16α-hydroxygypsogenic acid

• 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: 16α-hydroxygypsogenic acid
• 英文别名: 16alpha-Hydroxygypsogenic acid；(3S,4S,4aR,6aR,6bS,8R,8aR,12aS,14aR,14bR)-3,8-dihydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylic acid
• 化学式: C₃₀H₄₆O₆
• 分子量: 502.692
• InChiKey: NZUXOCGZXRCSGC-DRLBPWGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  36
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3β,16α-dihydroxyolean-12-ene-23,28-dioic acid (16α-hydroxygypsogenic acid) 28-O-β-D-glucopyranosyl-(1→2'')-β-D-glucopyranosyl-(1→6')-β-D-glucopyranosyl ester 在 水 、 potassium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以7.6 mg的产率得到16α-hydroxygypsogenic acid
  参考文献：
  名称：

  石竹的地上部分中的石竹皂苷GI，三萜皂苷，邻氨基苯甲酸酰胺葡糖苷和类黄酮糖苷及其细胞毒性。

  摘要：

  对石竹地面部分的MeOH提取物的1-BuOH可溶级分进行广泛的分离工作，得到了另外三种三萜烯糖基酯，称为双硫皂苷G-1，邻氨基苯甲酸酰胺糖苷和C-糖基类黄酮，以及一种已知的化合物。三萜皂苷。从光谱学证据阐明了它们的结构。评价了分离的化合物对A549细胞的细胞毒性。

  DOI：

  10.1007/s11418-016-1019-8

文献信息

• Oleanane-type triterpenoid saponins from Silene armeria
  作者：Nobuyuki Takahashi、Wei Li、Kazuo Koike

  DOI：10.1016/j.phytochem.2016.07.011

  日期：2016.9

  Twelve triterpenoid saponins, including seven compounds (i.e., armerosides A-G) hitherto unknown, were isolated from whole plants of Silene armeria. Their structures were established based on extensive spectroscopic analyses and chemical methods. From a biosynthetic perspective, C-23 oxidation of the sapogenin appears to be a key factor in the glycosylation pathway.

  从 Silene armeria 的整个植物中分离出 12 种三萜皂苷，包括迄今为止未知的 7 种化合物（即 armerosides AG）。它们的结构是基于广泛的光谱分析和化学方法建立的。从生物合成的角度来看，皂苷元的 C-23 氧化似乎是糖基化途径中的关键因素。
• Three New Triterpenoid Saponins from <i>Dianthus superbus</i>
  作者：Jian-Guang Luo、Xia Chen、Ling-Yi Kong

  DOI：10.1248/cpb.59.518

  日期：——

  Three new triterpenoid saponins (1-3) were isolated from the dried aerial parts of Dianthus superbus L. (Caryophyllaceae). Their structures were established as 3-O-β-D-glucopyranosyl gypsogenic acid 28-O-[β-D-6-O-((3S)-3-hydroxyl-3-methylglutaryl)glucopyranosyl(1→6)]-β-D-glucopyranoside (1), 3-O-β-D-glucopyranosyl gypsogenic acid 28-O-[β-D-glucopyranosyl(1→3)][β-D-6-O-((3S)-hydroxyl-3-methylglutar

  从石竹超级干（石竹科）的干燥地上部分中分离出三种新的三萜皂苷（1-3）。它们的结构被确定为3-O-β-D-吡喃葡萄糖基石膏酸28-O- [β-D-6-O-（（（3S）-3-hydroxyl-3-methylglutaryl）glucopyranosyl（1→6）]- β-D-吡喃葡萄糖苷（1），3-O-β-D-吡喃葡萄糖基葡糖酸28-O- [β-D-吡喃葡萄糖基（1→3）] [β-D-6-O-（（3S）-羟基-3-甲基戊二酰基）吡喃葡萄糖基（1→6）]-β-D-吡喃葡萄糖苷（2），3-O-α-L-阿拉伯吡喃糖基-3β，16α-二羟基油酸酯-12-en-23,28-二酸28 -O- [β-D-吡喃葡萄糖基-（1→6）]-β-D-吡喃葡萄糖苷（3），基于各种光谱分析和化学降解。
• Triterpenoid saponins from Dianthus chinensis
  作者：Li Hong-Yu、Kazou Koike、Taichi Ohmoto

