6-(6-deoxy-β-D-glucopyranosyloxy)-2,6-dimethyl[S-(E)]-2,7-octadienoic acid | 156733-35-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(6-deoxy-β-D-glucopyranosyloxy)-2,6-dimethyl[S-(E)]-2,7-octadienoic acid
• 英文别名: (6S)-2-trans-2,6-dimethyl-6-O-β-D-quinovopyranosyl-2,7-octadienoic acid；(6S)-2-trans-2,6-dimethyl-6-O-β-D-quinovosyl-2,7-octadienoic acid；(6S)-menthiafolic acid 6-O-β-D-quinovoside；(6S)-menthiafolic acid-6-O-β-D-quinovoside；(2E,6S)-2,6-dimethyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyocta-2,7-dienoic acid
• CAS: 156733-35-6
• 化学式: C₁₆H₂₆O₇
• 分子量: 330.378
• InChiKey: GGHLYRUPOWRANQ-MPBKKTJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-(6-deoxy-β-D-glucopyranosyloxy)-2,6-dimethyl[S-(E)]-2,7-octadienoic acid 在 sodium hydroxide 、 sodium acetate 、 β-glucosidase 作用下， 以 水 为溶剂， 反应 72.0h， 生成 (2E,6S)-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid
  参考文献：
  名称：

  Diastereoisomeric saponins from Albizia julibrissin

  摘要：

  The structures of four new diastereoisomeric triterpenoidal saponins Julibroside J(5), J(8), J(12) and J(13) (1-4) isolated from Albizia julibrissin Durazz. (Leguminosae) have been determined on the basis of comprehensive spectroscopic analysis and chemical degradation. Julibroside, J(8) and J(13) showed marked cytotoxic activities against Bel-7402 cancer cell line at 100 mu g/mL. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.10.027
• 作为产物：
  描述：

  julibroside J₈ 在 碳酸氢钠 作用下， 以 水 为溶剂， 反应 1.0h， 以2.2 mg的产率得到6-(6-deoxy-β-D-glucopyranosyloxy)-2,6-dimethyl[S-(E)]-2,7-octadienoic acid
  参考文献：
  名称：

  Diastereoisomeric saponins from Albizia julibrissin

  摘要：

  The structures of four new diastereoisomeric triterpenoidal saponins Julibroside J(5), J(8), J(12) and J(13) (1-4) isolated from Albizia julibrissin Durazz. (Leguminosae) have been determined on the basis of comprehensive spectroscopic analysis and chemical degradation. Julibroside, J(8) and J(13) showed marked cytotoxic activities against Bel-7402 cancer cell line at 100 mu g/mL. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.10.027

文献信息

• A new complex triterpenoid saponin from Calliandra pulcherrima with haemolytic activity and adjuvant effect
  作者：Bernadete Pereira da Silva、José Paz Parente

  DOI：10.1016/j.phytol.2013.08.009

  日期：2013.11

  compounds its structure was established as 3-[(O-α-l-arabinopyranosyl-(1 → 2)-O-α-l-arabinopyranosyl-(1 → 6)-2-(acetylamino)-2-deoxy-β-d-glucopyranosyl)oxy]-(3β)-olean-12-en-28-oic acid O-β-d-xylopyranosyl-(1 → 3)-O-β-d-xylopyranosyl-(1 → 4)-O-[(β-d-glucopyranosyl-(1 → 3)]-O-6-deoxy-α-l-mannopyranosyl-(1 → 2)-6-O-[(2E,6S)-6-[[2-O-[(2E,6S)-6-[[6-deoxy-2-O-[(2E,6S)-2,6-dimethyl-1-oxo-6-(β-d-xylopyranosyloxy)-2

