(2R)-1-O-[α-D-galactopyranosyl-(1''->6')-O-β-D-galactopyranosyl] glycerol | 33600-42-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: (2R)-1-O-[α-D-galactopyranosyl-(1''->6')-O-β-D-galactopyranosyl] glycerol
• 英文别名: (2R)-3-O-[α-D-galactopyranosyl-(1''''->6''')-O-β-D-galactopyranosyl]glycerol；3-O-α-D-galactopyranosyl(1<*>6)-O-β-D-galactopyranosyl-sn-glycerol；(2R)-3-O-[α-D-galactopyranosyl-(1''''->6''')-O-β-D-galactopyranosyl]-sn-glycerol；1-O-[α-D-galactopyranosyl-(1''->6')-O-β-D-galactopyranosyl]glycerol；((R)-2,3-dihydroxy-propyl)-(O⁶-α-D-galactopyranosyl-β-D-galactopyranoside)；((R)-2,3-Dihydroxy-propyl)-(O⁶-α-D-galactopyranosyl-β-D-galactopyranosid)；(2’R)-glyceryl 6-O-(α-D-galactopyranosyl)-β-D-galactopyranoside；(2S,3R,4S,5R,6R)-2-[[(2R,3R,4S,5R,6R)-6-[(2R)-2,3-dihydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 33600-42-9
• 化学式: C₁₅H₂₈O₁₃
• 分子量: 416.38
• InChiKey: CPJPQXHWHOMKBP-HQDWSMQCSA-N

物化性质

• 沸点：
  824.1±65.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.5
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  219
• 氢给体数：
  9
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  姜糖酯B 在 甲醇 、 sodium methylate 作用下， 生成 (2R)-1-O-[α-D-galactopyranosyl-(1''->6')-O-β-D-galactopyranosyl] glycerol
  参考文献：
  名称：

  A Metabolomic Approach for the Discrimination of Red Ginseng Root Parts and Targeted Validation

  摘要：

  人参皂苷被用作衡量红参质量的现有指标，人参皂苷的比例也能说明红参的不同成分。为了对人参皂苷的含量进行分析和分类，将红参分为主根、侧根和细根三个部分，并对每个提取物进行超高效液相色谱-四重飞行时间质谱（UPLC-QToF-MS）和多元统计分析。主成分分析（PCA）显示主根和细根提取物之间有明显的区别，并提出了区别标记（主根四个，细根五个）。细根标记被鉴定为人参皂苷。在这项研究中，我们确定了红参主根的两个标记。此外，我们还分析了红参三种成分中 22 种人参皂苷的含量。细根具有最高的原人参二醇（PPD）/原人参三醇（PPT）比率。人参皂苷的 PPD 组在细根中数量上占优势，明显区分了主根和其他部分。

  DOI：

  10.3390/molecules22030471

文献信息

• Stomachic Principles in Ginger. III. An Anti-ulcer Principle, 6-Gingesulfonic Acid, and Three Monoacyldigalactosylglycerols, Gingerglycolipids A, B, and C, from Zingiberis Rhizoma Originating in Taiwan.
  作者：Masayuki YOSHIKAWA、Shoko YAMAGUCHI、Kumiko KUNIMI、Hisashi MATSUDA、Yasuhiro OKUNO、Johji YAMAHARA、Nobutoshi MURAKAMI

  DOI：10.1248/cpb.42.1226

  日期：——

  monoacyldigalactosylglycerols, gingerglycolipids A, B, and C, were isolated from Zingiberis Rhizoma, the dried rhizome of Zingiber officinale Roscoe which was cultivated in Taiwan, together with (+)-angelicoidenol-2-O-beta-D-glucopyranoside. Based on chemical reactions and physicochemical evidence, the structures of 6-gingesulfonic acid, gingerglycolipids A, B, and C have been determined. In addition, the absolute

