• 약학회지
• /
• 제49권6호
• /
• pp.443-448
• /
• 2005

Diosgenin (25 (R) - spirost-5-en-3$\beta$ -ol) was oxidized with 2,3-dichloro -5,6-dicyano-1,4-benzoquinone to form 25(R)-1,4,6-spirostatrien-3-one (1) as rigid cyclic $\alpha$,$\beta$-unsaturated carbonyl compound. This compound was reacted with $H_{2}O_{2}$, m-chloroperoxybenzoic acid (mCPBA), NaOCl in the presence with (R,R)- or (S,S)-Jacobsen catalyst, tert-butyl-hydroperoxide (TBHP) in Mo$(CO)_{6}$, and in VO $(acac)_{2}$ catalyst, respectively, 25(R) -1,4,6-spirostatrien -3-one (1) was reduced with $NaBH_{4}$ L-Selectride, $LiAIH_{4}$,$BH_{3}$ $\cdot$$(CH_{3})_{2}S$, Superhydride, Red-Al, and lithium tri-tert-butoxyaluminium hydride. And 25(R)-4,6-spirostadien-3$\beta$-ol (4) was treated with $H_{2}O_{2}$, mCPBA, TBHP in D - (-) - and L-(+)-diisopropyltar-trate and $Ti(OiPr)_{4}$ condition (Sharpless asymmetric epoxidation), TBHP in $Mo(CO)_{6}$, and in $VO(acac)_{2}$ catalyst, respectively.

• 약학회지
• /
• 제51권1호
• /
• pp.56-62
• /
• 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.

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

• 대한약학회:학술대회논문집
• /
• 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.1
• /
• pp.234.1-234.1
• /
• 2003

Spicatoside A and spicatoside B were isolated from Liriopis tuber. Spicatoside A has anticancer activity and it is composed of 1 ${\beta}$-hydroxy diosgenin and trisaccharides. Spicatoside B has the preventive effect of diabetes mellitus and also has 1 ${\beta}$-hydroxy derivatives, which is clevaged the ether linkage of F ring of diosgenin. Therefore, selective synthesis of 1 ${\beta}$-hydroxydiosgenin is required. (omitted)