• YAKHAK HOEJI
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• v.29 no.2
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• pp.62-69
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• 1985

The isomeric intermediates, $3{\alpha}$and $3{\beta}-amino-5{\alpha}-cholestane required for the synthesis of N-nitrosoureas, N-(2-chloroethyl)-N-nitrosocarbamoyl-$3{\alpha}-amino-5{\alpha}$-cholestane (9), N-methyl-N-nitrosocarbamoyl-3${\alpha}-amino-5{\alpha}-cholestane$ (10), N-(2-chloroethyl)-N-nitrosocarbamoyl-$3{\beta}-amino-5{\alpha}-cholestane$: (7), and N-methyl-N-nitrosocarbamoyl-$3{\beta}-amino-5{\alpha}-cholestane$ (8) were obtained through the $LiAlH_{4}$ reduction of $5{\alpha}$-cholestan-3-one oxime, followed by the chromatographic separation: the assignment of the stereochemistry of both isomers were based on the shape and chemical shift of $C_{3}$-proton resonances on their NMR spectra and on the elution mobility on the TLC. The urea intermediates, N-(2-chloroethyl) carbamoyl-3.alpha.-amino-5.alpha.-cholestane (13), N-methylcarbamoyl-$3{\alpha}-amino-5{\alpha}-cholestane$ (14), N-(2-chloroethyl) carbamoyl-$3{\beta}-amino-5{\alpha}-cholestane (11) and N-methyl-$3{\beta}-amino-5{\alpha}$-cholestane (12) were prepared by the treatment of each isomers ($3{\alpha}$-amino-and $3{\beta}-amino-5{\alpha}$-cholestane) with alkyl isocyanates in anhydrous $CHCl_{3}$, and the corresponding nitrosoureas, 7-10 were obtained by the nitrosation of the ureas, 11-14, with AcOH (or HCOOH)/$NaNO_{2}$ in ice-cold condition. The inhibitory activity of the nitrosoureas, 7-10, and their intermediates, 12-14 towards the growth of L1210 murine leukemia cells, were examined. Among them, the compounds 9 and 10 exhibited high activity having $ED_{50}$ to be 5.5g/ml and 6.1g/ml, respectively.

• YAKHAK HOEJI
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• v.7 no.2_3
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• pp.72-74
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• 1963

Synthesis of azosteroid 3-aza-A-homo-cholestane-4-one, 3-aza-A-homo-coprostane-4-one and 3-aza-A-homo-cholestane-4-one from corresponding oxim and keto-steroid by means of Beckmann's and Schimdt's rearrangement by perphosphoric acid have been evaluated.

• Natural Product Sciences
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• v.17 no.3
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• pp.183-188
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• 2011

A bisdesmosidic cholestane glycoside was isolated from the rhizomes of Polygonatum sibiricum and the structure was elucidated by spectroscopic methods and acid hydrolysis as (22S)-cholest-5-ene-$1{\beta}$,$3{\beta}$,$16{\beta}$,22-tetrol 1-O-${\alpha}$-L-rhamnopyranosyl 16-O-${\beta}$-D-glucopyranoside. This compound exhibited weak cytotoxic activity with the $IC_{50}$ value, $63.6\;{\mu}M$ in human MCF-7 breast cancer line, whereas it failed to show agonistic activity at $100{\mu}M$ in TGR5 assay with Chinese hamster ovary (CHO) cells. This is the first report of a bisdesmosidic cholestane glycoside from Polygonatum species and the full assignments of $^1H$, $^{13}C$ NMR by HMBC, TOCSY and NOESY experiments were provided.

• Archives of Pharmacal Research
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• v.9 no.4
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• pp.215-217
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• 1986

Steroidal nitrosoureas have been synthesized and their antitumor activity on L 1210 cells was evaluated, N-(2-Chloroethyl)-N-nitrosocarbamoyl-3-aza-A-homo-5$\alpha$-cholestane (5a) showed significantly low $ED_{50}$ value of 1.6 $\nu$g/ml whose activity is equivalent to that of methyl-CCNU ($ED_{50}$ = 1.7 mg/ml).

• Bulletin of the Korean Chemical Society
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• v.32 no.spc8
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• pp.2933-2937
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• 2011

A new highly selective receptor (3) based on an acridine-imidazolium functionalized cholestane for anion sensing was designed and synthesized. A binding study of 3 with various anions was assessed by UV-vis and fluorescence spectroscopies in dry CH3CN. Receptor 3 showed the highest selectivity toward hydrogen pyrophosphate (Ka = $1.5{\times}10^4M^{-1}$).

• Bulletin of the Korean Chemical Society
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• v.14 no.2
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• pp.176-178
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• 1993

A series of 4-(2-chloroethyl)nitrosocarbamoyl- and 4-methyl nitrosocarbamoyl analogs of 4-Aza-$5{\alpha}$-cholestane (5a and 5b), 4-Aza-5-cholestene (6a and 6b) were synthesized and evaluated for their inhibitory activity against the Sarcoma 180 cell. The steroidal nitrosoureas, 5a, 5b, 6a and 6b displayed modest activity in vitro.

