• Journal of Microbiology and Biotechnology
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• v.32 no.8
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• pp.976-981
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• 2022

Phenanthrenes are bioactive phenolic compounds found in genus Dioscorea, in which they are distributed more in peel than in flesh. Recent studies on phenanthrenes from Dioscorea sp. peels have revealed the potential for valuable biomaterials. Herein, an analytical method using high-performance liquid chromatography (HPLC) for quantitation of bioactive phenanthrenes was developed and validated. The calibration curves were obtained using the phenanthrenes (1-3) previously isolated from Dioscorea batatas concentrations in the range of 0.625-20.00 ㎍/ml with a satisfactory coefficient of determination (R²) of 0.999. The limit of detection (LOD) and the limit of quantification (LOQ) values of the isolated phenanthrenes ranged from 0.78-0.89 and 2.38-2.71 ㎍/ml, respectively. The intraday and interday precision ranged from 0.25-7.58%. The recoveries of the isolated phenanthrenes were from 95 to 100% at concentrations of 1.25, 2.5, and 5.0 ㎍/ml. Additionally, phenanthrenes (1-3) were found in all investigated peel extracts. Hence, the developed method was encouraging for the quantitative analysis of phenanthrenes in genus Dioscorea.

• Bulletin of the Korean Chemical Society
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• v.17 no.7
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• pp.577-579
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• 1996

• Natural Product Sciences
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• v.13 no.4
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• pp.378-383
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• 2007

Phenathrene derivatives, such as batatasins, are well-known constituents in Dioscorea Rhizoma. Although phenanthrenes have been reported as representative compounds in this plant, standard markers for quality control have been focused on the polar constituents (saponins and purine derivatives). Herein, simple, rapid and reliable HPLC method was developed to determine 3,5-dimethoxyphenanthrene-2,7-diol (DMP) and batatasin-I (BA-I) as non-polar standard maker compounds of Dioscorea Rhizoma. DMP and BA-I were analyzed under optimized HPLC conditions [column: Columbus $5{\mu}$ C18 100A ($30{\times}4.6mm$ i.d., $5{\mu}m$; mobile phase: $H_2O$ with 0.025% $CH_3COOH$ (v/v) for solvent A and $CH_3CN$ with 0.025% $CH_3COOH$ (v/v) for solvent B, gradient elution; flow rate: 2 mL/min; detection: 260 nm), and each experiment was finished within 13 min. Good linearity was achieved in the range from 0.5 to $10.0{\mu}g/mL$ for each compound, and intra- and inter-day precision were in the acceptable levels. The recovery test were performed with three different Dioscorea Rhizoma samples (D. opposita, D. batatas and D. japonica), and showed its accuracy values in the range of 97.2 - 102.8% for three different concentrations of DMP and BA-I. The content levels of DMP and BA-I were ranged under 0.0020%. These results demonstrated that amounts of DMP and BA-I are easily determined with conventional HPLC-UV-DAD method although the content levels were lower than those of saponins and allantoin in Dioscorea Rhizoma. This HPLC method could be used for quality control of various Dioscorea preparations.

• Natural Product Sciences
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• v.20 no.2
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• pp.91-94
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• 2014

Column chromatographic separation of the MeOH extract from the tubers of Bletilla striata yielded seven phenolic components including four phenanthrenes, 3,7-dihydroxy-2,4-dimethoxyphenanthrene (1), 3,7-dihydroxy-2,4,8-trimethoxyphenanthrene (2), 9,10-dihydro-4,7-dimethoxyphenanthrene-2,8-diol (3), and 9,10-dihydro-1-(4'-hydroxybenzyl)-4,7-dimethoxyphenanthrene-2,8-diol (4) and three stilbenes, gigantol (5), 3',4"-dihydroxy-5',3",5"-trimethoxybibenzyl (6), and batatasin III (7). Their structures were determined on the basis of NMR spectroscopic data. Among them, compound 2, 3, and 6 were reported for the first time from this plant. The isolated compounds (1-7) were tested for cytotoxicity against four human tumor cell lines in vitro using a Sulforhodamin B bioassay.

