α-L-cymaropyranoside | 45876-76-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-L-cymaropyranoside
• 英文别名: α-L-cymaropyranose；α-L-cymarose；α-cymaropyranose；2,6-dideoxy-3-O-methyl-α-L-ribo-hexose；β-L-cymaropyranose；β-L-cymarose；L-cymarose；alpha-L-Cymarose pyranose；(2R,4R,5S,6S)-4-methoxy-6-methyloxane-2,5-diol
• CAS: 45876-76-4
• 化学式: C₇H₁₄O₄
• 分子量: 162.186
• InChiKey: DBDJCJKVEBFXHG-WNJXEPBRSA-N

物化性质

• 沸点：
  288.7±40.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  cynanotoside D 在 cynanotoside B 、 水 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 β-D-digitoxopyranose 、 α-L-cymaropyranoside
  参考文献：
  名称：

  Neuroprotective polyhydroxypregnane glycosides from Cynanchum otophyllum

  摘要：

  Five new polyhydroxypregnane glycosides, namely cynanotosides A-E (1-5), together with two known analogues, deacetylmetaplexigenin (6) and cynotophylloside H (7), were isolated from the roots of Cynanchum otophyllum. Their structures were established by spectroscopic methods and acid hydrolysis. The neuroprotective effects of compounds 1-7 against glutamate-, hydrogen peroxide-, and homocysteic acid (HCA)-induced cell death were tested by MTT assay in a hippocampal neuronal cell line HT22. Compounds 1, 2, and 7 exhibited protective activity against HCA-induced cell death in a dose-dependent manner ranging from 1 to 30 mu M, which may explain the Traditional Chinese Medicine (TCM) use of this plant for the treatment of epilepsy. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2013.06.007

文献信息

• A New Steroidal Glycoside from Roots of Cynanchum wallichii
  作者：Ding Wang、Yong-Rui Bao

  DOI：10.1007/s10600-015-1443-0

  日期：2015.9

  One new and three known steroidal glycosides were isolated from the ethyl acetate extract of the roots of Cynanchum wallichii Wight. Their structures were characterized as qinyangshengenin-3-O-α-Lcymaropyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-Ddigitoxopyranoside (1), otophylloside A (2), otophylloside B (3), and cynanauriculoside A (4).

  从牛皮消根的乙酸乙酯提取物中分离得到1个新的和3个已知的甾体苷类化合物。它们的结构被鉴定为：芩阳生根苷-3-O-α-L-肉苁蓉糖基-(1→4)-β-D-欧夹豆藤糖基-(1→4)-β-D-肉苁蓉糖基-(1→4)-β-D-毛地黄糖苷（1）、耳叶苷A（2）、耳叶苷B（3）和牛皮消环苷A（4）。
• Studies on the constituents of asclepiadaceae plants. LXVI The structures of three new glycosides, cynapanosides A, B, and C, from the Chinese drug "Xu-Chang-Qing," Cynanchum paniculatum Kitagawa.
  作者：KO SUGAMA、KOJI HAYASHI、HIROSHI MITSUHASHI、KO KANEKO

  DOI：10.1248/cpb.34.4500

  日期：——

  Three new glycosides named cynapanosides A (1), B (2), and C (3) which contain a new aglycone, glaucogenin D (10), were isolated from Cynanchum paniculatum, in addition to the known compounds, cynatratoside B (5) and 3β, 14-dihydroxy-14β-pregn-5-en-20-one (13). Their structures were elucidated by spectroscopic and chemical methods. The results led us to propose a structure revision of glaucogenin B (11).

  从中获得三种新的糖苷， 名称为 cynapanosides A (1)、B (2) 和 C (3)，它们含有一个新的苷元，即 glaucogenin D (10)，同时还得到了已知化合物 cynatratoside B (5) 和 3β,14-二羟基-14β-孕-5-烯-20-酮 (13)。我们通过光谱和化学方法阐明了它们的结构。这些结果使我们提出了对 glaucogenin B (11) 结构的修正。
• The Asymmetric Syntheses of Methyl <small>D</small>-Digitoxoside, <small>L</small>-Oleandrose and <small>L</small>-Cymarose from Methyl Sorbate, an Achiral Precursor
  作者：Machiko Ono、Xi Ying Zhao、Keisuke Kato、Hiroyuki Akita

