D-oleandrose | 6786-76-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-oleandrose
• 英文别名: oleandrose；(3R,4R,5R)-4,5-dihydroxy-3-methoxyhexanal
• CAS: 6786-76-1；909877-35-6；18607-77-7
• 化学式: C₇H₁₄O₄
• 分子量: 162.186
• InChiKey: GOYBREOSJSERKM-FSDSQADBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  D-oleandrose 在 溴 作用下， 生成 O³-methyl-D-arabino-2,6-dideoxy-hexonic acid-4-lactone
  参考文献：
  名称：

  合成2-脱氧- D-奎诺糖基-3-甲基醚（d -oleandrose）。脱氧糖。第五次沟通

  摘要：

  DOI：

  10.1002/hlca.194402701173
• 作为产物：
  描述：

  deoxyamplexicogenin A 3-O-β-D-oleandropyranoside 在 盐酸 、 水 作用下， 反应 2.5h， 生成 D-oleandrose
  参考文献：
  名称：

  Nine new steroidal glycosides from the roots of Cynanchum stauntonii

  摘要：

  Nine new steroidal glycosides, named as stauntosides C-K (2, 5, 7-10, 13, 14, and 16), along with seven known compounds (1, 3, 4, 6, 11, 12, and 15) were isolated from the 95% ethanol extract of the roots of Cynanchum stauntonii. The structures of these new compounds were elucidated on the basis of extensive spectroscopic analyses, mainly 1D and 2D NMR, and HRESI-MS, and qualitative chemical methods. Their significance in terms of the chemotaxonomy of C. stauntonii is discussed. (c) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.10.007

文献信息

• Steroidal Glycosides from Roots of Cynanchum otophyllum
  作者：Xin-Xin Yang、Yong-Rui Bao、Shuai Wang、Rui-Qing Zhu、Li-Na Bao、Yu-Peng Guan、Xian-Sheng Meng

  DOI：10.1007/s10600-015-1388-3

  日期：2015.7

  Four steroids were isolated from the ethyl acetate extract of the roots of Cynanchum otophyllum. Their structures were identified as qinyangshengenin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside (1), gagamine (2), otophylloside B (3), and caudatin (4). Compound 1 is a new steroidal glycoside, and the structures of these compounds were established on the basis of chemical and spectroscopic methods.

  从牛皮消（Cynanchum otophyllum）根部的乙酸乙酯提取物中分离得到4个甾体化合物，其结构被鉴定为：青阳参苷（qinyangshengenin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside，1）、加加明（gagamine，2）、牛皮消苷B（otophylloside B，3）和牛皮消苷元（caudatin，4）。化合物1是一种新的甾体糖苷，这些化合物的结构是通过化学和光谱方法确定的。
• Cytotoxic polyhydroxylated pregnane glycosides from <i>Cissampelos pareira</i> var. <i>hirsuta</i>
  作者：Yan-Jun Sun、Hao-Jie Chen、Rui-Jie Han、Chen Zhao、Ying-Ying Si、Meng Li、Kun Du、Hui Chen、Wei-Sheng Feng

  DOI：10.1039/d1ra07498a

  日期：——

  lines, and inhibitory activity against NO release in LPS-induced RAW 264.7 cells. Compared with cisplatin, compound 7 showed more potent cytotoxicities against the HL-60, A549, SMMC-7721, MCF-7, and SW480 cell lines, with IC50 values of 2.19, 14.38, 2.00, 7.58, and 7.44 μM, respectively. The preliminary study of structure-activity relationship indicated that benzoic acid esterification at C-20 may have

  从 Cissampelos pareiRA var. 的干燥全草中分离出 14 种新的多羟基孕烷苷，西萨类固醇 AN (1-14) 和 5 种已知类似物 (15-19)。毛田。它们的结构和立体化学通过大量的光谱数据、化学水解和 ECD 测量得到阐明。测试了所有化合物对五种人类癌细胞系的细胞毒性，以及对 LPS 诱导的 RAW 264.7 细胞中 NO 释放的抑制活性。与顺铂相比，化合物7对HL-60、A549、SMMC-7721、MCF-7和SW480细胞系表现出更强的细胞毒性，IC50值分别为2.19、14.38、2.00、7.58和7.44 μM。构效关系的初步研究表明，C-20位苯甲酸酯化可能对多羟基孕烷衍生物在这五种人类癌细胞系中的细胞毒活性产生负面影响。这些结果揭示了化合物 7 作为理想的抗肿瘤先导化合物的潜力。
• C 21 steroidal glycosides from the roots of Cynanchum paniculatum
  作者：Dan Zhao、Baomin Feng、Shaofei Chen、Gang Chen、Zhifeng Li、Xiaojie Lu、Xianan Sang、Xiao An、Haifeng Wang、Yuehu Pei

