• 약학회지
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• 제58권5호
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• pp.337-342
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• 2014

The present study was undertaken to investigate the influence of diosgenin on vascular smooth muscle contractility and to determine the mechanism involved. We hypothesized that diosgenin, the primary ingredient of Dioscorea villosa, plays a role in vascular relaxation through inhibition of Rho-kinase in rat aortae. Denuded arterial rings from male Sprague-Dawley rats were used and isometric tensions were recorded using a computerized data acquisition system. Interestingly, diosgenin inhibited fluoride-induced contraction but didn't inhibit phorbol ester-induced contraction suggesting that additional pathways different from endothelial nitric oxide synthesis such as inhibition of Rho-kinase might be involved in the vasorelaxation. Furthermore, diosgenin didn't inhibit thromboxane $A_2$-induced increases in pERK1/2 levels suggesting the mechanism excluding inhibition of thromboxane $A_2$-induced increases in ERK1/2 phosphorylation. This study provides evidence that diosgenin induces vascular relaxation through inhibition of Rho-kinase in rat aortae.

• 생약학회지
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• 제46권3호
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• pp.189-194
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• 2015

Validation and contents determination of (+)-catechin and diosgenin from Smilax china L. rhizome (SC) were confirmed using Ultra-Performance Liquid Chromatography (UPLC). (+)-Catechin was isolated from 60% prethanol SC extract and diosgenin was isolated by acid hydrolysis of saponin fraction from 60% prethanol extract of SC. Finally we have established the validation of the isolated compounds [(+)-catechin, diosgenin] and contents determinations of (+)-catechin and diosgenin by UPLC on 60% prethanol extract of SC [(+)-catechin: 0.06878%, diosgenin: 0.48169%], and on hot water extract of SC [(+)-catechin: 0.06584%, diosgenin: 0.42178%].

• 한국식품영양과학회지
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• 제22권3호
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• pp.313-316
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• 1993

파 지하부로부터 분리된 2종의 diosgenin 배당체의 구조를 그의 분광학적 data와 화학적 실험 등의 방법으로 결정하였다. 그 결과, 이 두화합물의 구조는 diosgenin 3-O-$\alpha$-L-rhamnopyranosyl (1$\longrightarrow$2)-[$\alpha$-L-rhamnopyranosyl (1$\longrightarrow$4)]-$\beta$-D-glucopyranoside (1, dioscin)과 diosgenin 3-O-$\alpha$-L-rhamnopyranosyl (1$\longrightarrow$4)-$\alpha$-L-rhamnopyranosyl (1$\longrightarrow$4)]- [$\alpha$-L-rhamnopyranosyl (1$\longrightarrow$2]-$\beta$-D-glucopyranoside (2, saponin P-d)로서 기지 물질이나, saponin P-d를 부분가수분해하여 얻은 prosapogenin 중 compound 4는 문헌 미기재의 물질이다.

• Asian Pacific Journal of Cancer Prevention
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• 제14권11호
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• pp.6945-6948
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• 2013

Background: Diosgenin, a steroidal saponin from a therapeutic herb, fenugreek (Trigonellafoenum-graceum L.), has been recognized to have anticancer properties. Telomerase activity is not detected in typical healthy cells, while in cancer cell telomerase expression is reactivated, therefore providing a promising cancer therapeutic target. Materials and Methods: We studied the inhibitory effect of diosgenin on human telomerase reverse transcriptase gene (hTERT) expression which is critical for telomerase activity. MTT- assays and qRT-PCR analysis were conducted to assess cytotoxicity and hTERT gene expression inhibition effects, respectively. Results: MTT results showed that $IC_{50}$ values for 24, 48 and 72h after treatment were 47, 44 and $43{\mu}M$, respectively. Culturing cells with diosgenin treatment caused down-regulation of hTERT expression. Discussion: These results show that diosgenin inhibits telomerase activity by down-regulation of hTERT gene expression in the A549 lung cancer cell line.

