• YAKHAK HOEJI
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• v.40 no.2
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• pp.163-169
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• 1996

Glycosidation of 20(S)-protopanaxadiol obtained by the alkaline hydrolysis of total ginsenosides with 2,3,4,6-tetra-O-acetyl-${\alpha$-D-glucopyranosyl bromide in the presence of $CdCO_3$ in benzene-dioxane gave a mixture of acetylated monoglucosides and diglucosides in a total yield of 68%. Under the same condenstion condition, 20-dehydroxyglucosides were formed by dehydration of 12-O-glucosides. The structures of produced glycosides were elucidated as 3-O-${\beta$-D-glucopyranosyl-20(S)-protopanaxadiol, 12-O-${\beta$-D-glucopyranosyl-dammar-20(22), 24-dien-$3{\beta},12{\beta}$-diol, 3,12-di-O-${\beta}$-D-glucopyranosyl-dammar-20(22), 24-dien-$3{\beta},\;12{\beta}$-diol, respectively.

• Mycobiology
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• v.36 no.3
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• pp.173-177
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• 2008

The crude ethanol extracts (stem and fruits), their fractions and two triterpenes, $\beta$-Amyrin and 12-Oleanene 3$\beta$, 21$\beta$-diol, isolated as a mixture from the chloroform soluble fraction of an ethanolic extract of Duranta repens stem, were evaluated for antibacterial, antifungal activities by the disc diffusion method and cytotoxicity by brine shrimp lethality bioassay. The structures of the two compounds were confirmed by IR, $^1H$-NMR, $^{13}C$-NMR and LC-MS spectral data. The chloroform soluble fraction of stem and ethanol extract of fruits possess potent antishigellosis activity and also exhibited moderate activity against some pathogenic bacteria and fungi but the isolated compound 1 (mixture of $\beta$-Amyrin and 12-Oleanene 3$\beta$, 21$\beta$-diol) showed mild to moderate inhibitory activity to microbial growth. The minimum inhibitory concentrations (MICs) of the extracts (stem and fruits), their fractions and compound 1 were found to be in the range of 32$\sim$128 ${\mu}g/ml$. The chloroform soluble fractions of stem and ethanol extract of fruit showed significant cytotoxicity with $LC_{50}$ value of 0.94 ${\mu}g/ml$ and 0.49 ${\mu}g/ml$, respectively against brine shrimp larvae.

• Natural Product Sciences
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• v.6 no.2
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• pp.102-105
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• 2000

Chemical investigation of the hot hexane extract of the stem bark of Gordonia dassanayakei afforded a new oleanane triterpenoid, $11{\alpha},13{\beta}-dihydroxyolean-3,12-dione$ (1) and two other oleanane triterpenoids, $3{\beta}-acetoxy-11{\alpha},13{\beta}-dihydroxyolean-12-one\;(2)\;and\;3{\beta},11{\alpha}-diacetoxy-13{\beta}-hydroxyolean-12-one\;(3)\;and\;a\;hopane\;6{\alpha},22-diol$ (4), which are new to the plant.

• YAKHAK HOEJI
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• v.37 no.5
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• pp.437-441
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• 1993

The efficient synthesis of protected $\beta$-hydroxyhomoserine, which is an important intermediate in the synthesis of Mugineic acid, from cis-2-butene-1, 4-diol as a starting material through 12 steps will be reported herein.

• Natural Product Sciences
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• v.14 no.2
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• pp.100-106
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• 2008

Column chromatographic separation of the MeOH extract from the aerial parts of Schizonepeta tenuifolia Briquet led to the isolation of twelve terpenes (1 - 11 and 17), four phenolics (13 - 16) and a hexenyl glucoside (12). Their structures were determined by spectroscopic means to be (-)-pulegone (1), piperitenone (2), p-cymene-3,8-diol (3), schizonepetoside A (4), schizonepetoside C (5), (+)-spatulenol (6), ursolic acid (7), $2{\alpha}$,$3{\alpha}$,$24{\alpha}$,-trihydroxyolean-12en-28oic acid (8), $5{\alpha}$,$8{\alpha}$-epidioxyergosta-6,22-diol-$3{\beta}$-ol (9), stigmast-4-en-3-one (10), ${\beta}-sitosterol$ (11), (Z)-3-hexenyl-1-O-${\beta}$-D-glucopyranoside (12), rosmarinic acid (13), apigenin-7-O-${\beta}$-D-glucopyranoside (14), luteolin-7-O-${\beta}$-D-glucuronopyranoside (15), hesperidin (16) and trans-phytol (17). Compounds 2, 3, 8, 9 and 12 were for the first time isolated from S. tenuifolia Briq.