  DOI：10.1016/j.fitote.2016.07.001

  日期：2016.9

  As a part of our continuing research for bioactive constituents from Cynanchum plants, four new C21 steroidal glycosides, cynapanoside D-G (1-4), together with six known compounds (5-10) were isolated from the roots of Cynanchum paniculatum (Bge.) Kitag. Their structures were elucidated on the basis of 1D- and 2D-NMR spectroscopic data as well as HR-ESI-MS analysis. Compound 8 exhibited potent inhibitory

  作为我们不断进行的针对虎草植物生物活性成分研究的一部分，从沙地草根（Bge。）的根中分离出四种新的C21类固醇糖苷，Cynapanoside DG（1-4）以及六种已知化合物（5-10）。 Kitag。根据1D和2D-NMR光谱数据以及HR-ESI-MS分析，阐明了它们的结构。化合物8表现出对HL-60，HT-29，PC-3和MCF-7细胞系的有效抑制活性，IC50值分别为8.3、7.5、34.3和19.4μM，化合物1-4和9对HL-60，HT-29，PC-3和MCF-7细胞具有中等的细胞毒性。四个细胞系。通过DPPH自由基清除活性来测定化合物1-4、8和9的体外抗氧化活性。还测试了化合物1-4、8和9的抗菌和抗真菌活性。
• New C 21 steroidal glycosides from the roots of Cynanchum stauntonii and their protective effects on hypoxia/reoxygenation induced cardiomyocyte injury
  作者：Qiao-Shi Lei、Yi-Han Zuo、Chang-Zhi Lai、Jin-Fang Luo、Shu-Wen Pang、Hua Zhou、Xin-Sheng Yao、Jin-Shan Tang

  DOI：10.1016/j.cclet.2017.05.017

  日期：2017.8

  Abstract Phytochemical investigations from the roots of Cynanchum stauntonii led to obtain four new C 21 steroidal glycosides ( 1 – 4 ) and one known compound stauntoside F ( 5 ). Their chemical structures were characterized by sophisticated analyses of IR, HRESI-TOF-MS, 1D, and 2D-NMR data, together with chemical methods, which showed interesting 13,14:14,15-disecopregnane-type skeleton or 14,15-secopregnane-type

  摘要从梧桐的根部进行植物化学研究后，获得了四种新的C 21甾体糖苷（1-4）和一种已知的化合物stauntoside F（5）。通过对IR，HRESI-TOF-MS，1D和2D-NMR数据进行精密分析以及化学方法对它们的化学结构进行了表征，这些化学方法显示出有趣的13,14：14,15-二铜庚烷型骨架或14,15-二十碳四烯烷型骨架C 21甾体糖苷。其中，化合物1被确定为glaucogenin C 3-O-β-d-吡喃葡萄糖基-（1→4）-β-d-环吡喃糖基-（1→4）-β-d -digitoxopyranosyl-（1→4） -β-d-thevetopyranoside。化合物2的特征是Hirundigenin 3- O-α-1-diginopyranosyl-（1→4）-β-d -cymaropyranosyl-（1→4）-β-d -digitoxopyranosyl-（1→4）-β-d
• Pregnane glycosides from <i>Gymnema inodorum</i> and their α-glucosidase inhibitory activity
  作者：Do Thi Trang、Duong Thi Hai Yen、Nguyen The Cuong、Luu The Anh、Nguyen Thi Hoai、Bui Huu Tai、Vu Van Doan、Pham Hai Yen、Tran Hong Quang、Nguyen Xuan Nhiem、Chau Van Minh、Phan Van Kiem

  DOI：10.1080/14786419.2019.1663517

  日期：2021.7.3

  Abstract Two new pregnane glycosides, gyminosides A and B (1 and 2) and three known, tinctoroside B (3), tinctoroside C (4), and gymnepregoside F (5) were isolated from the leaves of Gymnema inodorum (Lour.) Decne. Their structures were elucidated by physical and chemical methods and comparing with those reported in the literature. All these compounds were evaluated for α-glucosidase assay. Compound

  摘要 从Gymnema inodorum (Lour.) Decne的叶子中分离出两种新的孕烷苷类，gyminosides A 和 B（1和2）以及三种已知的 tinctoroside B ( 3 )、tinctoroside C ( 4 ) 和裸子菊甙 F ( 5 ) 。通过物理和化学方法阐明了它们的结构，并与文献中报道的结构进行了比较。对所有这些化合物进行了α-葡萄糖苷酶测定。化合物5在200 μM浓度下表现出最大的抗α-葡萄糖苷酶活性，抑制率为63.7±3.9%。化合物1 - 4表现出中等抗α-葡萄糖苷酶活性，抑制百分比范围为 40.0 至 52.1%。