(25S)-5α-spirostane-2α,3β-diol | 6811-13-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (25S)-5α-spirostane-2α,3β-diol
• 英文别名: (25S)-5α-spirostan-2α,3β-diol；5α,25S-spirostan-2α,3β-diol；Neogitogenin；(1R,2S,4S,5'S,6R,7S,8R,9S,12S,13S,15R,16R,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-15,16-diol
• CAS: 6811-13-8
• 化学式: C₂₇H₄₄O₄
• 分子量: 432.644
• InChiKey: FWCXELAAYFYCSR-HJXRQQMRSA-N

物化性质

• 熔点：
  248 °C
• 沸点：
  534.2±35.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  31
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (25S)-5α-spirostane-2α,3β-diol 生成 [(1R,2S,4S,5'S,6S,7S,8S,9S,12S,13S,15R,16R,18S)-15-acetyloxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl] acetate
  参考文献：
  名称：

  FILHO, J. M. BARBOSA;MEDEIROS, DELBY F.;AGRA, M. DE FATIMA;BHATTACHARYYA,+, PHYTOCHEMISTRY, 28,(1989) N, C. 1985-1986

  摘要：

  DOI：
• 作为产物：
  描述：

  26-O-β-D-glucopyranosyl-(25S)-5α-furost-20(22)-ene-2α,3β,26-triol 3-O-α-L-rhamnopyranosyl-(1->2)-O-β-D-glucopyranoside 在 三氟乙酸 作用下， 反应 3.0h， 以7 mg的产率得到(25S)-5α-spirostane-2α,3β-diol
  参考文献：
  名称：

  Furostanol saponins from Allium tuberosum

  摘要：

  Three new furostanol saponins, tuberoside A, B and C, have been isolated from the seeds of Allium tuberosum. On the basis of chemical reactions and spectral data, their structures were established as 26-O-beta-D-glucopyranosyl-(25 S)-5 alpha-furost-20(22)-ene-2 alpha,3 beta,26-triol 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-O-beta-D-glucopyranoside; 26-O-beta-D-glucopyranosyl-(25 S)-5 alpha-furost-20(22)-ene-2 alpha,3 beta,26-triol 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-[alpha-L-rhamnopyranosyl-(1 --> 4)]-beta-D-glucopyranoside and 26-O-beta-D-glucopyranosyl-(25 S)-5 alpha-furost-20(22)-ene-2 alpha,3 beta,26-triol 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-[beta-D-glucopyranosyl-(1 -->3)]-beta-D-glucopyranoside, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(99)00312-x

文献信息

• The bioassay-guided isolation of antifungal saponins from <i>Hosta plantaginea</i> leaves
  作者：Meng-Yue Wang、Ying Peng、Chong-Sheng Peng、Jiang-Yuan Qu、Xiao-Bo Li

  DOI：10.1080/10286020.2017.1329304

  日期：2018.6.3

  steroidal saponins hostaside Ⅰ (1), hostaside Ⅱ (2), hostaside Ⅲ (3), and hostaside Ⅳ (4), together with five known steroidal saponins (5–9), were isolated by the bioassay-guided fractionation from the leaves of Hosta plantaginea (Lam.) Aschers, a worldwide well-known ornamental plant. Hostasides Ⅰ and Ⅱ showed significant antifungal activities, and they could inhibit the growth of Candida albicans

  通过生物分析指导分离分离出四种新的甾体皂苷Ⅰ（1），Ⅱ（2），Ⅲ（3）和Ⅳ（4），以及五种已知甾体皂苷（5-9）。全世界著名的观赏植物植物玉Host（叶子）的叶子。HostasidesⅠ，Ⅱ表明显著的抗真菌活性，并且它们能抑制生长白色念珠菌和尖孢镰刀菌与MIC值低4微克/毫升。
• Medicinal Foodstuffs. IV. Fenugreek Seed. (1): Structures of Trigoneosides Ia, Ib, IIa, IIb, IIIa, and IIIb, New Furostanol Saponins from the Seeds of Indian Trigonella foenum-graecum L.
  作者：Masayuki YOSHIKAWA、Toshiyuki MURAKAMI、Hajime KOMATSU、Nobutoshi MURAKAMI、Johji YAMAHARA、Hisashi MATSUDA

