报春花甙元 | 465-95-2

• 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
• 中文名称: 报春花甙元
• 英文名称: primulagenin A
• 英文别名: 3β,16α,28-trihydroxy-12-oleanene；3β,16α,28-trihydoxyolean-12-ene；primulagenin；olean-12-ene-3β,16α,28-triol；Olean-12-en-3β,16α,28-triol；(4aS)-5t,10c-Dihydroxy-2,2,6at,6bc,9,9,12ac-heptamethyl-4ar-hydroxymethyl-(8atH,12btH,14bcH)-Δ¹⁴-eicosahydro-picen；(3S,4aR,6aR,6bS,8R,8aS,12aS,14aR,14bR)-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,8-diol
• CAS: 465-95-2
• 化学式: C₃₀H₅₀O₃
• 分子量: 458.725
• InChiKey: YHGVYECWZWIVJC-TVZJSHMMSA-N

物化性质

• 熔点：
  240-242 °C
• 沸点：
  551.0±50.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  33
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

制备方法与用途

primulagenin A 是一种苷类化合物，可以从刺五加（Eleutheroccus senticosus）的根中分离获得。

反应信息

• 作为反应物：
  描述：

  报春花甙元 在 chromium(VI) oxide 作用下， 以 丙酮 为溶剂， 生成 3,16-dioxo-olean-12-en-28-al
  参考文献：
  名称：

  995.环磷酰胺的组成和立体化学

  摘要：

  DOI：

  10.1039/jr9620005176
• 作为产物：
  描述：

  (4aS)-5t,10c-diacetoxy-2,2,6at,6bc,9,9,12ac-heptamethyl-4ar-hydroxymethyl-(8atH,12btH,14bcH)-Δ¹⁴-eicosahydro-picene 在 氢氧化钾 作用下， 生成 报春花甙元
  参考文献：
  名称：

  Maintaining Gut Integrity During Parenteral Nutrition of Tumor-Bearing Rats: Effects of Glucagon-Like Peptide 2

  摘要：

  Maintaining tumor-bearing rats on total parenteral nutrition (TPN)for eight days significantly reduced mass, protein, and DNA in small intestine and colon. Coinfusion of glucagon-like peptide 2 (GLP-2) significantly increased each of these variables in the duodenum, jejunum, and ileum, but not in the colon. Histological analysis of tissue revealed normal mucosa thickness and villus height in the small intestine of GLP-2-treated rats, whereas nontreated rats maintained on TPN exhibited villus shortening and thinning of the mucosa. Compared with TPN alone, no significant effects of GLP-2 were noted on tumor growth, liver weight, or heart weight. Coinfusion of GLP-2 with TPN had no significant effect on TPN-associated immunosuppression, as measured by mitogen-induced proliferation of cultured splenocytes. Although translocation of bacteria to the mesenteric lymph nodes appeared to be reduced in GLP-2-treated vats, the difference between groups was not statistically significant. These results suggest that hormonal alterations may be more important than an absence of luminal nutrition in TPN-associated mucosa changes in tumor-bearing rats. Additionally, maintenance of gut integrity during TPN does not appear to be a sufficient condition for the avoidance of the negative sequelae associated with this route of supplemental nutrition.

  DOI：

  10.1207/s15327914nc372_15

文献信息

• The structure of prosapogenin obtained from the saponin of Gleditsia japonica
  作者：Takao Konoshima、Hiroyuki Fukushima、Hideo Inui、Keiko Sato、Tokunosuke Sawada

  DOI：10.1016/0031-9422(81)85233-8

  日期：1981.1

  Abstract Prosapogenin was obtained by alkaline hydrolysis of Gleditsia saponin GS-C (echinoeystic acid 3, 28-O-bisdesmoside), a new triterpenoid saponin isolated from Gleditsia japoinica. Prosapogenin was shown on the basis of chemical and physicochemical data to be echinocystic acid 3-O-β- d -xylopyranosyl-(1–2)-α- l -arabinopyranosyl-(1–6)-β- d -glucopyranoside.

  摘要 Prosapogenin 是通过皂苷 GS-C（棘皮酸 3, 28-O-bisdesmoside）碱水解获得的，该皂苷是从皂角中分离得到的一种新的三萜皂苷。根据化学和物理化学数据显示，前皂苷元是棘囊酸 3-O-β-d-吡喃木糖基-(1-2)-α-l-阿拉伯吡喃糖基-(1-6)-β-d-吡喃葡萄糖苷。
• New triterpenoid glycosides from the leaves of Bupleurum rotundifolium L.
  作者：YOSHIMASA KOBAYASHI、TADAHIRO TAKEDA、YUKIO OGIHARA

  DOI：10.1248/cpb.29.2222

  日期：——

  Two new triglycosides of oleanane-type triterpenes, rotundioside E (3) and F (1), isolated from the leaves of Bupleurum rotundifolium L. were identified as 16α, 28-dihydroxyoleana-11, 13 (18)-dien-3β-yl α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-fucopyranoside (3) and 13β, 28-epoxy-16α-hydroxyoleana-11-en-3β-yl α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-fucopyranoside (1), respectively, on the basis of chemical and spectroscopic evidence.