  通过色谱法从Calliandra pulcherrima的叶片中分离出一种新的复杂的三萜皂苷。根据化学证据，对已知化合物进行光谱分析和比较，确定其结构为3-[（O- α - l-阿拉伯吡喃糖基- （1→2）-O- α - l-阿拉伯吡喃糖基-（1→6） -2-（乙酰基氨基）-2-脱氧β - d吡喃葡萄糖基）氧基] - （3- β）-olean -12-烯-28-酸O- β - d -xylopyranosyl-（1→3）-O - β - d -xylopyranosyl-（1→4）-O - [（β - d-吡喃葡萄糖基- （1→3）]-O-6-脱氧-α - 1-甘露吡喃糖基- （1→2）-6-O-[（2E，6S）-6-[[2-O-[（2E ，6S）-6-[[[6-脱氧-2-O-[（2E，6S）-2,6-二甲基-1-氧代-6-（β - d-吡喃吡喃糖基氧基）-2,7-辛二烯基]- β - d-吡喃葡萄糖基]氧基]
• Ingasaponin, a complex triterpenoid saponin with immunological adjuvant activity from Inga laurina
  作者：Maria de Fátima Simão Jucá Cruz、Gabriela Moysés Pereira、Marcela Gonçalves Ribeiro、Ari Miranda da Silva、Luzineide Wanderley Tinoco、Bernadete Pereira da Silva、José Paz Parente

  DOI：10.1016/j.carres.2015.11.008

  日期：2016.2

  7-octadienyl]oxy]-16-hydroxy -3-[[O-beta-D-xylopyranosyl-(1 --> 2)-O-alpha-L-arabinopyranosyl-(1 --> 6)-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl]oxy]-(3beta,16alpha,21beta)-olea n-12-en-28-oic acid O-alpha-L-arabinofuranosyl-(1 --> 4)-O-[beta-D-glucopyranosyl-(1 --> 3)]-O-6-deoxy-alpha-L-mannopyranosyl-(1 --> 2)-beta-D-glucopyranosyl ester (1). The hemolytic potential of 1 was evaluated using in vitro assays, and

  作为我们从巴西植物中搜索生物活性皂苷的一部分，对月桂印加种子的植物化学研究导致分离出一种名为ingasaponin的新的复杂三萜皂苷。它是从印加属中分离出的第一种皂苷。使用色谱方法进行分离，并使用包括2D-NMR光谱技术和化学转化在内的（1）H和（13）C NMR光谱进行详细分析，进行结构解析。其结构被确定为21-[[（（2E，6S）-6]-[[6-deoxy-4-O-[（2E，6S）-6-[[β-D-吡喃葡萄糖基）氧基] -2,6 -二甲基-1-氧代-2,7-辛二烯基]-[（β-D-吡喃葡萄糖基）氧基] -2,6-二甲基-1-氧代-2,7-辛二烯基]-[（β-D-吡喃葡萄糖基）氧基] -2,6-二甲基-1-羰基-2,7-辛二烯基]-[（β-D-gl铀基吡喃糖基）氧基] -2-（羟甲基）-6-甲基-1-羰基-2，7-辛二烯基]氧基] -16-羟基-3-[[O-β-D-木吡喃糖基-（1->
• Studies on the Constituents of Calliandra anomala (KUNTH) MACBR. II. Structure Elucidation of Four Acylated Triterpenoidal Saponins.
  作者：Takatoshi NAKAMURA、Tadahiro TAKEDA、Yukio OGIHARA

  DOI：10.1248/cpb.42.1111

  日期：——

  Four new triterpenoidal saponins, called calliandra saponins B (8), C (9), D (10), and F (12), were isolated from the branches of Calliandra anomala (KUNTH) MACBR. The structures of these compounds were established on the basis of NMR spectra, FAB-MS, and the chemical evidence.These saponins, interestingly, have a N-acetyl glucosamine at the 3 position of the genin, and one or two monoterpene glycosides at the position of the sugar chain.

  根据核磁共振波谱、FAB-MS 和化学证据确定了四种新的三萜类皂苷，即 Calliandra 皂苷 B (8)、C (9)、D (10) 和 F (12)。有趣的是，这些皂苷在基因素的 3 位上有一个 N-乙酰氨基葡萄糖，在糖链的位置上有一个或两个单萜苷。