  DOI：10.1248/cpb.45.81

  日期：——

  26-O-beta-D-glucopyranosyl-(25R)-5 beta-furostane-3 beta,22 zeta,26-triol 3-O-[beta-D-xylopyranosyl (1-->6)]-beta-D-glucopyranoside, 26-O-beta-D-glucopyranosyl-(25S)-5 alpha-furostane-3 beta,22 zeta,26-triol 3-O-[alpha-L-rhamnopyranosyl(1 --> 2)]-beta-D-glucopyranoside, and 26-O-beta-D-glucopyranosyl-(25R)-5 alpha-furostane-3 beta,22 zeta,26-triol 3-O-[alpha-L-rhamnopyranosyl (1 --> 2)]-beta-D-glucopyranoside

  从药用食品葫芦巴种子（胡芦巴种子）中分离出六个新的呋喃固醇皂苷，称为皂角苷Ia，Ib，IIa，IIb，IIIa和IIIb，还有印度产的Trigonella foenum-graecum L.（豆科）的种子和两种已知的皂苷，根据化学和物理化学证据确定了三方苷Ia，Ib，IIa，IIb，IIIa和IIIb的结构为26-O-β-D-吡喃葡萄糖基-（25S）-5 alpha- furostane-2 alpha，3 beta，22 zeta，26-tetraol 3-O- [β-D-xylopyranosyl（1-> 6）]-beta-D-glucopyranoside，26-O-beta-D-glucopyranosyl-（ 25R）-5 alpha-furostane-2 alpha，3 beta，22 zeta，26-tetraol 3-O- [beta-D-xylopyranosyl（1->
• Steroidal constituents from the leaves of Hosta longipes and their inhibitory effects on nitric oxide production
  作者：Chung Sub Kim、Sun Yeou Kim、Eunjung Moon、Mi Kyeong Lee、Kang Ro Lee

  DOI：10.1016/j.bmcl.2013.01.050

  日期：2013.3

  two known steroidal saponins (4 and 5). The identification and structural elucidation of these compounds were based on 1D and 2D NMR measurements, high-resolution FAB mass spectroscopy (HR-FAB-MS), and chemical methods. A proinflammatory mediator, nitric oxide (NO), in murine microglial BV-2 cells was used to assess the anti-neuroinflammatory effect of the isolated compounds from H. longipes. Among them

  长柄玉簪（FR。等SAV）松村（百合科）是韩国的食用植物油。进行这项研究的目的是评估长双歧杆菌作为治疗神经退行性疾病（如阿尔茨海默氏病和帕金森氏病）的功能性食品的潜力。在这方面，该研究导致了三个新的甾族化合物，longipenane（标识1），26- longipenane ø -β- d吡喃葡萄糖苷（2）和neogitogenin 3- ö -α-升-rhamnopyranosyl-（1→2 ）-O- [β- d-吡喃葡萄糖基-（1→4）]-β- d-吡喃半乳糖苷（3），以及两种已知的甾体皂苷（4和5）。这些化合物的鉴定和结构解析基于1D和2D NMR测量，高分辨率FAB质谱（HR-FAB-MS）和化学方法。甲促炎介质，一氧化氮（NO），在小胶质细胞的鼠用BV-2细胞，以评估分离的化合物的从防神经炎效果H.长柄。其中，化合物4和5在脂多糖激活的BV-2细胞中对NO产生强抑制作用，而没有高细胞毒性（IC
• Medicinal Foodstuffs. XVII. Fenugreek Seed. (3). Structures of New Furostanol-Type Steroid Saponins, Trigoneosides Xa, Xb, XIb, XIIa, XIIb, and XIIIa, from the Seeds of Egyptian Trigonellafoenum-graecum L.
  作者：Toshiyuki MURAKAMI、Akinobu KISHI、Hisashi MATSUDA、Masayuki YOSHIKAWA