  DOI：10.1248/cpb.c12-00308

  日期：——

  addition product (+)-(3S,4S,5R)-9 possessing a 3,4-cis-dihydroxy-δ-lactone in 78% overall yield from (4S,5R)-4. The obtained (+)-(3S,4S,5R)-9 was subsequently converted to methyl D-digitoxoside (pyranoside) (12) in 13% overall yield and methyl D-digitoxoside (furanoside) (12) in 20% overall yield. The reaction of benzyl-osmundalactone (4R,5S)-3 and MeOH in the presence of Amberlyst A-26 as a basic catalyst

  向渗透性内酯（4S，5R）-4中添加4 eq的氯醛可定量形成半缩醛衍生物（4S，5R）-8，将其用甲烷磺酸处理，得到分子内的Micheal加成产物（+）-（具有3,4-顺式-二羟基-δ-内酯的3S，4S，5R）-9从（4S，5R）-4的总产率为78％。随后将获得的（+）-（3S，4S，5R）-9转化为总产率为13％的甲基D-数字氧苷（吡喃糖苷）（12）和总产率为20％的甲基D-数字氧苷（呋喃糖苷）（12） 。在Amberlyst A-26作为碱性催化剂的存在下，苄基-磺基内酯（4R，5S）-3与MeOH的反应得到3,4-trans-δ-内酯（-）-（3S，4R，5S）-20产率为28％，3,4-顺-δ-内酯（-）-（3R，4R，5S）-21产率为45％。（-）-（3S，4R，5S）-20的Dibal-H还原反应，然后进行催化加氢得到L-夹竹桃糖（6），总产率为86％，
• [EN] 3-O-GLYCOSYL 16-MEMBERED MACROLIDE ANTIBACTERIALS AND RELATED DERIVATIVES
  申请人：SCHERING CORPORATION

  公开号：WO1988008426A1

  公开（公告）日：1988-11-03

  (EN) 3-O-Glycosyl derivatives of 16-membered macrolides such as O-$g(a)-L-cladinosyl-(1$m(8)3)-12,13-dehydro-12,13-deoxorosaramicin, 2'',4'',4'''-tri-O-acetyl-O-(4'-O-phenoxyacetyl-$g(a)-L-cladinosyl)-(1$m(8)3)-desmycosin and pharmaceutically acceptable acid addition salts thereof useful as antibacterials are disclosed.(FR) Dérivés 3-O-glycosyle de macrolides à 16 membres tels que O-$g(a)-L cladinosyle-(1$m(8)3)-12,13-déshydro-12,13-déoxorosaramicine, 2'', 4'', 4'''-tri-O-acétyle-O-(4'-O-phénoxyacétyle-$g(a)-L-cladinosyle)-(1$m(8)3)-desmycosine, ainsi que leurs sels d'addition d'acide pharmaceutiquement acceptables utiles à titre de substances antibactériennes.

  大环丁烷酯类药物的 16 周期衍生物，如 O-$g(a)-L-卡.dump-（1$m(8)3）-12,13-脱氢-12,13-脱氧罗萨拉 middleware（简写为 O-?[La(aa, L-卡.dump-) - (1$m(8)3)]），以及它们的制药可接受酸性盐，作为抗菌剂具有重要的生理作用。
• New pregnane saponins from Ecdysanthera rosea and their cytotoxicity
  作者：Xiangdong Zhu、Guisheng Wu、Jianying Xiang、Huairong Luo、Shide Luo、Hongmei zhu、Yifen Wang

  DOI：10.1016/j.fitote.2011.01.022

  日期：2011.6

  Two new pregnane saponins elucidated as ecdysantheroside A (1) and ecdysantheroside B (2) and six known compounds (3-8) based on spectral data (MS, IR, 1D and 2D NMR) were isolated from the stem bark of Ecdysanthera rosea. The cytotoxicity against six cell lines of these compounds was tested by MTT assay. The results revealed that compounds 5 and 7 showed cytotoxicity against all the cell lines. Compound 2 showed cytotoxicity against cells A549, MDA435, HepG2, and HUVEC, while compound 4 showed cytotoxicity against cells A549, CEM, and HUVEC. Compound 6 had cytotoxicity against the others except cell HepG2. (C) 2011 Elsevier B.V. All rights reserved.