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：——
• Sesquiterpene glycosides and saponins from Cynara cardunculus L.
  作者：SHIGERU SHIMIZU、NAOMI ISHIHARA、KAORU UMEHARA、TOSHIO MIYASE、AKIRA UENO

  DOI：10.1248/cpb.36.2466

  日期：——

  A new guaiane-type sesquiterpene glycoside, cynaroside A, seven new ursane-type saponins, cynarasaponins A-G, and three new oleanase-type saponins, cynarasaponins H-J, have been isolated from Cynara cardunculus L., together with a known guaiane-type sesquiterpene glycoside, 11β, 13-dihydrodesacylcynaropicrin-8-β-D-glucoside, and a known oleanane-type saponin, chikusetsusaponin IVa. The structures of the new compounds were established on the basis of chemical and spectral data. This is the first isolation of saponin from Compositae plants.

  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。
• Bioactive oleanolic acid saponins and other constituents from the roots of Viguiera decurrens
  作者：Silvia Marquina、Nora Maldonado、Marı́a Luisa Garduño-Ramı́rez、Eduardo Aranda、Marı́a Luisa Villarreal、Vı́ctor Navarro、Robert Bye、Guillermo Delgado、Laura Alvarez

  DOI：10.1016/s0031-9422(00)00283-1

  日期：2001.1

  The bisdesmoside oleanolic acid saponin, 3-0-(methyl-beta-D-glucuronopyranosiduronoate)-28-0-beta-D-glucopyranosyl-oleanolate along with nine known compounds (two diterpenic acids, one chromene, three triterpenes, one steroidal glycoside, and two monodesmoside oleanolic acid saponins), were obtained from Viguiera decurrens roots. The chemical structure of the bisdesmoside oleanolic saponin was determined

  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。