  DOI：10.1248/cpb.48.994

  日期：——

  Six new furostanol-type steroid saponins called trigoneosides Xa, Xb, XIb, XIIa, XIIb, and XIIIa were isolated from the seeds of Egyptian Trigonella foenum-graecum L. (Leguminosae) together with six known furostanol-type steroid saponins : trigoneosides Ia, Ib, and Va, glycoside D, trigonelloside C, and compound C. The structures of trigoneosides Xa, Xb, XIb, XIIa, XIIb, and XIIIa were determined on the basis of chemical and physicochemical evidence as 26-O-β-D-glucopyranosyl-(25S)-5α-furostane-2α, 3β, 22ξ, 26-tetraol 3-O-α-L-rhamnopyranosyl(1→2)-β-D-glucopyranoside, 26-O-β-D-glucopyranosyl-(25R)-5α-furostane-2α, 3β, 22ξ, 26-tetraol 3-O-α-L-rhamnopyranosyl(1→2)-β-D-glucopyranoside, 26-O-β-D-glucopyranosyl-(25R)-5α-furostane-2α, 3β, 22ξ, 26-tetraol 3-O-β-D-xylopyranosyl(1→4)-β-D-glucopyranoside, 26-O-β-D-glucopyranosyl-(25S)-furost-4-ene-3β, 22ξ, 26-triol 3-O-α-L-rhamnopyranosyl(1→2)-β-D-glucopyranoside, 26-O-β-D-glucopyranosyl-(25R)-furost-4-ene-3β, 22ξ, 26-triol 3-O-α-L-rhamnopyranosyl(1→2)-β-D-glucopyranoside, and 26-O-β-D-glucopyranosyl-(25S)-furost-5-ene-3β, 22ξ, 26-triol 3-O-α-L-rhamnopyranosyl(1→2)-[β-D-glucopyranosyl(1→3)-β-D-glucopyranosyl(1→4)]-β-D-glucopyranoside, respectively.

  从埃及毛果芸香（豆科植物）的种子中分离出了六种新的呋喃甾醇型甾体皂甙，即三棱苷 Xa、Xb、XIb、XIIa、XIIb 和 XIIIa，以及六种已知的呋喃甾醇型甾体皂甙：三棱苷 Ia、Ib 和 Va、苷 D、三棱苷 C 和化合物 C。根据化学和物理化学证据，确定了三酮苷 Xa、Xb、XIb、XIIa、XIIb 和 XIIIa 的结构为 26-O-β-D-吡喃葡萄糖基-(25S)-5α-呋喃甾烷-2α，3β，22ξ、26-tetraol 3-O-α-L-rhamnopyranosyl(1→2)-β-D-glucopyranoside, 26-O-β-D-glucopyranosyl-(25R)-5α-furostane-2α, 3β, 22ξ、26-tetraol 3-O-α-L-rhamnopyranosyl(1→2)-β-D-glucopyranoside, 26-O-β-D-glucopyranosyl-(25R)-5α-furostane-2α, 3β, 22ξ、26-tetraol 3-O-β-D-xylopyranosyl(1→4)-β-D-glucopyranoside, 26-O-β-D-glucopyranosyl-(25S)-furost-4-ene-3β, 22ξ, 26-triol 3-O-α-L-rhamnopyranosyl(1→2)-β-D-glucopyranoside, 26-O-β-D-glucopyranosyl-(25R)-furost-4-ene-3β, 22ξ、26-triol 3-O-α-L-rhamnopyranosyl(1→2)-β-D-glucopyranoside 和 26-O-β-D-glucopyranosyl-(25S)-furost-5-ene-3β, 22ξ、26-三醇 3-O-α-L-吡喃鼠李糖基（1→2）-[β-D-吡喃葡萄糖基（1→3）-β-D-吡喃葡萄糖基（1→4）]-β-D-吡喃葡萄糖苷。
• Steroidal Sapogenins. No. 160. The Conversion of Pseudosapogenins to Sapogenins and Neosapogenins
  作者：Russell E. Marker、Josefina Lopez

  DOI：10.1021/ja01202a036

  日期：1947.10