bryodulcosigenin | 88930-16-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: bryodulcosigenin
• 英文别名: 11-oxo-mogrol；(3S,8S,9R,10R,13R,14S,17R)-17-[(2R,5R)-5,6-dihydroxy-6-methylheptan-2-yl]-3-hydroxy-4,4,9,13,14-pentamethyl-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-11-one
• CAS: 88930-16-9
• 化学式: C₃₀H₅₀O₄
• 分子量: 474.725
• InChiKey: FPMQKXQOBKDVHF-DJHQPCGUSA-N

物化性质

• 熔点：
  186 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  594.9±50.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

制备方法与用途

11-氧莫果灵是一种三萜苷元，能够抑制EB病毒早期抗原（EBV-EA）的激活。

反应信息

• 作为反应物：
  描述：

  bryodulcosigenin 在 羟胺磷酸盐 、 二乙胺 、 三乙胺 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 9.0h， 生成
  参考文献：
  名称：

  一种11-O-罗汉果醇肟酯衍生物及其制备方 法

  摘要：

  本发明提供了一种11‑O‑罗汉果醇肟酯衍生物及其制备方法。所述11‑O‑罗汉果醇肟酯衍生物的结构式如式(I)所示。该衍生物在11‑O‑罗汉果醇的酮基肟化后再进行酯化，得到产物11‑O‑罗汉果醇肟酯衍生物。本发明提供的11‑O‑罗汉果醇肟酯衍生物制备方法简单，纯度和产率高。所得11‑O‑罗汉果醇肟酯衍生物相比于11‑O‑罗汉果醇，具有明显增强的抗氧化活性，而且酯水分配比适合作为化妆品中的抗氧化剂成分，能够明显改善皮肤的衰老状况。

  公开号：

  CN111533776B
• 作为产物：
  描述：

  11-oxomogroside I A₁ 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 bryodulcosigenin
  参考文献：
  名称：

  Inhibitory Effects of Cucurbitane Glycosides and Other Triterpenoids from the Fruit of Momordica grosvenori on Epstein−Barr Virus Early Antigen Induced by Tumor Promoter 12-O-Tetradecanoylphorbol-13-acetate

  摘要：

  Two new triterpene benzoates, 5-dehydrokarounidiol dibenzoate (1) and karounidiol dibenzoate (2), and two new triterpene glycosides, 5alpha,6alpha-epoxymogroside IE1 (8) and 11-oxomogroside A(1) (9), along with 15 known triterpenoids (one triterpene benzoate, 3; three triterpene mono-ols, 4-6; one triterpene aglycon, 7; and 10 triterpene glycosides, 10-19), were isolated from the ethanol extract of the fruit of Momordica grosvenori. The structures of 1, 2, 8, and 9 were determined on the basis of spectroscopic and chemical methods. Among the known triterpene glycosides, mogroside I E-1 (12) was a new naturally occurring compound. Eighteen triterpenoids (2-19) and 11-oxomogrol (20), a hydrolysis product of 9, were evaluated with respect to their inhibitory effects on the induction of Epstein-Barr virus early antigen (EBV-EA) by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells, which is known to be a primary screening test for antitumor promoters. All of the compounds tested showed potent inhibitory effects on EBV-EA induction (70-100% inhibition at 1 X 10(3) Mol ratio/TPA).

  DOI：

  10.1021/jf0206320

文献信息

• Efficient O-Glycosylation of Triterpenes Enabled by Protein Engineering of Plant Glycosyltransferase UGT74AC1
  作者：Jiao Li、Jiangang Yang、Shicheng Mu、Na Shang、Cui Liu、Yueming Zhu、Yi Cai、Pi Liu、Jianping Lin、Weidong Liu、Yuanxia Sun、Yanhe Ma

  DOI：10.1021/acscatal.9b05232

  日期：2020.3.20

  wild-type enzyme and conserved regioselectivity. Based on the results of molecular docking and molecular dynamics simulations, it was proposed that the improved enzymatic activity and substrate promiscuity were likely owing to the stable hydrophobic interactions and favorite conformations between the enzyme and substrates. This work has also laid a foundation for the engineering of other plant UGTs for their