• Bulletin of the Korean Chemical Society
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• v.23 no.9
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• pp.1213-1221
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• 2002

Friedel-Crafts alkylation reaction of an isomeric mixture of 1,2,3,4,5,6,7,8- (2) and 1,2,3,4,5,6,7,8-octahydrophenanthrene (2') with excess vinylchlorosilanes such as vinyl(methyl)dichlorosilane (1a) and vinyltrichlorosilane (1b) in the presence of aluminum chloride catalyst at 80 $^{\circ}C$ gives only one dialkylated products, 9,10-bis[2-(chlorosilyl)ethyl]-1,2,3,4,5,6,7,8-octahydroanthrenes [(Cl2XSiCH2CH2)2C14H16: X = Me (4a), Cl (4b)] in good yields, but 9,10-bis[2-(chlorosilyl)ethyl]-1,2,3,4,5,6,7,8-octahydrophenanthrenes are not obtained. However, monoalkylation of 2 with 1 affords a mixture of both isomeric compounds, 9-[2-(chlorosilyl)ethyl]-1,2,3,4,5,6,7,8-octahydroanthracenes 3 and -phenanthrenes 3'. The yield of product 3' is always higher than that of 3. When a mixture of 3 and 3' is alkylated again with 1, only product 4 without phenanthrene type compounds is obtained, indicating that the isomerizations between 2 and 2', or 3 and 3'occur under the alkylation condition. The alkylation with dimethylvinylchlorosilane or trimethylvinylsilane did not proceed. The structure of 4a is determined by X-ray single crystal diffraction analysis.

• Korean Journal of Pharmacognosy
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• v.40 no.4
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• pp.257-279
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• 2009

Plants of genus Dioscorea have long been served as important carbohydrate-stuffed foods in the tropical and subtropical regions, and utilized as traditional herb medicines to enhance digestive function, improve anorexia, and treat diarrhea in oriental countries. It is known that around 600 species of Dioscorea are distributed in the world including 107 species in Asia, but actually utilized Dioscorea species are restricted to small numbers. Phytochemical investigations for Dioscorea species have revealed a number of chemical components such as sapogenins, saponins, phenanthrenes, stilbenes, diterpenes and purine derivatives. According to recent pharmacological studies, Dioscorea species possess significant antioxidant, antibacterial and anti-inflammatory activities as well as anticancer, antidiabetic, cholesterol-lowering and hypolipidemic effects. Here, seven Dioscorea species (D. batatas, D. japonica, D. bulbifera, D. opposita, D. tokoro, D. nipponica and D. alata), mainly distributed and used in Korea, China, and Japan, are reviewed to provide their botanical, phytochemical and pharmacological properties were described.

• Ecology and Resilient Infrastructure
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• v.2 no.2
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• pp.177-184
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• 2015

This study assessed the performance of activated carbon (AC) amendment to treat polycyclic aromatic hydrocarbons (PAHs) including both parent- and alkylated-moieties in sediment impacted by diesel. A field-collected, diesel-impacted sediment with a NAPL content of 1% was used for the study. No. 2 diesel fuel is weathered by heating at $70^{\circ}C$ for 4 days to obtain a weathered diesel sample having C3-naphthalenes to C2-phenanthrenes/anthracenes (N2/P3) ratio similar to the original sediment. The sediment samples spiked with the weathered diesel to obtain non-aqueous phase liquid (NAPL) contents of 1, 5 and 10% were contacted with AC with a dose of 5% as sediment dry weight for 1 month. By the AC-sediment contact, the freely-dissolved equilibrium concentrations were substantially reduced. Even for sediment with 10% NAPL content, the reductions in the freely-dissolved concentrations were 92% and 75% for total parent-and alkylated-PAHs, respectively. The effect of NAPL contents on the performance of AC was negligible for parent-PAHs, while for alkylated-PAHs, a slightly reduced AC performance was observed. The results suggest that the AC amendment can be an effective option for the treatment of petroleum-impacted sediment with relatively high NAPL contents.