  从台湾种植的生姜的干根茎姜黄中分离出抗溃疡成分6-姜磺酸和三种单酰基二乳糖基甘油A，B和C姜糖脂，以及（+）-Angelicoidenol- 2-O-β-D-吡喃葡萄糖苷。基于化学反应和物理化学证据，已经确定了6-姜磺酸，姜糖脂A，B和C的结构。另外，基于其从d-冰片的合成，阐明了（+）-Angelioidenenol-2-O-β-D-吡喃葡萄糖苷的绝对立体结构。6-氨基磺酸的辛辣性较6-姜醇和6-寿果酚弱，且抗溃疡作用更强。
• Anti-tumour-promoting glyceroglycolipids from the green alga, Chlorella vulgaris
  作者：Takashi Morimoto、Akito Nagatsu、Nobutoshi Murakami、Jinsaku Sakakibara、Harukuni Tokuda、Hoyoku Nishino、Akio Iwashima

  DOI：10.1016/0031-9422(95)00458-j

  日期：1995.11

  Two new monogalactosyl diacylglycerols were isolated from the freshwater green alga, Chlorella vulgaris, as anti-tumour promoters, together with three monogalactosyl diacylglycerols and two digalactosyl diacylglycerols. The new monogalactosyl diacylglycerol containing (7Z,10Z)-hexadecadienoic acid showed a more potent inhibitory effect toward tumour promotion than the other glycerolipids isolated.
• A monoacyl galactosylglycerol from sonchus arvensis
  作者：Putul Baruah、Nabin C. Baruah、Ram P. Sharma、Jogendra N. Baruah、Palianappan Kulanthaivel、Werner Herz

  DOI：10.1016/s0031-9422(00)80262-9

  日期：1983.1
• Synthesis of digalactosyl diacylglycerols and their structure–inhibitory activity on human lanosterol synthase
  作者：Rie Tanaka、Yuichi Sakano、Akito Nagatsu、Masaaki Shibuya、Yutaka Ebizuka、Yukihiro Goda

  DOI：10.1016/j.bmcl.2004.10.013

  日期：2005.1

  Digalactosyl and monogalactocyl diacylglycerols (DGDG and MGDG), which were identified as anti-hyperlipemia active components in Colocasia esculenta (Taro), were synthesized. The inhibitory activity of DGDG, MGDG and related compounds on human lanosterol synthase was evaluated as anti-hyperlipemic activity. DGDG with two myristoyl groups at both sn-1 and sn-2 positions and with an oleoyl group at the sn-1 position showed the most potent activity. (C) 2004 Elsevier Ltd. All rights reserved.
• Constituents of <i>Ocimum sanctum</i> with Antistress Activity
  作者：Prasoon Gupta、Dinesh Kumar Yadav、Kiran Babu Siripurapu、Guatam Palit、Rakesh Maurya

  DOI：10.1021/np0700164

  日期：2007.9.1

  Three new compounds, ocimumosides A (1) and B (2) and ocimarin (3), were isolated from an extract of the leaves of holy basil (Ocimum sanctum), together with eight known substances, apigenin, apigenin-7-O-beta-D-glucopyranoside, apigenin-7-O-beta-D-glucuronic acid (4), apigenin-7-O-beta-D-glucuronic acid 6 ''-methyl ester, luteolin-7-O-beta-D-glucuronic acid 6 ''-methyl ester, luteolin-7-O-beta-D-glucopyranoside, luteolin-5-O-beta-D-glucopyranoside, and 4-allyl-1-O-beta-D-glucopyronosyl-2-hydroxybenzene (5), and two known cerebrosides. The structures of the new compounds were determined on the basis of extensive 1D and 2D NMR spectroscopic analysis. The new compounds (1-3) and the known compounds 4 and 5 were screened at a dose of 40 mg/kg body weight for acute stress-induced biochemical changes in male Sprague-Dawley rats. Compound 1 displayed promising antistress effects by normalizing hyperglycemia, plasma corticosterone, plasma creatine kinase, and adrenal hypertrophy. Compounds 2 and 5 were also effective in normalizing most of these stress parameters. In contrast, compounds 3 and 4 were ineffective in normalizing any of these effects.