(9S)-drummondol | 438045-55-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (9S)-drummondol
• 英文别名: drummondol；(1R,5R,8S)-8-hydroxy-8-[(E,3S)-3-hydroxybut-1-enyl]-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-3-one
• CAS: 438045-55-7
• 化学式: C₁₃H₂₀O₄
• 分子量: 240.299
• InChiKey: KENVUEOHDFOVNA-UFQMABFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (9S)-drummondol 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.08h， 生成
  参考文献：
  名称：

  Ebenamariosides AD：来自海生柿（Diospyros maritima）叶片的三萜糖苷和Megastigmanes。

  摘要：

  用色谱技术分离海产柿（Diospyros maritima）的甲醇（MeOH）提取物中的1-BuOH可溶级分，得到三种新的齐墩果烷型和一种新的乌烷型三萜葡糖苷，称为依贝那马里糖苷AD（1-4）；两个megastigmanes也被隔离。通过一维和二维NMR光谱对三萜糖苷的结构进行了广泛研究，并通过部分酶水解证实了结构，从而给出了相应的单糖苷和糖苷配基。巨型柱头的结构，包括其绝对的立体化学，已通过光谱学证据和改进的Mosher方法得以阐明。两个megastigmanes化学相关联，并明确确定其绝对结构。测定了三萜糖苷及其降解产物的细胞毒性。他们没有显示任何重要活动。

  DOI：

  10.1248/cpb.c19-00803
• 作为产物：
  描述：

  (9S)-drummondol-9-O-β-D-glucopyranoside 在 acetate buffer 、 β-glucosidase 作用下， 以 水 为溶剂， 反应 48.0h， 生成 (9S)-drummondol
  参考文献：
  名称：

  (6S)-Hydroxy-3-oxo-α-ionol glucosides from Capparis spinosa fruits

  摘要：

  Two new (6S)-hydroxy-3-oxo-alpha-ionol glucosides, together with corchoionoside C ((6S,9S)-roseoside) and a prenyl glucoside, were isolated from mature fruits of Capparis spinosa. The structures were established on the basis of spectroscopic, chiroptic and chemical evidence. In addition, the C-13-resonance of C-9 was found to be of particular diagnostic value in assigning the absolute configuration at that center in ionol glycosides. The alpha-ionol derivatives are metabolites of (+)-(S)-abscisic acid. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(01)00399-5

文献信息

• A Monoterpene Glucoside and Three Megastigmane Glycosides from Juniperus communis var. depressa
  作者：Tsutomu Nakanishi、Naoki Iida、Yuka Inatomi、Hiroko Murata、Akira Inada、Jin Murata、Frank A. Lang、Munekazu Iinuma、Toshiyuki Tanaka、Yoshikazu Sakagami

  DOI：10.1248/cpb.53.783

  日期：——

  A new monoterpene glucoside (1) and three new natural megastigmane glycosides (2—4) were isolated along with a known megastigmane glucoside (5) from twigs with leaves of Juniperus communis var. depressa (Cupressaceae) collected in Oregon, U.S.A., and their structures were determined on the basis of spectral and chemical evidence. In addition, the antibacterial activities of the isolated components against Helicobacter pylori were also investigated.

  从美国俄勒冈州采集的桧柏（Cupressaceae）的枝叶中分离出一种新的单萜葡萄糖苷（1）和三种新的天然大戟烷苷（2-4）以及一种已知的大戟烷葡萄糖苷（5），并根据光谱和化学证据确定了它们的结构。此外，还研究了分离出的成分对幽门螺杆菌的抗菌活性。
• (6S)-Hydroxy-3-oxo-α-ionol glucosides from Capparis spinosa fruits
  作者：İhsan Çalış、Ayşe Kuruüzüm-Uz、Piergiorgio A. Lorenzetto、Peter Rüedi

  DOI：10.1016/s0031-9422(01)00399-5

  日期：2002.2

  Two new (6S)-hydroxy-3-oxo-alpha-ionol glucosides, together with corchoionoside C ((6S,9S)-roseoside) and a prenyl glucoside, were isolated from mature fruits of Capparis spinosa. The structures were established on the basis of spectroscopic, chiroptic and chemical evidence. In addition, the C-13-resonance of C-9 was found to be of particular diagnostic value in assigning the absolute configuration at that center in ionol glycosides. The alpha-ionol derivatives are metabolites of (+)-(S)-abscisic acid. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Ebenamariosides A–D: Triterpene Glucosides and Megastigmanes from the Leaves of <i>Diospyros maritima</i>
  作者：Susumu Kawakami、Erika Miura、Ayaka Nobe、Masanori Inagaki、Motohiro Nishimura、Katsuyoshi Matsunami、Hideaki Otsuka、Mitsunori Aramoto

  DOI：10.1248/cpb.c19-00803

  日期：2019.12.1

  were also isolated. The structures of triterpene glucosides was elucidated with extensive investigation by one and two dimensional NMR spectroscopy and the structures were confirmed by partial enzymatic hydrolyses to give the corresponding mono-glucosides and aglycones. The structures of the megastigmanes, including their absolute stereochemistries, were elucidated by spectroscopic evidence and by the

  用色谱技术分离海产柿（Diospyros maritima）的甲醇（MeOH）提取物中的1-BuOH可溶级分，得到三种新的齐墩果烷型和一种新的乌烷型三萜葡糖苷，称为依贝那马里糖苷AD（1-4）；两个megastigmanes也被隔离。通过一维和二维NMR光谱对三萜糖苷的结构进行了广泛研究，并通过部分酶水解证实了结构，从而给出了相应的单糖苷和糖苷配基。巨型柱头的结构，包括其绝对的立体化学，已通过光谱学证据和改进的Mosher方法得以阐明。两个megastigmanes化学相关联，并明确确定其绝对结构。测定了三萜糖苷及其降解产物的细胞毒性。他们没有显示任何重要活动。