  三萜O-糖基化作为药物设计和开发的一种有价值的方法已经引起了制药工业的极大兴趣。催化这种糖基化反应的植物糖基转移酶在制备结构多样且有价值的三萜糖苷中起关键作用。但是，这类酶通常遭受低催化效率的困扰。为了解决这个问题，选择了罗汉果（Siraitia grosvenorii）的三萜糖基转移酶UGT74AC1，并解决了其晶体结构，并将其用作分子基础，以进行定向进化和基于序列/结构的工程。几种合成的尿苷二磷酸（UDP）糖基转移酶（UGT）变体显示10 2-至10 4三萜糖基化的催化效率提高了两倍。尤其是，一种变体对莫格罗的催化效率提高了4.17×10 4倍，而对Mogrol的催化效率提高了1.53×10 4-分别增加至UDP-葡萄糖。此外，与野生型酶相比，该突变体还显示出延长的底物混杂性和保守的区域选择性。基于分子对接和分子动力学模拟的结果，有人提出，由于稳定​​的疏水相互作用和酶与底物之间的偏好
• 一种11-O-罗汉果醇肟醚衍生物及其制备方 法
  申请人：湖南华诚生物资源股份有限公司

  公开号：CN111560044B

  公开（公告）日：2021-02-19

  本发明提供了一种11‑O‑罗汉果醇肟醚衍生物及其制备方法。所述11‑O‑罗汉果醇肟醚衍生物的结构式如下式(I)所示。是在11‑O‑罗汉果醇的酮基肟化后再进行醚化，得到产物11‑O‑罗汉果醇肟醚衍生物。本发明提供的11‑O‑罗汉果醇肟醚衍生物制备方法简单，纯度和产率高。所得11‑O‑罗汉果醇肟醚衍生物相比于11‑O‑罗汉果醇，具有明显增强的抗氧化活性，而且水溶性增强，经过测试，没有毒性，而且具有明显增强的体内半衰期，可以作为食品，饮品，保健品，药品等口服产品中的抗氧化功能添加剂。
• KASAI, RYOJI;NIE, RUI-LIN;NASHI, KENJI;OHTANI, KAZUHIRO;ZHOU, JUN;TAO, GU+, AGR. AND BIOL. CHEM., 53,(1989) N2, C. 3347-3349
  作者：KASAI, RYOJI、NIE, RUI-LIN、NASHI, KENJI、OHTANI, KAZUHIRO、ZHOU, JUN、TAO, GU+

  DOI：——

  日期：——
• Tunmann,P. et al., Justus Liebigs Annalen der Chemie, 1966, vol. 694, p. 162 - 168
  作者：Tunmann,P. et al.

  DOI：——

  日期：——
• Anti-Inflammatory and Anti-Tumor-Promoting Effects of Cucurbitane Glycosides from the Roots of <i>Bryonia dioica</i>
  作者：Motohiko Ukiya、Toshihiro Akihisa、Ken Yasukawa、Harukuni Tokuda、Masakazu Toriumi、Kazuo Koike、Yumiko Kimura、Tamotsu Nikaido、Wataru Aoi、Hoyoku Nishino、Michio Takido

  DOI：10.1021/np010423u

  日期：2002.2.1

  Seven new triterpene glycosides, bryoniosides A-G (1-7), have been isolated along with two known triterpene glycosides, cabenoside D (8) and bryoamaride (9), from a methanol extract of the roots of Bryonia dioica. The structures of 1-7 were determined on the basis of spectroscopic and chemical methods. Six compounds, 2, 3, 5, and 7-9, and 11 compounds, 1-9, bryodulcosigenin (10), and bryosigenin (11), respectively, were evaluated for their inhibitory effects on 12-0-tetradecanoylphorbol-13-acetate (TPA)induced inflammation (1 mug/ear) in mice and on Epstein-Barr virus early antigen (EBV-EA) activation induced by TPA. All compounds tested showed marked anti-inflammatory effects, with 50% inhibitory doses (ID50) of 0.2-0.6 mg per ear. In addition, all of the compounds tested except for compound 5 showed potent inhibitory effects on EBV-EA induction (100% inhibition at 1 x 10(3) mol ratiq/TPA).