• Bulletin of the Korean Chemical Society
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• v.14 no.1
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• pp.156-158
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• 1993

• YAKHAK HOEJI
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• v.51 no.6
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• pp.495-499
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• 2007

Seven epoxy- and hydroxyandrostane derivatives ($DH-1{\sim}DH-7$) and nine epoxy- and hydroxycholestane derivatives ($CH-1{\sim}CH-9$) with unsaturation in ring A and ring B were synthesized from DHEA and cholesterol, respectively. The antinociceptive effects of all synthesized compounds were measured by hot plate method. Most of androstane derivatives except $1{\alpha},2{\alpha}$-epoxy-4,6-androstadiene-3,17-dione (DH-3), and CH-6, CH-7 and CH-9 exhibited antinociceptive effect. 1,4-Androstadiene-$3{\beta},17{\beta}$-diol (DH-5, 100 mg/kg, $35.8{\pm}7.39$), $6{\alpha},7{\alpha}$-epoxy-1,4-androstadiene-3,17-dione (DH-4, 100 mg/kg, $32.6{\pm}5.50$) and $5{\alpha},6{\alpha}$-epoxy-17-oxo-androstan-$3{\beta}$-ol (DH-1, 100 mg/kg, $32.5{\pm}2.98$) were more effective than morphine (10 mg/kg, $30.6{\pm}0.5$). The analgesic effects of androstane derivatives on acetic acid writhing in mice were lower than aspirin. The androstane derivatives were less effective than ibuprofen at inhibiting effects on the carrageenin induced paw oedema. 4,6-Cholestadien-$3{\beta}$-ol (CH-5), $1{\alpha},2{\alpha}$-epoxy-4,6-cholestadien-$3{\beta}$-ol (CH-7) and $7{\alpha}$-hydroxy4-cholesten-3-one (CH-9) showed the decrease of serum triglyceride and total cholesterol levels in poloxamer P-407 injected rat.

• Journal of the Society of Cosmetic Scientists of Korea
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• v.44 no.4
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• pp.389-397
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• 2018

The starfish, Asterina pectinifera Muller and Troschel (Asterinidae) is an indigenous species commonly found in all coasts of Korea causes damages to shellfish farms. In order to exterminate A. pectinifera, they are dried and used as fertilizer. Although various studies have been conducted to create high added value from the retrieved A. pectinifera, their actual utilization is relatively low. Accordingly, this study aimed to find new practical uses of starfish by identifying useful ingredients for skin anti-aging. Two polyhydroxysteroids and one asterosaponin were isolated from the A. pectinifera. The structures of these compounds were identified as $5{\alpha}$-cholestane-$3{\beta},6{\alpha},7{\alpha},8,15{\alpha},16{\beta},26$-heptol, $5{\alpha}$-cholestane-$3{\beta},4{\beta},6{\alpha},7{\alpha},8,15{\beta},16{\beta},2$6-octol, and asterosaponin $P_1$ on the basis of chemical and spectroscopic analysis. Among these compounds, we have found that asterosaponin $P_1$ increased epidermal stem cell proliferation and the expression of hyaluronan synthase-2 and hyaluronan synthase-3 gene, which are enzymes that synthesize water-binding matrix hyaluronic acids in keratinocytes. In addition, asterosaponin $P_1$ increased synthesis of pro-collagen type I, a major dermal collagen in fibroblasts. As a result, asterosaponin $P_1$ isolated from A. pectinifera could be used as a useful cosmetic ingredient that improves skin symptoms accompanying skin aging.

• Preventive Nutrition and Food Science
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• v.1 no.2
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• pp.196-202
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• 1996

The effect of cooking(boiling, steaming and baking0and drying on the cholesterol content and formation of oxidized cholesterols in quid(Japanese flying squid, Todarodes pacificus) was studied. Cholesterol content of live squid meat varied with the portion sampled, and results from spectrophotometric assay ranged from 263.2mg/1..g(mantle) to 315.8mg/100g(tentacle). The cholesterol levels analyzed by gas chromatography(GC) for squid samples were lower by 7% of total cholesterol for live squid meat and 24% for processed meat than those results by spectrophotometric assay. Cooking resulted in the decrease of the initial total cholesterol content of raw meat from 10%(boiling for 5min.) to 25%(steaming for 5min.) The amounts of cholesterol remaining after baking were 68% for microwave oven samples and 64% for convection oven samples. Drying of raw tissue caused the greater reduction in cholesterol content than cooking but showed no significant difference in samples stored for 6 weeks at 4$^{\circ}C$ and 2$0^{\circ}C$. Raw squid meats contained essentially no oxidized cholesterols, while the 22-hydroxychoesterol was detected in frozen meats. The additional oxidized cholesterols as cholestane-triol was indentified with 22-hydroxycholesterols in cooked samples. Sun dried meat stored at 4一 and 2$0^{\circ}C$ for 6 weeks had the three kinds of oxidized cholesterols such as 22-hydroxycholesterol, cholesta-3,5-dien-7-one and cholestane-triol.