• 약학회지
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• 제29권2호
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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.

• 약학회지
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• 제7권2_3호
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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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• 제17권3호
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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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• 제9권4호
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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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• 제32권spc8호
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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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• 제14권2호
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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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• 제14권1호
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• pp.156-158
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• 1993

• 약학회지
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• 제51권6호
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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.

• 대한화장품학회지
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• 제44권4호
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• pp.389-397
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• 2018

별불가사리(Asterina pectinifera Muller and Troschel)는 우리나라 전국 연안에서 흔히 볼 수 있는 토속종으로, 패류 양식장에 피해를 주는 불가사리류 중의 하나이다. 별불가사리 퇴치를 위해 대부분 건조하여 비료로 활용하고 있으며, 고부가가치 창출을 위한 다양한 연구가 진행되었으나 실제 활용은 미미한 실정이다. 따라서, 별불가사리로부터 피부 유용성분을 밝혀 새로운 활용 방안을 모색하고자 하였다. 성분연구를 통해 별불가사리로 부터 2종의 polyhydroxysteroid와 1종의 saponin을 분리하였으며, 이의 구조를 각각 $5{\alpha}$-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 및 asterosaponin $P_1$으로 동정하였다. 이 물질들의 피부 효능을 확인한 결과 asterosaponin $P_1$이 표피 줄기세포의 증식을 촉진시키고, 각질형성세포에서 히알루론산을 합성하는 효소인 hyaluronan synthase-2와 hyaluronan synthase-3 유전자의 발현을 증가시킴을 확인하였다. 또한, asterosaponin $P_1$은 섬유아세포에서 진피의 주요 콜라겐인 type 1 콜라겐의 생합성을 촉진하는 효능을 보였다. 이상의 결과들로부터, 별불가사리로부터 분리한 asterosaponin $P_1$은 노화에 동반되는 피부 증상을 개선하는 항노화 화장품 소재로 활용될 수 있을 것으로 판단된다.

• Preventive Nutrition and Food Science
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• 제1권2호
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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.