• 대한화학회지
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• 제30권4호
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• pp.369-376
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• 1986

모세관 기체-액체프로마토그래피(GLC)에 의해 인도네시아산 Costus speciosus중의 diosgenin을 정량하기 위해 가수분해 및 추출, 아세틸화 반응 및 GLC의 측정 조건등을 검토하였다. 건조된 diosgenin분말 1.20g을 3N HCI과 xylene의 혼합용액으로 95∼100${\circ}C$에서 4시간 환류시킨 다음 xylene층을 분리하였다. Xylene을 증발시켜 날려보내고 20:80의 acetic anhydride-pyridine을 가하고 30분간 환류시켜 아세틸화시킨 후 diethyl ether로 추출하였다. 무수 $Na_2SO_4$로 탈수시키고 ether를 날려 보낸 다음 찌끼를 n-hexane 5.00ml에 녹여 GLC로 분석하였다. SE-30 25m ${\times}$ 0. 33mm의 모세관을 사용하였고 컬럼온도는 180${\circ}$에서 270${\circ}C$까지 10${\circ}C$/min의 속도로 온도를 상승시켰다. 운반기체 $N_2$의 유속은 2ml/min이었고 FID로 검출하였다. Diosgenin의 분석결과는 0.281%이었고, 상대표준편차는 1.8%로서 재현성이 좋았다.

• 대한약학회:학술대회논문집
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• 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.1
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• pp.233.2-233.2
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• 2003

Diosgenin(25(R)-spirost-5-en-3${\beta}$-ol) is the steroid saponin, was isolated from Mexican yam(Oioscorea). Estrogenic, progesterogenic and anti-inflammatory effects of diosgenin has been hypothesized due to its structural similarity to estrogen, progesterone precursors. And diosgenin had been reported to lower serum cholesterol in chicken and rabbits fed cholesterol and to decrease liver cholesterol in cholesterol-fed rats. (omitted)

• 약학회지
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• 제51권1호
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• pp.56-62
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• 2007

Twelve epoxy and hydroxydiosgenin derivatives (DI-1${\sim}$DI-12) were synthesized from diosgenin (25(R)-5-spirosten-3${\beta}$-ol). Diosgenin was epoxidized with m-chloroperoxybenzoic acid (mCPBA) to oxidize 25(R)-4${\alpha}$,5${\alpha}$-epoxyspirostane (DI-1). Diosgenin was reacted with DDQ to form 25(R)-1,4,6-spirostatrien-3-one (DI-2), which was treated with 30% H$_2$O$_2$ to give 25(R)-1${\alpha}$,2${\alpha}$-epoxy-4,6-spirostadien-3-one (DI-3) and treated with mCPBA to form 25(R)-6${\alpha}$,7${\alpha}$-epoxy-1,4-spirostadien-3-one (DI-7), respectively. DI-3 was reduced with NaBH$_4$ to afford 25(R) -1${\alpha}$,2 ${\alpha}$-epoxy-4,6-spirostadien-3${\beta}$-ol(DI-4) and reacted with Li metal in absolute ethanol to form 25(R)-2-ethoxy-1,4,6-spirostatrien-3-one (DI-5). DI-7 was reduced with NaBH$_4$ to produce 25(R)-3${\beta}$,7${\alpha}$-dihydroxy-4-spirostene (DI-8) and treated with Li metal in liquid ammonia to produce 25(R)-7${\alpha}$-hydroxy-4-spirosten-3-one (DI-9). DI-2 was reduced with NaBH$_4$ to form 25(R) -4,6-spirestadien-3${\beta}$-ol(DI-10), which was stirred with 30% H$_2$O$_2$ to synthesize 25(R)-4,6-spirostadien-3-one (DI-11) and reacted with mCPBA to give 25(R)-4${\beta}$,5${\beta}$ -epoxy-6-spirosten-3${\beta}$-ol (DI-12), respectively. The antinociceptive effects of synthesiz ed compounds were measured by hot plate method and compound DI-7 signifcantly exhibited antinociceptive effect. DI-2 decreased the serum triglyceride and total cholesterol levels in poloxamer P-407 injected rat.

• 한국식품영양학회지
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• 제22권2호
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• pp.223-228
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• 2009

