3-O-Methyl-6-desoxy-D-allose | 7045-53-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-Methyl-6-desoxy-D-allose
• 英文别名: 6-deoxy-3-O-methyl-D-allose；6-deoxy-3-O-methyl-allose；(2R,3R,4R,5R)-2,4,5-trihydroxy-3-methoxyhexanal
• CAS: 7045-53-6
• 化学式: C₇H₁₄O₅
• 分子量: 178.185
• InChiKey: MPQBLCRFUYGBHE-UCROKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  12
• 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：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (20R)-3β,8β,11α,12β,14β,20-hexahydroxy-pregn-5-ene 3-O-6-deoxy-3-O-methyl-β-D-allopyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 3.0h， 生成 D-symarose 、 3-O-Methyl-6-desoxy-D-allose
  参考文献：
  名称：

  Dreega volubilis 孕烷甙及其α-葡萄糖苷酶抑制活性

  摘要：

  摘要 采用联合法从毛竹叶的甲醇提取物中分离出三种新的孕烷苷，即毛豆苷 DF (1-3) 以及三种已知的毛豆苷 Da1 (4)、毛豆苷 A (5) 和毛豆苷 N (6)。色谱法。通过 1D-、2D-NMR 和 HR-ESI-MS 光谱阐明了它们的结构，并与文献中报道的进行了比较。与阿卡波糖 (59.8 ± 1.6%) 相比，化合物 5 和 6 在 40 μM 浓度下显示出最显着的 α-葡萄糖苷酶抑制活性，分别抑制 51.3 ± 3.2% 和 50.4 ± 3.1%。

  DOI：

  10.1016/j.phytol.2020.04.013

文献信息

• Five New Pregnane Glycosides from Gymnema sylvestre and Their α-Glucosidase and α-Amylase Inhibitory Activities
  作者：Phan Van Kiem、Duong Thi Hai Yen、Nguyen Van Hung、Nguyen Xuan Nhiem、Bui Huu Tai、Do Thi Trang、Pham Hai Yen、Tran Minh Ngoc、Chau Van Minh、SeonJu Park、Jae Hyuk Lee、Sun Yeou Kim、Seung Hyun Kim

  DOI：10.3390/molecules25112525

  日期：——

  Gymnema sylvestre, a medicinal plant, has been used in Indian ayurvedic traditional medicine for the treatment of diabetes. Phytochemical investigation of Gymnema sylvestre led to the isolation of five new pregnane glycosides, gymsylosides A–E (1–5) and four known oleanane saponins, 3β-O-β-D-glucopyranosyl (1→6)-β-D-glucopyranosyl oleanolic acid 28-O-β-D-glucopyranosyl ester (6), gymnemoside-W1 (7)

  匙羹藤是一种药用植物，已在印度阿育吠陀传统医学中用于治疗糖尿病。匙羹藤的植物化学研究导致分离出五种新的孕烷苷、匙羹藤苷 A-E (1-5) 和四种已知的齐墩果皂苷、3β-O-β-D-吡喃葡萄糖基 (1→6)-β-D-吡喃葡萄糖基齐墩果酸 28-O-β-D-吡喃葡萄糖基酯 (6), 匙羹藤苷-W1 (7), 3β-O-β-D-吡喃木糖基-(1→6)-β-D-吡喃葡萄糖基-(1→6) -β-D-吡喃葡萄糖基齐墩果酸 28-O-β-D-吡喃葡萄糖基酯 (8) 和交替糖苷 XIX (9)。它们的结构是基于光谱证据并与文献中报道的那些进行比较而确定的。评估所有化合物的α-葡萄糖苷酶和α-淀粉酶抑制活性。化合物 2-4 显示出显着的 α-淀粉酶抑制活性，IC50 值范围为 113。
• 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%。
• Four new pregnane glycosides from <i>Gymnema latifolium</i> and their <i>α</i>-glucosidase and <i>α</i>-amylase inhibitory activities
  作者：Duong Thi Hai Yen、Do Thi Trang、Bui Huu Tai、Vu Van Doan、Pham Hai Yen、Nguyen Xuan Nhiem、Chau Van Minh、Manh Hoang Duc、SeonJu Park、Jae Hyuk Lee、Sun Yeou Kim、Seung Hyun Kim、Phan Van Kiem