• Proceedings of the Plant Resources Society of Korea Conference
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• 2023.04a
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• pp.18-18
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• 2023

Two new phenanthrenes, namely, (1R,2R)-1,7-hydroxy-2,8-methoxy-2,3-dihydrophenanthrene-4(1H)-one (1) and 2,7-dihydroxyphenanthrene-1,4-dione (2), were isolated from the ethyl acetate-soluble fraction of Dendrobii Herba, together with the eleven known compounds, densiflorol B (3), 6,7-dimethoxyphenanthrene2,5-diol (4), dehydroorchinol (5), 1,5,7-trimethoxy-2-phenanthrenol (6), denthyrsinin (7), ephemerantol A (8), lusianthridin (9), moscatilin (10), gigantol (11), 3-[(1E)-2-(3-hydroxyphenyl)ethenyl]-5-methoxyphenol (12) and (-)-syringaresinol (13). Structures of 1 and 2 were elucidated by analyzing 1D and 2D NMR as well as HR-ESI-MS data. The absolute configuration of compound 1 was confirmed by ECD spectroscopic method. In cytotoxicity evaluation using FaDu human hypopharyngeal squamous carcinoma cell line, compounds 3-6, 8, 10 and 12 showed activities, with IC₅₀ values ranging from 2.55 to 17.70 μM. Among them, compound 10 exhibited remarkable cytotoxic activity with IC₅₀ value of 2.55 μM. This is the first report on the anticancer mechanistic study of compound 10 in HNSCC including FaDu cells.

• The Korean Journal of Malacology
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• v.30 no.4
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• pp.371-381
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• 2014

The bioaccumulation of 16 United States Environmental Protection Agency (USEPA) priority polycyclic aromatic hydrocarbons (PAHs) and alkylated PAHs in the Manila clam, Ruditapes philippinarum exposed to sediments artificially contaminated by Iranian Heavy Crude Oil was measured and the biota-sediment accumulation factor (BSAF) was estimated through laboratory experiments. The proportion of 16 PAHs accumulated in the tissue of R. philippinarum was only from 3 to 7% of total PAHs. Among 16 PAHs, the concentration of naphthalene was highest in the tissue. Alkylated PAHs were highly accumulated more than 93% of total PAHs. The C3 dibenzothiophene was most highly accumulated. The relative composition of alkylated naphthalenes in the tissue of R. philippinarum was lower than in the sediments. In contrast, those of alkylated compounds of fluorenes, phenanthrenes, dibenzothiophenes were higher in the tissue than the sediments. The BSAF for sum of 16 PAHs was 0.11 to 0.13 g carbon/g lipid and that for alkylated PAHs was 0.05 to 0.06 g carbon/g lipid. Naphthalene showed the highest BSAF value. Alkylated PAHs with the same parent compound, BSAF tended to increase with the number of alkylated branch increased, except for alkylated chrysenes. BSAF of total PAHs lies between that of field-based values, and are also similar to those of other persistent organic pollutants (PCBs, DDTs, HCHs). This study provides the BSAF values of individual alkylated PAHs accumulated in R. philippinarum for the first time and will be used as a basis for further understanding the bioaccumulation of organic contaminants in the marine benthic organisms.

• Journal of Life Science
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• v.16 no.4
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• pp.647-652
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• 2006

Plants of the genus Dioscorea have long been used as oriental folk medicine, and Dioscorea batatas Decne has been cultivated for healthy food in Korea. Although the bulbils were produced 2,000 ton annually, there are few reports for bioactive compounds in bulbils. In this study, three phenanthrenes and two phenanthraquinones were isolated from the aerial bulbils of D. batatas Decne, and their structures were elucidated. Among them, compound 2 (6-hydroxy-2,7-dimethoxy-1,4-phenanthraquinone) has not been reported previously. Evaluation of antimicrobial activities based on disk-diffusion assay, MIC and MFC showed the compound 12 (6,7-dihydroxy-2,4-dimethoxyphenanthrene) has strong antimicrobial activity with $25\;{\mu}g/ml$ of MIC and MFC against Candida albicans. Our results suggested that compound 12 has a potent antifungal activity, and the antimicrobial activity and its spectrum are modulated by hydroxylation and methoxylation of phenanthrene ring moiety of the compound.