration of coprostanol, a sewage tracer, in stream-water was much higher than those in sediment and seawater. The sterol levels including coprostanol in the sediments and seawater were higher at inner basin than at the outer bay. Some molecular indices and multivariate statistical analysis were used to assess the origin of these sterols and sewage contamination in the study area. The sterol composition patterns in stream-water were mainly associated with contamination by sewage-derived organic matters and those of seawater were associated with the activities of marine-originated organisms. Sterol levels in the sediments were both from the sewage input through stream-water and the marine- originated organisms. This survey suggests that the main source/route of sewage-derived organic matters in Masan Bay is the input of stream-water into the bay.

Characterization of Inorganic Components, Free Sugars, Amino Acids, and Fatty Acids in Angelica gigas Nakai (참당귀의 무기성분, 유리당, 아미노산 및 지방산 함량 특성)

  • Kil, Hyun Young;Seong, Eun Soo;Sim, Jae Man;Choi, Seon Kang;Heo, Kweon;Yu, Chang Yeon
    • Korean Journal of Medicinal Crop Science
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    • v.23 no.6
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    • pp.454-459
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    • 2015
  • Background : The major compounds of Angelica species are decursin, decursinol angelate, nodakenin, umbelliferone and ${\beta}$-sitosterol, which act anti-inflammatories, reduce pains, protect the liver and enhance the immune system. This study investigated the chemical compositions, minerals, metals, sugars and overall amino acid composition in Angelica gigas Nakai. Methods and Results : Powder of Angelica roots smaller than 30 mesh were used. Physico-chemical analysis revealed the presence of carbohydrates (62.0%), crude proteins (13.9%), moisture (11.4%), crude fats (7.3%) and ash (5.4%). Results showed that potassium was present in the highest amount (1,859 ppm), followed by magnesium (214.5 ppm), calcium (147.3 ppm) and sodium (6.0 ppm). Free sugar profiles showed the presence of sucrose (29.3 g/100 g). The total amino acids concentrations was 9,752 mg/100 g, the most common and dominant amino acids were arginine (2,181 mg/100 g), glutamic acid (1,212 mg/100 g) and aspartic acid (834 mg/100 g). The total free amino acids contents was 1,476 mg/100 g, in which the most common amino acid were arginine (932 mg/100 g), glutamic acid (127 mg/100 g), and ${\gamma}$-aminobutyric acid (80.4 mg/100 g). The fatty acid composition of A. gigas showed a higher concentration of unsaturated fatty acids such as linoleic acid (443.9 mg/100 g) and palmitic acid (181.3 mg/100 g) according to gas chromatography. Conclusions : These results showed that Angelica roots can be used in various fields of foods and medicines, and in the preparation of cosmetics.