  DOI：10.1080/14786419.2020.1729153

  日期：2021.11.17

  were tested for α-glucosidase and α-amylase inhibitory activities. Compound 5 exhibited the most anti α-glucosidase activity with inhibitory percentage of 37.8 ± 1.5% at the concentration of 200 μM. Compounds 1–4 showed moderate anti α-glucosidase activity with inhibitory percentage ranging from 7.0 to 30.1%. In addition, all compounds 1–5 showed moderate/weak anti α-amylase activity in the investigated

  摘要 从Gymnema latifolium Wall的叶子中分离出四种新的孕烷苷 A - D ( 1 - 4 ) 和一种已知的孕烷苷 J ( 5 ) 。前怀特。它们的化学结构是在广泛的光谱方法的基础上阐明的，包括 1D、2D NMR、HR-ESI-MS，并与报告的数据进行比较。测试了所有这些化合物的α-葡萄糖苷酶和α-淀粉酶抑制活性。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37.8±1.5%。化合物1-4显示出中度抗α-葡萄糖苷酶活性，抑制百分比范围为 7.0 至 30.1%。此外，所有化合物1-5在研究的测试中都显示出中/弱的抗α-淀粉酶活性。
• Identification and Cytotoxic Evaluation of Pregnane Saponins from the Twigs and Leaves of <i>Dregea volubilis</i>
  作者：Thi Diep Vu、Manh Khoa Nguyen、Thi Thu Nguyen、Thi Hien Tran、Hoang Tuan Nguyen、Thi Ha Do

  DOI：10.1002/cbdv.202301417

  日期：2024.1

  Four new polyhydroxy pregnane glycosides, named volubilosides G−K (3, 5–7), along with three known secondary metabolites, dregeoside D_a1 (1), dregeoside K_a1 (2), and volubiloside E (4) were isolated from the twigs and leaves of Dregea volubilis (DV). The chemical structures of these compounds (1–7) were elucidated using spectroscopic techniques (1D and 2D NMR and HR‐ESI‐MS analyses) and compared with those in the published literature. Compounds (1–7) were evaluated for cytotoxicity against eight cancer cell lines (MB49, K562, MKN‐7, HT29, A549, MCF‐7, MDA‐MB‐231, and HepG2), revealing varying levels of cytotoxic effects with IC₅₀ values ranging from 4.29 to 21.05 μM. The results indicated that compounds 1–7 may serve as potential lead compounds for the discovery and development of novel anti‐cancer drugs.

  摘要 从Dregea volubilis（DV）的枝叶中分离出四种新的多羟基孕烷苷，命名为volubilosides G-K（3，5-7），以及三种已知的次级代谢产物dregeoside Da1（1）、dregeoside Ka1（2）和volubiloside E（4）。利用光谱技术（一维和二维核磁共振以及 HR-ESI-MS 分析）阐明了这些化合物（1-7）的化学结构，并将其与已发表的文献进行了比较。评估了化合物（1-7）对八种癌细胞株（MB49、K562、MKN-7、HT29、A549、MCF-7、MDA-MB-231 和 HepG2）的细胞毒性，结果显示了不同程度的细胞毒性作用，IC50 值从 4.29 到 21.05 μM。研究结果表明，化合物 1-7 可作为发现和开发新型抗癌药物的潜在先导化合物。
• SELECTIVE SEPARATION OR EXTRACTION OF STEROIDAL GLYCOSIDES BY SUPERCRITICAL FLUID EXTRACTION USING CARBON DIOXIDE
  申请人：Unilever N.V.

  公开号：EP1756140B1

  公开（公告）日：2011-03-09