  DOI：10.1016/s0031-9422(00)90599-5

  日期：1994.2

  alpha, 28 beta-dioic acid 28-O-beta-D-glucopyranosyl [1-->6)-beta-D-glucopyranoside] were isolated from the aerial parts of Dianthus chinensis. Their structures were determined by spectroscopic methods and chemical evidence. We also report the revision of a previous misassignment of hainanenside, isolated from Ilex hainanensis Merr. In addition, known compounds, 3-O-alpha-L-arabinopyranosyl hederagenin

  两种新型三萜皂苷、二萜皂苷 C [23-O-β-D-吡喃葡萄糖基 3β、16 α-二羟基齐墩果-12-烯 23 α、28 β-二酸 28-O-β-D-吡喃葡萄糖苷] 和二萜皂苷 D [ 3 beta, 16 alpha-dihydroxyolean-12-ene 23 alpha, 28 beta-dioic acid 28-O-beta-D-glucopyranosyl [1-->6)-beta-D-glucopyranoside] 从石竹的地上部分分离中华。它们的结构是通过光谱方法和化学证据确定的。我们还报告了对从 Ilex hainanensis Merr 中分离的 hainanenside 的先前错误分配的修订。此外，已知化合物，3-O-α-L-arabinopyranosyl hederagenin 28-O-β-D-吡喃葡萄糖基 (1-->6)-β-D-吡喃葡萄糖苷，谷甾醇 3
• New Triterpenoid Saponins and Sapogenins from <i>Saponaria officinalis</i>
  作者：Kazuo Koike、Zhonghua Jia、Tamotsu Nikaido

  DOI：10.1021/np990311r

  日期：1999.12.1

  Five new triterpenoid saponins, named saponariosides I-M, were isolated from the whole plants of Saponario officinalis. Their structures were established as saponarioside I (1) 3-O-beta-D-xylopyranosyl-16 alpha-hydroxygypsogenic acid 28-O-alpha-D-galactopyranosyl-(1-->6)-beta-D- glucopyranosyl-(1-->3)[-beta-D-glucopyranoside[, saponarioside J (3) 3-O-beta-D-xylopyranosylolean-11,13(18)-diene-23,28-dioic

  从五倍子的整个植物中分离出五个新的三萜皂苷，命名为五倍子皂苷IM。它们的结构被确定为皂苷I（1）3-O-β-D-吡喃并吡喃糖基-16α-羟基石膏酸28-O-α-D-吡喃并吡喃糖基-（1-> 6）-β-D-吡喃葡萄糖基-（ 1-> 3）[-beta-D-glucopyranoside [，saponarioside J（3）3-O-beta-D-xylopyranosylolean-11,13（18）-diene-23,28-diic acid 28-O-beta -D-吡喃葡萄糖基-（1-> 3）-β-D-吡喃葡萄糖基-（1-> 6）[-β-D-吡喃葡萄糖苷[，皂苷K（4）3,4-seco-16 alpha-hydroxygypsogenic酸28-O-β-D-吡喃葡萄糖基-（1-> 3）-β-D-吡喃葡萄糖基-（1-> 6）[-β-D-吡喃葡萄糖苷[，皂苷L（5）3-O- β-D-吡喃并
• Dianthosaponins G–I, triterpene saponins, an anthranilic acid amide glucoside and a flavonoid glycoside from the aerial parts of Dianthus japonicus and their cytotoxicity
  作者：Yuka Kanehira、Susumu Kawakami、Sachiko Sugimoto、Katsuyoshi Matsunami、Hideaki Otsuka

  DOI：10.1007/s11418-016-1019-8

  日期：2016.10

  Extensive isolation work on the 1-BuOH-soluble fraction of a MeOH extract of the aerial parts of Dianthus japonicus afforded three further triterpene glycosyl estsers, termed dianthosaponins G–I, an anthranilic acid amide glucoside and a C-glycosyl flavonoid along with one known triterpene saponin. Their structures were elucidated from spectroscopic evidence. The cytotoxicity of the isolated compounds

  对石竹地面部分的MeOH提取物的1-BuOH可溶级分进行广泛的分离工作，得到了另外三种三萜烯糖基酯，称为双硫皂苷G-1，邻氨基苯甲酸酰胺糖苷和C-糖基类黄酮，以及一种已知的化合物。三萜皂苷。从光谱学证据阐明了它们的结构。评价了分离的化合物对A549细胞的细胞毒性。