• Journal of Ginseng Research
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• v.44 no.4
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• pp.619-626
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• 2020

Background: The effects of diol-ginsenoside fraction (Diol-GF) and triol-ginsenoside fraction (Triol-GF) from Korean Red Ginseng on the development of type 1 diabetes (T1D) were examined in diabetes-prone biobreeding (DP-BB) rats that spontaneously develop T1D through an autoimmune process. Methods: DP-BB female rats were treated with Diol-GF or Triol-GF daily from the age of 3-4 weeks up to 11-12 weeks (1 mg/g body weight). Results: Diol-GF delayed the onset, and reduced the incidence, of T1D. Islets of Diol-GF-treated DP-BB rats showed significantly lower insulitis and preserved higher plasma and pancreatic insulin levels. Diol-GF failed to change the proportion of lymphocyte subsets such as T cells, natural killer cells, and macrophages in the spleen and blood. Diol-GF had no effect on the ability of DP-BB rat splenocytes to induce diabetes in recipients. Diol-GF and diol-ginsenoside Rb1 significantly decreased tumor necrosis factor α production, whereas diol-ginsenosides Rb1 and Rd decreased interleukin 1β production in RAW264.7 cells. Furthermore, mixed cytokine- and chemical-induced β-cell cytotoxicity was greatly inhibited by Diol-GF and diol-ginsenosides Rc and Rd in RIN5mF cells. However, nitric oxide production in RAW264.7 cells was unaffected by diol-ginsenosides. Conclusion: Diol-GF, but not Triol-GF, significantly delayed the development of insulitis and T1D in DP-BB rats. The antidiabetogenic action of Diol-GF may result from the decrease in cytokine production and increase in β-cell resistance to cytokine/free radical-induced cytotoxicity.

• Analytical Science and Technology
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• v.12 no.3
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• pp.190-195
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• 1999

The metabolism of testosterone ($17{\beta}$-hydroxy-androst-4-en-3-one) was confirmed in horse after a single intramuscular administration of testosterone cypionate (750 mg). Solvent extracts of urine obtained with enzymatic hydrolysis and methanolysis were analyzed by GC/MS after oxime t-butyldimethylsilyl (oxime-TBDMS) derivatization. The structures of four urinary metabolite after testosterone administration in horse were determined based on EI mass spectra and $5{\alpha}$-androstane-$3{\beta}$, $17{\alpha}$-diol and $5{\alpha}$-androstane-$3{\beta}$-ol-17-one as major was confirmed with authentic standard. Also the concentrations of $5{\alpha}$-androstane-$3{\beta}$, $17{\alpha}$-diol, $5{\alpha}$-androstane-$3{\beta}$, $17{\beta}$-diol, dehydroepiandrosterone (DHEA), $5{\alpha}$-androstane-$3{\beta}$-ol-17-one and testosterone were determined in the urine of normal subjects and the urine after administration. The recovery and detection limit in the most drugs were 86.3~94.7% and 1~3 ppb, respectively. Correlation coefficients for calibration were in the range of 0.984~0.999. Excretion profile of testosterone presents the rapid and large increasement up to maximum values at days 5 after administration and the slow regression. The relative ratios of testosterone, its metabolites over DHEA were determined for indication of testosterone administration in horse doping.

• 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.

• Journal of the Korean Society of Tobacco Science
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• v.31 no.2
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• pp.85-94
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• 2009

This work has been conducted to develop a method for the analysis of neutral volatile flavors and their precursors in tobacco. The neutral volatile compounds and precursors in tobaccos have been investigated by Neutral Volatile scan method(NV scan) using Soxhlet extractor. The method has been used to analyze a range of different tobaccos and tobacco products. Neutral flavor compounds were classified as three sections(1st Volatile Fraction, Breakdown Flavor Products and Cembranoid Precursors). The major components of the First Volatile Fraction were 2-cyclohexene-1-one, 6-methyl-5-hepten-2-one, limonene and phenyl ethanol. The major components of Breakdown Flavor Products were isophorone, solanone, damascenone, 3-hydroxy-$\beta$-damascone, geranyl acetone, $\beta$-ionone, dihydroactinidiolide, norsolanadione, neophytadiene, hexahydrofarnesylacetone, farnesyl acetone and megastigmatrienone. The major cembranoid precursor compounds were dibutyl phthalate, duvatrenediols, 8,12-epoxy-14-labden-13-ol, 11-hydroperoxy-2,7,12(20)-cembratriene-4,6-diol, 12,15-epoxy-12,14-labadien-8-ol, 2,7,11-cembratrien-4,6-diol and 8,13-epoxy-14-labdien-12-ol. The NV scna results of tobacco types(flue-cured, burley and oriental) showed that each tobacco type has a characteristic flavor component profile.

• Bulletin of the Korean Chemical Society
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• v.23 no.12
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• pp.1693-1694
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• 2002