  从Bupleurum rotundifolium L.叶片中分离出的两种新的齐墩果烷型三萜类化合物--罗汉果苷E (3)和F (1)，被鉴定为16α, 28-二羟基油菜-11, 13 (18)-dien-3β-yl α-L→2）-β-吡喃葡萄糖基被鉴定为 16α，28-二羟基油菜-11，13 (18)-二烯-3β-基 α-L-鼠李糖基-(1→2)-β-D-吡喃葡萄糖基-(1→2)-β-D-吡喃葡萄糖苷 (3) 和 13β、28-epoxy-16α-hydroxyoleana-11-en-3β-yl α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-fucopyranoside (1)。
• Triterpene saponins of Maesa lanceolata leaves
  作者：Lawrence Onyango A. Manguro、Jacob O. Midiwo、Lutz F. Tietze、Pang Hao

  DOI：10.3998/ark.5550190.0012.214

  日期：——

  Chemical investigation of Maesa lanceolata leaves aqueous MeOH extract has led to the isolation of eight new triterpene glycosides identified as 16-oxo-28-hydroxyolean-12-ene 3-O- β-glucopyranosyl-(1''→6')-β-glucopyranoside 1, 16α, 28-dihydroxyolean-12-ene 3 -O-β-((6''-O-galloylglucopyranosyl-(1''→2'))(β-glucopyranosyl-(1'''→6'))-β-glucopyranoside 2, 16α, 22α, 28-trihydroxyolean-12-ene 3-O-(β-gluc

  对 Maesa lanceolata 叶含水 MeOH 提取物的化学研究导致分离出八种新的三萜糖苷，鉴定为 16-oxo-28-hydroxyolean-12-ene 3-O-β-glupyranosyl-(1''→6')-β -吡喃葡萄糖苷 1, 16α, 28-dihydroxyolean-12-ene 3 -O-β-((6''-O-galloylglupyranosyl-(1''→2'))(β-glupyranosyl-(1'''→6) '))-β-吡喃葡萄糖苷 2, 16α, 22α, 28-trihydroxyolean-12-ene 3-O-(β-glupyranosyl-(1''→2')) (α-rhamnopyranosyl-(1'''→6) ')-β-吡喃葡萄糖苷 3, 22α-乙酰基-16α-hydroxyolean-12-en-28-al 3-O-(α-rhamnop
• Chemistry of aegiceras majus gaertn—III
  作者：K.Venkateswara Rao、P.K. Bose

  DOI：10.1016/s0040-4020(01)92693-6

  日期：1962.1

  Aegiceradiol, C30H48O2, a new triterpene diol from Aegicera majus Gaertn, is 3β,28-dihydroxy olean-12,15-diene and its partial synthesis from genin-A is described.

  得自Aegicera majus Gaertn的新的三萜二醇Aegiceradiol，C 30 H 48 O 2是3β，28-二羟基齐聚物-12，15-二烯，并且描述了其从genin-A的部分合成。
• Selective oxidation of oleanane triterpenoids
  作者：Yoshimasa Kobayashi、Muneharu Ogawa、Yukio Ogihara

  DOI：10.1039/p19810002277

  日期：——

  of CrO3, pyridine, and BunOH saturated with water. The reaction of the oleanane triterpenoid glycosides (1), (4), and (5) with reagent A gave 11-oxo-compounds (3) and (6), which indicated that this reagent is useful for the oxidation of an allyl alcohol and an allyl ether. On the other hand, the reaction of oleanane triterpenoids (11), (13), (14), and (15) with reagent A gave 16-oxo-derivatives (9)

  从CrO 3，吡啶和用水饱和的Bu n OH的混合物中获得试剂A（确切的组成未知）。齐墩果烷三萜糖苷（1），（4）和（5）与试剂A的反应生成11-氧代化合物（3）和（6），这表明该试剂可用于烯丙醇的氧化和烯丙基醚 另一方面，齐墩果烷三萜类化合物（11），（13），（14）和（15）与试剂A的反应产生了16-氧代衍生物（9），（16），（17）和（18）。 ，同时化合物（19）和（22）与该试剂一起生成21-氧代衍生物（24）和（25）。试剂A对于16和21轴羟基的选择性氧化也非常有用。