The principal objective of this study was to determine the available components in different varieties of Discorea spp. The Discorea spp. samples were divided into three groups by variety. The three groups were divided into Jangma(D. batatas Decaisne), Danma(D. japonica Decaisne), and Doonggunma(D. opposita Thumb), and then assessed with regard to the content of proximate compositions, minerals, sugars, crude saponin, and diosgenin. No substantial differences were noted to exist among samples in terms of carbohydrate and crude protein contents. The crude lipid contents were detected in the following order : Danma(D. japonica Decaisne, $0.71{\pm}0.15%$) > Jangma(D. batatas Decaisne, $0.65{\pm}10.12%$) > Doonggunma (D. opposita Thumb, $0.49{\pm}0.10%$). The Danma(D. japonica Decaisne) samples were determined to harbor the highest K($2.07{\pm}0.91%$), Ca($0.21{\pm}0.12%$), Fe($110.7{\pm}0.0$ mg/kg), Mn($20.6{\pm}3.4$ mg/kg) and Zn($31.2{\pm}3.9$ mg/kg) contents among all tested samples. The predominant sugar components in all samples were mannose($70.7{\pm}1.3{\sim}80.5{\pm}1.5%$), glucose($18.2{\pm}1.2{\sim}28.3{\pm}2.5%$) and sucrose($60.3{\pm}3.7{\sim}83.6{\pm}6.5%$). The crude saponin and diosgenin contents for Jangma(D. batatas Decaisne), Danma(D. japonica Decaisne) and Doonggunma(D. opposita Thumb) varieties were : $1.7{\pm}0.4%$, $3.9{\pm}0.8%$ and $3.2{\pm}0.7%$, and $13.59{\pm}1.74$ mg/g, $14.25{\pm}1.60$ mg/g and $18.00{\pm}1.92$ mg/g, respectively.

• 한국식품영양학회지
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• 제22권3호
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• pp.449-455
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• 2009

The principal objective of this study was to determine the quality and potential of DHEA formation after the addition of diosgenin of yam(Dioscorea spp.) during the fermentation of soybean paste. All samples were divided into three groups based on the variety of yam. In sample A, the soy source was not separated from soybean paste and in sample B, the soybean source was separated from soybean paste. The range in salt concentration in the samples was as follows : sample A: 10.5~11.8%, samples B: 7.9~8.8%. However, no substantial differences between the two samples, in terms of salt content, were observed. The crude protein and crude lipid content were found to decrease with the fermentation time of soybean paste(passage of 30 days: 26.4~32.3% and 4.45~5.90%, passage of 60 days: 24.5~28.5% and 3.95~4.90%, respectively). As the fermentation time of soybean paste increased, the nitrogen from amino compounds increased(passage of 30 days: 531.9~687.7 mg%, passage of 60 days: 551.3~706.8 mg%). In regards to color and preference, sample B, where the soy source was separated from soybean paste, was better than sample A, where the two components were not separated. After a soybean paste fermentation time of 60 days, the diosgenin of yam, which was added to the soybean paste, was not detected in tested samples, and the contents of DHEA formation in soybean paste were as follows: sample A: $488.0\pm42.5{\sim}719.3\pm44.8{\mu}g/g$, sample B: $287.3\pm20.6{\sim}482.7{\pm}36.5{\mu}g/g$.

• Plant Biotechnology Reports
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• 제3권3호
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• pp.243-250
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• 2009

In the present study, a simple one medium formulation protocol for callus culture, somatic embryogenesis and in vitro production of ${\beta}-carboline$ alkaloids and diosgenin in Tribulus terrestris L. was developed. Extensive callus induction and proliferation was obtained in leaf explant on Murashige and Skoog (MS) medium supplemented with $5.0{\mu}M$ 6 benzyl adenine (BA) and $2.5{\mu}M$ ${\alpha}-naphthaleneacetic$ acid (NAA). The embryogenic callus was maintained on subculture to fresh parental medium at 4-week intervals over a period of 28 months. The frequency of embryo formation was at a maximum ($18.1{\pm}0.9$ per g of callus) on MS medium containing $5.0{\mu}M$ BA and $2.5{\mu}M$ NAA together with $75mg\;1^{-1}$ casein hydrolysate. Globular embryo developed into torpedo stage embryo under the influence of starvation. The accumulation of ${\beta}-carboline$ alkaloids (harmaline and harmine) and steroidal saponin (diosgenin) in non-embryogenic and embryogenic callus culture derived from leaf explant was compared with root, leaf, stem, and fruit of the mother plant. The embryogenic callus accumulated equivalent amounts of harmaline ($66.4{\pm}0.5{\mu}g/g$ dry weight), harmine ($82.7{\pm}0.6{\mu}g/g$ dry weight), and diosgenin ($170.7{\pm}1.0{\mu}g/g$ dry weight) to that of the fruit of T. terrestris. The embryogenic callus culture of this species might offer a potential source for production of important pharmaceuticals.