3-O-(methyl-β-D-glucuronopyranosiduronoate)-28-O-β-D-glucopyranosyl oleanolate | 58546-61-5

• 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: 3-O-(methyl-β-D-glucuronopyranosiduronoate)-28-O-β-D-glucopyranosyl oleanolate
• 英文别名: 3-O-(methyl-β-D-glucuronpyranosiduronate)-28-O-β-D-glucopyranosyl oleanolate；chikusetsu saponin IVa methyl ester；chikusetsusaponin IVa methyl ester；chikusetsusaponin-IVa methyl ester；chikusetsusaponin IV methyl ester；methyl (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4,4,6a,6b,11,11,14b-heptamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylate
• CAS: 58546-61-5
• 化学式: C₄₃H₆₈O₁₄
• 分子量: 809.005
• InChiKey: XPORLJWHBRUXGD-HWIUFREPSA-N

物化性质

• 沸点：
  841.6±65.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  57
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  222
• 氢给体数：
  7
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  3-O-(methyl-β-D-glucuronopyranosiduronoate)-28-O-β-D-glucopyranosyl oleanolate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 齐墩果酸
  参考文献：
  名称：

  来自 Viguiera decurrens 根的生物活性齐墩果酸皂苷和其他成分

  摘要：

  双桥苷齐墩果酸皂苷、3-0-(methyl-beta-D-glucuronopyranosiduronoate)-28-0-beta-D-吡喃葡萄糖基齐墩果酸以及九种已知化合物（两种二萜酸、一种色烯、三种三萜、一种甾体糖苷, 和两种单糖苷齐墩果酸皂苷), 从 Viguiera decurrens 根中获得。bisdesmoside oleanolic saponin 的化学结构由化学和 NMR 光谱证据确定。Monodesmoside 皂苷的混合物显示出针对 P388 和 COLON 细胞系的细胞毒活性（ED50 = 2.3 和 3.6 microg/ml，分别）。两种已知化合物对墨西哥豆甲虫幼虫（Epilachna varivestis）显示出杀虫活性。

  DOI：

  10.1016/s0031-9422(00)00283-1
• 作为产物：
  描述：

  重氮甲烷 、 竹节人参皂苷 Iva 生成 3-O-(methyl-β-D-glucuronopyranosiduronoate)-28-O-β-D-glucopyranosyl oleanolate
  参考文献：
  名称：

  Sesquiterpene glycosides and saponins from Cynara cardunculus L.

  摘要：

  从茜草（Cynara cardunculus L.）中分离出了一种新的胍型倍半萜苷--茜草苷 A，七种新的熊果苷型皂甙--茜草皂甙 A-G，以及三种新的齐墩果酶型皂甙--茜草皂甙 H-J、以及一种已知的愈创木萜类倍半萜苷--11β，13-二氢去乙酰基炔诺酮素-8-β-D-葡萄糖苷和一种已知的齐墩果皂苷 IVa。根据化学和光谱数据确定了新化合物的结构。这是首次从菊科植物中分离出皂苷。

  DOI：

  10.1248/cpb.36.2466

文献信息

• Achyranthosides A and B, novel cytotoxic saponins from Achyranthes fauriei root
  作者：Yoshiteru Ida、Yohko Satoh、Mariko Katoh、Masumi Katsumata (nee Ohtsuka)、Miki Nagasao、Kentaro Yamaguchi、Hideo Kamei、Junzo Shoji

  DOI：10.1016/0040-4039(94)85032-1

  日期：1994.9

  Two new saponins, achyranthosides A and B, were isolated from Achyranthes fauriei root, and their structures were elucidated on the basis of chemical and physical evidences. Achyranthoside A methyl ester was found to have significant cytotoxic activity against human colon carcinoma and murine melanoma cells.

  从牛膝草的根中分离出两种新的皂苷，牛膝甙A和B，并根据化学和物理证据阐明了它们的结构。发现牛膝苦苷A甲酯对人结肠癌和鼠黑素瘤细胞具有显着的细胞毒性活性。
• Synthesis of Betavulgaroside III, a Representative Triterpene <i>seco</i>-Glycoside
  作者：Shilei Zhu、Yingxia Li、Biao Yu

  DOI：10.1021/jo800669h

  日期：2008.7.1

  Triterpene seco-glycosides constitute a small family of the plant saponins which feature a terminal seco-saccharide appendage deriving supposedly from oxidative scission of a monosaccharide unit. Herein, we have developed synthetic approaches for the first time to the access to these molecules. Betavulgaroside III (1), a representative congener occurring in Beta vulgaris and Achyranthes fauriei, is successfully synthesized in a total of 31 steps with L-arabinose, D-glucose, and oleanolic acid as starting materials. The longest linear sequence requires 23 steps and in an overall 0.9% yield (from D-glucose). The synthesis features oxidative elaboration of the seco-saccharide unit prior to assembly of the triterpene 3,28-bisglycoside. This tactic has been proven superior, in the attempts to the synthesis of the more easily accessible 2 ''-epi-betavulgaroside III (2), to that employing oxidative cleavage of the terminal saccharide unit at an advanced triterpene 3,28-bisglycoside scaffold.
• SATI, O. P.;BAHUGUNA, S.;UNIYAL, S.;SAKAKIBARA, J.;KAIYA, T.;NAKAMURA, A., J. NATUR. PROD., 53,(1990) N, C. 466-469
  作者：SATI, O. P.、BAHUGUNA, S.、UNIYAL, S.、SAKAKIBARA, J.、KAIYA, T.、NAKAMURA, A.

  DOI：——

  日期：——